BLOCK POLYMER BEARING ALKOXYSILANE GROUPS AND COSMETIC USE THEREOF

Abstract

The invention relates to a cosmetic process for caring for or making up keratin materials, comprising: either the topical application to the keratin materials of an anhydrous mixture of a cosmetic composition comprising a maleic anhydride block polymer and of an amino alkoxysilane compound; or the sequential application to the keratin materials of an anhydrous cosmetic composition comprising a maleic anhydride block polymer and of an anhydrous cosmetic composition containing an amino alkoxysilane, said block polymer comprising: a first block with a glass transition temperature (Tg) of greater than or equal to 40 C., obtained from a monomer CH.sub.2C(R.sub.1)COOR.sub.2 in which R.sub.1H or methyl, R.sub.2C.sub.4 to C.sub.12 cycloalkyl group; and a second block with a glass transition temperature (Tg) of less than or equal to 20 C. derived from a maleic anhydride monomer and from a monomer CH.sub.2C(R.sub.1)COOR.sub.3 in which R.sub.1H or methyl, R.sub.3=linear or branched C.sub.1 to C.sub.6 unsubstituted alkyl group, with the exception of a tert-butyl group, or a methoxyethyl group. The invention also relates to the polymer bearing an alkoxysilane group obtained by reacting said block polymer with said amino alkoxysilane. The process makes it possible to obtain a non-tacky and transfer-resistant film-forming deposit that has good persistence and that is resistant to water, to oil and to sebum.

Claims

1. A cosmetic process for treating keratin materials, comprising: either the topical application to the keratin materials of an anhydrous (extemporaneous) mixture of a cosmetic composition comprising a maleic anhydride block polymer and of an amino alkoxysilane compound (I) or of a cosmetic composition containing same; or the sequential application to the keratin materials of an anhydrous cosmetic composition comprising a maleic anhydride block polymer and of an amino alkoxysilane compound (I) or of an anhydrous cosmetic composition containing same, said block polymer comprising: at least one first block with a glass transition temperature (Tg) of greater than or equal to 40 C. and obtained from at least one (meth)acrylate monomer of formula CH.sub.2C(R.sub.1)COOR.sub.2 in which R.sub.1 represents H or a methyl radical, R.sub.2 represents a C.sub.4 to C.sub.12 cycloalkyl group; and at least one second block with a glass transition temperature (Tg) of less than or equal to 20 C. and obtained from at least one maleic anhydride monomer and from at least one (meth)acrylate monomer of formula CH.sub.2C(R.sub.1)COOR.sub.3 in which R.sub.1 represents H or a methyl radical, R.sub.3 representing a linear or branched C.sub.1 to C.sub.6 unsubstituted alkyl group, with the exception of the tert-butyl group, or a methoxyethyl group; said amino alkoxysilane having the formula (I):
RNHR.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x (I) in which: R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.20 hydrocarbon-based divalent group, which may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R.sub.1 being linked to the silicon atom directly via a carbon atom; RH or a C.sub.1-C.sub.4 alkyl group, preferably H; R.sub.2 and R.sub.3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, z denotes an integer ranging from 1 to 3, and x denotes an integer ranging from 0 to 2, with z+x=3.

2. The process according to claim 1, wherein the first block of the block polymer is obtained from at least one acrylate monomer of formula CH.sub.2CHCOOR.sub.2 in which R.sub.2 represents a C.sub.4 to C.sub.12 cycloalkyl group, and from at least one methacrylate monomer of formula CH.sub.2C(CH.sub.3)COOR.sub.2 in which R.sub.2 represents a C.sub.4 to C.sub.12 cycloalkyl group; and optionally an additional monomer chosen from linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates.

3. The process according to claim 1, wherein for the first block of the block polymer, said acrylate monomer and said methacrylate monomer are in acrylate/methacrylate mass proportions of between 30/70 and 70/30.

4. The process according to claim 2, wherein the first block of the block polymer is obtained by polymerization of isobornyl methacrylate and isobornyl acrylate.

5. The process according to claim 1, wherein the proportion of the first block in the block polymer ranges from 60% to 80%.

6. The process according to claim 1, wherein the second block of the block polymer comprises a monomer chosen from isobutyl acrylate, ethyl acrylate, n-butyl acrylate and methoxyethyl acrylate, or mixtures thereof.

7. The process according to claim 1, wherein, for the second block of the block polymer, the maleic anhydride and said (meth)acrylate monomer are in (meth)acrylate/maleic anhydride mass proportions ranging from 1 to 10.

8. The process according to claim 1, wherein the second block of the block polymer comprises an additional silicone monomer of formula (II): ##STR00003## 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 O ether bonds; R10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms; n denotes an integer ranging from 1 to 300.

9. The process according to claim 1, wherein the proportion of the second block in the block polymer ranges from 20% to 40% by weight of the polymer.

10. The process according to claim 1, wherein said block polymer comprises an intermediate segment comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block.

11. The process according to claim 1, wherein said block polymer has a polydispersity index of greater than 2.

12. The process according to claim 1, wherein at the maleic anhydride block polymer is present in the composition applied to the keratin materials in a content ranging from 0.1% to 40% by weight, relative to the total weight of the composition derived from the extemporaneous mixture.

13. The process according to claim 1, wherein, for the amino alkoxysilane (I): RH; R.sub.1 is a linear saturated C.sub.1-C.sub.6 hydrocarbon-based chain; R.sub.2 represents an alkyl group comprising from 1 to 4 carbon atoms; R.sub.3 represents an alkyl group comprising from 1 to 4 carbon atoms.

14. The process according to claim 1, wherein the amino alkoxysilane (I) is chosen from 3-aminopropyltriethoxysilane, 3-aminoethyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.

15. The process according to claim 1, wherein the amino alkoxysilane (I) is used in a mole ratio of amino alkoxysilane/maleic anhydride group of the block polymer ranging from 0.01 to 10.

16. The process according to claim 1, wherein the composition comprises a hydrocarbon-based oil.

17. The process according to claim 1, wherein a mixture, prepared less than 5 minutes before application to keratin materials, of the composition comprising the maleic anhydride block polymer and of the amino alkoxysilane or of the composition containing same is applied to the keratin materials.

18. The process according to claim 1, wherein the composition comprising the maleic anhydride block polymer is first applied to keratin materials, and the amino alkoxysilane (I) or an anhydrous composition containing same and comprising a physiologically acceptable medium is then applied.

19. The process according claim 1, wherein the amino alkoxysilane (I), or an anhydrous composition containing same and comprising a physiologically acceptable medium, is first applied to keratin materials, and the composition comprising the maleic anhydride block polymer is then applied.

20. The process according to claim 1, wherein it is performed on the skin, the lips, the eyelashes, the hair or the nails.

21. A composition obtained by mixing an anhydrous composition comprising a maleic anhydride block polymer as defined in claim 1, and an amino alkoxysilane having the formula (I):
RNHR.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x (I) in which: R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.20 hydrocarbon-based divalent group, which may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R.sub.1 being linked to the silicon atom directly via a carbon atom; RH or a C.sub.1-C.sub.4 alkyl group, preferably H; R.sub.2 and R.sub.3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, z denotes an integer ranging from 1 to 3, and x denotes an integer ranging from 0 to 2, with z+x=3 or an anhydrous composition containing same and comprising a physiologically acceptable medium.

22. The composition according to claim 21, wherein it is a makeup composition comprising a volatile oil and a non-volatile oil, preferably a hydrocarbon-based volatile oil and a hydrocarbon-based non-volatile oil.

23. A kit comprising a first anhydrous composition comprising a maleic anhydride block polymer as defined in claim 1 and a second anhydrous composition comprising an amino alkoxysilane having the formula (I):
RNHR.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x (I) in which: R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.20 hydrocarbon-based divalent group, which may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R.sub.1 being linked to the silicon atom directly via a carbon atom; RH or a C.sub.1-C.sub.4 alkyl group, preferably H; R.sub.2 and R.sub.3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, z denotes an integer ranging from 1 to 3, and x denotes an integer ranging from 0 to 2, with z+x=3 and comprising a physiologically acceptable medium, the first and second compositions each being packaged in a separate packaging assembly.

24. A polymer obtained by reacting an amino alkoxysilane having the formula (I):
RNHR.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x (I) in which: R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.20 hydrocarbon-based divalent group, which may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R.sub.1 being linked to the silicon atom directly via a carbon atom; RH or a C.sub.1-C.sub.4 alkyl group, preferably H; R.sub.2 and R.sub.3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, z denotes an integer ranging from 1 to 3, and x denotes an integer ranging from 0 to 2, with z+x=3 with a maleic anhydride block polymer as defined in claim 1.

Description

EXAMPLE 1

Isobornyl methacrylate/isobornyl acrylate (35/35 by weight)-co-isobutyl acrylate/maleic anhydride (25/5 by weight) copolymer

[0175] 1 litre of isododecane was placed in a jacketed 1-litre reactor equipped with a stirring anchor and the temperature was then increased from 25 C. to 90 C. over 1 hour

[0176] 105 g of isobornyl methacrylate, 105 g of isobornyl acrylate and 1.8 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane (Trigonox 141 from AkzoNobel) were then added over 1 hour. The reaction mixture was stirred for 1 hour 30 minutes at 90 C.

[0177] 75 g of isobutyl acrylate, 15 g of maleic anhydride and 1.2 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane were then added over 30 minutes.

[0178] The reaction mixture was stirred for 3 hours at 90 C. and was then cooled to room temperature (25 C.) and diluted by adding 150 g of isododecane.

[0179] A solution containing 50% polymer active material in isododecane was thus obtained.

[0180] The polymer obtained has a number-average molecular weight (Mn) of 18 000 and a weight-average molecular weight (Mw) of 290 200; with an Ip=8.9.

COMPARATIVE EXAMPLES 2 TO 7

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

[0181] The three base coat makeup compositions (lip gloss; foundation) and a top coat composition containing APTES described below were prepared.

[0182] Each base coat composition was applied onto a skin equivalent support made of elastomer by producing a deposit with a wet thickness of 100 m, which was left to dry at room temperature (25 C.) for 24 hours.

[0183] The top coat composition was then applied onto each dry base coat deposit by producing a deposit with a wet thickness of 100 m, which was left to dry at room temperature (25 C.) for 24 hours.

[0184] The state of the film obtained before (outside the invention) and after (invention) applying the top coat composition was then observed.

[0185] The resistance of the film obtained was evaluated by separately applying 0.5 ml of water, 0.5 ml of olive oil and 0.5 ml of sebum; after 5 minutes of contact, the surface of the film was rubbed with cotton wool and the state of the film was then observed (degraded or undegraded appearance of the film).

[0186] The tackiness of the film and its capacity for transferring or not transferring on touching the film with a finger were also evaluated.

[0187] The evaluation was made in the following manner:

[0188] +++: very efficient evaluated cosmetic property

[0189] ++: moderately efficient evaluated cosmetic property

[0190] +: sparingly efficient evaluated cosmetic property

[0191] 0: inefficient evaluated cosmetic property

[0192] The following results were obtained:

TABLE-US-00001 Example 3 Example 5 Example 2 (invention) Example 4 (invention) Base Coat Polymer of 25 g AM 25 g AM 20 g AM 20 g AM Example 1 Pigmentary paste 5 g 5 g 5 g 5 g containing 40% by with DC with DC with DC with DC weight of pigment Red 7 Red 7 Red 7 Red 7 in isododecane Disteardimonium 10 g 10 g 10 g 10g hectorite (Bentone Gel ISD V from Elementis) Isohexadecane 40 g 40 g Isododecane qs 100 g qs 100 g qs 100 g qs 100 g Top Coat APTES 5 g 5 g Isododecane 95 g 95 g Evaluation of the film Appearance of Homo- Homo- Homo- Homo- the film geneous geneous geneous geneous film film film film Water resistance ++ +++ ++ +++ Olive oil + +++ + +++ resistance Sebum resistance + +++ + +++ Non-tacky + +++ 0 +++ Transfer-resistant + +++ 0 +++ Example 7 Example 6 (invention) Base Coat Polymer of 25 g AM 25 g AM Example 1 Pigmentary paste 5 g 5 g containing 40% by with red with red weight of pigment iron oxide iron oxide in isododecane Disteardimonium 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane 65 g 65 g Top Coat APTES 15 g Isododecane 95 g Evaluation of the film Appearance of Homo- Homo- the film geneous geneous film film Water resistance ++ +++ Olive oil + +++ resistance Sebum resistance + +++ Non-tacky + +++ Transfer-resistant + +++

[0193] The results obtained show that the deposits resulting from the application of polymer 1, with or without isohexadecane, followed by APTES (Examples 3, 5; 7) form a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to water, to oil and to sebum, whereas the application of polymer 1 alone (Examples 2, 4; 6) forms a deposit that is much more tacky and that transfers onto the finger and has poorer resistance to water, to oil and to sebum.

[0194] Thus, the non-tacky aspect and transfer-resistant aspect on contact with the finger, and also the resistance of the film to contact with olive oil and sebum are markedly improved with the application of the top coat composition containing APTES.

[0195] The lipstick compositions of Examples 3 and 5 applied to the lips thus make it possible to obtain a non-tacky, transfer-resistant and water-, oil- and sebum-resistant makeup which thus has good persistence.

[0196] The compositions of Example 7 applied to the skin thus make it possible to obtain a non-tacky, transfer-resistant and water-, oil- and sebum-resistant makeup which thus has good persistence.

COMPARATIVE EXAMPLES 8 AND 9

Cosmetic Evaluation of Makeup Compositions with Application in One Step

[0197] The makeup (lip gloss) compositions described below containing the polymer of Example 1 with or without APTES were prepared, and the composition was then applied onto a skin equivalent support made of elastomer by producing a deposit with a wet thickness of 100 m, which was left to dry at room temperature (25 C.) for 24 hours.

[0198] The cosmetic properties of the film obtained were evaluated according to the tests described previously in Examples 2 to 7.

[0199] The following results were obtained:

TABLE-US-00002 Example 9 Example 8 (invention) Composition Polymer of 25 g AM 25 g AM Example 1 Pigmentary paste 5 g 5 g containing 40% by with DC with DC weight of pigment Red 7 Red 7 in isododecane Disteardimonium 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane 65 g 65 g Evaluation of the film Appearance of Homo- Homo- the film geneous geneous film film Water resistance ++ +++ Olive oil + +++ resistance Sebum resistance + +++ Non-tacky + +++ Transfer-resistant + +++

[0200] The results obtained show that the deposit resulting from the application of polymer 1 mixed with APTES (Example 9) forms a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to water, to oil and to sebum, whereas the application of polymer 1 alone (Example 8) forms a deposit that is much more tacky and that transfers onto the finger and has poorer resistance to water, to oil and to sebum.

[0201] Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film to contact with water, olive oil and sebum, are markedly improved with the application of the composition containing the polymer of Example 1 and APTES.

[0202] The lipstick compositions of Example 9 applied to the lips thus make it possible to obtain a non-tacky, transfer-resistant and water-, oil- and sebum-resistant makeup which thus has good persistence.

COMPARATIVE EXAMPLES 10 TO 12

Cosmetic Evaluation of a Hair Composition

[0203] 0.5 g of a base coat composition containing 10% AM of the polymer of Example 1 in isododecane was applied to a 2.7 g lock of washed and dried hair (Lock No. 1). The treated lock was left to dry naturally (25 C.) for 24 hours. 0.5 g of a top coat composition containing 10% AM of APTES in isododecane was then applied to the lock, which was then left to dry naturally for 24 hours (Example 12 according to the invention). The base coat composition alone was applied to another lock of hair (Lock No. 2) (Example 10). The top coat composition alone was applied to another lock of hair (Lock No. 3) (Example 11).

[0204] 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.

[0205] The persistence with respect to water of the fixing property of the treated locks was then evaluated by immersing the treated locks in water for 5 minutes. The locks were then dried manually, followed by drying under a hood. The rigidity of the three locks was observed.

[0206] It was found that the lock treated according to Example 12 before and after immersion in water has a rigid form with good hair fixing.

[0207] The fixing of the hair of Example 12 thus shows good persistence with respect to water.

[0208] The locks treated according to Examples 10 and 11 have a rigid form before immersion in the water, but lose their rigidity after immersion in the water: the lock is supple and has no fixing.