Cosmetic composition comprising a defined silicone polymer and a surfactant

• US 20060013843A1
• Filed: 07/15/2005
• Published: 01/19/2006
• Est. Priority Date: 07/16/2004
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Blin, Xavier, Shimizu, Momoko
• Application Number:
  US11/181,949
• Publication Number:
  US 20060013843A1
• Time in Patent Office: Days
• US Class Current: 424/401
• CPC Class Codes: A61K 2800/31 Anhydrous
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61Q 1/06 Lipsticks

Abstract

The present invention relates to anhydrous cosmetic compositions of enhanced staying power, comprising, in a physiologically acceptable medium, at least one silicone polymer of defined general formula and a surfactant.

Claims

1. An anhydrous cosmetic composition, comprising, in a physiologically acceptable medium, at least one silicone polymer of general formula (I):

R¹_aR²_bR³_cSiO_(4-a-b-c)/2 

 

(I)

in which;

a is selected from 1 to 2.5, and

b and c, independently of one another, are selected from 0.001 to 1.5,

R¹, which is identical or different at each occurrence, is selected from;

C₁ to C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms, amino and/or carboxyl groups,

aryl and aralkyl radicals, and

radicals of general formula (II);

—

C_dH_2d—

O—

(C₂H₄O)_e(C₃H₆O)_fR⁴ 

 

(II)

 

with;

R⁴ being a C₁ to C₃₀ hydrocarbon radical or a radical R⁵—

(CO)—

, with R⁵ being a C₁ to C₃₀ hydrocarbon radical,

d is an integer selected from 0 to 15, and

e and f, independently of one another, are integers selected from 0 to 50,

and combinations thereof,

R² is a radical represented by the general formula (III);

-Q-O—

X 

 

(III)

 

with;

Q being a divalent C₂ to C₂₀ hydrocarbon radical which can include at least one ether bond and/or at least one ester bond, and

X being a polyhydroxylated hydrocarbon radical,

R³ is an organosiloxane group of general formula (IV);

 

with;

the radicals R each representing, independently of one another, a radical selected from C₁ to C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms; and

aryl and aralkyl radicals,

g is an integer selected from 1 to 5, and

h is an integer selected from 0 to 500, and at least one surfactant.

3. The cosmetic composition claim 1, wherein the surfactant is selected from the group consisting of oxyethylenated glycerol ethers, oxypropylenated glycerol ethers, oxyethylenated fatty alcohol ethers, oxypropylenated fatty alcohol ethers, fatty acid esters of polyethylene glycol, dimethicone copolyol, dimethicone copolyol benzoate, EO/PO polycondensates, the esters and ethers of saccharides, fatty acid esters of polyol, oxyethylenated myristyl alcohol containing 15 ethylene oxide groups, oxyethylenated polyglyceryl-2 monoisostearate containing 5 ethylene oxide groups, polyglyceryl-3 diisostearate, glyceryl monoisostearate, polyglyceryl-2 monoisostearate, polyglyceryl-3 isostearate, polyglyceryl-4 isostearate, polyglyceryl-6 monoisostearate, polyglyceryl-10 monoisostearate, polyglyceryl-2 monooleate, sorbitan isostearate, sorbitan monooleate, oxyethylenated sorbitan monooleate containing 5 ethylene oxide groups, dimethicone copolyol, dimethicone copolyol benzoate, polyoxyalkylenated silicone elastomers, a cyclomethicone/dimethicone copolyol mixture, and mixtures thereof.

4. The cosmetic composition of claim 1, wherein the surfactant is a silicone surfactant selected from the group consisting of

dimethicone copolyol,

dimethicone copolyol benzoate,

polyoxyalkylenated silicone elastomers,

a cyclomethicone/dimethicone copolyol mixture,

and mixtures thereof

5. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C¹ to C₁₀ alkyl radical.

6. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C₁ to C₆, alkyl radical.

7. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C₁ to C₄ alkyl radical.

8. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04, and

R¹ is a C₁ to C₁₀ alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5,

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

9. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04, and

R¹ is a C₁ to C6 alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5,

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

10. The cosmetic composition of claim 1, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04, and

R¹ is a C₁ to C₄ alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5,

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

11. The cosmetic composition according to claim 10, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04, and

R¹ is a methyl radical,

R² is represented by the formula (IIIA) in which n is selected from 1 to 5, and

R³ is represented by the formula (IVA) in which n is selected from 3 to 9.

12. The cosmetic composition of claim 1, further comprising at least one oil selected from the group consisting of hydrogenated polyisobutene, stearyl heptanoate, isononyl isononanoate, dipentaerythritol tetrahydroxystearate, tetraisostearate, 2-octyldodecanol, isotridecyl isononanoate, diisostearyl malate, and mixtures thereof.

13. The cosmetic composition of claim 1, further comprising a silicone oil selected from the group consisting of linear silicone oils and cyclic silicone oils.

14. The cosmetic composition of claim 1, further comprising a silicone oil selected from the group consisting of linear or cyclic silicone oils having a viscosity ≦

8 centistokes (8×

10<sup>−

6</sup> m²/s), octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyl-octyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes containing alkyl or alkoxy groups each having 2 to 24 carbon atoms, phenyl silicones, phenyltrimethicones, phenyldimethicones, phenyltrimethyl-siloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyltrisiloxanes, and 2-phenylethyl trimethylsiloxysilicates.

15. The cosmetic composition of claim 1, further comprising a volatile oil present at less than 15% by weight relative to a total weight of the cosmetic composition.

16. The cosmetic composition according to claim 15, wherein the volatile oil is selected from the group consisting of hydrocarbon oils having 8 to 16 carbon atoms, C₈-C₁₆ branched alkanes, isododecane, isodecane, isohexadecane, linear or cyclic silicone oils, linear or cyclic silicone oils having a viscosity ≦

8 centistokes (8·

10<sup>−

6</sup> m²/s), octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexa-siloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, fluorinated solvents, nonafluoromethoxybutane, perfluoromethylcyclopentane, and mixtures thereof.

17. The cosmetic composition of claim 1, wherein the cosmetic composition is in cast form.

18. The cosmetic composition of claim 1, further comprising at least one colorant.

19. The cosmetic composition of claim 1, further comprising at least one compound selected from the group consisting of waxes, pasty fatty substances, and mixtures thereof.

20. The cosmetic composition of claim 1, further comprising at least one filler.

21. The cosmetic composition of claim 1, wherein the cosmetic composition is selected from the group consisting of a skin care or make-up composition and a lip care or make-up composition.

23. The cosmetic composition of claim 1, wherein the cosmetic composition is a lipstick.

39. A method of making up and/or caring for at least one keratin material, comprising applying the cosmetic composition of claim 1 to the at least one keratin material.

40. The method of claim 39, wherein the at least one keratin material is selected from the group consisting of epidermal derivatives, mucosae, keratin fibers, skin, lips, nails, eyes, eyeslashes, and hair.

2. A cosmetic composition, comprising, in a physiologically acceptable medium, at least one silicone polymer of general formula (I):

R¹_aR²_bR³_cSiO_(4-a-b-c)/2 

 

(I)

in which;

a is selected from 1 to 2.5, and

b and c, independently of one another, are selected from 0.001 to 1.5,

R¹, which is identical or different at each occurrence, is selected from;

C₁-C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms, amino and/or carboxyl groups,

aryl and aralkyl radicals,

radicals of general formula (II);

—

C_dH_2d—

O—

(C₂H₄O)_e(C₃H₆O)_fR⁴ 

 

(II)

 

with;

R⁴ being a C₄-C₃₀ hydrocarbon radical or a radical R⁵—

(CO)—

, with R⁵ being a C₁ to C₃₀ hydrocarbon radical, and

d is an integer selected from 0 to 15, and

e and f, independently of one another, are integers selected from 0 to 50, and

combinations thereof,

R² is a radical represented by the general formula (III);

-Q-O—

X 

 

(III)

 

with;

Q being a divalent C₂-C₂₀ hydrocarbon radical which can include at least one ether bond and/or at least one ester bond, and

X being a polyhydroxylated hydrocarbon radical,

R³ is an organosiloxane of general formula (IV);

 

with;

the radicals R each representing, independently of one another, a radical selected from C₁-C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms; and

aryl and aralkyl radicals,

g is an integer selected from 1 to 5, and

h is an integer selected from 0 to 500, and at least one silicone surfactant.

22. The cosmetic composition of claim 2, wherein the silicone surfactant is selected from the group consisting of:

dimethicone copolyol,

dimethicone copolyol benzoate,

polyoxyalkylenated silicone elastomers,

a cyclomethicone/dimethicone copolyol mixture,

and mixtures thereof.

24. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C₁ to C₁₀ alkyl radical.

25. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C₁, to C₆, alkyl radical.

26. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which R¹ is a C₁ to C₄ alkyl radical.

27. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04,

R¹ is a C₁ to C₁₀ alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5, and

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

28. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04,

R¹ is a C₁ to C6 alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5, and

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

29. The cosmetic composition of claim 2, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04,

R¹ is a C₁ to C₄ alkyl radical,

R² is represented by the formula (IIIA);

—

C₃H₆O[CH₂CH(OH)CH₂O]_nH 

 

(IIIA)

in which n is selected from 1 to 5, and

R³ is represented by the formula (IVA);

—

C₂H₄(CH₃)₂SiO[(CH₃)₂SiO]_mSi(CH₃)₃ 

 

(IVA)

in which m is selected from 3 to 9.

30. The cosmetic composition according to claim 2, wherein the silicone polymer is a compound of general formula (I) in which:

a is selected from 1 to 1.4 and b and c, independently from one another, are selected from 0.02 to 0.04,

R¹ is a methyl radical,

R² is represented by the formula (IIIA) in which n is selected from 1 to 5, and

R³ is represented by the formula (IVA) in which m is selected from 3 to 9.

31. The cosmetic composition of claim 2, further comprising at least one oil selected from the group consisting of hydrogenated polyisobutene, stearyl heptanoate, isononyl isononanoate, dipentaerythritol tetrahydroxystearate, tetraisostearate, 2-octyldodecanol, isotridecyl isononanoate, diisostearyl malate, and mixtures thereof.

32. The cosmetic composition of claim 2, further comprising a silicone oil selected from the group consisting of linear silicone oils and cyclic silicone oils.

33. The cosmetic composition of claim 2, further comprising a volatile oil present at less than 15% by weight relative to a total weight of the cosmetic composition.

34. The cosmetic composition of claim 2, wherein the cosmetic composition is in cast form.

35. The cosmetic composition of claim 2, further comprising at least one colorant.

36. The cosmetic composition of claim 2, further comprising at least one compound selected from the group consisting of waxes, pasty fatty substances, and mixtures thereof.

37. The cosmetic composition of claim 2, further comprising at least one filler.

38. The cosmetic composition of claim 2, wherein the cosmetic composition is selected from the group consisting of a skin care or make-up composition and a lip care or make-up composition.

41. A method of making up and/or caring for at least one keratin material, comprising applying the cosmetic composition of claim 2 to the at least one keratin material.

42. The method of claim 41, wherein the at least one keratin material is selected from the group consisting of epidermal derivatives, mucosae, keratin fibers, skin, lips, nails, eyes, eyeslashes, and hair.

43. A method for preparing a cosmetic composition comprising combining at least one surfactant with at least one silicone polymer of general formula (I),

R¹_aR²_bR³_cSiO_(4-a-b-c)/2 

 

(I)

in which;

a is selected from 1 to 2.5, and

b and c, independently of one another, are selected from 0.001 to 1.5,

R¹, which is identical or different at each occurrence, is selected from;

C₁ to C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms, amino and/or carboxyl groups,

aryl and aralkyl radicals, and

radicals of general formula (II);

—

C_dH_2d—

O—

(C₂H₄O)_e(C₃H₆O)_fR⁴ 

 

(II)

 

with;

R⁴ being a C₁, to C₃₀ hydrocarbon radical or a radical R⁵—

(CO)—

, with R⁵ being a C₁ to C₃₀ hydrocarbon radical,

d is an integer selected from 0 to 15, and

e and f, independently of one another, are integers selected from 0 to 50,

and combinations thereof,

R² is a radical represented by the general formula (III);

-Q-O—

X 

 

(III)

 

with;

Q being a divalent C₂ to C₂₀ hydrocarbon radical which can include at least one ether bond and/or at least one ester bond, and

X being a polyhydroxylated hydrocarbon radical,

R³ is an organosiloxane group of general formula (IV);

 

with;

the radicals R each representing, independently of one another, a radical selected from C₁ to C₃₀ alkyl radicals, optionally substituted by one or more fluorine atoms; and

aryl and aralkyl radicals,

g is an integer selected from 1 to 5, and

h is an integer selected from 0 to 500, and at least one surfactant.

44. The method of claim 43, wherein the surfactant is selected from the group consisting of oxyethylenated glycerol ethers, oxypropylenated glycerol ethers, oxyethylenated fatty alcohol ethers, oxypropylenated fatty alcohol ethers, fatty acid esters of polyethylene glycol, dimethicone copolyol, dimethicone copolyol benzoate, EO/PO polycondensates, the esters and ethers of saccharides, fatty acid esters of polyol, oxyethylenated myristyl alcohol containing 15 ethylene oxide groups, oxyethylenated polyglyceryl-2 monoisostearate containing 5 ethylene oxide groups, polyglyceryl-3 diisostearate, glyceryl monoisostearate, polyglyceryl-2 monoisostearate, polyglyceryl-3 isostearate, polyglyceryl-4 isostearate, polyglyceryl-6 monoisostearate, polyglyceryl-10 monoisostearate, polyglyceryl-2 monooleate, sorbitan isostearate, sorbitan monooleate, oxyethylenated sorbitan monooleate containing 5 ethylene oxide groups, dimethicone copolyol, dimethicone copolyol benzoate, polyoxyalkylenated silicone elastomers, a cyclomethicone/dimethicone copolyol mixture, and mixtures thereof.

45. The method of claim 43, wherein the surfactant is a silicone surfactant selected from the group consisting of

dimethicone copolyol,

dimethicone copolyol benzoate,

polyoxyalkylenated silicone elastomers,

a cyclomethicone/dimethicone copolyol mixture,

and mixtures thereof.

46. The method of claim 44, wherein the cosmetic composition is anhydrous.

47. The method of claim 45, wherein the cosmetic composition is anhydrous.