IP Library Granted Patent US 8,263,669
Granted Patent B2
US 8,263,669 · App. 12/810,976 · Granted Sep 11, 2012

Hydrolysis resistant organomodified trisiloxane ionic surfactants

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Quick Facts
Patent No.
US 8,263,669
App. No.
12/810,976
Granted
Sep 11, 2012
Kind
B2
Abstract

The present invention provides for a composition comprising a siloxane having the formula: M 1 D M 2 wherein M 1 =(R 1 )(R 2 )(R 3 )SiO 1/2 ; M 2 =(R 4 )(R 5 )(R 6 )SiO 1/2 and D=(R 7 )(Z)SiO 2/2 where R 1 , R 2 , R 3 R 4 , R 5 , R 6 and R 7 are each independently selected from the group consisting of 1 to 4 carbon monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 4 to 9 carbons containing an aryl group; Z is a pendant hydrophilic ionic group selected from the group consisting of R 8 —R A , R 9 R c and R 10 —R Z ; R A being an anionic substituent, R c a cationic substituent or R z a zwitterionic substituent on the D group wherein the composition is resistant to hydrolysis under either basic or acidic conditions.

Claims (48)

1. A composition comprising a siloxane having the formula:

M 1 D M 2

wherein

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

M 2 =(R 4 )(R 5 )(R 6 )SiO 1/2 and

D=(R 7 )(Z)SiO 2/2

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from the group consisting of 1 to 4 carbon monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 4 to 9 carbons containing an aryl group;

Z is a hydrophilic substituent R 9− R c ;

R 9 is a monovalent radical selected from the group consisting of R 16 (O) w (R 17 ) x and R 18 O(C 2 H 4 O) d (C 3 H 6 O) e (C 4 H 8 O) f CH 2 CH(OH)CH 2 ;

where R 16 and R 17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms, that may each be optionally substituted with one or more OH radicals;

R 18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are zero or 1;

the subscripts d, e and f are zero or positive and satisfy the following relationships:

1 ≦d+e+f≦ 10 with d≧ 1;

R C is selected from the group consisting of N(R 19 )(R 20 ),

where R 19 and R 20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R 26 N(R 29 )(R 30 ), and —R 27 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 28 ;

the subscripts g, h and i are zero or positive and satisfy the following relationships:

1 ≦g+h+i≦ 10 with g≧ 1;

R 21 , R 23 , R 24 , R 25 are independently selected from the groups consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons;

R 22 is H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, or —R 31 O(C 2 H 4 O) j (C 3 H 6 O) k (C 4 H 8 O) l R 32 ;

the subscripts j, k and l are zero or positive and satisfy the following relationships:

1 ≦j+k+l≦ 10 with j≧ 1;

R 26 is a divalent hydrocarbon radical of 1 to 6 carbons that may be optionally substituted with a heterocyclic group containing nitrogen, sulfur, oxygen or combinations thereof or R 33 O(C 2 H 4 O) m (C 3 H 6 O) n (C 4 H 8 O) o R 34 ;

the subscripts m, n and o are zero or positive and satisfy the following relationships:

1 ≦m+n+o≦ 10 with m≧ 1;

R 29 and R 30 are independently selected from the group consisting of H or a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons;

R 27 , R 31 and R 33 are divalent radicals independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;

R 28 is H, a monovalent hydrocarbon radical of 1 to 6 carbons, or N(R 35 )(R 36 );

R 32 and R 34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R 37 N(R 38 )(R 39 ); where R 37 is a divalent hydrocarbon radical of 1 to 6 carbons; R 35 , R 36 , R 38 and R 39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons.

2. The composition of claim 1 where

R 1 and R 4 are propyl, isopropyl, butyl, sec-butyl, iso-butyl, or tert-butyl;

R 2 , R 3 , R 5 , R 6 , R 7 is methyl;

R 16 is —H 2 CH 2 CH 2 —;

R 17 is CH 2 CH(OH)CH 2 —;

R 18 is —CH 2 CH 2 CH 2 —;

R 19 and R 20 is H, methyl, ethyl, propyl, isopropyl or—R 27 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 28 ;

R 27 is —CH 2 CH 2 CH 2 —, H or methyl;

R 21 and R 23 are H;

R 22 =H, methyl or —R 31 O(C 2 H 4 O) j (C 3 H 6 O) k (C 4 H 8 O) l R 32 ;

R 31 is —CH 2 CH 2 CH 2 —; j is 1-5, k and l=0;

R 32 is H or methyl; R 24 and R 25 are H.

3. An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the composition of claim 1 .

4. An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the composition of claim 2 .

5. An aqueous emulsion where the discontinuous phase comprises the composition of claim 1 and the continuous phase comprises water.

6. An aqueous emulsion where the discontinuous phase comprises the composition of claim 2 and the continuous phase comprises water.

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

8. A non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of claim 2 .

9. A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the composition of claim 1 .

10. A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the composition of claim 2 .

Assignments (11)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0281 →
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 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
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 034113/0331 →
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 →