IP Library Granted Patent US 8,580,285
Granted Patent B2
US 8,580,285 · App. 13/156,499 · Granted Nov 12, 2013

Clarifying agents for organomodified silicones

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Quick Facts
Patent No.
US 8,580,285
App. No.
13/156,499
Granted
Nov 12, 2013
Kind
B2
Abstract

There is provided herein a composition comprising a silicone copolymer of the general formula (I) M a M E c D d D E e T f T E g Q h where M=R 1 R 2 R 3 SiO 1/2 ; M E =R 4 R 5 R E SiO 1/2 ; D=R 6 R 7 SiO 2/2 ; D E =R 8 R E SiO 2/2 ; T=R 9 R E SiO 2/2 ; T=R 9 SiO 3/2 ; T E =R E SiO 2/2 ; and Q=SiO 4/2 ; where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group of monovalent hydrocarbon radicals R E is a monovalent radical defined as: —R 10 O—(C 2 H 4 O) h (C 3 H 6 O) i (C 4 H 8 O) i —R 11 or —R 12 with the provision that the copolymer must contain at least one R E group; R 10 is a linear or branched divalent hydrocarbon radical containing from 3 to about 10 carbon atoms; R 11 is H or —C(═O)CH 3 or a monovalent saturated or unsaturated hydrocarbon radical, optionally containing heteroatoms and hydroxyl groups, containing from 1 to about 30 carbon atoms; R 12 is a hydrocarbon radical, containing from 2 to about 30 carbon atoms and at least 1 hydroxyl group, optionally containing heteroatoms; subscripts a, b, c, d, e, f, and g are 0 or positive subject to the limitation a+b+c+d+e+f+g<1000; subscripts h, i, and j are 0 or positive subject to the limitation h+i+j is less than 100; and, b) an organic oil.

Claims (68)

1. A composition comprising

a) a silicone copolymer of the general formula (I)

M a M E b D c D E d T e T E f Q g   (I)

where

M=R 1 R 2 R 3 SiO 1/2 ;

M E =R 4 R 5 R E SiO 1/2 ;

D=R 6 R 7 SiO 2/2 ;

D E =R 8 R E SiO 2/2 ;

T=R 9 SiO 3/2 ;

T E =R E SiO 2/2 ; and

Q=SiO 4/2 ;

where

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group of monovalent hydrocarbon radicals optionally containing heteroatoms, carbonyl groups, and hydroxyl groups, each independently containing from about 1 to about 20 carbon atoms;

R E is a monovalent radical defined as: —R 10 O—(C 2 H 4 O) h (C 3 H 6 O) i (C 4 H 8 O) j —R 11 or —R 12 with the provision that the copolymer must contain at least one R E group;

R 10 is a linear or branched divalent hydrocarbon radical containing from 3 to about 10 carbon atoms;

R 11 is H, —C(═O)CH 3 , or a monovalent saturated or unsaturated hydrocarbon radical, optionally containing heteroatoms and hydroxyl groups, containing from 1 to about 30 carbon atoms;

R 12 is a hydrocarbon radical, containing from 2 to about 30 carbon atoms and at least 1 hydroxyl group, optionally containing heteroatoms;

subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitation a+b+c+d+e+f+g<1000;

subscripts h, i, and j are zero or positive and are subject to the limitation h+i+j is less than 100; and,

b) an organic ester selected from the group consisting of myristal proprionate, neopentylglycol dioctanoate, diethylhexyl maleate, diisopropyl adipate, diacetyl maleate, dicaprylyl maleate, diisopropryl sebacate, diethyl malonate, diethyl oxalate, dimethyl adipate, dimethyl maleate, dibutyl sebacate, dibutyl fumarate, dipropyl oxalate, decanedioic acid diethyl ester, dibenzyl malonate, dipropyl glutarate, diethyl succinate and combinations thereof, and which exhibits Hansen solubility parameters of 14<δ D <18, 4<δ H <10 and 3<δ P <15, and wherein the composition has a viscosity of less than 20,000 cps at room temperature,

wherein the amount of silicone copolymer (a) is at least about 40 weight percent based on the total weight of the composition.

2. The composition of claim 1 wherein the composition has a viscosity of less than 15,000 cps.

3. The composition of claim 1 wherein the composition has a viscosity of less than 10,000 cps.

4. The composition of claim 1 wherein the composition has a viscosity of from about 1,000 to about 5,000 cps.

5. The composition of claim 1 wherein the composition is translucent.

6. The composition of claim 1 wherein the composition is clear.

7. The composition of claim 1 wherein the composition has a shelf stability of at least one month.

8. The composition of claim 1 wherein the composition is in the absence of water.

9. The composition of claim 1 wherein the composition is translucent, has a shelf stability of at least one month, and is in the absence of water.

10. The composition of claim 1 wherein the silicone copolymer (a) has a viscosity of greater than 20,000 cps at room temperature.

11. A non-aqueous silicone emulsion comprising the composition of claim 1 .

12. A personal care composition comprising the non-aqueous silicone emulsion of claim 11 .

13. The personal care composition of claim 12 selected from the group consisting of deodorant, antiperspirant, antiperspirant/deodorant, shaving product, skin lotion, moisturizer, toner, bath product, cleansing product, hair product, shampoo, conditioner, mousse, styling gel, hair spray, hair dye, hair color product, hair bleach, waving product, hair straightener, hair frizz control product; hair volumizing product; manicure product, nail polish, nail polish remover, nail cream and lotion, cuticle softener, sunscreen, insect repellent and anti-aging product, color cosmetic, lipstick, foundation, face powder, eye liner, eye shadow, blush, makeup, mascara, and other personal care formulations where silicone components have been conventionally added, and drug delivery system for topical application of medicinal composition that is to be applied to the skin.

14. A process of treating a silicone surfactant comprising mixing the contents of a composition, wherein the composition comprises

(a) a silicone copolymer of the general formula (I):

M a M E b D c D E d T e T E f Q g   (I)

where

M=R 1 R 2 R 3 SiO 1/2 ;

M E =R 4 R 5 R E SiO 1/2 ;

D=R 6 R 7 SiO 2/2 ;

D E =R 6 R E SiO 2/2 ;

T=R 9 SiO 3/2 ;

T E =R E SiO 2/2 ; and

Q=SiO 4/2 ;

where

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group of monovalent hydrocarbon radicals optionally containing heteroatoms, carbonyl groups, and hydroxyl groups, each independently having from about 1 to about 20 carbon atoms, preferably from about 1 to about 15 carbon atoms and more preferably from about 1 to about 10 carbon atoms;

R E is a monovalent radical defined as: —R 10 O—(C 2 H 4 O) h (C 3 H 6 O) i (C 4 H 8 O) j —R 11 or —R 12 with the provision that the copolymer must contain at least one R E group;

R 10 is a linear or branched divalent hydrocarbon radical containing from 3 to about 10 carbon atoms;

R 11 is H, —C(═O)CH 3 , or a monovalent saturated or unsaturated hydrocarbon radical, optionally containing heteroatoms and hydroxyl groups, having from 1 to about 30 carbon atoms;

R 12 is a hydrocarbon radical, containing from 2 to about 30 carbon atoms and at least 1 hydroxyl group, optionally containing heteroatoms;

subscripts a, b, c, d, e, f, and g are zero or positive subject to the limitation a+b+c+d+e+f+g<1000;

subscripts h, i, and j are zero or positive and are subject to the limitation h+i+j is less than 100; and,

b) an organic ester selected from the group consisting of myristal proprionate, neopentylglycol dioctanoate, diethythexyl maleate, diisopropyl adipate, diacetyl maleate, dicaprylyl maleate, diisopropryl sebacate, diethyl malonate, diethyl oxalate, dimethyl adipate, dimethyl maleate, dibutyl sebacate, dibutyl fumarate, dipropyl oxalate, decanedioic acid diethyl ester, dibenzyl malonate, dipropyl glutarate, diethyl succinate and combinations thereof, and which exhibits Hansen solubility parameters of 14<δ D <18, 4<δ H <10 and 3<δ P <15,

wherein the mixing results in the composition having a viscosity of less than 20,000 cps at room temperature and, wherein the amount of silicone copolymer (a) is at least about 40 weight percent based on the total weight of the composition.

15. The process of claim 14 wherein the composition is translucent following mixing.

16. The process of claim 14 wherein the composition has a shelf stability of at least one month following mixing.

17. The process of claim 14 wherein the composition is in the absence of water.

18. The process of claim 14 wherein the composition is translucent and has a shelf stability of at least one month following mixing.

19. The composition comprising a silicone copolymer (a) having the formula:

wherein R E may be of the formula:

—CH—CH—CH 2 —O—(CH 2 CH 2 O) 20 —(CH(CH 3 )CH 2 O) 15 H

and,

b) an organic ester which exhibits Hansen solubility parameters of 14<δ D <18, 4<δ H <10 and 3<δ P <15 and wherein the composition has a viscosity of less than 20,000 cps at room temperature.

20. A composition comprising a silicone copolymer (a) having the formula:

wherein R* is of the formula:

and R 12 is of the formula:

and,

b) an organic ester which exhibits Hansen solubility parameters of 14<δ D <18, 4<δ H <10 and 3<δ P <15, and wherein the composition has a viscosity of less than 20,000 cps at room temperature.

Assignments (22)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
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