Cosmetic process for treating keratin materials with a maleic anhydride ethylenic polymer

Abstract

The invention relates to a cosmetic process for treating keratin materials, comprising: either the sequential application to the keratin materials of a composition comprising a maleic anhydride ethylenic polymer and of an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes, or the topical application to the keratin materials of a composition derived from the mixing of a composition comprising a maleic anhydride acrylic polymer and of an amine compound chosen from amino alkoxysilanes; the 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; the compositions used being anhydrous when the amine compound is an amino alkoxysilane. The process makes it possible to obtain a film-forming deposit that has good resistance to water, to oil and to sebum. The film is also non-tacky and transfer-resistant.

Claims

1. A cosmetic process for treating keratin materials, comprising: either sequentially applying to the keratin materials 1) a composition comprising a maleic anhydride ethylenic polymer and 2) at least one amine component chosen from an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes, and a composition containing the amine compound and comprising a physiologically acceptable medium; or topically applying to the keratin materials a composition derived from mixing 1) a composition comprising a maleic anhydride ethylenic polymer and 2) at least one amine component chosen from an amine compound chosen from amino alkoxysilanes, and a composition containing the amine compound and comprising a physiologically acceptable medium; the ethylenic polymer being a random or gradient polymer derived from the polymerization of: (a) 45% to 95% by weight, relative to the total weight of monomers, of at least one ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group; (b) 5% to 25% by weight of maleic anhydride; and (c) 0 to 50% by weight of at least one additional monomer chosen from: (i) polydimethylsiloxane silicone monomers bearing a mono(meth)acryloyloxy end group of formula (I) below: ##STR00007## in which: R.sub.8 denotes a hydrogen atom or a methyl group; R.sub.9 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; R.sub.10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms; and n denotes an integer ranging from 1 to 300; and (ii) linear or branched C.sub.1-C.sub.6 alkyl (meth)acrylate or C.sub.6-C.sub.12 cycloalkyl (meth)acrylate non-silicone monomers; the compositions used being anhydrous when the amine compound is an amino alkoxysilane.

2. The process according to claim 1, wherein the ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group is chosen from: a) linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates; b) (meth)acrylamides of formula CH.sub.2C(R.sub.1)CONR.sub.3R.sub.4 in which R.sub.1 represents a hydrogen atom or a methyl radical, R.sub.3 represents a hydrogen atom or a linear or branched C.sub.1-C.sub.12 alkyl group, and R.sub.4 represents a linear or branched C.sub.8 to C.sub.12 alkyl group; c) vinyl esters of formula R.sub.5COCHCH.sub.2 in which R.sub.5 represents a linear or branched C.sub.8-C.sub.22 alkyl group; and d) ethers of formula R.sub.6OCHCH.sub.2 in which R.sub.6 represents a linear or branched C.sub.8-C.sub.22 alkyl group.

3. The process according to claim 1, wherein the ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group is chosen from C.sub.8-C.sub.22.

4. The process according to claim 1, wherein the ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group is chosen from 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, lauryl acrylate, lauryl methacrylate, behenyl acrylate, behenyl methacrylate, stearyl acrylate, and stearyl methacrylate.

5. The process according to claim 1, wherein the ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group is present in said ethylenic polymer in a content ranging from 45% 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 polydimethylsiloxane silicone monomer: R.sub.8 denotes a methyl group; R.sub.9 denotes a linear divalent hydrocarbon-based group containing from 2 to 4 carbon atoms; R.sub.10 denotes a linear or branched alkyl group, comprising from 2 to 8 carbon atoms; and 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 C.sub.6-C.sub.12 cycloalkyl (meth)acrylates.

9. The process according to claim 1, wherein said ethylenic polymer comprises said additional polydimethylsiloxane silicone monomer.

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 C.sub.8-C.sub.22 alkyl (meth)acrylate; and (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 and 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 C.sub.8-C.sub.22 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; and (c) 0.5% to 50% by weight of said polydimethylsiloxane silicone monomer.

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

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 C.sub.8-C.sub.18 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; and (c) 0.5% to 50% by weight of C.sub.6-C.sub.12 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 and 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 C.sub.8-C.sub.18 alkyl (meth)acrylate; (b) 5% to 25% by weight of maleic anhydride; and (c) 0.5% to 50% by weight of a mixture of C.sub.6-C.sub.12 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/polydimethylsiloxane silicone monomer stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate/polydimethylsiloxane silicone monomer and 2-ethylhexyl acrylate/stearyl acrylate/maleic anhydride/isobornyl (meth)acrylate/polydimethylsiloxane silicone monomer.

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 ethylenic polymer is present in the composition in a content ranging from 0.1% to 40% by weight, relative to the total weight of the composition.

22. The process according to claim 1, wherein the amine compound is a polyamine compound comprising from 2 to 20 carbon atoms.

23. The process according to claim 1, wherein the amine compound is chosen from N-methyl-1,3-diaminopropane, N-propyl-1,3-diaminopropane, N-isopropyl-1,3-diaminopropane, N-cyclohexyl-1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylenetriamine, 1,2-bis(3-aminopropylamino)ethane, N,N-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine and spermidine.

24. The process according to claim 1, wherein the amine compound is chosen from amine-based polymers.

25. The process according to claim 24, wherein the amine compound is chosen from poly((C.sub.2-C.sub.5)alkyleneimines); polyvinylamines and copolymers thereof; vinylamine/vinylformamide copolymers; polyamino acids bearing NH.sub.2 groups; amino polyvinyl alcohol, acrylamidopropylamine-based copolymers; chitosans; polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains; amodimethicones of formula (D): ##STR00008## in which R, R and R, which may be identical or different, each represent a C.sub.1-C.sub.4 alkyl or hydroxyl group, A represents a C.sub.3 alkylene group and m and n are such that the weight-average molecular mass of the compound is between 5000 and 500,000 approximately; amodimethicones of formula (K): ##STR00009## in which: R1 and R2, which may be identical or different, represent a linear or branched, saturated or unsaturated alkyl group comprising from 6 to 30 carbon atoms, A represents a linear or branched alkylene radical group containing from 2 to 8 carbon atoms, x and y are numbers ranging from 1 to 5000; polytetrahydrofuran (or polytetramethylene glycol) ,-diamines and polybutadiene ,-diamines; polyamidoamine dendrimers bearing amine end functions; poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine side functions; and polyethylene glycol and/or polypropylene glycol ,-diamines; ethylenediamine, 1,3-propylenediamine and 1,4-butylenediamine.

26. The process according to claim 1, wherein the amine compound is an amino alkoxysilane of formula (III):
R.sub.1Si(OR.sub.2).sub.z(R.sub.3)(III) in which: R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.6 hydrocarbon-based chain substituted with a group chosen from the following groups: amine NH.sub.2 or NHR with RC.sub.1-C.sub.4 alkyl, an aryl or aryloxy group substituted with an amino group or with a C.sub.1-C.sub.4 aminoalkyl group, R.sub.1 optionally being 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, 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.

27. The process according to claim 1, wherein the amine compound is used in a mole ratio of amine group of the amine compound/maleic anhydride group of the ethylenic polymer ranging from 0.01 to 10.

28. The process according to claim 1, wherein the composition(s) used comprise a hydrocarbon-based oil.

29. The process according to claim 1, wherein the composition comprising the ethylenic polymer contains a silicone oil.

30. The process according to claim 1, wherein the composition comprising the maleic anhydride ethylenic polymer is applied first to the keratin materials, and at least one amine component chosen from an amine compound chosen from amino alkoxysilanes, and a composition containing the amine compound and comprising a physiologically acceptable medium.

31. The process according to claim 1, wherein at least one amine component chosen from an amine compound chosen from amino alkoxysilanes, and a composition containing the amine compound and comprising a physiologically acceptable medium, is applied first to the keratin materials, and the composition comprising the maleic anhydride ethylenic polymer is then applied.

32. The process according to claim 1, wherein a composition derived from mixing of 1) a composition comprising a maleic anhydride acrylic polymer and 2) at least one amine component chosen from an amine compound chosen from amino alkoxysilanes, and a composition containing the amine compound and comprising a physiologically acceptable medium, is applied topically to the keratin materials.

33. The process according to claim 1, wherein the keratin material is selected from the group of skin and lips.

34. A kit comprising a first composition comprising a maleic anhydride ethylenic polymer and a second composition comprising at least one amine component chosen from an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes and optionally comprising a physiologically acceptable medium, the first and second compositions each being packaged in a separate packaging assembly, the compositions being anhydrous when the amine compound is an amino alkoxysilane, said maleic anhydride ethylenic polymer consisting of: (a) 45% to 95% by weight, relative to the total weight of monomers, of an ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group chosen from: i) linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates; ii) (meth)acrylamides of formula CH.sub.2C(R.sub.1)CONR.sub.3R.sub.4 in which R.sub.1 represents a hydrogen atom or a methyl radical, R.sub.3 represents a hydrogen atom or a linear or branched C.sub.1-C.sub.12 alkyl group, and R.sub.4 represents a linear or branched C.sub.8 to C.sub.12 alkyl group; iii) vinyl esters of formula R.sub.5COOCHCH.sub.2 in which R.sub.5 represents a linear or branched C.sub.8-C.sub.22 alkyl group; and iv) ethers of formula R.sub.6OCHCH.sub.2 in which R.sub.6 represents a linear or branched C.sub.8-C.sub.22 alkyl group; (b) 5% to 25% by weight of maleic anhydride; and (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: ##STR00010## in which: R.sub.8 denotes a hydrogen atom or a methyl group; R.sub.9 denotes a linear or branched divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bond O; R.sub.10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms; and n denotes an integer ranging from 1 to 300; and (ii) linear or branched C.sub.1-C.sub.6 alkyl (meth)acrylate or C.sub.6-C.sub.12 cycloalkyl (meth)acrylate non-silicone monomers.

35. A composition obtained by mixing an ethylenic polymer, or a composition containing the ethylenic polymer and comprising a physiologically acceptable medium, and at least one amine component chosen from an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes or a composition containing the amine compound and comprising a physiologically acceptable medium, said maleic anhydride ethylenic polymer being a random or gradient polymer consisting of: (a) 45% to 95% by weight, relative to the total weight of monomers, of an ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group chosen from: i) linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates; ii) (meth)acrylamides of formula CH.sub.2C(R.sub.1)CONR.sub.3R.sub.4 in which R.sub.1 represents a hydrogen atom or a methyl radical, R.sub.3 represents a hydrogen atom or a linear or branched C.sub.1-C.sub.12 alkyl group, and R.sub.4 represents a linear or branched C8 to C12 alkyl group; iii) vinyl esters of formula R.sub.5COCHCH.sub.2 in which R.sub.5 represents a linear or branched C.sub.8-C.sub.22 alkyl group; and iv) ethers of formula R.sub.6OCHCH.sub.2 in which R.sub.6 represents a linear or branched C.sub.8-C.sub.22 alkyl group; (b) 5% to 25% by weight of maleic anhydride; and (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: ##STR00011## in which: R.sub.8 denotes a hydrogen atom or a methyl group; R.sub.9 denotes a linear or branched divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bond O; R.sub.10 denotes a linear or branched alkyl group containing from 1 to 10 carbon; and n denotes an integer ranging from 1 to 300; and (ii) linear or branched C.sub.1-C.sub.6 alkyl (meth)acrylate or C.sub.6-C.sub.12 cycloalkyl (meth)acrylate non-silicone monomers.

36. A polymer that may be obtained by reacting an at least one amine component chosen from an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes with a maleic anhydride ethylenic polymer, the reaction being performed in anhydrous medium when the amine compound is an amino alkoxysilane, said maleic anhydride ethylenic polymer being a random or gradient polymer consisting of: (a) 45% to 95% by weight, relative to the total weight of monomers, of an ethylenic monomer bearing a C.sub.8 to C.sub.22 linear or branched alkyl group chosen from: i) linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates; ii) (meth)acrylamides of formula CH.sub.2C(R.sub.1)CONR.sub.3R.sub.4 in which R.sub.1 represents a hydrogen atom or a methyl radical, R.sub.3 represents a hydrogen atom or a linear or branched C.sub.1-C.sub.12 alkyl group, and R.sub.4 represents a linear or branched C.sub.8 to C.sub.12 alkyl group; iii) vinyl esters of formula R.sub.5COOCHCH.sub.2 in which R.sub.5 represents a linear or branched C.sub.8-C.sub.22 alkyl group; and iv) ethers of formula R.sub.6OCHCH.sub.2 in which R.sub.6 represents a linear or branched C.sub.8-C.sub.22 alkyl group; (b) 5% to 25% by weight of maleic anhydride; and (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: ##STR00012## in which: R.sub.8 denotes a hydrogen atom or a methyl group; R.sub.9 denotes a linear or branched divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bond O; R.sub.10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms; and n denotes an integer ranging from 1 to 300; and (ii) linear or branched C.sub.1-C.sub.6 alkyl (meth)acrylate or C.sub.6-C.sub.12 cycloalkyl (meth)acrylate non-silicone monomers.

37. A composition comprising, in a physiologically acceptable medium, a polymer according to claim 36.

38. The process according to claim 1, wherein the maleic anhydride ethylenic polymer is a random copolymer.

Description

EXAMPLE 1

2-Ethylhexyl Acrylate/Maleic Anhydride Copolymer (85/15 by Weight)

(1) 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.

(2) The 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 AkzoNobel).

(3) The heating of the jacket was set at 90 C. for 7 hours at 150 rpm.

(4) 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.

(5) A solution containing 30% by weight of the copolymer in isododecane was finally obtained.

(6) The polymer obtained has a molecular weight (Mw) of close to 12 000 g/mol.

EXAMPLE 2

2-Ethylhexyl Acrylate/Maleic Anhydride Copolymer (80/20 by Weight)

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

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

(9) The polymer obtained has a molecular weight (Mw) of close to 15000 g/mol.

EXAMPLE 3

2-Ethylhexyl Acrylate/PDMS Methacrylate*/Maleic Anhydride Copolymer (50/30/20 by Weight)

(10) The polymer was prepared according to the procedure of Example 1, using:

(11) 40 g of maleic anhydride with 28 g of isododecane and 21 g of ethyl acetate;

(12) 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.

(13) 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)

(14) The polymer was prepared according to the procedure of Example 1, using:

(15) 20 g of 2-ethylhexyl acrylate and 20 g of maleic anhydride;

(16) 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.

(17) A solution containing 41% by weight of the copolymer in isododecane was finally obtained.

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

COMPARATIVE EXAMPLES 5 TO 10

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(19) The three makeup compositions (lip gloss) of base coat containing the polymer of Example 1 or of Example 2 and a top coat composition containing APTES described below were prepared.

(20) 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.

(21) 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.

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

(23) The elastomer support was also deformed manually and the state of the film after this deformation was observed to determine its resistance to deformation.

(24) The strength 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).

(25) The tackiness of the film and its capacity for transferring or not transferring on touching the film with a finger were also evaluated.

(26) The evaluation was made in the following manner:

(27) +++: very efficient evaluated cosmetic property

(28) ++: moderately efficient evaluated cosmetic property

(29) +: sparingly efficient evaluated cosmetic property

(30) 0: inefficient evaluated cosmetic property

(31) The following results were obtained:

(32) TABLE-US-00001 Example 6 Example 8 Example 5 (invention) Example 7 (invention) Polymer of 25 g AM 25 g AM Example 1 Polymer of 20 g AM 20 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC 5 g with DC 5 g with DC containing 40% Red 7 Red 7 Red 7 Red 7 by weight of pigment in isododecane Disteardimonium 10 g 10 g 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) 2-Octyldodecanol 20 g 20 g Isododecane qs 100 g qs 100 g qs 100 g qs 100 g APTES 5 g 5 g Isododecane 95 g 95 g Evaluation of the film Appearance of Homogeneous Homogeneous Homogeneous Homogeneous the film film film film film Resistance to Yes without Yes without Yes without Yes without deformation damaging the damaging the damaging the damaging the film film film film Water resistance ++ +++ ++ +++ Olive oil 0 +++ 0 +++ resistance Sebum resistance 0 +++ 0 +++ Non-tacky 0 +++ 0 +++ Transfer-resistant 0 +++ 0 +++

(33) TABLE-US-00002 Example 10 Example 9 (invention) Polymer of 25 g AM 25 g AM Example 1 Pigmentary 5 g with red 5 g with red paste containing iron oxide iron oxide 40% by weight of pigment in isododecane Disteardimonium 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane 65 g 65 g APTES 15 g Isododecane 95 g Evaluation of the film Appearance of Homogeneous Homogeneous the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil 0 +++ resistance Sebum 0 +++ resistance Non-tacky + +++ Transfer- 0 +++ resistant

(34) The results obtained show that the deposits resulting from the application of polymer 1 followed by APTES (Examples 6, 10) and those resulting from the application of polymer 2 with 2-octyldodecanol (Example 8) form a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation, to water, to oil and to sebum, whereas the sole application of polymer 1 (Examples 5, 9) or of polymer 2 (Example 7) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

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

(36) The lipstick compositions of Examples 6 or 8 or 10 applied to the lips thus make it possible to obtain a non-tacky, transfer-resistant and oil- and sebum-resistant makeup which thus has good staying power.

COMPARATIVE EXAMPLES 11 TO 14

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(37) The makeup compositions (lip gloss) described below containing the polymer of Example 2 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.

(38) The cosmetic properties of the film obtained were evaluated according to the tests described previously in Examples 5 to 10.

(39) The following results were obtained:

(40) TABLE-US-00003 Example 12 Example 14 Example 11 (invention) Example 13 (invention) Composition Polymer of 20 g AM 20 g AM 20 g AM 20 g AM Example 1 Pigmentary 5 g with DC 5 g with DC 5 g with DC 5 g with DC paste containing Red 7 Red 7 Red 7 Red 7 40% by weight of pigment in isododecane Disteardimonium 10 g 10 g 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) APTES 5 g 5 g 2- 20 g 20 g Octyldodecanol Isododecane 65 g 60 g 45 g 60 g Evaluation of the film Appearance of Homogeneous Homogeneous Homogeneous Homogeneous the film film film film film Resistance to Yes without Yes but with Yes without Yes without deformation damaging the fragmentation damaging the damaging the film of the film film film Water resistance ++ +++ ++ +++ Olive oil 0 +++ 0 +++ resistance Sebum 0 +++ 0 +++ resistance Non-tacky 0 +++ 0 +++ Transfer- 0 +++ 0 +++ resistant

(41) The results obtained show that the deposit resulting from the application of polymer 2 mixed with APTES, with or without 2-octyldodecanol (Examples 12, 14) 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 sole application of polymer 2, with or without 2-octyldodecanol (Examples 11, 13) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

(42) Thus, the non-tacky and transfer-resistant aspect on contact of the finger with the film, and also the resistance of the film on contact with olive oil and sebum, are markedly improved with the application of the composition containing the polymer of Example 2 and APTES.

(43) The lipstick composition (Examples 12, 14) applied to the lips thus makes it possible to obtain a non-tacky, transfer-resistant and water-, oil- and sebum-resistant makeup which thus has good staying power.

COMPARATIVE EXAMPLES 15 TO 20

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(44) The makeup compositions (lip gloss; foundation) described below containing the polymer of Example 2 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.

(45) The cosmetic properties of the film obtained were evaluated according to the tests described previously in Examples 5 to 10.

(46) The following results were obtained:

(47) TABLE-US-00004 Example Example Example Example Example Example 15 16 17 18 19 20 Polymer of 20 g 20 g 25 g 25 g 20 g 20 g Example 2 Pigmentary 5 g with 5 g with 5 g with 5 g with 5 g with 5 g with paste DC Red 7 DC Red 7 DC Red 7 DC Red 7 red iron red iron containing oxide oxide 40% by weight of pigment in isododecane APTES 5 g 5 g 5 g Isododecane 75 g 70 g 70 g 65 g 75 g 70 g Appearance Homogeneous Homogeneous Homogeneous Homogeneous Homogeneous Homogeneous of the film film film film film film film Resistance to Yes Yes Yes Yes Yes Yes deformation without without without without without without damaging damaging damaging damaging damaging damaging the film the film the film the film the film the film Water ++ +++ ++ +++ ++ +++ resistance Olive oil 0 +++ 0 +++ 0 +++ resistance Sebum 0 +++ 0 +++ 0 +++ resistance Non-tacky 0 +++ 0 +++ 0 +++ Transfer- 0 +++ 0 +++ 0 +++ resistant

(48) The results obtained show that the deposit resulting from the application of polymer 2 mixed with APTES, with or without 2-octyldodecanol (Examples 16, 18, 20) 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 sole application of polymer 2, with or without 2-octyldodecanol (Examples 15, 17, 19) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

(49) Thus, the non-tacky and transfer-resistant aspect on contact of the finger with the film, and also the resistance of the film on contact with water, olive oil and sebum, are markedly improved with the application of the composition containing the polymer of Example 2 and APTES.

(50) The lipstick composition (Examples 16, 18) applied to the lips thus makes it possible to obtain a non-tacky, transfer-resistant and oil- and sebum-resistant makeup which thus has good staying power.

(51) The composition of Example 20 applied to the skin thus makes it possible to obtain a non-tacky, transfer-resistant and water-, oil- and sebum-resistant makeup which thus has good staying power.

COMPARATIVE EXAMPLES 21 TO 23

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(52) The three makeup compositions (lip gloss) of base coat containing the polymer of Example 1 and a top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane described below were prepared.

(53) The compositions were applied and the cosmetic properties of the film obtained were evaluated as described previously in Examples 5 to 10.

(54) The following results were obtained:

(55) TABLE-US-00005 Example 21 Example 23 Example 5 (invention) Example 22 (invention) Polymer of Example 1 25 g AM 25 g AM 20 g AM 20 g AM Pigmentary paste 5 g with DC 5 g with DC 5 g with DC 5 g with DC containing 40% by weight Red 7 Red 7 Red 7 Red 7 of pigment in isododecane Disteardimonium hectorite 10 g 10 g 10 g 10 g (Bentone Gel ISD V from Elementis) 2-Octyldodecanol 20 g 20 g Isododecane qs 100 g qs 100 g qs 100 g qs 100 g 3-Aminopropyl-terminated 5 g 5 g polydimethylsiloxane (Mn 2 500; reference 481688 from Sigma) Isododecane 95 g 95 g Evaluation of the film Appearance of the film Homogeneous Homogeneous Homogeneous Homogeneous film film film film Resistance to deformation Yes without Yes without Yes without Yes without damaging the damaging damaging damaging film the film the film the film Water resistance ++ +++ ++ +++ Olive oil resistance 0 +++ 0 +++ Sebum resistance 0 +++ 0 +++ Non-tacky 0 +++ 0 +++ Transfer-resistant 0 +++ 0 +++

(56) The results obtained show that the deposits resulting from the application of polymer 1 followed by 3-aminopropyl-terminated polydimethylsiloxane (Example 21) with 2-octyldodecanol (Example 23) form a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation, to water, to oil and to sebum, whereas the sole application of polymer 1 (Examples 5, 22) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

(57) Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film on contact with water, olive oil and sebum are markedly improved with the application of the top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane.

(58) The lipstick compositions of Examples 21 or 23 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 staying power.

COMPARATIVE EXAMPLES 24 AND 25

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(59) The 2 makeup compositions (lipstick) of base coat containing the polymer of Example 4 and a top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane described below were prepared.

(60) The compositions were applied and the cosmetic properties of the film obtained were evaluated as described previously in Examples 5 to 10.

(61) The following results were obtained:

(62) TABLE-US-00006 Example Example 25 24 (invention) Polymer of Example 4 20 g AM 20 g AM Pigmentary paste 8.6 g with 8.6 g with containing 40% by DC Red 7 DC Red 7 weight of pigment in isododecane Microcrystalline wax 15 g 15 g (Microwax HW from Paramelt) Hydrogenated 26 g 26 g polyisobutene (Parleam from Nippon Oil Fats) Isododecane qs 100 g qs 100 g 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 2 500; reference 481688 from Sigma) Microcrystalline wax 15 g (Microwax HW from Paramelt) Isododecane qs 100 g Evaluation of the film Appearance of the Homogeneous Homogeneous film film film Resistance to Yes Yes without deformation without damaging damaging the film the film Water resistance ++ +++ Olive oil resistance 0 +++ Sebum resistance 0 +++ Non-tacky + +++ Transfer-resistant 0 +++

(63) The results obtained show that the deposit resulting from the application of polymer 4 followed by 3-aminopropyl-terminated polydimethylsiloxane (Example 25) forms a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation, to water, to oil and to sebum, whereas the sole application of polymer 4 (Example 24) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

(64) Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film on contact with water, olive oil and sebum are markedly improved with the application of the top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane.

(65) The lipstick compositions of Example 25 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 staying power.

COMPARATIVE EXAMPLE 26

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(66) The two makeup compositions (foundation) of base coat containing the polymer of Example 1 and a top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane described below were prepared.

(67) The compositions were applied and the cosmetic properties of the film obtained were evaluated as described previously in Examples 5 to 10.

(68) The following results were obtained:

(69) TABLE-US-00007 Example 26 Example 9 (invention) Base Coat Polymer of Example 1 25 g AM 25 g AM Pigmentary paste 5 g with 5 g with red containing 40% by red iron iron oxide weight of pigment in oxide isododecane Disteardimonium 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane qs 100 g qs 100 g Top Coat 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 2 500; reference 481688 from Sigma) Isododecane qs 100 g Evaluation of the film Appearance of the Homogeneous Homogeneous film film film Resistance to Yes Yes without deformation without damaging damaging the film the film Water resistance ++ +++ Olive oil resistance 0 +++ Sebum resistance 0 +++ Non-tacky + +++ Transfer-resistant 0 +++

(70) The results obtained show that the deposit resulting from the application of polymer 1 followed by 3-aminopropyl-terminated polydimethylsiloxane (Example 26) forms a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation, to water, to oil and to sebum, whereas the sole application of polymer 1 (Example 9) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil and to sebum.

(71) Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film on contact with water, olive oil and sebum are markedly improved with the application of the top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane.

(72) The compositions of Example 26 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 staying power.

COMPARATIVE EXAMPLES 27 TO 33

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(73) The makeup composition (lipstick) of base coat containing the polymer of Example 2 and six top coat compositions containing an amine compound chosen from 3-aminopropyl-terminated polydimethylsiloxane (Mn=2500, 25 000 and 50 000), ethylenediamine, polyetherdiamine and bis-cetearyl amodimethicone described below were prepared.

(74) The compositions were applied and the cosmetic properties of the film obtained were evaluated as described previously in Examples 5 to 10.

(75) The glossy appearance of the film obtained was also evaluated in the same manner.

(76) The following results were obtained:

(77) TABLE-US-00008 Example Example Example Example Example Example Example 28 29 30 31 32 33 27 (invention) (invention) (invention) (invention) (invention) (invention) Base Coat Polymer of 20 g 20 g 20 g 20 g 20 g 20 g 20 g Example 2 AM AM AM AM AM AM AM Pigmentary 5 g with 5 g with 5 g with 5 g with 5 g with 5 g with 5 g with paste containing DC Red 7 DC Red 7 DC Red 7 DC Red 7 DC Red 7 DC Red 7 DC Red 7 40% by weight of pigment in isododecane Disteardimonium 10 g 10 g 10 g 10 g 10 g 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane qs 100 g qs 100 g qs 100 g qs 100 g qs 100 g qs 100 g qs 100 g Top Coat 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 2 500; reference 481688 from Sigma) 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 25 000; DMS A-31 from Gelest) 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 50 000; DMS-A35 from Gelest) Ethylenediamine 10 g Polyetherdiamine (1) 10 g Bis-cetearyl 10 g amodimethicone (2) Isododecane qs qs qs qs qs qs 100 g 100 g 100 g 100 g 100 g 100 g Evaluation of the film Appearance of the Homo- Homogeneous Homogeneous Homogeneous Homogeneous Homogeneous Homogeneous film geneous film film film film film film film Resistance to Yes Yes Yes Yes Yes but Yes Yes deformation without without without without film without without damaging damaging damaging damaging damaged damaging damaging the film the film the film the film the film the film Olive oil 0 +++ +++ +++ +++ +++ +++ resistance Non-tacky 0 +++ +++ ++ +++ ++ +++ Transfer- 0 +++ +++ +++ +++ ++ +++ resistant Gloss + +++ +++ +++ + + +++ (1) Jeffamine ED-900 Polyetheramine (Huntsman) (2) Silsoft AX (Momentive Performance Materials)

(78) The results obtained show that the deposit resulting from the application of polymer 2 followed by the amine compound (Examples 28 to 33) forms a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation and to oil, whereas the sole application of polymer 2 (Example 27) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil.

(79) Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film on contact with olive oil are markedly improved with the application of the top coat composition containing the amine compounds tested. It is also noted that the aminosilicone compounds also afford good gloss to the film obtained.

(80) The compositions of Examples 28 to 33 applied to the lips thus make it possible to obtain a non-tacky, transfer-resistant and oil-resistant makeup which thus has good staying power.

COMPARATIVE EXAMPLES 34 AND 35

Cosmetic Evaluation of Makeup Compositions with Application in Two Steps

(81) The makeup composition (lipstick) of base coat containing the polymer of Example 3 and a top coat composition containing a 3-aminopropyl-terminated polydimethylsiloxane (Mn 50 000) were prepared.

(82) The compositions were applied and the cosmetic properties of the film obtained were evaluated as described previously in Examples 5 to 10.

(83) The glossy appearance of the film obtained was also evaluated in the same manner.

(84) The following results were obtained:

(85) TABLE-US-00009 Example Example 35 34 (invention) Base Coat Polymer of Example 3 20 g AM 20 g AM Pigmentary paste 5 g with 5 g with DC containing 40% by DC Red 7 Red 7 weight of pigment in isododecane Isododecane qs 100 g qs 100 g Top Coat 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 50 000) Isododecane qs 100 g Evaluation of the film Appearance of the Homogeneous Homogeneous film film film Resistance to Yes Yes without deformation without damaging damaging the film the film Olive oil resistance 0 +++ Non-tacky + +++ Transfer-resistant 0 +++ Sheen + +++

(86) The results obtained show that the deposit resulting from the application of polymer 3 followed by 3-aminopropyl-terminated polydimethylsiloxane (Example 35) forms a non-tacky homogeneous film that does not transfer to the finger, and that is resistant to deformation and to oil, whereas the sole application of polymer 3 (Example 34) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to oil.

(87) Thus, the non-tacky and transfer-resistant aspect on contact with the finger, and also the resistance of the film on contact with olive oil are markedly improved with the application of the top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane.

(88) The lipstick compositions of Example 35 applied to the lips thus make it possible to obtain a non-tacky, transfer-resistant and oil-resistant makeup which thus has good staying power.