IP Library Granted Patent US 8,008,231
Granted Patent B2
US 8,008,231 · App. 11/427,961 · Granted Aug 30, 2011

Extreme environment surfactant compositions comprising hydrolysis resistant organomodified disiloxane surfactants

Assignee: Momentive Performance Materials Inc.
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Quick Facts
Patent No.
US 8,008,231
App. No.
11/427,961
Granted
Aug 30, 2011
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 (39)

1. An agricultural composition comprising:

a) 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 ;

with R 1 selected from the group consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms and R 7 , where R 7 is selected from the group consisting of

R 8 R 9 R 10 SiR 12 and (R 4 R 5 R 6 )SiR 12

with R 8 , R 9 , and R 10 each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon radicals having from 6 to 13 carbon atoms and R 12 is a divalent hydrocarbon radical having from 1 to 3 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 an alkylpolyalkyleneoxide of the general formula:

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 may be 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 ; and

b) an agriculturally active component selected from the group consisting of pesticides, fungicides, insecticides, herbicides and fertilizers wherein said agricultural composition has an enhanced resistance to hydrolysis.

2. The composition of claim 1 where R 1 is iso-propyl.

3. The composition of claim 1 where R 1 is iso-butyl.

4. The composition of claim 1 where R 1 is tert-butyl.

5. The composition of claim 1 where 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 methyl and R 12 is a divalent hydrocarbon radical having 2 carbon atoms.

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

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

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

9. The composition of claim 2 where R 2 is methyl.

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

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

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

13. The composition of claim 4 where R 2 is methyl.

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

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

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

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

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

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

20. The composition of claim 1 wherein the pesticide is selected from the group consisting of rodenticides, insecticides, miticides, fungicides, and herbicides.

21. The composition of claim 1 wherein the herbicide is selected from the group consisting of phenoxy acetic acids, phenoxy propionic acids, phenoxy butyric acids, benzoic acids, triazines and s-triazines, substituted ureas, uracils, bentazon, desmedipham, methazole, phenmedipham, pyridate, amitrole, clomazone, fluridone, norflurazone, dinitroanilines, isopropalin, oryzalin, pendimethalin, prodiamine, trifluralin, glyphosate, sulfonylureas, imidazolinones, clethodim, diclofop-methyl, fenoxaprop-ethyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop, sethoxydim, dichlobenil, isoxaben, and bipyridylium compounds.

Assignments (18)
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 →
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 - 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 →
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 →
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 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2008
From: GENERAL ELECTRIC COMPANY
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 021049/0754 →
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.; POLICELLO, GEORGE A.; RAJARAMAN, SURESH K.
To: GENERAL ELECTRIC COMPANY
Reel/Frame 017950/0956 →
Continuity (3)
Continuation In Part 11301707 · Dec 13, 2005
Provisional Application 60726409 · Oct 13, 2005
Related Publication 20070087937A1 · Apr 19, 2007