IP Library Granted Patent US 9,505,971
Granted Patent B2
US 9,505,971 · App. 14/279,563 · Granted Nov 29, 2016

Stabilization of polyacrylamide emulsion formulations

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Quick Facts
Patent No.
US 9,505,971
App. No.
14/279,563
Granted
Nov 29, 2016
Kind
B2
Abstract

The current invention provides a method to form a stable blend of polyacrylamide water-in-oil emulsion and breaker surfactants such as silicon polyether copolymer and linear or branched alcohol ethoxylate surfactants. The composition can be employed, for example, as a friction reducing additive for water based fracturing fluid, or a drilling mud additive.

Claims (81)

1. A method of stabilizing a friction reducer composition comprising

(a) polyacrylamide emulsion; and,

(b) breaker surfactant selected from the group consisting of

(1) silicone polyether(s) defined by the formula:

Me 3 Si—O—SiMe(R)—O—SiMe 3 ,

wherein

R═(C 3 H 6 )O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c Z,

wherein

a=4-17,

b=0-26,

c=0-26, and

Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms;

(2) silicone polyether(s) defined by the formula:

Me 3 Si—[OSiMe 2 ] x —[O—SiMe(R)] y —O—SiMe 3 ,

wherein

x=0-74,

y=1-10,

R═(C 3 H 6 )O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c Z,

a=5-17,

b=0-26,

c=0-26, and

Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms; and,

(3) silicon polyether(s) defined by the formula:

Me 3 Si(C 2 H 4 )SiMe 2 (C 3 H 6 O)(C 2 H 4 O) x Z,

wherein

x=3-17, and Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms

said method comprising adding an effective amount of an organic additive with the formula R—O—R′, where

R is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-200 carbon atoms, and

R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-70 carbon atoms and optionally containing at least one of oxygen, nitrogen and sulphur heteroatoms, to the friction reducer composition, thereby stabilizing said friction reducer composition.

2. The method of claim 1 wherein said emulsion is water-in-oil emulsion.

3. The method of claim 1 wherein said polyacrylamide is an anionic polyacrylamide.

4. The method of claim 1 wherein

R is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-100 carbon atoms, and

R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms and optionally contains oxygen atoms.

5. The method of claim 4 wherein

R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms and optionally contains oxygen atoms.

6. The method of claim 5 wherein

R′ is —C(O)R″ wherein R″ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms.

7. The method of claim 1 wherein said organic additive is a fatty acid ester.

8. The method of claim 1 wherein said organic additive is 1 wt % to 6 wt % of the formulation.

9. The method of claim 1 wherein the said breaker surfactant is 1 wt % to 6 wt % of the friction reducer composition.

10. The method of claim 1 wherein said stabilized friction reducer composition is added to water and/or brine at a dosage rate of from 0.25 to 5 gallons to 1,000 gallons of water or brine.

11. A hydraulic fracturing operation utilizing the stabilized friction reducer composition produced by the method of claim 1 .

12. A drilling operation utilizing the stabilized friction reducer composition produced by the method of claim 1 .

13. A coil tubing operation utilizing the stabilized friction reducer composition produced by the method of claim 1 .

14. An acidizing operation utilizing the stabilized friction reducer composition produced by the method of claim 1 .

15. A stabilized friction reducer composition comprising

a. a polyacrylamide emulsion;

b. a breaker surfactant selected from the group consisting of

(1) silicone polether(s) defined by the formula:

Me 3 Si—O—SiMe(R)—O—SiMe 3 ,

wherein

R═(C 3 H 6 )O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c Z,

wherein

a=4-17,

b=0-26,

c=0-26, and

Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms:

(2) silicone polyether(s) defined by the formula:

Me 3 Si—[OSiMe 2 ] x —[O—SiMe(R)] y —O—SiMe 3 ,

wherein

x=0-74,

y=1-10,

R═(C 3 H 6 )O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c Z,

a=5-17,

b=0-26,

c=0-26, and

Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms; and,

and

(3) silicon polyether(s) defined by the formula:

Me 3 Si(C 2 H 4 )SiMe 2 (C 3 H 6 O)(C 2 H 4 O) x Z,

wherein

x=3-17, and Z is H, acetyl or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms; and,

c. an organic additive with the formula R—O—R′, where R is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-200 carbon atoms, and R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-70 carbon atoms and optionally containing at least one of oxygen, nitrogen and sulphur heteroatoms, and wherein the organic additive is present in an amount suitable to provide a stabilized friction reducer composition.

16. The stabilized friction reducer composition of claim 15 wherein

R is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-100 carbon atoms, and

R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms and optionally containing at least one oxygen atom.

17. The stabilized friction reducer composition of claim 16 wherein R′ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms and optionally contains at least one oxygen atom.

18. The stabilized friction reducer composition of claim 17 wherein R′ is —C(O)R″ wherein R″ is a monovalent, linear or branched, saturated or unsaturated hydrocarbon with 1-40 carbon atoms.

19. The stabilized friction reducer composition of claim 15 wherein said organic additive is a fatty acid ester.

20. The stabilized friction reducer composition of claim 15 wherein said organic additive is 1 wt % to 6 wt % of the formulation.

Assignments (18)
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0279 →
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 →
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 →
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 →
SECURITY INTEREST Recorded Jan 13, 2015
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 034759/0723 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2014
From: KUMAR, MUKESH; KOCZO, KALMAN; TERRACINA, JOHN
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 033027/0041 →