Phosphonic ethylenic polymer and cosmetic uses thereof

Abstract

The invention relates to a cosmetic process for caring for or making up keratin materials, comprising the topical application to the keratin materials of a cosmetic composition comprising a phosphonic polymer derived from the polymerization of: (a) 45% to 95% by weight of ethylenic monomer bearing an at least C.sub.8 linear or branched alkyl group; (b) 5% to 25% by weight of vinylphosphonic acid monomer; (c) 0 to 50% by weight of additional monomer chosen from linear or branched C.sub.1C.sub.6 alkyl (meth)acrylates, C.sub.6-C.sub.12 cycloalkyl (meth)acrylates, and polydimethylsiloxanes bearing a mono(meth)acryloyloxy end group, optionally combined with an additional compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups, aminosilanes, salts of divalent or trivalent metal ions, clays and metal oxides. 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. The invention also relates to polymers containing the three monomers (a), (b) and (c).

Claims

1. A cosmetic process for treating keratin materials, comprising the topical application to the keratin materials of a composition comprising, in a physiologically acceptable medium, a phosphonic polymer 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 C.sub.8 linear or branched alkyl group; (b) 5% to 25% by weight of vinylphosphonic acid monomer of formula (I); (c) 0% to 50% by weight of additional monomer chosen from: (i) 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; (ii) polydimethylsiloxane silicone monomers bearing a mono(meth)acryloyloxy end group of formula (II) below: ##STR00008## 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; n denotes an integer ranging from 1 to 300; said vinylphosphonic acid monomer of formula (I) being: ##STR00009## in which: R1 denotes H or —CH.sub.3; X denotes a covalent bond and n denotes an integer ranging from 0 to 14; or X denotes a —COO— group and n denotes an integer ranging from 2 to 6.

2. The process according to claim 1, wherein the ethylenic monomer bearing an at least C.sub.8 linear or branched alkyl group is chosen from: a) linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates; b) the (meth)acrylamides of formula CH.sub.2═C(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) the vinyl esters of formula R.sub.5—CO—O—CH═CH.sub.2 in which R.sub.5 represents a linear or branched C.sub.8-C.sub.22 alkyl group; d) the ethers of formula R.sub.6—O—CH═CH.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 an at least C.sub.8 linear or branched alkyl group is chosen from linear or branched C.sub.8-C.sub.22 alkyl (meth)acrylates.

4. The process according to claim 1, wherein ethylenic monomer bearing an at least C.sub.8 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 an at least C.sub.8 linear or branched alkyl group is present in said phosphonic polymer in a content ranging from 55% to 95% by weight, relative to the total weight of monomers.

6. The process according to claim 1, wherein, for the monomer (I), X denotes a covalent bond and n is an integer ranging from 0 to 6 or X denotes a —COO— group and n is an integer ranging from 2 to 4.

7. The process according to claim 1, wherein for monomer (I), R1=H and X denotes a covalent bond and n is an integer ranging from 0 to 4.

8. The process according to claim 1, wherein monomer (I) is chosen from: vinylphosphonic acid; 3-butenylphosphonic acid; 4-pentenylphosphonic acid; 10-undecenylphosphonic acid; 11-dodecenylphosphonic acid; 2-phosphonoethyl ester of 2-methyl-2-propenoic acid; and 2-phosphonoethyl ester of 2-propenoic acid.

9. 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.

10. The process according to claim 1, wherein for said silicone monomer of formula (II): 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; n denotes an integer ranging from 3 to 200.

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

12. The process according to claim 1, wherein said phosphonic polymer does not contain any additional monomer (c).

13. The process according to claim 1, wherein said phosphonic 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 vinylphosphonic acid monomer (I).

14. The process according to claim 1, wherein said phosphonic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/vinylphosphonic acid stearyl acrylate/vinylphosphonic acid 2-ethylhexyl acrylate/stearyl acrylate/vinylphosphonic acid.

15. The process according to claim 1, wherein said phosphonic 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 vinylphosphonic acid monomer (I); (c) 0.5% to 50% by weight of C.sub.6-C.sub.12 cycloalkyl (meth)acrylate.

16. The process according to claim 1, wherein the phosphonic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/vinylphosphonic acid/isobornyl (meth)acrylate stearyl acrylate/vinylphosphonic acid/isobornyl (meth)acrylate 2-ethylhexyl acrylate/stearyl acrylate/vinylphosphonic acid/isobornyl (meth)acrylate.

17. The process according to claim 1, wherein the phosphonic 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 vinylphosphonic acid monomer (I); (c) 0.5% to 50% by weight of silicone monomer (II).

18. The process according to claim 1, wherein the phosphonic polymer is chosen from the following copolymers: 2-ethylhexyl acrylate/vinylphosphonic acid/silicone monomer (II) stearyl acrylate/vinylphosphonic acid/silicone monomer (II) 2-ethylhexyl acrylate/stearyl acrylate/vinylphosphonic acid/silicone monomer (II).

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

20. The process according to claim 1, wherein: either a composition derived from the mixing of a composition comprising the phosphonic polymer and of an additional component, or a composition containing same and comprising a physiologically acceptable medium, is applied topically to keratin materials, the composition derived from the mixing being anhydrous when the additional component is an amino alkoxysilane; or a composition comprising the phosphonic polymer and an additional component or a composition containing same and comprising a physiologically acceptable medium are applied sequentially to keratin materials, the additional component being chosen from: (i) an amine compound chosen from polyamine compounds bearing several primary amine and/or secondary amine groups and amino alkoxysilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, the compositions used being anhydrous when the additional component is an amino alkoxysilane.

21. The process according to claim 20, wherein the polyamine compound comprises from 2 to 20 carbon atoms.

22. The process according to claim 20, wherein the polyamine 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-propylenedimaine, 1,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine and spermidine.

23. The process according to claim 20, wherein the amino alkoxysilane is of formula (III):
R′.sub.1Si(OR′.sub.2).sub.z(R′.sub.3).sub.x  (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 R=C.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 possibly 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.

24. The process according to claim 20, wherein the polyamine compound is chosen from amine-based polymers.

25. The process according to claim 24, wherein the polyamine compound is an amine-based polymer chosen from poly((C.sub.2-C.sub.5)alkyleneimines; poly(allylamine); 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): ##STR00010## 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): ##STR00011## 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 group containing from 2 to 8 carbon atoms, x and y are integers ranging from 1 to 5000; polyetherdiamines; polytetrahydrofuran (or polytetramethylene glycol) α,ω-diamines and polybutadiene α,ω-diamines; polyamidoamine dendrimers bearing amine end functions; and poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine side functions.

26. The process according to claim 20, wherein the additional component is an amine compound chosen from polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains and 3-aminopropyltriethoxysilane.

27. The process according to claim 20, wherein the amine compound is used in a mole ratio of amine group of the amine compound/phosphonic acid of the polymer ranging from 0.01 to 10.

28. The process according to claim 20, wherein when the composition used contains an amino alkoxysilane, it comprises a C.sub.2-C.sub.5 monoalcohol.

29. The process according to claim 20, wherein the additional component is a clay chosen from clays of the smectite family, of the kaolinite family, optionally modified clays of the halloysite, dombassite, antigorite, benthierine, pyrophyllite, montmorillonite, beidellite, vermiculite, talc, stevensite, hectorite, bentonite, saponite, chlorite, sepiolite and illite family.

30. The process according to claim 20, wherein the additional component is a salt of divalent or trivalent metal ions chosen from salts of ions derived from Al(III), Ca(II), Cu(II), Fe(II), Fe(III), Mg(II), Mn(II), Zn(II) and mixtures thereof.

31. The process according to claim 20, wherein the additional component is a metal oxide chosen from titanium dioxide, iron oxides, zirconium oxides, zinc oxides, cerium oxides and chromium oxides.

32. The process according to claim 20, wherein the mixing of the composition comprising the phosphonic polymer and the additional component, or of the composition containing same, is performed in a time of between 1 minute and 24 hours before its application to keratin materials.

33. The process according to claim 1, wherein the composition applied to the keratin materials comprises a hydrocarbon-based oil.

Description

EXAMPLE 1

2-Ethylhexyl Acrylate/Vinylphosphonic Acid Copolymer (90/10 Mass Composition) Polymer 1

(1) 180 g of 2-ethylhexyl acrylate and 20 g of vinylphosphonic acid were placed in a jacketed 1-litre reactor equipped with a stirring anchor, followed by addition of 300 g of isododecane. The system was sparged with argon for 10 minutes, and 3 g of initiator tert-butyl peroxy-2-ethylhexanoate (Trigonox® 21S from AkzoNobel) were then added. The heating of the jacket was set at 90° C. for 7 hours at 150 rpm.

(2) The medium was then diluted with 300 g of isododecane, and then concentrated by distillation to remove the unreacted monomers. A solution containing 50% by weight of the polymer in isododecane was finally obtained.

(3) The polymer obtained has a number-average molecular weight (Mn) of 6800 and a weight-average molecular weight (Mw) of 138 000.

EXAMPLE 2

2-Ethylhexyl Acrylate/Isobornyl Acrylate/Vinylphosphonic Acid Copolymer (70/20/10 Mass Composition) Polymer 2

(4) The polymer was prepared according to the procedure of Example 1, using 140 g of 2-ethylhexyl acrylate, 40 g of isobornyl acrylate and 20 g of vinylphosphonic acid. A solution containing 50% by weight of the polymer in isododecane was finally obtained.

(5) The polymer obtained has a number-average molecular weight (Mn) of 4800 and a weight-average molecular weight (Mw) of 10 000.

EXAMPLES 3 AND 4

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(6) The makeup compositions (lip gloss) described below containing the polymer of Example 1 with or without 3-aminopropyl-terminated polydimethylsiloxane 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 μm, which was left to dry at room temperature (25° C.) for 24 hours.

(7) The state of the film obtained was then observed.

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

(9) 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).

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

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

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

(13) ++: moderately efficient evaluated cosmetic property

(14) +: sparingly efficient evaluated cosmetic property

(15) 0: inefficient evaluated cosmetic property

(16) The following results were obtained:

(17) TABLE-US-00001 Example 3 Example 4 Composition Polymer of 25 g AM 25 g AM Example 1 Pigmentary paste 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 weight of pigment in isododecane 3-Aminopropyl- — 2.5 g terminated polydimethylsiloxane (Mn 2500; reference 481688 from Sigma) Isododecane 70 g 67.5 g Evaluation of the film Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil resistance 0 + Sebum resistance 0 + Non-tacky 0 + Transfer-resistant 0 +

(18) The results obtained show that the deposit resulting from the application of polymer 1 alone (Example 3) forms a homogeneous film, which is not fragmented after mechanical stress, but the film is tacky, transfers onto the finger and is not resistant to contact with olive oil and sebum.

(19) The deposit resulting from the application of polymer 1 mixed with the 3-aminopropyl-terminated polydimethylsiloxane (Example 4) forms a homogeneous film, which is not fragmented after mechanical stress, and shows an improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with olive oil and sebum, compared with the film of Example 3.

(20) Thus, the addition of the 3-aminopropyl-terminated polydimethylsiloxane contributes toward improving the cosmetic properties of the film obtained.

(21) The lipstick composition of Example 4 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 persistence.

EXAMPLES 5 AND 6

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(22) The makeup compositions (lip gloss) described below containing the polymer of Example 2 with or without disteardimonium hectorite were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(23) The following results were obtained:

(24) TABLE-US-00002 Example 5 Example 6 Composition Polymer of 25 g AM 25 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 weight of pigment in isododecane Disteardimonium — 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane 70 g 60 g Evaluation of the film Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil resistance 0 ++ Sebum resistance 0 ++ Non-tacky 0 ++ Transfer-resistant 0 ++

(25) The results obtained show that the deposit resulting from the application of polymer 2 alone (Example 5) forms a homogeneous film, which is not fragmented after mechanical stress, but the film is tacky, transfers onto the finger and is not resistant to contact with olive oil and sebum.

(26) The deposit resulting from the application of polymer 2 mixed with disteardimonium hectorite (Example 6) forms a homogeneous film, which is not fragmented after mechanical stress, and shows good improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with water, olive oil and sebum, compared with the film of Example 5.

(27) Thus, the addition of disteardimonium hectorite contributes toward improving the cosmetic properties of the film obtained.

(28) The lipstick composition of Example 6 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 persistence.

EXAMPLE 7

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(29) The makeup compositions (lip gloss) described below containing the polymer of Example 2 with or without 3-aminopropyl-terminated polydimethylsiloxane were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(30) The following results were obtained:

(31) TABLE-US-00003 Example 5 Example 7 Composition Polymer of 25 g AM 25 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 weight of pigment in isododecane 3-Aminopropyl- — 2.5 g terminated polydimethylsiloxane (Mn 2500; reference 481688 from Sigma) Isododecane 70 g 67.5 g Evaluation of the film Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil resistance 0 +++ Sebum resistance 0 +++ Non-tacky 0 ++ Transfer-resistant 0 +++

(32) The deposit resulting from the application of polymer 2 mixed with 3-aminopropyl-terminated polydimethylsiloxane (Example 7) forms a homogeneous film, which is not fragmented after mechanical stress, and shows good improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with water, olive oil and sebum, compared with the film of Example 5.

(33) Thus, the addition of the 3-aminopropyl-terminated polydimethylsiloxane contributes toward improving the cosmetic properties of the film obtained.

(34) The lipstick composition of Example 7 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 persistence.

EXAMPLES 8 AND 9

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(35) The makeup compositions described below containing the polymer of Example 2 with or without 3-aminopropyl-terminated polydimethylsiloxane and containing 2-octyldodecanol (nonvolatile oil) were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(36) The following results were obtained:

(37) TABLE-US-00004 Example 8 Example 9 Composition Polymer of 25 g AM 25 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 weight of pigment in isododecane 3-Aminopropyl- — 2.5 g terminated polydimethylsiloxane (Mn 2500; reference 481688 from Sigma) 2-Octyldodecanol 20 g 20 g Isododecane 50 g 37.5 g Evaluation of the film Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil resistance 0 + Sebum resistance 0 + Non-tacky 0 + Transfer-resistant 0 +

(38) The results obtained show that the deposit resulting from the application of polymer 2 alone and of 2-octyldodecanol (Example 8) forms a homogeneous film, which is not fragmented after mechanical stress, but the film is tacky, transfers onto the finger and is not resistant to contact with olive oil and sebum.

(39) The deposit resulting from the application of polymer 1 and 2-octyldodecanol mixed with the 3-aminopropyl-terminated polydimethylsiloxane (Example 9) forms a homogeneous film, which is not fragmented after mechanical stress, and shows an improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with water, olive oil and sebum, compared with the film of Example 8.

(40) Thus, the addition of the 3-aminopropyl-terminated polydimethylsiloxane contributes toward improving the cosmetic properties of the film obtained.

EXAMPLES 10 AND 11

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(41) The makeup compositions described below containing the polymer of Example 2 with or without red iron oxides were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(42) The following results were obtained:

(43) TABLE-US-00005 Example 10 Example 11 Composition Polymer of 25 g AM 25 g AM Example 2 Pigmentary paste — 5 g containing 40% by weight of red iron oxide in isododecane Isododecane 75 g 70 g Evaluation of the film Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Olive oil resistance 0 +++ Sebum resistance 0 +++ Non-tacky 0 +++ Transfer-resistant 0 +++

(44) The results obtained show that the deposit resulting from the application of polymer 2 alone (Example 10) forms a homogeneous film, which is not fragmented after mechanical stress, but the film is tacky, transfers onto the finger and is not resistant to contact with olive oil and sebum.

(45) The deposit resulting from the application of polymer 2 mixed with red iron oxide (Example 11) forms a homogeneous film, which is not fragmented after mechanical stress, and shows a large improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with olive oil and sebum, compared with the film of Example 10.

(46) Thus, the addition of red iron oxide contributes toward improving the cosmetic properties of the film obtained.

EXAMPLES 12 AND 13

Cosmetic Evaluation of Makeup Composition with Application in Two Steps

(47) The two base coat makeup compositions (lip gloss) containing the polymer of Example 2 and a top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane described below were prepared.

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

(49) The top coat composition was then applied onto the dry base coat deposit by producing a deposit with a wet thickness of 100 μm, which was left to dry at room temperature (25° C.) for 24 hours.

(50) The cosmetic properties of the film obtained before (outside the invention) and after (invention) applying the top coat composition were evaluated according to the protocols described in the preceding Examples 3 and 4.

(51) The following results were obtained:

(52) TABLE-US-00006 Example 12 Example 13 Base Coat Polymer of Example 2 25 g 25 g Pigmentary paste 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 weight of pigment in isododecane Disteardimonium 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) Isododecane qs 100 g qs 100 g Top Coat No Yes 3-Aminopropyl- 10 g terminated polydimethylsiloxane (Mn 2 500; reference 481688 from Sigma) Isododecane 90 g Appearance Homogeneous Homogeneous of the film film film Resistance to Yes without Yes without deformation damaging the damaging the film film Water resistance ++ +++ Olive oil resistance 0 ++ Sebum resistance 0 ++ Non-tacky 0 ++ Transfer-resistant 0 ++

(53) The results obtained show that the deposit resulting from the application of polymer 2 followed by the 3-aminopropyl-terminated polydimethylsiloxane (Example 13) forms a non-tacky homogeneous film that does not transfer by finger, and that is resistant to water, to oil and to sebum, whereas the sole application of polymer 2 (Example 12) forms a deposit that is much more tacky and that transfers onto the finger and has poor resistance to water, to oil and to sebum.

(54) 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 top coat composition containing 3-aminopropyl-terminated polydimethylsiloxane.

(55) The lipstick compositions of Example 13 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.

EXAMPLES 14 AND 15

Cosmetic Evaluation of Makeup Compositions with Application in One Step

(56) The makeup compositions described below containing the polymer of Example 2 with or without 3-aminopropyltriethoxysiloxane (APTES) and with or without 2-octyldodecanol (nonvolatile oil) were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(57) The following results were obtained:

(58) TABLE-US-00007 Example 5 Example 14 Example 15 Composition Polymer of 25 g AM 25 g AM 25 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 Red 7 weight of pigment in isododecane APTES — 2.5 g 2.5 g 2-Octyldodecanol — — 20 g Isododecane 70 g 67.5 g 47.5 g Evaluation of the film Appearance Homogeneous Homogeneous Homogeneous of the film film film film Resistance to Yes without Yes without Yes without deformation damaging the damaging the damaging the film film film Water resistance ++ +++ +++ Olive oil resistance 0 +++ ++ Sebum resistance 0 +++ ++ Non-tacky 0 ++ + Transfer-resistant 0 +++ +

(59) The deposit resulting from the application of polymer 2 mixed with APTES (Examples 14, 15) forms a homogeneous film, which is not fragmented after mechanical stress, and shows good improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with water, olive oil and sebum, compared with the film of Example 5.

(60) Thus, the addition of APTES contributes toward improving the cosmetic properties of the film obtained.

EXAMPLES 16 AND 17

(61) The makeup compositions (lip gloss) described below containing the polymer of Example 2 with or without calcium stearate or zinc acetate were prepared, and the cosmetic properties were then evaluated according to the protocols described in the preceding Examples 3 and 4.

(62) The following results were obtained:

(63) TABLE-US-00008 Example 5 Example 16 Example 17 Composition Polymer of 25 g AM 25 g AM 25 g AM Example 2 Pigmentary paste 5 g with DC 5 g with DC 5 g with DC containing 40% by Red 7 Red 7 Red 7 weight of pigment in isododecane Calcium stearate 3.75 g Zinc acetate — 3.75 g Isododecane qs 100 g qs 100 g qs 100 g Evaluation of the film Appearance Homogeneous Homogeneous Homogeneous of the film film film film Resistance to Yes without Yes without Yes without deformation damaging the damaging the damaging the film film film Olive oil resistance 0 ++ +++ Sebum resistance 0 ++ +++ Non-tacky 0 +++ +++ Transfer-resistant 0 ++ +++

(64) The results obtained show that the deposit resulting from the application of polymer 2 alone (Example 5) forms a homogeneous film, which is not fragmented after mechanical stress, but the film is tacky, transfers onto the finger and is not resistant to contact with olive oil and sebum.

(65) The deposits resulting from the application of polymer 2 mixed with calcium stearate (Example 16) or zinc acetate (Example 17) form a homogeneous film, which is not fragmented after mechanical stress, and show good improvement in the non-tacky and transfer-resistance properties and in the resistance of the film to contact with olive oil and sebum, compared with the film of Example 5.

(66) Thus, the addition of calcium stearate or zinc acetate contributes toward improving the cosmetic properties of the film obtained.

(67) The lipstick compositions of Examples 16 and 17 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 persistence.