IP Library Patent Application 12810663
Patent Application
App. No. 12/810,663

MIXTURES OF HYDROLYSIS RESISTANT ORGANOMODIFIED TRISILOXANE IONIC SURFACTANTS

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Quick Facts
Patent No.
US None
App. No.
12/810,663
Filed
Oct 4, 2010
Art Unit
1613
USPC
424/400
Abstract

The present invention provides for a mixture 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 , W 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 and an additional component selected from the group consisting of agricultural components, coating components, personal care components, home care components, oil or gas treating components, water processing components, and pulp or paper treating components, wherein said mixture has an enhanced resistance to hydrolysis.

Claims (108)

1 . A mixture comprising:

a) a siloxane having the formula:

M 1 DM 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 selected from the group consisting of R 8 —R A , R 9 —R C , and R 10 —R Z ;

R 8 is a monovalent radical

of

R 11 (O) t (R 12 ) u (O) v , R 13 —CHCH 2 CH(OH)CH(O—)CH 2 CH 2 ; and

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

where R 11 and R 12 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 13 is a divalent hydrocarbon group of 2 to 4 carbon atoms;

R 14 is a divalent hydrocarbon group of 1 to 6 carbons, that may each be optionally branched; subscripts t, u and v are zero or 1; t

the subscripts a, b and c are zero or positive and satisfy the following relationships:

1 ≦a+b+c≦ 10 with a≧ 1;

R A is a monovalent radical selected from the group consisting of SO 3 M K , —C(═O)CH 2 CH(R 15 )COOM K ; —PO 3 H M K ; COOM K ; where R 15 is H or SOM K ;

M K is a cation selected from the group consisting of Na + , K + , Ca 2+ , NH 4 + , Li + , and monovalent ammonium ions derived from mono-, di- and trialkylamines of 2 to 4 carbons or mono-, di- and trialkanolamines of 2 to 4 carbons;

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;

R 10 is a monovalent radical selected from the group consisting of R 40 (O) y (R 41 ) z and R 42 O(C 2 H 4 O) p (C 3 H 6 O) q (C 4 H 8 O) r CH 2 CH(OH)CH 2 ;

where R 40 and R 41 are each independently selected from the group consisting of a divalent hydrocarbon bridging group of 1 to 4 carbon atoms, that may be each optionally substituted with one or more OH radicals;

R 42 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts y and z are zero or 1;

the subscripts p, q and r are zero or positive and satisfy the following relationships:

1 ≦p+q+r≦ 10 with p≧ 1.

R Z is a monovalent radical selected from the group consisting of

N—(R 43 )(R 44 ) α R 45 SO 3 − (M K ) β , N—(R 46 )(R 47 ) γ R 48 COO − (M K ) δ ,

N + —(R 49 )(R 50 )R 51 OP(═O)(A)(B) or,

(—C(═O)N(R 52 )R 53 N—(R 54 )(R 55 )) + —(R 56 OP(═O)(A)(B))(X) ε ;

where R 43 , R 44 , R 46 , R 47 , R 49 , R 50 , R 52 , R 54 and R 55 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and an alkanolamine group of 2 to 4 carbons;

R 45 is a divalent group of 3 to 4 carbons;

the subscripts α, β, γ and δ are zero or 1 subject to the following relationships:

α+β=1 and γ+δ=1;

R 48 and R 51 are independently a divalent group of 1 to 4 carbons;

R 53 and R 56 are each independently a divalent group of 2 to 4 carbons;

A and B are selected from the group consisting of O − and OM K ;

X is an anion selected from the group of anions consisting of Cl, Br, and I;

and the subscript ε is 0, 1 or 2; and

b) an additional component selected from the group consisting of agricultural components, coating components, personal care components,

home care components, oil or gas treating components, water processing components, and pulp or paper treating components,

wherein said mixture has an enhanced resistance to hydrolysis.

2 . The mixture 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 11 is —CH 2 CH 2 CH 2 —; R 12 is —CH 2 CH(OH)CH 2 —;

R 13 is —H 2 CH 2 —; R 14 is —CH 2 CH 2 CH 2 —, —CH(CH 3 )CH 2 CH 2 —, or —CH 2 CH(CH 3 )CH 2 —;

R 15 ═H;

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;

R 40 is —CH 2 CH 2 CH 2 —; R 41 is —H 2 CH(CH 3 )CH 2 —;

R 42 is —CH 2 CH 2 CH 2 —;

R 43 and R 44 are H or methyl;

R 45 is —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —;

R 46 and R 47 are H or methyl;

R 48 is —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —;

R 49 and R 50 are H or methyl; and

R 52 , R 54 and R 55 are H or methyl.

3 . The mixture of claim 2 wherein Z is R 8 —R A .

4 . The mixture of claim 2 wherein Z is R 9 —R C .

5 . The mixture of claim 2 wherein Z is R 10 —R Z .

6 . An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the mixture of claim 1 .

7 . An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the mixture of claim 2 .

8 . An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the mixture of claim 3 .

9 . An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the mixture of claim 4 .

10 . An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises the mixture of claim 5 .

11 . An aqueous emulsion where the discontinuous phase comprises the mixture of claim 1 and the continuous phase comprises water.

12 . An aqueous emulsion where the discontinuous phase comprises the mixture of claim 2 and the continuous phase comprises water.

13 . An aqueous emulsion where the discontinuous phase comprises the mixture of claim 3 and the continuous phase comprises water.

14 . An aqueous emulsion where the discontinuous phase comprises the mixture of claim 4 and the continuous phase comprises water.

15 . An aqueous emulsion where the discontinuous phase comprises the mixture of claim 5 and the continuous phase comprises water.

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

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

18 . A non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the mixture of claim 3 .

19 . A non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the mixture of claim 4 .

20 . A non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the mixture of claim 5 .

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

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

23 . A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the mixture of claim 3 .

24 . A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the mixture of claim 4 .

25 . A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the mixture of claim 5 .

Assignments (15)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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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
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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.
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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.
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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
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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
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SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
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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
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To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
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SECURITY AGREEMENT Recorded Apr 29, 2011
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
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ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2010
From: LEATHERMAN, MARK D; POLICELLO, GEORGE A.; PENG, WENQING N.; ZHENG, LIPING; WAGNER, ROLAND; RAJARAMAN, SURESH K; ZIJUN, XIA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
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