U.S. patent application number 15/640044 was filed with the patent office on 2018-01-18 for methods and formulations for curling hair.
The applicant listed for this patent is Liqwd, Inc.. Invention is credited to Craig J. Hawker, Eric D. Pressly.
Application Number | 20180015015 15/640044 |
Document ID | / |
Family ID | 60941704 |
Filed Date | 2018-01-18 |
United States Patent
Application |
20180015015 |
Kind Code |
A1 |
Pressly; Eric D. ; et
al. |
January 18, 2018 |
METHODS AND FORMULATIONS FOR CURLING HAIR
Abstract
Methods, formulations, and kits for curling and/or preventing
damage in the curling of hair are disclosed herein. Treatment with
one or more hydroxide-containing agents in combination with one or
more active agents can reshape hair, without the need for
sulfur-containing reducing agents. To impart curl to hair, the
active agent(s) and the hydroxide-containing agent(s) are applied
either as a combined formulation or as separate formulations which
are applied simultaneously. Use of the active agent along with a
hydroxide-containing agent allows the level of curl imparted to
hair to be controlled, as compared to the natural amount of curl,
if any, in the untreated hair.
Inventors: |
Pressly; Eric D.; (Santa
Barbara, CA) ; Hawker; Craig J.; (Santa Barbara,
CA) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Liqwd, Inc. |
Santa Barbara |
CA |
US |
|
|
Family ID: |
60941704 |
Appl. No.: |
15/640044 |
Filed: |
June 30, 2017 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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15282795 |
Sep 30, 2016 |
9713583 |
|
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15640044 |
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62380020 |
Aug 26, 2016 |
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62361366 |
Jul 12, 2016 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A61Q 5/04 20130101; A45D
7/04 20130101; A61K 8/466 20130101; A61K 8/41 20130101; A61K
2800/30 20130101; A61K 8/36 20130101; A61K 8/19 20130101; A61K
8/362 20130101; A61K 2800/882 20130101; A61Q 5/06 20130101 |
International
Class: |
A61K 8/41 20060101
A61K008/41; A61K 8/36 20060101 A61K008/36; A61K 8/19 20060101
A61K008/19; A45D 7/04 20060101 A45D007/04; A61Q 5/06 20060101
A61Q005/06; A61K 8/362 20060101 A61K008/362 |
Claims
1. A method comprising: (a) applying to hair a formulation
comprising one or more hydroxide- containing agents; and one or
more active agents selected from the group consisting of maleic
acid, acrylic acid, methyl acrylic acid, and vinyl sulfonic acid,
and simple salts thereof; and (b) reshaping the hair; wherein the
method is substantially free of a sulfur-containing reducing
agent.
2. The method of claim 1, wherein following steps (a) and (b), the
hair retains curl when subjected to one or more wash cycles.
3. The method of claim 1, wherein step (b) occurs prior to step
(a).
4. The method of claim 1, wherein the formulation is a combined
formulation, and wherein prior to step (a), a first and a second
formulation are mixed to form the combined formulation, wherein the
combined formulation has a pH of about 10 or greater.
5. The method of claim 1, wherein the weight ratio of the one or
more hydroxide-containing agents to the one or more active agents
is in the range of about 5:1 to about 1:5.
6. The method of claim 1, wherein the one or more hydroxide-
containing agents are selected from the group consisting of sodium
hydroxide, lithium hydroxide, potassium hydroxide, guanidinium
hydroxide, and ammonium hydroxide.
7. The method of claim 1, wherein the active agent is present in an
amount ranging from about 0.5 wt % to about 10 wt % of the
formulation.
8. The method of claim 1, wherein the step of reshaping the hair
comprises rolling the hair on a roller, rod, or curler, or a
combination thereof.
9. The method of claim 1, further comprising: (c) applying to the
hair a second active agent formulation comprising a second active
agent, wherein the second active agent is maleic acid or a simple
salt thereof, acrylic acid or a simple salt thereof, methyl acrylic
acid or a simple salt thereof, and vinyl sulfonic acid or a simple
salt thereof, ##STR00009## or a mixture thereof; wherein step (c)
occurs subsequent to step (b).
10. The method of claim 9, wherein the second active agent
formulation comprises about 0.1 to about 5 wt % of the second
active agent.
11. A method comprising: (a) applying to hair a formulation
comprising one or more hydroxide-containing agents and maleic acid
or a salt or a mixture thereof; wherein the pH of the formulation
is about 10 or greater; and (b) reshaping the hair; wherein the
method is substantially free of a sulfur-containing reducing
agent.
12. The method of claim 11, wherein following steps (a) and (b),
the hair retains curl when subjected to one or more wash
cycles.
13. The method of claim 11, wherein step (b) occurs prior to step
(a).
14. The method of claim 11, wherein the formulation is a combined
formulation, and wherein prior to step (a), a first and a second
formulation are mixed to form the combined formulation, wherein the
combined formulation has a pH of about 10 or greater.
15. The method of claim 11, wherein the weight ratio of the one or
more hydroxide-containing agents to the maleic acid is in the range
of about 5:1 to about 1:5.
16. The method of claim 11, wherein the one or more
hydroxide-containing agents are selected from the group consisting
of sodium hydroxide, lithium hydroxide, potassium hydroxide,
guanidinium hydroxide, and ammonium hydroxide.
17. The method of claim 11, wherein the active agent is present in
an amount ranging from about 0.5 wt % to about 10 wt % of the
formulation.
18. The method of claim 11, wherein the step of reshaping the hair
comprises rolling the hair on a roller, rod, or curler, or a
combination thereof.
19. The method of claim 11, further comprising: (c) applying to the
hair a second active agent formulation comprising a second active
agent, wherein the second active agent is maleic acid or a simple
salt thereof, acrylic acid or a simple salt thereof, methyl acrylic
acid or a simple salt thereof, vinyl sulfonic acid or a simple salt
thereof, ##STR00010## or a mixture thereof; wherein step (c) occurs
subsequent to step (b).
20. The method of claim 19, wherein the second active agent
formulation comprises about 0.1 to about 5 wt % of the second
active agent.
21. A method comprising: (a) applying to hair a formulation
comprising one or more hydroxide-containing agents and one or more
active agents selected from the group consisting of: ##STR00011##
and (b) reshaping the hair; and wherein the method is substantially
free of a sulfur-containing reducing agent.
22. The method of claim 21, wherein following steps (a) and (b),
the hair retains curl when subjected to one or more wash
cycles.
23. The method of claim 21, wherein step (b) occurs prior to step
(a).
24. The method of claim 21, wherein the formulation is a combined
formulation, and wherein prior to step (a), a first and a second
formulation are mixed to form the combined formulation, wherein the
combined formulation has a pH of about 10 or greater.
25. The method of claim 21, wherein the weight ratio of the one or
more hydroxide-containing agents to the one or more active agents
is in the range of about 5:1 to about 1:5.
26. The method of claim 21, wherein the one or more hydroxide-
containing agents are selected from the group consisting of sodium
hydroxide, lithium hydroxide, potassium hydroxide, guanidinium
hydroxide, and ammonium hydroxide.
27. The method of claim 21, wherein the active agent is present in
an amount ranging from about 0.5 wt % to about 10 wt % of the
formulation.
28. The method of claim 21, wherein the step of reshaping the hair
comprises rolling the hair on a roller, rod, or curler, or a
combination thereof.
29. The method of claim 21, further comprising: (c) applying to the
hair a second active agent formulation comprising a second active
agent, wherein the second active agent is maleic acid or a simple
salt thereof, acrylic acid or a simple salt thereof, methyl acrylic
acid or a simple salt thereof, vinyl sulfonic acid or a simple salt
thereof, ##STR00012## or a mixture thereof; wherein step (c) occurs
subsequent to step (b).
30. The method of claim 29, wherein the second active agent
formulation comprises about 0.1 to about 5 wt % of the second
active agent.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority to U.S. application Ser.
No. 15/282,795, filed Sep. 30, 2016, which claims priority to U.S.
Provisional Application Ser. No. 62/380,020, filed Aug. 26, 2016,
and to U.S. Provisional Application Ser. No. 62/361,366, filed Jul.
12, 2016, the disclosures of which are incorporated herein by
reference in their entirety.
FIELD OF THE INVENTION
[0002] The present invention generally relates to formulations and
methods for curling hair, particularly for imparting and
controlling a level of curl to the hair.
BACKGROUND OF THE INVENTION
[0003] Hair consists of many long, parallel chains of amino acids.
These chains, or polymers, of amino acids are bound to each other
via 1) hydrogen bonding, 2) salt bridges between acid and base
groups, and 3) disulfide bonds.
[0004] At alkaline pH, the disulfide bonds in hair can be broken
(Dombrink et al., Chem Matters, 1983, page 8). For example,
lye-based relaxers contain hydroxide ions, which can attack
disulfide linkages. Cleavage of disulfide bonds by the lye-based
relaxer achieves straightening of the hair by changing the relative
positions of polypeptide chains. Rinsing the hair and/or applying a
neutralizing formulation complete the straightening process.
[0005] While lye and other alkali-based relaxers are highly
effective at relaxing and straightening hair, they can result in
reduction of hair strength and potential loss of hair through
breakage. Lye and alkali-based relaxers are not used to perm
hair.
[0006] Traditional perms use thiol or sulfur-containing reducing
agents followed by a second oxidizing step, typically using
hydrogen peroxide, to set the hair. These thiol or
sulfur-containing reducing agents are foul smelling and, if not
properly rinsed between the steps, can damage and/or brake
hair.
[0007] Thus, there is a need for hair curling formulations and
treatments, which provide improved conditioning benefit for hair
when the hair is curled. There is a need to provide long lasting
moisturized feel, smooth feel, and manageability control to curled
hair.
[0008] There is also a need for hair curling formulations and
treatments that afford the ability to tune or select the level of
curl imparted to hair.
[0009] There is a further need for hair curling formulations and
treatments that can be applied to the hair as a single
formulation.
[0010] Additionally, there is a need for hair curling formulations
without a foul-smelling thiol or sulfur-containing agent, or
related odors therefrom.
[0011] Therefore, it is an object of this invention to provide
improved curling formulations and curling methods for repairing
and/or strengthening curled hair.
[0012] It also is an object of this invention to provide curling
formulations and methods that can be used to tune or select the
level of curl imparted to hair.
[0013] It is a further object of this invention to provide hair
curling formulations and treatments that can be applied to the hair
as a single formulation, as well as formulations without a
foul-smelling thiol or sulfur-based odor.
SUMMARY OF THE INVENTION
[0014] Formulations, kits, and methods for curling hair are
described which include the use of hydroxide-containing agents or
formulations thereof in combination with the use of active agents
or formulations thereof. The formulations, kits, and methods can
also be used to control the level of curl imparted to the hair
during the curling process. In certain embodiments, the formulation
for curling hair may be applied one or more times after a hair
curling treatment to change the level of curl in the hair.
[0015] The methods described herein include the step of reshaping
hair prior to, during, or following the application of any
formulation containing one or more active agents and/or one or more
hydroxide-containing agents.
[0016] The methods described herein reshape hair, without the need
for sulfur-containing reducing agents or peroxide-based agents.
[0017] Active agent formulations, which contain one or more
compounds that interact with keratin through one or more binding
events (e.g., absorption, binding, etc.) and can also react with
one or more nucleophiles, such as thiols, in the hair are described
herein. "Binding" as used herein refers to the formation of
covalent, ionic, or hydrogen bonds. The active agent formulations
can also provide improved conditioning and provide long lasting
moisturized and smooth feel without leaving the hair greasy,
improve appearance (e.g., sheen), increase dry strength (tensile
strength), ease combing of the hair when wet or dried, reduce hair
breakage, or decrease frizz, or any combination thereof.
[0018] Traditional methods of curling hair do not use lye or
alkali-based or hydroxide-containing agents, which are known hair
relaxers/straighteners and which can result in reduction of hair
strength and potential loss of hair through breakage. The curling
methods disclosed herein apply to hair active agents in combination
with hydroxide-containing agents (or formulations thereof). These
methods curl hair and repair damage to the curled hair.
Additionally, the curling methods described herein provide improved
methods of styling hair, such as during a hair curling
treatment.
[0019] Use of the one or more active agents permits control of the
level of curl imparted to hair during a hair curling process and
prevents damage caused by the hydroxide-containing agent(s) applied
to the hair.
[0020] A combined formulation containing both the active agent and
one or more hydroxide-containing agents is applied to the hair
during a hair curling process or treatment. Alternatively, an
active agent formulation concurrently with a formulation containing
one or more hydroxide-containing agents is applied during a hair
curling process or treatment. The addition of the active agent(s)
simultaneously with hydroxide-containing agents can be used to tune
or control the level of curl imparted to hair during the curling
process. The level of curl imparted can depend on the amount of
active agent(s) used, which can be represented as a weight ratio of
active agent present in the formulation or formulations applied to
the hair to the amount of hydroxide-containing agent(s) present in
a formulation applied to the hair during the hair curling process.
Preferably, the formulations are applied simultaneously; optionally
they are mixed just prior to application to form a combined
formulation. Alternatively, the active agent and
hydroxide-containing agents may be provided as a single, pre-mixed
combined formulation.
[0021] The pH of the combined formulation is preferably at least
about 9.5, more preferably at least about 10.5. In some
embodiments, the pH of the combined formulation is about 11 or
greater, such as up to about 14. In some embodiments, the pH of the
combined formulation is about 10 or greater, such as up to about
14. When the formulations are mixed at the time of use, preferably,
the amount of active agent formulation used does not lower the pH
of the combined formulation to be below about a pH of 9.5 and more
preferably does not lower the pH of the combined formulation below
about a pH of 10.5.
[0022] The weight ratio of the hydroxide-containing agent
formulation to the active agent formulation can be in the range of
about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In
some embodiments, the weight ratio of the hydroxide-containing
agent formulation to the active agent formulation is in the range
of about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1.
In some instances, the weight ratio is about 10:1, 9:1, 8:1, 7:1,
6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5 or within about
10% of these ratios, preferably the weight ratio is about 5:1, 4:1,
3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5 or within about 10% of these
ratios.
[0023] Instead of simultaneous application, the active agent
formulations can be applied to the hair immediately following or
shortly after (e.g. within 1-5 minutes) the application of the
hydroxide-containing agents, or formulations thereof.
[0024] The curl imparted to the hair following a curling treatment
method defined herein (referred to herein as "imparted curl") can
be maintained with no appreciable or substantially no appreciable
change for a period. The treated hair retains curl when subjected
to conditions, such as one or more wash cycles, under which it
would not retain the curl absent treatment according to the methods
described herein.
[0025] In some embodiments, the percentage of curl is reduced by
less than about 5%, 10%, 15%, 20%, or 50% of the imparted curl
after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40,
45, or 50 or more wash cycles. In certain embodiments, the curl is
retained with no appreciable or substantially no appreciable change
after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40,
45, or 50 or more wash cycles.
DETAILED DESCRIPTION OF THE INVENTION
[0026] I. Definitions
[0027] Numerical ranges disclosed herein disclose individually each
possible number in such range, as well as any sub-ranges and
combinations of sub-ranges encompassed therein. For example, a
carbon range (i.e., C.sub.1-C.sub.10) is intended to disclose
individually every possible carbon value and/or sub-range
encompassed within. For example, a carbon length range of
C.sub.1-C.sub.10 discloses C.sub.1, C.sub.2, C.sub.3, C.sub.4,
C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9, and C.sub.10, as well
as discloses sub-ranges encompassed within, such as
C.sub.2-C.sub.9, C.sub.3-C.sub.8, C.sub.1-C.sub.5, etc. Similarly,
an integer value range of 1-10 discloses the individual values of
1, 2, 3, 4, 5, 6, 7, 8, and 10, as well as sub-ranges encompassed
within. Further, a concentration range or weight percent range,
such as from 1% to 2% by weight of the formulation, discloses the
individual values and fractions thereof, such as 1%, 1.1%, 1.2%,
1.32%, 1.48% etc. , as well as sub-ranges encompassed within.
[0028] The term "hair" refers to one or more than one strand of
hair, as well as the natural components of hair, such as oil from a
body. Hair also refers to virgin hair or processed hair, for
example hair that has been exposed to hair waving or hair
straightening formulations.
[0029] An "effective amount", e.g., of the active agent described
herein, refers to an amount of the active agent in a formulation
which, when applied as part of a desired hair treatment achieves
the desired result, such as desired level of curl, smoothness,
little or no breakage, great or good feel, and/or healthy
appearance by visual inspection.
[0030] "Cosmetically acceptable" refers to those compounds,
materials, and formulations, which are, within the scope of sound
medical judgment, suitable for use in contact with the tissues of
human beings and animals without excessive toxicity, irritation,
allergic response, or other problems or complications commensurate
with a reasonable benefit/risk ratio. More specifically,
cosmetically acceptable refers to a material, compound, or
formulation, which is suitable for use in contact with the skin,
scalp, or hair. Cosmetically acceptable materials are known to
those of ordinary skill in the art. "Shampoo" generally refers to a
liquid or semi-solid formulation applied to the hair that contains
detergent or soap for washing the hair.
[0031] "Conditioner" generally refers to a formulation (e.g.,
liquid, cream, lotion, gel, semi-solid) applied to the hair to
soften the hair, smooth the hair, and/or change the sheen of the
hair.
[0032] "Reshaping" generally refers to a deformation, such as
mechanical deformation of the hair including, but not limited to
rolling, braiding, and/or twisting of the hair. Reshaping hair,
however, is not intended to refer to a deformation that results in
straightening hair or straightened hair.
[0033] "Analog" and "Derivative" are used interchangeably and refer
to a compound that possesses the same core as the parent compound,
but differs from the parent compound in bond order, the absence or
presence of one or more atoms and/or groups of atoms, and
combinations thereof. The derivative can differ from the parent
compound, for example, in one or more substituents present on the
core, which may include one or more atoms, functional groups, or
substructures. In general, a derivative can be imagined to be
formed, at least theoretically, from the parent compound via
chemical and/or physical processes.
[0034] "Electrophilic group" or "electrophilic moiety" are used
interchangeably and refer to one or more functional groups or
moieties that have an affinity for or attract electrons.
[0035] "Michael acceptor" is a species of electrophilic groups or
moieties that participates in nucleophilic addition reactions. The
Michael acceptor can be or can contain an
.alpha.,.beta.-unsaturated carbonyl-containing group or moiety,
such as a ketone. Other Michael acceptors include pi-bonds, such as
double or triple bonds conjugated to other pi-bond containing
electron withdrawing groups, such as nitro groups, nitrile groups,
and carboxylic acid groups or aryl groups.
[0036] "Alkyl" refers to the radical of saturated or unsaturated
aliphatic groups, including straight-chain alkyl, alkenyl, or
alkynyl groups, branched-chain alkyl, alkenyl, or alkynyl groups,
cycloalkyl, cycloalkenyl, or cycloalkynyl (alicyclic) groups, alkyl
substituted cycloalkyl, cycloalkenyl, or cycloalkynyl groups, and
cycloalkyl substituted alkyl, alkenyl, or alkynyl groups. Unless
otherwise indicated, a straight chain or branched chain alkyl has
30 or fewer carbon atoms in its backbone (e.g., C.sub.1-C.sub.30
for straight chain, C.sub.3-C.sub.30 for branched chain), more
preferably 20 or fewer carbon atoms, more preferably 12 or fewer
carbon atoms, and most preferably 8 or fewer carbon atoms. In some
embodiments, the chain has 1-6 carbons. Likewise, preferred
cycloalkyls have from 3-10 carbon atoms in their ring structure,
and more preferably have 5, 6 or 7 carbons in the ring structure.
The ranges provided above are inclusive of all values between the
minimum value and the maximum value.
[0037] The term "alkyl" includes both "unsubstituted alkyls" and
"substituted alkyls", the latter of which refers to alkyl moieties
having one or more substituents replacing hydrogen on one or more
carbons of the hydrocarbon backbone. Such substituents include, but
are not limited to, halogen, hydroxyl, carbonyl (such as a
carboxyl, alkoxycarbonyl, formyl, or an acyl), thiocarbonyl (such
as a thioester, a thioacetate, or a thioformate), alkoxyl,
phosphoryl, phosphate, phosphonate, a phosphinate, amino, amido,
amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio,
sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl,
aralkyl, or an aromatic or heteroaromatic moiety.
[0038] Unless the number of carbons is otherwise specified, "lower
alkyl" means an alkyl group, as defined above, but having from one
to ten carbons, more preferably from one to six carbon atoms in its
backbone structure. Likewise, "lower alkenyl" and "lower alkynyl"
have similar chain lengths. Preferred alkyl groups are lower
alkyls.
[0039] The alkyl groups may also contain one or more heteroatoms
within the carbon backbone. Examples include oxygen, nitrogen,
sulfur, and combinations thereof. In certain embodiments, the alkyl
group contains between one and four heteroatoms.
[0040] "Alkenyl" and "Alkynyl" refer to unsaturated aliphatic
groups containing one or more double or triple bonds analogous in
length (e.g., C.sub.2-C.sub.30) and possible substitution to the
alkyl groups described above.
[0041] "Aryl" refers to 5-, 6- and 7-membered aromatic rings. The
ring may be a carbocyclic, heterocyclic, fused carbocyclic, fused
heterocyclic, bicarbocyclic, or biheterocyclic ring system,
optionally substituted as described above for alkyl. Broadly
defined, "Ar", as used herein, includes 5-, 6- and 7-membered
single-ring aromatic groups that may include from zero to four
heteroatoms. Examples include, but are not limited to, benzene,
pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole,
pyrazole, pyridine, pyrazine, pyridazine, and pyrimidine. Those
aryl groups having heteroatoms in the ring structure may also be
referred to as "heteroaryl", "aryl heterocycles", or
"heteroaromatics". The aromatic ring can be substituted at one or
more ring positions with such substituents as described above, for
example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl,
cycloalkyl, hydroxyl, alkoxyl, amino, nitro, sulfhydryl, imino,
amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether,
alkylthio, sulfonyl, sulfonamido, ketone, aldehyde, ester,
heterocyclyl, aromatic or heteroaromatic moieties, --CF.sub.3, and
--CN. The term "Ar" also includes polycyclic ring systems having
two or more cyclic rings in which two or more carbons are common to
two adjoining rings (the rings are "fused rings") wherein at least
one of the rings is aromatic, e.g., the other cyclic rings can be
cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or
heterocycles, or both rings are aromatic.
[0042] "Alkylaryl" refers to an alkyl group substituted with an
aryl group (e.g., an aromatic or hetero aromatic group).
[0043] "Heterocycle" or "heterocyclic" refers to a cyclic radical
attached via a ring carbon or nitrogen of a monocyclic or bicyclic
ring containing 3-10 ring atoms, and preferably from 5-6 ring
atoms, containing carbon and one to four heteroatoms each selected
from non-peroxide oxygen, sulfur, and N(Y) wherein Y is absent or
is H, O, (C.sub.1-4) alkyl, phenyl or benzyl, and optionally
containing one or more double or triple bonds, and optionally
substituted with one or more substituents. The term "heterocycle"
also encompasses substituted and unsubstituted heteroaryl rings.
Examples of heterocyclic ring include, but are not limited to,
benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl,
benzoxazolyl, benzoxazolinyl, benzthiazolyl, benzthiazolyl,
benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl,
carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl,
cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl,
dihydrofuro[2,3-b]tetrahydrofuran, furanyl, furazanyl,
imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolenyl,
indolinyl, indolizinyl, indolyl, 3H-indolyl, isatinoyl,
isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl,
isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl,
methylenedioxyphenyl, morpholinyl, naphthyridinyl,
octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl,
1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl,
oxazolidinyl, oxazolyl, oxindolyl, pyrimidinyl, phenanthridinyl,
phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathinyl,
phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, piperidonyl,
4-piperidonyl, piperonyl, pteridinyl, purinyl, pyranyl, pyrazinyl,
pyrazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazole,
pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl,
pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl,
quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl,
tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl,
tetrazolyl, 6H-1,2,5-thiadiazinyl, 1,2,3-thiadiazolyl,
1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl,
thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl,
thienoimidazolyl, thiophenyl and xanthenyl.
[0044] "Heteroaryl" refers to a monocyclic aromatic ring containing
five or six ring atoms containing carbon and 1, 2, 3, or 4
heteroatoms each selected from non-peroxide oxygen, sulfur, and
N(Y) where Y is absent or is H, O, (C.sub.1-C.sub.8) alkyl, phenyl,
or benzyl. Non-limiting examples of heteroaryl groups include
furyl, imidazolyl, triazolyl, triazinyl, oxazoyl, isoxazoyl,
thiazolyl, isothiazoyl, pyrazolyl, pyrrolyl, pyrazinyl, tetrazolyl,
pyridyl, (or its N-oxide), thienyl, pyrimidinyl (or its N-oxide),
indolyl, isoquinolyl (or its N-oxide), quinolyl (or its N-oxide)
and the like. The term "heteroaryl" can include radicals of an
ortho-fused bicyclic heterocycle of about eight to ten ring atoms
derived therefrom, a derivative derived by fusing a propylene,
trimethylene, or tetramethylene diradical thereto. Examples of
heteroaryl include, but are not limited to, furyl, imidazolyl,
triazolyl, triazinyl, oxazoyl, isoxazoyl, thiazolyl, isothiazoyl,
pyraxolyl, pyrrolyl, pyrazinyl, tetrazolyl, pyridyl (or its
N-oxide), thientyl, pyrimidinyl (or its N-oxide), indolyl,
isoquinolyl (or its N-oxide), quinolyl (or its N-oxide), and the
like.
[0045] "Halogen" refers to fluorine, chlorine, bromine, or
iodine.
[0046] The term "substituted" refers to all permissible
substituents of the compounds described herein. In the broadest
sense, the permissible substituents include acyclic and cyclic,
branched and unbranched, carbocyclic and heterocyclic, aromatic and
nonaromatic substituents of organic compounds. Illustrative
substituents include, but are not limited to, halogens, hydroxyl
groups, or any other organic groupings containing any number of
carbon atoms, preferably 1-14 carbon atoms, and optionally include
one or more heteroatoms such as oxygen, sulfur, or nitrogen
grouping in linear, branched, or cyclic structural formats.
Representative substituents include alkyl, substituted alkyl,
alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl,
substituted phenyl, aryl, substituted aryl, heteroaryl, substituted
heteroaryl, halo, hydroxyl, alkoxy, substituted alkoxy, phenoxy,
substituted phenoxy, aroxy, substituted aroxy, alkylthio,
substituted alkylthio, phenylthio, substituted phenylthio,
arylthio, substituted arylthio, cyano, isocyano, substituted
isocyano, carbonyl, substituted carbonyl, carboxyl, substituted
carboxyl, amino, substituted amino, amido, substituted amido,
sulfonyl, substituted sulfonyl, sulfonic acid, phosphoryl,
substituted phosphoryl, phosphonyl, substituted phosphonyl,
polyaryl, substituted polyaryl, C.sub.3-C.sub.20 cyclic,
substituted C.sub.3-C.sub.20 cyclic, heterocyclic, substituted
heterocyclic, aminoacid, peptide, and polypeptide groups.
[0047] Heteroatoms, such as nitrogen, may have hydrogen
substituents and/or any permissible substituents of organic
compounds described herein that satisfy the valences of the
heteroatoms. "Substitution" or "substituted" includes the implicit
proviso that such substitution is in accordance with permitted
valence of the substituted atom and the substituent, and that the
substitution results in a stable compound (a compound that does not
spontaneously undergo transformation such as by rearrangement,
cyclization, elimination, etc.)
[0048] "Polymer" refers to a molecule containing more than 10
monomer units.
[0049] "Water-soluble" generally means at least 50, 75, 100, 125,
150, 200, 225, or 250 g is soluble in 1L of water at 25.degree.
C.
[0050] "Hydroxide-containing agents" refers to hydroxide-containing
compounds commonly used in current commercially available hair
relaxing formulations, such as lye and ammonium hydroxide. When
these hydroxide-containing compounds are present in a hair curling
formulation, the hydroxide ions produce a formulation with a high
pH, such as pH ranging from 10 to 14, preferably a pH ranging from
12 to 14.
[0051] "Lye agents" or "alkali-based agents" are used
interchangeably and these terms refer to alkali metal containing
hydroxides (e.g. sodium hydroxide and/or potassium hydroxide).
[0052] "Thiol-containing reducing agent" refers to a reducing agent
which contains at least one thiol (--SH) moiety. Exemplary thiol-
containing agents include, for example, thioglycolic acid,
thiolactic acid, thiolactic acid, thioglycerol, or
mercaptopropionic acid, or salts thereof, thioglycerin or
derivatives thereof.
[0053] "Sulfur-containing reducing agent" refers to a reducing
agent, which contains at least one sulfur (S) atom therein.
Exemplary sulfur-containing agents include, for example, the
thiol-containing agents listed above, alkali sulfites, and ammonia
sulfites, or salts or derivatives thereof.
[0054] "Peroxide-based agent," as used herein refers to an agent,
which contains at least one peroxide group. An exemplary
peroxide-based agent is hydrogen peroxide.
II. Active Agent Formulations
[0055] The active agent formulations disclosed herein are used in
methods for curling hair in combination with a hydroxide-containing
agent(s) or a formulation thereof. Additionally, the active agent
formulations, when used during the curling process/treatment can be
used to control, select, or tune the level of curl imparted to the
hair, as compared to the hair's state prior to the treatment, e.g.
its natural state. The level of curl imparted depends on the amount
of one or more active agents applied, which can be represented as a
weight ratio of the weight of one or more active agents (or the
weight of the active agent formulation) to the weight of the
hydroxide-containing formulation. Furthermore, the inclusion of one
or more active agents reduces hair breakage and damage during the
curling process.
[0056] The formulations contain one or more active agents (also
referred to herein as "compounds"), which can be combined with one
or more cosmetically acceptable carriers and/or excipients that are
considered safe and effective to apply to human hair and/or the
human scalp, and may be administered to an individual's hair
without causing undesirable biological side effects, such as
burning, itching, and/or redness, or a similar adverse
reaction.
[0057] The active agent is typically present in the formulation in
an amount ranging from about 0.05 wt % to about 25 wt % of the
formulation, such as from about 0.1 wt % to about 10 wt %, from
about 0.1 wt % to 4 wt %, or from about 0.5 wt % to 3 wt %.
Typically, the active agent may be present in the formulation in an
amount ranging from about 0.5 wt % to about 5 wt % of the
formulation.
[0058] The active agent is stable in aqueous solution for a period
of at least 2, 3, 4, 5, 6, 8, 9, 10, 11, or 12 months or longer at
pH of 3 to 8, preferably at a pH of 3 to 5, and at a temperature of
about 25-30.degree. C., preferably about 25.degree. C. "Stable" as
used herein with respect to shelf-life means that at least 40, 45,
50, 55, 60, 65, 70, 75, 80, 85, 90, or 95% of the active agent(s)
is unchanged over the specified time period.
[0059] The active agent formulation generally does not contain a
strong base, such as a nitrogen containing base (e.g. guanadine,
amidine, or a derivative thereof).
[0060] A. Active Agent
[0061] The active agent contains at least one reactive moiety
capable of reacting with and forming bonds with a nucleophile, such
as a thiol or amine The active agent optionally contains a linker
group. The active agent can contain one or more acidic groups, such
as carboxylic acids, sulfonic acids, phosphonic acids.
[0062] Without being bound by theory, it is believed that the
reactive moieties, upon reaction with nucleophiles, such as thiol
groups, on the hair follicle, form bonds that are stable, for
example, hydrolytically stable. "Stable", as used in reference to
the bonds formed in the hair follicles means the bonds remain
intact for at least one week, two weeks, three weeks, four weeks,
one month, or two months or longer when exposed to water at a pH of
3 to 8, preferably at a pH of 3 to 5, at a temperature from about
5.degree. C. to about 100.degree. C., from about 20.degree. C. to
about 75.degree. C., more preferably from about 20.degree. C. to
about 50.degree. C., from about 25.degree. C. to about 40.degree.
C., or from about 25.degree. C. to about 30.degree. C., and more
preferably at a temperature of about 25.degree. C.
[0063] It is preferred that the reaction between the reactive
moieties and thiols occur around room temperature, for example,
from about 15.degree. C. to about 35.degree. C., preferably from
about 20.degree. C. to about 30.degree. C., more preferably from
about 22.degree. C. to about 27.degree. C.
1. Active Agents Defined by Formula I
[0064] In some embodiments, the active agents have a structure
according to Formula I:
##STR00001##
[0065] wherein
[0066] A, B, C, and D are reactive moieties containing one or more
charges,
[0067] R is a linker that contains two or more charges, wherein the
charges are opposite to the charges on the reactive moieties,
wherein n=1-100, preferably n=1-10, more preferably n=1; and each
occurrence of p, q, r, and s is independently an integer from 0 to
25, preferably from 0 to 10, more preferably from 0 to 2. The sum
of p+q+r+s is equal to or greater than 2.
[0068] The reactive moieties may be present on any atom of the
linker. In some embodiments, the reactive moieties are the same. In
some embodiments, one or more of the reactive moieties is
different.
[0069] In some embodiments, the reactive moieties are negatively
charged and the linker has positively charged moieties. In other
embodiments, the reactive moieties are positively charged and the
linker has negatively charged moieties. Generally, the sum of the
charges on the active agent of Formula I is zero, although
stoichiometric imbalances may exist.
[0070] The reactive moieties on the active agents of Formula I are
preferably linked via a linker R. The linker R, as used herein,
refers to one or more polyfunctional, e.g. bifunctional molecules,
trifunctional molecules, tetrafunctional molecules, etc., which can
be used to ionically bind the two or more reactive moieties and
which do not interfere with the reactive properties of the active
agents. The reactive moieties may be attached to any part of linker
R.
a. Linker R
[0071] In a preferred embodiment, in Formula I, n=1 and the linker
R is not a polymer. The linker R can be a single atom, such as a
heteroatom (e.g., O or S), a group of atoms, such as a functional
group (e.g., amine, --C(.dbd.O)--, --CH.sub.2--), or multiple
groups of atoms, such as an alkylene chain. Suitable linkers
include but are not limited to oxygen, sulfur, carbon, boron,
nitrogen, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl,
heterocycloalkyl, heteroaryl, ether, amine, and an oligomer.
[0072] The linker R is optionally independently substituted with
one or more substituents including hydrogen, halogen, cyano,
alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl,
heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl,
carboxylic acid (--COOH), --C(O)R.sup.1, --C(O)OR.sup.1,
carboxylate (--COO.sup.-), primary amide (e.g., --CONH.sub.2),
secondary amide, --C(O)NR.sup.1R.sup.2, --NR.sup.1R.sup.2,
--NR.sup.1S(O).sub.2R.sup.2, --NR.sup.1C(O)R.sup.2,
--S(O).sub.2R.sup.2 , --SR.sup.1, and --S(O).sub.2NR.sup.1R.sup.2,
sulfinyl group (e.g., --SOR.sup.1), and sulfonyl group (e.g.,
--SOOR.sup.1); wherein R.sup.1 and R.sup.2 may each independently
be hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl,
heterocycloalkyl and heteroaryl; wherein each of R.sup.1 and
R.sup.2 is optionally independently substituted with one or more
substituents selected from the group consisting of halogen,
hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl
optionally substituted with one or more halogen or alkoxy or
aryloxy, aryl optionally substituted with one or more halogen or
alkoxy or alkyl or trihaloalkyl, heterocycloalkyl optionally
substituted with aryl or heteroaryl or .dbd.O, or alkyl optionally
substituted with hydroxyl, cycloalkyl optionally substituted with
hydroxyl, heteroaryl optionally substituted with one or more
halogen or alkoxy or alkyl or trihaloalkyl, haloalkyl,
hydroxyalkyl, carboxy, alkoxy, aryloxy, alkoxycarbonyl,
aminocarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl.
[0073] In some embodiments, the linker R may be an alkoxy, ether,
alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl,
heteroaryl, or amine.
b. Active Agents According to Formula I
[0074] The active agent according to Formula I contains at least
two reactive moieties that are capable of reacting with a
nucleophile, such as a thiol or amine, to form covalent bonds. For
example, the reactive moieties are capable of reacting with a thiol
group in the hair to form a stable covalent bond. The reactive
moiety is typically an electrophilic moiety capable of forming a
salt with the linker. Alternately, the reactive moiety can be
capable of reacting with a free radical.
[0075] The active agent according to Formula I contains at least
two reactive moieties. However, the active agent may contain three,
four, five, six, or greater than six reactive moieties.
[0076] The reaction between the reactive moiety and the thiol
groups may be initiated at room temperature and pressure when the
reactive moiety contacts a thiol group in the hair. In some
embodiments, the reaction may require an initiator, such as heat,
catalyst, basic conditions, or a free radical initiator. The rate
of reaction between the reactive moiety and the thiol may be
increased by changes in temperature, pH, and/or addition of one or
more excipients, such as a catalyst; however, this is generally not
required.
[0077] The two or more reactive moieties on the active agent can be
the same. In some embodiments, the two or more reactive moieties
are different.
[0078] In some embodiments, the reactive moieties are capable of
undergoing a conjugate additional reaction. The reactive moieties
can independently be or contain a Michael acceptor, a
succinimidyl-containing group, a maleimido-containing group,
azlactone, a benzoxazinone derivative, vinyl sulfone, vinyl
sulfoximine, vinyl sulfonate, vinyl phosphonate, benzoxazinone,
isocyanate, epoxide, an electrophilic moiety containing a leaving
group, an electrophilic thiol acceptor, acrylic or acrylate group,
a methacrylic or methacrylate group, a styrene group, an acryl
amide group, a methacryl amide group, a maleate group, a fumarate
group, an itaconate group, a vinyl ether group, an allyl ether
group, an allyl ester group, a vinyl ester group, a sulfonate
group, a phosphonate group, a sulfoxide group, a sulfonamide group,
a sulfinimide group, a sulfinamide group, a sulfonimidate group, or
a sulfonimidamide group.
[0079] In the preferred embodiments, each of reactive moieties A,
B, C, and/or D when present independently contains a moiety
selected from the group consisting of a vinyl sulfone, an acrylate
group, a methacrylate group, a styrene group, an acryl amide group,
a methacryl amide group, a maleate group, a fumarate group, and an
itaconate group. Further, in the preferred embodiments, n=1 and the
linker R is not a polymer. Optionally, all of the reactive moieties
are the same. For example, in some embodiments all of the reactive
moieties are maleate groups.
[0080] In some embodiments, the active agent according to Formula I
has one of the following structures:
##STR00002##
[0081] Active agents according to Formula I are further described
in U.S. Pat. No. 9,095,518, which is incorporated herein by
reference with respect to its disclosure of active agents.
2. Active Agents Defined by Formula II
[0082] In some other embodiments, the active agent is a
polyfunctional compound that contains ionizable functional groups
capable of forming ionic bonds and functional groups capable of
forming a covalent bond with a nucleophile, such as a thiol or an
amine.
[0083] The active agent may have the following Formula II:
(B).sub.m--Z--(A).sub.n Formula II
wherein Z is a linker or is absent, m and n are each an integer
independently selected from 1-6, provided that m+n is at least 2, B
is a functional group capable of forming a covalent bond with a
nucleophile, such as a thiol or amine group, and A is an ionizable
functional group. Preferably, the linker Z is not a polymer.
Optionally, the active agent is a simple salt of Formula II.
[0084] Suitable ionizable functional groups (group A) include, but
are not limited to, acidic groups such as carboxylic acids,
sulfonic acids, phosphonic acids, and basic groups, such as
amines
[0085] Suitable functional groups capable of forming a covalent
bond with a nucleophile, such as a thiol or an amine, (group B)
include, but are not limited to, Michael acceptors, alkyl halides
or sulfonate esters. Exemplary active agents according to Formula
II may contain thiol reactive functional groups, as group B, for
example, such as those shown in the following moieties:
##STR00003##
wherein R is independently selected from hydrogen, C.sub.1-6 alkyl,
aryl, or an ionizable functional group; Z' is oxygen (O), NH, or is
absent; and G is carbon (C) and g is 1, or G is sulfur (S) and g is
2. In preferred embodiments, Z is a linker or is absent, the linker
is not a polymer, and group B is a functional group capable of
forming a covalent bond with a thiol or amine group and group B is
independently selected from the group consisting of:
##STR00004##
wherein R, Z', G, and g are as previously defined.
a. Linker Z of Formula II
[0086] The linker Z, when present, can be or can contain an alkyl,
alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl or
heteroaryl group. One or more of the carbon atoms in the alkyl,
alkenyl, cycloalkyl, cycloalkenyl, and aryl groups can be
substituted with a heteroatom, yielding, for instance, an ether or
alkylamine-containing linker.
[0087] The linker Z may be substituted with one or more
substituents, which may be the same or different, including
hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl,
cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy,
oxo, formyl, acyl, carboxylic acid (--COOH), --C(O)R.sup.1,
--C(O)OR.sup.1, carboxylate (--COO-), primary amide (e.g.,
--CONH.sub.2), secondary amide, --C(O)NR.sup.1R.sup.2,
--NR.sup.1R.sup.2, --NR.sup.1S(O).sub.2R.sup.2,
--NR.sup.1C(O)R.sup.2, --S(O).sub.2R.sup.2 , --SR.sup.1, and
--S(O).sub.2NR.sup.1R.sup.2, sulfinyl group (e.g., --SOR.sup.1),
and sulfonyl group (e.g., --SOOR.sup.1); wherein R.sup.1 and
R.sup.2 may each independently be hydrogen, alkyl, alkenyl,
alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl; wherein
each of R.sup.1 and R.sup.2 is optionally independently substituted
with one or more substituents selected from the group consisting of
halogen, hydroxyl, oxo, cyano, nitro, amino, alkylamino,
dialkylamino, alkyl optionally substituted with one or more halogen
or alkoxy or aryloxy, aryl optionally substituted with one or more
halogen or alkoxy or alkyl or trihaloalkyl, heterocycloalkyl
optionally substituted with aryl or heteroaryl or oxo, or alkyl
optionally substituted with hydroxyl, cycloalkyl optionally
substituted with hydroxyl, heteroaryl optionally substituted with
one or more halogen or alkoxy or alkyl or trihaloalkyl, haloalkyl,
hydroxyalkyl, carboxy, alkoxy, aryloxy, alkoxycarbonyl,
aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.
[0088] In certain preferred embodiments, the linker Z is a
C.sub.1-10 alkyl group which may be unsubstituted or substituted
one or more times by oxo, hydroxyl, carboxyl, amido or amino
Preferably, the linker Z is a C.sub.1-4 alkyl group. The alkyl
group may be linear or branched. The alkyl group may also be
interrupted one or more times by a heteroatom selected from oxygen,
sulfur and nitrogen. An example of such a di-carboxylic acids
having a heteroatom interruption is thiodipropionic acid. In other
embodiments, the alkyl group may contain one or more double or
triple bonds.
[0089] In some embodiments, the active agent according to Formula
II has one of the following structures:
##STR00005##
or is a simple salt of any of these structures.
[0090] In some embodiments, the active agent can be maleic acid,
acrylic acid, methyl acrylic acid, or vinyl sulfonic acid; or a
simple salt of any of these acids.
[0091] The term "simple salt," as used herein, refers to a salt
formed from the ionized form of an active agent of Formula II with
a counterion group having a charge opposite to the charge of the
ionizable functional group A. In preferred embodiments, a simple
salt includes only one active agent and one counterion group (such
as, for example, sodium maleate, sodium acrylate, sodium
methylmethacrylate, or sodium vinylsulfonate). The counterion group
can be a suitable ionized metal or an optionally substituted
C.sub.1-C.sub.10, C.sub.1-C.sub.8, or C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.10, C.sub.2-C.sub.8, or C.sub.2-C.sub.6 alkenyl, or
C.sub.2-C.sub.10, C.sub.2-C.sub.8, or C.sub.2-C.sub.6 alkynyl
counterion group covalently bound to an ionic moiety. For example,
if the ionizable functional group A has a negative charge (e.g.,
--C(O)O.sup.-), then the counterion group has a positive charge
(e.g. aminium group). The C.sub.1-C.sub.10, C.sub.1-C.sub.8, or
C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.10, C.sub.2-C.sub.8, or
C.sub.2-C.sub.6 alkenyl, or C.sub.2-C.sub.10, C.sub.2-C.sub.8, or
C.sub.2-C.sub.6 alkynyl counterion groups may be substituted one or
more times by substituents as defined above with respect to linker
Z. Optionally substituted C.sub.3-C.sub.10, C.sub.3-C.sub.8, or
C.sub.3-C.sub.6 alkyl counterion groups may be linear, branched, or
cyclic. The C.sub.1-C.sub.10, C.sub.I-C.sub.8, or C.sub.1-C.sub.6
alkyl, C.sub.2-C.sub.10, C.sub.2-C.sub.8, or C.sub.2-C.sub.6
alkenyl, or C.sub.2-C.sub.10, C.sub.2-C.sub.8, or C.sub.2-C.sub.6
alkynyl counterion groups may also be interrupted one or more times
along the backbone by a heteroatom selected from oxygen, sulfur,
and/or nitrogen. In certain embodiments, the counterion groups do
not contain a carbon-carbon double bond. In certain other
embodiments, the counterion groups have a molecular weight of less
than about 200 g/mol, 150 g/mol, 125 g/mol, 100 g/mol, 100 g/mol,
90 g/mol, 80 g/mol, 70 g/mol, 60 g/mol, 50 g/mol, 40 g/mol, 30
g/mol, or 20 g/mol.
[0092] Exemplary counterion groups include, but are not limited to,
sodium ion, potassium ion, ethanolammonium, and allylammonium.
3. Active Agents Defined by Formula III
[0093] In certain embodiments, when the active agent of Formula II
is a simple salt it can have a structure according to Formula
III:
(B).sub.m--Z--(A).sub.n--(C).sub.o Formula III
wherein Z is a linker or is absent, m and n are each an integer
independently selected from 1-6, provided that m+n is at least 2, B
is a functional group capable of forming a covalent bond with a
nucleophile, such as a thiol or amine group, A is an ionizable
functional group as defined above, and C is an ionic group which is
also capable of forming a covalent bond with a thiol and which has
a charge opposite to that of ionizable group A. Group C is
ionically bonded (denoted by dashed line) to group A. For ionic
group C, o is an integer value independently selected from 1-6,
such that the sum of charges of group C and ionizable group A is
zero. Preferably, linker Z is not a polymer.
[0094] In active agents of Formula III, group C is an ionic group,
which is ionically bonded to ionizable group A and is capable of
forming a covalent bond with a thiol. Group C may be a Michael
acceptor, a succinimidyl-containing group, a maleimido-containing
group, azlactone, a benzoxazinone derivative, vinyl sulfone, vinyl
sulfoximine, vinyl sulfonate, vinyl phosphonate, benzoxazinone,
isocyanate, epoxide, an electrophilic moiety containing a leaving
group, an electrophilic thiol acceptor, acrylic or acrylate group,
a methacrylic or methacrylate group, a styrene group, an acryl
amide group, a methacryl amide group, a maleate group, a fumarate
group, an itaconate group, a vinyl ether group, an allyl ether
group, an allyl ester group, a vinyl ester group, a sulfonate
group, a phosphonate group, a sulfoxide group, a sulfonamide group,
a sulfinimide group, a sulfinamide group, a sulfonimidate group, or
a sulfonimidamide group. By way of example, group C can be an
allylammonium or 2-(methacrylolyoxy)ethan-1-ammonium.
[0095] The active agents according to Formula III may contain thiol
reactive functional groups which react with a nucleophile, such as
a thiol, as group B. Examplary thiol reactive functional groups
include, but are not limited, to those shown in the following
moieties:
##STR00006##
wherein R is independently selected from hydrogen, C.sub.1-6 alkyl,
aryl, or an ionizable functional group; Z' is oxygen (O), NH, or is
absent; and G is carbon (C) and g is 1, or G is sulfur (S) and g is
2. In preferred embodiments, Z is a linker or is absent, the linker
is not a polymer, and group B is a functional group capable of
forming a covalent bond with a thiol or amine group and group B is
independently selected from the group consisting of:
##STR00007##
wherein R, Z', G, and g are as previously defined.
a. Linker Z of Formula III
[0096] The linker Z, when present, can be or can contain an alkyl,
alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl or
heteroaryl group. One or more of the carbon atoms in the alkyl,
alkenyl, cycloalkyl, cycloalkenyl, and aryl groups can be
substituted with a heteroatom, yielding, for instance, an ether or
alkylamine-containing linker.
[0097] The linker Z may optionally be substituted with one or more
substituents, which may be the same or different, including
hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl,
cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy,
oxo, formyl, acyl, carboxylic acid (--COOH), --C(O)R.sup.1,
--C(O)OR.sup.1, carboxylate (--COO--), primary amide (e.g.,
--CONH.sub.2), secondary amide, --C(O)NR.sup.1R.sup.2,
--NR.sup.1R.sup.2, --NR.sup.1S(O).sub.2R.sup.2,
--NR.sup.1C(O)R.sup.2, --S(O).sub.2R.sup.2, --SR.sup.1, and
--S(O).sub.2NR.sup.1R.sup.2, sulfinyl group (e.g., --SOR.sup.1),
and sulfonyl group (e.g., --SOOR.sup.1); wherein R.sup.1 and
R.sup.2 may each independently be hydrogen, alkyl, alkenyl,
alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl; wherein
each of R.sup.1 and R.sup.2 is optionally independently substituted
with one or more substituents selected from the group consisting of
halogen, hydroxyl, oxo, cyano, nitro, amino, alkylamino,
dialkylamino, alkyl optionally substituted with one or more halogen
or alkoxy or aryloxy, aryl optionally substituted with one or more
halogen or alkoxy or alkyl or trihaloalkyl, heterocycloalkyl
optionally substituted with aryl or heteroaryl or oxo or alkyl
optionally substituted with hydroxyl, cycloalkyl optionally
substituted with hydroxyl, heteroaryl optionally substituted with
one or more halogen or alkoxy or alkyl or trihaloalkyl, haloalkyl,
hydroxyalkyl, carboxy, alkoxy, aryloxy, alkoxycarbonyl,
aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.
[0098] In certain preferred embodiments, the linker Z is a
C.sub.1-10 alkyl group which may be unsubstituted or substituted
one or more times by oxo, hydroxyl, carboxyl, amido or amino
Preferably, the linker Z is a C.sub.1-4 alkyl group. The alkyl
group may be linear or branched. The alkyl group may also be
interrupted one or more times by a heteroatom selected from oxygen,
sulfur and nitrogen. An example of such a di-carboxylic acids
having a heteroatom interruption is thiodipropionic acid. In other
embodiments, the alkyl group may contain one or more double or
triple bonds.
[0099] In some embodiments, the active agent of Formula III has one
of the following structures:
##STR00008##
[0100] B. Excipients
[0101] Active agent formulations typically contain one or more
cosmetically acceptable excipients. Cosmetically acceptable
excipients include, but are not limited to, water, diluents,
preservatives, antioxidants, chelating agents, sunscreen agents,
vitamins, dyes, hair coloring agents, proteins, amino acids,
natural extracts such as plant extracts, humectants, fragrances,
perfumes, oils, emollients, lubricants, butters, penetrants,
thickeners, viscosity modifiers, polymers, resins, hair fixatives,
film formers, surfactants, detergents, emulsifiers, opacifying
agents, volatiles, propellants, liquid vehicles, carriers, salts,
pH adjusting agents (e.g., citric acid), neutralizing agents,
buffers, hair conditioning agents, anti-static agents, anti-frizz
agents, anti-dandruff agents, absorbents, and combinations
thereof.
[0102] In certain embodiments, the active agent formulations are
free of thickeners or substantially free of thickeners (i.e.
viscosity increasing agents).
[0103] The formulations may contain one or more cosmetically
acceptable excipients. In some forms, the formulations contain the
active agent, water, and optionally a preservative and/or
fragrance.
[0104] The formulation for curling hair during or immediately
following application of a hydroxide-containing formulation may be
in any suitable physical form. Suitable forms include, but are not
limited to low to moderate viscosity liquids, lotions, milks,
mousses, sprays, gels, creams, shampoos, conditioners, and the
like. Suitable excipients, such as those listed above, are
included, or excluded, from the formulation depending on the form
of the formulation (e.g., liquid, hair spray, cream).
[0105] The one or more cosmetically acceptable excipients are
typically present in an amount ranging from about 10 wt % to about
99.99 wt % of the formulation, preferably about 40 wt % to about 99
wt %, more preferably from about 80 wt % to about to about 99 wt
%.
1. Surfactants
[0106] Surfactants are surface-active agents that are able to
reduce the surface tension of water and cause the formulation to
slip across or onto the hair. Surfactants can also be detergents or
soap. The surfactants may be amphoteric, anionic, or cationic.
Suitable surfactants that may be used in the formulation include,
but are not limited to, 3-aminopropane sulfonic acid, almond amide,
almond amidopropyl betaine, almond amidopropylamine oxide, aluminum
hydrogenated tallow glutamate, aluminum lanolate, aminoethyl
sulfate, aminopropyl lauryl glutamine, ammonium C.sub.12-15 alkyl
sulfate, ammonium C.sub.12-15 pareth sulfate, ammonium C.sub.12-16
alkyl sulfate, ammonium C.sub.9-10 perfluoroalkylsulfonate,
ammonium capryleth sulfate, ammonium capryleth-3 sulfate, ammonium
monoglyceride sulfate, ammonium sulfate, ammonium isothionate,
ammonium cocoyl sarcosinate, ammonium cumene sulfonate, ammonium
dimethicone copolyol sulfate, ammonium dodecylbenzenesulfonate,
ammonium isostearate, ammonium laureth sulfate, ammonium laureth-12
sulfate, ammonium laureth-5 sulfate, ammonium laureth-6
carboxylate, ammonium laureth-7 sulfate, ammonium laureth-8
carboxylate, ammonium laureth-9 sulfate, ammonium lauroyl
sarcosinate, ammonium lauryl sulfate, ammonium lauryl
sulfosuccinate, ammonium myreth sulfate, ammonium myristyl sulfate,
ammonium nonoxynol-30 sulfate, ammonium nonoxynol-4 sulfate,
ammonium oleate, ammonium palm kernel sulfate, ammonium
polyacrylate, ammonium stearate, ammonium tallate, ammonium xylene
sulfonate, ammonium xylene sulfonate, amp-isostearoyl
gelatin/keratin amino acids/lysine hydroxypropyltrimonium chloride,
amp-isostearoyl hydrolyzed collagen, apricot kernel oil PEG-6
esters, apricot amide, apricot amidopropyl betaine, arachideth-20,
avocadamide, avocadamidopropyl betaine, babassuamide,
babassuamidopropyl betaine, babassuamidopropylamine oxide,
behenalkonium chloride, behenamide, behenamide, behenamidopropyl
betaine, behenamine oxide, sodium laureth sulfate, sodium lauryl
sulfate, a polyoxyether of lauryl alcohol or ceteareth-20, or
combinations thereof.
[0107] Suitable anionic surfactants include, but are not limited
to, those containing carboxylate, sulfonate, and sulfate ions.
Examples of anionic surfactants include sodium, potassium, ammonium
of long chain alkyl sulfonates and alkyl aryl sulfonates such as
sodium dodecylbenzene sulfonate; dialkyl sodium sulfosuccinates,
such as sodium dodecylbenzene sulfonate; dialkyl sodium
sulfosuccinates, such as sodium
bis-(2-ethylthioxyl)-sulfosuccinate; and alkyl sulfates such as
sodium lauryl sulfate. Cationic surfactants include, but are not
limited to, quaternary ammonium compounds such as benzalkonium
chloride, benzethonium chloride, cetrimonium bromide, stearyl
dimethylbenzyl ammonium chloride, polyoxyethylene and coconut
amine. Examples of nonionic surfactants include ethylene glycol
monostearate, propylene glycol myristate, glyceryl monostearate,
glyceryl stearate, polyglyceryl-4-oleate, sorbitan acylate, sucrose
acylate, PEG-150 laurate, PEG-400 monolaurate, polyoxyethylene
monolaurate, polysorbates, polyoxyethylene octylphenylether,
PEG-1000 cetyl ether, polyoxyethylene tridecyl ether, polypropylene
glycol butyl ether, Poloxamer.RTM. 401, stearoyl
monoisopropanolamide, and polyoxyethylene hydrogenated tallow
amide. Examples of amphoteric surfactants include sodium
N-dodecyl-.beta.-alanine, sodium N-lauryl-.beta.-iminodipropionate,
myristoamphoacetate, lauryl betaine and lauryl sulfobetaine.
[0108] More than one surfactant may be included in the
formulation.
[0109] The surfactants are optionally included in an amount ranging
from about 0.1% to about 15% by weight of the formulation,
preferably about 1% to about 10% by weight of the formulation.
2. Emollients
[0110] Emollient refers to a material that protects against wetness
or irritation, softens, soothes, coats, lubricates, moisturizes,
protects, and/or cleanses the skin. Suitable emollients for use in
the formulations include, but are not limited to a silicone
compound (e.g., dimethicone, cyclomethicone, dimethicone copolyol
or a mixture of cyclopentasiloxane and dimethicone/vinyldimethicone
cross polymer, cyclopentasiloxane polysilicone), polyols such as
sorbitol, glycerin, propylene glycol, ethylene glycol, polyethylene
glycol, caprylyl glycol, polypropylene glycol, 1,3-butane diol,
hexylene glycol, isoprene glycol, xylitol; ethylhexyl palmitate; a
triglyceride such as caprylic/capric triglyceride and fatty acid
ester such as cetearyl isononanoate or cetyl palmitate. In a
specific embodiment, the emollient is dimethicone,
amidodimethicone, dimethiconol, cyclopentasiloxane, potassium
dimethicone PEG-7 panthenyl phosphate, or a combination thereof.
More than one emollient may be included in the formulation.
[0111] The emollient is optionally included in an amount ranging
from about 0.5% to about 15% by weight of the formulation,
preferably from about 1% to about 10% by weight of the
formulation.
3. Emulsifiers
[0112] The formulations may also contain one or more emulsifiers.
Suitable emulsifiers include, but are not limited to, copolymers of
an unsaturated ester and styrene sulfonate monomer, cetearyl
alcohol, glyceryl ester, polyoxyethylene glycol ether of cetearyl
alcohol, stearic acid, polysorbate-20, ceteareth-20, lecithin,
glycol stearate, polysorbate-60, or polysorbate-80, or combinations
thereof. More than one emulsifier may be included in the
formulation.
[0113] The emulsifier is optionally included in an amount ranging
from about 0.05% to about 15% by weight of the formulation,
preferably from about 0.1% to about 10% by weight of the
formulation.
4. Preservatives
[0114] One or more preservatives may be included in the
formulations to prevent microbial growth in the formulations.
Suitable preservatives include, but are not limited to, glycerin
containing compounds (e.g., glycerin or ethylhexylglycerin or
phenoxyethanol), benzyl alcohol, parabens (methylparaben,
ethylparaben, propylparaben, butylparaben, isobutylparaben, etc.),
sodium benzoate, ethylenediamine-tetraacetic acid (EDTA), potassium
sorbate, and/or grapefruit seed extract, or combinations thereof.
More than one preservative may be included in the formulation.
Other preservatives are known in the cosmetics industries and
include salicylic acid, DMDM Hydantoin, Formaldehyde, Chlorphenism,
Triclosan, Imidazolidinyl Urea, Diazolidinyl Urea, Sorbic Acid,
Methylisothiazolinone, Sodium Dehydroacetate, Dehydroacetic Acid,
Quaternium-15, Stearalkonium Chloride, Zinc Pyrithione, Sodium
Metabisulfite, 2-Bromo-2-Nitropropane, Chlorhexidine Digluconate,
Polyaminopropyl biguanide, Benzalkonium Chloride, Sodium Sulfite,
Sodium Salicylate, Citric Acid, Neem Oil, Essential Oils (various),
Lactic Acid, and Vitamin E (tocopherol).
[0115] The preservative is optionally included in an amount ranging
from about 0.1% to about 5% by weight of the formulation,
preferably from about 0.3% to about 3% by weight of the
formulation. Preferably, the formulations are paraben free.
5. Conditioning Agents
[0116] One or more conditioning agents may be included in the
formulations. Suitable conditioning agents include, but are not
limited to, silicone-based agents (e.g., silicone quaternium-8),
panthenol, hydrolyzed wheat and/or soy protein, amino acids (e.g.
wheat amino acids), rice bran wax, meadowfoam seed oil, mango seed
oil, grape seed oil, jojoba seed oil, sweet almond oil,
hydroxyethyl behenamidopropyl dimonium chloride, aloe leaf extract,
aloe barbadensis leaf juice, phytantriol, panthenol, retinyl
palmitate, behentrimonium methosulfate, cyclopentasiloxane,
quaternium-91, stearamidopropyl dimethylamine, and combinations
thereof.
[0117] The conditioning agent(s) is optionally included in an
amount ranging from about 0.01% to about 5% by weight of the
formulation, preferably from about 0.05% to about 3% by weight of
the formulation.
6. Diluents
[0118] Diluent, as used herein, refers to a substance(s) that
dilutes the active agent. Water is the preferred diluent. The
formulations typically contains greater than one percent (wt)
water, preferably greater than five percent (wt) water, more
preferably greater than 50% (wt) water, and most preferably greater
than 80% (wt)water. Alcohols, such as ethyl alcohol and isopropyl
alcohol, may be used at low concentrations (about 0.5% by weight of
the formulation) to enhance hair or skin penetration and/or reduce
odor.
7. Viscosity Modifying Agents
[0119] The formulations described herein are preferably low
viscosity formulations having flow properties of readily flowing
liquids at standard temperature and pressure, such as similar to
the properties of water or milk. Optionally, the viscosity of the
combined formulation is more viscous but still flowable at standard
temperature and pressure, such as a viscosity similar to
shampoo.
[0120] The formulations optionally contain one or more viscosity
modifying agents.
[0121] In certain embodiments, the active agent formulations and/or
combined formulations are free of thickeners or substantially free
of thickeners (i.e. viscosity increasing agents). For example, an
active agent formulation and/or combined formulation that is
substantially free of thickeners may contain one or more thickeners
in an amount that does not increase the viscosity for the
formulation compared to the same formulation in the absence of the
thickeners. An active agent formulation and/or combined formulation
that is substantially free of thickeners may contain less than
about 5 wt %, 4 wt %, 3 wt %, 2 wt %, or 1 wt % of one or more
thickeners present in the formulation. In certain embodiments, the
active agent formulations and/or combined formulations have less
than about 1 wt % of one or more thickeners present, such as less
than about 0.9 wt %, less than about 0.8 wt %, less than about 0.7
wt %, less than about 0.6 wt %, less than about 0.5 wt %, less than
about 0.4 wt %, less than about 0.3 wt %, less than about 0.2 wt %,
or less than about 0.1 wt % of one or more thickeners in the
formulation. Classes of thickeners include, but are not limited to,
viscous liquids, such as polyethylene glycol, semisynthetic
polymers, such as semisynthetic cellulose derivatives, synthetic
polymers, such as carbomers, poloxamers, and polyethyleneimines
(e.g., PEI-10), naturally occurring polymers, such as acacia,
tragacanth, alginates (e.g., sodium alginate), carrageenan,
alcohols, such as cetyl alcohol, vegetable gums, such as xanthan
gum, petroleum jelly, waxes, particulate associate colloids, such
as bentonite, colloidal silicon dioxide, and microcrystalline
cellulose, surfactants, such as PPG-2 hydroxyethyl
coco/isostearamide, emulsifiers, such as disteareth-75 IPDI, and
salts, such as sodium chloride, and combinations thereof.
8. Antioxidants
[0122] The formulations may contain one or more antioxidants.
Examples include, but are not limited to, tocopheryls, BHT,
ascorbic acid, camellia sinensis leaf extract, ascorbyl palmitate,
magnesium ascorbyl phosphate, carotenoids, resveratrol, triethyl
citrate, arbutin, kojic acid, tetrahexydecyl ascorbate, superoxide
dismutase, zinc, sodium metabisulfite, lycopene, ubiquinone, and
combinations thereof.
9. Opacifying Agents
[0123] The formulations may contain one or more opacifying agents.
Opacifying agents are added to the formulations to make them
opaque. Suitable opacifying agents include, but are not limited to,
glycol distearate and ethoxylated fatty alcohols.
[0124] C. Properties of the Active Agent Formulations
1. Creams
[0125] In certain embodiments, the active agent formulation may be
in the form of a cream. The cream typically includes the active
agent of Formulae I, II, or III in a suitable carrier. The cream
may contain combinations of the active agents. The active agent may
be included in any suitable concentration. Typical concentrations
of the active agent in the cream range from small amounts such as
approximately 0.05 wt % to about 25 wt % of the formulation, such
as from about 0.1 wt % to about 10 wt %, from about 0.1 wt % to 4
wt %, or from about 0.5 wt % to 3 wt %. Typically, the active agent
may be present in the formulation in an amount ranging from about
0.5 wt % to about 5 wt % of the formulation. Preferably, the cream
contains the active agent in a concentration ranging from 0.1% (wt)
to 5% (wt), more preferably from 0.1% wt to 3% (wt). While greater
concentrations of active agent could be present in the cream, they
are generally not needed to achieve the desired results.
[0126] Additionally, the cream may include an oil, a
hair-conditioning agent, and/or a thickener. The cream may also
include a fragrance, a plant extract, and/or a surfactant. The
cream may be packaged in a tube, tub, bottle, or other suitable
container.
[0127] When the active agent formulation in the form of a cream is
combined with a hydroxide-containing agent formulation (e.g. mixed
to form a combined formulation or applied simultaneously to the
hair), a precipitate containing a metal ion is typically not
formed. Preferably, a combined formulation in the form of a cream
does not contain a precipitate containing a metal ion.
2. Liquid Active Agent Formulations
[0128] In some embodiments, liquid active agent-containing
formulations are provided, which are mixed at the time of use with
a second formulation containing hydroxide-containing agents to
provide a combined formulation for curling hair. In these
embodiments, the liquid active agent formulation may contain any
suitable concentration of active agent in a suitable carrier,
typically a diluent, such as described above. The liquid active
agent formulation may contain combinations of the active agents.
The concentration of the active agent is suitable to provide a
combined formulation with the appropriate final volume and final
concentration of active agent, as desired.
[0129] For example, a liquid active agent formulation can contain a
concentration of active agent ranging from about 0.05 wt % to about
25 wt % of the formulation, such as from about 0.1 wt % to about 10
wt %, from about 0.1 wt % to 4 wt %, or from about 0.5 wt % to 3 wt
%. Typically, the active agent may be present in the formulation in
an amount ranging from about 0.5 wt % to about 5 wt % of the
formulation. In a preferred embodiment, the liquid active agent
formulation contains about 5% (wt) to 20% (wt) active agent.
Preferably, the active agent-containing formulation is
odorless.
a. Concentration of Active Agent
[0130] In some embodiments, a first active agent formulation, which
may contain one or more active agents according to Formulae I, II,
and/or III, is provided, which typically contains about 0.1 to
about 50 wt % of one or more of the active agents described herein.
The active agent formulation may contain from about 0.1 to about 30
wt %, from about 0.1 to about 20 wt %, from about 0.1 to about 10
wt %, from about 0.1 to about 10 wt %, or from about 0.5 to 5 wt %
of one or more of the active agents described herein. The active
agent formulations are typically in an aqueous solution and
optionally include other suitable ingredients and/or excipients.
The active agent formulations are preferably liquid active agent
formulations. In some embodiments, the active agent formulations
are preferably not in the form of a cream. The active agent
formulations can be mixed with a hydroxide-containing agent
formulation to form a combined formulation as described below.
[0131] In some embodiments, such as when the active agent is
Bis-aminopropyl diglycol dimaleate, the active agent formulation
may contain from about 0.1 to about 30 wt %, from about 0.1 to
about 20 wt %, from about 0.1 to about 10 wt %, from about 0.1 to
about 10 wt %, or from about 0.5 to 5 wt % of Bis-aminopropyl
diglycol dimaleate. Optionally, the active agent formulation
contains about from about 0.5 to about 10 wt %, from about 1 to
about 9 wt %, from about 2 to about 8 wt %, from about 2 to about 6
wt %, from about 2.5 to about 6 wt %, from about 3 to about 5.5 wt
%, or from about 3 to about 5 wt % of Bis-aminopropyl diglycol
dimaleate.
[0132] In some embodiments, such as when the active agent is maleic
acid or a simple salt thereof, the active agent formulation may
contain from about 0.1 to about 30 wt %, from about 0.1 to about 20
wt %, from about 0.1 to about 10 wt %, from about 0.1 to about 10
wt %, or from about 0.5 to 5 wt % of maleic acid or a simple salt
thereof. Optionally, the active agent formulation contains about
from about 0.5 to about 10 wt %, from about 0.5 to about 9 wt %,
from about 1 to about 8 wt %, from about 1 to about 7 wt %, from
about 1 to about 6 wt %, from about 1 to about 3 wt %, or from
about 1 to about 2 wt % of maleic acid or a simple salt
thereof.
[0133] In certain embodiments, a second active agent formulation
may be provided, which may be further applied to hair following a
curling treatment as described herein. The second active agent
formulation may contain the same active agent(s) as the first
active agent formulation or may contain a different active agent(s)
than the active agent(s) in the first active agent formulation. The
second active agent formulation may contain the same concentration
of the active agent or a different concentration of the active
agent than the concentration of the active agent in the first
active agent formulation. Second active agent formulations
typically contain about 0.1 to 50 wt % of one or more of the active
agents described herein. The active agent formulation may contain
from about 0.1 to about 30 wt %, from about 0.1 to about 20 wt %,
from about 0.1 to about 10 wt %, from about 0.1 to about 10 wt %,
or from about 0.5 to 5 wt % of one or more of the active agents
described herein.
[0134] The second active agent may be in the form of a liquid or a
cream, optionally the second active agent is in an aqueous
solution. Optionally, the second active agent formulation contains
other suitable ingredients and/or excipients.
III. Hydroxide-Containing Formulations
[0135] The term "hydroxide-containing formulations" refers to
formulations that contain one or more hydroxide-containing agents.
The hydroxide-containing formulation is preferably odorless. The
hydroxide-containing formulation is preferably an aqueous
formulation.
[0136] The hydroxide-containing formulations do not contain a thiol
or sulfur-containing reducing agent(s), such as thioglycolic acid,
thiolactic acid, cysteine, cysteamine, homocysteine, glutathione,
thioglycerol, thiomalic acid, mercaptopropionic acid or salts
thereof or derivatives thereof, dithiothreitol, 2-mercaptoethanol,
thioxanthine, thio salicylic acid, thiopropionic acid,
N-acetylcysteine and salts thereof, alkali metal or alkaline earth
metal sulfites, bisulfites, ammonium sulfites, thioglycerin or
derivatives thereof. In certain embodiments, the hydroxide
formulations also do not contain other types of reducing agents,
such as alkylphosphines, dihydrolipoate, zinc formaldehyde
sulfoxylate, lipoic acid, sodium formaldehyde sulfoxylate,
potassium borohydride, and/or hydroquinone.
[0137] Hydroxide-containing formulations and their methods of
preparation are known in the art. In preferred embodiments the
hydroxide-containing formulations are liquids. Optionally, the
hydroxide-containing formulation is in the form of a paste.
Commercially available hydroxide-containing formulations, such as
in the form of relaxing formulations from the following commercial
brands: Mizani.RTM. Rhelaxer, Design Essentials.RTM., and Dudley's
Q.RTM., are typically in the form of pastes.
[0138] Exemplary hydroxide-containing agents include, but are not
limited, to alkali metal hydroxides such as sodium hydroxide,
lithium hydroxide, calcium hydroxide, and potassium hydroxide. In
some other embodiments, the agent is ammonium hydroxide or
guanidinium hydroxide. Hydroxide-containing agents are known to
those of skill in the art.
[0139] In preferred embodiments, the hydroxide -containing
formulations are free of any thiol- or sulfur-containing reducing
agents. Alternatively, the hydroxide-containing formulations are
substantially free of any thiol- or sulfur-containing reducing
agents described above. Hydroxide-containing formulations that are
substantially free of any thiol- or sulfur-containing reducing
agents may contain less than about 1 wt %, less than about 0.9 wt
%, less than about 0.8 wt %, less than about 0.7 wt %, less than
about 0.6 wt %, less than about 0.5 wt %, less than about 0.4 wt %,
less than about 0.3 wt %, less than about 0.2 wt %, or less than
about 0.1 wt % of any thiol- containing or sulfur-containing
reducing agent.
IV. Combined Formulations Containing Active Agent(s) and
Hydroxide-Containing Agent(s)
[0140] The term "combined formulation" refers to a formulation that
contains both one or more hydroxide-containing agent(s) and one or
more of the active agent(s) described above. The combined
formulation is preferably an aqueous formulation. The combined
formulation is preferably free or substantially free of any thiol
or sulfur-containing reducing agents described above. The combined
formulation preferably contains less than about 1 wt %, less than
about 0.9 wt %, less than about 0.8 wt %, less than about 0.7 wt %,
less than about 0.6 wt %, less than about 0.5 wt %, less than about
0.4 wt %, less than about 0.3 wt %, less than about 0.2 wt %, or
less than about 0.1 wt % of any thiol-containing or
sulfur-containing reducing agent.
[0141] The combined formulation generally does not contain a
nitrogen-containing base, such as guanadine, amidine, acetamide, or
a salt or derivative thereof.
[0142] In some embodiments, separate active agent formulations and
hydroxide-containing formulations are provided, and are mixed at
the time of use to provide a combined formulation.
[0143] In other embodiments, a combined formulation is provided
(the active agent(s) and hydroxide-containing agent(s) are provided
in a single formulation).
[0144] In some embodiments, the combined formulation is in the form
of a dry powder. Optionally, the dry powder includes one or more
excipient(s). An aqueous combined formulation can be formed by
adding the combined formulation in the form of a dry powder to a
suitable volume of water. Preferably, the resulting aqueous
combined formulation contains the active agent(s) at a
concentration of about 0.1% (wt) to 30% (wt) and the hydroxide
containing agent(s) at a concentration of about 0.1 to 5 (wt).
1. Concentrations
[0145] A combined formulation can contain a concentration of one or
more hydroxide-containing agents of about 0.1 to 5% (wt), about 0.1
to 3% (wt), about 0.1 to 2% (wt), or about 0.1 to 1% (wt). In
preferred embodiments, the concentration of one or more
hydroxide-containing agents in the combined formulation is about
0.1 wt %, 0.2 wt %, 0.3 wt %, 0.4 wt %, 0.5 wt %, 0.6 wt %, 0.7 wt
%, 0.8 wt %, 0.9 wt %, 1.0 wt %, 1.1 wt %, 1.2 wt %, 1.3 wt %, 1.4
wt %, or 1.5 wt %. The concentration of active agent in the
combined formulation can range from about 0.5% (wt) to about 50%
(wt) or greater. In certain embodiments, the combined formulation
contains about 0.5% (wt) to 20% (wt) active agent. In certain
embodiments, the combined formulation contains about 0.1 wt %, 0.2
wt %, 0.3 wt %, 0.4 wt %, 0.5 wt %, 0.6 wt %, 0.7 wt %, 0.8 wt %,
0.9 wt %, 1.0 wt %, 1.1 wt %, 1.2 wt %, 1.3 wt %, 1.4 wt %, 1.5 wt
%, 1.6 wt %, 1.7 wt %, 1.8 wt %, 1.9 wt %, 2.0 wt %, 2.0 wt %, 2.1
wt %, 2.2 wt %, 2.3 wt %, 2.4 wt %, 2.5 wt %, 2.6 wt %, 2.7 wt %,
2.8 wt %, 2.9 wt %, or 3.0 wt %, or any concentration between the
listed concentrations of the active agent(s).
[0146] In certain embodiments the combined formulations contain a
molar excess of hydroxide-containing agent compared to the active
agent(s) present having one or more acidic groups. In certain other
embodiments the combined formulations are prepared based on the
molar ratio of hydroxide-containing agent(s) to the number of
acidic groups (i.e., carboxylic acid) present in the active
agent(s) wherein the molar ratio can be about 2:1 or 1.5:1. In yet
other embodiments, the molar ratio of hydroxide-containing agent(s)
to the number of acidic groups (i.e., carboxylic acid) may be
greater than or less than about 2:1 or 1.5:1 depending on the
presence of one or more excipients and/or buffering agents, which
can be acidic or basic, and may be present in the combined
formulation.
2. Viscosity
[0147] The combined formulation may be in the form of a liquid.
Preferably, the viscosity of the liquid is less than the viscosity
of a cosmetic cream (less than about 8,000 cP, optionally less than
5,000 cP).
[0148] Viscosity of the combined formulation can be determined
according to known methods for measuring viscosity of fluids. In
one non-limiting exemplary method, a Ford viscosity cup viscometer
can be used to determine the viscosity of Newtonian fluids
according to testing methods provided under ASTM D 1200-94. A Ford
viscosity cup viscometer can also be used to determine the
viscosity of non-Newtonian fluids according to testing methods
provided under ASTM D 2196. Classical Newtonian fluids demonstrate
a viscosity, which is essentially independent of shear rate.
Non-Newtonian fluids, however, demonstrate a viscosity which either
decreases or increases with increasing shear rate, e.g., the fluids
are "shear thinning" or "shear thickening", respectively. These and
other methods of measuring viscosity are described in Viswanath, et
al. Viscosity of Liquids: Theory, Estimation, Experiment, and Data,
Dordrecht:Springer, 2007, Print. Exemplary viscosities of fluids
measured by a viscosity cup method (at 20.degree. C.) in units of
centipoise include water (1 cP), hand cream (8,000 cP), liquid soap
(85 cP), and shampoo (3,000-5,000 cP).
[0149] Suitable viscosities for the combined formulations are in
the range of about 1 to 3,000 cP, 1 to 2,000 cP, 1 to 1,000 cP, 1
to 750 cP, 1 to 500 cP, 1 to 250 cP, 1 to 100 cP, 1 to 90 cP, 1 to
80 cP, 1 to 70 cP, 1 to 60 cP, 1 to 50 cP, 1 to 40 cP, 1 to 30 cP,
1 to 20 cP, or 1 to 10 cP. In some embodiments, the combined
formulations have a viscosity, as measured by a viscosity cup
viscometer, which is within 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%,
10%, 20%, 30% of the viscosity of a reference fluid, such as water
or shampoo, measured under the same conditions. In preferred
embodiments, the combined formulation has a viscosity of less than
8,000 cP.
3. pH
[0150] In some embodiments, the pH of the combined formulation is
about 11 or greater. In some embodiments, the pH of the combined
formulation is about 10 or greater. In certain embodiments, the pH
of the combined formulation is about 9.5 or greater, 9.6 or
greater, 9.7 or greater, 9.8 or greater, 9.9 or greater, 10.0 or
greater, 10.1 or greater, 10.2 or greater, 10.3 or greater, 10.4 or
greater, 10.5 or greater, 10.6 or greater, 10.7 or greater, 10.8 or
greater, 10.9 or greater, 11.0 or greater, 11.1 or greater, 11.2 or
greater, 11.3 or greater, 11.4 or greater, 11.5 or greater, 11.6 or
greater, 11.7 or greater, 11.8 or greater, 11.9 or greater, or 12.0
or greater, such as up to 14.0. In certain other embodiments, the
pH of the combined formulation is about 9.5, 9.6, 9.7, 9.8, 9.9,
10.0, 10.1, 10.2, 10.3, 10.4, 10.5, 10.6, 10.7, 10.8, 10.9, 11.0,
11.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8, 11.9, or 12.0.
4. Odorless
[0151] The combined formulation generally does not contain a foul
smell. Preferably, the combined formulation is odorless. However,
perfumes may be included, if desired.
[0152] A. Combined Curling Formulations Formed by Mixing
Immediately Prior to Application
[0153] In some embodiments, combined formulations having a first
active agent formulation and a second formulation containing
hydroxide-containing agents are provided. These formulations are
mixed at the time of use (such as in a salon by a stylist and/or
colorist) to provide a combined formulation for curling hair.
[0154] In certain embodiments of the combined formulations, the
weight ratio of the one or more hydroxide-containing agents to the
one or more active agents in the combined formulation can be in the
range of about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to
1:3. In some embodiments, the weight ratio of the one or more
hydroxide-containing agents to the one or more active agents in the
combined formulation is in the range of about 10:1 to about 1:1;
5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1. In some instances, the
weight ratio is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1,
1:1, 1:2, 1:3, 1:4, or 1:5, preferably about 5:1, 4:1, 3:1, 2:1,
1:1, 1:2, 1:3, 1:4, or 1:5 or within about 10% of these ratios.
[0155] In such combined formulations, the amount of active agent(s)
present does not lower the pH of the combined formulation to be
below about a pH of 9.5 and more preferably does not lower the pH
of the combined formulation below about a pH of 10.5.
[0156] B. Pre-Mixed Combined Curling Formulations
[0157] In some embodiments, combined formulations are provided,
which contain both active agent(s) and hydroxide-containing
agent(s). Such combined formulations can be sold as commercial
formulations (to distributors and/or salons) as pre-mixed curling
formulations containing both the active agent(s) and
hydroxide-containing agent(s).
[0158] In some embodiments of the combined formulations, the weight
ratio of the one or more hydroxide-containing agents to the one or
more active agents in the combined formulation can be in the range
of about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3.
In some embodiments, the weight ratio of the one or more
hydroxide-containing agents to the one or more active agents is in
the range of about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or
3:1 to 1:1. In some instances, the weight ratio of the one or more
hydroxide-containing agents to the one or more active agents in the
combined formulation is about 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1,
3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, and preferably about 5:1,
4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5, or within about 10% of
these ratios.
[0159] Pre-mixed combined formulations can be prepared prior to use
and sold as a commercial product to distributors and/or salons. The
pre-mixed combined formulations can be stored and are shelf-stable.
"Stable" or "shelf-stable" as used herein with respect to
shelf-life means that at least 40, 45, 50, 55, 60, 65, 70, 75, 80,
85, 90, or 95% of the active agent is not degraded over a specified
time period, such as at least 6 months, at least 1 year, at least 2
years, at least 3 years after forming the combined formulation.
Typically, the pre-mixed combined formulations are stored at room
temperature optionally under light-free conditions.
V. Kits
[0160] In some embodiments, kits for curling hair contain an active
agent formulation containing an active agent. The kit may further
contain a second formulation, also referred to herein as the
hydroxide-containing formulation.
[0161] Alternatively, the kit may contain one or more powders
containing the hydroxide-containing agent(s) and/or the active
agent(s) and/or one or more excipient(s), as discussed in detail
below. For example, the kit can contain a single powdered
formulation containing the hydroxide-containing agent(s),
optionally further containing the active agent(s) and/or
excipient(s).
[0162] Alternatively, the kit can contain two or more separate
powdered formulations, were a first powder contains the
hydroxide-containing agent(s), and a second powder contains the
active agent(s) and/or excipient(s). The powdered formulations may
be provided in sealed container or package to prevent contact with
water or a humid environment.
[0163] The kits described herein may also include a shampoo, a
conditioner, curling rods, perming tools, gloves, an applicator, an
applicator bottle (preferably having a fine application tip), or a
combination thereof.
[0164] The hydroxide-containing agent and active agent formulations
are typically provided separately and instructions are provided for
applying the hydroxide-containing agent and active agent
formulations to the hair. For example, the instructions may provide
for creating a combined formulation by mixing the
hydroxide-containing agent and active agent formulations, and then
applying the combined formulation to the hair. Alternatively, the
instructions may provide for applying the hydroxide-containing
agent to the hair simultaneously while applying the active agent
formulation to the hair (but not as a pre-mixed, combined
formulation). The instructions may also include instructions for
selecting the desired amount of active agent to be used, such as by
specifying a volume or mass (or range thereof) of the active agent
or active agent formulation, the desired weight ratio of active
agent to hydroxide-containing agent, and/or the desired weight
ratio of first hydroxide-containing formulation to second active
agent formulation in order to control the level of curl imparted to
the hair.
[0165] Alternatively, instructions are provided for first applying
the hydroxide-containing agent to the hair and subsequently
applying the active agent formulation to the hair. The instructions
may specify the amount of time (i.e., in the range of about one
second to about 30 minutes, more preferably within about 60
seconds) that can pass following the application of the
hydroxide-containing formulation before the application of the
active agent formulation and/or the amount of active agent
formulation to be applied in order to control the level of curl
imparted to the hair. The instructions may also specify how to
select the desired amount of active agent to be used, such as by
specifying a volume or mass (or range thereof) of the active agent
or active agent formulation, the desired weight ratio of active
agent to hydroxide-containing agent, and/or the desired weight
ratio of a first hydroxide-containing formulation to a second
active agent formulation in order to control the level of curl
imparted to the hair being curled.
[0166] In other embodiments, the kits for curling hair contain a
combined formulation as described herein.
[0167] Instructions provided can also specify reshaping of the hair
prior to, during, or following the application of a formulation
containing one or more active agents and/or one or more
hydroxide-containing agents. Such instructions detail reshaping the
hair using a tool, device, or technique to place the hair in a
particular shape, which is later removed or deconstructed, to
achieve a desired hairstyle. For example, reshaping the hair can
include rolling the hair on a roller, rod, and/or curler; or
braiding or twisting the hair; or combinations thereof. Reshaping
of the hair can include braiding and/or twisting of the hair,
optionally in combination with or in the absence of any roller,
curler, curling rod, and/or other suitable hair-shaping instrument.
Reshaping the hair according to the methods described is discussed
in further detail below.
[0168] Instructions also include details on the setting period for
the hair following application of one or more formulations as
discussed above, which is typically in the range of about 1 to 90
minutes, preferably about 10, 20, 30, or 40 minutes. In some
instances, the setting period can be in the range of about 15 to 30
minutes, more preferably about 20 minutes. Details on the setting
period are discussed further below.
[0169] Instructions may further include details on rinsing the hair
following the setting period, removal of any tool, device, or
technique and/or braid used to place the hair in a particular shape
during the reshaping step, and shampooing and optionally
conditioning the curled hair. Details of the aforementioned steps
are discussed further below.
[0170] Exemplary instructions can include directions to perform the
following: [0171] 1. Shampooing the hair (such as with a light
clarifying shampoo) and towel drying the hair; [0172] 2. Reshaping
the hair, such as by wrapping the hair on a rod or other perming
tool, and/or braiding the hair; [0173] 3. Saturating the hair, rods
or other perming tools, and/or braids thoroughly with
hydroxide-containing agent and active agent formulations, either
applied simultaneously as individual formulations, or applied as a
single combined formulation; [0174] 4. Allowing setting for a
period of 20 minutes; [0175] 5. Rinsing the hair, rods, or other
perming tools, and/or braids following the setting period of 20
minutes to remove the formulation(s); [0176] 6. Removing/unwrapping
the hair from rods or other perming tools out, if used, or
unbraiding the hair; and [0177] 7. Shampooing, conditioning, and
styling the hair as usual.
[0178] A. Hydroxide-Containing Formulation
[0179] In some embodiments, the kit contains hydroxide-containing
agent(s) or a formulation thereof that contains one or more
hydroxide-containing agents as described above. The
hydroxide-containing formulation is typically provided in the form
of a liquid in a container. The hydroxide- containing formulation
included in the kit is preferably odorless. In some embodiments,
the hydroxide-containing formulation may contain perfumes.
Alternatively, the kit may further include perfumes, which may be
added to the hydroxide-containing formulation.
[0180] In some other instances, the hydroxide-containing agent(s)
may be provided as a dry powder in a sealed package and the powder
may optionally include excipient(s), such as those discussed
herein. A suitable mixing container for the powder may be provided.
An exemplary mixing container is an applicator bottle. Instructions
are provided for preparing the hydroxide-containing formulation and
indicate to the user the suitable volume of aqueous solution, such
as water, needed to form the hydroxide-containing formulation.
Optionally, the aqueous solution contains the active agent, i.e. is
the active agent formulation.
[0181] B. Active Agent Formulation
[0182] The active agent formulation contains one or more active
agents as described herein. Suitable formulations containing the
active agents are discussed above. The active agent formulation may
be in any suitable form. Typically, the active agent formulation is
a flowable liquid at standard temperature and pressure, such as a
low to moderate viscosity liquid. The active agent formulation is
provided in a suitable container, which depends on the form of the
formulation.
[0183] In some embodiments, the active agent formulation is
provided as two or more separate ingredients. For example, the
active agent may be provided as a dry powder in a sealed package
and the excipient(s) provided in a vial or other container. A
suitable mixing container for the active agent and the excipient(s)
may be provided.
[0184] The active agent formulation included in the kit is
preferably odorless. In some embodiments, the active agent
formulation may contain perfumes. Alternatively, the kit may
further include perfumes, which may be added to the active agent
formulation.
[0185] In some other instances, the active agent(s) may be provided
as a dry powder in a sealed package and the powder may optionally
include excipient(s), such as those discussed herein. A suitable
mixing container for the powder may be provided. An exemplary
mixing container is an applicator bottle. Instructions are provided
for preparing the active agent formulation and indicate to the user
the suitable volume of aqueous solution, such as water, needed to
form the active agent formulation. Optionally, the aqueous solution
contains the hydroxide-containing agent, i.e. is the
hydroxide-containing formulation.
[0186] C. Combined Formulation
[0187] In some embodiments, the kit contains a pre-mixed combined
formulation, which contains both the active agent(s) and the
hydroxide-containing agent(s), as described above. The combined
formulation can be shelf-stable for at least 6 months, 7 months, 8
months, 9 months, 10 months, 11 months, optionally at least 1 year,
or longer.
[0188] The combined formulation is typically provided in the form
of a liquid in a container. The combined formulation included in
the kit is preferably odorless. In some embodiments, the combined
formulation may contain perfumes. Alternatively, the kit may
further include perfumes, which may be added to the combined
formulation.
[0189] In yet other instances, the hydroxide-containing agent(s)
and active agent(s) may be provided in the form of a dry powder in
a sealed container or package, where the powder optionally includes
excipient(s). A suitable mixing container for the powder may be
provided. An exemplary mixing container can be an applicator
bottle. Instructions are provided for preparing the combined
formulation in the form of a liquid. The instructions also indicate
to the user the suitable volume of aqueous solution, such as water,
needed to form the hydroxide-containing formulation. Preferably,
the resulting combined formulation in liquid form, contains the
active agent(s) at a concentration of about 0.1% (wt) to 30% (wt)
and the hydroxide containing agent(s) at a concentration of about
0.1 to 5% (wt).
VI. Methods of Use
[0190] Methods for curling hair are described herein. Preferably,
the methods described herein are free of or substantially free of
any thiol- or sulfur-containing reducing agent. Preferably, each
step in the methods described herein is free of or substantially
free of any thiol- or sulfur- containing reducing agent. Exemplary
thiol- or sulfur-containing reducing agent(s) include thioglycolic
acid, thiolactic acid, cysteine, cysteamine, homocysteine,
glutathione, thioglycerol, thionialic acid, mercaptopropionic acid
or salts thereof or derivatives thereof, dithiothreitol,
2-mercaptoethanol, thioxanthine, thio salicylic acid, thiopropionic
acid, N-acetylcysteine and salts thereof, alkali metal or alkaline
earth metal sulfites, bisulfites, ammonium sulfites, thioglycerin
or derivatives thereof. As used herein, "substantially free of any
thiol- or sulfur-containing reducing agent" with respect to a step
in a method or to the entire method indicates that each formulation
used or created in the step or method contains less than about 1 wt
%, less than about 0.9 wt %, less than about 0.8 wt %, less than
about 0.7 wt %, less than about 0.6 wt %, less than about 0.5 wt %,
less than about 0.4 wt %, less than about 0.3 wt %, less than about
0.2 wt %, or less than about 0.1 wt % of any thiol- or
sulfur-containing reducing agent. In some embodiments, the method
is free of or substantially free of any known reducing agent. In
some embodiments, each step in the method is free of or
substantially free of any known reducing agent. Exemplary reducing
agents include, but are not limited, the sulfur containing and
thiol-containing reducing agents listed above, alkylphosphines,
dihydrolipoate, zinc formaldehyde sulfoxylate, sodium formaldehyde
sulfoxylate, lipoic acid, potassium borohydride, and/or
hydroquinone. "Substantially free of any known reducing agent" with
respect to a step in a method or to the entire method indicates
that each formulation used or created in the step or method
contains less than about 1 wt %, less than about 0.9 wt %, less
than about 0.8 wt %, less than about 0.7 wt %, less than about 0.6
wt %, less than about 0.5 wt %, less than about 0.4 wt %, less than
about 0.3 wt %, less than about 0.2 wt %, or less than about 0.1 wt
% of any known reducing agent.
[0191] The curling methods can be used to impart curl to a variety
of different types of hair, including but not limited to naturally
straight hair, such as Asian hair, straight Hispanic hair, or
straight Caucasian hair, wavy hair in general, and hair that was
previously subjected to a relaxing treatment, colored, or
bleached.
[0192] In some embodiments, the methods include controlling,
selecting, or tuning the level of curl imparted during a hair
curling process or treatment (using a hydroxide-containing
formulation) by controlling the relative amount of an active agent
formulation to the amount of hydroxide-containing agent
formulation.
[0193] In some embodiments, a method for curling hair involves
applying a first formulation to the hair containing one or more
hydroxide-containing agents and applying a second formulation to
the hair comprising one or more active agents of Formulae I, II,
and/or III, as described above. According to certain embodiments,
the application of the first and second formulations is performed
simultaneously. For example, the first and the second formulations
are optionally mixed to form a combined formulation prior to
application and the combined formulation is applied to the hair.
For example, when the hair to be curled is set as desired on a rod
or curler, first one or more hydroxide-containing agents may be
added to a formulation containing the active agent, or vice versa
to form a single combined formulation and the combined formulation
may be applied to the hair being curled.
[0194] Preferably, when the first and second formulations are
applied simultaneously as a combined formulation, the amount of
active agent formulation present in the combined formulation does
not lower the pH of the combined formulation to a pH below about
9.5, and more preferably does not lower the pH of the combined
formulation to a pH below about 10.5. In other embodiments, when
the first and second formulations are applied simultaneously, the
amount of active agent formulation in the combined formulation
results in a combined formulation with a pH of about 10 or greater,
and more preferably a pH of about 11 or greater. In certain
embodiments, the pH of the combined formulation is about 9.5 or
greater, 9.6 or greater, 9.7 or greater, 9.8 or greater, 9.9 or
greater, 10.0 or greater, 10.1 or greater, 10.2 or greater, 10.3 or
greater, 10.4 or greater, 10.5 or greater, 10.6 or greater, 10.7 or
greater, 10.8 or greater, 10.9 or greater, 11.0 or greater, 11.1 or
greater, 11.2 or greater, 11.3 or greater, 11.4 or greater, 11.5 or
greater, 11.6 or greater, 11.7 or greater, 11.8 or greater, 11.9 or
greater, or 12.0 or greater, such as up to 14.0. In certain other
embodiments, the pH of the combined formulation is about 9.5, 9.6,
9.7, 9.8, 9.9, 10.0, 10.1, 10.2, 10.3, 10.4, 10.5, 10.6, 10.7,
10.8, 10.9, 11.0, 11.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8,
11.9, or 12.0.
[0195] In certain embodiments, the preferred low end of the pH
range of the combined formulation depends on the type of hair being
curled. In non-limiting examples, the pH of the combined
formulation is preferably no less than about 13 or about 12 when
Asian hair is being curled. In another non-limiting example, the pH
of the combined formulation is preferably no less than about 11 or
about 10 when Caucasian hair is being curled. In other non-limiting
examples, the pH of the combined formulation is about 10 or about
11 or greater when Asian hair is being curled. In another
non-limiting example, the pH of the combined formulation is about
9.5 or about 10 or greater when Caucasian hair is being curled.
[0196] Preferably, the curling methods described are performed at
room temperature and in the absence of any application of an
external heat source during the curling method. In less preferable
embodiments, heating may be applied, for example during the setting
period after the hydroxide-containing and active agent formulations
have been applied to the hair. Heating of the hair during the
setting period is preferably kept below about 100.degree. C., about
90.degree. C., about 80.degree. C., about 70.degree. C., about
60.degree. C., or about 50.degree. C. Non-limiting examples of heat
sources that may be used during the setting period include, but are
not limited to, a hair dryer or salon hair dryer.
[0197] Following application of the first and second formulations
or the combined formulation, the hair is rinsed after a setting
period. Further, a second active agent formulation containing one
or more active agents of Formulae I, II, and/or III may optionally
be applied subsequently to the hair (which was previously treated
in the first step).
[0198] In some embodiments, the method for curling hair involves
applying a first formulation to the hair containing one or more
hydroxide-containing agents and subsequently applying to the hair
one or more active agents of Formulae I, II, and/or III, as
described above.
[0199] In still other embodiments, one or more of the active agents
of the Formula I, II, and/or III, as described above, may be added
to the formulation containing one or more hydroxide-containing
agents prior to applying the formulation to the hair to form a
combined formulation. Typically, the active agent(s) are added
immediately prior to applying the combined formulation to the hair
for the curling treatment.
[0200] The curling methods described herein curl hair; in contrast,
applying to hair hydroxide-containing agent(s) alone would not be
expected to produce any curl. Further the amount of the one or more
active agents of the second formulation in combination with the
first formulation are effective to impart a desired level of curl
in the curled hair with reduced damage or breakage compared to
treatments that do not include an active agent according to
Formulae I, II, and/or III.
[0201] A. Reshaping the Hair
[0202] The methods described herein include the step of reshaping
hair prior to, during, or following the application of any
formulation containing one or more active agents and/or one or more
hydroxide-containing agents.
[0203] Reshaping the hair typically includes using a tool, device,
or technique to place the hair in a particular shape, which is
later removed or deconstructed, to achieve a desired hairstyle. For
example, reshaping the hair can include rolling the hair on a
roller, rod, and/or curler; or braiding or twisting the hair; or
combinations thereof.
[0204] In some embodiments, reshaping the hair includes rolling the
hair on or around a perm roller, curler, curling rod, or other
suitable hair shaping instruments or tools prior to application of
any formulation or combinations thereof. The size of the rod,
curler, perm roller or other hair-shaping tool is selected to
achieve a desired curl shape and size. Typically, the size of the
curl in the hair following the methods described herein is larger
than the diameter of the rod, curler, perm roller or other
hair-shaping tool that is used in the reshaping step. For example,
the size of the curls that are formed following the methods
described herein can be 2 to 10 times larger, optionally 5 to 10
times larger, or 8 to 10 times larger than the diameter of the rod,
curler, perm roller or other hair-shaping tool that is used.
[0205] Reshaping of the hair can include braiding and/or twisting
of the hair, optionally in combination with or in the absence of
any roller, curler, curling rod, and/or other suitable hair-shaping
instrument.
[0206] Braided or twisted hair, for example, will then acquire curl
because of the braiding or twisting of the hair. The hair may be
braided or twisted as desired to tune the size and shape of the
curl imparted following application of the curling methods
described herein. In yet another instance, the hair may be braided
or twisted, optionally in the absence of any roller, curler,
curling rod, and/or other suitable hair shaping instrument, during
the application of an active agent formulation,
hydroxide-containing formulation, either simultaneously or as
combined formulations thereof to the hair (i.e., wetting of the
hair) as described herein. The braided or twisted hair will then
acquire curl because of the braiding or twisting of the hair. The
hair may be braided or twisted as desired to tune the size and
shape of the curl imparted following application of the curling
methods described herein.
[0207] In preferred embodiments, the hair is rolled (e.g. on
curlers or rods), or is braided or twisted, prior to the
application of the formulation(s) containing one or more
hydroxide-containing agents and active agent(s).
[0208] In some embodiments, the hair may be rolled on curlers or
rods, or is braided or twisted, after the application of the
formulation(s) containing one or more hydroxide-containing agents
and active agent(s). In these instances, the hair is preferably
rolled, braided, or twisted immediately after application of the
formulations at least within about 1-15 minutes, more preferably
about 1-10 minutes, and most preferably about 1-5 minutes.
[0209] B. Apply Formulation(s) Containing One or More
Hydroxide-Containing Agents and Active Agent(s)
[0210] The active agent is applied to the hair either
simultaneously with the hydroxide-containing agent (such as in the
form of a combined formulation) or is applied immediately following
the application of the hydroxide- containing formulation (wherein
the hair has not been rinsed prior to application of the second
formulation) or, alternatively, applied at a short interval of time
immediately following the application of the hydroxide-containing
formulation. "Short interval," as used herein, refers to a period
in the range of one second to 30 minutes, one minute to 20 minutes,
or 5 minutes to 15 minutes.
[0211] Preferably, the active agent is applied simultaneously with
the one or more hydroxide-containing agent(s) to the hair.
[0212] The active agent formulation may be applied as a single
application, or application may be repeated one or more times as
needed. Preferably, the amount of active agent formulation applied
is sufficient to saturate the hair. The volume of active agent
formulation applied to the hair in each application may be about 1
to about 200 mL depending on the length and volume of hair.
[0213] In certain other embodiments, a pre-mixed, combined
formulation containing one or more hydroxide-containing agent(s)
and a second formulation containing one or more active agent(s) is
applied to the hair as part of a curling process.
[0214] In some embodiments, a first formulation containing one or
more hydroxide-containing agent(s) and a second formulation
containing one or more active agent(s) are mixed and applied to the
hair as a single combined formulation containing both types of
agents to the hair as part of a curling process. Alternatively, the
first formulation and second formulation can be applied
simultaneously to the hair without a prior mixing step.
[0215] When the formulations are applied simultaneously, the amount
of active agent formulation used does not lower the pH of the
combined formulation to be below about a pH of 10 and preferably
does not lower the pH of the combined formulation below about a pH
of 11 and the weight ratio of the hydroxide-containing agent
formulation to the active agent formulation can be in the range of
about 10:1 to about 1:5; 5:1 to 1:5; 4:1 to 1:4; or 3:1 to 1:3. In
some embodiments, the weight ratio of the hydroxide-containing
agent formulation to the active agent formulation is in the range
of about 10:1 to about 1:1; 5:1 to 1:1; 4:1 to 1:1; or 3:1 to 1:1.
In some instances, the weight ratio of the hydroxide-containing
agent formulation to the active agent formulation is about 10:1,
9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5,
and preferably about 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, or 1:5
or within about 10% of these ratios. The amount of the second
formulation containing active agent(s) and the concentration of the
active agent(s) present therein can be varied as desired when using
other hydroxide-containing agents to achieve similar results.
[0216] Formulations containing one or more hydroxide-containing
agents, having a pH of about 11 to 14, represent a difference in
hydroxide ion concentration of about 100 times between the ends of
the range may be used. In such instances, the amount of active
agent(s) can be varied as a function of the pH of the commercially
available relaxing formulation being used, and can be further
adjusted according to the buffering capacity of each
hydroxide-containing agent formulation, if a buffering agent is
present.
[0217] In certain embodiments, the first and second formulations
can be prepared at the time of use or immediately before as a
single combined formulation containing both one or more
hydroxide-containing agent(s) and the active agent(s) of Formulae
I, II, and/or III having the weight ratios as described above.
[0218] In certain embodiments, the first and second formulation can
be prepared as a single combined formulation, containing both the
one or more hydroxide-containing agent(s) and the active agent(s)
of Formulae I, II, and/or III having the weight ratios as described
above and stored prior to use.
[0219] The single combined formulation typically has a pH in the
range of 10 to 14, preferably a pH ranging from 11 to 13. According
to certain embodiments, the single combined formulation contains
about 0.1 to 10 wt % of one or more hydroxide-containing agent(s)
and about 0.05 to 10 wt % of one or more active agents when
prepared as a single aqueous solution or when a first and second
formulation are prepared individually and subsequently mixed to
form a single combined formulation.
[0220] Following application of the active agent and
hydroxide-containing agent, the hair is allowed to set ("setting
period") for a period of time, typically in the range of about 1 to
90 minutes, preferably about 10, 15, 20, 30, 40, 50, or 60 minutes.
In some instances, the setting period is preferably less than about
one hour, 45 minutes, 30 minutes, 20 minutes, 15 minutes, or 10
minutes. In some instances, the setting period can be in the range
of about 15 to 30 minutes, more preferably about 20 minutes.
[0221] Preferably, the method is performed at room temperature and
in the absence of any application of an external heat source during
the method. In less preferable embodiments, heat may be applied,
for example, during the setting period after the
hydroxide-containing and active agents have been applied to the
hair. Heating of the hair is preferably kept below about
100.degree. C., about 90.degree. C., about 80.degree. C., about
70.degree. C., about 60.degree. C., or about 50.degree. C.
Non-limiting examples of heat sources, which may be used during the
setting period, include, but are not limited to, a hair dryer or
salon hair dryer.
[0222] C. Removal of Formulations from Hair
[0223] The formulation containing one or more hydroxide-containing
agents and the active agent formulation or combined formulations
thereof applied to the hair is rinsed from the hair. Typically the
rinsing step lasts for a period in the range of about 0.1 to 10
minutes, preferably for about 1 to 5 minutes, more preferably about
3 to 5 minutes. If the hair is rinsed prior to removal from the
curling rod, curler, or roller, or undoing of the braid and/or
twist, then the rinsing time is preferably longer.
[0224] Optionally, the curled hair is removed from the
rods/rollers/curlers or the braid or twist is undone, and the hair
is then rinsed. However, this process generally takes a relatively
long time. Therefore, it is generally useful when only a few rods,
curlers, or rollers are placed in the hair. Optionally the hair may
be immediately rinsed, shampooed and/or conditioned or subjected to
one or more wash cycles and then allowed to dry (i.e., air drying,
blotting, towel drying, blow drying). Air drying, blotting and
towel drying occur at room temperature. Rinsing can be performed
with water at a temperature ranging from about room temperature
(i.e., about 23-25.degree. C.) to about 40.degree. C.
[0225] The curled hair can be rinsed, shampooed, optionally
conditioned, or subjected to one or more wash cycles subsequent to
the curling process. The hair may be rinsed and subsequently
shampooed, optionally conditioned, or subjected to one or more wash
cycles immediately (e.g. within 10, 15, 25, 30, 45, 60 seconds (one
minute), two minutes, three minutes, four, or five minutes
following application) after application of the active agent
formulation.
[0226] In some embodiments of the methods described herein, the
curled hair is rinsed, shampooed, optionally conditioned, or
subjected to one or more wash cycles about 45 minutes after the
application of the formulations containing one or more
hydroxide-containing agents and active agent(s), when they are
applied simultaneously. In some embodiments of the methods
described herein, the curled hair is rinsed, shampooed, optionally
conditioned, or subjected to one or more wash cycles about 15
minutes after the application of an active agent formulation, when
the active agent formulation is applied immediately (i.e., within
about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 seconds (one
minute), two minutes, three minutes, four, or five minutes) after
applying the hydroxide-containing agent formulation.
[0227] Alternately, the hair may be rinsed, shampooed, optionally
conditioned, or subjected to one or more wash cycles and a
subsequent application of the active agent formulation may be
applied which does not have to be rinsed, shampooed, optionally
conditioned, or subjected to one or more wash cycles after
application to the hair.
[0228] In summary, the method of use can include a combination of
optionally preparing the hair prior to curling; reshaping hair;
applying formulation(s) containing one or more hydroxide-containing
agents and active agent(s) to the hair; removal of formulation(s)
from hair; removal of any reshaping tools; and shampooing,
conditioning, and styling the hair.
[0229] As a non-limiting example, the methods of use can include:
[0230] 1. Shampooing the hair (such as with a light clarifying
shampoo) and towel drying the hair; [0231] 2. Reshaping the hair,
such as by wrapping the hair on a rod or other perming tool, and/or
braiding the hair; [0232] 3. Saturating the hair, rods or other
perming tools, and/or braids thoroughly with hydroxide-containing
agent and active agent formulations, either applied simultaneously
as individual formulations, or applied as a single combined
formulation; [0233] 4. Allowing setting for a period of about 20
minutes; [0234] 5. Rinsing the hair, rods, or other perming tools,
and/or braids following the setting period of about 20 minutes to
remove the formulation(s); [0235] 6. Removing/unwrapping the hair
from rods or other perming tools out, if used, or unbraiding the
hair; and [0236] 7. Shampooing, conditioning, and styling the hair
as usual.
[0237] D. Optionally Apply a Second Active Agent Formulation to the
Hair
[0238] Optionally, while the hair is still in the
rollers/rods/curlers/braid/twist, a second active agent formulation
having one or more of the active agents of Formulae I, II, and/or
III may be applied to the treated hair.
[0239] The optional second active agent formulation, when applied,
is allowed to sit on the hair for a period in the range of about 1
to 30 minutes, more preferably about 1 to 15 minutes.
[0240] The curled hair is then removed from the perm
roller/curler/curling rod/braid/twist and can optionally be
immediately shampooed, rinsed, optionally conditioned, or subjected
to one or more wash cycles and then allowed to dry (i.e., air
drying, blotting, towel drying, blow drying).
[0241] E. Properties of Curled Hair Following Curling Treatment
[0242] Treatment as described herein can improve hair quality, such
as appearance (e.g., sheen) and feel, increase wet and dry
strength, and decrease hair breakage, even when the hair is
subjected to subsequent styling treatments, such as coloring or
bleaching, or additional curling or straightening treatments (such
as to modify the curl, change the shape of the curl, or modify the
level of curl (e.g. tighter or looser curls)).
1. Reduced Damage/Hair Breakage
[0243] Hair breakage is a significant problem encountered during
typical hair curling treatments, such as permanent wave treatments.
In the present embodiments, hair breakage can be decreased as
compared to standard curling treatments by using the curling
methods described herein.
2. Retention of Curl
[0244] In certain embodiments, the curl imparted to the hair can be
retained after at least about 1 to 30 wash cycles, preferably for
at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 40, or 50
wash cycles.
[0245] The amount and shape of the curl imparted is influenced by
the size of the curling device or technique (e.g. curlers, rollers,
rods, braids, or twists) used in combination with the application
of the first and second formulations described herein.
[0246] The curl imparted to the hair following a curling treatment
can be retained with no appreciable or substantially no appreciable
change (i.e., a reduction of curl of less than 5%, 4%, 3%, 2%, or
1%) for a period of time in the range of one week to six months,
such as in the range of two weeks to four months or one month to
three months. In some embodiments, a percentage of curl can be
maintained for at least about one week, two weeks, three weeks,
four weeks, one month, two months, three months, four months, five
months, six months, or longer. The treated hair retains curl when
subjected to conditions under which it would not retain the curl
absent treatment according to the methods described herein, such as
rinsing, shampooing, conditioning, or one or more wash cycles.
"Wash cycles," as used herein refers to hair, which has been
subjected to the following: rinsing-shampooing
-rinsing-conditioning-rinsing of the hair following a curling
treatment described herein. Rinsing can be performed with water at
a temperature ranging from about room temperature (i.e., about
23-25.degree. C.) to about 40.degree. C.
[0247] In some embodiments, the percentage of curl is reduced by
less than about 5%, 10%, 15%, or 20% of the imparted curl after
about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, or
50 or more wash cycles. In yet other embodiments, the percentage of
curl is reduced by less than about 30%, 40%, or 50% of the imparted
curl after about 20-50 wash cycles. In certain embodiments, the
imparted curl is retained with no appreciable or substantially no
appreciable change after about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15,
20, 25, 30, 35, 40, 45, or 50 or more wash cycles, preferably two
or more wash cycles, more preferably at least 5 wash cycles, more
preferably after about 5-10 wash cycles.
[0248] As used herein, "percent change in the level of curl" and
"percentage of change in curl" are used interchangeably to refer to
the level of curl that is maintained over time (e.g. following one
or more wash cycles) following a curling treatment. One exemplary
method for determining percent change in the level of curl in the
hair (e.g. a swatch of hair) is based on the following formula:
Percent Change in the level of
Curl=(L.sub.F-L.sub.i)/(L.sub.i).times.10
[0249] where L.sub.F is the final length of the hair following one
or more wash cycles or a set period of time, and L.sub.1 is the
length of the curled hair following a curling treatment. For
example, the level of curl (percent curl) following treatment with
the active agent(s) and hydroxide-containing agent(s) can be
maintained after washing with no significant loss in the curl, such
the range of about 0-50%, for example less than about 40%, less
than about 30%, less than about 20%, less than about 10%, less than
about 5% change in the level of curl. The change in the level of
curl can be determined after one or more wash cycles, with L.sub.F
corresponding to the length of the curled hair after a particular
number of wash cycles, such as after 1, 2, 3, 4, 5, 6, 7, 8, 9, 10,
15, 20, 25, 30, 35, 40, 45, or 50 or more wash cycles.
Alternatively, the level of curl imparted following a curling
method and the corresponding retention of curl after one or more
wash cycles can be evaluated by visual inspection. Visual
inspection is particularly useful when the hair being curled has
natural curl or has been previously curled. Visual inspection is
also useful to determine changes in the nature of curls, such as
the shape and/or tightness of the curl.
[0250] F. Optional Subsequent Straightening or Curling Treatments
to Modify the Level of Curl
[0251] After performing the hair curling methods described herein,
the level of curl can be modified by one or more additional curling
treatments according to the same methods described herein. Repeated
application of the curling methods described to hair can
selectively modify the level of curl over a period, such as from
day-to-day, week-to-week or month-to-month, or other suitable time
intervals. For example, the curling methods may be repeated 10, 20,
30, 40, 50, or more times at the aforementioned time intervals.
Optionally, after using the hair curling methods described herein,
the hair can be treated immediately thereafter (i.e., within 24
hours of the curling treatment) with a straightening process to
straighten the hair. Further, a subsequent curling method may
optionally be applied within 24 hours to curl the hair. This allows
one to tune and modify the level of curl in hair, as desired,
without damaging the hair.
[0252] G. Exemplary Method of Use
[0253] In a non-limiting embodiment of the methods described
herein, hair is wrapped/rolled on one or more rods or perming
tools. Afterwards, a combined formulation containing one or more
hydroxide-containing agents and active agent(s) is then applied to
hair. In some embodiments, the combined formulation is applied
simultaneously while (not subsequent to) wrapping or rolling the
hair onto the rods or perming tools. Typically, one or more
sections of the hair are wrapped around or rolled onto one or more
perming tools, such as rods. Typically, more than one perming tool
or rod is used to provide a plurality of curls in the hair,
typically throughout all of the hair on the head.
[0254] Optionally, prior to wrapping/rolling the hair on a rod or
perming tool, the hair is washed with a shampoo or clarifying
shampoo and is towel dried.
[0255] The amount of formulation applied is preferably an amount
that saturates the hair on the rods or perming tools. The hair is
allowed to set for a given period of time ("setting period").
Preferably, no application of heat is required during the setting
period. The setting period can be in the range of about 1 to 90
minutes, more preferably about 10, 20, 30, or 40 minutes, even more
preferably 30 minutes after the application of the formulation. In
some instances, the setting period can be in the range of about 15
to 30 minutes, more preferably about 20 minutes.
[0256] After the setting period has concluded, such as after a 30
minute-long setting period, the hair is rinsed followed by removal
of the rod(s) or perming tool(s) from the hair. Alternatively,
after the setting period, the rod(s) or perming tool(s) are removed
from the hair, and subsequently the hair is rinsed. The rinsed hair
is typically subsequently shampooed and, optionally,
conditioned.
EXAMPLES
Example 1
Curling of Asian Hair
[0257] Composition of Formulations 1 and 2:
[0258] Formulation 1 contained 2 wt % NaOH and 2 wt %
Bis-Aminopropyl Diglycol Dimaleate with the remainder of the
formulation being made up of water.
[0259] Formulation 2 contained 4 wt % Bis-Aminopropyl Diglycol
Dimaleate with the remainder of the formulation being made up of
water.
[0260] Curling Procedure:
[0261] Formulation 1 was prepared immediately prior to use, applied
to a swatch of Asian hair in a perm roller, and allowed to sit on
the hair for 20 minutes. The hair sample was then thoroughly rinsed
with room temperature water for 3 minutes and then blotted with a
paper towel. Formulation 2 was added to the hair sample and allowed
to sit for 20 minutes. The hair sample was then rinsed, removed
from the roller, shampooed and conditioned, and allowed to air
dry.
[0262] Curling Results: The hair retained a curl and exhibited a
better condition, as compared to the hair prior to treatment, such
as increased smoothness and shine.
[0263] Curl retention was tested after 20 wash cycles including
shampooing and conditioning. After 20 wash cycles, the curl
retention was nearly identical to the curl after the initial
treatment.
Example 2
Curling of Asian Hair
[0264] Composition of Formulations 1 and 2:
[0265] Formulation I contained 2 wt % NaOH with the remainder of
the formulation being made up of water.
[0266] Formulation 2 contained 4 wt % Bis-Aminopropyl Diglycol
Dimaleate with the remainder of the formulation being made up of
water.
[0267] Curling Procedure:
[0268] Two swatches of Asian hair were rolled into perm rollers and
each swatch was treated with Formulation 1 for 20 minutes. Both
hair swatches were then rinsed for 3 minutes and blotted with a
paper towel. One of the swatches was then treated with Formulation
2 for 20 minutes and the other swatch was treated with a 5 wt %
acetic acid aqueous solution for 20 minutes. Both swatches were
then rinsed, removed from the perm rollers, shampooed and
conditioned, and allowed to air dry.
[0269] Curling Results:
[0270] The hair swatch neutralized with Formulation 2 demonstrated
curl retention but was in worse condition than prior to the
treatment and in significantly inferior condition, when compared to
the swatch treated according to the conditions listed in Example 1
(above).
[0271] The sample neutralized with the acetic acid solution did not
hold a curl and was significantly damaged and in a worse state than
the swatch neutralized by Formulation 2.
Example 3
Curling of Caucasian Hair
[0272] Composition of Formulations 1 and 2:
[0273] Formulation 1 contained 2 wt % NaOH and 4 wt %
Bis-Aminopropyl Diglycol Dimaleate with the remainder of the
formulation being made up of water.
[0274] Formulation 2 contained 4 wt % Bis-Aminopropyl Diglycol
Dimaleate with the remainder of the formulation being made up of
water.
[0275] Curling Procedure:
[0276] Formulation 1 prepared immediately prior to use, applied
to
[0277] Caucasian hair in a perm roller, and allowed to sit on the
hair for 20 minutes. The hair sample was then thoroughly rinsed in
room temperature water for 3 minutes and blotted with a paper
towel. Formulation 2 was added to the hair sample and allowed to
sit for 20 minutes. The hair sample was then rinsed, removed from
the perm roller, shampooed and conditioned, and allowed to air
dry.
[0278] Curling Results:
[0279] The treated hair retained curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 4
Curling of Caucasian Hair
[0280] Composition of Formulations 1 and 2:
[0281] Formulation 1 contained 2.6 wt % NaOH and 4 wt %
Bis-Aminopropyl Diglycol Dimaleate with the remainder of the
formulation being made up of water.
[0282] Formulation 2 contained Bond Protector No. 2 (OLAPLEX.RTM.)
(3 wt % Bis-Aminopropyl Diglycol Dimaleate in the form of
cream).
[0283] Curling Procedure:
[0284] Formulation 1 was prepared immediately prior to use, applied
to Caucasian hair in a perm roller, and allowed to sit on the hair
for 40 minutes. The hair sample was then thoroughly rinsed in room
temperature water for 3 minutes and blotted with a paper towel.
Formulation 2 was applied to the hair sample and allowed to sit on
the hair for 10 minutes. The hair sample was then rinsed, removed
from the perm roller, shampooed and conditioned, and allowed to air
dry.
[0285] Curling Results:
[0286] The treated hair retained curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 5
Curling of Asian Hair
[0287] Composition of Formulations 1 and 2:
[0288] Formulation 1 contained 2.6 wt % NaOH and 2 wt % Bis-
Aminopropyl Diglycol Dimaleate with the remainder of the
formulation being made up of water.
[0289] Formulation 2 contained Bond Protector No. 2 (OLAPLEX.RTM.)
(3 wt % Bis-Aminopropyl Diglycol Dimaleate in the form of
cream).
[0290] Curling Procedure:
[0291] Formulation 1 was prepared immediately prior to use, applied
to Asian hair in a perm roller, and allowed to sit on the hair for
40 minutes. The hair sample was then thoroughly rinsed in room
temperature water for 3 minutes and blotted with a paper towel.
Formulation 2 was applied to the hair and allowed to sit on the
hair for 10 min The hair sample was then rinsed, removed from the
roller, shampooed and conditioned, and allowed to air dry.
[0292] Curling Results:
[0293] The treated hair retained curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 6
Curling of Caucasian Hair
[0294] Composition of Formulation 1:
[0295] Formulation 1 contained 6.6 wt % NaOH and 1.25 wt %
Bis-Aminopropyl Diglycol Dimaleate with the remainder of the
formulation being made up of water.
[0296] Curling Procedure:
[0297] Formulation 1 was prepared immediately prior to use, applied
to Caucasian hair in a perm roller, and allowed to sit on the hair
for 40 minutes. The hair sample was then rinsed, removed from the
perm roller, shampooed and conditioned, and allowed to air dry.
[0298] Curling Results:
[0299] The treated hair retained a curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 7
Curling of Asian Hair
[0300] Composition of Formulation 1:
[0301] Formulation 1 contained 6.6 wt % NaOH and 0.77 wt % Maleic
Acid with the remainder of the formulation being made up of
water.
[0302] Curling Procedure:
[0303] Formulation 1 was prepared immediately prior to use, applied
to Asian hair in a perm roller, and allowed to sit on the hair for
30 minutes. The hair sample was then rinsed, removed from the
roller, shampooed and conditioned, and allowed to air dry.
[0304] Curling Results:
[0305] The treated hair retained a curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 8
Curling of Caucasian Hair
[0306] Composition of Formulation 1:
[0307] Formulation 1 contained 6.6 wt % NaOH and 0.7 wt %
Methacrylic Acid with the remainder of the formulation being made
up of water.
[0308] Curling Procedure:
[0309] Formulation 1 was prepared immediately prior to use, applied
to Asian hair in a perm roller, and allowed to sit on the hair for
30 minutes. The hair sample was then rinsed, removed from the
roller, shampooed and conditioned, and allowed to air dry.
[0310] Curling Results:
[0311] The treated hair retained a curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 9
Curling of Caucasian Hair
[0312] Composition of Formulation 1:
[0313] Formulation 1 contained 6.6 wt % NaOH and 0.7 wt %
Methacrylic Acid with the remainder of the formulation being made
up of water.
[0314] Curling Procedure:
[0315] Formulation 1 was prepared immediately prior to use, applied
to Asian hair in a perm roller, and allowed to sit on the hair for
30 minutes. The hair sample was then rinsed, removed from the
roller, shampooed and conditioned, and allowed to air dry.
[0316] Curling Results:
[0317] The treated hair retained a curl and exhibited a better
condition, as compared to the hair prior to treatment, such as
increased smoothness and shine. Curl retention was tested after 10
wash cycles including shampooing and conditioning. After 10 wash
cycles, the curl retention was nearly identical to the curl after
the initial treatment.
Example 10
Curling of Caucasian Hair Without Active Agent
[0318] Composition of Formulation 1:
[0319] Formulation 1 contained 6.6 wt % NaOH and 0.7 wt % Lactic
Acid with the remainder of the formulation being made up of
water.
[0320] Curling Procedure:
[0321] Formulation 1 was prepared immediately prior to use, applied
to Asian hair in a perm roller, and allowed to sit for 30 minutes.
The hair sample was then rinsed, removed from the roller,
shampooed, and conditioned and allowed to air dry.
[0322] Curling Results:
[0323] The treated hair did not retain any significant curl after 1
wash and after 3 wash cycles had less curl than before the
treatment. The condition, as compared to the hair prior to
treatment, was flat with increased frizz, breakage, and poor
feel.
* * * * *