Composition comprising polymer particles, a hydrocarbon-based oil and a silicone elastomer, and process using the same

Abstract

The present invention relates to a composition comprising particles of at least one 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 silicone elastomer conveyed in at least one second oil. 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 silicone elastomer conveyed in at least one second oil, wherein the polymer of the particles is a C.sub.1-C.sub.4 alkyl (meth)acrylate polymer, and the stabilizer is an isobornyl (meth)acrylate polymer is selected from the group consisting of 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.

2. The composition according to claim 1, wherein the polymer of the particles is a methyl acrylate and/or 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 C.sub.1-C.sub.4 alkyl (meth)acrylate and from 0 to 20% by weight of 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 present in an isobornyl (meth)acrylate/C.sub.1-C.sub.4 alkyl (meth)acrylate weight ratio of 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 30% 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, wherein the second oil is a hydrocarbon based oil.

12. The composition according to claim 11, wherein the second oil is selected from the group consisting of volatile apolar hydrocarbon-based oils.

13. The composition according to claim 1, wherein the silicone elastomer is an emulsifying silicone elastomer.

14. The composition according to claim 1, comprising a content of silicone elastomer, expressed as active material, ranging from 1% to 12.5% by weight relative to the weight of the composition.

15. The composition according to claim 1, wherein the polymer particles surface-stabilized with a stabilizer are incorporated into the composition in the form of a dispersion in at least one hydrocarbon-based oil.

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

Description

SYNTHESIS EXAMPLES

Example 1

(1) 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.

(2) After 2 hours of reaction, 1430 g of isododecane were added to the reactor feedstock and the mixture was heated to 90 C.

(3) 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 liters of isododecane were then added and part of the isododecane was evaporated off to obtain a solids content of 50% by weight.

(4) A dispersion of methyl acrylate particles stabilized with a statistical copolymer stabilizer containing 92% isobornyl acrylate and 8% methyl acrylate in isododecane was obtained.

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

(6) The polymer particles of the dispersion have a number-average size of about 160 nm.

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

Example 2

(8) A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

(9) 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.

(10) 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 liters of isododecane and evaporation to obtain a solids content of 35% by weight.

(11) 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.

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

(13) The dispersion is stable after storage for 7 days at room temperature (25 C.).

Example 3

(14) A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

(15) 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.

(16) 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 liters 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.

(17) 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.

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

(19) The dispersion is stable after storage for 7 days at room temperature (25 C.).

Example 4

(20) A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

(21) 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.

(22) 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 liters 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.

(23) 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.

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

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

Example 5

(26) A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

(27) 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.

(28) 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 liter 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.

(29) 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.

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

(31) The dispersion is stable after storage for 7 days at room temperature (25 C.).

Example 6

(32) A dispersion of polymer in isododecane was prepared according to the preparation method of Example 1, using:

(33) 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.

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

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

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

(37) The dispersion is stable after storage for 7 days at room temperature (25 C.).

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

(38) 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.

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

Example 7 (Invention)

(40) 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.

(41) 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.

(42) A dispersion in isododecane of polymethyl acrylate particles stabilized with a polyisobornyl acrylate stabilizer was obtained.

Example 8 (Invention)

(43) 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.

(44) 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.

(45) 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)

(46) 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.

(47) 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.

(48) 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)

(49) 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.

(50) 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.

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

(52) 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.

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

(54) 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.

Examples 11 (Foundation)

(55) The following compositions, the ingredients of which are given in the table below, are prepared.

(56) The amounts are indicated as weight of starting materials.

(57) TABLE-US-00002 Amounts Ingredients % in weight (Methyl acrylate)-co-(isobornyl acrylate) copolymer in 50 isododecane (according to Example 1) Silicone elastomer: PEG-15/Lauryl dimethicone 20 crosspolymer (at 25% by weight in isododecane; KSG 320 from Shin-Etsu) Iron oxides (and) disodium stearoyl glutamate (and) 1.58 aluminium hydroxide, (yellow) from Miyoshi Kasei Iron oxides (and) disodium stearoyl glutamate (and) 0.41 aluminium hydroxide, (red) from Miyoshi Kasei Iron oxides (and) disodium stearoyl glutamate (and) 0.15 aluminium hydroxide, (black) from Miyoshi Kasei Titanium dioxide (and) disodium stearoyl glutamate (and) 8.66 aluminium hydroxide, (white) from Miyoshi Kasei Mica (Synafil S 1050 from Eckart) 1.20 Isododecane qs

(58) Protocol for Preparing Said Compositions

(59) The desired amount of polymer particle dispersion according to Synthesis Example 1 is weighed out, and the pigments are then added and the whole is homogenized (Rayneri blender, room temperature, 10 minutes).

(60) The isododecane is then added, followed by the silicone elastomer (KSG-320) and the whole is homogenized for a further 10 minutes.

(61) Evaluation of the Composition:

(62) Tack Evaluation

(63) The degree of tack on drying is evaluated in vivo: a dab (0.05 g) of formula is placed on the skin of the forearm, the formula is spread uniformly with the fingers, during the drying of the foundation, the person evaluating the composition touches the deposit of formula on the skin every 5 seconds to evaluate the degree of tack.
Results

(64) A composition whose texture is fluid and which applies very easily with good glidance is obtained; the application time is short.

(65) The deposit is very light and is not tacky during or after drying. It is homogeneous, matt and very soft.

(66) No composition transfer marks are observed when the skin is rubbed with a paper handkerchief, when dry or in the presence of sebum.

Examples 12, 13 and 14: Lipsticks

(67) The following compositions, the ingredients of which are collated in the table below, are prepared. The amounts are indicated as weight of starting materials, unless otherwise indicated.

(68) TABLE-US-00003 Ingredient 12 13 14 Silica silylate (Aerogel VM-2270; Dow 1 Corning) Red 7 1 1 1 (Methyl acrylate)-co-(ethyl acrylate)-co- 58 58 58 (isobornyl acrylate) copolymer in isododecane according to Example 2 C30-45 Alkyldimethylsilyl 0.59 0.59 0.59 polypropylsilsesquioxane (Dow Corning SW- 8005 C30 Resin Wax from Dow Corning) Silicone elastomer: PEG-15/lauryl 20 30 30 dimethicone crosspolymer (at 25% by weight in isododecane; KSG 320 from Shin-Etsu) Isododecane 20.41 10.41 9.41
Protocol for Preparing Said Compositions

(69) The pigment is ground in part of the isododecane three times with a three-roll mill so as to obtain a homogeneous, viscous paste.

(70) The silicone wax is predissolved in part of the isododecane while hot so as to obtain a smooth, homogeneous mixture.

(71) The stabilized polymer particle dispersion, the silica aerogel, the predissolved silicone wax, the silicone elastomer and the remaining amount of isododecane are placed in a heating pan.

(72) The whole is heated until a homogeneous mixture is obtained, and the pigmentary paste is finally added with stirring.

(73) If necessary, the isododecane is topped up to compensate for the evaporation.

(74) Evaluation of the Compositions:

(75) Oil Resistance Test:

(76) The composition is applied to a Bioskin skin sample (25 m thickness of the wet film).

(77) The sample is left to dry for 24 hours at 35 C.

(78) After the drying step, a drop of olive oil is placed on the film of composition and left for 10 minutes.

(79) The oil is then wiped five times using cotton wool.

(80) The integrity of the film after wiping with the cotton wool is evaluated 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).

(81) Transfer Test:

(82) The composition is applied to a Bioskin skin sample (25 m thickness of the wet film).

(83) The sample is left to dry for 24 hours at 35 C.

(84) After the drying step, a piece of adhesive tape is applied to the film of composition and removed at an angle of 180.

(85) The integrity of the film after removing the adhesive tape is evaluated on a scale ranging from 1 to 3 (1: intact film, 2: intermediate peeling, and 3: total peeling).

(86) Results:

(87) The compositions according to the invention are stable. They are easy to apply and leave a non-tacky, comfortable deposit (no impression of tautness or of drying-out), which shows very good oil resistance without any transfer.