AU601219B2 - Agent and process for permanent setting of hair - Google Patents

Abstract

Agent for permanent setting of hair based on a thioglycolic acid ester containing cysteamine or its salt, as well as a process for permanent setting of hair with said agent. The latter ensures efficient permanent setting which, at the same time, cares for the hair without curling the ends.

Description

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&UJ. A 7 8 7 3 2 8 7 )YLTIAN TI ,.tG EArIOEG tENTUM nPcrnTi.ii.0, Bno1j INTERNATIONALE~1 A IDG RiiNT 14JCH DEM VERTRAG OBER DIE INTERNATIONALE ZUSAMMENARBEIT AUF DEM GEI3IET DES PATENTWESENS (PCT) 1) Internationale Patent klassifikation 4 (11) Internationale Veroffcntlichungsnummer: WO 88/ 01860 A61 K 7/09 Al1 (43) Internationales Verorfentlichungsdatum: 24. M~irz 1988 (24.03.88) (21) Internationales Aktenzeicben: PCT/EP87/00457 (74) Gemeinsamer Vertreter: WE LLA A KTI EN GES ELL- SCI-AFT, Berliner Alice 65, D-6100 Darmstadt (22) Internationales Anmeldedatumn: (DE).

18. August 1987 (18.08.87) (81) Bestimmungsstaaten: AU, DK, US.

(31) Prioritatsakitenzeicheu: P 36 3199 (32) Prioritktatumn: 20. September 1986 (20.09.86) Veroifrentlicht Mit internarionalem Recherchenberich.

(33) Priorititsland DE (71) Anmelder (fur alle Bestimmungssmtaaen ausser US): WELLA AKTIENGESEL LSCHAFT (DE/DE]: Berli- A- 0. J. P. 12MY.18 ner Alice 65, D-6 100 Darmstadt 12MY18 (72) Erfinder;und Erfinder/Anmelder (nurfiir US), HARTMANN, Peter ASRLA (DE/DE]; Hoffmannstr. 6, D-6100 Darmstadt ASRLA KOHLER, Joachim [DE/DE]; Tm Trappengrund IA, 7AP 'p8 D-6107 Reinheim KONRAD, Euger [DE/DE];7A RT Mecklenburgerstr. 101. D-6100 Darmstadt (DE).

,PATENT OFFICE (54)Title: AGENT AND PROCESS FOR PERMANENT SETTING OF HAIR (54) Bezeichnung: MITTEL UND VERFARREN ZUR DAUERHAFTEN HAARVERFORMUNG (57) Abstract Agent for permanent setting of hair based on a thioglycolic acid ester containing cysteamine or its salt, as well as a process for permanent setting of hair with said agent. The latter ensures efficient permanent setting which, at the same time, care,i for the hair without curling the ends.

(57) Zusamnmenfassung Verformungs.nittel auf der Basis eines Thioglykolsa.ureesters mit einem Ge~ialt an Cysteamin oder dlessen Salz sowie emn Verfahren zur dauerhaften Verformung von Haaren unter Verwendun(, dieses Mittels. Das erfindungsgemage Mittel erm~glicht eine schonendle und zugleich wirkungsvolle Verformung der Haare ohne die Haarspitzen zu fiberkrausen.

SCO SMFTIC COMPOrnSTION AND PR(CFSS FOR THF PFRMANFNT SRAPING nF HAIR The present invention relates to an agent obtainable from several components and to a process for the permanent shaping of hair.

In order to avoid further damage to the hair weakly acid to neutral shaping agents are used for the shaping of intensely damaged, bleached or dyed hair. Over the past years it has been found that the thioglycolic esters are the reducing agents most suitable for this purpose.

However, the advantage of a hair-protecting shaping i0 treatment with weakly acid to neutral shaping agents is faced with a number of disadvantages. Thus, for example, as compared with mildly alkaline shaping agents based on thioglycolate these agents have a lower efficiency. For this reason in order to attain an adequate reshaping the supply of heat, an extension of the reaction time to 20-60 minutes and the use of relatively thin curlers are required. The use of these shaping agents for normal non-damaged natural hair does not seem to be practical because of the long reaction times of more than 30 minutes which also are required with the supply of heat so that heretofore the application of weakly acid to neutral shaping agents was usually restricted to predamaged, readily shapable hair.

Tests for increasing the effect of these preparations based on thioglycolic ester by adding specific mercapto ,u compounds, as for example, thioglycolic acid, thiolactic acid, thioglycerol and cysteine, did not result in the desired improvement but rather produced a deterioration of the waving result.

It has now been found that the effect of shaping agents based on the thioglycolic esters can be enhanced by the /A addition of cysteamine.

EP-OS 0 09o 916 discloses the use of cysteamine in 7 -2 strongly alkaline depilation agents based on specific mercapto compounds, as for example, thioglycolic acid, thiolactic acid or P -mercapto propionic acid, for increasing the effect.

Published Japanese Patent Application 57-62217 discloses that an addition of cysteamine to the conventional reducing agents used in hair shaping agents, as for example, thioglycolic acid, thioglycerol, thiolactic acid, sodium hyposulphite or sodium sulphite, particularly in the alkaline pH range, causes a -ynergistic increase in the waving efficiency.

However, the use of cysteamine to increase the shaping effect of acid or neutral shaping agents, particularly of those based on thioglycolic esters, has not been proposed. In the literature (see the above-mentioned published Japanese Patent Application 57-62217) it is explicitly emphasized that in order to attain a good waving effect, the shaping treatment should beicarried out under alkaline conditions.

Therefore, the present invention provides an agent for the permanent shaping of hair, based on a thioglycolic ester which contains cysteamine or its salt. While the thioglycolic ester, which preferably is the thioglycolic monoglyceric ester is contained in the shaping agent particularly in an amount of approximately 5 to 30 percent by weight (corresponding to a content of free thioglycolic acid of 2 to 16 percent by weight) the content of cysteamine or of its salt, especially cysteamine hydrochloride, preferably is 0.01 to 10 percent by weight.

The shaping agent according to the present invention preferably has a pH value of 4.5 to 7.5. It can be in the form of both an aqueous solution or an emulsion or even in a thickened form on an aqueous basis, particularly as a gel, cream or paste.

Of course, the shaping agent can contain all the S/r conventional additives for these agents, for example, kaolin, ~aa r. 1I111111l1 IIIII II I 3 bentonite, fatty acids, higher fat alcohols, starch, polyacrylic acids and its derivatives, cellulose derivatives,alginate, petrolat paraffin oil, wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric, nonionic surface-active substances, for example, fat alcohol sulphates, fat alcohol ether sulphates, alkyl sulphonates, alkyl benzene sulphates, quaternary ammonium salts, alkyl betaines, oxyethylated alkyl phenols, fatty acid alkanol amides or oxyethylated fatty esters as well as opacifiers, as for example, polyethylene glycol esters or alcohols, such as for example, ethanol, propanol, isopropanol or glycerol, dissolving intermediaries, stabilizers, buffer substances, perfume oils, dyes and hair-conditioning and hair-caring components, as for example, cationic polymers, lanolin derivatives, cholesterol, pantothnic acid or betain The above-mentioned components are used in the amounts conventionally used for these purposes, for example, the wetting agents and emulsifiers in concentrations of approximately 0.2 to 30 percent by weight while the thick eners can be contained in this agent in an amount of approximately 0.5 to 20 percent by weight.

Furthermore, in order to increase their effect socalled swelling auxiliaries and penetration substances, as for example, dipropylene glycol monomethyl ether, 2-pyrrolidone or imidazolidin-2-one, in an amount of approximately 2 to 30 percent can be added to this agent.

Since the thioglycolic esters are stable in an aqueous medium only for a short time (maximally 8 to 12 hours) and easily hydrolyze particularly in the alkaline range, it is required to package the thioglycolic ester in an anhydrous form and to produce the shaping agent prior to its application by mixing the thioglycolic ester-component with one or several further components.

S- 4 Depending on the packaging the agent according to the present invention can also be in the form of a two- or three-component preparation.

Thus, for example, the agent according to the present invention can be obtained by mixing two components, the first component containing the cysteamine or its salt and water di -i anhydrous component containing the thioglycolic ester.

In a further embodiment the agent according to the 1 0 present invention is produced by mixing an anhydrous component containing the thioglycolic ester and the cysteamine or its salt with water.

The agent according to the present invention can also be packaged in the form of a three-component preparation, one component containing the cysteamine or its salt, a second anhydrous component containing the thioglycolic ester and the third component containing the aqueous phase.

All the embodiments of the agent according to the present invention can contain the above-mentioned cosmetic additives in the aqueous component and also in the non-aqueous component(s). The non-aqueous components can be in the form of a liquid or in the solid form, for example, a powder.

Because of the synergistic effect of the combination of thioglycolic ester and cysteamine or its salt an acid to pH-neutral hair shaping agent based on thioglycolic e9ter is made available. Said hair-shaping agent is universally suitable for any hair structure, when required, with additional action of heat. The agent causes an elastic, uniform shaping from the hair line to the hair ends without ov-rfrizzing the pre-damaged hair ends, as frequently is the case when using the mildly alkaline preparations.

Furthermore, as compared with conventional shaping 5 agents based on thioglycolic ester the reaction times are substantially reduced by the agent according to the present invention so that a reshaping of hair that can only be shaped with difficulty is successful with the dpplication of heat (preferably at a temperature of 30 to 55 C) in approximately to 20 minutes. Likewise, the agent according to the invention based on a thioglycolic ester allows.the shaping of hair that can be easily waved, without the application of heat, in approximately 20 minutes. They also allow the use of larger curlers whose diameter corresponds to that of the curlers used for the shaping of hair with mildly alkaline agents.

Therefore, the present invention also provides a process for the permanent shaping of hair wherein prior to and/or after giving the hair the desired shape it is treated with a shaping agent, rinsed with water, when required, whereupon an oxidative aftertreatment is applied and the hair is rinsed with water. when required, the hair is then waterwaved and dried. The process according to the present invention is characterized in that the above-described shaping agent is used for the shaping treatment.

In an embodiment of the process according to the present invention, the hair is first washed with a shampoo and then rinsed with water, whereupon it is dried with a towel and divided into individual strands and rolled on curlers having a diameter of approximately 5 to 15 millimetres. The hair is then treated with an amount adequate for the shaping of the hair, preferably about 80 to 120 grams of the abovedescribed shaping agent according to the present invention.

In a further embodiment of the process according to the present invention, after washing the hair it is premoist- /7 i 4 ened with a portion of the above-described shaping agent according to the present invention, preferably about 40 to 6 grams, divided into individual strands and rolled on curlers.

The hair is then once more treated with the residual shaping agent, preferably about 40 to 60 grams.

After a reaction time adequate for the permanent shaping of the hair, which is approximately 5 to 30 minutes, depending on the condition of the hair, the pH value and the shaping efficiency of the shaping agent as well as on the application temperature, the hair is rinsed with water and subjected to oxidative aftertreatment it is "fixed").

Depending on the fullness of the hair, the aftertreatment agent is used in an amount of approximately 80 to 100 grams.

For the oxidative aftertreatment any aftertreatment agent used heretofore for this kind of treatment can be used.

Examples of oxidizing agents usable in these aftertreatment agents are potassium and sodium brormaae, sodium perborate, urea peroxide and hydrogen peroxide. The concentration of the oxidizing agent varies as a function of both the application time (usually about 5 to 15 minutes) and the application temperature. In the aqueous aftertreatment agents ready for use the oxidizing agent is normally present in a concentration of approximately 0.5 to 10 percent by weight. Of course, the agent for the oxidative aftertreatment can also contain other substances, as for example, wetting agents, weak acids, buffer substances and peroxide stabilizers, and can be in the form of an aqueous solution or an emulsion and in a thickened form on an aqueous basis, particularly as a cream, gel or paste.

The curlers are then removed. When required, the unrolled hair can be once more treated oxidatively, whereupon the hair is rinsed with water, when required, laid in water waves and rinally dried.

The present invention will be further illustrated by way of the following Examples.

a i-rrt^-l«^fim-i1Bl-h^ll^tf^ 7 Example 1 Component 1: 0.20 g of cysteamine 0.30 g of perfume oil 99.50 g of water, completely desalted 100.00 g Component 2: 60.00 g of thioglycolic monoglyceric ester 40.00 g of glycerol 100.00 g Prior to the use of the hair shaping agent 80 g of C0 the component 1 and 40 g of the component 2 are mixed with each other. The pH value of this hair shaping agent is Slightly predamaged hair is washed with a shampoo, rubbed with a towel and rolled on curlers having 3 diameter of 8 millimetres. The above-described hair shaping agent is then uniformly distributed over the rolled-up hair. The hair is then covered with a plastic cap and heated for 15 minutes under a hair drier at a temperature of 40 0 C. The cap is then removed, the hair is rinsed with water and subjected to an oxidative aftertreatment with 100 gram of a 3% aqueous hydrogen peroxide solution. After removing the curlers the hair is once more rinsed with water, laid in water waves and then dried.

The result of this treatment is a uniform naturally appearing reshaping of the hair from the hair line to the hair ends.

Example 2 Component 1: 1.00 g of cysteamine 1.00 g of cysteamine hydrochloride 0.30 g of perfume oil '97.70 g of water, completely desalted 100.00 g i .Component 2: 60.00 g of thioglycolic monoglyceric ester \t /Qk 8 40.00 g of glycerol 100.00 g Prior to its use 60 grams of the component 1 and grams of the component 2 are mixed so as to forr.i a hair shaping agent having a pH value of 6.6.

Hair that can be easily shaped is washed with a shampoo and thoroughly rinsed with water, whereupon approximately one half of the hair shaping agent is uniformly distributed over the hair has been rubbed with a towel. The hair is rolled on curlers having a diameter of 10 millimetres and is once more moistened with the residual hair shaping agent. After a reaction time of 20 minutes the hair is rinsed with water and subjected to an oxidative aftertreatment with 100 grams of a 2 percent hydrogen peroxide solution. After removing the curlers the hair is again rinsed with water and then dried.

Example 3 Component 1: 10.00 g of cystoamine hydrochloride Component 2: ponent 2 are for use, its 1.50 g of ammonia, 25 percent aqueous solution 0.30 g of perfume oil 88.20 g of water, completely desalted 100.00 g 60.00 g of thioglycolic monoglyceric ester 40.00 g of glycerol 100.00 g grams of tne component 1 and 40 grams of the commixed so as to form a hair shaping agent ready pH is Normal, not predamaged hair, which thus can be shaped only'with difficulty, is washed, rubbed with a towel S and rolled on curlers having a diameter of 6 millimetres, whereupon the hair is uniformly moistened with the hair shap- 1 i l* arrer" ~~-O~LIIBglYW1* ~-sCspl I~LPI~C-~C~ iv -9ing agent described above. After a reaction time of 20 minutes the hair is thoroughly rinsed with water and then subjected to an oxidative aftertreatment with 80 grams of a 3 percent hydrogen peroxide solution. After the removal of the curlers the hair is once more rinsed with water, laid in water waves and then dried.

The hair thus shaped has a uniform permanent wave which is comparable to that attained by treatment with mildly alkaline permanent shaping agent.

Example 4 Component 1: 10.0 g of cysteamine hydrochloride Component 2: 1.50 g of ammonia, 25 percent aqueous solution 0.30 g of perfume oil 88.20 g of water, completely desalted Component 1+2: 100.00 g Component 3: 60.00 g of thioglycolic monoglyceric ester 40.00 g of glycerol 100.00 g The component 1 is dissolved in component 2, whereupon 80 grams of this solution are mixed with 40 grams of component 3. The pH value of tne hair shaping agent ready for use is After washing normal, not predamaged hair, it is premoistened with on'e half of the above-described hair shaping agent and rolled on curlers having a diameter of 8 millimetres. The hair is then once more treated with the residual shaping agent and subjected to heat treatment with a heat radiation for 15 minutes. The hair is subsequently rinsed with water and subjected to an oxidative aftertreatment with 100 grams of a 3 percent aqueous hydrogen peroxide solution.

After removing the curlers the hair is once more rinsed with water and dried.

.4e~ 10 A commercial thioglycolic glyceric ester was used as thioglycolic monoglyceric ester. The pH value of a 20 percent aqueous solution of this thioglycolicglyceric ester is approximately 2 to 3.

All percentage data in the present application related to percent by weight.

*01 \N

Claims (11)

1. An agent for the permanent shaping of hair, comprising a thiogylcolic ester and cysteamine or cysteamine salts.

2. An agent according to claim 1, which contains 0.01 to percent by weight of cysteamine or its salts.

3. An agent according to claim 1 or 2 in which the cysteamine salt is the cysteamine hydrochloride.

4. An agent according to any one of claims 1 to 3 in which the thioglycolic ester is contained in an amount of 5 to 30 percent by weight.

5. An agent according to any one of claims 1 to 4 in o* °which the thioglycolic ester is the thioglycolic monoglyceric ester.

6. An agent according to any one of claims 1 to 5 in which the pH value is from 4.5 to

7. A package comprising two separate components, a first S component containing an aqueous solution of cysteamine or its salts and a second component containing thioglycolic ester such that when the components are mixed, an agent in S. accordance with any one of claims 1 to 6 is produced.

8. A package comprising two separate components, a first component containing cysteamine or its salts and thioglycolic ester and a second component containing water S.....such that when the components are mixed, an agent in accordance with any one of claims 1 to 6 is produced.

9. A package comprising three separate components, a first component containing cysteamine or its salts, a second component containing thioglycolic ester and a third component containing an aqueous phase such that when the components are mixed, an agent in accor ice with any one of claims 1 to 6 is produced. 12 A process for the permanent shaping of hair, wherein prior to and/or after the hair is given the desired shape it is treated with a shaping agent, rinsed with water, then subjected to oxidative aftertreatment, rinsed with water, when required, laid in water waves and then dried, the shaping agent being according to any one of claims 1 to 6.

11. A process according to claim 10, in which the shaping agent is allowed to react for 5 to 30 minutes. j 12. A process according te claim 10, in which the shaping agent is allowed to react for 15 to 20 minutes while applying heat.

13. A process according to any one of claims 10 to 12 in which the shaping agent is used in an amount of 80 to 120 grams. DATED this 18th day of June 1990. e WELLA AKTIENGESELLSCHAFT Patent Attorneys for the Applicant: F.B. RICE CO. I 'I 13 ABSTRACT OF THE DISCLOSURE The present invention relates to a shaping agent, based on a thioglycolic ester containing cysteamine or its salt, and to a process for the permanent shaping of hair with the use of this agent. The agent according to the present invention allows a gentle and at the same time effective shap- ing of the hair without overfrizzing the hair ends. I t r a i ii r I .iil ii' I- I 1 1 INTERNATIONAL SEARCH REPORT International Application NoPCT/EP 87/00457 Y-I-I-- I. CLASSIFICATION OF SUBJECT MATTER (if several classificalion ymbols aDply. Indicate all) According to International Patent Classification (IPC) or to both National Classification and IPC Int.Cl 4 A 61 K 7/09 II. FIELDS SEARCHED Minimum Documentation Searched 7 Classificatlon System Classification Symbols Int.ll 4 A 61 K 7/00 Documentation Searched other than Minimum Documentation to the Extent that auch Documents are Included In the Fields Searched I IIl. DOCUMENTS CONSIDERED TO IE RELEVANT Category Citation of Document, with ndication, where approprlate, of the relevant passages is Relevant to Claim No A FR, A, 1367854 (SHERICO) 15 June 1964, see the abstract; page 2, left hand 1-3,6 column, lines 9-21; page 3,"Composition B" SSpecial categories of cited documents o1 later document published after the Internationa filing date document definin the general state of the art which II not or priority date and not in conlict with the appDDcatbon bu! considered to be of particular relevance cited to understand the principle or theory underlying the invention earlier document but published on or after the international document arcula eevance the claimed invent filing date document of particular relevance, the claimed inventon cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or Involve an inventive step which is cited to establih the publication date of another document particular relevance the caimed inveno citation or other special reason (t ebacified) Y" document of particular relevance, th. claimed Inventno" n o o r s ron a ifie cannot be considered to Involve an inventive step when the document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person akilled document published prior to the international filing date but in the art later than the priority date claimed document member of the aum patent family IV. CERTIFICATION Date of the Actual Completion of the International Search Date of Mailing of this International Search Report November 1987 (30.11.87) 08 January 1988 (08.01.88) International Searching Authority Signature of Authorized Officer EUROPEAN PATENT OFFICE Form PCT/ISA/210 (second sheet) (January 1985) ANNEX TO THE INTERNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION NO. EP 8700457 SA 18 43')9 This annex lists the patent family members relating to thc patent documents cited in the aho~e-mentioned international search report. The members are as contained in the European Patent Office EDP rile on 09/12/87 The European Patent Office is in no way liable for these particulars Aihich are merely given for the purpose of information. Patent document Publication Patent family Puhl Icat(ion cited in search rcport date membcr(s) date FR-A- 1367854 Keine M For more details about this annex see Official Journal of the European Patent Office, No. 12/82