AU711091B2

AU711091B2 - Keratin fibre modifying compositions

Info

Publication number: AU711091B2
Application number: AU25620/97A
Authority: AU
Inventors: Max Feughelman; Barry Keith Willis
Original assignee: R&C Products Pty Ltd
Current assignee: Procter and Gamble Deutschland GmbH
Priority date: 1996-04-27
Filing date: 1997-04-24
Publication date: 1999-10-07
Anticipated expiration: 2017-04-24
Also published as: GB2312444A; ZA973530B; GB9608802D0; WO1997040810A1; AU2562097A

Description

WO 97/40810 PCT/AU97/00247 Keratin Fibre Modifying Compositions Technical Field This invention relates to modification of keratin fibres, particularly permanently altering the configuration of hair such as permanent waving.

Background Art The stability of keratin fibres is due to disulfide bonds and hydrogen bonds between neighbouring polypeptide chains. Keratin fibres such as hair are softened by wetting with water as water enters the hydrogen bonds of the hair. Temporary reshaping of hair can be obtained by deformation of wet hair. After drying, the new shape will be held until the hair contacts moisture whereupon it will soften again.

Permanent reshaping of hair can be obtained using a reductooxidative process whereby the disulfide bonds of the hair are broken using a reducing agent; the hair is set into the desired configuration such as straight or wavy; the hair is then rinsed to remove the reducing agent followed by oxidisation using an oxidising agent such as hydrogen peroxide or a bromate salt to reform disulfide bonds and harden the hair into the new imposed shape.

By "reducto-oxidative process" is meant treating the keratin fibre first with a reducing agent, removing said reducing agent and then treating the keratin fibre with an oxidative agent.

Typical reducing agents include sulphites and mercaptans (thiols) such as thioglycolic acid salts, eg ammonium thioglycolate, and thioglycolic acid esters, eg glycerol thioglycolate. Other thiol containing reagents such as thiolactic acid, beta-mercapto propionic acid, beta-mercapto butyric acid, mercapto succinic acid and the like are also effective.

The effectiveness of the reduction/oxidation process in permanently altering the configuration of hair depends on many factors including the condition of the hair, the nature of the reducing agent and the skill of the operator in setting the hair into the desired configuration and applying the reducing/oxidising agents. A disadvantage of the reduction/oxidation process is a loss of mechanical properties of the hair such as reduced tensile strength and elasticity and increased porosity. Various additives for the reducing agent have been proposed to reduce the loss of mechanical properties and improve the end result of the process.

WO 97/40810 PCT/AU97/00247 2 Disclosure of the Invention It has now been found that the effectiveness of the reducing agent in relation to subsequent curl retention after a permanent waving process can be enhanced by applying a quaternary ammonium compound having at least one C12- 22 carbon chain substituent to the hair simultaneously with the reducing agent or subsequent to application of the reducing agent but before application of the oxidising agent.

The invention is equally applicable to permanent straightening of hair and subsequent retention of the straightened configuration and to modifying the configuration of keratin fibres in general. The term "keratin fibres" includes human hair, wool and animal hair and bristles.

In a first aspect, the present invention provides a method for modifying a keratin fibre comprising: applying a reducing agent to the keratin fibre and setting the fibre into a desired configuration; simultaneously or subsequently applying an aqueous solution comprising at least 1% w/w, preferably 1 to 20% w/w of one or more nonpolymeric quaternary ammonium compounds having one C 12 22 carbon chain substituent and three C 1 6 alkyl substituents each being the same or different; rinsing the keratin fibre to substantially remove the reducing agent; and applying an oxidising agent to the keratin fibre.

Preferably, the keratin fibre is then rinsed with water.

In a second aspect, the present invention provides a method for the permanent waving or straightening of hair comprising: applying a reducing agent to the hair and setting the hair into a desired configuration; simultaneously or subsequently applying an aqueous solution comprising at least preferably 1 to 20% w/w of one or more non polymeric quaternary ammonium compounds having one C 12 22 carbon chain substituent and three C 1 6 alkyl substituents each being the same or different; rinsing the hair to substantially remove the reducing agent; and applying an oxidising agent to the hair.

The hair may then be rinsed with water.

WO 97/40810 PCT/AU97/00247 3 In a third aspect, the present invention provides the use of one or more substantially water-soluble non-polymeric quaternary ammonium compounds having one C1- 22 carbon chain substituent and three C 1 -6 alkyl substituents each being the same or different in a reducto-oxidative process for permanent waving or straightening of hair.

In a fourth aspect, the present invention provides a composition for use in the permanent waving or straightening of hair comprising 1 to w/w of one or more substantially water-soluble non-polymeric quaternary ammonium compounds having one C 12 22 carbon chain substituent and three

C

1 _6 alkyl substituents each being the same or different, and a reducing agent.

As used herein, the term "quaternary ammonium compound" means a non-polymeric ammonium compound in which all four hydrogen atoms are substituted by radicals.

The quaternary ammonium compounds of the present invention have one C 1 2 2 2 carbon chain substituent. The C12- 22 carbon chain may be straight or branched. Preferably, the carbon chain is of 14 to 18 carbon atoms, more preferably 14 to 16 carbon atoms. Other substituents are preferably the same or different and are lower alkyl groups of 1 to 6 carbon atoms, more preferably methyl groups.

The substituents of the quaternary ammonium compound are selected so that the quaternary ammonium compound is substantially water soluble and may form a 1 to 20% w/w aqueous solution. Examples of suitable quaternary ammonium compounds are cetyl trimethyl ammonium salts including halides, sulphates (such as methosulphate salt), saccharinate and tosylate. Cetyl trimethyl ammonium bromide (CTAB) is most preferred.

The quaternary ammonium compounds may be used with conventional reducing agents. Preferred reducing agents are monoethanolamine and ammonium thioglycolate. Preferably, the reducing agent is in the form of an aqueous composition comprising 1-12% w/w, preferably 5-10% w/w, of reducing agent, having a pH of 5 to 10, more preferably 9-9.5.

The quaternary ammonium compounds may be included in the composition comprising the reducing agent or applied to the hair subsequent to application of the reducing agent. Where the quaternary ammonium compounds are included in the composition comprising the reducing agent, WO 97/40810 PCT/AU97/00247 4 other conventional ingredients may also be included such as surfactants, perfumes, preservatives (if necessary) and colorants.

Conventional nonionic surfactants may be included, such as ethoxylated alcohols.

Preservatives may not be necessary at high pH; however if preservatives are included, the preservatives may be selected from sodium hydroxymethyl glycinate (SUTTOCIDE A

TM

Sutton), 7-ethylbicyclooxazolidine (OXABAN-E T M Angus), methylparaben and diazolidinyl urea (GERMALL IIT, Sutton).

Perfumes and colorants may be selected by the person skilled in the art to provide the desired organoleptic properties to satisfy the end user.

Modes for Carrying Out the Invention The following examples further illustrate the present invention.

Example 1 The permanency of wave of human hair treated with a composition of the present invention (composition 1) was compared with the permanency of wave of human hair treated with a commercially available permanent waving solution (control) by measuring the curl retention after immersing in boiling water.

The control composition was a commercially available permanent waving solution including ammonium thioglycolate, 1.2% w/v ammonia, trideceth-12, fragrance and water.

Composition 1: Ingredient w/w Ammonium thioglycolate solution 14 Ammonia solution 3.6 CTAB solution Water 77.4 Ingredients and availability Ammonium thioglycolate solution: ammonium thioglycolate solution about 59% as audited (AJAX); Ammonia solution: ammonia 28% solution (AJAX); CTAB solution: cetyl trimethyl ammonium bromide solution

I

WO 97/40810 PCT/AU97/00247 Human hair samples were wound on a stainless steel rod of diameter of about 1.6mm for 20 revolutions (100 counts), immersed in the waving solution for 20 minutes then immersed in an oxidising (neutralising) solution for 1 minute. The samples were removed from the roller and immersed in boiling water for 1 minute. At the end of one minute the samples were withdrawn and the number of counts were recorded. The samples were then immersed in boiling water for 5 minutes and withdrawn and the number of counts recorded. The results are set out in Table 1.

TABLE 1 Control Original 20 counts 1 min 5 min Composition 1 CTAB solution Original 20 counts 1 min R min 12 6 18 2 20 13 13 4 18 11 12 3 19 12 16 3 20 12 11 7 15 8 Curl retention

I

S65.9% 20.8% 91.7% 59.2% 91.7% 159.2% As can be seen from Table 1, Composition 1 containing 5% CTAB solution retains curl significantly better than the control composition.

WO 97/40810 PCT/AU97/00247 6 Example 2 The process of Example 1 was repeated using the same control composition and Composition 1 as well as a second composition of the present invention (Composition 2 ingredients and availability as for Composition 1).

Composition 2 Ingredient Ammonium thioglycolate solution Ammonia solution CTAB solution Water w/w 14 3.6 10.0 72.4 72.4 The results are set out below in Table 2.

TABLE 2 Compositi Original- 1 Total 1 Average 1 Curl retention ion 1 solution 20 counts min 5 min i, Composition 2 Control

I

10% CTAB solution i Orijainal- 20 counts -4 Oi al2igil. ?n ,uin 1 min 5 min 1 min 5 min 16 12 20 14 14 3 18 18 20 12 10 7 18 10 12 6 12 12 17 7 14 2 11 3 9 18 12 14 8 14 12 11 13 11 L04 70 96 57 74 44 7.3 11.7 16 9.5 12.3 7.3 86.5 58.5 80 47.5 61.5 36.5 As shown in Table 2, the 5% CTAB solution gives greater curl retention than the 10% CTAB solution and both are significantly better than the control composition.

WO 97/40810 PCT/AU97/00247 7 CTAB in compositions 1 and 2 may be replaced by other cetyl trimethyl ammonium salts such as cetrimonium chloride, cetrimonium methosulphate, cetrimonium saccharinate or cetrimonium tosylate.

Example 3 The uptake of CTAB solutions by human hair at 35 0 C was measured.

Dry human hair samples were weighed then immersed in compositions 1 and 2 of examples 1 and 2 and compositions 3 and 4 as shown below. The immersion time was 20 minutes. The hair samples were then removed, dried and reweighed. The weight differences found are shown in Tables 3 and 4 as set out. Theses weight differences are indicative of the uptake of the compositions.

TABLE 3 INITIAL FINAL WEIGHT DIFF SOLUTION WEIGHT WEIGHT 1.10128 1.0875 7.38 Composition 1 at (no surfactant) 0.9482 1.0257 8.17 Composition 2 at 35 0

C

(no surfactant) TABLE 4 INITIAL FINAL WEIGHT DIFF SOLUTION WEIGHT WEIGHT 0.919 0.9645 4.95 Composition 3 at 35 0

C

0.9651 1.0242 6.12 Composition 4 at WO 97/40810 PCT/AU97/00247 Composition 3 Ingredient w/w Ammonium thioglycolate solution 14 Ammonia solution 3.6 CTAB solution Renex 30 0.6 Water 76.8 Composition 4 Ingredient w/w Ammonium thioglycolate solution 14 Ammonia solution 3.6 CTAB solution 10.0 Renex 30 0.6 Water 71.8 Ingredients and availability Ammonium thioglycolate solution, ammonia solution, CTAB solution as for example 1.

Renex 30: Polyoxy Ethylene (12) Tridecylether (ICI).

Comparing Tables 3 and 4, it can be seen that uptake of CTAB solutions is lower in the presence of surfactant but nevertheless, the solution is taken up by the hair samples.

It is theorised that the improved effectiveness of the present invention comes about through uptake of the quaternary ammonium compound into the reduced hair thereby improving the stability of the altered configuration (curly or straightened) after oxidation.

It will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention as shown in the specific embodiments without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.

Claims

1. A method for modifying the configuration of a keratin fibre comprising: applying a reducing agent having a pH in the range 8.5 to 10 to the keratin fibre and setting the fibre into a desired configuration; simultaneously or subsequently applying an aqueous solution consisting of at least 1% w/w, preferably 1 to 20% w/w of one or more non- polymeric quaternary ammonium compounds having one C2- 22 carbon chain substituent and three C 1 alkyl substituents each being the same or different; 0 rinsing the keratin fibre to substantially remove the reducing agent; *000 o• S 0@00 0O* 0 0 •go• 0 0 0 00* •go• o• o• 1 and 00 0 0 0 0..0 00 0S 0 00 0 S0 0 00 0 0 applying an oxidising agent to the keratin fibre.

2. A method for permanent waving or straightening of hair comprising: applying a reducing agent having a pH in the range 8.5 to 10 to the 15 hair and setting the hair into a desired configuration; simultaneously or subsequently applying an aqueous solution consisting of at least preferably 1 to 20% w/w of one or more non polymeric quaternary ammonium compounds having one C2, 22 carbon chain substituent and three C 6 alkyl substituents each being the same or different; 20 rinsing the hair to substantially remove the reducing agent; and applying an oxidising agent to the hair.

3. A method according to claim 1 or 2, wherein the or each quaternary ammonium compound has one C 1 18 preferably C 14 _a carbon chain substituent.

4. A method according to claim 3, wherein the or each quaternary ammonium compound has substituents selected from the group consisting of C, 14 .1 carbon chain and C 1 alkyl.

A method according to claim 5, wherein the quaternary ammonium compound is cetyl trimethyl ammonium bromide.

6. A method according to any of claims 1 to 5, wherein an aqueous solution consisting of 1-10% w/w of one or more quaternary ammonium compounds is applied.

7. A method according to claim 1 or 2, wherein an aqueous solution consisting of by weight 1 to 20 of cetyl trimethyl ammonium bromide, and 1 to 12% of ammnonium thioglycolate is applied, said composition having a pH in the range of 8.5 to

8. A method according to claim 7, wherein an aqueous solution consisting of by weight 1 to 5 of cetyl trimethyl ammonium bromide, and to 10% of ammonium thioglycolate is applied, said composition having a pH in the range of 8.5 to

9. The use of one or more substantially water-soluble non-polymeric 10 quaternary ammonium compounds having one C 1 2- 22 carbon chain substituent and three CG, alkyl substituents each being the same or different in conjunction with a reducing agent having a pH in the range of 8.5 to 10 in a reducto-oxidative process for permanent waving or straightening of hair.

10. The use according to claim 9, wherein the or each quaternary 15 ammonium compound is used in a concentration of at least 1% w/w.

11. The use according to claim 10, wherein the or each quaternary ammonium compound is used in a concentration of 1-20 w/w.

12. The use according to any one of claims 9 to 11, wherein the or each quaternary ammonium compound has one C 14 -1 carbon chain substituent. 20

13. The use according to claim 12 wherein the or each quaternary ammonium compound has one C 14 carbon chain substituent.

14. The use according to any one of claims 10 to 13, wherein the or each quaternary ammonium compound has substituents selected from the group consisting of C1 4 1 6 carbon chain and C 1 alkyl. 25

15. The use according to claim 14, wherein the quaternary ammonium compound is cetyl trimethyl ammonium bromide.

16. The use of a composition for improving retention of altered configuration of hair in a process for permanent waving or straightening of hair, said composition consisting of 1 to 20 w/w of cetyl trimethyl ammonium bromide, and 1 to 12% w/w of ammonium thioglycolate, said composition having a pH in the range of 8.5 to

17. The use according to claim 16, said composition consisting of 1 to w/w of cetyl trimethyl ammonium bromide, and 5 to 10% w/w of ammonium thioglycolate, said composition having a pH in the range of to

18. The use according to claim 17, said composition consisting of 1 to 5 w/w of cetyl trimethyl ammonium bromide, and 5 to 10% w/w of ammonium thioglycolate, said composition having a pH in the range of to

19. A composition for use in the permanent waving or straightening of hair comprising 1 to 20% w/w of one or more substantially water-soluble non-polymeric quaternary ammonium compounds having one C 12 -2 2 carbon chain substituent and three C 1 alkyl substituents each being the same or different, and a reducing agent having a pH in the range of 8.5 to se* 10

20. A composition according to claim 19 wherein the or each quaternary ammonium compound has one C 14 1 8 carbon chain substituent.

21. A composition according to claim 19 wherein the or each quaternary ammonium compound has one C 14 _1 carbon chain substituent.

22. A composition according to claim 20 or claim 21 wherein the 15 composition consists of 1 to 20% w/w of cetyl trimethyl ammonium bromide, and 1-12% w/w of ammonium thioglycolate, said composition having a pH in the range of 8.5 to

23. A composition according to claim 22 wherein the composition consists of 1 to 10% w/w of cetyl trimethyl ammonium bromide, and 5-10% 20 w/w of ammonium thioglycolate, said composition having a pH in the range of 8.5 to

24. A composition according to claim 23 wherein the composition consists of 1 to 5% w/w of cetyl trimethyl ammonium bromide, and 5-10% w/w of ammonium thioglycolate, said composition having a pH in the range 25 of 8.5 to

25. A composition as hereinbefore defined with reference to any one of the examples.

26. A method for modifying the configuration of a keratin fibre as hereinbefore defined with reference to any one of the examples. Dated this 19th day of November 1998 Patent Attorneys for the Applicant: F B RICE CO