U.S. patent application number 10/131103 was filed with the patent office on 2002-10-24 for use of tris(hydroxymethyl) aminomethane in cold permanent waving processes.
Invention is credited to Coope, Janet Lynn.
Application Number | 20020155081 10/131103 |
Document ID | / |
Family ID | 24844603 |
Filed Date | 2002-10-24 |
United States Patent
Application |
20020155081 |
Kind Code |
A1 |
Coope, Janet Lynn |
October 24, 2002 |
Use of tris(hydroxymethyl) aminomethane in cold permanent waving
processes
Abstract
There is provided a hair treatment composition for cold
permanent hair waving. The composition is a lotion, preferably in
the form of an aqueous solution, having a pH in the range of from
about 6 to less than 8.5 and a viscosity in the range of from 1 to
about 3000 cps and contains tris(hydroxymethyl)amino methane and a
reducing agent.
Inventors: |
Coope, Janet Lynn; (Norwalk,
CT) |
Correspondence
Address: |
THE PROCTER & GAMBLE COMPANY
INTELLECTUAL PROPERTY DIVISION
WINTON HILL TECHNICAL CENTER - BOX 161
6110 CENTER HILL AVENUE
CINCINNATI
OH
45224
US
|
Family ID: |
24844603 |
Appl. No.: |
10/131103 |
Filed: |
April 23, 2002 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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10131103 |
Apr 23, 2002 |
|
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09708157 |
Nov 7, 2000 |
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Current U.S.
Class: |
424/70.5 ;
424/70.51 |
Current CPC
Class: |
A61K 8/41 20130101; A61Q
5/04 20130101 |
Class at
Publication: |
424/70.5 ;
424/70.51 |
International
Class: |
A61K 007/09 |
Claims
What is claimed is:
1. A cold permanent hair waving composition comprising a lotion
comprising: (a) from about 0.2 wt. % to about 10 wt. %
tris(hydroxymethyl)amino methane; and (b) from about 2 wt. % to
about 30 wt. % of a reducing agent selected from the group
consisting of a sulfite compound and a thiol compound, and (c) an
additive selected from the group consisting of one or more of
swelling agents, diammonium dithiodiglycolate, other alkalizers,
chelating agents, fragrances, dyes, opacifiers, pearlescing agents,
thickeners, wetting and foaming agents, foam stabilizers,
preservatives, softening agents, acids, buffers, solvents,
conditioners and mixtures thereof, and wherein the pH of said
composition is in the range of from about 6.0 to less than 8.5, the
viscosity of the lotion is within the range of from 1 to about 3000
centipoises (cps), and the weight percent are based on the total
weight of the composition.
2. The composition of claim 1, wherein said composition has a pH of
about 6.5 to about 8.0.
3. The composition of claim 2, wherein said composition has a pH of
about 7.5 to about 8.0.
4. The composition of claim 1, wherein said
tris(hydroxymethyl)amino methane is present in an amount from about
0.2 wt. % to about 10 wt. % of the total weight of the
composition.
5. The composition of claim 1, wherein the reducing agent is a
thiol compound present in an amount of from about 5 wt. % to about
15 wt. %, and is selected from the group consisting of glycerol
monothioglycolate, cysteamine, thioglycolic acid and salts of
thioglycolate acid, ammonium thioglycolate, monoethanolamine
thioglycolate, cysteine thioglycolate, cysteine, thiolactic acid
and salts of thiolactic acid, iso-octyl thioglycolate,
N-acetyl-L-cysteine, and mixtures thereof.
6. The composition of claim 3, wherein the reducing agent is a
thiol compound present in an amount of from about 5 wt. % to about
15 wt. %, and is selected from the group consisting of glycerol
monothioglycolate, cysteamine, thioglycolic acid and salts of
thioglycolate acid, ammonium thioglycolate, monoethanolamine
thioglycolate, cysteine thioglycolate, cysteine, thiolactic acid
and salts of thiolactic acid, iso-octyl thioglycolate,
N-acetyl-L-cysteine, and mixtures thereof.
7. The composition of claim 1, wherein the reducing agent is a
thiol compound.
8. The composition of claim 3, wherein the reducing agent is a
thiol compound.
9. The composition of claim 1, wherein the tris(hydroxymethyl)amino
methane is present in an amount of up to about 5 wt. % of the total
weight of the composition.
10. The composition of claim 3, wherein the
tris(hydroxymethyl)amino methane is present in an amount of up to
about 5 wt. % of the total weight of the composition.
11. The composition of claim 1, wherein component (c) is diammonium
thioglycolate.
12. The composition of claim 3, wherein Component (c) is diammonium
thioglycolate.
13. The composition of claim 1, wherein the lotion has a viscosity
within the range of from about 5 to about 2000 cps.
14. The composition of claim 3, wherein the lotion has a viscosity
within the range of from 5 to about 2000 cps.
15. The composition of claim 6, wherein the lotion has a viscosity
within the range of from 5 to about 2000 cps.
16. The composition of claim 3, wherein said
tris(hydroxymethyl)amino methane is present in an amount from about
0.5 wt. % to about 5 wt. % of the total weight of the
composition.
17. The composition of claim 1, wherein said reducing agent has a
pKa of about 6 to about 10.
18. The composition of claim 1, wherein said reducing agent is
present in an amount up to about 20 wt. % of the total weight of
the composition.
19. The composition of claim 1, wherein the composition contains at
least one other alkalizer and said other alkalizer is selected from
the group consisting of: ammonium hydroxide, ammonium carbonate,
ammonium bicarbonate, ammonium chloride, monoethanolamine, and
mixtures thereof.
20. The composition of claim 1, wherein the composition contains a
chelating agent and said chelating agent is selected from the group
consisting of ethylene diamine tetraacetic acid and derivatives
thereof.
Description
RELATED APPLICATION
[0001] This application is a continuation-in-part of my co-pending
application Ser. No. 09/708,157, filed Nov. 7, 2000.
FIELD OF THE INVENTION
[0002] The present invention relates to compositions used in
permanent hair waving processes. More particularly, the present
invention relates to hair treatment compositions that improve the
styling and reshaping of hair using a cold permanent hair waving
process.
BACKGROUND TO THE INVENTION
[0003] Hair is made up of a fibrous protein called keratin. The
shape and stability of the structure of this protein is provided by
three interactions; (1) covalent bonding of cystine cross-linkages;
(2) hydrogen bonding; and (3) salt linkages. The disulfide bonds in
cystine are the strongest of these stabilizing forces.
[0004] To change the natural shape of hair, various treatments have
been devised. One such treatment is permanent waving of hair, which
can be used to either increase or decrease the amount of curl in
hair. Permanent waving of hair may be performed using different
types of treatments. One such treatment is heat waving, which
facilitates the breakage of the disulfide bonds by applying heat in
conjunction with alkali, or a combination of an alkali and a
sulfite reducing agent. However, the heat treatment and chemicals
involved tend to weaken the hair fibers and most of the reactions
are irreversible. EP 129807 describes a heat waving process in
which an amino acid free of a mercapto group is used in conjunction
with an alkali, e.g., tris(hydroxymethyl) amino methane. According
to EP '807 a reducing agent is not used in the disclosed heat
waving process.
[0005] The heat waving method for permanent waving of hair has been
replaced by the popular cold waving process, which restores the
disulfide bonds as herein described. This technique for permanent
waving uses chemical compounds that are capable of breaking the
disulfide bonds and reshaping the hair without the provision of
heat.
[0006] In cold waving, permanent waving is accomplished by a
process that requires (a) chemically cleaving the disulfide bonds
in hair with a reducing agent, (b) optionally rinsing the hair
after cleaving the disulfide bonds, and (c) forming new disulfide
bonds with an oxidizing agent while the hair is under tension in
the new shape that is desired. The cold waving process is gentler
to the hair than the heat waving process because the initial damage
to the hair is largely reversible.
[0007] A lasting permanent wave can be achieved when the disulfide
bonds are arranged in a new configuration. To reshape the hair, it
is believed that 20% to 60% of the disulfide bonds must be broken
and reconfigured in the new shape.
[0008] As stated previously, the reducing agent is used to break
the disulfide bonds. Selection of a reducing agent is largely
dependent upon the pH of the permanent cold waving composition.
Generally, acidic cold permanent wave compositions employ reducing
agents, such as glycerol monothioglycolate or bisulfates, and work
in the lower pH range. On the other hand, cold alkaline permanent
wave compositions utilize alkaline salts of thioglycolic acid. The
reducing agent penetrates and swells the hair shaft thus enabling
the disulfide bonds to be broken. In the cold waving process, a
thiol compound, also known as a mercaptan, is typically used as the
reducing agent.
[0009] Traditionally, ammonia and monoethanolamine have been used
as alkalizers. However, there are drawbacks associated with these
compounds. Ammonia performs well, but has a strong, irritating
odor, which makes it unpleasant. Monoethanolamine has less of an
odor and is commonly used as a substitute for ammonia. However, its
pKa value is 9.50. This means that in a composition having a pH of
7.5, there is only one percent free amine. Thus, monoethanolamine
is not as effective in such a composition. In the practice of cold
waving, low heat is sometimes applied while the reducing agent is
present on the hair. This accelerates the rate of cleaving of the
disulfide bonds. When low heat is used, temperatures are generally
less than about 50.degree. C. during this step, usually below
30.degree. C., but greater than room temperature.
[0010] One drawback to cold waving is the actual permanence of the
change in shape of the hair. The newly configured hair tends to
lose its shape when subject to normal stresses such as brushing,
shampooing, and drying of the hair. These normal wear and tear
stresses weaken the new disulfide bonds, which are constantly
placed under tension.
[0011] Another drawback is the efficiency of the permanent wave.
Efficiency has been characterized in the art as the tightness of
the curl or "true to rod size." Although ammonia is effective at
low pH, it has a strong harsh odor. Monoethanolamine can be used as
a substitute, which has a more acceptable odor, but is less
efficient at low pH.
SUMMARY OF THE INVENTION
[0012] It is an object of the present invention to provide a hair
treatment composition that increases the longevity of a cold
permanent wave.
[0013] It is another object of the present invention to provide
such a hair treatment composition that increases the efficiency of
a cold permanent wave.
[0014] It is also an object of the present invention to provide
such a hair treatment composition that has a pH from about 6 to
less than 8.5.
[0015] It is another object of the present invention to provide a
hair treatment composition that has a high percentage of free amine
in the pH range of from about 6.5 to about 8.0, preferably in the
pH range of from about 7.0 to 8.0, more preferably in the pH range
of 7.5 to 8.0.
[0016] It is still another object of the present invention to
provide such a hair treatment composition that exhibits an
acceptable odor.
[0017] These objects and advantages are achieved by the present
invention, which is a hair treatment composition for cold permanent
hair waving comprising tris(hydroxymethyl)aminomethane and a
reducing agent.
DETAILED DESCRIPTION OF THE INVENTION
[0018] An essential component in the present hair treatment
composition for cold permanent waving is tris(hydroxymethyl)amino
methane ("Tris"), also known as tromethane. Tris serves as an
alkalizer in the present composition. This compound has the
structure shown in formula (I): 1
[0019] Tris is present in an amount from about 0.2 percentage by
weight or weight percent (wt. %) to about 10 wt. % of the total
weight of the present permanent waving composition. Cost
considerations make levels above 10 wt. % undesirable. Preferably,
Tris is present in an amount from about 0.5 wt. % to about 5 wt. %
of the present composition.
[0020] The pKa of Tris is about 8.06. At a pH of about 7.5. Tris
has about 22% free amine, which is significantly greater than
monoethanolamine. In fact, monoethanolamine has only 1% free amine
available at the same pH. This is a critical point because a higher
percentage of free amine (a) increases the diffusion of the amine
into the hair and provides a greater number of reactive sites for
the reaction between the amine and the reducing agent, and (b)
provides a better buffering system to hold the pH at the desired
level.
[0021] The second essential component of the present hair treatment
composition for cold permanent waving is a reducing agent. Any
suitable reducing agent can be used. Such suitable reducing agents
include, but are not limited to thiols (mercaptans), inorganic
sulfides, sulfites, hydrosulfites, phosphines, cyanides, and
combinations thereof. The preferred reducing agent is a thiol or
sulfite compound.
[0022] In general, any suitable thiol compound that can be used in
a permanent waving composition may be employed. Preferred thiols
include, but are not limited to, glycerol monothioglycolate,
cysteamine, thioglycolic acid and salts of thioglycolate acid,
ammonium thioglycolate, monoethanolamine thioglycolate, cysteine
thioglycolate, cysteine, thiolactic acid and its salts, iso-octyl
thioglycolate, N-acetyl-L-cysteine, and combinations thereof.
[0023] The pKa of a particular reducing agent is important because
it greatly affects the rate at which chemical equilibrium of the
reducing reaction is reached. In the present composition, the pKa
of the reducing agent is about 6 to about 10. Preferably, the pKa
is about 6.5 to about 9.5, more preferably about 7 to about 9.
[0024] The reducing agent is present in the present composition in
an amount from about 2 wt. % to about 30 wt. % of the total
composition. Preferably, the reducing agent is about 5 wt. % to
about 20 wt. % of the total weight of the permanent wave
composition. More preferably, there is about 8 wt. % to about 15
wt. % of the reducing agent in the present composition. The actual
amount of the reducing agent that is included is determined by the
waving efficiency desired.
[0025] The present composition may also have other components or
additives. The additives may include, for example, one or more
swelling agents such as urea, diammonium dithiodiglycolate, other
alkalizers, chelating agents, fragrances, dyes, opacifiers,
pearlescing agents, thickeners, wetting and foaming agents, foam
stabilizers, preservatives, softening agents, surfactants, acids,
buffers, solvents, conditioners, and mixtures thereof.
[0026] Suitable materials for these purposes are identified in the
International Cosmetic Ingredient Dictionary and Handbook
(published by The Cosmetic, Toiletry and Fragrance
Association)(Eighth Edition 2000). These materials may be included
in the composition at concentrations effective to provide their
intended function as commonly known in the art.
[0027] By including diammonium dithioglycolate in the permanent
waving composition of the present invention, greater flexibility in
processing time is gained, because it minimizes the possibility of
overprocessing. That is, diammonium dithioglycolate forms an
equilibrium reaction with the thiol reducing agent and with
cysteine in the hair keratin, which proceeds to a certain point and
thus minimizes the possibility of overprocessing the hair.
[0028] Examples of other alkalizers include, but are not limited
to, ammonium hydroxide, ammonium carbonate, ammonium bicarbonate,
ammonium chloride, monoethanolamine, and combinations thereof.
[0029] Chelating agents that bind metal ions in solution may be
included in the present composition. Examples of these chelating
agents are ethylene diamine tetraacetic acid (EDTA) and its
derivatives such as tetrasodium EDTA, and 1-hydroxyethylene-(1,1
diphosphonic acid) sold under the tradename Dequest 2010.RTM. by
Solutia.
[0030] Wetting and foaming agents can also be included in the
composition to improve penetration of the composition into the hair
thereby enhancing thiol diffusion. Examples include, but are not
limited to conditioners such as quaternized fatty amines or
silicones.
[0031] Opacifiers can be included in the composition to provide a
milky appearance. Emulsions of acrylic, vinyl, and styrene polymers
and copolymers are some examples of opacifiers that are
suitable.
[0032] In a preferred embodiment, the hair treatment composition
has an amount from about 0.2 wt. % to about 5 wt. %
tris(hydroxymethyl)amino methane and from about 8 wt. % to about 15
wt. % of a thiol compound. The pH of this preferred composition is
about 6.5 to about 9.5. Preferably, the pH is about 7.0 to less
than 8.5. More preferably, the pH is about 7.5 to about 8.0.
[0033] Optionally, tris(hydroxymethyl)amino methane may be combined
with ammonia, monoethanolamine, or combinations thereof.
[0034] The present invention includes a cold permanent waving
process comprising the steps of (a) applying to hair a permanent
waving composition comprising tris(hydroxymethyl)amino methane and
a reducing agent, (b) allowing the permanent waving composition to
set for a sufficient time, (c) removing the permanent waving
composition from the hair, and (d) applying a restoring agent
selected from the group consisting of oxidizing agents,
crosslinking agents, and mixtures thereof to the hair. Optionally,
the cold waving process may further comprise step (e) shaping the
hair, prior to step (a) or after steps (b) or (c). Preferably,
removing step (c) is performed by rinsing with water. Optionally,
low heat may be applied during step (b), e.g., heated air at a
temperature generally less than 50.degree. C., usually less than
below 30.degree. C.
[0035] The cold permanent waving compositions of this invention are
in the form of a lotion, generally as an aqueous solution, having a
viscosity in the range of from 1 to 3000 centpoises (cps),
preferably within the range of from 5 to about 2000 cps, more
preferably within the range of from 5 to about 500 cps.
[0036] In the cold permanent waving process, the permanent waving
composition is applied as a lotion, after the hair has been
shampooed. The hair may be reconfigured into its new shape prior to
or after applying the permanent waving composition. Next, the
permanent waving composition is allowed to remain on the hair for a
sufficient amount of time to break a sufficient number of disulfide
bonds. This may require 1 minute to 60 minutes of contact time,
typically from about 10 to about 30 minutes. Low heat, e.g., from a
hood style dryer, may be applied if necessary and as described
previously. The permanent wave composition is then removed from the
hair. Generally, this entails thoroughly rinsing the hair with
water. Then, the disulfide bonds are restored. This step is
essential to increase the tensile strength of the hair. Oxidizing
agents typically employed include, but are not limited to, hydrogen
peroxide and bromates. Crosslinking agents that are suitable
include, but are not limited to alkylene dihalides,
dihalocarboxylic acids, dimaleimides, and the like.
[0037] To illustrate the present invention, the following examples
are provided. However, it should be understood that the present
invention is not limited to the examples described.
EXAMPLES
[0038] Three waving lotions were tested using aqueous solutions
having 13.2 wt. % (0.8M) glyceryl monothioglycolate (GMT) and
various concentrations of an amine alkalizer (ammonia,
monoethanolamine, or Tris) as shown in Tables 1 and 2. The pH was
adjusted using a 10 wt. % HCl solution. Tresses were rolled onto
mandrels and evaluated using the permanent wave evaluation
procedure that follows.
[0039] Procedure for Permanent Wave Evaluation
[0040] Each tress evaluation was conducted in quadruplicate to
provide a measurement with a standard deviation of approximately
10%.
[0041] 1. A bundle of 16 inch long medium virgin brown hair was
secured with beeswax by dipping approximately 2 inches of the root
end of the bundled hair into melted wax for 5 seconds. When the wax
is cool to the touch, it is shaped into a square and allowed to
harden.
[0042] 2. Hair is broken into smaller bundles, washed with a 10 wt.
% sodium lauryl sulfate solution and then rinsed.
[0043] 3. Hair is sectioned into tresses of 45 hairs and the waxed
end is re-waxed to further secure the tress. The wax is allowed to
dry, and a piece of tape is wrapped around it to provide a writing
surface. Tresses are trimmed to a length of 12 inches (30 cm) from
the bottom edge of the tape.
[0044] 4. An 8 cm long, 1.25 cm diameter spiral rod with 25 turns
is used. The waxed end of the hair is secured between the gth and
.sub.10th turns using a rubber band. The tress and rod are then
soaked in a 0.1 wt. % solution of Triton X-100 (a mixture of
octylphenoxypolyethoxyethanol and polyethylene glycol) for
approximately 3 minutes.
[0045] 5. A piece of tape, width 2.5 cm, is wrapped sideways around
the bottom edge of the hair, covering the bottom 2.5 cm. A 3.4 g
alligator clip is used to secure the tape. Using a piece of copper
wire as a hook, a 6 oz. weight is hung from the tape at the bottom
of the hair. The hair is rolled around the rod, using the weight to
provide equal tension during rolling. The weight is removed after
rolling, and the bottom tape is secured around the rod with a piece
of Tygon tubing.
[0046] 6. The rod is placed in a wide mouth test tube that contains
10 mL of the appropriate waving lotion, i.e. the composition of
Examples 1, 2, 3 or 4. The solution completely covers the hair. The
test tube is placed in a constant temperature water bath at
37.degree. C. for 20 minutes.
[0047] 7. The rod is removed and rinsed for 3 minutes under running
tap water at approximately 30.degree. C. and a flow rate of
approximately 1 liter/minute. The rod is then placed into a new
test tube with 10 mL of neutralizer (2 wt. % hydrogen peroxide,
0.05 wt. % polyquat-11, and phosphoric acid to pH 3.1). The rod is
removed and rinsed with the 30.degree. C. tap water for 2
minutes.
[0048] 8. The tress is soaked in a bowl of 30.degree. C. tap water
for 5 minutes to allow complete oxidation. The tress is then
carefully unrolled from the rod without tension, starting from the
bottom and keeping the spiral configuration intact. The tape is cut
off the hair using scissors while the hair is still on the rod.
[0049] 9. The tress is hung by the top piece of tape and allowed to
dry while hanging for 1 hour.
[0050] 10. The tress is then hung in a glass containerfilled with a
0.1% Triton X-100 solution (by weight). A glass container
(10.times.11.5.times.4 in) is used in which clear plastic rulers
are glued along the front and back walls. A copper wire is secured
across the top of the container. The rulers should be lined up to
provide a way to accurately measure the hair. A copper wire hook is
placed through the tape at the top of the tress and hung on the
wire. The tress is soaked for 1 hour and then measured using the
rulers in the water.
[0051] Waving Efficiency
[0052] After the procedure, the lengths of the tresses were
measured in a water bath. The shorter the tress, the tighter the
curl and the better the product. The curl is measured from the end
of the wax to the end of the curl. 1 Wave efficiency = L i - L t L
i - L o .times. 100
[0053] where
[0054] L.sub.i=initial length of tress from wax end to tip,
[0055] L.sub.o=length of tress when wrapped on the rod, and
[0056] L.sub.t=length of permed hair from wax end to tip, measured
in the water
[0057] Tables 1 and 2 show that Tris is an effective alkalizer for
a low pH waving lotion.
1TABLE 1 Use of Various Amines (0.75 M) with GMT at pH 7.5 Tress
Length (cm) Percent Waving Amine L.sub.t Efficiency Ammonia 15.5
.+-. 1.2 47.8 Monoethanolamine 16.1 .+-. 0.5 45.4 Tris 15.7 .+-.
0.9 47.0
[0058]
2TABLE 2 Use of Various Amines with GMT at pH 8.0 Molar Tress
Length Percent Concentration (cm) Waving Amine of Amine L.sub.t
Efficiency Ammonia 0.4 14.5 .+-. 1.8 51.8 Ammonia 0.75 14.2 .+-.
0.6 53.0 Monoethanolamine 0.4 15.7 .+-. 1.9 47.0 Monoethanolamine
0.75 17.6 .+-. 1.1 39.4 Tris 0.2 16.2 .+-. 0.9 45.0 Tris 0.4 14.8
.+-. 0.9 50.6 Tris 0.6 16.9 .+-. 0.4 42.2 Tris 0.75 16.5 .+-. 1.4
43.8
[0059] Conclusions
[0060] Tris in combination with a reducing agent produces better
results than monoethanolamine with a reducing agent.
[0061] Use of Tris is beneficial in the pH range of about 6 to
about 10 using any thiol reducing agent. Better results are
obtained at a pH of about 6.5 to about 9.5 and optimal results at a
pH of about 7.5 to about 8.5. This invention is useful for
preparing formulations without ammonia or in combination with
ammonia, monoethanolamine, or mixtures thereof. Examples of thiols
that are useful with this invention are glycerol monothioglycolate,
cysteamine, thioglycolic acid, cysteine, dithiothreitol,
dithioerythritol and thiolactic acid.
[0062] Having thus described the present invention with particular
reference to preferred embodiments thereof, it will be apparent
that various changes and modifications may be made therein without
departing from the spirit and scope of the present invention as
defined in the appended claims.
* * * * *