PROCESS FOR TREATING KERATIN FIBRES WITH AN ETHYLENIC POLYMER BEARING A MALEIC ANHYDRIDE GROUP AND A POLYOL

Abstract

Process for treating keratin fibres with an ethylenicpolymer bearing a maleic anhydride group and a polyol The invention relates to a cosmetic process for treating keratin fibres, comprising the application to the keratin fibres of a mixture of a maleic anhydride ethylenic polymer, a liposoluble polyol and an amine catalyst; said maleic anhydride ethylenic polymer being obtained by polymerization of: (a) 25% to 95% by weight, relative to the total weight of monomers, of an ethylenic monomer bearing an at least C8 linear or branched alkyl group; (b) 5% to 25% by weight of maleic anhydride; (c) 0% to 50% by weight of additional (meth)acrylate monomer; and a step of heating the keratin fibres to a temperature ranging from 90 C. to 250 C. The invention also relates to the crosslinked polymer obtained by reacting said ethylenic polymer with said liposoluble polyol. The treated keratin fibres have good water-resistant fixing properties.

Claims

1. A cosmetic process for treating keratin fibres, comprising: (i) a step of applying to keratin fibres an extemporaneous mixture of a maleic anhydride ethylenic polymer, or of a cosmetic composition comprising it, of a liposoluble polyol compound or of a cosmetic composition containing it, and of an amine catalyst; said maleic anhydride ethylenic polymer being derived from the polymerization of: (a) 45% to 95% by weight, relative to the total weight of monomers, of an ethylenic monomer bearing an at least C8 linear or branched alkyl group; (b) 5% to 25% by weight of maleic anhydride; (c) 0% to 50% by weight of additional monomer chosen from: (i) polydimethylsiloxane silicone monomers bearing a mono(meth)acryloyloxy end group of formula (I) below: ##STR00007## in which: R8 denotes a hydrogen atom or a methyl group; R9 denotes a linear or branched divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bonds O; R10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms and especially from 2 to 8 carbon atoms; n denotes an integer ranging from 1 to 300; (ii) linear or branched C1-C6 alkyl (meth)acrylate or C6-C12 cycloalkyl (meth)acrylate non-silicone monomers; (ii) a step of heating the keratin fibres to a temperature ranging from 90 C. to 250 C.; steps (i) and (ii) being performed at the same time or separately, in the order (i) and then (ii).

2. The process according to claim 1, wherein the ethylenic monomer bearing an at least C8 linear or branched alkyl group is chosen from: a) linear or branched C8-C22 alkyl (meth)acrylates; b) the (meth)acrylamides of formula CH2=C(R1)-CONR3R4 in which R1 represents a hydrogen atom or a methyl radical, R3 represents a hydrogen atom or a linear or branched C1-C12 alkyl group, and R4 represents a linear or branched C8 to C12 alkyl group; c) the vinyl esters of formula R5-COOCHCH2 in which R5 represents a linear or branched C8-C22 alkyl group; d) the ethers of formula R6-OCHCH2 in which R6 represents a linear or branched C8-C22 alkyl group.

3. The process according to claim 1, wherein the ethylenic monomer bearing an at least C8 linear or branched alkyl group is chosen from C8-C22.

4. The process according to claim 1, wherein the ethylenic monomer bearing an at least C8 linear or branched alkyl group is chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, lauryl acrylate, lauryl methacrylate, behenyl acrylate, behenyl methacrylate, stearyl acrylate, stearyl methacrylate.

5. The process according to claim 1, wherein the ethylenic monomer bearing an at least C8 linear or branched alkyl group is present in said ethylenic polymer in a content ranging from 50% to 90% by weight, relative to the total weight of monomers.

6. The process according to claim 1, wherein maleic anhydride is present in said ethylenic polymer in a content ranging from 10% to 25% by weight relative to the total weight of monomers.

7. The process according to claim 1, wherein, for said silicone monomer of formula (I): R8 denotes a methyl group; R9 denotes a linear divalent hydrocarbon-based group containing from 2 to 4 carbon atoms; R10 represents a linear or branched alkyl group, comprising from 2 to 8 carbon atoms; n denotes an integer ranging from 3 to 200.

8. The process according to claim 1, wherein said additional monomer is non-silicone and is chosen from C6-C12 cycloalkyl (meth)acrylates.

9. The process according to claim 1, wherein said ethylenic polymer comprises said additional silicone monomer of formula (I).

10. The process according to claim 1, wherein said ethylenic polymer comprises an additional monomer present in a content ranging from 5% to 50% by weight, relative to the total weight of monomers.

11. The process according to claim 1, wherein said ethylenic polymer does not contain any additional monomer.

12. The process according to claim 1, wherein said ethylenic polymer comprises, or consists of: (a) 75% to 95% by weight, relative to the total weight of monomers, of linear or branched C8-C22 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride.

13. The process according to claim 1, wherein said ethylenic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/maleic anhydride stearyl acrylate/maleic anhydride 2-ethylhexyl acrylate/stearyl acrylate/maleic anhydride.

14. The process according to claim 1, wherein said ethylenic polymer comprises, or consists of: (a) 45% to 94.5% by weight, relative to the total weight of monomers, of linear or branched C8-C22 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; (c) 0.5% to 50% by weight of silicone monomer (I).

15. The process according to claim 1, wherein said ethylenic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/maleic anhydride/silicone monomer (I) stearyl acrylate/maleic anhydride/silicone monomer (I) 2-ethylhexyl acrylate/stearyl acrylate/maleic anhydride/silicone monomer (I).

16. The process according to claim 1, wherein said ethylenic polymer comprises, or consists of: (a) 45% to 94.5% by weight, relative to the total weight of monomers, of linear or branched C8-C18 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; (c) 0.5% to 50% by weight of C6-C12 cycloalkyl (meth)acrylate.

17. The process according to claim 1, wherein said ethylenic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/maleic anhydride/isobornyl (meth)acrylate stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate 2-ethylhexyl acrylate/stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate.

18. The process according to claim 1, wherein said ethylenic polymer comprises, or consists of: (a) 45% to 94.5% by weight, relative to the total weight of monomers, of linear or branched C8-C18 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; (c) 0.5% to 50% by weight of a mixture of C6-C12 cycloalkyl (meth)acrylate and of silicone monomer (I).

19. The process according to claim 1, wherein said ethylenic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/maleic anhydride/isobornyl (meth)acrylate/silicone monomer (I) stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate/silicone monomer (I) 2-ethylhexyl acrylate/stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate/silicone monomer (I).

20. The process according to claim 1, wherein the ethylenic polymer has a weight-average molecular weight ranging from 5000 to 1 000 000 g/mol.

21. The process according to claim 1, wherein the liposoluble polyol is a non-polymeric organic compound of formula (II):
W(OH)n(II) in which n denotes an integer greater than or equal to 2, W denotes a linear or branched or (hetero)cyclic, saturated or unsaturated C8-C30 multivalent radical, W also optionally bearing one or more functions chosen from ether, thioether, ester, ketone and amide functions.

22. The process according to claim 1, wherein the liposoluble polyol is a diol bearing a C8-C18 hydrocarbon-based chain.

23. The process according to claim 1, wherein the polyol is chosen from polyolefin diols, polydimethylsiloxane diols and polyester diols, ##STR00008## ##STR00009##

24. The process according to claim 1, wherein the liposoluble polyol is used in a mole ratio of OH group of the liposoluble polyol/maleic anhydride group of the ethylenic polymer ranging from 0.01 to 10.

25. The process according to claim 1, wherein the amine catalyst is chosen from catalysts bearing a primary amine function or bearing an aminidine function or bearing a guanidine function.

26. The process according to claim 1, wherein the amine catalyst is present in a content ranging from 0.1% to 0.5% by weight relative to the total weight of the composition derived from said mixture.

27. The process according to claim 1, wherein the composition comprises a hydrocarbon-based oil, preferably an apolar hydrocarbon-based oil containing from 8 to 14 carbon atoms.

28. The process according to claim 1, wherein the mixing of the composition comprising the block polymer of maleic anhydride and of the liposoluble polyol, or of the composition containing it, and of the amine catalyst is performed in a time of between 1 minute and 24 hours before application to keratin fibres.

29. The process according to claim 1, wherein the heating step is performed at a temperature ranging from 100 to 230 C.

30. The process according to claim 1, wherein the heating step is performed using an iron.

31. The process according to claim 1, wherein it comprises an additional step of drying the keratin fibres after step (i) and before step (ii).

32. A kit comprising: a first composition comprising a maleic anhydride ethylenic polymer as defined in claim 1 and optionally a physiologically acceptable medium, and a second composition comprising a liposoluble polyol compound and optionally a physiologically acceptable medium, the first composition or the second composition comprising an amine catalyst, the first and second compositions each being packaged in a separate packaging assembly.

33. A cosmetic composition obtained by mixing a maleic anhydride ethylenic polymer as defined in claim 1 or a composition containing it and comprising a physiologically acceptable medium, a liposoluble polyol compound or a composition containing it and comprising a physiologically acceptable medium, and an amine catalyst.

34. A polymer that obtained by reacting a liposoluble polyol compound with a maleic anhydride ethylenic polymer as defined in claim 1.

Description

EXAMPLE 1: 2-ETHYLHEXYL ACRYLATE/MALEIC ANHYDRIDE COPOLYMER (85/15 BY WEIGHT)POLYMER 1

[0219] 170 g of 2-ethylhexyl acrylate and 30 g of maleic anhydride were placed in a jacketed 1-litre reactor equipped with a stirring anchor. A mixture of 210 g of isododecane and 90 g of ethyl acetate was then added.

[0220] The reaction medium was brought to a temperature of 40 C. with stirring (150 rpm) and was sparged with argon for 10 minutes, followed by addition of 2 g of initiator tert-butyl peroxy-2-ethylhexanoate (Trigonox 21S from Akzo Nobel).

[0221] The heating of the jacket was set at 90 C. for 7 hours at 150 rpm.

[0222] The medium was then diluted with 300 g of isododecane, and then concentrated by distillation to remove the ethyl acetate and the unreacted maleic anhydride.

[0223] A solution containing 30% by weight of the copolymer in isododecane was finally obtained.

[0224] The polymer obtained has a molecular weight (Mw) of about 12 000 g/mol.

EXAMPLE 2: 2-ETHYLHEXYL ACRYLATE/MALEIC ANHYDRIDE COPOLYMER (80/20 BY WEIGHT)POLYMER 2

[0225] The polymer was prepared according to the procedure of Example 1, using 160 g of 2-ethylhexyl acrylate and 40 g of maleic anhydride.

[0226] A solution containing 32% by weight of the copolymer in isododecane (yield of greater than 90%) was finally obtained.

[0227] The polymer obtained has a molecular weight (Mw) of about 15 000 g/mol.

EXAMPLE 3: 2-ETHYLHEXYL ACRYLATE/PDMS METHACRYLATE/MALEIC ANHYDRIDE COPOLYMER (50/30/20 BY WEIGHT)POLYMER 3

[0228] The polymer was prepared according to the procedure of Example 1, using:

40 g of maleic anhydride with 28 g of isododecane and 21 g of ethyl acetate;
sparging with argon, followed by addition over 1 hour of a mixture of 100 g of 2-ethylhexyl acrylate, 60 g of PDMS methacrylate (X-22-2426 from Shin-Etsu; size of the PDMS chain=12 000 g/mol), 168 g of isododecane, 72 g of ethyl acetate and 2 g of Trigonox 21S.

[0229] A solution containing 40% by weight of the copolymer in isododecane was finally obtained.

EXAMPLE 4: 2-ETHYLHEXYL ACRYLATE/STEARYL ACRYLATE/MALEIC ANHYDRIDE COPOLYMER (50/30/20 BY WEIGHT)POLYMER 4

[0230] The polymer was prepared according to the procedure of Example 1, using:

20 g of 2-ethylhexyl acrylate and 20 g of maleic anhydride.
40 g of maleic anhydride with 28 g of isododecane and 21 g of ethyl acetate;
sparging with argon, followed by addition over 1 hour of a mixture of 100 g of 2-ethylhexyl acrylate, 60 g of stearyl methacrylate, 168 g of isododecane, 72 g of ethyl acetate and 2 g of Trigonox 21S.

[0231] A solution containing 41% by weight of the copolymer in isododecane was finally obtained.

[0232] The polymer obtained has a molecular weight (Mw) of close to 17 000 g/mol.

COMPARATIVE EXAMPLES 3 TO 7

[0233] The six compositions described below were prepared (weight percentages).

[0234] For each composition, all the ingredients were mixed at the same time at room temperature (25 C.) in a glass flask and the composition was then heated at 150 C. using a multi-well stirrer for 10 minutes. The state of the composition was then observed by turning the flask upside-down to thus determine whether the mixture reacted with a crosslinking reaction of the polymer (crosslinking inducing an increase in the viscosity of the initial mixture).

[0235] The following results were obtained:

TABLE-US-00001 Example 3 Example 4 Example 5 Polymer of Example 2 25% AM 25% AM 25% AM Diol 1 10% 10% 10% Diisopropylethylamine 0% 0.15% 0.5% Isododecane qs 100% qs 100% qs 100% State of the composition Fluid Set to a solid; Set to a solid; does not flow does not flow Diol 1: hydrogenated dihydroxylated polybutene GI-1000 from Nisso (hydroxyl number: 60-75 KOH mg/number-average = number-average molecular weight = 1500)

TABLE-US-00002 Example 6 Example 7 Example 8 Polymer of Example 2 25% AM 25% AM 25% AM Diol 2 10% 10% 10% Diisopropylethylamine 0% 0.15% 0.5% Isododecane qs 100% qs 100% qs 100% State of the composition Fluid Set to a solid; Set to a solid; does not flow does not flow Diol 2: PDMS-diOH KF-6001 from Shin-Etsu (hydroxyl number = 62 mg KOH/g; viscosity at 25 C. = 45 mm.sup.2/s)

[0236] The results obtained show that the compositions according to the invention (Examples 4, 5, 7, 8) thickened after heating, which proves that the crosslinking reaction of the polymer with the diol has indeed taken place.

[0237] The same test performed without catalyst (Examples 3, 6) or without performing the heating step for 10 minutes at 150 C., leads to compositions that are all fluid: without the heating step, crosslinking of the polymer does not take place. Similarly, without the catalyst, crosslinking of the polymer does not take place.

COMPARATIVE EXAMPLES 9 AND 10

[0238] The following two compositions were prepared (weight percentages):

TABLE-US-00003 Example 9 Example 10 Polymer of Example 2 10% AM Polymer of Example 3 10% AM Diol 1 5% Diol 2 5% Diisopropylethylamine 0.15% 0.15% Isododecane qs 100% qs 100%

[0239] Locks of hair were treated according to the following protocol:

[0240] 2.7 g locks of natural Caucasian hair were used.

[0241] The locks were washed with Ultra Doux camomile shampoo (from La Scad) by applying 1.2 g of shampoo to a lock of wet hair. The lock was then rinsed, then drained, then dried under a hood at 60 C. for 10 minutes.

[0242] 5.4 g of the test composition were then applied to the lock of hair. The lock was then dried at 60 C. (under a hood) for 15 minutes, and a straightening iron heated to 210 C. was then applied for 15 minutes by making 15 sweeps along the length of the lock (each sweep lasting about 4 seconds). The fixing quality of the lock was evaluated.

[0243] Washing with water was then performed by immersing the lock of treated hair in water (at room temperature, 25 C.) for 5 minutes. The lock was then drained and then dried under a hood at 60 C. for 15 minutes. The fixing quality of the lock of hair was again evaluated.

[0244] For comparison of the effect of the heating step performed with the curling iron heated to 210 C., the same protocol is performed on another lock of hair, but without performing the application of the curling iron.

[0245] The fixing quality of the lock of hair was evaluated by observing the more or less rigid appearance of the lock: the lock is taken by one of its ends with the fingers and turned upside-down, holding it at the bottom; the shape of the lock is then observed; either the lock retains its shape, which means that the lock is fixed very well; or the lock becomes deformed (under the effect of gravity) which means that the lock is not fixed very well.

[0246] The fixing quality of the lock of hair was evaluated according to the following grading:

[0247] Lock without fixing:

[0248] Lock with weak fixing: +

[0249] Lock with moderate fixing: ++

[0250] Lock with very good fixing: +++

[0251] The following results were obtained:

TABLE-US-00004 Example Example Example Example 9 with 9 without 10 with 10 without heat heat heat heat Fixing before washing +++ + +++ + Fixing after washing ++ + ++ +

[0252] The results obtained show that the locks of Examples 9 and 10 treated via the process according to the invention have good fixing properties before and after washing with water. These properties are superior to those of the locks of Examples 9 and 10 which did not undergo a heating step with the curling iron.

EXAMPLE 11

[0253] The following composition is prepared (weight percentage):

TABLE-US-00005 Polymer 1 (Example 1) 8% Hydrogenated dihydroxylated polybutene 4% (GI-1000 from Nisso) Diisopropylethylamine 0.12% Isododecane qs 100%

[0254] The composition is applied to the hair, left to dry for 15 minutes at room temperature, and the curling iron heated to 210 C. is then applied to the locks.

[0255] The hair thus treated has good, water-resistant fixing.

EXAMPLE 12

[0256] The following composition is prepared (weight percentage):

TABLE-US-00006 Polymer 4 (Example 4) 6% Hydrogenated dihydroxylated polybutene 3% PDMS-diOH KF-6001 from Shin-Etsu Diisopropylethylamine 0.09% Isododecane qs 100%

[0257] The composition is applied to the hair, left to dry for 15 minutes at room temperature, and the curling iron heated to 210 C. is then applied to the locks.

[0258] The hair thus treated has good, water-resistant fixing.

EXAMPLE 13

[0259] The following composition is prepared (weight percentage):

TABLE-US-00007 Polymer 4 (Example 4) 6% 1,12-Dodecanediol 2% Diisopropylethylamine 0.09% Isododecane qs 100%

[0260] The composition is applied to the hair, left to dry for 15 minutes at room temperature, and the curling iron heated to 210 C. is then applied to the locks.

[0261] The hair thus treated has good, water-resistant fixing.