CA1315204C - Hair waving compositions - Google Patents

Hair waving compositions

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Publication number
CA1315204C
CA1315204C CA000549133A CA549133A CA1315204C CA 1315204 C CA1315204 C CA 1315204C CA 000549133 A CA000549133 A CA 000549133A CA 549133 A CA549133 A CA 549133A CA 1315204 C CA1315204 C CA 1315204C
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Prior art keywords
composition
hair
urea
ammonium
thioglycolate
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Expired - Fee Related
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CA000549133A
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French (fr)
Inventor
Diane Grob Schmidt
Robert Lee Wells
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Schwarzkopf and DEP Corp
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Schwarzkopf and DEP Corp
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Abstract

ABSTRACT OF THE DISCLOSURE

HAIR WAVING COMPOSITIONS

This invention relates to permanent waving compositions comprising from about 5.5% to about 11.5% ammonium thioglycolate, from about 1% to about 3% urea, buffers and from about 65% to about 90% water; wherein the pH of the composition is from about 8.5 to about 9Ø

Description

3 ~s ~

-` 1 3 1 520~

~IAIR WAVINC COMPOSITIONS
Diane Grob Schmidt Robert Lee Wells TECHNICAL FIELD
5This invention relates to permanent wave compositions. In particular, the invention relates to an improved reducing composi-tion for use in a permanent waving operation wherein good curl retention is provided along with lowered skin irritation.
BACKGROUND OF THE I NVENTION
Hair waving is accomplished by altering disulfide crosslinks of the hair while it is maintained in the desired configuration, e.g., a curled position. The softening of the hair is a required step in waving of hair. In the modern "cold wave", this softening and subsequent rearrangement of the hair is achieved 15 by use of a reducing composition such as a mercaptanO The mercaptan breaks the disulfide linkages presen~ in the keratin of the hair. This reducing step may be done before hair has been rolled onto perm rods, after such rolling or both. After sufficient time has elapsed, the hair must be rehardened in the 20 new configuration. In the cold wave, this is achieved by use of a neutralizer in an oxidation step which reforms the disulfide bonds broken in the reducing step.
Most modern cold wave compositions have reducing composi-tions based on thioglycolic acid. Such compositions were first 25 introduced in the 1940's. U.S. 2,S77,710, McDonough, issued December 4, 1951; U.S. 2,577,711, McDonough, issued December 4, 1951; U.S. 2,736,323, hlcDonough, issued February 28, 1956; U.S. 2,889,833, McDonough, issued June 9, _ _ 1959, U . S . 2, 631, 965, Schnel I, issued March 17, 1953; and 30 U.S. 2,653,121, Schnell, issued September 22, 1953, disclose various thioglycolate reducing agents and methods for their use. Early compositions required high pH's; i.e., up to 11 in order to provide effective results. Ho~ever, such high pH's also frequently resulted in 35 substantial hair damage. Specific thioglycolate salts have been disclosed as particularly effective or beneficial such as - 131520~

monoethanolamine thioglycolate in U.S. 3,157,758, Zviak et al, issued November 12, 1964, and in French Patent 784,404, Coustolle (1946) . These compositions are disclosed to be useable at lower pHs, thus reducing hair and skin damage.
The effectiveness of thioglycolate-containing waving composi-tions can be modified by adjustment of various factors including pH, alkalinity, concentration of thioglycolates, addition of ac-celerators and change in amount of time that the composition remains on hair, Among the accelerators disclosed for use in thioglycolate waving compositions are urea and alkyl ureas . U . S .
2,717,228, Brown, issued September 6, 1955, states tllat urea accelerates the swelling o~ hair, thus permitting a decrease in the level of thioglycolate necessary to achieve curl retention, Brown employs levels of urea consider-ably higher than the levels of thioglycolate empioyed (e.g., 5%
ammonium thioglycolate, 1296 urea). U.S. 3,399,682, Isaji, issued September 3, 1968, discloses hair dye compositions comprising thioglycolate and urea in varying ranges. U.~i. 3,396,736, Stansky, issued August 13, 1968, likewise discloses hair dye and wave/dye compositions employing urea as an accelerator . U . S .
3,880,174, Wajaroff, issued April 29, 1975 discloses 2-step wave compositions with various accelerators.
Even with use of urea and other accelerators, thioglycolate waving compositions have had problems achieving good curl reten-tion without also increasing skin irritation and hair damage.
Factors affecting skin and hair damage include alkalinity, pH, thioglycolate and/or urea levels. High levels of urea can also result in overprocessing of hair caused by excessive swelling.
Applicant has now surprisingly discovered that a waving composition with specific ranges of ammonium thioglycolate, urea, and a specific alkalinity and pH range provides good curl retention along with low skin irritancy.
It is an object of this invention to provide a permanent waving composition for use in the home or salon which provides good curl retention.
It is a further object of this invention to provide a perma-nent waving composition which has low skin irritancy.

- ~7 " 1315~0~

it is a further object of this invention to provide a perma-nent waving composition comprising urea.
It is a further object of the invention to provide composi-tions which provide the proper amount of waving for the con-sumer's hair type.
These and other objects will become apparent from the following description of the invention.
As used herein, the following definitions are applicable unless otherwise noted.
Permanent or permanent wave or wavin~3 composition or reducing lotion are all synonymous terms as used herein and refer to a reducing composition whiclh is applied to hair in order to produce a permanently altered configuration, generally waves or curls.
Neutralizer i5 an oxidizing composition applied to the hair to reharden it after the reducing lotion, supra, is removed.
All percentages and ratios herein are by weight unless otherwise noted.
SUMMARY OF THE INVENTION
Permanent waving compositions of the invention comprise from about 5.5% to about 11.5% ammonium thioglycolate, from about 196 to about 3~ urea, a buffer concentration to provide a composition normality of from about 0.05N to about 2N and water.
The pH of the compositions range from about 8.5 to about 9Ø
Detailed Description The following describes the essential as well as the optional ing redients .
Ammonium Thio~lycolate Appiicant has surprisingly found that when used in composi-tions within the invention, that ammonium thioglycolate gives a faster and better curl and is less damaging to the hair than other thioglycolate salts.
Compositions of the invention comprise from about 5 . 5% to about 11.5% ammonium thioglycolate; different compositions can be 35 made to correspond to the various types of hair. The preferred method of formulation is to vary the amount of ammonium thiogly-colate present in the composition. Hard to-wave, normal and easy-to-wave versions may be created by adjusting such level.
For the hard-to-wave version, about 9% to about 11.5~ ammonium thioglycolate is useful; for normai hair fro~ about 7~ to about 9~
ammonium thioglycolate is useful; and for easy-to-perm hair, from about 5.5~ to about 7.5% ammonium thioglycolate is useful. The optimum ranges of urea and of the pH of the compositions are not varied with the version.
U rea Compositions of the invention contain from about 1~ to about 3~ of urea or a iower monoalkyl urea, such as methyl urea or ethyl urea.
Urea serves as a swelling agent for hair in order to facilitate breakdown of the disulfide linkages in the keratin fibers of the hair. This allows a lower percentage of ammonium thioglycolate to be used. However, when used in higher amounts urea can cause overprocessing and damage to hair as well as skin irritation and burning .
Applicants have surprisingly found that use of from about 1~
to about 3% of urea along with the cited levels of thioglycolate and specific pHs result in good curl ratention without an increase in skin irritation or hair damage.
Water Water is the last of the essential ingredients. Water is present in amounts from about 50% to about 90~. Where the composition is in the form of a lotion, water preferably comprises from about 70~ to about 90~.
Buffers The pH of the compositions of the invention is from about 8.5 to about 9.0, preferably from about 8.6 to about 8.9.
Applicant has discovered that when compositions of the invention are used at the preferred pH, an effective curl is obtained without skin irritation. Any alkali safe for use on the hair or skin at the necessary levels may be used to regulate pH.
Preferred agents for regulating the pH of the invention inclucle 1 31 520~

ammonium hydroxide, sodium hydroxide, ammonium bicarbonate, alkanolamines and mixtures thereof. Ammonium hydroxide, ammonium bicarbonate and mixtures thereof are preferred.
Compositions within the invention comprise buffers to provide final composition normality of from about 0.05N to about 2N, preferably from about 0 . 5N to about 1 . 6N .
Optional Ingredients In addition to the essentiai ingredients any of the conven-tional nonessential ingredients may be used in compositions of the invention such as emulsifiers, emollients, wetting agents such as anionic or nonionic surfactants, conditioners, opacifiers, thick-eners, preservatives, coloring agents, perfumes, and the like.
These optional materials when present are generally used singly at a level of from about . 01~ to about 10%, preferably from about 0.5~ to about 5~ of the composition.
One preferred optional ingredient is an emulsifier. Useful emulsifiers include soaps and anionic and nonionic synthetic surfactants. Examples of such emulsifiers include polyethylene oxide condensates of alkyl phenols, non-polar nonionics such as laureth-2 laureth-4 and ceteath-2, alkyl sulfates, alkyl ether sulfates, and succinates.
Another preferred optional ingredient is a conditioner.
Preferred conditioners include cationic polymers such as polyquaternium-6 and polyquaternium-16.
Where the product is a foam or mousse or aerosol a propel-lant phase may also be ~present. The propellant gas can be any liquifiable gas conventionally used for aerosol containers.
Preferably the propellant or mixture of propellants, has a density of less than 1 so that pure propellant is not emitted from the container. Examples of suitable propellants include trichloro-fluoromethane, dichlorofluoromethane, dichlorodifluromethane, monochlorodifluoromethane, propane, trichlorotrifluromethane, dimethylether, n-butane, isobutane and mixtures thereof. The hydrocarbons are preferred for their densities. The amount of propellant is from about 1~ to about 20~ of the composition.

1 31 5~0~

MET~IODS OF MANUFACTURE
The compositions of the invention may be made by any conventional means in the art. See, e.g., ~lollenberg, I. R., Formulation of Cold Wave Preparations, Proc. Sci . Sec. TGA, 13: 9 (1950).
METHOD OF USE
Compositions of the invention may be used as either salon permanents or home permanents. The compositions are especially suited for home permanent use, and may be supplied in a "kit"
10 form with other necessary items such as neutralizing lotion, after perm shampoos and conditioners, end wraps, perm rods, gloves and the like.
Compositions of the invention may be applied to the hair either prior to or subsequent to placing the hair in the desired 15 configuration (i.e., by rolling on permanent rods. ) The compositions are left on the hair for up to about 35 minutes, depending on the hair type and amount of curl desired. The compositions are then rinsed from the hair.
Application of a neutralizing composition is essential in order 2Q to reharden the hair and stop the reducing process. The neu-tralizing lotion is preferably in solution form and may be made from suitable oxidizing agents such as peroxides, alkali metal bromates, perborates, percarbonates, perpyrophosphates, and perborosilicates. Hydrogen peroxide is especially preferred. The 25 hair is first rinsed to remove the majority of the thioglycolate solution. The neutralizer is then applied and remains on the hair for a period of time, preferably about 5 minutes, and the hair is then rinsed prior to drying or styling.
The active ingredients may be applied to hair in any suitable 30 form. They may be lotions, creams, gels, foams, mousses, aerosols, etc.
The following Examples are meant to be illustrations and not as limitations on the invention as many variations thereof are possible without departing from its spirit and scope.

EXAM PLES
EXAMPLE I
_ _ The following lotion compositions representative of the present invention are made according to conventional processes.
Easy to Hard to Perm Normal Perm Ammonium thioglycolate8.469611.84~ 14.39 Ammonium hydroxide (29~) 1.02 1.43 1.73 Urea 2.00 2.00 2.00 Polyoxyethylene lauryiether 3.00 3.00 3.00 Luviquat 9051~ 1.25 1.25 1.25 Color 0.07 0.07 0.07 Perfume 1.50 1.50 1.50 DRO Water 82.70 78.91 76.06 100.00 100.00100.00 1 Luviquat 905- is a quaternary cationic conditioning agent sold by BASF, Inc. PH of the compositions range from about 8.6 to about 8.9.
EXAMPLE l l The following is another lotion composition representative of the invention.
Ingredients Level in Total Formula Ammonium thioglycolate ~71%) 12.54 Ammonium hydroxide (29%~* 4.00 Ammonium bicarbonate 6.50 U rea 2.00 Conditioning ingredients 2.50 Perfume 1.50 Lmulsifier premix 3.00 Opacifier 0 05 Color 0 07 DRO water qs 100 100.00 * may be adjusted slightly so that the finished composition above has a pH of about a. 9.

1 3 1 5~04 EXAMPLE I H
The following are mousse or foam compositions representative of the present invention:
Ea sy to Aqueous Phase Perm Normal Ammonium thioglycolate (71 %) 8 . 44~ 11 . 84 Ammonium hydroxide (29%) 1.05 1.48 Urea 2.00 2.00 Polyoxyethylene lauryl ether1.16 1.16 Luviquat FC 905~1 1.25 1,25 Sodium silicate 0.03 0.03 Water 75.51 71.68 Propellant phase Perfume 1 . 66 1 . 66 Isopropyl myristate 5.15 5.15 Hydrofluorocarbon 3 . 75 3. 75 1 00% 1 00~

1 Luviquat 905 is a quaternary cationic conditioning agent sold by 20 BASF, Inc.
Water is placed in the mixing tank. The ammonium thiogly colate, ammonium hydroxide and ammonium bicarbonate are added at room temperature, mixing well after each is added. The urea is then mixed and followed by the conditioning ingredients and 25 emulsifiers. The perfume, isopropyl myristate and propellant are added immediately before packing. The finished compositions have pH's of from about 8.6 to about 8.9.
EXAMPLE IV
The following is another representative foam composition of the invention.
Ingredients Level in Total Formula Aqueous Phase:
Ammonium thioglycolate (71%) 12.54 Ammonium hydroxide ~29~)4.00 Ammonium bicarbonate 6 . 50 ,~

U rea 2 . 00 Conditioning ingredients2 . 50 Emulsifier 3 .
DRO water 59.15%
Propellant Phase:
Perfume 1 . 60 I sopropyl myristate 4 . 96 Propellant 3 . 75 100.00 t 0 EXAMPLE V
Hair Dama~e Test The methylene blue test is designed to measure the amount of methylene blue dye absorbed by the hair after a given treat-ment. The more damaged the hair is, e.g., by chemical treat-l S ments, the more subs~antive the dye is to it. Damage can ~
therefore, be determined by measuring the amount of dye which the hair absorbs. The amount of residual dye in the solution is measured after the hairs have been soaked and have been removed. The dye concentration is then easily measured on the spectrophotometer.
A stock 1~ methylene blue solution is prepared by weighing one gram of methylene blue powder on a 4 place balance and one gram of Tween 80~, a surfactant (to aid wetting of the hair).
One thousand ml of water, measured in a graduated cylinder, is added to the dye/surfactant. The stock solution is then diluted ~or use as follows: sodium tetraborate decahydrate - 3.81 grams, methyl blue .1~ stock solution - 10.0 grams, distilled water q.s.
to 1000 ml. A standard curve for the dye solution is obtained by preparing several different concentration levels, obtaining a scan reading between 6001l 70OIJ for each and plotting peak absorb-ance versus concentration (mgll ) . The slope was then used in calculating the concentration of the dye solution after soaking the hairs .
The hair damage data appear in the table below under the heading of hair damage. Larger numbers indicate more absorption of dye, and thus more damaged hair. Formula 1 is representative of this invention.

~r Swe!ling Test Virgin blond hair is soaked for 24 hours in an iodine solu-tion then removed and rinsed. The dry diameter is measured under a microscope at 400x magnification. The hair is then 5 treated with waving lotion, and a final diameter determina~ion is made under the microscope. Again, formula 1 is within the invention. Each figure represents the average of three repli-cations .
Hair Damage Swelling (at 100~ penetration) Formula 1 (ammonium thioglycolate - 7.5%
urea 2~, pH 8.5) 2.11 24.5 Formu la 2 (ammonium thioglycolate - 7.596 urea 4~, pH 8.5) 2 . 38 54 . 4%

Formula 3 lammonium thioglycolate - 7 . 5%
urea 2~, pH 9.3) 2.76 31.7%

Formula 4 (ammonium thioglycolate - 7 .5%
urea 4~, pH 9.3~ 3.02 52.0~

As can be seen from the data, the composition within the scope of the invention (formula 1 ) provided the least amount of hair damage, and swelling.

WHAT IS CLAIMED IS:

Claims (21)

1. A permanent waving composition comprising:
(a) from about 5.5% to about 11.5% ammonium thioglycolate:
(b) from about 1% to about 3% urea or a lower mono-alkyl urea;
(c) buffers; and (d) from about 65% to about 90% water, wherein the composition has a pH from about 8.5 to about 9.0, and a normality of from about 0.05 N to about 2 N.
2. A composition according to Claim 1 wherein pH is from about 8.6 to about 8.9.
3. A composition according to Claim 1 comprising from about 1.75% to 2.5% urea.
4. A composition according to Claim 2 comprising from about 1% to about 8% buffers.
5. A composition according to Claim 4 for hard to perm hair wherein the ammonium thioglycolate is from about 9% to about 11.5% of the composition.
6. A composition according to Claim 4 for normal hair comprising from about 7% to about 9% ammonium thioglycolate.
7. A composition according to Claim 4 for easy to perm hair comprising from about 5.5% to about 7.5% ammonium thioglycolate.
8. A composition according to Claim 1 further comprising an emulsifier.
9. A composition according to Claim 1 further comprising a conditioning agent.
10. A composition according to Claim 9 wherein the conditioning agent is a quaternary cationic conditioning agent.
11. A permanent waving composition comprising:
(a) from about 5.5% to about 11.5% ammonium thioglycolate (b) from about 1.75% to about 2.5% urea;
(c) from about 0.5% to about 2% ammonium hydroxide;
(d) from about 1% to about 7% ammonium bicarbonate;
(e) from about 2% to about 4% of a nonioic emulsifier;
(f) from about 0.5% to about 2% of a conditioning agent: and (g) from about 65% to about 90% water, wherein the pH is from about 8.6 to about 8.9.
12. A composition according to Claim 11 in the form of a lotion.
13. A composition according to Claim 11 in the form of a mousse or foam.
14. A composition according to Claim 13 wherein an aqueous phase comprises:
(a) from about 6% to about 11.5% ammonium thioglycolate;
(b) from about 0.5% to about 2% ammonium hydroxide;
(c) from about 1.75% to about 2.5% urea;
(d) from about 4% to about 7% ammonium bicarbonate;
(e) from about 1% to about 2% polyoxyethylene lauryl ether;
(f) from about 0.5% to about 2% of a quaternary cationic conditioning agent; and, (g) from about 65% to about 80% water, wherein the pH is from about 8.6 to about 8.9, and wherein a propellant phase comprises a hydrofluorocarbon.
15. A method of permanently deforming the hair where a composi-tion according to Claim 1 is applied to the hair, left on the hair for a period of time, the hair rinsed and then neutral-ized.
16. A method according to Claim 15 wherein the composition is according to Claim 11.
17. A method according to Claim 15 wherein the composition is according to Claim 14.
18. A method according to Claim 15 wherein the composition placed on the hair is selected for effectiveness on a specific type of hair.
19. A method according to Claim 18 wherein the composition selected is according to Claim 5.
20. A method according to Claim 18 wherein the composition selected is according to Claim 6.
21. A method according to Claim 18 wherein the composition selected is according to Claim 7.

DPN/lao/pw/A16-100
CA000549133A 1986-10-14 1987-10-13 Hair waving compositions Expired - Fee Related CA1315204C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US91843386A 1986-10-14 1986-10-14
US918,433 1992-07-22

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CA1315204C true CA1315204C (en) 1993-03-30

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8906352B2 (en) 2006-05-24 2014-12-09 L'oreal Method for straightening human hair fibers using heating means and an α-hydroxy acid derivative
EP2826461A1 (en) 2004-11-26 2015-01-21 L'Oréal Method for straightening keratin fibres using a heating means and a denaturing agent
US11044978B2 (en) 2006-05-24 2021-06-29 L'oreal Method for straightening keratinous fibers using heating means and an aromatic compound

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2826461A1 (en) 2004-11-26 2015-01-21 L'Oréal Method for straightening keratin fibres using a heating means and a denaturing agent
US8906352B2 (en) 2006-05-24 2014-12-09 L'oreal Method for straightening human hair fibers using heating means and an α-hydroxy acid derivative
EP3141284A1 (en) 2006-05-24 2017-03-15 L'Oréal Method of straightening keratinous fibers using heating means and an acid derivative
US9743736B2 (en) 2006-05-24 2017-08-29 L'oreal Method for straightening human hair fibers using heating means and malic acid
US10561216B2 (en) 2006-05-24 2020-02-18 L'oreal Method for straightening human hair fibers using heating means and an a-keto acid derivative
US11013306B2 (en) 2006-05-24 2021-05-25 L'oreal Method for straightening keratinous fibers using heating means and malic acid
US11044978B2 (en) 2006-05-24 2021-06-29 L'oreal Method for straightening keratinous fibers using heating means and an aromatic compound

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