PHOSPHONIC COPOLYMER AND USE THEREOF IN THE COSMETICS FIELD

Abstract

The invention relates to a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer; (iii) 0 to 20% by weight of an additional monomer.

The invention also relates to a cosmetic composition comprising the copolymer and to a cosmetic process for caring for or making up keratin materials, comprising the topical application of the composition to the keratin materials.

It also relates to the use of the copolymer as a skin-tensioning agent.

Claims

1. A copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##STR00006## 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; (iii) 0 to 20% by weight of an additional monomer.

2. The copolymer as claimed in claim 1, wherein, for 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.

3. The copolymer as claimed in claim 1, wherein, for monomer (I), R1=H and X denotes a covalent bond and n is an integer ranging from 0 to 4.

4. The copolymer as claimed 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; 2-phosphonoethyl ester of 2-propenoic acid; and preferably vinylphosphonic acid.

5. The copolymer as claimed claim 1, wherein the additional monomer is a monomer of formula (II): ##STR00007## in which: R.sub.1 denotes a hydrogen atom or a methyl radical; X denotes O or NH or NR.sub.3; R.sub.2 denotes a linear C.sub.1-C.sub.22 or branched C.sub.3-C.sub.10 or cyclic C.sub.5-C.sub.7 alkyl radical, or a linear C.sub.3-C.sub.20 or branched C.sub.6-C.sub.20 or cyclic C.sub.5-C.sub.7 unsaturated hydrocarbon-based radical, or an —(Si(CH.sub.3).sub.2 O).sub.b—CH.sub.3 radical, with b ranging from 5 to 70, it being understood that X=O when R.sub.2 is a radical of formula —(Si(CH.sub.3).sub.2 O).sub.b—CH.sub.3; R.sub.3 denotes a linear C.sub.1-C.sub.12 or branched C.sub.3-C.sub.12 alkyl radical.

6. The copolymer as claimed in claim 1, wherein it results from the polymerization of: 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; 5% to 30% by weight of vinylphosphonic acid; and preferably of: 75% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; 5% to 25% by weight of vinylphosphonic acid.

7. The copolymer as claimed in claim 1, which is chosen from 80/20 or 90/10 (weight/weight) isobornyl acrylate/vinylphosphonic acid copolymers.

8. A composition comprising, in a physiologically acceptable medium, a copolymer as claimed claim 1.

9. The composition as claimed in claim 8, wherein the copolymer is present in a content ranging from 0.1% to 10% by weight, relative to the total weight of the composition, preferably from 0.5% to 10% by weight of active material, preferentially ranging from 1% to 8% by weight, and more preferentially ranging from 1% to 6% by weight.

10. A process for caring for or making up keratin materials, comprising the topical application to the keratin materials of a composition as claimed in claim 8.

11. The process as claimed in claim 10, wherein the topical application, to keratin materials, of an extemporaneous mixture of a composition comprising, in a physiologically acceptable medium, a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##STR00008## 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; (iii) 0 to 20% by weight of an additional monomer and of an additional component chosen from: (i) an amine compound chosen from amine compounds bearing several primary amine and/or secondary amine groups and aminosilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, or of a composition containing same and comprising a physiologically acceptable medium, is carried out.

12. The process as claimed in claim 10, which comprises the sequential application, to keratin materials, of a composition comprising, in a physiologically acceptable medium, a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##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; (iii) 0 to 20% by weight of an additional monomer and of an additional component chosen from: (i) an amine compound chosen from amine compounds comprising several primary amine and/or secondary amine groups and aminosilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, or of a composition containing same and comprising a physiologically acceptable medium, is carried out.

13. The process as claimed in claim 11, wherein the amine compound comprises from 2 to 20 carbon atoms.

14. The process as claimed in claim 11, 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; and the aminosilanes 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.

15. The process as claimed in claim 11, wherein the amine compound is chosen from amine-based polymers, in particular having a weight-average molecular weight ranging from 500 to 1 000 000.

16. The process as claimed in claim 15 the amine compound is an amine-based polymer chosen from poly((C.sub.2-C.sub.5)alkyleneimines), and in particular polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine)s; poly(allylamine); polyvinylamines and copolymers thereof, in particular with vinylamides; vinylamine/vinylformamide copolymers; polyamino acids bearing NH.sub.2 groups, such as polylysine; aminodextran; amino polyvinyl alcohol, acrylamidopropylamine-based copolymers; chitosans; polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains ##STR00010## ##STR00011## polyetherdiamines; polytetrahydrofuran (or polytetramethylene glycol) α,ω-diamines and polybutadiene α,ω-diamines; polyamidoamine dendrimers bearing amine end functions; poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine side functions.

17. The process as claimed in claim 11, wherein the amine compound is used according to an amine compound/phosphonic acid mole ratio ranging from 0.01 to 10.

18. The process as claimed in claim 11, 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.

19. The process as claimed in 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.

20. The process as claimed in claim 11, wherein the additional component is a metal oxide chosen from titanium dioxide, iron oxides, zirconium oxides, zinc oxides, cerium oxides and chromium oxides.

21. The process as claimed in claim 11, wherein an extemporaneous mixture prepared less than 5 minutes before application to keratin materials of a composition comprising, in a physiologically acceptable medium, a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##STR00012## 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; (iii) 0 to 20% by weight of an additional monomer and of said additional component, or of a composition containing same and comprising a physiologically acceptable medium, is applied to keratin materials.

22. The process as claimed in claim 12, wherein a composition comprising, in a physiologically acceptable medium, a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##STR00013## 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; (iii) 0 to 20% by weight of an additional monomer is first applied to keratin materials, in particular to the skin, then said additional component or a composition containing same and comprising a physiologically acceptable medium is applied.

23. The process as claimed in claim 12, wherein said additional component, or a composition containing same and comprising a physiologically acceptable medium, is first applied to keratin materials, in particular to the skin, then a composition comprising, in a physiologically acceptable medium, a copolymer resulting from the polymerization of: (i) 70% to 95% by weight, of the total weight of the monomers, of isobornyl (meth)acrylate; (ii) 1% to 30% by weight of vinylphosphonic acid monomer of formula (I): ##STR00014## 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, (iii) 0 to 20% by weight of an additional monomer is applied.

24. The process as claimed in claim 10 the composition comprises an oil.

25. The process as claimed in claim 10, intended for caring for the skin.

26. The process as claimed in claim 10, wherein it is intended for attenuating wrinkles.

27. The cosmetic use, as a skin tensioning agent, in particular a wrinkled-skin tensioning agent, of a phosphonic polymer as defined in claim 1 and optionally as a mixture with an additional compound chosen from: (i) an amine compound chosen from amine compounds bearing several primary amine and/or secondary amine groups and aminosilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, or of a composition containing same.

28. A composition obtained by mixing a composition as claimed in claim 8 and an additional component chosen from: (i) an amine compound chosen from amine compounds bearing several primary amine and/or secondary amine groups and aminosilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, or a composition containing same and comprising a physiologically acceptable medium.

29. A kit comprising a first composition as claimed in claim 8 and a second composition comprising an additional compound chosen from: (i) an amine compound chosen from amine compounds bearing several primary amine and/or secondary amine groups and aminosilanes, (ii) salts of divalent or trivalent metal ions, (iii) clays, (iv) metal oxides, or of a composition containing same and comprising a physiologically acceptable medium, the first and second compositions each being packaged in a separate packaging assembly.

Description

EXAMPLE 1

Isobornyl Acrylate/Vinylphosphonic Acid Copolymer (90/10 by Weight)

[0149] 180 g of isobornyl acrylate, 20 g of vinylphosphonic acid and 200 g of an isododecane/ethanol (70/30 weight/weight) mixture were introduced into a reactor. The reaction medium was degassed under argon for 20 minutes. Then, 2 g of 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane initiator (Trigonox® T141 from Akzo Nobel) were added. The reaction medium was heated at reflux of the ethanol for 24 hours with stirring. After cooling to ambient temperature (25° C.), the reaction medium was diluted with 300 g of isododecane.

[0150] The product obtained was precipitated from ethanol, recovered and dried in an oven at 60° C. under vacuum.

[0151] 180 g (90% yield) of a white powder were obtained after drying.

[0152] Molecular weight Mw=55 700.

[0153] The acid number is 21 mg/g.

EXAMPLE 2

Isobornyl Acrylate/Vinylphosphonic Acid Copolymer (80/20 by Weight)

[0154] The copolymer was prepared according to the procedure from example 1 using 160 g of isobornyl acrylate and 40 g of vinylphosphonic acid.

[0155] 175 g (87.5% yield) of a white powder were obtained.

[0156] Molecular weight Mw=67 500.

[0157] The acid number is 31 mg/g.

EXAMPLE 3 (OUTSIDE THE INVENTION)

Isobornyl Acrylate/Acrylic Acid Copolymer (90/10 by Weight)

[0158] The copolymer was prepared according to the procedure from example 1 using 180 g of isobornyl acrylate and 20 g of acrylic acid.

[0159] 140 g (70% yield) of a white powder were obtained.

[0160] The acid number is 18 mg/g.

EXAMPLE 4 (OUTSIDE THE INVENTION)

Isobornyl Acrylate/Acrylic Acid Copolymer (80/20 by Weight)

[0161] The copolymer was prepared according to the procedure from example 1 using 160 g of isobornyl acrylate and 40 g of acrylic acid.

[0162] 150 g (75% yield) of a white powder were obtained.

[0163] The acid number is 110 mg/g.

EXAMPLE 5

Demonstration of the Tensioning Effect of the Polymers Used According to the Invention

[0164] This test consists in comparing, in vitro, the tensioning capacity of the polymer to be evaluated, relative to a reference tensioning polymer: Hybridur® 875 polymer dispersion from Air Products (aqueous dispersion at 40% by weight of particles of an interpenetrated network of polyurethane and acrylic polymers). The polymer to be evaluated is deposited on a nitrile rubber strip cut from a glove sold under the reference Safeskin Nitrile Criticial No. 038846 by the company Dominique Dutscher SA, having a surface area of 3.5 cm.sup.2, stretched taut beforehand on a support. A solution containing the polymer to be evaluated is therefore deposited on the elastomer strip, by depositing 1.8 mg (in solids) of polymer. 26 μl of an aqueous solution containing 7% AM of Hybridur® 875 polymer are thus placed on a nitrile rubber strip so as thus to obtain a reference tensioning strip, and 26 μl of a solution containing 7% AM of phosphonic polymer to be evaluated in an isododecane/ethanol mixture (70/30 weight/weight) are placed on another strip.

[0165] After drying for 24 hours at ambient temperature (25° C.), the curving (retraction) of the strip treated with the phosphonic polymer is observed in comparison with that obtained with the control (Hybridur® 875).

[0166] Also evaluated was the tensioning effect of the grafted polymer in the presence of 3-aminopropyltriethoxysilane (APTES) or of O,O′-Bis(2-aminopropyl) polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol (Jeffamine® ED-600 from Huntsman) or of PDMS diamine (DMS-A15 from Gelest).

[0167] For the 3-aminopropyltriethoxysilane (APTES), the following mixtures were prepared before application to the nitrile strip (the phosphonic polymer being in solution in the isododecane/ethanol mixture):

TABLE-US-00001 Degree Amount of Number of of neu- polymer of moles of Amount Number trali- example 1 phosphonic of APTES of moles Ex zation (in g) acid (in mg) of amines 1a 25% 0.7 2.625 × 10.sup.−4 7.26 3.2813 × 10.sup.−5 1b 50% 0.7 2.625 × 10.sup.−4 14.52 6.5625 × 10.sup.−5 1c 100%  0.7 2.625 × 10.sup.−4 29.05 13.125 × 10.sup.−5

TABLE-US-00002 Degree Amount of Number of of neu- polymer of moles of Amount Number trali- example 2 phosphonic of APTES of moles Ex zation (in g) acid (in mg) of amines 2a  25% 0.7 4.125 × 10.sup.−4 11.41 5.1563 × 10.sup.−5 2b  50% 0.7 4.125 × 10.sup.−4 22.82 10.3125 × 10.sup.−5  2c 100% 0.7 4.125 × 10.sup.−4 45.64 20.625 × 10.sup.−5 2d 200% 0.7 4.125 × 10.sup.−4 91.28  41.25 × 10.sup.−5

[0168] For the O,O′-Bis(2-aminopropyl) polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol (Jeffamine® ED-600 from Huntsman), the following mixtures were prepared before application to the nitrile strip (the phosphonic polymer being in solution in the isododecane/ethanol mixture):

TABLE-US-00003 Degree Amount of Number of Amount of of neu- polymer of moles of Jeffamine ® Number trali- example 1 phosphonic ED-600 of moles ex zation (in g) acid (in mg) of amines 1e  25% 0.7  2.625 .Math. 10.sup.−4 10 3.2813 × 10.sup.−5 1f 100% 0.7 2.625 × 10.sup.−4 40 13.125 × 10.sup.−5

[0169] For the PDMS diamine (DMS-A15 from Gelest), the following mixtures were prepared before application to the nitrile strip (the phosphonic polymer being in solution in the isododecane/ethanol mixture):

TABLE-US-00004 Degree Amount of Number of Amount of neu- polymer of moles of of PDMS Number trali- example 1 phosphonic diamine of moles ex zation (in g) acid (in mg) of amines 1g 25% 0.7  2.625 .Math. 10.sup.−4 41 3.2813 × 10.sup.−5 1h 50% 0.7 2.625 × 10.sup.−4 82 6.5625 × 10.sup.−5 1i 100%  0.7 2.625 × 10.sup.−4 164 13.125 × 10.sup.−5

[0170] The mixtures prepared were deposited (26 μl) on the nitrile rubber strips.

[0171] The tensioning effect obtained was measured according to the protocol previously described.

[0172] The water resistance of the tensioning effect was then evaluated by immersing the rubber strips treated with the polymer to be evaluated in water at ambient temperature (25° C.) for 10 minutes.

[0173] The following results were obtained:

TABLE-US-00005 Tensioning effect Polymer tested Tensioning effect after immersion in water Hybridure 875 correct correct reference Example 1 same as reference same as reference Example 1a greater than the greater than the reference reference Example 1b same as reference same as reference Example 1c same as reference same as reference Example 2 same as reference same as reference Example 2a same as reference greater than the reference Example 2b same as reference greater than the reference Example 2c greater than the greater than the reference reference Example 2d greater than the greater than the reference reference Example 1e less than the less than the reference but reference but tensioning effect tensioning effect observed observed Example 1f less than the less than the reference but reference but tensioning effect tensioning effect observed observed Example 1g less than the same as reference reference but tensioning effect observed Example 1h same as reference same as reference Example 1i Same as reference same as reference

[0174] The results obtained show that the phosphonic polymers of examples 1 and 2 alone or mixed with the amine compounds have a good tensioning effect, even after immersion in water: the tensioning effect is persistent with respect to water.

EXAMPLE 6 (COMPARATIVE)

[0175] The quality of the films obtained, with the polymers from examples 1 and 2 according to the invention and also with the polymers from examples 3 and 4 outside the invention, was evaluated.

[0176] The polymers were placed in solution at 7% AM in a (70/30) mixture of isododecane/ethanol. 26 μl of the polymer solution were applied to a nitrile rubber strip (as described in the previous example) and the appearance of the film obtained was observed after drying in the open air for 24 hours at ambient temperature.

[0177] Polymers 1 and 2 according to the invention form homogeneous transparent films, while polymers 3 and 4 outside the invention form films which are white (non-transparent) and non-homogeneous (crumbly film).

EXAMPLE 7

[0178] An anti-wrinkle gel having the following composition is prepared:

TABLE-US-00006 polymer of example 1 7 g disteardimonium hectorite/propylene carbonate in isododecane 3 g (bentone gel ® ISDV from Elementis) Preservatives qs Isododecane/ethanol (80/20 w/w) qs 100 g 

[0179] A similar composition was also prepared using the polymer of example 2.

[0180] The composition obtained, applied to the face, makes it possible to effectively smooth out wrinkles.

EXAMPLE 8

[0181] An anti-wrinkle gel having the following composition is prepared:

TABLE-US-00007 polymer of example 1 7 g disteardimonium hectorite/propylene carbonate in isododecane 3 g (bentone gel ® ISDV from Elementis) Preservatives qs Isododecane/ethanol (80/20 w/w) qs 100 g 

[0182] Just before application to the skin, 145.2 mg of 3-aminopropyltriethoxysilane (APTES) are added to the gel.

[0183] The composition obtained, as a mixture with APTES, applied to the face, makes it possible to effectively smooth out the wrinkles.

EXAMPLE 9

[0184] An anti-wrinkle gel having the following composition is prepared:

TABLE-US-00008 polymer of example 2 7 g disteardimonium hectorite/propylene carbonate in isododecane 3 g (bentone gel ® ISDV from Elementis) Preservatives qs Isododecane/ethanol (80/20 w/w) qs 100 g 

[0185] Just before application to the skin, 228.2 mg of 3-aminopropyltriethoxysilane (APTES) are added to the gel.

[0186] The composition obtained, as a mixture with APTES, applied to the face, makes it possible to effectively smooth out the wrinkles.

EXAMPLE 10

[0187] An anti-wrinkle gel having the following composition is prepared:

TABLE-US-00009 polymer of example 1 7 g disteardimonium hectorite/propylene carbonate in isododecane 3 g (bentone gel ® ISDV from Elementis) Preservatives qs Isododecane/ethanol (80/20 w/w) qs 100 g 

[0188] Just before application to the skin, 820 mg of PDMS diamine (DMS-A15 from Gelest) are added to the gel.

[0189] The composition obtained, as a mixture with PDMS diamine, applied to the face makes it possible to effectively smooth out the wrinkles.

EXAMPLE 11

[0190] An anti-wrinkle gel having the following composition is prepared:

TABLE-US-00010 polymer of example 2 7 g disteardimonium hectorite/propylene carbonate in isododecane 3 g (bentone gel ® ISDV from Elementis) Preservatives qs Isododecane/ethanol (80/20 w/w) qs 100 g 

[0191] The composition is applied to the wrinkled skin of the face. It is left to dry for 1 hour.

[0192] The following solution is then applied to the area of the skin treated:

TABLE-US-00011 3-aminopropyltriethoxysilane (APTES) 145.2 mg Isododecane/ethanol (80/20 w/w) qs 100 g
and it is left to dry for 1 hour.

[0193] The sequential application of the 2 compositions to the face makes it possible to effectively smooth out the wrinkles.

EXAMPLES 12 TO 14

[0194] The 3 compositions described below were prepared.

[0195] Each 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 ambient temperature (25° C.) for 24 hours.

[0196] The state of the film obtained was then observed.

[0197] The resistance of the film obtained was evaluated by separately applying 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.

[0198] The tackiness of the film and its capacity for transferring or not transferring on touching the film with a finger were also evaluated.

[0199] The following results were obtained:

TABLE-US-00012 Example 12 Example 13 Example 14 Polymer of 25 g   25 g  25 g example 1 PDMS diamine 0 3.75 g 7.5 g (DMS-A15 from Gelest) Isododecane:ethanol qs 100 g qs 100 g qs 100 g (70/30 w/w) Appearance Homogeneous Homogeneous Homogeneous of the film film film film Olive oil resistance + +++ +++ Sebum resistance + +++ +++ Non-tacky +++ +++ +++ Transfer-resistant +++ +++ +++

[0200] The results obtained show that polymer 1 alone or in the presence of PDMS diamine forms a homogeneous film which is non-tacky and does not transfer to the finger. The resistance of the film on contact with olive oil and sebum is much improved in the presence of PDMS diamine.

EXAMPLES 15 TO 18

[0201] The 4 compositions described below were prepared.

[0202] The film-forming properties were then evaluated according to the protocols described in examples 12 to 14.

[0203] The following results were obtained:

TABLE-US-00013 Ex 15 Ex 16 Ex 17 Ex 18 Polymer of 25 g 25 g 25 g   25 g example 1 PDMS diamine 0    3.75 3.75 g (DMS-A15 from Gelest) pigmentary — —  5 g   5 g paste containing 40% by weight of iron oxide in isododecane 2-Octyldodecanol 20 g 20 20   20 g Isododecane qs 100 g qs 100 g qs 100 g qs 100 g Appearance Homoge- Homoge- Homoge- Homoge- of the film neous film neous film neous film neous film Olive oil + +++ +++ +++ resistance Sebum + +++ +++ +++ resistance Non-tacky + +++ + +++ Transfer- +++ +++ +++ +++ resistant

[0204] The results obtained show that polymer 1 alone (ex 15) or in the presence of PDMS diamine (ex 16) and formulated with 2-octyldodecanol (nonvolatile oil) forms a homogeneous film which is non-tacky and does not transfer to the finger. The resistance of the film on contact with olive oil and sebum is much improved in the presence of PDMS diamine.

[0205] When iron oxide is added, an improvement in the resistance to olive oil and to sebum is noted (examples 17 and 18 in comparison with example 15).

EXAMPLE 19

[0206] The foundation composition described below was prepared.

[0207] The film-forming properties were then evaluated according to the protocols described in examples 12 to 14.

[0208] The following results were obtained:

TABLE-US-00014 Example 19 Polymer of 25 g example 1 pigmentary paste  5 g containing 40% by weight of iron oxide in isododecane Disteardimonium 10 g Hectorite (Bentone Gel ISD V from Elementis) 2-Octyldodecanol 20 g Isododecane: qs 100 g Appearance Homogeneous of the film film Olive oil resistance +++ Sebum resistance +++ Non-tacky +++ Transfer-resistant +++

[0209] The results obtained show that the foundation composition forms a homogeneous film which is non-tacky and does not transfer to the finger. The film obtained also exhibits good resistance on contact with olive oil and sebum, much improved in the presence of the bentone compared with the polymer alone (example 15).

[0210] The foundation applied to the skin of the face thus makes it possible to obtain a non-tacky, transfer-resistant and sebum-resistant makeup which therefore exhibits a good wear property.