IP Library Granted Patent US 7,790,801
Granted Patent B2
US 7,790,801 · App. 11/880,831 · Granted Sep 7, 2010

Organo-functional silicone in emulsion systems and process for preparing same

Assignee: Momentive Performance Materials Inc.
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Quick Facts
Patent No.
US 7,790,801
App. No.
11/880,831
Granted
Sep 7, 2010
Kind
B2
Abstract

The present invention provides a process for preparing substantially two-dimensional partially crosslinked organo-functional silicone in an aqueous emulsion system. The novel composition provides enhanced surface softness and smoothness to various materials.

Claims (77)

1. An aqueous silicone-containing emulsion comprising:

a) an emulsion-forming amount of water;

b) at least one silicone possessing a substantially planar crosslinked structure;

c) an emulsion-forming amount of a surfactant mixture of at least one cationic surfactant and at least one nonionic surfactant; and,

d) at least one additional component selected from the group consisting of pH buffering agents, rewetting agents, viscosity modifiers, antigelling agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, anti-redeposition agents, enzymes, optical brightening agents, opacifiers, stabilizers, emulsifiers, anti-shrinking agents, anti-wrinkle agents, fabric crisping agents, anti-spotting agents, soil-release agents, germicides, fungicides, biocides, anti-oxidants, anti-corrosion agents; preservatives, pigments, dyes, bleaches, drape imparting agents, antistatic agents fillers, thickeners, and ironing aids.

2. The aqueous silicone-containing emulsion of claim 1 wherein silicone (b) is obtained from the copolymerization of (i) at least one cyclic and/or linear siloxane and (ii) at least one tri-alkoxy silane and at least one bi-alkoxy silane in the presence of emulsion-forming water (a) and surfactant mixture (c).

3. The aqueous silicone-containing emulsion of claim 2 wherein the siloxane has the general formula:

wherein n represents an integer of 3 to 9; and R 1 is independently selected from the group consisting of alkyl groups and aryl groups.

4. The aqueous silicone-containing emulsion of claim 2 wherein the siloxane has the general formula:

wherein R 1 is at least one selected from the group consisting of 1 to 10 carbon atom saturated linear hydrocarbon radicals, 1 to 10 carbon atoms saturated branched hydrocarbon radicals, 6 to 12 carbon atom substituted aromatic hydrocarbon radicals and 3 to 10 carbon atom saturated cycloaliphatic hydrocarbon radicals.

5. The aqueous silicone-containing emulsion of claim 2 wherein the cyclic siloxane is at least one selected from the group consisting of hexamethylcyclotrisiloxane (D 3 ), octamethylcyclotetrasiloxane (D 4 ), decamethylcyclopentrasiloxane (D 5 ), dodecamethylcyclohexasiloxane (D 6 ) and tetradecamethylcycloheptasiloxane (D 7 ).

6. The aqueous silicone-containing emulsion of claim 2 wherein the tri-alkoxy silane has the general formula;

R 3 Si(OR 4 ) 3 ,

wherein R 4 is unsubstituted alkyl groups and R 3 is an amine or epoxy.

7. The aqueous silicone-containing emulsion of claim 2 wherein the bi-alkoxy silane has the general formula;

R 2 R 3 Si(OR 4 ) 2 ,

wherein R 2 and R 4 are unsubstituted alkyl groups and R 3 is an amine or epoxy.

8. The aqueous silicone-containing emulsion of claim 1 wherein the cationic surfactant is a quaternary ammonium salt having the general formula:

R 5 R 6 R 7 R 8 N + X −

wherein R 5 , R 6 , R 7 , and R 8 are alkyl groups containing from 1 to 30 carbon atoms and X is hydroxide or halogen.

9. The aqueous silicone-containing emulsion of claim 8 wherein R 5 , R 6 , R 7 , and R 8 are alkyl groups derived from the group consisting of tallow, coconut oil, soy and mixtures thereof.

10. The aqueous emulsion silicone-containing emulsion of claim 1 wherein the nonionic surfactant has the general formula:

R 9 —O—(CH 2 CH 2 O) x —R 10 ,

wherein R 9 is a long chain alkyl group and R 10 is hydrogen or CH 3 and x is greater than or equal to 3 and less than or equal to 50.

11. The aqueous emulsion silicone-containing emulsion of claim 10 wherein the nonionic surfactant possesses a hydrophilic-lipophilic balance between 10 and 20.

12. The aqueous emulsion silicone-containing emulsion of claim 1 wherein the catalyst is a siloxane polymerization catalyst selected from the group consisting of base metal hydroxides and quaternary ammonium hydroxides.

13. The aqueous emulsion silicone-containing emulsion of claim 12 wherein the catalyst is at least one selected from the group consisting of potassium hydroxide, sodium hydroxide, lithium hydroxide, octadecyl trimethyl ammonium hydroxide; hexadecyl trimethyl ammonium hydroxide and tallow trimethyl ammonium hydroxide.

14. The aqueous emulsion silicone-containing emulsion of claim 2 wherein the siloxane ranges in amount from about 10 to about 70 weight percent of the total emulsion.

15. The aqueous emulsion silicone-containing emulsion of claim 2 wherein the siloxane ranges in amount from about 25 to about 60 weight percent of the total emulsion.

16. The aqueous emulsion silicone-containing emulsion of claim 1 wherein cationic surfactant ranges in amount from 0.05 to 30 weight percent of the total emulsion.

17. The aqueous emulsion silicone-containing emulsion of claim 1 wherein cationic surfactant ranges in amount from 0.5 to 20 weight percent of the total emulsion.

18. The aqueous emulsion silicone-containing emulsion of claim 1 wherein nonionic surfactant ranges in amount from 0.1 to 40 weight percent of the total emulsion.

19. The aqueous emulsion silicone-containing emulsion of claim 1 wherein nonionic surfactant ranges in amount from about 0.5 to about 30 weight percent of the total emulsion.

20. The aqueous emulsion silicone-containing emulsion of claim 2 wherein the tri-alkoxy silane ranges in amount from 0.1 to 5 weight percent of the total emulsion.

21. The aqueous emulsion silicone-containing emulsion of claim 17 wherein the bi-alkoxy silane ranges in amount from 0.1 to 5 weight percent of the total emulsion.

22. The aqueous emulsion silicone-containing emulsion of claim 1 wherein the catalyst ranges in amount from about 0.01 to about 30 weight percent of the total composition.

23. A method for preparing an aqueous silicone-containing emulsion comprising:

a) polymerizing a silicone possessing a substantially planar crosslinked structure in the presence of an emulsion-forming amount of water and a surfactant mixture of at least one cationic and at least one nonionic surfactant; and,

b) terminating the polymerization of step (a) to provide the desired silicone-containing emulsion,

wherein silicone is obtained from the copolymerization of (i) at least one cyclic and/or linear siloxane and (ii) at least one tri-alkoxy silane and at least one bi-alkoxy silane.

24. The method of claim 23 wherein the siloxane has the general formula:

wherein n represents an integer of 3 to 9; and R 1 is independently selected from the group consisting of alkyl groups and aryl groups.

25. The method of claim 23 wherein the siloxane has the general formula:

wherein R 1 is at least one selected from the group consisting of 1 to 10 carbon atom saturated linear hydrocarbon radicals, 1 to 10 carbon atoms saturated branched hydrocarbon radicals, 6 to 12 carbon atom substituted aromatic hydrocarbon radicals and 3 to 10 carbon atom saturated cycloaliphatic hydrocarbon radicals.

26. The method of claim 23 wherein the cyclic siloxane is at least one selected from the group consisting of hexamethylcyclotrisiloxane (D 3 ), octamethylcyclotetrasiloxane (D 4 ), decamethylcyclopentrasiloxane (D 5 ), dodecamethylcyclohexasiloxane (D 6 ) and tetradecamethylcycloheptasiloxane (D 7 ).

27. The method of claim 23 wherein the tri-alkoxy silane has the general formula:

R 3 Si(OR 4 ) 2

wherein R 4 is an unsubstituted alkyl groups and R 3 is an amine or epoxy.

28. The method of claim 23 wherein the bi-alkoxy silane has the general formula:

R 2 R 3 Si(OR 4 ) 2

wherein R 2 and R 4 are unsubstituted alkyl groups and R 3 is an amine or epoxy.

29. The method claim 23 wherein the cationic surfactant is a quaternary ammonium salt having the general formula:

R 5 R 6 R 7 R 8 N + X − ,

wherein R 5 , R 6 , R 7 , and R 8 are alkyl groups containing from 1 to 30 carbon atoms and X is hydroxide or halogen.

30. The method of claim 29 wherein R 5 , R 6 , R 7 , and R 8 are alkyl groups derived from the group consisting of tallow, coconut oil, soy and mixtures thereof.

31. The method of claim 23 wherein the nonionic surfactant has the general formula:

R 9 —O—(CH 2 CH 2 O) x —R 10 ,

wherein R 9 is a long chain alkyl group and R 10 is hydrogen or CH 3 and x is greater than or equal to 3 and equal to or less than 50.

32. The method of claim 31 wherein the nonionic surfactant possesses a hydrophilic-lipophilic balance between 10 and 20.

33. The method of claim 23 further comprises a siloxane polymerization catalyst selected from the group consisting of base metal hydroxides and quaternary ammonium hydroxides and mixtures thereof.

34. The method of claim 33 wherein the catalyst is at least one selected from the group consisting of potassium hydroxide, sodium hydroxide, lithium hydroxide, octadecyl trimethyl ammonium hydroxide, hexadecyl trimethyl ammonium hydroxide and tallow trimethyl ammonium hydroxide.

35. The method of claim 23 wherein the siloxane ranges in amount from 10 to 70 weight percent of the total emulsion.

36. The method of claim 23 wherein the siloxane ranges in amount from 25 to 60 weight percent of the total emulsion.

37. The method of claim 23 wherein cationic surfactant ranges in amount from 0.05 to 30 weight percent of the emulsion.

38. The method of claim 23 wherein cationic surfactant ranges in amount from about 0.5 to about 20 weight percent of the total emulsion.

39. The method of claim 23 wherein nonionic surfactant ranges in amount from about 0.1 to about 40 weight percent of the total emulsion.

40. The method of claim 23 wherein nonionic surfactant ranges in amount from about 0.5 to about 30 weight percent of the total emulsion.

41. The method of claim 23 wherein tri-alkoxy silane ranges in amount from about 0.01 to about 5 weight percent of the total emulsion.

42. The method of claim 23 wherein the bi-alkoxy silane ranges in amount from about 0.1 to about 5 weight percent of the total emulsion.

43. A textile coated with the aqueous silicone-containing emulsion of claim 1 .

44. A cotton fiber coated with the aqueous silicone-containing emulsion of claim 1 .

45. A fabric coated with the aqueous silicone-containing emulsion of claim 1 .

46. A non-woven fabric coated with the aqueous silicone-containing emulsion of claim 1 .

47. A textile coated with the aqueous silicone-containing emulsion prepared from the method of claim 23 .

48. A cotton fiber coated with the aqueous silicone-containing emulsion prepared from the method of claim 23 .

49. A fabric coated with the aqueous silicone-containing emulsion prepared from the method of claim 23 .

50. A non-woven fabric coated with the aqueous silicone-containing emulsion prepared from the method of claim 23 .

Assignments (17)
RELEASE OF SECURITY INTEREST Recorded Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
Reel/Frame 054372/0391 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →
SECURITY AGREEMENT Recorded Jul 1, 2009
From: MOMENTIVE PERFORMANCE MATERIALS, INC.; JUNIPER BOND HOLDINGS I LLC; JUNIPER BOND HOLDINGS II LLC; JUNIPER BOND HOLDINGS III LLC; JUNIPER BOND HOLDINGS IV LLC; MOMENTIVE PERFORMANCE MATERIALS CHINA SPV INC.; MOMENTIVE PERFORMANCE MATERIALS QUARTZ, INC.; MOMENTIVE PERFORMANCE MATERIALS SOUTH AMERICA INC.; MOMENTIVE PERFORMANCE MATERIALS USA INC.; MOMENTIVE PERFORMANCE MATERIALS WORLDWIDE INC.; MPM SILICONES, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 022902/0461 →
SECURITY AGREEMENT Recorded Jul 2, 2008
From: MOMENTIVE PERFORMANCE MATERIALS, INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 021184/0841 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2007
From: ZHENG, QUAN; HUANG, XUDONG; LI, TIANDONG
To: MOMENTIVE PERFORMANCE MATERIALS, INC.
Reel/Frame 019664/0813 →
Continuity (1)
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