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Publication numberUS3823232 A
Publication typeGrant
Publication dateJul 9, 1974
Filing dateMar 1, 1971
Priority dateJun 5, 1970
Also published asCA959417A, CA959417A1, DE2111959A1, DE2111959B2
Publication numberUS 3823232 A, US 3823232A, US-A-3823232, US3823232 A, US3823232A
InventorsGalerne J
Original AssigneeGallia Sa Eugene
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Waving or uncurling hair with a composition containing an amino acid alkali metal carbonate
US 3823232 A
Abstract  available in
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Description  (OCR text may contain errors)

I I V m v 3,823,232 WAVING R UNCURLING HAIR WITH A COM 1 ,IZOSITION CONTAINING AN AMINO ACID METAL CARBONATE JeafiGalerii'e, Paris, France, assignor to Eugene-Gallia,

' f-SocieteAnonyme, Paris, France Nii DrawingfFiled Mar. 1, 1971, Ser. No. 119,921 Claims pr'i'ority,iapplicali0n France, June 5, 1970, 7020797; Nov. 2, 1970, 7039392 Int. ,Cl. A61k 7/10 "61 424-72' e Claims products.

3 BACKGROUND on THE INVENTION I It is now'conventional to utilize an aqueous solution of thioglycolic or thiolactic acid, or an ammonium salt 011:,analkali metal salt-of these acids, for permanently wavinguhuman hair. These aqueous solutions are generally referred to as cold permanent solutions. These solutions consist essentially of 3% to 8% of thioglycolic acid or thiolactic acid, mostly in the form of the am- .monium s'alt...or..the alkali metal salt (these proportions having giventhe best results and meeting maximum safety requirements), and an ammonia excess constituting an alkaline reserve. ThepH value of these solutions ranges vfrom about 8.5 to about according to the specific formula employed, and according as the ammonia is converted or notfln' addition to these products, which are essential-tor obtaining the desired effect, the solutions comprise additives adapted to improve the technical prop erties and the facility of use. These additives are sequesjftrant s, andmiscellaneous softeners, such as animal oils, vegetable oils,lanolidderivatives, perfumes, dyes, etc.

It is also known that these solutions can be employed 9 9 1! r r r a ha For waving hair, the hair impregnated with the product are 'kept curled'on cylindricalcurlers during the time necessary for: enabling'the product to perform its action, ,t his timebeing selected as a function of the desired defigree of curling' g 'i'riicontras't thereto, for the uncurling opj ration" the hair impregnated with'the product is drawn r tens'ioned by combing, or flattened by hand or by brush- 'g, and subs'equentlyfpress'ed on the head in this drawn ex h sds p t tr A V I More particularly, the uncurling method consists in impregnating thehair to be uncurled with solutions of which the force 'denotirfg number may be selected as a function of the specific characteristics of the hair to be States Patent (3 "ice 3,823,232 Patented July 9, 1974 However, very fluid solutions having a viscosity approaching that of water are not ideally suited for performing the uncurling operation, for they are generally unable, due to their insufficient viscosity, to keep the naturally curled hair in an extended or drawn condition, especially during the first period of the application time; the natural resiliency of very curled hair is sufiicient for reconstituting the natural waves, or the crimped appearance and condition in the case of African hair, in spite of the combining and smoothing steps. The smoothing step becomes gradually more detrimental to the hair as the application time proceeds, for as a consequence of the disorganization of its structure the tensile strength of the hair decreases considerably and thus the combing or smoothing operation may cause more or less important local breakages if care is not taken to avoid this operation when about one-half of the application time has elapsed.

To avoid this danger it is known to apply the reducing uncurling solution in the form of a cream having a consistency suflicient to withstand the resilient action of treated, and notably its degree of curling or waving. The 7 .hairissoakedwith the. solution, thencombedor flattened forfismogthed out so as to press the hair andremove the ztnaturalscurling therefrom.,The hair must be maintained in this pressed condition during the applicationtime.

-Whenthe hairdresserdeems that this time has elapsed,,

-employed -in a -permanentwavingoperatiom potassium salt or a lithium salt. a 1. H

natural curling which tends inherently to resume its initial shape. Therefore, relatively thick emulsions are used which have a cream consistency and contain to this end an emulsion base of a type known per se. It is obvious that the viscosity of these emulsions may range from the milk grade to a pasty one, the technological adaptation alone determining the choice of the viscosity and therefore the proper formulation. These emulsions or creams contain as a rule, like most permanent wave solutions. from 3% to 8% of thioglycolic or thiolactic acid, or of an ammonium salt or of an alkali metal salt of these acids.

Although these products, solutions, emulsions or creams for waving or uncurling hair give satisfactory and sufficient results from the technical standpoint, they are on the other hand unpleasant to handle, mainly on account of their offensive and suffocating smell. In fact, during the storage of these products, solutions, etc. very badsmelling mercaptans develop and the perfumes utilized for concealing the smell of these products are either destroyed or degraded, at least partially, by reduction and sulfuration, so that their odor is modified and frequently becomes nauseous.

During laboratory research work accomplished by the Applicant with a view to eliminate the inconveniences SUMMARY OF THE INVENTION To .avoid these serious inconveniences it is the essent1al object of the present invention to provide novel products for the permanent waving and uncurling of hair and keratinic fibres, which contain thioglycolic acid or thiolactic acid, or an ammonium salt or an'alkali metal salt of these acids, which are free of volatile ammonia, as an alkalizing agent.

In these novel products the excess ammonia is replaced essentially by the carbonate of an alkali metal salt of an aminoacid. The aniinoacid consists preferably of v. glycine or glycocoll (aminoacetic acid) but lysine methionine, tyrosine, glutamic acid, leucine, valine, alanine may also be used to this end.'These aminoacids may be, used in the racemic form or in the form of one of their optical isomers. The alkali metal salt may be a' sodium salt, a

This aminoacid alkali metal salt carbonate may be associated with an organic base such as morpholine, monoethanolamine, triethanolamine, etc.

The carbonate of the aminoacid alkali metal salt, such as sodium glycinate, is adapted to alkalize the curling or uncurling product without having the inconveniences of ammonia; in fact it is not volatile and eliminates the release of unpleasant and suffocating odors, does not attack or modify the perfumes added to said product and is less noxious to the users skin and to the skin of the person undergoing the treatment.

Other advantageous features characterizing the product of this invention is that it permits of accelerating, by heat effect, the curling or uncurling procedure and thus improves the curling or crimping treatment, without impairing the necessary alkalinity of the product implemented therefor; now it is known that ammonia is highly volatile when heated; therefore, the absence of ammonia eliminates the alteration effects consisting of a reddening of the natural or artificial color of the hair during the curling or uncurling operation, which effects are frequently observed when using conventional products.

Thus, a very substantial improvement is observed from the dual point of view of the operator and of the person receiving the treatment, and the results are also much improved; furthermore, it appears, from practical tests carried out with these products, that in the specific case of hair uncurling a greater safety is obtained against the risk of breaking the hair, as frequently observed with hitherto known processes whenever the treatment is carried out with a certain degree of clumsiness or with certain insufliciencies. Therefore, the results of the uncurling operation are as satisfactory as, and identical if not better than, those obtained with the hitherto applied technique, and the hair is not so ill-treated and emerges from the operation with definitely improved aesthetical properties.

The organic base possibly associated with the aminoacid alkali metal salt carbonate is advantageous in that it makes the hair considerably more pervious to the curling or uncurling product and permits, as a function of its proportion in the product, of graduating the strength thereof, i.e. the degree and rapidity of the curling and uncurling actions obtained with the product.

The proportion of aminoacid alkali metal salt carbonate in the product may advantageously range from about 2 to about 12% by weight, and the proportion of the possible organic base may range preferably from about 1% to about by weight.

The aminoacid alkali metal salt carbonate may be prepared extemporaneously, or even within the curling or uncurling product itself, and in either case without any isolation. This preparation consists in putting into mutual contact, in stoichiometric proportions, alkali metal carbonate and aminoacid, for example 1 mole of sodium carbonate and 2 moles of glycocoll or glycine or aminoacetic acid. From the economical point of view it is advantageous to perform this preparation extemporaneously in aqueous phase during the process of manufacturing the curling or uncurling product.

It will be noted that there is no inconvenience in preparing curling and uncurling products containing an excess either of alkali metal carbonate, or of aminoacid. Thus, the following proportions, for example of sodium carbonate and glycocoll, may be used:

Sodium carbonate Glycocoll 1 mole 1 mole 1 mole 2.5 moles 1 mole 3 moles 1.5 moles 1 mole -2 moles 1 mole *3 moles 1 mole The possible, excess of one of the components of the the range of percentages by weight given her inabove for said aminoacid alkali metal salt carbonate.

DESCRIPTION OF THE PREFERRED EMBODIMENTS Typical examples of formulae for preparing col P??? manent waving solutions (Examples 1 to 17) or uncufling emulsions or creams (Examples 18 to, 35)' according to this invention will now be given. In thesexamples the percentages are by weight. Moreover, these formulae may include an excess of alkali metal carbonate or aminoacid, although this excess is notmentionedr EXAMPLE 1 No 1 No. 2

Sodium glycinate carbonate, percent .E" "7. 4 3. 4 50% ammunium or sodium thioglycolate or thiolactate (50% aqueous solution), percent 16; 16 Sequestrant (disodium salt of EDTA), percent 0.3 0.3 Methyl p-hydroxybenzoate, percent; 0. 05 0.05 Proteol SN," percent 0. 2 v 0.2 Perfume, percent g.

Water (complement to make pH.

EXAMPLE 2 Sodium glycinate carbonate, percent r 4 3:4 Sodium or ammonium thioglycolate or thiolactate (50% aqueous solution), percent 16. 0 16.0 Sequestrant (disodium salt of EDTA), percent 0.3 Methyl p-hydroxybenzoate, percent 0 05 Proteol SN," percent Perfume, percent Morpholine, percent Opaquing agent, percent Water (complement to make 100%), p

The opaquing agent consists of synthetic latex giving a milky appearance to the solution for purely aesthetic reasons. i

EXAMPLE 3- No.'1 N0. 2

Sodium glycinate carbonate, percent 7. 4 3.4 Sodium or ammonium thioglycolate or thiolactate (50% aqueous solution), percent 16.0 16. 0 Sequestrant (disodium salt of EDTA), percen 0. 3 0. 3 Methyl p-hydroxybenzoate, percen 0. 05 0. 05 Proteol SN, percent 0. 2 0. 2 Perfume, percent I 0. 2 0. 2 Morpholme, percent 2.0 2.0 Opaqumg agent, percent. 0. 5 0.5 Lauryl pyrldlmum chloride, percent. 0. 2 0.2 9. 0'. 8. 9

Water (complement to make 100%), pH.

The function of lauryl pyridinium chlorideis toincreas'je the curling rate.

EXAMPLE 4 No.1 No.2, ,No,.3

Sodium glyclnate carbonate, percent- 7.4 3.4 5.0 Cetyltrnnethylammomum bromide, percent.-- 0. 2 0. 2 0. 2 Sodium or ammonium thioglycolate or thlo-' lactate (50% aqueous solution) percent 16.0 16.0 '10;0 Sequestrant (disodium salt of E TA), percent. O. 0.3 0. Methyl p-hydroxybenzoate, percent 5- 0:0 Morpholine, percent "Proteol SN," percent- Perfume, percent gvpaqumg agent, percent ater (complement to make 100%), pH

- l 7 Percent Ex. Ex. Ex. 27 2 8 29 Deminerallzed water, q.s.p 100 100 100 Cetyl alcohol self-emulsified with oxyethylenated B cetyl alcohol 22 22 Demlneralized water 30 30 30 Sodium glyoinate carbonate 5 5 Ammonium thioglycolate or thiolactate (50% aqueous solution) 6 Disodium salt of E.D.T.A 0 O. 3 0. 3 Sodium methyl p-hydroxybenzoate 0. 05 0. 05 Imidazoline O 0. 2 0. 2 Perfume I 0. 2 0. 2

Percent Ex. Ex. Ex. 30 31 32 Demineralized water, q .s.p 100 100 100 Cetyl alcohol self-emulsified with oxyethylenated cety] alcohol 22 22 B 22 Deminerallzed water 30 30 30 Sodium glycinate carbonate 7 7 7 Sodium thioglycolate or thiolactate 6 4 3 Disodium salt of E.D.T.A 0. 3 O. 3 0. 3 Sodium methyl p-hydroxybenzoate 0. 05 0. 05 0 05 Imidazoline O 0. 2 0. 2 0.2 Perfume 0. 2 0. 2 0, 2

Percent ;Ex. Ex. Ex. 33 34 35 Deminerallzed water, q.s.p- 100 100 100 Cetyl alcohol self-emulsified with oxyethylenated B cetyl alcohol 22 22 22 Demineralized water 30 30 30 Potassium tyrosinate carbonate- 4 Sodium methioninate carbonate- 4 Sodium lysinate carbonate- 4 Sodium carbonate 1. 5 1. 5 1. 5 Sodium thioglycolate or thiolactate 6 6 6 Disodium salt of E.D.T. 0.3 0. 3 0. 3 Sodium methyl p-hydroxybenzonte 0.05 0.05 0.05 Monoethanolamine- 2 2 2 Imidazoline O .2 0. 2 0. 2 0. 2 Perfume 0. 2 0. 2 0. 2

Of course, various changes may be brought in the details of the above-given formulae, notably in connection with the conventional additives, without inasmuch departing from the basic principle of the invention.

Whatisclaimedisr f v 1. A composition for permanently-curling, waving or uncurling hair and keratinic fibres, comprising 3% to 8% by weight of thioglycolic or thiolactic acid, or of an ammonium salt or an alkali metal salt of these acids, an aqueous carrier and an alkalizing agent, wherein said alkalizing agent consists of the carbonate of anaminogacid alkali metal salt, said aminoacid ,being selected from the group consisting of glycine, lysine, methionine, tyrosine, glutamic acid,,leucine, va'lineffand alanineQand said alkali metal being selected from the -gr0upconsistir'ig of sodium, potassium and lithium, the proportion of said aminoacid alkali metal salt carbonate is within the rang'e of about 2% to about 12% by weight, based on the' weight of the composition, and the pH of the composition is in the range of about 8.3 to about 9.3. a p p 2. A composition 'assetforth'in claim'l, which also contains an organic base selected from the group consisting of morpholine, monoethanolamine'add'triethanolamine, in a proportion within the range of about 1% to about 5% by weight, based on the weight of the composition.

3. A composition as set forthin claim 1, which additionally contains free alkali metal carbonate or free aminoacid.

4. A composition asset forth in claim 1, in the form of an aqueous solution;

5. A composition as set forth in claim 1, in the form of an emulsion. .7

References Cited STATES PATENTS UNITED K 7 2,464,281 3/1949 Pete son" 424-12 2,689,815 9/1954 Gershon et al.- 424-72 2,847,351 8/1958 Brown et 3.1. L 424 72'X 3,017,328 1/1962 Childrey et al 4241-71 3,242,052 3/1966 ShefIner 424 71 X FOREIGN PATENTS v i I I 210,071 7/1960 'Au'stri'a L. 4247 2 1,038,179 5/1953 France .2- 424 -71 1,072,866 3/1954 France 424-72 22,581 1/1962 East Germany 424-72 ALBERT T. MEYERS, P imary Ea in v. c. CLARKE, Assistant Examiner- US. 01. X11. 1T1;

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4010254 *Jul 7, 1975Mar 1, 1977Societe Anonyme Dite: L'orealGels based on vinyl ether-maleic anhydride copolymer neutralized by a basic amino acid
US4078055 *Mar 26, 1976Mar 7, 1978Kao Soap Co., Ltd.Deodorizing and smell-removing composition and method of using same
US4361157 *Oct 20, 1980Nov 30, 1982James Odie RMethod of curling negroid hair without rollers
US4459284 *Jun 9, 1981Jul 10, 1984Nikko Pharmaceutical Co., Ltd.Permanent waving composition comprising amino acids
US5271926 *Mar 19, 1992Dec 21, 1993Kao CorporationTwo-pack hair treatment composition and process for treating hair
US5690944 *Dec 20, 1994Nov 25, 1997Chesebrough-Pond's Usa Co., Division Of Conopco, Inc.Cosmetic compositions containing lactate dehydrogenase inhibitors
US5853742 *Jan 29, 1997Dec 29, 1998Chesebrough-Pond's Usa Co., Division Of ConopcoCosmetic compositions containing lactate dehydrogenase inhibitors
US6017519 *Feb 14, 1994Jan 25, 2000Goldwell AgComposition for permanent waving of human hair
EP0722715A1 *Nov 7, 1995Jul 24, 1996Unilever PlcCosmetic compositions containing lactate dehydrogenase inhibitors
U.S. Classification424/70.4, 424/70.5, 132/204, 8/127.51, 514/784
International ClassificationA61K, A61K31/195, A61K31/185, A45D7/00, A45D7/04, A61Q5/04, A61K8/46, A61K8/30, A61K8/44
Cooperative ClassificationA61Q5/04, A61K8/44, A61K8/46
European ClassificationA61K8/46, A61Q5/04, A61K8/44