Core/shell particles based on silicone compounds

• US 20080254077A1
• Filed: 12/19/2007
• Published: 10/16/2008
• Est. Priority Date: 12/20/2006
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Prigent, Fanny
• Application Number:
  US12/003,025
• Publication Number:
  US 20080254077A1
• Time in Patent Office: Days
• US Class Current: 424/401
• CPC Class Codes: A61K 2800/412 Microsized, i.e. having sizes between 0.1 and 100 microns
• CPC Class Codes: A61K 8/11 Encapsulated compositions
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: B01J 13/14 Polymerisation; cross-linking

Abstract

The present invention relates to particles of core/shell type suitable for the encapsulation of cosmetic and/or therapeutic lipophilic active agents. It also relates to a process for preparing said particles as well as cosmetic or therapeutic compositions comprising them.

Claims

1. Particle of core/shell type having a lipophilic core, wherein its shell is formed at least partly by a silicone polymer film which is the product of in situ reaction between at least one compound X and at least one compound Y, at least one of compounds X and Y being a polyorganosiloxane and said reaction being of hydrosilylation type carried out in the presence of a catalyst, condensation type carried out, if applicable, in the presence of a catalyst, or crosslinking type carried out in the presence of a peroxide.

2. Particle according to claim 1, wherein the core comprises at least one oil and/or a lipophilic cosmetic or therapeutic active agent.

3. Particle according to claim 1, wherein the average particle diameter ranges from 50 nm to 1 μ

m.

4. Particle according to claim 1, wherein the shell is also coated at least partly by a lamellar phase.

5. Particle according to claim 1, wherein compounds X and Y are capable of reacting by hydrosilylation in the presence of a catalyst.

6. Particle according to claim 5, wherein compound X is selected from silicone compounds comprising at least two unsaturated aliphatic groups.

7. Particle according to claim 5, wherein compound X is a polyorganosiloxane comprising a silicone main chain whose unsaturated aliphatic groups are pendent from the main chain (side group) or located at the ends of the main chain of the compound (end group).

8. Particle according to claim 7, wherein compound X bears at least one polar group.

9. Particle according to claim 5, wherein compound X is selected from the polyorganosiloxanes comprising at least two unsaturated aliphatic groups each attached to a silicon atom.

10. Particle according to claim 5, wherein compound X is selected from the polyorganosiloxanes containing siloxane units of formula:

in which;

11. Particle according to claim 10, wherein the polyorganosiloxane of formula (I) is such that R′

represents a vinyl group or a group —

R″

—

CH═

CHR′

″

in which R″

is a divalent aliphatic hydrocarbon chain, having from 1 to 8 carbon atoms, bound to the silicon atom and R′

″

is a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms.

12. Particle according to claim 10, wherein R represents an alkyl radical having from 1 to 10 carbon atoms or alternatively a phenyl group and R′

is a vinyl group.

13. Particle according to claim 7, wherein the polyorganosiloxanes additionally comprise units of formula:

14. Particle according to claim 5, wherein compound X is selected from organic oligomers or polymers, hybrid organic/silicone oligomers or polymers, said oligomers or polymers bearing at least 2 unsaturated reactive aliphatic groups.

15. Particle according to claim 5, wherein compound Y comprises at least two free Si—

H groups.

16. Particle according to claim 5, wherein compound Y is selected from the polyorganosiloxanes comprising at least one alkylhydrogenosiloxane unit with the following formula:

17. Particle according to claim 16, wherein compound Y is such that the radicals R represent a C₁-C₁₀ alkyl group.

18. Particle according to claim 15, wherein Y is a polyorganosiloxane comprising at least two alkylhydrogenosiloxane units of formula —

(H₃C)(H)Si—

O—

.

19. Particle according to claim 5, wherein the hydrosilylation is carried out in the presence of a catalyst based on platinum or tin.

20. Particle according to claim 19, wherein the catalyst represents from 0.0001% to 20% by weight relative to its total weight.

21. Particle according to claim 5, wherein compound X is a polydimethylsiloxane with vinylic end groups and compound Y is a polymethylhydrogenosiloxane.

22. Particle according to claim 1, wherein compound X bears at least one polar group that is able to form a hydrogen bond with keratin materials.

23. Particle according to claim 1, wherein compound X has a weight-average molecular weight (Mw) in the range from 150 to 1 000 000.

24. Particle according to claim 1, wherein compound Y has a weight-average molecular weight (Mw) in the range from 200 to 1 000 000.

25. Particle according to claim 1, wherein compounds X and Y are present in the particles in a molar ratio X/Y in the range from 0.05 to 20.

26. Particle according to claim 1, wherein the core comprises at least one oil.

27. Particle according to claim 1, wherein the core contains at least one lipophilic active agent other than an oil.

28. Particle according to claim 27, wherein said active agent is chosen from D-α

-tocopherol, DL-α

-tocopherol, D-α

-tocopheryl acetate, DL-α

-tocopheryl acetate, ascorbyl palmitate, vitamin F glycerides, D vitamins, vitamin D₂, vitamin D₃, retinol, retinyl esters, retinyl palmitate, retinyl propionate, carotenes, including β

-carotene, D-panthenol, farnesol, farnesyl acetate, salicylic acid and derivatives thereof, for instance 5-n-octanoylsalicylic acid, alkyl esters of α

-hydroxy acids such as citric acid, lactic acid, glycolic acid, asiatic acid or madecassic acid, asiaticoside, the total extract of Centella asiatica, β

-glycyrrhetinic acid;

α

-bisabolol, ceramides, for instance 2-oleoylamino-1,3-octadecane, phytanetriol, phospholipids of marine origin rich in polyunsaturated essential fatty acids, ethoxyquine, extract of rosemary, extract of lemon balm, quercetin, extract of dried microalgae, essential oil of bergamot, octyl methoxycinnamate, butylmethoxydibenzoylmethane, octyl triazone, 3,5-di-tert-butyl-4-hydroxy-3-benzylidene-camphor, antibiotics, antifungal agents, anaesthetics, analgesics, antiseptics, antiviral agents, pesticides, herbicides, anti-inflammatory agents, antibacterial agents and antimitotic agents, and mixtures thereof.

29. Aqueous dispersion of particles according to claim 1.

37. Cosmetic and/or therapeutic composition containing, in a physiologically acceptable medium, at least one particle according to claim 1.

38. Composition according to claim 37, wherein said particle contains at least one lipophilic agent chosen from D-α

-tocopherol, DL-α

-tocopherol, D-α

-tocopheryl acetate, DL-α

-tocopheryl acetate, ascorbyl palmitate, vitamin F glycerides, D vitamins, vitamin D₂, vitamin D₃, retinol, retinyl esters, retinyl palmitate, retinyl propionate, carotenes, including β

-carotene, D-panthenol, framesol, farnesyl acetate, salicylic acid and derivatives thereof, for instance 5-n-octanoylsalicylic acid, alkyl esters of α

-hydroxy acids such as citric acid, lactic acid, glycolic acid, asiatic acid or madecassic acid, asiaticoside, the total extract of Centella asiatica, β

-glycyrrhetinic acid, α

-bisabolol, ceramides, for instance 2-oleoylamino-1,3-octadecane, phytanetriol, phospholipids of marine origin rich in polyunsaturated essential fatty acids, ethoxyquine, extract of rosemary, extract of lemon balm, quercetin, extract of dried microalgae, essential oil of bergamot, octyl methoxycinnamate, butylmethoxydibenzoylmethane, octyl triazone and 3,5-di-tert-butyl-4-hydroxy-3-benzylidenecamphor.

39. Composition according to claim 37, wherein it is in the form of a composition for caring for and/or making up keratin material(s).

40. Cosmetic method for treating keratin material(s), comprising at least the application to a keratin material of particles according to claim 1.

41. Cosmetic method for treating keratin material(s), comprising at least the application to a keratin material of a composition according to claim 37.

30. Process for preparing particles of core/shell type, the core of which is lipophilic and the shell of which is formed at least partly from a silicone polymer film, comprising at least steps of:

i. dissolving, in at least one volatile organic solvent, at least one lipophilic compound, a compound X and a compound Y, with at least one of the compounds X and Y being an organopolysiloxane and compounds X and Y being under conditions not suitable for their interaction, and

ii. placing the organic phase from step 1 in contact with an aqueous phase containing, where appropriate, at least one surfactant, under conditions suitable for the formation of lipophilic droplets and for the reaction of compounds X and Y according to a reaction of hydrosilylation type in the presence of a catalyst, or of condensation or crosslinking type in the presence of a peroxide, to form a silicone polymer film at the surface of said droplets.

31. Process according to claim 30, wherein said particles formed are isolated via evaporation of the organic solvent(s).

32. Process according to claim 30, wherein the organic solvent is sparingly water-miscible and step 2 corresponds to an emulsification of the organic phase from step 1 in the aqueous phase in the form of droplets, at the surface of which compounds X and Y interact to form the polymer film constituting the shell of said particles.

33. Process according to claim 30, wherein the organic solvent is water-miscible and step 2 corresponds to solvent tipping, during which the diffusion of the aqueous phase into the organic phase causes the formation of droplets, at the surface of which compounds X and Y interact to produce the polymer film forming the shell of said particles.

34. Process according to claim 30, at least one of compounds X and Y being a polyorganosiloxane.

35. Process according to claim 30, wherein the organic phase of step 1 also comprises a catalyst.

36. Process according to claim 30, wherein the organic phase of step 1 also comprises a compound capable of forming a lamellar phase at the surface of said particles.