SILICONE POLYETHER ELASTOMER GELS

• US 20100158824A1
• Filed: 03/20/2007
• Published: 06/24/2010
• Est. Priority Date: 03/21/2006
• Status: Active Grant

• Current Assignee: Dow Silicones Corporation (Dow, Inc.)
• Original Assignee: Dow, Inc.
• Inventors: Lin, Shaow
• Granted Patent: US 8,273,840 B2
• Time in Patent Office: Days
• US Class Current: 514/1.100
• CPC Class Codes: A61K 8/042 Gels
• CPC Class Codes: A61K 8/31 Hydrocarbons
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/585 Organosilicon compounds
• CPC Class Codes: A61K 8/671 Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08G 77/045 containing less than 25 silicon atoms
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence
• CPC Class Codes: C08L 83/12 containing polyether sequences

Abstract

Gel compositions are disclosed containing a silicone polyether elastomer from the reaction of an organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule, a compound or mixture of compounds having at least two aliphatic unsaturated groups in its molecule, and a hydrosilylation catalyst. The silicone polyether elastomer reaction product may itself be a gelled composition, or optionally may be contained in a carrier fluid to form a gel. The gel compositions may further contain a personal or healthcare active.

Claims

1. A gel composition comprising a silicone polyether elastomer from the reaction of;

A) an organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule

B) a compound or mixture of compounds having at least two aliphatic unsaturated hydrocarbon groups in its molecule,

C) a hydrosilylation catalyst, and

D) an optional carrier fluid,

with the proviso that at least 10 weight % of B) is a polyether compound.

2. The composition of claim 1 further comprising

E) a personal care or healthcare active.

3. The composition of claim 1 wherein the organohydrogensiloxane has the formula G-[Y-G]_a where G is a cyclosiloxane containing at least one SiH unit and Y is a divalent organic group, a divalent siloxane group, a divalent polyoxyalkylene group, or combination thereof, and a is greater than zero.

4. The composition of claim 1 wherein the organohydrogensiloxane is prepared by a hydrosilylation reaction of

a) an organohydrogencyclosiloxane having at least two SiH units on the siloxane ring and,

B) a compound or mixture of compounds having at least two aliphatic unsaturated hydrocarbon groups in its molecule,

wherein the molar ratio of SiH units to unsaturated group ranges from 2/1 to 8/1.

5. The composition of claim 4 wherein the organohydrogencyclosiloxane has the formula [(CH₃)HSiO]_g where g is 3-8.

6. The composition of claim 1 wherein B) the compound containing at least two aliphatic unsaturated hydrocarbon groups in its molecule is selected from a compound having the formula R²—

Y—

R² where R² is a monovalent unsaturated aliphatic group and Y is a divalent hydrocarbon, a siloxane, a polyoxyalkylene or mixtures thereof.

7. The composition of claim 6 wherein Y is a polyoxyalkylene group having the formula —

[(C₂H₄O)_c (C₃H₆O)_d (C₄H₈O)_e]—

where c, d, and e may each independently range from 0 to 200, providing the sum of c+d+e is greater than 2.

8. The composition of claim 1 wherein B) the compound containing at least two aliphatic unsaturated groups in its molecule is selected from the group

H₂C═

CHCH₂[C₃H₆O]_dCH₂CH═

CH₂

H₂C═

CH[C₃H₆O]_dCH═

CH₂

H₂C═

C(CH₃)CH₂[C₃H₆O]_dCH₂C(CH₃)═

CH₂

HC≡

CCH₂[C₃H₆O]_dCH₂C≡

CH, and

HC≡

CC(CH₃)₂[C₃H₆O]_dC(CH₃)₂C≡

CH

where d is greater than 2.

9. The composition of claim 1 wherein B) the compound containing at least two aliphatic unsaturated groups has the formula H₂C═

CHCH₂[C₃H₆O]_dCH₂CH═

CH₂, where d is greater than 2.

10. The composition of claim 9 where d ranges from 5 to 50.

11. The composition of claim 1 wherein the compound containing at least two aliphatic unsaturated groups is selected from an organopolysiloxane comprising at least two siloxane units having a formula R²R_mSiO₄₋

m/2 wherein

R is an organic group,

R² is a monovalent unsaturated aliphatic group, and

m is zero to 3.

12. The composition of claim 11 wherein the organopolysiloxane has the formula

(R₂R²SiO_0.5)(SiO₂)_w(R₂R²SiO_0.5)

(R₂R²SiO_0.5) (SiO₂)_w(R₂SiO)_x(R₂R²SiO_0.5)

(R₂R²SiO_0.5)(R₂SiO)_x(R₂R²SiO_0.5)

(R₃SiO_0.5)(R₂SiO)_x(R²RSiO)_y(R₃SiO_0.5)

(R₃SiO_0.5)(R₂SiO)_x(R²RSiO)_y(RSiO_1.5)_x(R₃SiO_0.5)

(R₃SiO_0.5)(R₂SiO)_x(R²RSiO)_y(SiO₂)_w(R₃SiO_0.5)

where w≧

0, x≧

0, y≧

2, and z is 0,

and R is an organic group, and R² is a monovalent unsaturated aliphatic hydrocarbon group.

13. The composition of claim 12 wherein R is methyl and R³ is CH₂═

CH—

or CH₂═

CH—

(CH₂)₄—

.

14. The composition of claim 11 wherein the organopolysiloxane is a vinyl functional or hexenyl functional polydimethylsiloxane having the average formula;

CH₂═

CH(Me)₂SiO[Me₂SiO]_xSi(Me)₂CH═

CH₂

CH₂═

CH—

(CH₂)₄(Me)₂SiO[Me₂SiO]_xSi(Me)₂—

(CH₂)₄—

CH═

CH₂, or

Me₃SiO[(Me)₂SiO]_x[CH₂═

CH(Me)SiO]_ySiMe₃

wherein Me is methyl, x≧

0, and y≧

2.

15. The composition of claim 1 wherein C) the hydrosilylation catalyst is a platinum group containing catalyst.

16. The composition of claim 1 wherein the molar ratio of A)/B) is from 10/1 to 1/10.

17. The composition of claim 1 wherein the carrier fluid is a silicone or organic fluid having a viscosity at 25°

C. in the range of 1 to 1,000 mm²/sec.

18. The composition of claim 1 wherein the carrier fluid is decamethylcyclopentasiloxane, isododecane, or isodecyl neopentanoate.

19. The composition of claim 2 wherein E) is a personal care active selected from a vitamin, sunscreen, plant extract, or fragrance.

20. The composition of claim 2 wherein E) is a health care active selected from a topical drug active, protein, enzyme, antifungal, or antimicrobial agent.

21. The composition of claim 2 wherein component E) is vitamin A palmitate.

22. The composition of claim 2 wherein component E) is octyl methoxycinnamate.

27. A process for preparing a gel paste composition comprising;

I) shearing the silicone elastomer gel of claims 1,

II) combining the sheared silicone elastomer gel with additional quantities of D) the carrier fluid to form a gel paste composition.

28. The process of claim 27 further comprising the addition of

E) a personal care or healthcare active in step II).

29. The gel paste composition prepared according to the process of claim 27.

23. A process for preparing a silicone polyether elastomer gel comprising:

I) reacting;

a) an organohydrogencyclosiloxane having at least two SiH units on a siloxane ring,

B) a compound or mixture of compounds containing at least two aliphatic unsaturated hydrocarbon groups in its molecules.

C) a hydrosilylation catalyst to form

A) an organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule,

wherein the molar ratio of the SiH units of component a) to the aliphatic unsaturated groups of component B) ranges from 2/1 to 8/1,

II) further reacting;

A) the organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule, with additional quantities of

B) the compound containing at least two aliphatic unsaturated groups in its molecules,

C) the hydrosilylation catalyst, in the presence of

D) an optional carrier fluid,

with the proviso that at least 10 weight % of B) is an polyether compound, to form the silicone elastomer gel.

24. A process for preparing a silicone polyether elastomer gel containing an active comprising:

I) reacting;

a) an organohydrogencyclosiloxane having at least two SiH units on a siloxane ring,

B) a compound or mixture of compounds containing at least two aliphatic unsaturated hydrocarbon groups in its molecules,

C) a hydrosilylation catalyst. to form

A) an organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule,

wherein the molar ratio of the SiH units of component a) to the aliphatic unsaturated hydrocarbon groups of component B) ranges from 2/1 to 8/1,

II) reacting;

A) the organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule, with additional quantities of

B) the compound containing at least two aliphatic unsaturated hydrocarbon groups in its molecules,

C) the hydrosilylation catalyst, in the presence of

D) an optional carrier fluid, and

E) a personal care or healthcare active,

with the proviso that at least 10 weight % of B) is an polyether compound, to form the silicone polyether elastomer gel.

25. A process for preparing a silicone polyether elastomer gel containing an active comprising:

I) reacting;

a) an organohydrogencyclosiloxane having at least two SiH units on a siloxane ring,

B) a compound or mixture of compounds containing at least two aliphatic unsaturated groups in its molecules,

C) a hydrosilylation catalyst to form

A) an organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule,

wherein the molar ratio of the SiH units of component a) to the aliphatic unsaturated groups of component B) ranges from 2/1 to 8/1,

II) further reacting;

A) the organohydrogensiloxane having at least two SiH containing cyclosiloxane rings in its molecule, with additional quantities of

B) the compound containing at least two aliphatic unsaturated groups in its molecules,

C) the hydrosilylation catalyst, in the presence of

D) an optional carrier fluid,

with the proviso that at least 10 weight % of B) is an polyether compound, to form a silicone elastomer gel,

III) admixing

E) a personal care or healthcare active with the silicone elastomer gel to form the silicone polyether elastomer gel containing active.

26. The silicone polyether elastomer gel prepared according to claim.