IP Library › Granted Patent US 12,286,588
Granted Patent B2
US 12,286,588 · App. 17/920,974 · Granted Apr 29, 2025

Polyanionic surfactants and methods of making and using thereof

Inventors: Gayani W. Pinnawala (San Ramon, CA); Sujeewa S. Palayangoda (San Ramon, CA); Gregory A. Winslow (San Ramon, CA); Varadarajan Dwarakanath (San Ramon, CA)
Assignee: CHEVRON U.S.A. INC.
C09K8/584C09K8/602C09K8/68C09K23/12
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Quick Facts
Patent No.
US 12,286,588
App. No.
17/920,974
Granted
Apr 29, 2025
Kind
B2
Abstract

The present disclosure is directed to polyanionic surfactants, surfactant mixtures, compositions derived thereof, and uses thereof in hydrocarbon recovery. Methods of making polyanionic surfactants are also described.

Claims (68)

1. A surfactant defined by Formula I below

or a salt thereof, wherein

p is an integer from 1 to 5;

R 1 represents a C8-C50 alkyl group;

AO represents, individually for each occurrence, an alkyleneoxy group selected from an ethoxy group, a propoxy group, or a butoxy group; and

w is an integer from 1 to 110.

2. The surfactant of claim 1 , wherein AO represents, individually for each occurrence, an alkyleneoxy group selected from an ethoxy group or a propoxy group.

3. The surfactant of claim 1 , wherein w is an integer from 20 to 110.

4. The surfactant of claim 1 , wherein ϵ is defined by the formula below

w

(

q

+

p

)

=

ε

wherein

w is the number of alkyleneoxy groups and p is as defined above in Formula I; and

q is an integer equal to the number of carbon atoms in R 1 ; and

wherein ϵ is from 0.5 to 6.

5. The surfactant of claim 1 , wherein R 1 represents a branched C8-C50 alkyl group.

6. The surfactant of claim 1 , wherein R 1 represents a linear C8-C50 alkyl group.

7. The surfactant of claim 1 , wherein AO is defined by the formula below

wherein

BO represents a butyleneoxy group;

PO represents a propyleneoxy group;

EO represents an ethyleneoxy group;

x is an integer from 1 to 65;

y is an integer from 0 to 65; and

z is an integer from 0 to 45.

8. The surfactant of claim 7 , wherein z is 0.

9. The surfactant of claim 7 , wherein x is from 5 to 50.

10. The surfactant of claim 7 , wherein y is from 5 to 45.

11. The surfactant of claim 7 , wherein the ratio of x: (y+z) is from 0.5:1 to 2:1.

12. The surfactant of claim 7 , wherein y is 0 and z is 0.

13. An aqueous composition comprising water and a surfactant defined by claim 1 .

14. The composition of claim 13 , wherein the composition further comprises one or more co-surfactants.

15. The composition of claim 14 , wherein the one or more co-surfactants comprise an anionic surfactant, a non-ionic surfactant, a cationic surfactant, a zwitterionic surfactant, or any combination thereof;

wherein the anionic surfactant comprises a sulfonate, a disulfonate, a sulfate, a disulfate, a sulfosuccinate, a disulfosuccinate, a carboxylate, a dicarboxylate, or any combination thereof,

wherein the anionic surfactant comprises one of the following:

a branched or unbranched C6-C32: PO(0-65):EO(0-100)-carboxylate;

a C8-C30 alkyl benzene sulfonate (ABS);

a sulfosuccinate surfactant;

a surfactant defined by the formula below

R 1 -R 2 -R 3

wherein

R 1 comprises a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 6-32 carbon atoms and an oxygen atom linking R 1 and R 2 ;

R 2 comprises an alkoxylated chain comprising at least one oxide group selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and any combination thereof; and

R 3 comprises a branched or unbranched hydrocarbon chain comprising 2-12 carbon atoms and from 2 to 5 carboxylate groups;

a surfactant defined by the formula below

wherein

R 4 is, individually for each occurrence, a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 6-32 carbon atoms; and

M represents a counterion;

or any combination thereof;

wherein the non-ionic surfactant comprises a branched or unbranched C6-C32:PO(0-65):EO(0-100).

16. A method for treating a subterranean formation, the method comprising

introducing an aqueous composition defined by claim 13 through a wellbore into the subterranean formation.

17. The method of claim 16 , wherein the method comprises a method for stimulating the subterranean formation that comprises:

(a) injecting the aqueous fluid through the wellbore into the subterranean formation;

(b) allowing the aqueous fluid to imbibe into a rock matrix of the subterranean formation for a period of time; and

(c) producing fluids from the subterranean formation through the wellbore.

18. The method of claim 16 , wherein the method comprises a method for fracturing the subterranean formation that comprises:

(a) injecting the aqueous fluid into the subterranean formation through the wellbore at a sufficient pressure to create or extend at least one fracture in a rock matrix of the subterranean formation in fluid communication with the wellbore.

19. The method of claim 16 , wherein the wellbore comprises an injection wellbore, and wherein the method comprises a method for hydrocarbon recovery that comprises:

(a) injecting the aqueous fluid through the injection wellbore into the subterranean formation; and

(b) producing fluids from a production wellbore spaced apart from the injection wellbore a predetermined distance and in fluid communication with the subterranean formation;

wherein injection of the aqueous fluid increases a flow of hydrocarbons to the production wellbore.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2023
From: PINNAWALA, GAYANI W.; PALAYANGODA, SUJEEWA S.; WINSLOW, GREGORY A.; DWARAKANATH, VARADARAJAN
To: CHEVRON U.S.A. INC.
Reel/Frame 065047/0779 →
Continuity (2)
Provisional Application 63015394 · Apr 24, 2020
Related Publication 20230167353A1 · Jun 1, 2023
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