IP Library Granted Patent US 7,652,072
Granted Patent B2
US 7,652,072 · App. 11/427,913 · Granted Jan 26, 2010

Hydrolysis resistant organomodified disiloxane surfactants

Assignee: Momentive Performance Materials Inc.
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Quick Facts
Patent No.
US 7,652,072
App. No.
11/427,913
Granted
Jan 26, 2010
Kind
B2
Abstract

Compositions comprising an asymmetric disiloxane surfactant composition comprising a silicone composition comprising a silicone having the formula: MM′ where M or M′ comprises an alkylpolyalkyleneoxide bearing substituent selected from the group consisting of: R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 and R 12 SiR 5 R 6 (R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 ) that exhibit resistance to hydrolysis over a wide pH range.

Claims (44)

1. A silicone composition comprising a silicone having the formula:

MM′

where

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

M′=R 4 R 5 R 6 SiO 1/2 ;

wherein R 1 is R 7 where R 7 has the formula R 8 R 9 R 10 SiR 12 with R 8 , R 9 , and R 10 each being methyl, and R 12 is a divalent hydrocarbon radical having 2 carbon atoms,

R 2 and R 3 are each independently selected from the group of from 1 to 6 carbon atom monovalent hydrocarbon radicals or R 1 , with R 4 being an alkylpolyalkyleneoxide bearing substituent selected from the group consisting of:

R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 and

R 12 SiR 5 R 6 (R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 )

where R 13 is a divalent linear or branched hydrocarbon radical having the structure:

—CH 2 —CH(R 15 )(R 16 ) d O—

where R 15 is H or methyl; R 16 is a divalent alkyl radical of 1 to 6 carbons where the subscript d is 0 or 1;

R 14 is selected from the group consisting of H, monovalent hydrocarbon radicals of from 1 to 6 carbon atoms and acetyl where the subscripts a, b and c are zero or positive and satisfy the following relationships:

2≦ a+b+c≦ 20 with a ≧2,

and R 5 and R 6 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 4 .

2. The composition of claim 1 where R 15 is hydrogen.

3. The composition of claim 1 where R 2 is methyl.

4. The composition of claim 3 where R 15 is hydrogen.

5. A silicone composition comprising a silicone having the formula:

MM′

where

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

M′=R 4 R 5 R 6 SiO 1/2 ;

wherein R 1 is R 7 where R 7 has the formula R 8 R 9 R 10 SiR 12 with R 8 , R 9 , and R 10 each being methyl, and R 12 is a divalent hydrocarbon radical having 2 carbon atoms,

R 2 and R 3 are each independently selected from the group of from 1 to 6 carbon atom monovalent hydrocarbon radicals or R 1 , with R 4 being an alkylpolyalkyleneoxide bearing substituent selected from the group consisting of:

R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 and

R 12 SiR 5 R 6 (R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14 )

where R 13 is a divalent linear or branched hydrocarbon radical having the structure:

—CH 2 —CH(R 15 )(R 16 ) d O—

where R 15 is H or methyl; R 16 is a divalent alkyl radical of 1 to 6 carbons where the subscripted is 0 or 1;

R 14 is selected from the group consisting of H, monovalent hydrocarbon radicals of from 1 to 6 carbon atoms and acetyl where the subscripts a, b and c are zero or positive and satisfy the following relationships:

2≦ a+b+c≦ 20 with a≧ 2,

and R 5 and R 6 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 4 wherein said silicone composition has an enhanced resistance to hydrolysis.

6. The composition of claim 5 where R 15 is hydrogen.

7. The composition of claim 5 where R 2 is methyl.

8. The composition of claim 7 where R 15 is hydrogen.

9. An aqueous emulsion wherein the discontinuous phase comprises water and the continuous phase comprises the composition of claim 1 .

10. An aqueous emulsion wherein the discontinuous phase comprises water and the continuous phase comprises the composition of claim 5 .

11. An aqueous emulsion wherein the continuous phase comprises water and the discontinuous phase comprises the composition of claim 1 .

12. An aqueous emulsion wherein the continuous phase comprises water and the discontinuous phase comprises the composition of claim 5 .

13. A non-aqueous emulsion wherein the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of claim 1 .

14. A non-aqueous emulsion wherein the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of claim 5 .

15. A non-aqueous emulsion wherein the continuous phase comprises a non-aqueous hydroxylic solvent and the discontinuous phase comprises the composition of claim 1 .

16. A non-aqueous emulsion wherein the continuous phase comprises a non-aqueous hydroxylic solvent and the discontinuous phase comprises the composition of claim 5 .

Assignments (23)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
Reel/Frame 054387/0001 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
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
Reel/Frame 035137/0263 →
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 034066/0662 →
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 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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2008
From: GENERAL ELECTRIC COMPANY
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 020742/0608 →
SECURITY AGREEMENT Recorded Jul 3, 2007
From: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 019511/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2006
From: LEATHERMAN, MARK D.; POLLICELLO, GEORGE A.; RAJARAMAN, SURESH K.
To: GENERAL ELECTRIC COMPANY
Reel/Frame 017949/0251 →
Continuity (3)
Continuation In Part 1130010000 · Dec 13, 2005
Provisional Application 6072640900 · Oct 13, 2005
Related Publication 20070086968A1 · Apr 19, 2007