IP Library Granted Patent US 11,220,624
Granted Patent B2
US 11,220,624 · App. 16/523,642 · Granted Jan 11, 2022

Salt-tolerant, fast-dissolving, water-soluble rheology modifiers

Inventors: Christopher Steven Popeney (Sugar Land, TX); En-Wei Lin (Naperville, IL); Paul Joseph Zinn (Oswego, IL); Pious Kurian (Sugar Land, TX); Heinrich Enoch Bode (Aurora, IL)
Assignee: ChampionX USA Inc.
C09K8/68C08F220/56C08F2800/10
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Quick Facts
Patent No.
US 11,220,624
App. No.
16/523,642
Granted
Jan 11, 2022
Kind
B2
Abstract

Compounds, compositions and methods of use thereof are provided, the compounds comprising a hydrophobically modified polyelectrolyte comprising a nonionic monomer, an ionic monomer, a monomer having the structure of Formula 1, and a monomer having the structure of Formula 2, wherein R 1 , R 2 , R 3 , R 5 , R 6 , and R 7 are independently hydrogen, unsubstituted alkyl, substituted alkyl, carbonyl, carboxyl, aryl, or alkaryl; R 4 is linear C 3 to C 30 alkyl; R 8 is branched C 3 to C 30 alkyl; X 1 and X 2 are independently —C(O)O—, —C(O)NR 9 —, —O—, —C(R 9 ) 2 O—, -arylene-, -arylene-C(R 9 ) 2 O—, -arylene-C(R 9 ) 2 N(R 10 )— or -arylene-C(R 9 ) 2 N + (R 10 ) 2 —; R 9 and R 10 is independently hydrogen or a C 1 to C 4 alkyl; and wherein a molar ratio of the monomer of Formula 1 to the monomer of Formula 2 is from about 1.5:1 to about 15:1. The compounds are useful as viscosifying agents in oil and gas applications.

Claims (26)

1. A hydrophobically modified polyelectrolyte comprising a nonionic monomer, an anionic monomer, a monomer having the structure of Formula 1, and a monomer having the structure of Formula 2,

wherein

R 1 , R 2 , R 3 , R 5 , R 6 , and R 7 are independently hydrogen, unsubstituted alkyl, substituted alkyl, carbonyl, carboxyl, aryl, or alkaryl;

R 4 is linear C 3 to C 30 alkyl;

R 8 is branched C 3 to C 30 alkyl;

X 1 and X 2 are independently —C(O)O—, —C(O)NR 9 —, —O—, —C(R 9 ) 2 O—, arylene, arylene-C(R 9 ) 2 O—, arylene-C(R 9 ) 2 N(R 10 )—, arylene-C(R 9 ) 2 N + (R 10 ) 2 —; and

R 9 and R 10 is hydrogen or C 1 to C 4 alkyl;

wherein a molar ratio of the monomer of Formula 1 to the monomer of Formula 2 is from about 4:1 to about 15:1.

2. The polyelectrolyte of claim 1 , wherein the anionic monomer comprises 2-acrylamido-2-methyl-1-propanesulfonic acid, acrylic acid, methacrylic acid, 4-vinylbenzenesulfonic acid, a salt thereof, or a mixture thereof.

3. The polyelectrolyte of claim 2 , wherein the anionic monomer comprises 2-acrylamido-2-methyl-1-propanesulfonic acid, or a salt thereof.

4. The polyelectrolyte of claim 1 , wherein the nonionic monomer comprises acrylamide, N,N-dimethylacrylamide, N-vinylpyrrolidone, vinyl acetate, or a combination thereof.

5. The polyelectrolyte of claim 3 , wherein the nonionic monomer comprises acrylamide.

6. The polyelectrolyte of claim 1 , wherein the molar ratio of the monomer of Formula 1 to the monomer of Formula 2 is from about 4:1 to about 12:1.

7. The polyelectrolyte of claim 4 , wherein the molar ratio of the monomer of Formula 1 to the monomer of Formula 2 is from about 4:1 to about 10:1.

8. The polyelectrolyte of claim 5 , wherein the molar ratio of the monomer of Formula 1 to the monomer of Formula 2 is from about 6:1 to about 8:1.

9. The polyelectrolyte of claim 1 , wherein R 1 , R 2 , R 3 , R 5 , R 6 , and R 7 are independently hydrogen or C 1 to C 4 alkyl.

10. The polyelectrolyte of claim 8 , wherein R 3 and R 7 are hydrogen or methyl and R 1 , R 2 , R 5 , and R 6 are hydrogen.

11. The polyelectrolyte of claim 10 , wherein R 4 is linear C 8 to C 20 alkyl and R 8 is branched C 8 to C 20 alkyl.

12. The polyelectrolyte of claim 1 , wherein R 4 is linear C 10 to C 16 alkyl.

13. The polyelectrolyte of claim 12 , wherein R 8 is branched C 10 to C 18 alkyl.

14. The polyelectrolyte of claim 1 , wherein R 8 is branched C 10 to C 15 alkyl.

15. The polyelectrolyte of claim 1 , wherein R 9 is hydrogen and R 10 is C 1 to C 4 alkyl.

16. The polyelectrolyte of claim 1 , wherein X 1 and X 2 are —C(O)O—.

17. A composition comprising the polyelectrolyte of claim 1 in powder or granular form and a surfactant.

18. A method of increasing the viscosity of an aqueous solution comprising contacting the polyelectrolyte of claim 1 with the aqueous solution, thereby increasing the viscosity of the aqueous solution.

19. A hydrophobically modified polyelectrolyte comprising a nonionic monomer, an ionic monomer, lauryl acrylate, and isotridecyl acrylate.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 17, 2025
From: JPMORGAN CHASE BANK, N.A.
To: CHAMPIONX LLC; APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORP; HARBISON-FISCHER, INC.; NORRIS RODS, INC.,; NORRIS RODS, INC.,; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION
Reel/Frame 072004/0019 →
RELEASE OF SECURITY INTEREST Recorded Jun 7, 2022
From: BANK OF AMERICA, N.A.
To: CHAMPIONX USA INC.
Reel/Frame 060304/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 053849/0537 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2019
From: POPENEY, CHRISTOPHER STEVEN; LIN, EN-WEI; ZINN, PAUL JOSEPH; KURIAN, PIOUS; BODE, HEINRICH ENOCH
To: ECOLAB USA INC.
Reel/Frame 050078/0402 →