Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3847165 A
Publication typeGrant
Publication dateNov 12, 1974
Filing dateAug 15, 1973
Priority dateAug 15, 1973
Also published asCA1034502A, CA1034502A1, DE2437084A1
Publication numberUS 3847165 A, US 3847165A, US-A-3847165, US3847165 A, US3847165A
InventorsPatel K, Reiss C
Original AssigneeRedken Laboratories Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Acidic permanent waving solution and process for its use
US 3847165 A
Abstract
There is provided a two stage acidic waving system of improved properties with respect to reduced irritation and hair destruction.
Images(5)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

United States Patent [191 Patel et al.

[ 1 Nov. 12, 1974 ACIDIC PERMANENT WAVING SOLUTION AND PROCESSFOR ITS USE Inventors: Kanu I. Patel, Chatsworth; Carroll R. Reiss, Los Angeles, both of Calif.

Redken Laboratories, Inc., Van Nuys, Calif.

Filed: Aug. 15, 1973 Appl. No.: 388,385

Assignee:

U.S. Cl 132/7, 424/71, 424/72 Int. Cl A45d 7/00 Field of Search 132/7; 424/71, 72

References Cited UNITED STATES PATENTS 5/1955 DeMytt 132/7 5/1958 Hervey 132/7 5/1958 Watson 424/71 8/1958 Brown 424/72 11/1963 Shans'ky 1. 424/72 Primary E,\'ami'nerG. E. McNeil] Attorney, Agent, or Firm Christie, Parker & Hale [57] ABSTRACT There is provided a two stage acidic waving system of improved properties with respect to reduced irritation and hair destruction.

Following hair treatment with the waving solution, the hair is neutralized in a conventional manner and styled.

25 Claims, N0 Drawings A CIDIC PERMANENT WAVING SOLUTION AND PROCESS FOR ITS USE BACKGROUND OF THE INVENTION Alkaline permanent wave solutions containing urea and a thiol, such as ammonium thioglycolate have been reported in the literature, for instance, in US. Pat. Nos. 2,708,940 and 2,717,228. In using these solutions, maximum deformation of the hair is attained with an ammoniacal thiol solution used on unprocessed and bleached human hair at solution pH between 8.0 and 10.

Reduction of the hair with mercaptans is accompanied by substantial swelling of the hair under alkaline conditions.

Swelling is as important as the reduction process itself. Rate of reaction increases with pH and temperature and has been reported to depend on the extent of ionization of the mercaptan group of the thiol acid, such as ammonium thioglycolate.

Reaction between the hair and the ammonium thioglycolate rapidly reaches an equilibrium with the extent of reaction depending upon the amount of thioglycolate applied to the hair.

Solutions heretofore employed have exhibited the problems of an undesirable odor due to ammonia emission and have also been highly irritating to the skin and eyes as well as destructive to the hair.

SUMMARY OF THE INVENTlON According to the present invention, there is provided a two stage acidic hair waving system for use in commercial hair waving and styling operations and a process for using the solutions.

The first stage at least consists of urea and/or its alkyl inclusion derivatives and is normally dry.

The second stage is a solution containing water, a water soluble thiol, such as ammonium thioglycolate, and a water soluble hair protein.

There may be present in the first and/or second stage a bicarbonate compound and/or borax.

Prior to use, urea or its derivative is dissolved to form an aqueous acidic waving solution. The solution contains urea or its derivatives in a concentration from about I to about 4 molar, a water soluble thiol, preferably ammonium thioglycolate, in a concentration from about 0.8 to about 1.4 molar, a bicarbonate compound in a concentration of from to about 0.6 molar, borax in a concentration from O to about 0.007 molar, protein in an amount from about 2 to about 5 percent by weight based on the total weight of the solution, the solution having the pH from about 6 to about 6.8.

The use, the reforming solution is applied to the hair which is processed at a temperature from about 1 10 to 130F for a period of from about 5 to 30 minutes.

After rinsing the solution from the hair, there is applied a conventional neutralizing or rebonding solution to assure rebonding of the hair ends, then thoroughly rinsed in warm water following which, the hair is styled.

The reforming solutions of this invention are unique as to prior art solutions in that the rate of reaction with hair may be better controlled because the igni ation of the mercaptan group of the thiol is dependent solely on heat and not pH.

In addition, ammonia is not evolved as an irritant, and therefore there is less irritation to skin and eyes.

In the combination, urea is used to swell the hair sufficiently to permit penetration of the thiol which acts as the bond breaker for sulfur in the hair.

Further, it has been found that the protein is more stable in the acid medium and will not further hydrolize as in an alkaline waving solution. Borax when present provides a better curl pattern and also serves as a buffer in conjunction with bicarbonate compound to control pH.

DESCRlPTlON According to the present invention, there is provided a novel acidic waving solution and process for its use in the styling of hair.

The waving solution is a two stage system, first stage of which comprises urea and its inclusion monoalkyl derivatives, such as methyl urea and ethyl urea preferably in a dry form or, if desired, in an aqueous solution.

The second stage of the solution consists of an aqueous solution of a thiol compound, and a conventional water soluble hair protein.

In the preferred embodiment, a bicarbonate compound and borax is present, either being provided from the first or second stage, preferably from the first stage.

The urea and/or its derivatives and any of the contained additions is mixed to form a resultant aqueous solution to what may be termed a reforming solution, in which urea and/or its inclusion derivatives concentration is from about l to about 4 molar, a thiol, such as ammonium thioglycolate is present in a concentration fromabout 0.8 to about 1.4 molar, abicarbonate compound in a concentration from 0 to about 06 molar, borax in a concentration from 0 to about 0.007 molar, hair protein in an amount from about 2 to about 5 percent by weight based on the total weight of the solution, the net solution having a pH from about 6 to about 6.8.

Because urea is not stable in the solution over long periods of time, evolving ammonia which causes the pH of the solution to increase, a two stage system is necessary in order to assure that the waving solution will be acidic in nature at the time of use.

For this reason, the urea or its functional derivatives and any additional ingredients present are added at the time of use and dissolved in the aqueous solution containing the remaining constituents to provide the net composition set forth above.

As used herein, the term thiol is intended to include a water soluble compound containing a sulfhydryl or mercaptan group as the hair reducing agent. Conventional thiols are those comprising strong polar groups, such as ammonium thioglycolate, sodium thioglycolate, sodium and ammonium salts of mercaptoethylenesulfonic acid and 3-mercapto-2- hydroxypropanesulfonic acid and the like. The preferred thiol is ammonium thioglycolate.

By urea or its inclusion derivatives" there is meant urea and low molecular weight monoalkyl derivatives of urea, such as methyl and ethyl urea.

By a hair protein" there is meant, in general, conventional hydrolysis derivatives of collagen which has been reduced in molecular weight to render the protein water soluble.

In the solutions employed in the practice of this invention, the urea or urea inclusion derivatives, the thiol and the proteins are those conventionally used in hair waving solutions, whether hot or cold.

What is unique with respect to the waving solutions employed in accordance with the practice of this invention is that they are acidic as opposed to alkaline in nature. The reactions of the solutions are specific to the extent that essentially only the sulfur bonds are affected, while peptide linkages are not affected to any extent as in alkaline waving solutions, As a consequence, hair damage is less. There is no emission of irritating ammonia, and the solutions are therefore less irritating to skin and eyes. Further, the protein present has been found to be more stable and not hydrolyzed as in alkaline waving solutions.

In the waving solutions of this invention, urea or its inclusion derivatives, serve as a swelling agent for hair to facilitate reduction of the sulfur bonds by the thiol under hair dryer techniques employed.

Borax, when present, improves curl patterns and also acts as a buffer in conjunction with the bicarbonate compound consisting of ammonium bicarbonate, an alkali metal bicarbonate such as sodium or potassium bicarbonate as well as mixtures thereof which, when present, maintains the solution at the desired pH.

ln use, it has been found, because an acidic medium is employed, that the rate of reaction of the reforming solution with hair may be more easily controlled because of the ionization of the mercaptan group of the thiol compound is solely dependent on heat and not pH.

While not bound by theory, the reforming solution, because it is employed at a pH below 7, and hair is subsequently oxidized at a pH of about 6.1, there is continuity of pH with no material shift in hydrogen bonds and salt linkages.

As indicated, the protein reforming solution of this invention is prepared by the addition of urea and/or its derivatives alone or with other constituents, if present, as solid crystals or in solution to provide the activated solution of the nature described above.

The resultant acidic reforming solution may be applied to all types of hair, with normal precautions and where the beauty aid patronss scalp is void of abrasions and the like.

Care should, of course, be taken, in the usual manner, to prevent eye or skin contact. Should the solution accidentally contact the skin or the scalp, it should be blotted, without wiping, with water soaked cotton, following which is applied a bonding solution hereinafter described which is then blotted with water soaked cotton to remove solution residue.

As the urea and/or its derivatives, and any contained additives is dissolved to form the protein reforming solution, agitation is normally required where the urea and/ or its derivatives is provided as a solid. Mere shaking of the mixture is sufficient to achieve solution.

The hair is first shampooed, towel dried and predampened with the reforming solution and conventional styling wrapping procedures followed, using selected proper sized rods for the desired curl configuration.

4 Following wrapping a d ryer is pr'afireata'dihi perature from about 1 10 to about 130F, and each desired curl saturated with the protein reforming solution. A thin plastic cap or similar covering is then applied over the entire head making sure that all applied rods are covered and that the applied cap snugly fits around the hair line.

The patron is then placed under the preheated dryer making sure that the heat provided reaches all areas of the hair including the nape. Care should be taken to test curls aproxima tely every 5 minutes for normal hair and about every 2 to 3 minutes for tinted hair.

When the hair forms the desired pattern which may range over a time period from about 5 to about 30 minutes, the hair is rinsed with warm water for a period of about 3 to about 5 minutes.

Each curl is then thoroughly squeezed with a towel to remove excess moisture to insure thorough bonding ane conditioning action of the subsequent applied neutralizing solution.

There is then applied an acidic protein bonding or neutralizing solution (pH about 6.1) which are typically aqueous solutions containing oxidizing agents such as hydrogen peroxide, potassium bromate, alkali metai perborates, such as sodium and potassium perborate, and the like, as well as mixture thereof, which neutralizes the redox effect of the reforming solution. That is to curb reduction of the hair while the reforming solution is oxidized. This also constitutes a rebonding operation to assure rebonding of the hair ends.

As presently preferred, the neutralizing solution is allowed to remain in the hair for at least 5 minutes for complete bonding an conditioning.

the rods are then removed and the neutralizing solution thoroughly worked through the hair to insure rebonding of the hair ends.

The hair is then thoroughly rinsed withtepid water and styled in the usual manner to the desired end result.

The presently preferred reforming solution of this invention have the following composition:

Urea l to 4 M Ammonium thioglycolate 0.8 to 1.4 M

NaHCO 7 to 50 grams/liter Borax (Na B,O -l0H O) 0 to 2.5 grams/liter Protein 2 to 5 percent by weight Balance Water pH 6.0 to 6.8

While nowise limiting, the following are illustrative examples of the acidic reforming solutions of this in vention.

EXAMPLES l to 6 -The following are representative compositions found useful as acidic waving solutions found useful in combination with neutralizing solutions for hair styling. Each component is listed in the typical concentration employed, the balance of the solution being water. The formations are shown in Table I.

TABLE 1 Examples Component l 2 3 4 5 6 Urea (moles/liter) 2.0 2.7 3.0 3.0 2.7 2.0 Ammonium thioglycolate (moles/liter) 1.4 1.2 L3 L3 1.2 1.4 Sodium bicarbonate (gms/lOO grams of 5.0 0.8 L0 0 O 0 solution) Borax (gms/IOO grams of solution) 0 0 0.25 0.25 0 V 0 Protein by weight of solution) 2.0 2.0 2.0 2.0 2.0 4.0

. Solution pH 6.7 6.5 6.5 6.6 6.8 6.8

What is claimed is:

l. A two stage acidic composition for use in waving operations which comprises:

a. a first stage comprising a urea compound selected from the group consisting of urea, methyl urea, ethyl urea and mixtures thereof;

b. a second stage comprising water, a water soluble thiol and a water soluble protein;

the addition of said first stage to said second stage alone or by the addition of water forming a net solution having a pH between about 6.0 and about 6.8, said net solution having a urea compound concentration of from about 1 to about 4 molar; a water soluble thiol concentration of from about 0.8 to about 1.4 molar and a water soluble protein content of from about 2 to 5 percent by weight based on the total weight of the net solution.

2. A two stage acidic composition as claimed in claim 1 in which the water soluble thiol is ammonium thioglycolate.

3. A two stage acidic composition as claimed in claim 1 in which a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereof is present in the net solution in an amount up to about 0.6 molar.

4. A two stage composition as claimed in claim 3 in which the bicarbonate compound is contained in the first stage.

5. A two stage composition as claimed in claim 3 in which the bicarbonate compound is contained in the second stage.

6. A two stage acidic composition as claimed in claim 2 in which a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereo is present in the net solution in an amount up to about 0.6 molar.

7. A two stage acidic composition as claimed in claim 1 in which borax is present in the net solution in an amount up to about 0.007 molar.

8. A two stage composition as claimed in claim -7 in which the borax is contained in he first stage.

9. A two stage acidic composition as claimed in claim 7 in which the borax is contained in the second stage.

10. A two stage acidic composition as claimed in claim 3 in which borax is present in the net solution in an amount up to about 0.007 molar.

11. A two stage acidic composition as claimed in claim 4 in which the borax is contained in the first stage.

12. A two stage acidic composition as claimed in claim 4 in which the borax is contained in the second stage.

13. A two stage acidic composition as claimed in claim 5 in which the borax is contained in the first stage.

14. A two stage acidic composition as claimed in claim 5 in which the borax is contained in the second stage.

15. A two stage acidic composition for use in hair waving operations which comprises:

a. a first comprising a urea compound selected from the group consisting of urea. methyl urea. ethyl urea and mixtures thereof, a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereof and borax;

b. a second stage comprising water, a'water soluble thiol, and a water soluble protein;

the addition of said first stage to said second stage alone or with the addition of water forming a net solution having a pH between about 6.0 and about 6.8, said net solution having a urea compound concentration of from about 1 to about 4 molar, a water soluble thiol concentration of from about 0.8 to about 1.4 molar, a bicarbonate compound concentration up to about 0.6 molar, borax in a concentation up to about 0.007 molar and a water soluble protein content of from about 2 to about 5 weight percent by weight based on the total weight of the net solution.

16. A two stage acidic composition as claimed in claim 15 in which the water soluble thiol is ammonium thioglycolate.

17. A two stage acidic composition for use in hair waving operations which comprises;

a. a first stage comprising a urea compound selected from the group consisting of urea, methylurea, ethyl urea and mixtures thereof;

b. a second stage comprising an aqueous solution of a water soluble thiol, a bicarbonate compound selected from the group consisting of ammonium bicaronate, an alkali metal bicarbonate and mixtures thereof; borax, and a water soluble protein;

the addition of said first stage to said second stage alone, or by dilution with water forming a net solution having a'pH between about 6.0 and about 68, said net solution having a urea compound concentration of from about 1 to about 4 molar; a water soluble thiol concentration of from about 0.8 to

about 1.4 molar, a bicarbonate compound concentration up to about 0.6 molar, borax concentration up to about 0.007 molar and a water soluble protein content of from about 2 to about 5 percent by weight based on the total weight of the net solution.

said net solution having a urea concentration of from about 1 to about 4 molar; an ammonium thioglycolate concentration of from about 1 to about 4 molar; an ammonium thioglycolate concentration of from about 0.8 to about 1.4 molar, ammonium bicarbonate in a concentration of from 0 to about 0.6 molar, borax in a concentration of from 0 to about 0.007 molar and a water soluble protein content of from about 2 to about 5 percent by weight 7 based on the total weight of the net solution.

20. A process for conditioning hair for styling which comprises:

a. treating hair strands in an aqueous acidic reforming solution having a pH between about 6.0 and about 6.8, and containing a urea compound selected from the group consisting of urea, methyl urea, ethyl urea and mixtures thereof in a concentration from about i to about 4 molar; a water solubie thiol in a concentration in an amount of about 0.8 to about 1.4 molar, sodium bicarbonate in a concentration from O to about 0.6 molar, borax in a concentration from O to about 0.007 molar and 5 water soluble protein in an amount of from about 2 to about 5 percent by weight based on the total weight of the solution;

b. heating the treated hair strands to a temperature from about 1 to about 130F for a time sufficient 10 to provide a waving condition;

c. rinsing the hair to remove at least a substantial portion of the reforming solution; d. applying to the hair a neutralizing solution contain ing at least one oxidizing agent; e. rinsing the hair with water and setting the hair. 21. A process as claimed in claim in which the urea compound in the aqueous acidic reforming solu- 'tion is urea and the thiol i'sm'rhohium thioglycolate.

22. A process as claimed in claim 20 in which the neutralizing solution contains an oxidizing agent selected from the group consisting of hydrogen peroxide, potassium bromate, an alkali metal perborate and mixtures thereof.

23. A process as claimed in claim 21 in which the neutralizing solution contains an oxidizing agent selected from the group consisting of hydrogen peroxide, potassium bromate, alkali metal perborate and mixtures thereof.

24. A process as claimed in claim 20 in which the treated hair strands are heated for a period of time from about 5 to about 30 minutes.

25. A process as claimed in claim 21 in which the treated hair strands are heated for a period of time from about 5 to about 30 minutes.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2708940 *Jul 27, 1953May 24, 1955Gillette CoComposition and method of cold waving
US2836185 *May 27, 1954May 27, 1958Little Inc AProcess of permanently setting hair with a hair-swelling solution of a bisulfite and a nitrogen-containing component
US2836543 *May 27, 1954May 27, 1958Little Inc ASulfite hair waving composition comprising a nitrogen-containing compound and a substituted aromatic compound as additive, and method of use
US2847351 *Nov 8, 1955Aug 12, 1958Gillette CoHair waving composition comprising a disulfide and either a non-corresponding mercaptan or thiourea dioxide
US3109778 *Mar 16, 1961Nov 5, 1963Turner Hall CorpPermanent waving compositions comprising 2, 2, 2-trichloro-1, 1-ethanediol
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4044782 *Mar 26, 1976Aug 30, 1977The Procter & Gamble CompanyAcid treated polyester polyurethane foam end wrap
US4054722 *Jun 23, 1976Oct 18, 1977Fuji Photo Film Co., Ltd.Acyloxy substituted acrylate timing layers for color diffusion transfer
US4105038 *Mar 26, 1976Aug 8, 1978The Procter & Gamble CompanyAcid treated polyether polyurethane foam end wrap
US4134411 *Feb 9, 1976Jan 16, 1979Ikue YamazakiAcidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
US4228810 *Nov 20, 1978Oct 21, 1980La Maur Inc.Care and treatment of curly human hair
US4313933 *Mar 4, 1977Feb 2, 1982Ikue YamazakiAcidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
US7754193May 18, 2004Jul 13, 2010L'oreal S.A.Reducing composition for permanently reshaping keratin fibers and permanent-reshaping process
US8906352Jan 29, 2013Dec 9, 2014L'orealMethod for straightening human hair fibers using heating means and an α-hydroxy acid derivative
US9743736Oct 18, 2016Aug 29, 2017L'orealMethod for straightening human hair fibers using heating means and malic acid
US20050112076 *May 18, 2004May 26, 2005Thomas FondinReducing composition for permanently reshaping keratin fibers and permanent-reshaping process
EP0101887A2 *Jul 21, 1983Mar 7, 1984Helene Curtis Industries, Inc.Cosmetic compositions comprising an aqueous solution of an urea compound, hair treatment, skin moisturizer, hair waving system, retardation of alkali production, and hair and skin treatment methods
EP0101887A3 *Jul 21, 1983May 15, 1985Helene Curtis Industries, Inc.Cosmetic compositions comprising an aqueous solution of an urea compound, hair treatment, skin moisturizer, hair waving system, retardation of alkali production, and hair and skin treatment methods
EP0102495A2 *Jul 21, 1983Mar 14, 1984Helene Curtis Industries, Inc.Hair waving system and lotion, and method of waving hair
EP0102495A3 *Jul 21, 1983May 15, 1985Helene Curtis Industries, Inc.Hair waving system and lotion, and method of waving hair
EP0628301A1 *Mar 29, 1994Dec 14, 1994Wella AktiengesellschaftComposition and process for permanent waving of hair
EP2826461A1Nov 14, 2005Jan 21, 2015L'OréalMethod for straightening keratin fibres using a heating means and a denaturing agent
EP3141284A1May 23, 2007Mar 15, 2017L'OréalMethod of straightening keratinous fibers using heating means and an acid derivative
Classifications
U.S. Classification132/204, 424/70.2
International ClassificationA45D7/04, A61K8/20, A61K8/00, A61Q5/04, A61K8/46, A45D7/00, A61K8/19, A61K8/30, A61K8/42, A61K8/64, A61K8/65, A61K8/22, A61K8/40
Cooperative ClassificationA61K8/64, A61K8/42, A61Q5/04, A61K8/65
European ClassificationA61K8/65, A61K8/42, A61Q5/04, A61K8/64
Legal Events
DateCodeEventDescription
Jun 24, 1993ASAssignment
Owner name: REDKEN LABORATORIES, INC.
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BANK OF AMERICA NATIONAL TRUST AND SAVINGS ASSOCIATION, SUCCESSOR BY MERGER TO SECURITY PACIFIC NATIONAL BANK;REEL/FRAME:006589/0164
Effective date: 19930621
Nov 23, 1988ASAssignment
Owner name: SECURITY PACIFIC NATIONAL BANK
Free format text: SECURITY INTEREST;ASSIGNOR:REDKEN LABORATORIES, INC.;REEL/FRAME:004993/0486
Effective date: 19880913