COMPOSITION COMPRISING POLYMER PARTICLES AND A MINERAL THICKENER, AND PROCESS USING THE SAME

Abstract

The present invention relates to a composition comprising particles of a polymer that is surface-stabilized with a stabilizer, the polymer of the particles being a C.sub.1-C.sub.4 alkyl (meth)acrylate polymer; the stabilizer being an isobornyl (meth)acrylate polymer chosen from isobornyl (meth)acrylate homopolymer and statistical copolymers of isobornyl (meth)acrylate and of C.sub.1-C.sub.4 alkyl (meth)acrylate present in an isobornyl (meth)acrylate/C.sub.1-C.sub.4 alkyl (meth)acrylate weight ratio of greater than 4, at least one hydrocarbon-based oil and at least one mineral thickener chosen from optionally modified clays and optionally modified silicas, or mixtures thereof. The invention also relates to a process for making up and/or caring for keratin materials, in which said composition is applied.

Claims

1. A composition, comprising: particles of at least one polymer that is surface-stabilized with a stabilizer; at least one hydrocarbon-based oil; and at least one mineral thickener selected from the group consisting of optionally modified clays, optionally modified silicas, and mixtures thereof, wherein the polymer of the particles comprises a C.sub.1-C.sub.4 alkyl (meth)acrylate polymer; the stabilizer comprises an isobornyl (meth)acrylate polymer selected from the group consisting of a isobornyl (meth)acrylate homopolymer and a statistical copolymer of isobornyl (meth)acrylate and of a C.sub.1-C.sub.4 alkyl (meth)acrylate, and an isobornyl (meth)acrylate/C.sub.1-C.sub.4 alkyl (meth)acrylate weight ratio is greater than 4.

2. The composition according to claim 1, wherein the polymer of the particles comprises at least one of methyl acrylate and ethyl acrylate polymer.

3. The composition according to claim 1, wherein the polymer of the particles comprises an ethylenically unsaturated acid monomer or the anhydride thereof.

4. The composition according to claim 1, wherein the polymer of the particles comprises from 80% to 100% by weight of a C.sub.1-C.sub.4 alkyl (meth)acrylate and from 0 to 20% by weight of an ethylenically unsaturated acid monomer, relative to the total weight of the polymer.

5. The composition according to claim 1, wherein the polymer of the particles is selected from the group consisting of: methyl acrylate homopolymers, ethyl acrylate homopolymers, methyl acrylate/ethyl acrylate copolymers, methyl acrylate/ethyl acrylate/acrylic acid copolymers, methyl acrylate/ethyl acrylate/maleic anhydride copolymers, methyl acrylate/acrylic acid copolymers, ethyl acrylate/acrylic acid copolymers, methyl acrylate/maleic anhydride copolymers, and ethyl acrylate/maleic anhydride copolymers.

6. The composition according to claim 1, wherein the stabilizer is a statistical copolymer of isobornyl (meth)acrylate and of C.sub.1-C.sub.4 alkyl (meth)acrylate in wherein an isobornyl (meth)acrylate/C.sub.1-C.sub.4 alkyl (meth)acrylate weight ratio is greater than or equal to 5.

7. The composition according to claim 1, wherein the stabilizer is selected from the group consisting of: isobornyl acrylate homopolymers, statistical copolymers of isobornyl acrylate/methyl acrylate, statistical copolymers of isobornyl acrylate/methyl acrylate/ethyl acrylate, and statistical copolymers of isobornyl methacrylate/methyl acrylate.

8. The composition according to claim 1, wherein the hydrocarbon-based oil is selected from the group consisting of apolar hydrocarbon-based oils.

9. The composition according to claim 1, wherein the content of hydrocarbon-based oil ranges from 20% to 75% by weight relative to the weight of the composition.

10. The composition according to claim 1, wherein the content of polymer particles surface-stabilized with a stabilizer, expressed as active material, represents from 5% to 55% by weight, expressed as polymer particle solids, relative to the weight of the composition.

11. The composition according to claim 1, further comprising a plasticizer selected from the group consisting of tri-n-butyl citrate, tripropylene glycol monomethyl ether and trimethyl pentaphenyl trisiloxane.

12. The composition according to claim 1, wherein the content of plasticizer represents from 1 to 50% by weight relative to the weight of the composition.

13. The composition according to claim 1, wherein the optionally modified clay is selected from the group consisting of modified hectorites, modified bentonites, and optionally modified silicas.

14. The composition according to claim 1, wherein the content of mineral thickener, expressed as active material, represents from 0.5% to 30% by weight relative to the weight of the composition.

15. The composition according to claim 13 wherein a content of the optionally modified clay, expressed as active material, ranges from 0.5% to 10% by weight relative to the weight of the composition.

16. The composition according to claim 13 comprising an optionally modified silica, wherein a content of the optionally modified silics, expressed as active material, is from 0.5% to 20% by weight relative to the weight of the composition.

17. The composition according to the preceding claim 16, wherein the composition is anhydrous.

18. A process for making up and/or caring for keratin materials, comprising applying the composition according to claim 1 to the keratin material.

19. The composition according to claim 8, wherein the apolar hydrocarbon-based oils comprise from 8 to 16 carbon atoms.

20. The composition according to claim 13, wherein the optionally modified clay is selected from the group consisting of disteardimonium hectorite, stearalkonium hectorite, quaternium-18 bentonite, stearalkonium bentonite and quaternium-18/benzalkonium bentonite

Description

EXAMPLES

Synthesis Examples

Example 1

[0234] In a first step, 1300 g of isododecane, 337 g of isobornyl acrylate, 28 g of methyl acrylate and 3.64 g of tert-butyl peroxy-2-ethylhexanoate (Trigonox 21S from Akzo) were placed in a reactor. The isobornyl acrylate/methyl acrylate mass ratio is 92/8. The mixture was heated at 90° C. under argon with stirring.

[0235] After 2 hours of reaction, 1430 g of isododecane were added to the reactor feedstock and the mixture was heated to 90° C.

[0236] In a second step, a mixture of 1376 g of methyl acrylate, 1376 g of isododecane and 13.75 g of Trigonox 21S were run in over 2 hours 30 minutes, and the mixture was left to react for 7 hours. 3.3 litres of isododecane were then added and part of the isododecane was evaporated off to obtain a solids content of 50% by weight.

[0237] A dispersion of methyl acrylate particles stabilized with a statistical copolymer stabilizer containing 92% isobornyl acrylate and 8% methyl acrylate in isododecane was obtained.

[0238] The oily dispersion contains in total (stabilizer+particles) 80% methyl acrylate and 20% isobornyl acrylate.

[0239] The polymer particles of the dispersion have a number-average size of about 160 nm.

[0240] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Example 2

[0241] A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

[0242] Step 1: 275.5 g of isobornyl acrylate, 11.6 g of methyl acrylate, 11.6 g of ethyl acrylate, 2.99 g of Trigonox 21, 750 g of isododecane; followed by addition, after reaction, of 750 g of isododecane.

[0243] Step 2: 539.5 g of methyl acrylate, 539.5 g of ethyl acrylate, 10.8 g of Trigonox 21S, 1079 g of isododecane. After reaction, addition of 2 litres of isododecane and evaporation to obtain a solids content of 35% by weight.

[0244] A dispersion in isododecane of methyl acrylate/ethyl acrylate (50/50) copolymer particles stabilized with an isobornyl acrylate/methyl acrylate/ethyl acrylate (92/4/4) statistical copolymer stabilizer was obtained.

[0245] The oily dispersion contains in total (stabilizer+particles) 40% methyl acrylate, 40% ethyl acrylate and 20% isobornyl acrylate.

[0246] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Example 3

[0247] A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

[0248] Step 1: 315.2 g of isobornyl acrylate, 12.5 g of methyl acrylate, 12.5 g of ethyl acrylate, 3.4 g of Trigonox 21, 540 g of isododecane, 360 g of ethyl acetate; followed by addition, after reaction, of 540 g of isododecane and 360 g of ethyl acetate.

[0249] Step 2: 303 g of methyl acrylate, 776 g of ethyl acrylate, 157 g of acrylic acid, 11 g of Trigonox 21S, 741.6 g of isododecane and 494.4 g of ethyl acetate. After reaction, addition of 3 litres of an isododecane/ethyl acetate mixture (60/40 weight/weight) and total evaporation of the ethyl acetate and partial evaporation of the isododecane to obtain a solids content of 44% by weight.

[0250] A dispersion in isododecane of methyl acrylate/ethyl acrylate/acrylic acid (24.5/62.8/12.7) copolymer particles stabilized with an isobornyl acrylate/methyl acrylate/ethyl acrylate (92/4/4) statistical copolymer stabilizer was obtained.

[0251] The oily dispersion contains in total (stabilizer+particles) 10% acrylic acid, 20% methyl acrylate, 50% ethyl acrylate and 20% isobornyl acrylate.

[0252] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Example 4

[0253] A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

[0254] Step 1: 315.2 g of isobornyl acrylate, 12.5 g of methyl acrylate, 12.5 g of ethyl acrylate, 3.4 g of Trigonox 21, 540 g of isododecane, 360 g of ethyl acetate; followed by addition, after reaction, of 540 g of isododecane and 360 g of ethyl acetate.

[0255] Step 2: 145 g of methyl acrylate, 934 g of ethyl acrylate, 157 g of acrylic acid, 12.36 g of Trigonox 21S, 741.6 g of isododecane and 494.4 g of ethyl acetate. After reaction, addition of 3 litres of an isododecane/ethyl acetate mixture (60/40 weight/weight) and total evaporation of the ethyl acetate and partial evaporation of the isododecane to obtain a solids content of 44% by weight.

[0256] A dispersion in isododecane of methyl acrylate/ethyl acrylate/acrylic acid (11.7/75.6/12.7) copolymer particles stabilized with an isobornyl acrylate/methyl acrylate/ethyl acrylate (92/4/4) statistical copolymer stabilizer was obtained.

[0257] The oily dispersion contains in total (stabilizer+particles) 10% acrylic acid, 10% methyl acrylate, 60% ethyl acrylate and 20% isobornyl acrylate.

[0258] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Example 5

[0259] A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

[0260] Step 1: 48 g of isobornyl acrylate, 2 g of methyl acrylate, 2 g of ethyl acrylate, 0.52 g of Trigonox 21, 57.6 g of isododecane, 38.4 g of ethyl acetate; followed by addition, after reaction, of 540 g of isododecane and 360 g of ethyl acetate.

[0261] Step 2: 98 g of methyl acrylate, 73 g of ethyl acrylate, 25 g of maleic anhydride, 1.96 g of Trigonox 21S, 50.4 g of isododecane and 33.60 g of ethyl acetate. After reaction, addition of 1 litre of an isododecane/ethyl acetate mixture (60/40 weight/weight) and total evaporation of the ethyl acetate and partial evaporation of the isododecane to obtain a solids content of 46.2% by weight.

[0262] A dispersion in isododecane of methyl acrylate/ethyl acrylate/maleic anhydride (50/37.2/12.8) copolymer particles stabilized with an isobornyl acrylate/methyl acrylate/ethyl acrylate (92/4/4) statistical copolymer stabilizer was obtained.

[0263] The oily dispersion contains in total (stabilizer+particles) 10% maleic anhydride, 30% methyl acrylate, 40% ethyl acrylate and 20% isobornyl acrylate.

[0264] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Example 6

[0265] A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

[0266] Step 1: 48.5 g of isobornyl methacrylate, 4 g of methyl acrylate, 0.52 g Trigonox 21, 115 g of isododecane; followed by addition, after reaction, of 80 g of isododecane.

[0267] Step 2: 190 g of methyl acrylate, 1.9 g of Trigonox 21S, 190 g of isododecane. After reaction, addition of 1 litre of isododecane and partial evaporation of the isododecane to obtain a solids content of 48% by weight.

[0268] A dispersion in isododecane of methyl acrylate polymer particles stabilized with an isobornyl methacrylate/methyl acrylate (92/8) statistical copolymer stabilizer was obtained.

[0269] The oily dispersion contains in total (stabilizer+particles) 80% methyl acrylate and 20% isobornyl methacrylate.

[0270] The dispersion is stable after storage for 7 days at room temperature (25° C.).

Examples 7 and 8 (Invention) and 9 and 10 (Outside the Invention)

[0271] Several oily dispersions of polymethyl acrylate stabilized with a stabilizer containing isobornyl acrylate and optionally methyl acrylate were prepared, according to the procedure of Example 1, by varying the mass ratio of isobornyl acrylate and methyl acrylate and observing the stability of the dispersion obtained as a function of the chemical constitution of the stabilizer.

[0272] All the dispersions comprise in total (stabilizer+particles) 80% methyl acrylate and 20% isobornyl acrylate.

Example 7

[0273] Step 1: 50 g of isobornyl acrylate, 0.5 g Trigonox 21, 96 g of isododecane; followed by addition, after reaction, of 80 g of isododecane.

[0274] Step 2: 200 g of methyl acrylate, 2 g of Trigonox 21S, 200 g of isododecane. After reaction, addition of 80 g of isododecane and evaporation to obtain a solids content of 31% by weight.

[0275] A dispersion in isododecane of polymethyl acrylate particles stabilized with a polyisobornyl acrylate stabilizer was obtained.

Example 8

[0276] Step 1: 48.5 g of isobornyl acrylate, 8.5 g of methyl acrylate, 0.57 g Trigonox 21, 115 g of isododecane; followed by addition, after reaction, of 75 g of isododecane.

[0277] Step 2: 185.5 g of methyl acrylate, 1.85 g of Trigonox 21S, 185.5 g of isododecane. After reaction, addition of 75 g of isododecane and evaporation to obtain a solids content of 31% by weight.

[0278] A dispersion in isododecane of polymethyl acrylate particles stabilized with an isobornyl acrylate/methyl acrylate (85/15) statistical copolymer stabilizer was obtained.

Example 9 (Outside the Invention)

[0279] Step 1: 48.5 g of isobornyl acrylate, 12 g of methyl acrylate, 0.6 g Trigonox 21, 115 g of isododecane; followed by addition, after reaction, of 60 g of isododecane.

[0280] Step 2: 182 g of methyl acrylate, 1.82 g of Trigonox 21S, 182 g of isododecane. After reaction, addition of 60 g of isododecane and evaporation to obtain a solids content of 31% by weight.

[0281] A dispersion in isododecane of polymethyl acrylate particles stabilized with an isobornyl acrylate/methyl acrylate (80/20) statistical copolymer stabilizer was obtained.

Example 10 (Outside the Invention)

[0282] Step 1: 48.5 g of isobornyl acrylate, 21 g of methyl acrylate, 0.7 g Trigonox 21, 130 g of isododecane; followed by addition, after reaction, of 65 g of isododecane.

[0283] Step 2: 173 g of methyl acrylate, 1.73 g of Trigonox 21S, 173 g of isododecane. After reaction, addition of 65 g of isododecane and evaporation to obtain a solids content of 31% by weight.

[0284] A dispersion in isododecane of polymethyl acrylate particles stabilized with an isobornyl acrylate/methyl acrylate (70/30) statistical copolymer stabilizer was obtained.

[0285] The stability 12 hours after the end of synthesis of the oily dispersions of polymethyl acrylate of Examples 1 and 7 to 10 was compared, and the following results were obtained.

TABLE-US-00001 Example Stabilizer Stability 1 92 isobornyl acrylate/ Stable 8 methyl acrylate 7 100 isobornyl acrylate Stable 8 85 isobornyl acrylate/ Stable 15 methyl acrylate 9 80 isobornyl acrylate/ Phase separation and 20 methyl acrylate setting to a solid 10 70 isobornyl acrylate/ Phase separation and 30 methyl acrylate setting to a solid

[0286] The results obtained show that the dispersions of polymethyl acrylate in isododecane are stable when the stabilizer is an isobornyl acrylate homopolymer or an isobornyl acrylate/methyl acrylate copolymer with an isobornyl acrylate/methyl acrylate weight ratio >80/20.

[0287] Moreover, the film obtained with the oily dispersions of Examples 1, 7 and 8 have the following properties:

TABLE-US-00002 Resistance to fatty Gloss at 20° substances Tacky 72 Resistant to fatty substances Non-tacky 69 Resistant to fatty substances Non-tacky 65 Resistant to fatty substances Non-tacky

Examples 11 and 12 (Outside the Invention)

[0288] Tests were performed with other monomers bearing a cyclic group by replacing the isobornyl acrylate, performing step 1 of Example 1, i.e. preparing a cyclic monomer/methyl acrylate (92/8) statistical copolymer stabilizer. All the stabilizers prepared in isododecane led to a medium that set to a solid in the form of a viscous precipitate. This shows that such stabilizers are unsuitable for forming an oily dispersion since they are incompatible with isododecane, in contrast with the stabilizers prepared in Examples 1 to 8 described previously.

TABLE-US-00003 Compatibility in Examples Stabilizer isododecane 11 Cyclohexyl acrylate/methyl acrylate Incompatible (92/8) (viscous precipitate) 12 Cyclohexyl methacrylate/methyl Incompatible acrylate (92/8) (viscous precipitate)

Examples 13: Mascara

[0289] The following compositions, the ingredients of which are given in the table below, are prepared. Compositions 1 to 3 are in accordance with the invention; compositions A and B are compositions outside the invention.

[0290] The amounts are indicated by weight of starting materials.

TABLE-US-00004 Ingredients 1 2 3 A B A Carnauba wax (Cerauba T1; 5 — — 5 — Baerlocher) Paraffin wax (Affine 56-58 10 — — 10 — Pastilles; Baerlocher) B Isododecane (Ineos) 54.5 72 37 72 42 Disteardimonium hectorite 2 4 4 4 — (Bentone 38 VCG; Elementis) Propylene carbonate (Huntsman) 0.5 1 1 1 — Copolymer (methyl acrylate)-co- 20 15 50 — 50 (isobornyl acrylate)) in isododecane (according to Example 1) C Iron oxide (Sunpuro C33-7001, 7 7 7 7  7 Sun) D Preserving agent 1 1 1 1  1

Protocol for Preparing the Compositions

Preparation of Phase a (Comprising the Waxes) for Compositions 1 and A

[0291] The waxes are melted in a heating pan (95-98° C.).

Preparation of Phase B

[0292] Phase B is prepared at 70° C. with stirring for 30 minutes using a Rayneri blender. For compositions 1 and A, after phase A has totally melted, phase B is poured into phase A with stirring for 30 minutes.

Addition of Phase C

[0293] Phase C is introduced into phase A+B for compositions 1 and A or into phase B for compositions 2, 3 and B.

[0294] Stirring is continued for 10 minutes.

[0295] The preparation is cooled to room temperature.

Addition of Phase D

[0296] Phase D is introduced at room temperature into the resulting mixture with stirring until a homogeneous preparation is obtained.

[0297] Each of the mascara compositions thus obtained is transferred into a closed container to prevent it from drying out on contact with air.

[0298] After 24 hours at room temperature, the satisfactory homogeneity and dispersion of the pigment are evaluated.

Evaluation of the Viscosity:

[0299] RM 100 Rheomat viscometer from Mettler (at 25° C. and 1.013×10.sup.5 Pa).

[0300] The texture is acceptable if the measured viscosity is greater than 4 Pa.Math.s.

Makeup-Removal Evaluation

[0301] Removal of makeup using cotton wool and a makeup-removing composition Bi-Facil from Lancôme. The makeup removal is acceptable if the mascara is removed as cohesive sheaths and does not leave any blackish marks on the cotton wool and around the eyes.

TABLE-US-00005 Compositions 1 2 3 A B Viscosity (Pa .Math. s) 14.5 17.5 19.6 13.2 1 makeup removal as as as black as sheath sheath sheath mark sheath

[0302] It is thus found that only the compositions according to the invention have a suitable texture and can be removed without leaving any black marks.

[0303] The same results are obtained by replacing the dispersion of copolymer of Example 1 with the same amount as that of Example 4.

Examples 14: Mascara

[0304] The following compositions, the ingredients of which are given in the table below, are prepared. Compositions 4 and 5 are in accordance with the invention; composition C is a composition outside the invention.

[0305] The amounts are indicated as weight of starting materials.

TABLE-US-00006 Ingredients 4 5 C A Carnauba wax (Cerauba T1; Baerlocher) 5 — — Paraffin wax (Affine 56-58 Pastilles; Baerlocher) 10 — — B Isododecane (Ineos) 52 27 42 Silica silylate (Aerogel VM-2270; Dow Corning) 5 15 — Copolymer (methyl acrylate)-co-(isobornyl 20 50 50 acrylate)) in isododecane (according to Example 1) C Iron oxide (Sunpuro C33-7001, Sun) 7 7 7 D Preserving agent 1 1 1

Protocol for Preparing the Compositions

Preparation of Phase A of Composition 4

[0306] The waxes are melted in a heating pan (95-98° C.).

Preparation of Phase B

[0307] Phase B is prepared at 70° C. with stirring for 30 minutes using a Rayneri blender. For composition 4, after phase A has totally melted, phase B is poured into phase A with stirring for 30 minutes.

Addition of Phase C

[0308] Phase C is introduced into phase A+B for composition 4 or into phase B for compositions 5 and C.

[0309] Stirring is continued for 10 minutes.

[0310] The preparation is cooled to room temperature.

Addition of Phase D

[0311] Phase D is introduced at room temperature into the resulting mixture with stirring until a homogeneous preparation is obtained.

[0312] Each of the mascara compositions thus obtained is transferred into a closed container to prevent it from drying out on contact with air.

[0313] After 24 hours at room temperature, the satisfactory homogeneity and dispersion of the pigment are evaluated.

Results:

[0314] The viscosity and the makeup removal were evaluated under the conditions detailed in the preceding mascara example.

TABLE-US-00007 Compositions 4 5 C Viscosity (Pa .Math. s) 16.6 12.1 1 makeup removal as as as sheath sheath sheath

[0315] Tests 4 and 5 are repeated, replacing the dispersion of copolymer of Example 1 with the same amount as that of Example 4, and give the same results.

Examples 15: Foundation

[0316] The following compositions, the ingredients of which are given in the table below, are prepared.

[0317] Composition 6 is in accordance with the invention; composition D is outside the invention.

[0318] The amounts are indicated as weight of starting materials.

TABLE-US-00008 Ingredients 6 D Copolymer (methyl acrylate)-co-(isobornyl acrylate)) 51.16 — in isododecane (according to Example 1) Polypropylsilsesquioxane in isododecane (Dow — 34.99 Corning 680 ID Fluid; Dow Corning) (75% AM) Iron oxides (and) disodium stearoyl glutamate (and) 1.58 1.58 aluminium hydroxide, (yellow) from Miyoshi Kasei Iron oxides (and) disodium stearoyl glutamate (and) 0.41 0.41 aluminium hydroxide, (red) from Miyoshi Kasei Iron oxides (and) disodium stearoyl glutamate (and) 0.15 0.15 aluminium hydroxide, (black) from Miyoshi Kasei Titanium dioxide (and) disodium stearoyl glutamate 8.66 8.66 (and) aluminium hydroxide, (white) from Miyoshi Kasei Mica (Synafil S 1050 from Eckart) 1.20 1.20 Disteardimonium hectorite (Bentone Gel ISD V, with 30 30 propylene carbonate, isododecane; 10% active material) Isododecane 6.84 23.01

Protocol for Preparing the Compositions:

[0319] The required amounts of copolymer are first mixed with the isododecane, with stirring using a Rayneri blender, at room temperature.

[0320] Once the mixture has been homogenized, the pigments are added with stirring and this mixture is homogenized for 10 minutes.

[0321] The mixture comprising the disteardimonium hectorite is finally added and the whole is mixed until a homogeneous composition is obtained.

Evaluation of the Compositions and Results:

[0322] The composition according to the invention is much thicker than the comparative composition.

[0323] They are both stable at 24 hours at room temperature and after 4 weeks at room temperature.

[0324] The composition according to the invention does not leave any transfer marks, when dry or in the presence of sebum.

[0325] In the case of the comparative composition, it is not possible to perform the tests under the normal conditions: the specimens are tacky and the comparative composition consequently leaves many marks.

Examples 16: Lipsticks

[0326] The following compositions, the ingredients of which are collated in the table below, are prepared.

[0327] The amounts are indicated as weight of starting materials, unless otherwise indicated.

TABLE-US-00009 7 8 9 10 Copolymer (methyl acrylate)-co-(ethyl acrylate)- 60 60 70 60 co-(isobornyl acrylate) in isododecane according to Example 2 Disteardimonium hectorite (Bentone Gel ISD V, 0 0.5 0 1 with propylene carbonate, isododecane; Elementis) (amount expressed as active material) Silica silylate (Aerogel VM-2270; Dow 1.4 2.6 3.8 3.8 Corning) Trimethyl siloxysilicate (SR1000 from 5 5 5 5 Momentive Performance Materials) C30-45 Alkyldimethylsilyl 2.5 0.5 2.5 2.5 polypropylsilsesquioxane (Dow Corning SW- 8005 C30 Resin Wax from Dow Corning) Tributyl citrate 0 0 0 1 Red 7 pigment 4.8 4.8 4.8 4.8 Isododecane qs qs qs qs

Protocol for Preparing the Compositions

[0328] The polymer dispersion is mixed with the mineral thickener in a heating pan and the mixture is homogenized at room temperature using a Rayneri blender.

[0329] The silicone resin (trimethyl siloxysilicate) is then added, followed by the wax predissolved at 60° C. in part of the isododecane.

[0330] A mixture of the pigment with part of the isododecane and the plasticizer (tributyl citrate), when it is present in the formula, is prepared separately by treating in a three-roll machine, and is added to the preceding mixture.

[0331] The mixture is homogenized with the Rayneri blender for 20 minutes, so as to obtain a smooth, homogeneous mixture.

[0332] The composition is completed by adding the amount of isododecane evaporated during the manufacture.

Evaluation of the Compositions:

Oil Resistance Test:

[0333] The composition is applied to a Bioskin skin sample (25 μm thickness of the wet film).

[0334] The sample is left to dry for 24 hours at 35° C.

[0335] After the drying step, a drop of olive oil is placed on the film of composition and left for 10 minutes.

[0336] The oil is then wiped five times using cotton wool.

[0337] The integrity of the film after wiping with the cotton wool is observed to evaluate the oil resistance of the composition, on a scale ranging from 1 to 3 (1: excellent resistance, 2: intermediate resistance, and 3: poor resistance).

Results:

[0338] The compositions according to the invention apply easily and homogeneously, as a non-tacky deposit. Moreover, the compositions according to the invention all show excellent oil resistance.

Examples 17: Lipsticks

[0339] The following compositions, the ingredients of which are collated in the table below, are prepared.

[0340] The amounts are indicated as weight of starting materials, unless otherwise indicated.

TABLE-US-00010 11 12 13 Copolymer (methyl acrylate)-co-(ethyl acrylate)-co- 64.7 64.7 — (acrylic acid)-co-(isobornyl acrylate) in isododecane according to Example 4 Copolymer (methyl acrylate)-co-(ethyl acrylate)-co- — — 70 (acrylic acid)-co-(acrylic acid)-co-(isobornyl acrylate) in isododecane according to Example 3 Disteardimonium hectorite (Bentone Gel ISD V, with 1.5 — — propylene carbonate, isododecane; Elementis) (% active material) Silica silylate (Aerogel VM-2270; Dow Corning) — 3.81 3.81 Trimethyl siloxysilicate (SR1000 from Momentive — 2.5 2.5 Performance Materials) C30-45 Alkyldimethylsilyl polypropylsilsesquioxane 0.6 2.5 2.5 (Dow Corning SW-8005 C30 Resin Wax from Dow Corning) Tributyl citrate 2.8 2.8 2.9 Red 7 pigment 1 1 Isododecane qs qs qs

[0341] The preparation protocol is similar to that of the preceding example.

Evaluation of the Compositions

Oil Resistance Test:

[0342] The test was detailed in the preceding example.

Transfer Test

[0343] The composition is applied to a Bioskin skin sample (25 μm thickness of the wet film).

[0344] The sample is left to dry for 24 hours at 35° C.

[0345] After the drying step, a piece of adhesive tape is applied to the film of composition and removed at an angle of 180°.

[0346] The integrity of the film is observed after removing the adhesive tape and the transfer resistance is evaluated on a scale ranging from 1 to 3 (1: no peeling, 2: partial peeling, and 3: total peeling).

TABLE-US-00011 11 12 13 Transfer test 1 1 1 Oil resistance 1 1 1