U.S. patent application number 17/406609 was filed with the patent office on 2022-07-14 for keratin treatment formulations and methods.
The applicant listed for this patent is Olaplex, Inc.. Invention is credited to Craig J. Hawker, Eric D. Pressly.
Application Number | 20220218579 17/406609 |
Document ID | / |
Family ID | |
Filed Date | 2022-07-14 |
United States Patent
Application |
20220218579 |
Kind Code |
A1 |
Pressly; Eric D. ; et
al. |
July 14, 2022 |
KERATIN TREATMENT FORMULATIONS AND METHODS
Abstract
Formulations, kits, and methods for rebuilding the disulfide
bonds in keratin found in hair, skin, or nails. Hair that is
damaged due to a hair coloring treatment and/or other reducing
treatment, such as during a permanent wave, can be treated with the
formulations containing one or more active agents. The formulations
may be applied subsequent to a hair coloring treatment or
simultaneously with a hair coloring treatment. Use of the active
agent formulations during a permanent wave treatment prevents the
reversion of the hair to its previous state, for at least one week,
preferably at least three months, more preferably at least one
year, most preferably greater than one year, after one or more than
one application of the formulation. Application of the active agent
formulation to skin or nails can help repair damaged disulfide
bonds due to natural wear and tear or natural aging.
Inventors: |
Pressly; Eric D.; (Santa
Barbara, CA) ; Hawker; Craig J.; (Santa Barbara,
CA) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Olaplex, Inc. |
Boston |
MA |
US |
|
|
Appl. No.: |
17/406609 |
Filed: |
August 19, 2021 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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16556678 |
Aug 30, 2019 |
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17406609 |
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15290593 |
Oct 11, 2016 |
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16556678 |
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15087415 |
Mar 31, 2016 |
9498419 |
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15290593 |
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14713885 |
May 15, 2015 |
9326926 |
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15087415 |
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61994709 |
May 16, 2014 |
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International
Class: |
A61K 8/362 20060101
A61K008/362; A61K 8/36 20060101 A61K008/36; A61K 8/46 20060101
A61K008/46; A61Q 5/04 20060101 A61Q005/04; A61Q 5/12 20060101
A61Q005/12; A61Q 5/08 20060101 A61Q005/08; A61Q 5/10 20060101
A61Q005/10; A61K 8/41 20060101 A61K008/41; A45D 7/04 20060101
A45D007/04; A61Q 5/02 20060101 A61Q005/02; A61K 8/06 20060101
A61K008/06; A61K 8/34 20060101 A61K008/34; A61K 8/42 20060101
A61K008/42; A61K 8/84 20060101 A61K008/84 |
Claims
1-29. (canceled)
30. A method of treating hair, the method comprising the steps of:
(i) applying a first formulation comprising a reducing agent to
hair; and (ii) applying a second formulation comprising an active
agent to the hair, wherein the active agent has the formula:
##STR00007## wherein Z is a linker or is absent; m and n are each
an integer independently selected from 1-6, and the sum of m+n is
equal to or greater than 2; B is a functional group capable of
forming a covalent bond with a nucleophile; and A is an ionizable
functional group.
31. The method of claim 30, wherein method of treating hair is a
hair waving and/or hair curling method and the method further
includes a step of setting the hair on rods.
32. The method of claim 30, wherein method of treating is a hair
straightening method.
33. The method of claim 30, wherein B is independently selected
from the group consisting of: ##STR00008## wherein R is
independently selected from the group consisting of hydrogen,
C.sub.1-6 alkyl groups, aryl groups, or an ionizable functional
groups; 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; and A is independently
selected from the group consisting of: --COOH, --SO.sub.3H,
--PO.sub.3H.sub.2, --N(R.sup.1).sub.2, --N(R.sup.1).sub.3; wherein
R.sup.1 is independently selected from the group consisting of a
hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl,
heterocycloalkyl and heteroaryl groups; wherein each R.sup.1 is
independently unsubstituted or substituted with one or more
substituents.
34. The method of claim 30, wherein the linker Z is an alkyl group,
alkenyl group, cycloalkyl group, cycloalkenyl group, aryl group,
heterocycloalkyl group, or heteroaryl group, wherein the alkyl,
alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or
heteroaryl group, is unsubstituted or substituted one or more times
by a halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl,
cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy,
oxo, formyl, acyl, carboxylic acid, --C(O)R.sup.1, --C(O)OR.sup.1,
--COO.sup.-, primary amide, 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 ,
--S(O).sub.2NR.sup.1R.sup.2, --SOR.sup.1, or --SOOR.sup.1; wherein
R.sup.1 and R.sup.2 are each independently selected from the group
consisting of a hydrogen, alkyl group, alkenyl group, alkynyl
group, cycloalkyl group, aryl group, heterocycloalkyl , and
heteroaryl group, wherein each of R.sup.1 and R.sup.2 is
independently unsubstituted or substituted with one or more
substituents.
35. The method of claim 30, wherein the active agent is selected
from the group consisting of: ##STR00009##
36. The method of claim 30, wherein the active agent is present in
an amount ranging from about 1 wt % to about 10 wt % of the second
formulation, optionally from about 0.5 to 3 wt % of the second
formulation.
37. The method of claim 30, wherein the reducing agent is selected
from the group consisting of thioglycolic acid, thiolactic acid,
dihydrolipoate, thioglycerol, mercaptopropionic acid, sodium
bisulfite, ammonium bisulfide, zinc formaldehyde sulfoxylate,
sodium formaldehyde sulfoxylate, sodium metabisulfite, potassium
borohydride, pegylated thiols, and hydroquinone.
38. The method of claim 30, further comprising: (iii) applying an
aqueous oxidizing solution comprising hydrogen peroxide to the
hair, wherein step (iii) occurs subsequent to steps (i) and
(ii).
39. The method of claim 30, wherein the second formulation further
comprises one or more cosmetically acceptable excipients selected
from the group consisting of water, surfactants, vitamins, natural
extracts, preservatives, chelating agents, perfumes, preservatives,
antioxidants, proteins, amino acids, humectants, fragrances,
emollients, penetrants, thickeners, viscosity modifiers, hair
fixatives, film formers, emulsifiers, opacifying agents,
propellants, liquid vehicles, carriers, salts, pH adjusting agents,
neutralizing agents, buffers, hair conditioning agents, anti-static
agents, anti-frizz agents, anti-dandruff agents, and combinations
thereof.
40. The method of claim 39, wherein the one or more cosmetically
acceptable excipients are present in an amount ranging from about
40 wt % to about 99 wt % of the second formulation.
41. The method of claim 30, wherein following step (ii) breakage of
the hair is decreased by at least about 5%, 10%, 20%, 40%, or 50%,
as compared to the hair of an individual treated with the second
formulation in the absence of the active agent.
42. A hair spray comprising a hair repair formulation, the hair
repair formulation comprising: an active agent having the formula:
##STR00010## wherein Z is a linker or is absent; m and n are each
an integer independently selected from 1-6, and the sum of m+n is
equal to or greater than 2; B is a functional group capable of
forming a covalent bond with a nucleophile; A is an ionizable
functional group; a cosmetically acceptable carrier; and an
optional propellant.
43. The hair spray of claim 42, wherein the cosmetically acceptable
carrier is water or a mixture of water and an alcohol.
44. The hair spray of claim 42, wherein the hair repair formulation
comprises an antioxidant, fragrance, preservative, sunscreen agent,
anti-static agent, vitamin, protein, peptide, plant extract,
humectant, oil, emollient, lubricant, thickener, hair conditioning
agent, polymer, and/or surfactant.
45. The hair spray of claim 42, wherein the propellant is present
and selected from the group consisting of a liquefiable gas
propellant, a halogenated propellant, a dimethyl ether propellant,
a hydrocarbon propellant (such as propane, n-butane, iso-butane),
CFC-replacement propellants, compressed air, and combinations
thereof.
46. The hair spray of claim 42, wherein B is independently selected
from the group consisting of: ##STR00011## wherein R is
independently selected from the group consisting of hydrogen,
C.sub.1-6 alkyl groups, aryl groups, or an ionizable functional
groups; 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; and A is independently
selected from the group consisting of: --COOH, --SO.sub.3H,
--PO.sub.3H.sub.2, --N(R.sup.1).sub.2, --N(R.sup.1).sub.3; wherein
R.sup.1 is independently selected from the group consisting of a
hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl,
heterocycloalkyl and heteroaryl groups; wherein each R.sup.1 is
independently unsubstituted or substituted with one or more
substituents.
47. The hair spray of claim 42, wherein the linker Z is an alkyl
group, alkenyl group, cycloalkyl group, cycloalkenyl group, aryl
group, heterocycloalkyl group, or heteroaryl group, wherein the
alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl,
or heteroaryl group, is unsubstituted or substituted one or more
times by a halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl,
cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy,
oxo, formyl, acyl, carboxylic acid, --C(O)R.sup.1, --C(O)OR.sup.1,
--COO.sup.-, primary amide, 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 ,
--S(O).sub.2NR.sup.1R.sup.2, --SOR.sup.1, or --SOOR.sup.1; wherein
R.sup.1 and R.sup.2 are each independently selected from the group
consisting of a hydrogen, alkyl group, alkenyl group, alkynyl
group, cycloalkyl group, aryl group, heterocycloalkyl , and
heteroaryl group, wherein each of R.sup.1 and R.sup.2 is
independently unsubstituted or substituted with one or more
substituents.
48. The hair spray of claim 41, wherein the active agent is
selected from the group consisting of: ##STR00012##
49. A hair coloring kit comprising: (a) a first formulation
comprising a hair coloring agent and a reducing agent capable of
reducing disulfide bonds in hair to produce free thiol groups, and
(b) a second formulation comprising an active agent, wherein the
active agent has the formula: ##STR00013## wherein Z is a linker or
is absent; m and n are each an integer independently selected from
1-6, and wherein the sum of m+n is equal to or greater than 2; B is
a functional group capable of forming a covalent bond with a
nucleophile; and A is an ionizable functional group.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority to U.S. Provisional
Application Ser. No. 61/994,709, filed May 16, 2014, the disclosure
of which is incorporated herein by reference in its entirety.
FIELD OF THE INVENTION
[0002] The present invention generally relates to formulations and
methods for treating keratin in hair, skin, or nails, and in
particular for strengthening and/or repairing hair during or after
a coloring or permanent wave treatment.
BACKGROUND OF THE INVENTION
[0003] Hair coloring is currently a globally accepted fashion
phenomenon. Color treatments include hair coloring, highlighting,
and bleaching. The coloring products can be categorized in several
types, which include permanent, demi-permanent, semi-permanent, and
temporary coloring formulations. Permanent hair coloring products
make up the majority of the market worldwide.
[0004] Significant effort has been directed towards developing
various approaches to hair dyeing; these include, oxidative dyes,
direct action dyes, natural dyes, metallic dyes and reactive dyes.
Many hair coloring formulations, in particular permanent coloring
formulations, use reducing agents to break the disulfide bonds in
the hair allowing deeper penetration of the hair coloring dyes and
bleaching agents into the hair.
[0005] Disulfide bond linkages in hair are also broken by
application of reducing agents, such as during permanent wave and
hair straightening process. After the disulfide bonds are broken,
the hair is placed in stress to establish the final style (e.g.,
straight, wavy, or curly), and the disulfide bonds are
re-established.
[0006] Thioglycolic acid, particularly as the ammonium salt, is
often used to cleave the cysteine disulfide bonds present in hair.
Sodium bisulfite is another example of a known reducing agent
commonly used in various dyes and bleaching agents in color
treatments.
[0007] Typically, oxidation to restore the reduced bond is
partially obtained when an oxidizing agent, such as hydrogen
peroxide is present in a coloring formulation and/or by exposing
the hair to atmospheric oxygen. However, this oxidation step can be
very slow and can leave the hair frizzy and damaged.
[0008] Similarly, hair undergoing a permanent wave treatment is
typically treated with a reducing agent followed by an oxidizing
agent. Hydrogen peroxide is optionally added in a second step to
restore the hair to its prior state. The newly formed disulfide
bonds of the treated hair are under stress to maintain the hair's
new shape; thus, they break easily resulting in a reversion of the
hair style over time.
[0009] The use of peroxides in the hair styling process can result
in damaged hair, removal of non-natural color from the hair, and/or
leave the hair frizzy. Furthermore, some latent reduced thiols may
remain in the hair even after oxidative treatment. Hair styling
treatments with peroxides involve the following reaction with thiol
groups:
2 K--S--H+H.sub.2O.sub.2.fwdarw.K--S--S--K+2 H.sub.2O (Reaction
I)
[0010] where K represents keratin in the hair.
[0011] In the case where two K--S--H groups are not present for
Reaction I to take place, it is believed that the following
reaction takes place, which results in damaged hair:
K--S--H+H.sub.2O.sub.2.fwdarw.K--SO.sub.2--OH (Reaction II).
[0012] In addition to being a major component in hair, keratin is
also a major component in skin and nails. There are a number of
different types of keratin and they are generally grouped as soft
or hard keratins. Soft keratins are more prevalent in skin, while
hard keratins predominate in hair and nails. Nails, in particular,
are made of a modified keratin similar to that found hair. The
disulfide bonds of the keratin in nails contribute to their
impermeability. Therefore, damage to the disulfide bridges of
keratin present in skin or nails can result in unhealthy and/or
flaky skin or nails. Maintaining the disulfide bridges of keratin
therefore helps to keep skin healthy and prevents cracking and
splitting in nails.
[0013] Substantial improvement is needed in the areas of color
saturation, color development, precise initial color consistency,
improved wash fastness, and improved hair conditioning when
applying color treatments. For example, the attainment of precise
initial colors that are retained by the hair for a desirable time
period has remained an elusive goal. The coloring formulations also
cause severe hair damage, especially when coloring treatments are
repeated. Moreover, various standard daily actions to the hair, for
example hair brushing, hair blow-drying, and sun light exposure can
cause even more damage to the hair.
[0014] Similar damage to the hair can also result from permanent
wave treatments. In both coloring and permanent wave processes,
improvements are also needed to repair damage and/or to strengthen
the hair during or after such styling treatments. Additionally,
improved treatments and methods are needed which can be applied to
skin and nails to repair damaged keratin.
[0015] There is a need for hair formulations and treatments that
repair and/or strengthen keratin in hair damaged from coloring
and/or permanent wave treatments using reducing treatments.
[0016] There is also a need for hair formulations and treatments
that can repair latent reduced thiols present in hair.
[0017] There is also a need for formulations and treatments that
can repair damage to keratin present in skin and hair.
[0018] Therefore, it is an object of this invention to provide
improved formulations and methods for repairing and/or
strengthening damaged hair.
[0019] It is also an object of this invention to provide methods
for using formulations that repair and/or strengthen hair after
and/or during coloring or permanent wavetreatments.
[0020] It is also an object of this invention to provide
formulations and methods for using these formulations to repair
and/or strengthen hair after a reducing treatment.
[0021] It is also an object of this invention to provide
formulations and methods for using these formulations that repair
and/or strengthen keratin in hair, skin or nails due to natural
wear and tear or due to natural aging.
SUMMARY OF THE INVENTION
[0022] Formulations, kits, and methods for restoring hair that has
been broken during a hair coloring or permanent wave treatment are
disclosed. The formulations have similar benefits when used with
different color chemical processes, such as bleaching, highlights,
lowlights, semi-permanent, demi-permanent, and permanent color.
Improved methods of styling hair, for example permanent hair waving
and hair curling are also provided. The formulations can be applied
each time the hair is washed or daily, once-weekly, twice-weekly,
biweekly, once-monthly, every other month, or at less frequent
intervals. Preferably, the formulations are applied once-monthly to
achieve the desired results.
[0023] Traditional methods of permanent hair waving, hair curling,
or straightening use hydrogen peroxide after a reducing treatment.
The process generally takes about three days to complete. The
methods disclosed herein use active agents to repair the hair;
these active agents are washed from the individual's hair on the
same day that they are applied to the hair. Under the same
conditions, such as temperature and moisture, hair treated with the
formulations disclosed herein takes a longer time to revert to its
prior state as compared to the same hair that is treated with
hydrogen peroxide.
[0024] The formulations disclosed herein contain one or more
polyfunctional compounds. The polyfunctional compound contains at
least one ionizable functional group capable of forming ionic
bonds, and the polyfunctional compound also contains at least one
functional group capable of forming a covalent bond with a thiol
group. In some embodiments, the polyfunctional compounds contains
at least two ionizable groups. Optionally, the formulation is
applied at the same time as the hair coloring or permanent wave
treatment. Alternatively, the formulation may be applied after the
hair coloring or permanent wave treatment or to damaged hair. For
example, the formulations can be applied within one week of the
hair being treated and/or damaged, preferably within three days,
more preferably within two days, most preferably immediately after
application of the coloring or permanent wave treatment.
DETAILED DESCRIPTION OF THE INVENTION
I. Definitions
[0025] 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.
[0026] "Pharmaceutically acceptable" and "cosmetically acceptable"
are used interchangeably and refer to those compounds, materials,
and/or 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, pharmaceutically
acceptable refers to a material, compound, or formulation that is
suitable for use in contact with the skin, scalp, or hair.
Pharmaceutically acceptable materials are known to those of
ordinary skill in the art.
[0027] "Shampoo", as used herein, generally refers to a liquid or
semi-solid formulation applied to hair that contains detergent or
soap for washing the hair.
[0028] "Conditioner", as used herein, generally refers to a
formulation (e.g., liquid, cream, lotion, gel, semi-solid) applied
to hair to soften the hair, smooth the hair, and/or change the
sheen of the hair.
[0029] "Analog" and "derivative" are used herein 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, or
a combination 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 formed, at least
theoretically, from the parent compound via chemical and/or
physical processes.
[0030] "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.
[0031] "Nucleophilic group" or "nucleophilic moiety" are used
interchangeably and refer to one or more functional groups or
moieties that are electron rich and are capable of reacting with
electrophilic groups.
[0032] "Michael acceptor", as used herein, 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.
[0033] "Carboxylic acid," as used in here refers to the group
--COOH. Unless specified otherwise the term carboxylic acid
embraces both the free acid and carboxylate salt.
[0034] "Alkyl", as used herein, 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.
[0035] The term "alkyl" includes both "unsubstituted alkyls" and
"substituted alkyls", the latter of which refers to alkyl moieties
having one or more substituents replacing a 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, sulthydryl, alkylthio,
sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl,
aralkyl, or an aromatic or heteroaromatic moiety.
[0036] Unless the number of carbons is otherwise specified, "lower
alkyl" as used herein 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.
[0037] 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.
[0038] "Alkenyl" and "Alkynyl", as used herein, 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.
[0039] "Aryl", as used herein, 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.
[0040] "Alkylaryl", as used herein, refers to an alkyl group
substituted with an aryl group (e.g., an aromatic or hetero
aromatic group).
[0041] "Heterocycle" or "heterocyclic", as used herein, 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, benztriazolyl, 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.
[0042] "Heteroaryl", as used herein, 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,
particularly a benz-derivative or one 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.
[0043] "Halogen", as used herein, refers to fluorine, chlorine,
bromine, or iodine.
[0044] The term "substituted," as used herein, 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.
[0045] 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. It is understood that "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, i.e. a compound that does not spontaneously undergo
transformation such as by rearrangement, cyclization, elimination,
etc.
[0046] "Polymer", as used herein, refers to a molecule containing
more than 10 monomer units.
[0047] "Water-soluble", as used herein, generally means at least
50, 75, 100, 125, 150, 200, 225, or 250 g is soluble in 1L of water
at 25.degree. C.
II. Formulations
[0048] The formulations and methods disclosed herein are concerned
with treating keratin in hair, skin, or nails. In one embodiment,
the methods relate to strengthening and/or repairing hair after it
has undergone a coloring treatment or after or during a permanent
wave treatment. Additionally, the formulations may reduce or
prevent hair damage due to hair coloring and/or bleaching
processes.
[0049] A. Formulations
[0050] The formulations contain one or more polyfunctional
compounds (also referred to herein as "active agents").
[0051] The active agents can be combined with one or more
pharmaceutically acceptable carriers and/or excipients that are
considered safe and effective to human hair and/or 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 similar adverse reactions. The formulations may
further contain an excipient that renders the formulations neutral
pH, or a pH ranging from about pH 3 to about pH 12, preferably from
pH 5 to pH 8.
[0052] The active agent is typically present in an amount ranging
from about 0.01 wt % to about 50 wt % of the formulation,
preferably from about from about 1 wt % to about 25 wt % of the
formulation, more preferably from about 1 wt % to about 15 wt %,
most preferably from about 1 wt % to about 10 wt %. Typically, the
active agent may be present in an amount ranging from about 0.5 to
about 3 wt % of the formulation, or from about 1 to about 3 wt % of
the formulation.
[0053] 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 6 to 8 and 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 compound is unchanged over the specified
period.
[0054] a. Active Agents
[0055] The active agent is a polyfunctional compound that may
contain ionizable functional groups capable of forming ionic bonds
and functional groups capable of forming a covalent bond with a
thiol. Suitable ionizable functional groups include, but are not
limited to, acidic groups such as carboxylic acids, sulfonic acids,
phosphonic acids, and basic groups, such as amines Suitable
functional groups capable of forming a covalent bond with a thiol
include, but are not limited to, Michael acceptors, alkyl halides
or sulfonate esters.
[0056] The active agent may have the following Formula I:
##STR00001##
wherein Z is a linker or is absent, m and n are each an integer
independently selected from 0-6, provided that m+n is at least 2, B
is a functional group capable of forming a covalent bond with a
thiol, and A is an ionizable functional group. In some embodiments,
ionizable group A can be independently selected from the group
consisting of: --COOH, --SO.sub.3H, --PO.sub.3H.sub.2, and
--N(R.sup.1).sub.2; wherein R.sup.1 is independently selected from
the group consisting of a hydrogen, alkyl, alkenyl, alkynyl,
cycloalkyl, aryl, heterocycloalkyl and heteroaryl groups; wherein
each R.sup.1 is independently unsubstituted or substituted with one
or more substituents. In some other embodiments, ionizable group A
can be an ionic group, such as --N.sup.+(R.sup.1).sub.3. In some
preferred embodiments, each R.sup.1 is independently selected from
a methyl, ethyl, or isopropyl group.
[0057] Exemplary active agents according to Formula I may contain
thiol reactive functional groups, as group B, for example, such as
those shown in the following moieties:
##STR00002##
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.
[0058] 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.
[0059] 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 (e.g., --CONHR.sub.11),
--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.sub.1), and sulfonyl group (e.g.,
--SOOR.sub.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.
[0060] 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.
[0061] In some embodiments, the active agent of Formula I has one
of the following structures:
##STR00003##
or is a simple salt of these structures.
[0062] In certain other embodiments, the active agent may have the
following Formula II:
##STR00004##
[0063] wherein Z is a linker or is absent, m and n are each an
integer independently selected from 0-6, provided that m+n is at
least 2, B is a functional group capable of forming a covalent bond
with a nucleophile, such as but not limited to a thiol or amine
group, A is an ionizable functional group as defined above, and C
contains an ionic group and a functional group which is also
capable of forming a covalent bond with a nucleophile, such as but
not limited to a thiol or amine group, 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 0-6, such that the sum of
charges of group C and ionizable group A is zero. In some
embodiments, ionizable group A can be independently selected from
the group consisting of: --COOH, --SO.sub.3H, --PO.sub.3H.sub.2,
and --N(R.sup.1).sub.2; wherein R.sup.1 is independently selected
from the group consisting of a hydrogen, alkyl, alkenyl, alkynyl,
cycloalkyl, aryl, heterocycloalkyl and heteroaryl groups; wherein
each R.sup.1 is independently unsubstituted or substituted with one
or more substituents. In some other embodiments, ionizable group A
can be an ionic group such as --N.sup.+(R.sup.1).sub.3. In some
preferred embodiments, each R.sup.1 is independently selected from
a methyl, ethyl, or isopropyl group.
[0064] The 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:
##STR00005##
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.
[0065] 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.
[0066] 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 (e.g., --CONHR.sup.1),
--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.sub.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.
[0067] 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.
[0068] Group C is an ionic group ionically bonded to ionizable
group A and contains at least one thiol reactive selected from 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.
[0069] In some embodiments, the active agent of Formula II has one
of the following structures:
##STR00006##
[0070] b. Excipients
[0071] The formulations typically contain one or more cosmetically
acceptable excipients. Cosmetically acceptable excipients include,
but are not limited to 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.
[0072] The formulations typically contain at least two cosmetically
acceptable excipients. In some foul's, the formulations contain the
active agent, water, and optionally a preservative and/or
fragrance.
[0073] The formulation for treating hair 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 hair care formulation depending on the form of use of the
formulation (e.g., hair spray, cream, conditioner, or shampoo).
[0074] The pharmaceutical excipient is 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 %.
[0075] i. Surfactants
[0076] Surfactants are surface-active agents that are able to
reduce the surface tension of water and cause the hair formulation
to slip across or onto the skin or hair. Surfactants also include
detergents and 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.
[0077] 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.
[0078] More than one surfactant may be included in the
formulation.
[0079] 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.
[0080] ii. Emollients
[0081] 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 combinations thereof.
More than one emollient may be included in the formulation.
[0082] 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.
[0083] iii. Emulsifiers
[0084] The formulation 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, polysorbate-80, or combinations
thereof. More than one emulsifier may be included in the
formulation.
[0085] The emulsifier is optionally included in an amount ranging
from about 0.05%-15% by weight of the formulation, preferably from
about 0.1%-10% by weight of the formulation.
[0086] iv. Preservatives
[0087] One or more preservatives may be included in the
formulation. 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, Formaldahyde, 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).
[0088] 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.
[0089] v. Conditioning Agents
[0090] One or more conditioning agents may be included in the
formulation. 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.
[0091] The conditioning agent(s) 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.
[0092] vi. Diluents
[0093] Diluent, as used herein, refers to a substance(s) that
dilutes the active agent. Water is the preferred diluent. The
formulation typically contains greater than one percent (by wt)
water, preferably greater than five percent (by wt) water, more
preferably greater than 50% (by wt) water, and most preferably
greater than 80% (by 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 penetration and/or
reduce odor.
[0094] vii. Viscosity Modifying Agents
[0095] The formulations may contain one or more viscosity modifying
agents, such as viscosity increasing agents. Classes of such agents
include, but are not limited to, viscous liquids, such as
polyethylene glycol, semisythetic 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, 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.
[0096] viii. Antioxidants
[0097] The formulation 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.
[0098] ix. Opacifying Agents
[0099] The formulation may contain one or more opacifying agents.
Opacifying agents are added to the formulations to make it opaque.
Suitable opacifying agents include, but are not limited to, glycol
distearate and ethoxylated fatty alcohols.
[0100] c. Forms of the Formulation
[0101] i. Sprays
[0102] The formulation may be in the forms of a spray. The spray
typically includes the active agent and a cosmetically acceptable
carrier. In some embodiments, the carrier is water or a water and
alcohol mixture. The spray formulation optionally includes an
antioxidant, sunscreen agent, vitamin, protein, peptide, plant
extract, humectant, oil, emollient, lubricant, thickener, hair
conditioning agent, polymer, and/or surfactant. Preferably, the
spray formulation includes a preservative. In some embodiments, the
formulation includes a fragrance. In some embodiments, the
formulation includes a surfactant. In some embodiments, the
formulation contains water, fragrance, a preservative, and an
active agent. In some embodiments, the formulation contains water,
fragrance, a preservative, and an active agent. In some
embodiments, the formulation contains water, a preservative,
fragrance, an active agent, and an anti-static agent. In some
embodiments, the formulation contains water, a preservative,
fragrance, an active agent, and a hair conditioning agent. In some
embodiments, the formulation contains water, a preservative,
fragrance, an active agent, and a surfactant.
[0103] The hair spray formulations may be dispensed from containers
that include aerosol dispensers or pump spray dispensers. Such
dispensers are known in the art and are commercially available from
a variety of manufacturers.
[0104] Propellant
[0105] When the hair spray formulation is dispensed from a
pressurized aerosol container, a propellant may be used to force
the formulation out of the container. Suitable propellants include,
but are not limited to, a liquefiable gas or a halogenated
propellant. Examples of suitable propellants include dimethyl ether
and hydrocarbon propellants such as propane, n-butane, iso-butane,
CFCs, and CFC-replacement propellants. The propellants may be used
singly or admixed.
[0106] The amount of propellant may range from about 10% to about
60% by weight of the formulation. The propellant may be separated
from the hair repair formulation as in a two compartment container.
Other suitable aerosol dispensers are those characterized by the
propellant being compressed air, which can be filled into the
dispenser using a pump or equivalent device prior to use.
Conventional non-aerosol pump spray dispensers, i.e., atomizers,
may also be used to apply the formulation to the hair.
[0107] ii. Conditioners
[0108] The formulation may be in the form of a conditioner. The
conditioner typically includes the active agent in a suitable
carrier. Additionally, the conditioner may include cationic
polymers derived from polysaccharides, for example cationic
cellulose derivatives, cationic starch derivatives, cationic guar
derivatives and cationic locust bean gum derivatives, synthetic
cationic polymers, mixtures or combinations of these agents. The
formulation may comprise other synthetic or natural polymers or
polymers derived from biological preparation processes, which are
functionalized, where appropriate, for example with cationic or
neutral groups. These polymers may have a stabilizing or
strengthening action on the formulation, and/or a conditioning
action (deposition on the surface of the skin or the hair).
[0109] The active agent may be included in any suitable
concentration. Typical concentrations of active agent in the
conditioner range from small amounts such as approximately 0.01%
(by wt), preferably at least 0.1% (by wt), to large amounts, such
as up to 50% (by wt). Preferably the conditioner contains the
active agent in a concentration ranging from 0.1% (by wt) to 5% (by
wt), more preferably from 0.1% wt to 3% (by wt). While greater
concentrations of active agent could be present in the conditioner,
they are generally not needed to achieve the desired results.
[0110] iii. Shampoos
[0111] The hair repair formulation may be in the form of a shampoo.
The shampoo typically includes the active agent in a suitable
carrier. The active agent may be included in any suitable
concentration. Typical concentrations of the active agent in the
shampoo range from small amounts such as approximately 0.01% (by
wt), preferably at least 0.1% (by wt), to large amounts, such as up
to 50% (by wt). Preferably the shampoo contains the active agent in
a concentration ranging from 0.1% (by wt) to 5% (by wt), more
preferably from 0.1% (by wt) to 3% (wt). While greater
concentrations of active agent could be present in the shampoo,
they are generally not needed to achieve the desired results.
[0112] Additionally, the shampoo may include from about 0.5% to
about 20% by weight of a surfactant material. Surfactants utilized
in shampoo compositions are well-known in the art and are
disclosed, for example, in U.S. Pat. No. 6,706,258 to Gallagher et
al. and U.S. Pat. No. 7,598,213 to Geary et al.
[0113] iv. Creams, Lotions, Gels, and Polish
[0114] The hair, skin, or nail repair formulation may be in the
form of a cream, lotion, gel, or polish. The cream, lotion, gel, or
polish typically includes the active agent in a suitable carrier.
The active agent may be included in any suitable concentration.
Typical concentrations of the active agent in the cream, lotion,
gel, or polish range from small amounts such as approximately 0.01%
(by wt), preferably at least 0.1% (by wt), to large amounts, such
as up to 50% (by wt). Preferably the cream or lotion contains the
active agent in a concentration ranging from 0.1% (by wt) to 5% (by
wt), more preferably from 0.1% (by wt) to 3% (by wt). While greater
concentrations of active agent could be present in the cream or
lotion, they are generally not needed to achieve the desired
results.
[0115] Additionally, the formulation, depending on use, may include
an oil, a hair conditioning agent, and/or a thickening agent. The
cream, lotion, gel, or polish may also include a fragrance, a plant
extract, and/or a surfactant. The cream, lotion, gel, or polish may
be packaged in a tube, tub, bottle, or other suitable
container.
[0116] v. Liquid Active Agent Formulations
[0117] In some embodiments, a liquid active agent formulation is
provided, which is mixed at the time of use with a second
formulation, such as a coloring or highlighting formulation. 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 concentration of
the active agent is suitable to provide a mixture with the
appropriate final volume and final concentration of active
agent.
[0118] For example, a liquid active agent formulation can contain a
concentration of active agent ranging from about 5% (by wt) to
about 50% (by wt) or greater. In a preferred embodiment, the liquid
active agent formulation contains about 20% (by wt) active
agent.
[0119] For highlighting applications, prior to use, a sufficient
volume of a liquid active agent formulation is mixed with a
sufficient volume of a highlighting formulation to form a
highlighting mixture having the desired concentration of active
agent. Typical concentrations of the active agent in the
highlighting mixture range from small amounts, such as
approximately at least 0.01% (by wt), preferably at least 0.1% (by
wt), to large amounts, such as up to 50% (by wt). Preferably the
highlighting mixture contains the active agent in a concentration
ranging from 0.1% (by wt) to 5% (by wt), more preferably from 0.1%
(by wt) to 3% (wt). While greater concentrations of active agent
could be present in the highlighting mixture, they are generally
not needed to achieve the desired results.
III. Methods of Use
[0120] A. Treatment of Hair with Coloring Agents
[0121] a. Apply the Coloring Formulation to the Hair
[0122] The coloring formulation is generally applied to an
individual's hair following normal hair coloring procedures that
are known to those skilled in the art. Typically, hair color
treatments include two complementary processes: applying a
bleaching formulation to bleach the hair's natural pigment and/or
other artificial pigments present in the hair, and diffusion of dye
precursors into the hair, followed by coupling reactions that
result in the formation of chromophores within the hair shaft,
which are too large to diffuse out of the hair. The bleaching
formulation typically contains a bleaching agent to lighten the
hair and produce free thiol groups. The hair coloring formulation
may be a highlighting formulation, such as formed by mixing bleach
powder and developer. More complex colors may contain several
precursors and many couplers, and may involve multiple
reactions.
[0123] The dye precursors may contain several ingredients, each
with different functions. The first ingredient is usually an
alkalizing agent (usually ammonia and/or an ammonia substitute,
such as monoethanolamine [MEA]). The alkalizing agent serves a
number of roles in the hair colorant process including swelling the
hair fiber to aid in diffusion of the dye precursors. The dye
precursors generally include p-diamines and p-aminophenols.
Precursors are oxidized to active intermediates once they have
penetrated the hair shaft. Intermediates then react with color
couplers to create wash resistant dyes. More specifically, the
intermediates, in the presence of an oxidant, couple with another
oxidation dye intemiediate molecule to form a large fused ring
color compound within the hair shaft. The precursor intermediate
should penetrate the hair shaft prior to the coupling reaction
since the fused ring product is too large to penetrate the hair
shaft. Couplers modify the color produced by the oxidation of
precursor compounds. The primary difference between demi-permanent
and permanent products is the alkalizing agent and the
concentration of peroxide. The cuticle does not swell as greatly
with demi-permanent dyes, making dye penetration less efficient
compared to permanent coloring products.
[0124] Several coloring formulations use a reducing agent, such as
sodium bisulfate, to break disulfide bonds in the hair, allowing
deeper penetration of the hair coloring dyes into the hair.
Specifically, the method includes reducing some of the disulfide
linkages of the cystine in the hair shafts to thiol groups while
breaking hydrogen bonds. The reducing process changes the chemical
and cosmetic characteristics of the hair, which are
undesirable.
[0125] The hair dyeing process may be followed by a shampoo and
conditioning treatment, a neutralizing rinse or an acid balanced
shampoo containing in addition to cationic or amphoteric
surfactants, cation-active emollients and quarternary polymers.
Alternately, the hair dying process may be followed by application
of the active agent formulations described herein, before a shampoo
and/or conditioning treatment.
[0126] b. Apply the Active Agent Formulation to the Hair
[0127] The active agent formulation may be applied simultaneously
with the hair coloring formulation or subsequently to the
application of the hair coloring formulation. For example, the
active agent formulation may be mixed with the hair coloring
treatment and the mixture, containing both the active agent and the
hair coloring treatment, may be applied to the hair.
[0128] Alternatively, subsequent to coloring the hair, the active
agent formulation, or a formulation thereof is applied to the hair.
Although the active agent is typically applied on the same day as
the coloring treatment, it may be applied later such as within 1 to
2 weeks following treatment with the reducing agent. Typically, the
amount of active agent formulation (or a mixture of the active
agent formulation and the hair coloring formulation) applied is
sufficient to saturate the hair. The active agent may be applied to
the hair as a single application, or application of the active
agent may be repeated one or more times. Typically, the amount of
active agent formulation applied in each application 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 100
mL per person depending on their length and volume of hair. In some
embodiments, application of the active agent could be repeated
immediately (e.g. within 10 to 15 seconds) or approximately 1, 5,
7.5, 10, 12.5, 15, 17.5, or 20 minutes after the first
application.
[0129] The active agent can be rinsed and shampooed from the hair
immediately following application, for example within 10, 15, 25,
30, 45, or 60 seconds, or two, three, four, or five minutes after
application. Alternatively, the active agent may be rinsed from the
hair within about 30 minutes following application, preferably
between about 5 minutes and about 20 minutes, more preferably about
10 minutes after application of the active agent to the hair,
depending on hair type.
[0130] If the active agent formulation is combined with the hair
coloring treatment and applied as a mixture to the hair, then the
mixture remains on the hair as long as needed for the hair coloring
treatment. Typically the mixture is applied for approximately 10
minutes. The mixture is removed from the hair in accordance with
standard methods for hair coloring treatments, e.g., rinse and
shampoo, approximately 10 minutes after applying the mixture.
[0131] The active agent formulation is rinsed from the hair after
its application. The hair may be rinsed and subsequently washed
immediately (e.g. within 10 to 15 seconds following application)
after the final application of the active agent. Preferably, the
hair is rinsed and/or washed about 10 minutes or later after the
final application of the active agent, such as about 15 minutes to
about 30 minutes, optionally about 20 minutes after repeated
application of the active agent to the hair.
[0132] The active agents are generally washed from the individual's
hair on the same day as they are applied. In contrast, traditional
perms which use only hydrogen peroxide (and do not involve the
addition of the active agent) are generally not washed for at least
48 hours following application (washing the hair prior to 48 hours
following a traditional permanent treatment may result in
significant loss in the amount of curl in the hair and/or cause
damage to the hair).
[0133] The formulation described herein improves hair quality, such
as appearance (e.g., sheen) and feel, and decreases hair breakage
when the hair is subjected to treatments, such as coloring or
permanent waving.
[0134] In some embodiments, hair breakage decreases by 5, 10, 15,
20, 25, 30, 35, 40, 45, or 50% or higher after treatment with the
active agent compared to untreated hair from the same individual.
Hair breakage is a significant problem encountered during coloring
and other treatments.
[0135] B. Chemical Treatment of Hair with a Reducing Agent
[0136] In one embodiment, prior to treatment with the active agent,
the hair has been subjected to a reducing agent used for waving
(also referred to herein as hair perming or permanent waves),
and/or curling of the hair.
[0137] a. Apply a Reducing Agent to the Hair
[0138] The first step in waving or curling hair is breaking the
cysteine disulfide bonds to form free thiol moieties. The process
for breaking the cysteine disulfide bonds is via application of a
reducing agent. The process for applying the reducing agent
involves following normal perming or hair straightening procedures
that are known to those skilled in the art. For example, to perm
hair, the hair is first washed and set on perm rods of various
sizes. Second, a reducing agent, such as thioglycolate reducing
solution or lotion is applied to the hair. The hair is allowed to
set for a specified period of time, and then the thioglycolate
solution is rinsed from the hair.
[0139] The application of hydrogen peroxide in this process is
optional. In some processes, such as when treating previously
chemically treated hair, hydrogen peroxide is generally not used.
In other processes, such as when perming virgin hair, hydrogen
peroxide may be added. In these embodiments, hydrogen peroxide is
typically added after the reducing agent is rinsed out. Then the
hydrogen peroxide is rinsed from the hair prior to adding the
active agent.
[0140] b. Apply the Active Agent
[0141] Subsequent to the reducing treatment, one or more of the
active agent, or a formulation thereof is applied to the hair.
Although the agent is typically applied on the same day as
treatment with the reducing agent, it may be applied later such as
within 1 to 2 weeks following treatment with the reducing
agent.
[0142] Typically, the amount of active agent formulation applied is
sufficient to saturate the hair. The agent is generally rinsed and
shampooed from the hair after the desired level of hair waving or
curling is achieved. In some embodiments, the active agent is
rinsed from the hair immediately (e.g. within 10, 15, 25, 30, 45,
or 60 seconds following application) following the final
application of the active agent. Alternatively the hair may be
rinsed and washed about within about 30 minutes following
application, preferably between about 5 minutes and about 20
minutes, more preferably about 10 minutes after the final
application of the active agent to the hair, depending on the hair
type. The active agent can be rinsed from the hair within 10, 15,
25, 30, 45, 60 seconds from the hair after application, and still
achieve a desired level of hair waving or curling.
[0143] The active agent may be applied to the hair as a single
application, or application of the agent may be repeated one or
more times. Typically, the amount of active agent formulation
applied in each application is sufficient to saturate the hair. In
some embodiments, the volume of active agent formulation applied to
the hair in each application is about 1 to about 10 mL per perm
rod. In some embodiments, application of the active agent could be
repeated immediately (e.g. within 10 to 15 seconds) or
approximately 1, 5, 7.5, 10, 12.5, 15, 17.5, or 20 minutes after
the first application. In some embodiments, the second application
is about 7 minutes to about 10 minutes after the first
application.
[0144] The active agent is rinsed from the hair after its
application. The hair may be rinsed and washed immediately (e.g.
within 10 to 15 seconds following application) after final
application of the active agent. Alternatively the hair may be
rinsed and washed about 10 minutes or later after the final
application of the active agent, such as about 15 minutes to about
30 minutes, preferably about 20 minutes after repeated application
of the active agent to the hair.
[0145] The active agents are generally washed from the individual's
hair on the same day as they are applied. In contrast, traditional
perms which use only hydrogen peroxide (and do not involve the
addition of the active agent) are generally not washed for at least
48 hours following application (washing the hair prior to 48 hours
following a traditional permanent treatment may result in
significant loss in the amount of curl in the hair and/or cause
damage to the hair).
[0146] The formulations described herein can be applied to hair to
improve hair quality, such as appearance (e.g., sheen) and feel,
and decrease hair breakage when the hair is subjected to subsequent
treatments, such as coloring.
[0147] In some embodiments, hair breakage decreases by 5, 10, 15,
20, 25, 30, 35, 40, 45, or 50% or higher after application of the
active agent compared to untreated hair from the same individual.
Hair breakage is a significant problem encountered during coloring
and other treatments.
[0148] C. Treatment of Skin or Nails with the Active Agent
[0149] In one embodiment, a formulation containing one or more of
the active agents is applied to the skin or nails. Application of
the active agent formulation to skin or nails can help repair
damaged disulfide bonds due to natural wear and tear or natural
aging.
[0150] In some embodiments the active agent formulation is in the
form of a cream or lotion, which is suitable for application to the
skin or nails. In other embodiments, the active agent formulation
is in the form of a gel or polish, which is suitable for
application to the nails. Typically, the amount of active agent
formulation applied is sufficient to treat the damaged keratin in
the skin or nails. The active agent formulation may be applied to
the skin or nails in a single application, or application of the
formulation may be repeated one or more times, as needed, to
achieve the desired effect of repairing keratin damage and/or
strengthening the skin or nails.
IV. Kit
[0151] Kits for treating hair are provided. In one embodiment, the
kit typically contains a first formulation for coloring hair. The
hair coloring formulations typically include a reducing agent
capable of reducing disulfide bonds in hair to produce free thiol
groups. The kit also includes a second formulation containing an
effective amount of the active agent.
[0152] The kit may further include a developer bottle, gloves,
shampoo, conditioner, and/or an odor eliminator. Instructions for
use of the kit are also typically provided.
[0153] Typically the kit contains more than one container (or more
than one compartment in a given container) to ensure that the
lightening agent (e.g., peroxides) or the coloring agent is stored
separately from the active agent.
[0154] A. First Formulation
[0155] The first formulation in the kit can be a coloring
treatment. The first formulation may be formulated as two or more
components which may be mixed together before application to the
hair. For example, the first formulation may be in the form of two
components such as a dye precursor and an oxidant. Typically, the
hair coloring formulation contains a reducing agent capable of
reducing the disulfide bonds in hair and producing reduced free
thiol groups. Suitable reducing agents include, but are not limited
to, thioglycolic acid, thiolactic acid, dihydrolipoate,
thioglycerol, mercaptopropionic acid, sodium bisulfite, ammonium
bisulfide, zinc formaldehyde sulfoxylate, sodium formaldehyde
sulfoxylate, sodium metabisulfite, potassium borohydride, pegylated
thiols and hydroquinone. The amount of the reducing agent in the
first formulation is sufficient to rupture a sufficient number of
disulfide bonds for effective diffusion of the hair coloring
ingredients as would be appreciated by one of skill in the art.
[0156] The components of the first formulation may differ depending
on the hair coloring treatment desired (such as for semi-permanent,
demi-permanent, or permanent hair color), the texture of the hair,
the sensitivity of the user's skin, and such the like. Hair
coloring formulations for different hair coloring treatment, hair
texture, and hair sensitivity are known to those of skill in the
art.
[0157] B. Active Agent Formulation
[0158] The second formulation contains one or more active agents in
an effective amount. Suitable formulations containing the active
agents are discussed above. The second formulation may be in any
suitable 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. The second
formulation will be present in a suitable container, which depends
on the form of the formulation.
[0159] In one embodiment, 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 provided in a vial or other container. A suitable mixing
container for the active agent and the excipient may be
provided.
[0160] In some embodiments, the active agent formulation (or second
formulation) is mixed with the first formulation (or hair coloring
treatment), and the mixture is applied to the hair.
[0161] C. Other Materials in the Kit
[0162] The kit optionally contains shampoos and conditioners.
Suitable shampoos and conditioners include, but are not limited to
LiQWd.RTM. Hydrating Shampoo and LiQWd.RTM. Hydrating
Conditioner.
[0163] The kit may further contain an odor eliminator. The odor
eliminator can be incorporated into the first or second
formulation, or a mixture thereof. Alternately, the odor eliminator
is present in a suitable container for use before or after washing
the second formulation from the hair. Some suitable odor
eliminators are known to those of ordinary skill in the art.
[0164] It is understood that the disclosed method and formulations
are not limited to the particular methodology, protocols, and
reagents described as these may vary. It is also to be understood
that the terminology used herein is for the purpose of describing
particular embodiments only, and is not intended to limit the scope
of the present invention which will be limited only by the appended
claims.
EXAMPLES
Example 1
Color Retention and Texture of Colored Hair Treated with the Active
Agent Formulation
[0165] General
[0166] Three hair samples were obtained from a human subject and
cut in 1/2 inch wide wefts.
[0167] Coloring formulation: The permanent hair coloring
formulation was obtained from a L'Oreal.RTM. permanent hair
coloring service (L'Oreal.RTM. Majirel permanent color #10 with 20
volume peroxide).
[0168] Active agent formulation: Maleic acid, at a concentration of
200 mg in 10 g total solution (water) was used.
[0169] Methods
[0170] The hair samples were washed with a clarifying shampoo then
towel dried. The samples were then colored with the L'Oreal.RTM.
permanent hair color service, which was left on the hair samples
for approximately 35-40 minutes.
[0171] The first color treated hair sample ("control") was
subsequently rinsed and washed with Liqwd.RTM. Hydrating Shampoo
and Conditioner five times before being photographed.
[0172] The active agent formulation was applied to the second and
third color treated hair samples via a spray bottle and massaging
using the fingers. The active agent formulation was left on the
second hair sample for a period of about 1 minute and on the third
sample for a period of about 10 minutes. The hair samples were
subsequently rinsed, and then washed with Liqwd.RTM. Hydrating
Shampoo and Conditioner five times before being examined.
Results:
[0173] The hair samples treated with the active agent formulation
showed better color retention, more shine, and less frizz than the
control. The hair samples treated with the active agent formulation
felt smoother to the touch and combined with the lower frizz and
added sheen gave an overall healthier appearance over the
control.
Example 2
Comparison of Color Retention in Traditionally Permed Hair and Hair
Permed Using the Active Agent Formulations
[0174] Method
[0175] A 1/2 inch wide weft of hair sample, obtained from a human
subject, was washed with clarifying shampoo then towel dried.
Ammonium thioglycolate or dithiothreitol was mechanically pulled
through the hair with a wide and a fine toothcomb several times
then left on the hair for 10 minutes to 1 hour. The hair was then
rinsed for 30 seconds to 1 minute with water, and then towel
dried.
[0176] The active agent formulation, described in Example 1 (Maleic
acid in water), was then applied via a needle nose applicator
drenching the hair and leaving it on for 7.5 minutes. This step was
repeated, for a total of 15 minutes. The hair was then rinsed for
1-2 minutes, shampooed, and then conditioned with various salon
shampoo and conditioner brands, including LiQWd.RTM. Hydrating
Shampoo and Hydrating Conditioner.
[0177] A second sample of hair was straightened, as described
above, but using hydrogen peroxide instead of the active agent
formulation. The hair samples were washed and conditioned
repeatedly.
[0178] Comparison of hair color:
[0179] After both hair samples were washed five times using
LiQWd.RTM. Hydrating Shampoo and LiQWd.RTM. Hydrating Conditioner,
the samples were examined for their color retention.
[0180] Results
[0181] The hair sample treated with the active agent formulation
displayed a color closer in intensity to the hair sample prior to
the first washing, compared to the hair treated with hydrogen
peroxide.
Example 3
Comparison of Hair Treated with Highlighting Formulation Applied
Simultaneously with Active Agent Formulation and Hair Treated with
Highlighting Formulation Alone
[0182] The active agent formulation in Example 1 contained maleic
acid at concentrations of 2.0 g in 10 g total solution (water).
[0183] Two swatches of human hair were tested. A sample was taken
from the same head, 1 inch wide, and split in half. The color was
medium brown and had been previously color treated with an unknown
professional hair color.
[0184] Swatch 1, 1/2 inch wide and 8 inches long, was lightened
with traditional highlighting ingredients mixed with the active
agent formulation. 1 oz of Joico Verocolor Veroxide developer-20
volume was mixed with 1 oz Joico Verolight powder bleach to form
the highlighting formulation. Then 9mL of the active agent
formulation was added to the highlighting formulation to form a
mixture.
[0185] The mixture was applied on the Swatch 1 hair with an
applicator brush as the hair lay on aluminum foil. The foil was
then wrapped around the swatch and allowed to process for 35
minutes. The swatch was rinsed and shampooed one time.
[0186] Swatch 2, the control, 1/2 inch wide and 8 inches long, was
lightened with traditional highlighting ingredients in the absence
of the active agent formulation. 1 oz of Joico Verocolor Veroxide
developer-20 volume was mixed with 1 oz Joico Verolight powder
bleach to form a highlighting formulation with a creamy
consistency.
[0187] The highlighting formulation was applied on the Swatch 2
hair with an applicator brush as the hair lay on aluminum foil. The
foil was then wrapped around the swatch and allowed to process for
35 minutes. The swatch was rinsed and shampooed one time.
[0188] Results
[0189] A noticeable difference in hair quality between Swatch 1 and
Swatch 2 was observed. Swatch 1 hair was softer, less frizzy,
appeared hydrated, with more shine than the control, Swatch 2.
[0190] Both swatches were washed and conditioned 5 more times with
the same noticeable benefits of Swatch 1(treated with the mixture
of highlighting formulation and active agent formulation) compared
to the control, Swatch 2 (treated with highlighting formulation,
alone).
Example 4
Comparison of Hair Treated with Bleaching Formulation Applied
Simultaneously with Active Agent Formulation and Hair Treated with
Bleaching Formulation Alone
[0191] General
[0192] Two hair samples were obtained from a human subject and cut
in 1/2 inch wide wefts.
[0193] Methods
[0194] (1) 0.5 ounces of powder lightener (Clairol Professional,
Basic White) and 0.5 ounces of conditioning cream developer
(Redken, Blonde Icing) were combined to form a bleaching mixture.
3.5 g of 2-(methacryloyloxy)ethan-1-aminium (Z)-3-carboxyacrylate
(12 wt % in water) was added to the bleaching mixture and
thoroughly mixed with a brush.
[0195] (2) The bleaching mixture prepared was brushed onto the
swatches of hair with a brush in order to thoroughly coat the
strands of hair. The mixture coated hair was wrapped in aluminum
paper and allowed to stand under ambient conditions for a period of
two hours.
[0196] (3) After the two hour bleaching period the swatches of hair
were washed with shampoo and the hair was subsequently allowed to
air dry.
[0197] Results
[0198] A noticeable difference in hair quality between Swatch 1 and
Swatch 2 was observed. Swatch 1 hair was demonstrated no
discernible breakage, great feel, and a healthy appearance while
the control (treated with bleaching formulation, alone) showed some
breakage, had a rough feel, and was frayed with an unhealthy
appearance.
Example 5
Comparison of Hair Treated with Bleaching Formulation Applied
Simultaneously with Active Agent Formulation and Hair Treated with
Bleaching Formulation Alone
[0199] General
[0200] Two hair samples were obtained from a human subject and cut
in 1/2 inch wide wefts.
[0201] Methods
[0202] (1) 0.5 ounces of powder lightener (Clairol Professional,
Basic White) and 0.5 ounces of conditioning cream developer
(Redken, Blonde Icing) were combined to form a bleaching mixture.
3.5 g of prop-2-en-1-aminium (Z)-3-carboxyacrylate (10 wt % in
water) was added to the bleaching mixture and thoroughly mixed with
a brush.
[0203] (2) The bleaching mixture prepared was brushed onto the
swatches of hair with a brush in order to thoroughly coat the
strands of hair. The mixture coated hair was wrapped in aluminum
paper and allowed to stand under ambient conditions for a period of
two hours.
[0204] (3) After the two hour bleaching period the swatches of hair
were washed with shampoo and the hair was subsequently allowed to
air dry.
[0205] Results
[0206] A noticeable difference in hair quality between Swatch 1 and
Swatch 2 was observed. Swatch 1 hair was demonstrated no
discernible breakage, great feel, and a healthy appearance while
the control (treated with bleaching formulation, alone) showed some
breakage, had a rough feel, and was frayed with an unhealthy
appearance.
Example 6
Comparison of Traditional Perm Versus Perm Using Maleic Acid
[0207] General
[0208] Hair samples were obtained from a human subject and cut in
1/2 inch wide wefts.
[0209] Reducing agents: Ammonium thioglycolate (ATG) was obtained
from a permanent wave kit manufactured by Zotos. 300 mg of
Dithiothreitol in a 10 g solution was also used as the reducing
agent.
[0210] Active agent formulation: Maleic acid at a concentration of
200 mg in 10 g total solution (water) was used.
[0211] Methods
[0212] Method for Perming Hair Using the Active Agent
[0213] The hair was washed with clarifying shampoo, towel dried,
and then rolled around a perm rod. Ammonium thioglycolate or
dithiothreitol was then applied to the hair and left on the hair
for 10 minutes to 1 hour. The hair was then rinsed for 30 seconds
to 1 minute and then blotted dry with a towel.
[0214] The active agent formulation was applied to the hair, via a
needle nose applicator, drenching the hair. The active agent
formulation was left on the hair for a period of about 7.5 minutes.
The hair was drenched for a second time with the active agent
formulation and left for a second 7 5 minutes, for a total of 15
minutes. The hair was then rinsed with water for about 1-2 minutes
then unrolled from the perm rods. After the hair was removed from
the perm rods, the hair was shampooed and conditioned with various
salon shampoo and conditioner brands, including LiQWd.RTM.
Hydrating Shampoo and Hydrating Conditioner. The washing and drying
steps were repeated 40 times.
[0215] A second portion of hair was permed as described above,
except, hydrogen peroxide was used instead of the active agent
formulation.
[0216] Results
[0217] Both perms (utilizing the active agent formulation or
hydrogen peroxide) showed only slight reduction in the overall curl
after 40 cycles of washing and drying with the same shampoo and
conditioner. However, the appearance and texture of the perm using
the active agent formulation showed more sheen and less frizz
compared to the perm using hydrogen peroxide.
Example 7
Comparison of Hair Breakage Due to Repeated Application of
Traditional Perm and the Active Agent Formulation
[0218] Methods
[0219] Two hair samples were obtained. Both samples were treated
with dithiothreitol or ammonium thioglycolate as described in
Example 4. One of the hair samples was subsequently treated with
the active agent formulation (Maleic acid in water), while the
other was neutralized with hydrogen peroxide. The process was
completed the same day for the hair treated with the active agent
formulation. The process was completed in three days with hydrogen
peroxide (traditional perm).
[0220] The procedure was repeated three times for each hair sample
over a 48 hour time period.
[0221] Results
[0222] Upon visual inspections, the second hair sample treated with
the active agent formulation showed little or no signs of breakage.
However, the first hair sample treated with hydrogen peroxide
showed significant breakage.
Example 8
Comparison of the Extent of Damage to Hair Previously Relaxed with
a Japanese Relaxer
[0223] Methods
[0224] Two samples of hair, the first previously straightened with
a Japanese relaxer (Yuko), and the second previously straightened
with a no lye relaxer (African Pride Miracle Deep Conditioning)
were obtained. The samples were treated as described in Examples 4
and 5 using the active agent formulation (Maleic acid in
water).
[0225] Another hair sample, previously straightened with a no lye
relaxer (African Pride Miracle Deep Conditioning) was obtained. The
sample was treated with a traditional hair straightening perm
(Zotos).
[0226] Results
[0227] The hair samples treated with the active agent formulation
showed no noticeable damage. However, the sample treated with a
traditional perm showed significant breaking, even during
application.
[0228] Unless defined otherwise, all technical and scientific terms
used herein have the same meanings as commonly understood by one of
skill in the art to which the disclosed invention belongs.
Publications cited herein and the materials for which they are
cited are specifically incorporated by reference.
[0229] Those skilled in the art will recognize, or be able to
ascertain using no more than routine experimentation, many
equivalents to the specific embodiments of the invention described
herein. Such equivalents are intended to be encompassed by the
following claims.
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