CA2039121A1

CA2039121A1 - Permanent wave composition and method

Info

Publication number: CA2039121A1
Application number: CA 2039121
Authority: CA
Inventors: Stanley J. Kolc; Richard A. Abbott; Arun Nandagiri
Original assignee: Helene Curtis Inc
Current assignee: Helene Curtis Inc
Priority date: 1991-03-15
Filing date: 1991-03-26
Publication date: 1992-09-16
Also published as: AU635625B2; JPH04295413A; AU7406891A; NZ237592A; JPH0714859B2

Abstract

PATENT APPLICATION

ABSTRACT OF THE DISCLOSURE
A mild, alkaline permanent wave reducing composition and method of permanently waving or reshaping human hair that provides a strong, long lasting curl like an alkaline permanent wave composition but leaves the hair soft like an acid permanent wave composition and leaves essentially no post-perm odor.
The composition contains about 2.0% to about 6.5% by weight of a cysteine reducing agent compound selected from the group consisting of cysteine, a cysteine salt, and mixtures thereof; about 4.5% to about 8.0% of a thioglycolate; and sufficient additional alkali, if necessary, to bring the pH of the composition within the range of about 7.5 to about 9.5.

Description

~3~2i PATENT APPLICATION

TIT~E

PERMANENT WAVE COMPO8ITION AND ~ET~OD

FIELD OF TBE Ihv~ION
The present invention ia directed to a cysteine-based composition and method for relatively permanently re~haping or curling human hair into a la~ting curl pattern. More particularly, the present invention is directed to a compoaition and method capable of forming a "permanent" wave in human hai~
including a cysteine reducing agent within a relatively narrow range of about 2.0% to about 6.5% by weight: and a thioglycolate r~ducing agent within a relatively narrow range of about 4.5~ to about 8.0% by weight of the cQmpositlon to provide a perman~nt wave compo~ition th~t has the distinct advantage of no post-perm odor, without aacrificing performance, such as curl formation, curl spring, manageability, ease of combing, body, luster, soft ~eel, and the like. The compo3ition can be applied to the hair, with or wlthout heating, as a water wrap or a lotion wrap to produce a strong curl while leaving the hair fe~ling ao~t like an acid permanent wave compo~ition without odor.
3~

2 ~

PATENT APPLICATION

BACRG~ND OF TI~E INV'ENTION AND PRIOR ART

In general, permanent waving of human hair is achieved by chemically breaking the sulfur to sulfur or disulfide cystine bond~ occurring naturally in human hair and then reforming the cy~tine bonds while the hair is wrapped or curled on rods. The sulfur to sulfur cystine bonds in human hair maintain the hair in a naturally straight or curly configuration and, in order to permanently reshape the hair into a lasting, different configuration, a significant percentage of the sulfur to sulfur bonds must be broken and then reestablished after the hair is reconfigured in a des~red position, such as wrapped around a suitable mandrel or roller. In general, the sulfur to ~ulfur cystine bonds are broken with a composition containing a reducing agent and after the hair is wound into a curl formation around a rod or roller, the sulfur to sulfur cystine bonds are relinked or reestablished while the hair is in the curl formation by contacting the hair in the ne~ formation with an oxidizing agent, such as hydrogen peroxlde or a water-soluble bromate.

There are three general types of permanent wave composition~ or lotions u~ed to break the cystine bonds in human hair, generally known as acid wave composition~; alkaline wave compositions; and neutral wave compo~iti~ns. Of these three, the acid and alkaline wave compositions are most significant commercially. Permanent wave compositions containing an alkaline salt of thioglycolic acid (TG), such as ammonium thioslycolate a3 the reducing agent, are 2~3~:~2 i PATENT APPLICATION

_ 3 _ generally known as alkaline wave composition~ and generally have a pH in the range of about 7.5 to about 9.4. The alkaline wave compositions are known as the conventional cold wave compositions, since free alkali penetrates and swells the hair ~haft allowing the S reducing agent to enter the hair shaft and break the sulfur to sulfur bonds without added heat. The permanent wave compositions containing glycerol monothioglycolate ( GMTG ) are known as acid wave composition~ even though the p~ of thesQ compositions can be as high as about 9Ø Generally speaking, the acid permanent wave compositions have a lower p~ than the alkaline permanent wave compositions and, therefore, require heat and/or longer proces~ing time to achieve sufficient reaction of the reducing agent. The alkaline permanent wave compositions produce a stronger, longer la~ting curl while the acid permanent wave compositions provide a softer feel but a shorter curl duration. The permanent wave compo~ition~ containing an alkaline salt of thioglycolis acid and/or glycerol monothioglycolate leave the hair with a very noticeable sulfur odor.

The reducing action of mercaptans on keratin i9 due mostly to the dissociated form of the thiol groups, the thiolate anion. Acid permanent wave~
sufficiently curl hair at a lower p~ compated to alkaline permanents because the waving agents in these permanent~ have low pKa value~ and thu~ exist predo~inantly in dissociated (thiolate) form at a pH
near neutral, or slightly acidic p~. ~ence, the p~a value shows that some mercaptan~ are efficient at high pH while others with a low pKa value and high ionization 2~3~ .2~.

PATENT APPLICATION

constant are e~ficient at lower p~ values. For example, it is well known that the alkaline salt~ of thioglycolic acid, e.g., the ammonium ~alt of thioglycolic acid (pKa=10.4) has acceptable waving efficiency only i~ the p~ of solution exceeds 9.0, see Zviak, Charles, The Science of ~air Care, Permanent Waving and ~air Straightening, p. 191, 1986; whi~e amides such a3 thiogly~olamide IpKa=8.4), and ester~ such as glycerol thioglycolate ~pKa=7.8) give acceptable waving efficiency at neutral and even slightly acid p~.
The cysteine and thioglycolate-based reducinq agent-containing composition and method of the present invention are unexpectedly effective in the p~ range of about 7.5 to about 9.5 and particularly in the p~ range of about 9.0 to about 9.5. Compo3itions having a p~ in the lower end o~ the p~ range (e.q., about 7.5 to about 8.5) are mo~t effective for bleached hair, while composition~ having a pH in th~ higher end (e.g., about 9.0 to about 9.5) are mo~t effective for normal and curl-resistant hair. A number of compositions can be providad that are par~icularly suited for permanent wavinq hair in different condition~.

For example, a composition for permanently waving normal and tinted hair (hair with little damage) contains about 5.0% to about 7.0% thioglycolate and about 4.0% to about 6.0% cy~teine; a composition for bleached hair contains about 3.5~ to about 5.5%
thioglycolate and about 2.0~ to about 4.0% cysteine: and 2~3~ ~ 2 ~

PATENT APPLICATION

_ 5 _ ;

a composition for curl-resistant hair contain about 5.53 to about 7.5% thioglycolate and about 5.0S to about 6 . 5~ cysteine.

Different reducing agents are ef~ective to break the cystine bonds that cross link human hair protein at diferent p~'9. Generally speaklng, the acid permanent wave compositions having a lower pH include reducing agents such as bisulfites, e.g., ammonium bisulfite, or glycerol monoth'oglycolate, capable of breaking the sulfur to sulfur cystine bonds within lower p~ ranges, whereas the alkaline permanent wave compositions, having pH's in the range of about 7.5 to 9.5, require an alkaline salt of thioglycolic acid or an alkaline salt of a dithioglycolic acid - 90 that the alkali can penetrate and swell the hair shaft for easier penetration of the reducing agent in order to break the sulfur to sulfur cy3tine bonds.

Perhap~ the most difficult factor for the applier of the per~anent wave lotion to asses3 in determinlng how long to apply the reducing agent to the hair is the condition of the hair at the time of the permanent wave. It is well documented in the literature and prior art that the hair can be damaged by abuse of chemicals, e.g., by shampooing, permanent waving, ~inting, fros~ing, bleaching, and particularly any hair treatment involving the use of hydrogen peroxide:
mechanical ~reatment, e.g., thermal appliance3; and environmental conditions, e.g., climate and pollution.
It i8 well known that damaged hair, dependin~ upon the stage and degree of damage oF the hair, has 203~

PATENT APPLICATION

significantly different chemical activity to reducing agents than normal or undamaged hair. If too many of the sulfur to ~ulfur bonds in the hair are broken by the reducing agent, the hair will be seriously weakened and may dlsintegrate.

It is theorized that somewhere in the range of about 20% to about 60~ of the natural ~ulfur to sulfur cystine bonds in the hair shafts should be broken in order to give the hair the capability of being reshaped to any desired shape, such as curled around a rod or roller, and capable of retaining this shape. If too few of the sulfur to sulfur bonds are broken, the natural or normal configuration of the hair will predominate, causing the hair to retain its previous shape. This is because the predominant prior or natural bonds in the hair dictate that the hair will remain in the old configuration or shape. ~ydrogen bonds are physically broken when wet hair is stretched and wrapped around a roller. When the hair i9 dried, the hydrogen bonds are reformed in 3 curled position or shape. While the hydrogen bonds aid to maintain the hair in the new coniguratlon, the sulfur to sulfur cystine bonds are much stronger and, to a much greater extent than the hydrogen bonds, control the efficacy of the permanent wave.

In order to successfully provide a sati~factory permanent wave in the hair, the sulfur to sulfur cystine bonds reformed in the hair in the new or curled configuration, when the hair is later oxidized with the neutralizing agent, should be as ~trong as the 203~ 9 ~

PATENT APPLICATION

prlor or natural cystine hair bonds. It is desired, therefore, when permanent waving, that enough new bond~
in a new hair configuration are ~ormed during permanent waving to equal the number of old bond~ remaining that tend to form the hair in it9 prior or natural configuration, whether it be straight or naturally curled.

Generally! the reducing agent lotion is applied to the hair by first shampooing the hair and then applying the reducing agent lotion to the hair, either before or after the hair is wrapped around 3uitable rollers. When the reducing agent lotion is applied to sections of the head prior to rolling that portion of the hair onto the rods it is called a lotion wrap whereas when the hair i9 rolled on the rods or rollers first and then the lo~ion applied onto all of the hair after rolling, tAis is called a water wrap.
The timing for the reducing agent to be in contact with the hair for a lotion wrap is be~un from the time that all rods are on the head, and the timinq or a water wrap begins from the time that the lotion application is completed. The capability of using a water wrap i9 clearly more desirable since the lotion is applied to the entire head of hair all at once ln a short period o~
time and can be rinsed from the hair all at once to provide a more uniform reducing agent contact time for all Q~ the hair.

In accordance with the present invention, an alkaline permanent wave composition is provided in a single formula capable o~ being water wrapped with or 203~i2~

PATENT APPL I CAT ION

without the use of a dryer, heating capq or other heat treatment to speed the reducing agent reaction. The compoqition of the present invention produces a strong curl similar to alkaline wave composi~ion yet leaves the hair feeling soft like an acid wave composition without post-perm odor normally associated with thioglycolate-containing, e.g., ammonium thioglycolate-containing permanent wave composition.

Prior art alkaline compositions containing a salt of thioglycolic acid as a reducing agent are known to produce a tight curl but leave the hair feeling harsh due to the high alkalinity content. Such compositions, however, produce a distinct post-perm sulfur odor, even i~ used with cysteine, due to the presence of too high a concentration of ammonium thioglycolate; or ~uch compositions have a low perm efficacy. Prior art acid wave compositions containing glycerol monothioglycolate also leave the hair with a strong sulfur odor. Acid wave compositions generally require beat to help swell 2Q the hair for reaction with the reducing agent since the hair i8 not normally swelled sufficiently at the low p~
of the acid wave compo~itions. The cysteine, thioglycolate-based reducing agent-containing permanent wave compositions of the present invention ~olve the above mentioned prior art deficiencieq without causing a post-perm odor, even immediately after the permanent wave compo~ition is applied.

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PATENT APPLICATION

_ g _ S~MMARY OF TEE INVENTION

In brief, the present invention is directed to a mild, alkaline permanent wave redueing composition and method of permanently waving or reshaping human hair that provides a strong, long lasting curl similar to alkaline permanent wave composition but leave~ the hair soft like an acid permanent wav~ composition, without a post-perm odor. Generally, the composition contalns a cy~teine reducing agent (2-amino-3-mercaptopropionic acid) compound selected from the group consisting of cysteine, a cysteine salt, e.g., cysteine hydrochloride, and mixture-~ thereof; a monothioglycolate, e.g., ammonium thioglycolate or monothioglycolic acid ester, e.g., thioglycerol.
The cysteine compound should be present in an amount o~ about 2.0% to about 6. 5~ by weight; qenerally about 4.0~ to about 6.0%, and preferably about 5.0% by weight for normal or tinted (not 3ubstantially damaged) hair; generally about 2.0% to about 4.0%, preferably about 2.0% to about 3.0% cysteine for bleached hair; and generally about 5.0% to about 6.5% cy~teine, preferably about 6.0t for curl-resistant hair. Similarly, the amount of thioglycolate can be varied to best suit the condition of the hai~ being permanently waved. The thioglycolate should be present in an amount of about 4.5% to about 8.0% by weight, generally about 5.0% to about 7.0%, preferably about 6.0% by weight thioglycolate for normal or tinted hair; about 3.5% to about 5.5%, preferably about 4.5% by weight thioglycolate for bleached hair and about 5.5~ to about L 2 :1 PATENT APPLICATION

8.0%, preferably about 6.s% by weight thioglyco~ate for curl-resistant hair; and sufficient additional alkali, if necessary, to bring the pH of the composition to within the range of about 7.5 to about 9.5. Optionally, a hair softening and/or moisturizing agent, ~uch as glycerine is included in the composition in an amount of about 0.1% to about 20S by weight, preferably about 0.1 to about 15% by weight of the compoqition. Optionally, one or more conditioning agents, such a~ a silicone oil and/or sllicone gum; and/or a quaternary conditioning agent also is included in the composition for conditioning benefits and hair shine in an amount of about 0.1% to about 20% by weight of the composition.
Fragrances and other common additiveq also can be included in the usual amounts of about 0.1% to about 5.0% by weight of the composition. Thiq composition is easy to u-qe and apply without significantly damaging the hair while providing a strong, tight curl and leaving the hair unexpectedly soft. Quite surprisingly, the composition leaves no noticeable post-perm odor. The compoaition can be lotion or water wrapped and can be used with or without heat.

Accordingly, an a~pect of the present invention is to provide a new and improved permanent wave composition capable of breaking sulfur to sulfur bonds in human hair so that the hair can be reconfigured in a different coniguration. The sulfur to sulfur human hair bonds can be reestablished with an oxidizing agent to maintain the new hair configuration for a substantial time period.

2 ~ 3 ~

PATENT APPLICATION

Another aspect of the present invention i9 to provide a new and improved permanent wave lotion containing a combination of cysteine and thioglycolate reducing agents, in specific amounts, capable of effectively breaking sulfur to sulfur hair bonds without noticeable post-perm odor.

Another optional aspect of the present invention is to provide a permanent wave reducing agent-containing composition including a hair softening and moisturizing agent that enhance~ the 30ftness and shine achieved with the composition and without leaving a noticeable odor in the hair.

These and other aspects and advantages of the pre3ent invention will become apparent from the following detailed description of the preferred embodiment.

DETAILED ~SCRIPTION OF r~ PREYERR2D EMBODIMENT
The present invention is directed to a cysteine, thioglycolate-baaed permanent wave composition capable of permanently waving hair, uslng either a water-wrap or a lotlon wrap, applied as a mild alkallne permanent which unexpectedly leaveq the hair feeling soft like an acid wave, yet produceq a tight, long lasting curl fQrmation similar to that of an alkaline wave but without post-perm odor. The capability of permanently waving hair using a cy3teine, thioglycolate-based, reducing agent composition without leaving apost-perm odor i9 unique in the indu~try~

2 Q 3 ~ L

- PATENT APPL ICAT ION

The composition of the present invention is a mild, alkaline permanent wave conditioning compo~ition capable of waving or re~haping human hair and provides a strong, long lasting curl similar to an alkaline permanent wave composition while leaving the hair soft like an acid permanent wave composition without a po~t-perm odor. Generally, the composition contains a cysteine compound selected from tne group consisting of cysteine, a cysteine salt, and mixtures in an amount of about 2.0% to about 6.5% by weight, and a thioglycolate in an amount of about 4.5% to about 8.0S.

The reducing agent composition of the present invention has a p~ in the range of about 7.5 to about 9.5. A p~ within the desired range, depending upon the type of hair being permanently waved, can be achieved by the addition of an alkanolamine, ammonia, an ammonium carbonate, and/or a metal hydroxide to the compo~ition of the present invention. Optionally, the reducing composition also includes a hair moisturizer and/or softener selected from a polyhydroxyl alkyl compound, a polyalkylena glycol glycerol ether, an ethoxylated fatty alcohol, a fatty alcohol polyglycol ether, and mixtures thereof in an amount of about 0.1% to about 20% by weight, particularly about 0.1% to about 15% by weight.

In accordance with one optional embodiment of the present invention, the compo~ition of the present invention also include3 from about 0.1% to about 10%, particularly about 0.5~ to about 10~, and preferably from about 1.0% to about 5.0~, by waight oF a 2~3~

PATENT APPL ICAT ION

non-volatile ~ilicone compound or other conditioning agent(s), such as polymeric quaternary ammonium salts, preferably a water-insoluble, emulsiEiable conditioning agent. The preferred non-volatile silicone compound is a polydimethylsiloxane compound, such as a mixture, in about a 3:1 weight ratio, of a low molecular weight polydimethylsiloxane fluid and a higher molecular weight polydimethylsiloxane gum. The non-volatile polydimethyl~iloxane compound i5 added to the composition of the present invention in an amount sufficient to-provide improved combing and improved feel (softness) to the hair after shampooing. As referred to herein, "silicone gums" are those nonfunctional siloxanes having a vi~cosity of from about 5 to about 600,000 centistokes at 25C. The so-called rigid silicones, as described in U.S. Patent No. 4,902,499, herein incorporated by reference, having a viscosity above 600,000 centistokes at 20C, e.g., 700,000 centistokes plus, and a weight average molecular weight of at least about 500,000 also are uYeful in accordance with the present inventlon.

PreFerred silicone gums include linear and branched polydimethylsiloxanes, of the following general formula:

(C~3)3SiO - [Si(CH3)2O]n - Si~C~3)3 , wherein n is from about 2,000 to about 15,000, preferably from about 2,000 to about 7,000. Silicone 2 ~ 3 ~

PATENT APPLICATION

, gums useful in compositions of the present invention are available from a variety of commercial source~, including General Electric Company and Dow Corning.

Another particularly suitable conditioning agent that can be included in the composition of the present invention is a volatile hydrocarbon, such as a hydrocarbon including from about 10 to about 30 carbon atoms, that has sufficient volatility to slowly volatilize from the hair after application of the aerosol or non-aerosol styling aid composition. The volatile hydrocarbons provide essentially the same benefits as the silicone conditioning agent.

The preferred volatile hydrocarbon compound is lS an aliphatic hydrocarbon including from about 12 to about 24 carbon atoms, and having a boiling point in the range of from about 100C to about 300C. Exemplary volatile hydrocarbons are depicted in general structure formula (I), wherein n ranges from 2 to 5, H3C-(-f-CH2-~nc~ C~3 (I) Example~ of volatile hydrocarbons useful in the composition of the present invention are the .
commercially-available compounds PERMETHYL 99A and PERMET~YL lOlA, corresponding to compounds of general structure (I), wherein n is 2 and 3, respectively, 2~39~

PATENT APPLICATION
27697~3~23 available from Permethyl Corporation, ~razer, ; Pennsylvania. A volatile hydrocarbon compound is useful in the composition of the present invention either alone, in combination with another volatile hydrocarbon, or in combination with a volatile silicone.

Examples of other suitable water-insoluble conditioning agents that can be incorporated into the permanent wave compo~itions include the polymeric quaternary ammonium salts, such as Polyquaternium 1 through Polyquaternium 14, inclusive, and any combination of such conditioners, as deined on page 245, CT~A Cosmetic Ingredient Dictionary, Third Edition, 1982, hereby incorporated by reference. The preferred conditionerq are Polyquaternium-4, Polyquaternium-10, lS and Poly~uaternium-ll. The conditioner, when added, i9 included in an amount of about 0.01% to about 2.0~ by weight of the composition.

Other common cosmetic additives can be incorporated into the composition of the present lnvention, as long as the basic propertie~ of the permanent wave composition are not substantially adver~ely affected. These additives include, but are not limited to, commonly used fragrances, dyes, opaciiers, pearlescing agents, thickeners, foam stabilizers, preservative , water sotening agent3, acid~, ba~eq, buffers and the like; and will usually be present in weight percentages of less than about 1%
each, and about 2% to about 5% in total. The composition vehicle is predominantly water but organic solvents also can be added to the composition in order 203~ 2:~.

PATENT APPLICATION

to solubilize compounds that are not sufficiently soluble in water. Suitable solvent~ include the lower alcohols such as ethanol and isopropanol and mixtures.
These ~olvents can be present in the hair setting composition of the present invention in an amount from about lS to about 75~ by weight and in particular from about 5~ to about 50t by weight, based on the total weight of the composition.

The composition optionally can be thickened, for example, with sodium alginate, gum arabic, cellulose derivatives such as methylcellulose, hydroxyethyl-cellulose, hydroxypropylmethylcellulose and carboxymethylcellulose, and various polymeric thickeners, such as polymers of acrylic acid or polymeric acrylic acid derivatives. It is also possible to use inorganic thickeners such as bentonite. These thickeners, when included, preferably are present in an amount from about 0.1~ to about 10% by weight and, in particular, rom about 0.5% to about 3% by weight, based on the total weight of the composition.

The optional use of polyhydric alcohols or polyhydroxy alkanP compounds, such as ethylene glycol, glycerine, propylene glycol, or polyoxyethylene glyceryl ethers in this composition leaves the hair in better condltion due to humectant properties and provides the ha~ir with a more uniform and natural curl.

These moi~turizers are 3elected from the group consisting of polyhydroxyalkyl compounds, particularly alkylene glycols and polyalkylene glycols, and 2 ~ 2 -i PATENT APPLICATION

especially ethylene glycol and the polyethylene glycols;
propylene glycol and the polypropylene glycols;
polyethylene glycol glyceryl ethers; ethoxylated fatty alcohols; and fatty alcohol polyglycol ethers. Example3 of suitable moisturizers include glycols and triols ~uch as glycerine, ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,2,6-hexanetriol, l,S-pentanediol, 2-ethyl pentanediol-2,4, and 2-ethyl hexanediol-1,3.
Further examples of suitable moisturizers include the polyalkylene glycols, such as those compounds having the formula H-(oc~2lH) R

wherein R i9 ~ or C~3, and n has an average value of 2 to 600; when R=~, particularly suitable moisturizers have n in the range of 4 to 6Q0: and when R=C~3, particularly ~uitable moisturizers have n in the range of 2 to 34. The optional polyalkylene glycols that can be u~ed a~ moi~turizers in the permanent wave compo~ition of the present invention are exemplified by, but not limited to, compounds such as polyethylene glycol 200; polyethylene glycol 400; polyethylene glycol 600; polyp~opylene glycol lS0; tetraethylene glycol; and dipropylene glycol.

Examples o~ other suitable moisturizers include the polyethylene glycol glyceryi ethers, such as polyethylene glycol 600 glyceryl ether and polyethylene glycol 26 glyceryl ether. Furthermore, the ethoxylated nonyl phenols and ethoxylated octyl phenol~, .

2~3~

PATENT APPL ICATION

particularly nonoxynol, CgHlgC6H4(OCH2CH2)n~O~r wherein n averages at least 6 and up to about 100; and octoxynol, C8H17S6~4(C~2CH2)n-~H~ wherein n averages at least 7 and up to about 40, also are suitable moisturizers for use in the composition of the present invention. Suitable ethoxylated fatty alcohol~ for use as moisturizers in the composition of the present invention include compounds having the formula R-(OC~2C~2)nOH, wherein R is an alkyl group containing from about 12 to about 30 carbon atoms and n averages at least 6. In addition, fatty alcohol polyglycol ethers having the formula R-~OC~I2C~I2)n~(0CH21~)m ~' c~3 wherein R is an alkyl group containing from about 8 to about 18 carbon atoms, n=0 to 6, m=0 to 6, and n+m is at lea~t 6, also are useful as moi~turizers in the composition of the present invention.
The composition of the present lnventlon i9 easy to use and apply without post-perm odor whlle providing a strong, tight curl and leaving the hair unexpectedly soft. The composition can be lotion or water wrapped and can be used with or without heat.

~ our reducing agent-containing compositions were prepared containing cysteine and ammonium thioglycolate. It is understood that cysteine performs the same reducing agent function as its salt~, such as . . .

2 ~ 2 :i PATENT APPLI~ATION

the strong mineral acid salts, e.g., salts formed from phosphoric or sulfuric acids, and the like, e.g., cysteine hydrochloride.

Four reducing agent compositions of the present invention were prepared as follows:

COMPOSITION 1 (p~:9.1) NORMAL ~AIR

. . _ WATER, DEIONIZED 79.30 %
AMMONIUM T~IOGLYCOLATE (60%) 10.00 %
SODIUM ~YDROXIDE (50%) 1.50 %
INCROMECTANT AQ (MOISTURIZER) 1.00 %
15 GLYCERIN USP 2.00 POLYSORBATE 20 (FRAGRANCE
SOLUBILIZER) ,90 %
FRAGRANCE .30 %
AMMONIUM ~YDROXIDE (28~) to p~:9.1 L-CYSTEINE FREE ~ASE 5.00 %
10'0. 00 %
20 COMMENTgs Excellent curl, no odor.
I

2~3~

PATENT APPLICATION

COMPDS m ON 2 ~pH:8.8) NORMhL ~AIR

INGREDIENT PERCENT BY WEIGHT
WATER, DEIONIZED 81.47 L-CYSTEINE P~EE BASE 5.00 5 AMMONIUM THIOGLYCOLATE (60%) 8.33 AMMONIUM BICARBONATE 2.00 %
IGEPAL C0-730 (FRAGRANCE
SOLUBILIZER) 0.90 %
PRAGRANCE .O.30 INCROMECTANT AQ (MOISTURIZER) 2.00 %
AMMONIUM HYDROXIDE to pH:8.8 100.00 COMMENTS: Excellent curl, no odor.

COMPOSITION 3 (pH:7.5) BLEA~H~ ~AIR
15 INGREDIENT PERCENT 8Y WEIG~T
~ATER, DEIONIZED 84.30 AMMONIUM T~IOGLYCOLATE l60%) 7.50 AMMONIUM BICARBONATE 2.00 INCROMECTANT AQ (MOISTURIZER) 1.00 GLYCERIN USP 2.00 20 POLYSOR8ATE 20 ~FRAGRANCE
SOLUBILIZER) 0.90 AMMONIUM HYDROXIDE (28%) to pH:7.5 L-CYSTEINE FREE BASE 2.00 100 . 00 CO~MENTS: Excellent curl, no odor.

2 0 3 ~ i ~d 1.

PATENT APPLICATION

COMPOSITION 4 (pH:9.5) RESISTANT ~AIR

INGREDIENT PE~CENT BY WEIGHT
WATER, DEIONIZED 77.45 AMMONIUM THIOGLYCOLATE t60%)10.85 5 SODIUM HYDROXIDE (50%) 1.50 INCROMECTANT AQ (MOISTURIZER) 1.00 GLYCERIN USP 2.00 POLYSOR~ATE 20 ~FRAGRANCE
SOLUBILIZER) 0.90 FRAGRANCE .30 AMMONIUM HYDROXIDE ~28%) to pH:9.5 L-CYSTEINE FREE ~ASE 6.00 100.00 3 COMMENTS: Excellent curl, no odor.

The reducing agent-containing Composition 1 was test applied to heads of hair in the Helene Curtis, Inc. Salon Testing Center. The reducin~ agent Composition 1 was oxidized with a hydrogen peroxide-based neutralizer. None of the test subje~ts commenting on the permanent wave compoqition noticed any post-perm odor and all sub~ectc were very pleased wlth the soft, natural feel left in the air. Similarly, compositions 2, 3 and 4 leave no post-perm odor in the hair.

203~72~

PATENT APPLICATION
. 27697/3023 The following prior art composition 5, as di2closed in U.S. Patent No. 4,913,900, produces an excellent curl, but leaves the hair with a strong po~t-perm odor:

COMPOSITION S (pH:8.4) PRIOR M T
~ .
WATER, DEIONIZED 69.40 AMMONIUM THIOGLYCOLATE (60%)22~90 %
DIAMMONIUM DIT~IODIGLYCOLATE (40%) 1.00 %
10 AMMONIUM HYROXIDE (28%) to pH:8.4 AMM~NIUM 8ICARBONATE 2.00 %
GLYCERIN USP 3.50 POLYSORBATE 20 (FRAGRANCE
SOLULILIZER) 0.90 FRAGRANCE 0.30 %
100.00 COMMENTS: Excellent curl, strong odor.

PATENT APPLICATION

The following composition 6, containing too little thioglycolate did not leave the hair with a post-perm odor, but provided very poor curl:

S COMPOSITION 6 (p~:9.2) INGREDIENT PE~CENT BY WEIG~T
WATER, DEIONIZED 79.75 10 L-CYSTEINE 5.00 EDTA 0.10 AMMONI~M T~IOGLYCOLATE (50~) 2.00 %
MONOET~ANOLAMINE (pH) 3.00 AMMONIUM ~YDROXIDE (28%)to pH:9.2 EMACOL X-606E (CONDITIONER) 10.0`Q
PERFUME HC-2221-~ 0.06 LATEX E-30a (OPACIFIER) 0.05 %
D & C YELLOW #10 (2S) 0.04 %
ioo . oo %

CO~MENTS: ~ittle to no curl, no odor Obviously, many modifications and variations of the invention as hereinbefore set forth can be made without departing from the spirit and acope thereof and therefore only such limitations ahould be impo~ed as are indicated by the appended claims.

Claims

1. A composition capable of breaking sulfur to sulfur bonds in human hair for permanently waving hair when in contact with said human hair so that said hair can be reconfigured in a predetermined configuration, comprising an aqueous solution of a cysteine compound selected from the group consisting of cysteine, a salt of cysteine, and mixtures thereof in an amount of about 2.0% to about 6.5% by weight; an alkaline thioglycolate in an amount of about 4.5% to about 8.0% by weight; and sufficient alkali such that the composition has a pH of about 7.5 to about 9.5.

2. The composition of Claim 1, wherein the cysteine is present in the composition in an amount of about 4.0% to about 6.0% by weight of the composition;
the thioglycolate is present in the composition in an amount of about 5.0% to about 7.0% by weight of the composition; and the composition has a pH in the range of about 9.0 to about 9.5.

3. The composition of Claim 1, wherein the cysteine compound is included in an amount of about 5.0%
to about 6.5% by weight of the composition; wherein the alkaline thioglycolate is included in an amount of about 5.5% to about 7.5% by weight of the composition and the pH is in the range of about 9.0 to about 9.5.

4. The composition of Claim 1, wherein the cysteine compound is included in an amount of about 2.0%
to about 4.0% by weight of the composition; wherein the PATENT APPLICATION

alkaline thioglycolate is included in an amount of about 3.5% to about 5.5% by weight of the composition, and the pH is in the range of about 7.5 to about 8.5.

5. The composition of Claim 1 further including a polyhydric moisturizer in an amount of about 0.1% to about 20% by weight of the composition, and wherein the polyhydric moisturizer is selected from the group consisting of polyhydroxyalkyl compounds;
polyalkylene glycols; glyceryl ether compounds;
ethoxylated fatty alcohols; ethoxylated alkyl phenols;
fatty alcohol polyglycol ether compounds; and mixtures thereof.

6. The composition of Claim 1, wherein the alkaline thioglycolate is ammonium thioglycolate.

7. The composition of Claim 2, wherein the alkaline thioglycolate is ammonium thioglycolate.

8. The composition of Claim 3, wherein the alkaline thioglycolate is ammonium thioglycolate.

9. The composition of Claim 4, wherein the alkaline thioglycolate is ammonium thioglycolate.

10. The composition of Claim 1 further including a conditioning agent selected from the group consisting of a silicone and a polymeric quaternary ammonium compound, in an amount of about 0.1% to about 20% by weight of the composition.

PATENT APPLICATION

11. A composition capable of breaking sulfur to sulfur bonds in human hair for permanently waving hair when in contact with said human hair so that said hair can be reconfigured in a predetermined configuration, comprising an aqueous solution of a cysteine compound selected from the group consisting of cysteine, a salt of cysteine, and mixtures thereof in an amount of about 2.0% to about 6.5% by weight; an alkaline thioglycolate in an amount of about 4.5% to about 8.0% by weight; and sufficient alkali such that the composition has a pH in the range of about 7.5 to about 9.5.

12. The composition of Claim 11 further including a polyhydric moisturizer in an amount of about 0.1% to about 20% by weight of the composition, and wherein the polyhydric moisturizer is selected from the group consisting of polyhydroxyalkyl compounds;
polyalkylene glycols; glyceryl ether compounds:
ethoxylated fatty alcohols; ethoxylated alkyl phenols;
fatty alcohol polyglycol ether compounds; and mixtures thereof.

13. The composition of Claim 12, wherein the cysteine is present in the composition in an amount of about 4.0% to about 6.0% by weight of the composition;
the thioglycolate is present in the composition in the amount of about 5.0% to about 7.0% by weight of the composition; and the composition has a pH in the range of about 9.0 to about 9.5.

PATENT APPLICATION

14. The composition of Claim 12, wherein the cysteine compound is included in an amount of about 5.0%
to about 6.5% by weight of the composition; wherein the alkaline thioglycolate is included in an amount of about 5.5% to about 7.5% by weight of the composition, and the pH is in the range of about 9.0 to about 9.5.

15. The composition of Claim 12, wherein the cysteine compound is included in an amount of about 2.0%
to about 4.0% by weight of the composition; wherein the alkaline thioglycolate is included in an amount of about 3.5% to about 5.5% by weight of the composition, and the pH is in the range of about 7.5 to about 8.5.

16. A method of breaking sulfur to sulfur bonds in human hair to leave the hair weakened so that it can be reconfigured to a predetermined configuration, including contacting the hair with an aqueous reducing agent-containing composition comprising about 2.0% to about 6.5% by weight of a cysteine compound selected from the group consisting of cysteine, a salt of cysteine, and mixtures; about 4.5% to about 8.0% of an alkaline thioglycolate; and sufficient alkali such that the composition has a pH of about 7.5 to about 9.5;
forming the hair in a desired configuration such that the hair is in contact with the reducing agent-containing composition for a predetermined amount of time while formed in the new configuration; and then removing most of the reducing agent-containing composition from the hair at the expiration of the predetermined time period.

PATENT APPLICATION

17. The method of Claim 16, further including wrapping a plurality of human hair sections around a plurality of mandrels to reconfigure the hair sections in a plurality of curl configurations such that the hair is curl-configured while in contact with the reducing agent-containing composition; and removing the mandrels sequentially after said predetermined time period without testing the hair from one of the first removed mandrels for curl tightness.

18. The method of Claim 16, wherein the cysteine is present in the composition in an amount of about 4.0% to about 6.0% by weight of the composition;
the thioglycolate is present in the composition in an amount of about 5.0% to about 7.0% by weight of the composition; and the composition has a pH in the range of about 9.0 to about 9.5.

19. The method of Claim 16, wherein the cysteine compound is included in an amount of about 5.0%
to about 6.5% by weight of the composition; wherein the alkaline thioglycolate is included in an amount of about 5.5% to about 7.5% by weight of the composition, and the pH is in the range of about 9.0 to about 9.5.

20. The method of Claim 16, wherein the cysteine compound is included in an amount of about 2.0%
to about 4.0% by weight of the composition; wherein the alkaline thoqlycolate is included in an amount of about 3.5% to about 5.5% by weight of the composition, and the pH is in the range of about 7.5 to about 8.5.