IP Library Granted Patent US 9,243,142
Granted Patent B2
US 9,243,142 · App. 13/297,926 · Granted Jan 26, 2016

Association product of amino functional hydrophobic polymers with hydrophilic polymers containing acid groups, methods of preparation, and applications for employing the same

Inventors: Anne Dussaud (Tarrytown, NY); Ning Lu (Chappaqua, NY)
Assignee: Momentive Performance Materials Inc.
C08L79/02A61K8/042A61K8/37A61K8/8152A61K8/898A61Q5/12C08L71/02C08L83/08C08L83/12A61K2800/48A61K2800/594C08G2650/50
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Quick Facts
Patent No.
US 9,243,142
App. No.
13/297,926
Granted
Jan 26, 2016
Kind
B2
Abstract

There is provided herein a composition comprising the non-covalent bonded reaction product of a hydrophilic polymer containing an acid functional group and a hydrophobic polymer which contains an amine group bound directly to the hydrophobic polymer backbone; and, optionally a diluent, as well as a process of making such a composition.

Claims (47)

1. A composition comprising a non-covalent bonded reaction product of (A) a hydrophilic polymer containing an acid functional group and (B) a hydrophobic polymer which contains an amine group bound directly to the hydrophobic polymer backbone and which either does not contain an ethylene oxide moiety or contains an ethylene oxide moiety to propylene oxide moiety in a ratio of less than 3,

wherein the non-covalent bonded reaction product is prepared by

method (a) which comprises

(a-i) blending hydrophilic polymer (A) and hydrophobic polymer (B) in a molar ratio of amine:acid from 0.01:1 to 1:1 in a non-aqueous medium at the temperature in the range of 30° C. to 200° C. for a period of from about 1 minute to about 120 minutes to produce a blend, and

(a-ii) cooling the blend obtained from step (a-i) to room temperature to provide the non-covalent bonded reaction product; or

method (b) which comprises

(b-i) blending hydrophilic polymer (A) and hydrophobic polymer (B) in a molar ratio of amine:acid from 0.01:1 to 0.2:1 in a non-aqueous medium at the temperature in the range of 30° C. to 200° C. for a period of from about 1 minute to about 120 minutes to produce a blend,

(b-ii) adding an aqueous base solution to the blend obtained from step (b-i) at the temperature in the range of 30° C. to 95° C. to produce a mixture, and

(b-iii) cooling the mixture obtained from step (b-ii) to room temperature to provide the non-covalent bonded reaction product;

wherein the hydrophobic polymer which contains an amine group bound directly to the hydrophobic polymer backbone is

an amino silicone copolymer with a (ABA) structure where B is the siloxane block, resulting from the reaction of:

R 1 R 2 NH

where R 1 ═R 3 (OC a H 2a ) m — and where R 3 ═(C n H 2n+1 )— and where n is an integer of from 1 to 30,

or where R 3 ═(C n H 2n−1 )— where n is an integer of from 2 to 30,

or where R 3 ═(C n H 2n−3 )— where n is an integer of from 4 to about 30,

and m=0 or an integer of from 1 to 200, and a is an integer of from 2 to 4,

where R 2 ═H or R 4 (OC c H 2c ) o —

where R 4 ═(C q H 2q+1 )— where q is an integer of from 1 to 30, or

where R 4 ═(C q H 2q−1 )— where q is an integer of from 2 to about 30, or

where R 4 ═(C q H 2q−3 )— where q is an integer of from 4 to 30, and

o=0 or an integer of from 1 to 200 and,

c is an integer of from 2 to 4; and

wherein q is an integer of from 2 to 1000.

2. The composition of claim 1 wherein acid functional group of the hydrophilic polymer is at least one of a carboxylic group, a sulfonic group and a phosphonic group.

3. The composition of claim 1 wherein the hydrophilic polymer containing an acid functional group is selected from the group consisting of:

(I) polyacrylates polymers;

(II) homopolymers containing monomers containing sulfonic groups;

(III) copolymers containing monomers containing sulfonic groups; and

(IV) polysaccharides containing acidic groups.

4. The composition of claim 1 wherein the hydrophilic polymer containing an acid functional group and a hydrophobic polymer which contains an amine group bound directly to the hydrophobic polymer backbone are present in an amount such that there is an amine/acid ratio of from about 1:20 to about 1:1.

5. The composition of claim 1 wherein the composition is other than a fabric treatment composition.

6. The composition of claim 1 wherein the non-covalent bonded reaction product comprises at least one hydrogen bond or at least one ionic bond.

7. An aqueous emulsion comprising the composition of claim 1 .

8. A composition selected from the group consisting of a personal care composition, a cosmetic composition, a textile composition, an oil extraction composition, a coating composition, a paint composition, an agriculture composition, a lubrication composition, a composition requiring irreversible thickening, and an emulsification composition, wherein the composition comprises the composition of claim 1 .

9. A personal care composition comprising the composition of claim 1 .

10. A hair care or skin care composition comprising the composition of claim 1 .

11. The composition of claim 1 wherein the subscript q in

is an integer of from 10 to 500.

12. A process of making a composition comprising non-covalently reacting a hydrophilic polymer containing an acid functional group and; a hydrophobic polymer which contains an amine group bound directly to the hydrophobic polymer backbone and which either contains no ethylene oxide moieties or contains an ethylene oxide moiety to propylene oxide moiety ratio of less than 3

wherein the non-covalent bonded reaction product is prepared by

method (a) which comprises

(a-i) blending hydrophilic polymer (A) and hydrophobic polymer (B) in a molar ratio of amine:acid from 0.01:1 to 1:1 in a non-aqueous medium at the temperature in the range of 30° C. to 200° C. for a period of from about 1 minute to about 120 minutes to produce a blend, and

(a-ii) cooling the blend obtained from step (a-i) to room temperature to provide the non-covalent bonded reaction product; or

method (b) which comprises

(b-i) blending hydrophilic polymer (A) and hydrophobic polymer (B) in a molar ratio of amine:acid from 0.01:1 to 0.2:1 in a non-aqueous medium at the temperature in the range of 30° C. to 200° C. for a period of from about 1 minute to about 120 minutes to produce a blend,

(b-ii) adding an aqueous base solution to the blend obtained from step (b-i) at the temperature in the range of 30° C. to 95° C. to produce a mixture, and

(b-iii) cooling the mixture obtained from step (b-ii) to room temperature to provide the non-covalent bonded reaction product.

Assignments (22)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 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 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 034066/0570 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2012
From: DUSSAUD, ANNE; LU, NING
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 027626/0755 →
Continuity (1)
Related Publication 20130121948A1 · May 16, 2013