Hydrophylic silicone elastomers in cosmetics

• US 20100196292A1
• Filed: 01/28/2010
• Published: 08/05/2010
• Est. Priority Date: 01/28/2009
• Status: Abandoned Application

• Current Assignee: Alzo International, Inc.
• Original Assignee: Alzo International, Inc.
• Inventors: Carson, John C., Mosquera, Michael, Awad, Nagi M., Zofchak, Albert A.
• Application Number:
  US12/657,850
• Publication Number:
  US 20100196292A1
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08G 77/22 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences

Abstract

The invention is directed to the use of a number of hydrophilic silicone elastomers in various cosmetic and personal care products where they serve various functions such as emulsifiers, film forming agents, viscosity stabilizers, conditioning agents and protective barrier forming agents. Emulsions and personal care products based upon same are also described.

Claims

1. A hydrophilic silicone elastomer comprising the reaction product of a polyorganosiloxane polymer which is reacted with an allyl alcohol ethoxylate and/or a polyurethane polymer.

2. The hydrophilic silicone elastomer according to claim 1 wherein said polyorganosiloxane is first reacted with a second polyorganosiloxane polymer before being reacted with said allyl alcohol ethoxylate and/or a polyurethane polymer.

3. The hydrophilic silicone elastomer according to claim 1 wherein said allyl alcohol ethoxylate is according to the chemical structure:

Where f is a positive integer from 1 to 20.

4. The hydrophilic silicone elastomer according to claim 1 wherein said polyorganosiloxane polymer is a polymeric composition comprised of

units, where R² and R³ are independently H, OH, C₁-C₁₀ alkyl, C₂-C₁₀ alkene or aryl groups and varies in average molecular weight M_n from about 1,000 to about 1,500,000 or more, preferably about 1,000 to about 100,000.

5. The hydrophilic silicone elastomer according to claim 4 wherein said polyorganosiloxane polymer contains a number of groups which are capable of crosslinking with an allyl alcohol ethoxylate according to the chemical structure:

Where f is a positive integer from 1 to 20; and

/or

with a reactive polyurethane polymer containing a crosslinkable functional group.

6. The hydrophilic silicone elastomer according to claim 5 wherein said reactive polyurethane polymer contains a hydrogen, OH, NH₂ or olefinic functional group.

7. The hydrophilic silicone elastomer according to claim 5 wherein said polyorganosilixane polymer contains a number of groups which are capable of crosslinking with said alkyl alcohol ethoxylate and said polyurethane polymer.

8. The hydrophilic silicone elastomer according to claim 4 wherein said polyorganosiloxane polymer is a compound according to the chemical structure:

Where R¹ and R^a are independently H, a C₁-C₆ alkyl group which is optionally substituted with OH or a C₁-C₃ alkyl group which itself is optionally substituted with a hydroxyl group or an optionally substituted C₂-C₆ alkenyl group;

Each R² and R³ is independently H, OH, or a C₁-C₃ alkyl group; and

n is from 5 to 50,000.

9. The hydrophilic silicone elastomer according to claim 8 wherein said alkenyl group is an acrylate or (meth)acrylate group.

10. The hydrophilic silicone elastomer according to claim 1 wherein said polyorganosiloxane polymer is a compound according to the chemical structure:

Where R¹ and R^a are each independently H, a C₁-C₆ alkyl group optionally substituted with OH or a C₁-C₃ alkyl group which itself is optionally substituted with a hydroxyl group, or an optionally substituted C₂-C₆ alkenyl group;

Each R² and R³ is independently H, OH, or a C₁-C₃ alkyl group;

Each R^2a and R^3a is independently H, OH, or a C₁-C₃ alkyl group;

n is from 5 to 50,000; and

j is from 0 to 50.

11. The hydrophilic silicone elastomer according to claim 1 wherein said polyorganosiloxane polymer is crosslinked with a polysiloxane crosslinking agent before reaction with said allyl alcohol ethoxylate and/or polyurethane.

12. The hydrophilic silicone elastomer according to claim 1 wherein said polyurethane has the general structure:

Where R⁵ is a C₁-C₅₀ hydrocarbon or a siloxane group each of which groups may be optionally substituted with at least one hydroxyl and/or polyethylene glycol group and wherein each of said hydrocarbon or siloxane groups optionally contains at least one polymerizable olefinic group;

R^5a is a C₁-C₅₀ hydrocarbon or a siloxane group each of which groups may be optionally substituted with hydroxyl and/or polyethylene glycol groups and wherein each of said hydrocarbon or siloxane groups optionally contains at least one polymerizable olefinic group;

R′

is an optionally substituted C₂ through C₃₆ linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; and

m is from 1 to about 250.

13. The hydrophilic silicone elastomer according to claim 12 wherein R⁵ is a C₂-C₅₀ hydrocarbon group containing at least one olefinic group which is optionally substituted with at least one hydroxyl group and/or a polyethylene glycol group wherein said polyethylene glycol group ranges in size from 1 to about 100 polyethylene oxide groups, or a polyethylene oxide group comprising between 1 and 500 ethylene oxide groups which is endcapped with a polymerizable alkenyl, acrylate or (meth)acrylate group and R^5a is a C₂-C₅₀ hydrocarbon group containing at least one olefinic group which is optionally substituted with hydroxyl groups and/or polyethylene glycol groups, or a polyethylene oxide group comprising between 1 and 500 ethylene oxide groups which is endcapped with a polymerizable alkenyl, acrylate or (meth)acrylate group and R′

is an isophorone group.

14. The hydrophilic silicone elastomer according to claim 12 wherein at least one of R⁵ and R^5a is a siloxane group and wherein said R⁵ siloxane group has the structure:

and

said R^5a siloxane group has the structure;

Wherein Y is absent, O or a —

W—

(O—

Z)_r-Q-(CH₂)_q-T-group;

X is absent or a -T

CH₂)_q-Q-(Z—

O)_r—

W′

-group;

X′

is absent or a —

W′

—

(O—

Z)_r-Q-(CH₂)_q-T-group;

Y′

is absent or a -T

CH₂)_q-Q-(Z—

O)_r—

W² group;

Y′

is absent or a group;

W is absent when r is an integer of 1 or more and W is absent or O when r is 0;

Q is absent or O;

q is an integer from 0 to 10;

r is an integer from 0 to 100, with the proviso that q or r is at least 1;

T is absent or O;

W′

is absent when r is 0 and is a Z group when r is 1 or more;

W² is H;

Z is independently an ethylene group, a propylene group or a mixture of ethylene and propylene groups;

R^2b and R^3b are each independently H or a C₁-C₃ alkyl group;

R^2c and R^3c are independently selected from H, an optionally substituted C₁-C₆ alkyl group or an optionally substituted C₂-C₆ alkenyl group;

i is an integer from 0 to 50; and

k is an integer from 0 to 100.

15. The hydrophilic silicone elastomer according to claim 14 wherein R⁵ is a O—

R⁶ group and R^5a is a R⁶—

OH group wherein R⁶ is a C₁-C₅₀ hydrocarbon which is optionally substituted with at least one hydroxyl group and/or polyethylene glycol groups ranging in size from about 2 to about 100 polyethylene oxide units,

16. The hydrophilic silicone elastomer according to claim 1 in the form of a gel.

17. The hydrophilic silicone elastomer according to claim 1 wherein hydrophilic character is instilled in said elastomer by incorporation of effective amounts of allyl alcohol ethoxylate residues.

18. The hydrophilic silicone elastomer according to claim 1 wherein hydrophilic character is instilled in said elastomer by incorporation of effective amounts of allyl alcohol ethoxylate residues and/or a polyurethane residue.

19. The hydrophilic silicone elastomer according to claim 1 in combination with an oil.

20. The hydrophilic silicone elastomer according to claim 1 in combination with a preservative, an antioxidant or mixtures thereof.

21. An emulsion comprising an effective amount of a hydrophilic silicone elastomer according to claim 1 in combination with an oil, water and optionally, a secondary emulsifier (a traditional emulsifier).

22. The emulsion according to claim 21 further comprising at least one additional component selected from the group consisting of an aqueous solvent, a non-aqueous solvent, emollients, humectants, oils, conditioning agents, emulsifiers, surfactants, thickeners, stiffening agents, medicaments, fragrances, preservatives, deodorant components, anti-perspirant compounds, skin protecting agents, pigments, vitamins, nutraceuticals, sunscreens and mixtures thereof.

23. A personal care composition comprising a hydrophilic silicone elastomer or emulsion composition according to claim 1.

24. The personal care composition according to claim 23 wherein said additional component selected from the group consisting of an aqueous solvent, a non-aqueous solvent, emollients, humectants, oils, conditioning agents, emulsifiers, surfactants, thickeners, stiffening agents, medicaments, fragrances, preservatives, deodorant components, anti-perspirant compounds, skin protecting agents, pigments, vitamins, antioxidants, sunscreens and mixtures thereof.

25. A method of preparing a hydrophilic silicone elastomer according to claim 1 by reacting a polyorganosiloxane with about 0.5% to about 25% by weight of the reaction mixture of an allyl alcohol ethoxylate monomer and/or a polyurethane in a single step reaction.

26. The method according to claim 25 wherein said allyl alcohol ethoxylatre and/or said polyurethane comprises about 1% to about 15% by weight of the reaction mixture which includes silicone elastomer, allyl alcohol ethoxylate and/or polyurethane and any additional reactants included.

27. The method according to claim 25 wherein said allyl alcohol ethoxylatre and/or said polyurethane comprises about 1% to about 10% by weight of the reaction mixture which includes silicone elastomer, allyl alcohol ethoxylate and/or polyurethane and any additional reactants included.

28. A method of preparing an emulsion comprising mixing a hydrophilic silicone elastomer according to claim 1 with an oil, water and optionally, a secondary emulsifier and optionally, at least one additional component selected from the group consisting of aqueous solvent (e.g. alcohol or other water compatible solvent), a non-aqueous solvent, emollients, humectants, oils (polar and non-polar), conditioning agents, emulsifiers, including secondary emulsifiers, surfactants, thickeners, stiffening agents, medicaments, fragrances, preservatives, deodorant components, anti-perspirant compounds, skin protecting agents, pigments, sunscreens and mixtures thereof.

29. A method of instilling hydrophilic character to a silicone elastomer comprising reacting a polyorganosiloxane compound with a polyurethane and/or allyl alcohol ethoxylate to produce a hydrophilic silicone elastomer.