Polyanionic surfactants and methods of making and using thereof

Patent metadata

Field	Value
Publication number	US-12371619-B2
Application number	US-202117920975-A
Country	US
Kind code	B2
Filing date	Apr 26, 2021
Priority date	Apr 24, 2020
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

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.

First claim

The invention claimed is:

1. A surfactant defined by Formula I below

or a salt thereof, wherein
HG represents a head group comprising from 1-3 carboxylate moieties;
R 1 represents a C7-C28 alkyl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, a C7-C28 alkylaryl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, a C7-C28 alkenyl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, or a C7-C28 alkenylaryl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy;
n is an integer from 1 to 8;
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
+
n

)

=
ε

wherein w and n are as defined above in Formula I; and q is an integer equal to the number of carbon atoms in R′; and wherein ε is from 0.5 to 6-4.

5. The surfactant of claim 1 , wherein the head group is defined by the formula below

or a salt thereof, where m is an integer from 1 to 6.

6. The surfactant of claim 1 , wherein the head group is defined by the formula below

or a salt thereof, where p is an integer from 1 to 5.

7. The surfactant of claim 1 , wherein the surfactant is defined by Formula IA below

or a salt thereof, wherein
HG represents a head group comprising from 1-3 carboxylate moieties;
n is an integer from 1 to 8;
R 1 represents a C7-C28 alkyl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, a C7-C28 alkylaryl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, a C7-C28 alkenyl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy, or a C7-C28 alkenylaryl group substituted with from one to three pendant polycarboxylate moieties and optionally with from one to three substituents selected from hydroxy and alkoxy;
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. The surfactant of claim 1 , wherein each of the pendant polycarboxylate moieties comprises a pendant bicarboxylate moiety.

14. The surfactant of claim 1 , wherein each of the pendant polycarboxylate moieties is defined by the formula below

or a salt thereof.

15. The surfactant of claim 1 , where R 1 comprises one of the following

or a salt thereof, wherein
a is an integer from 0 to 32; and
b is an integer from 0 to 32,
with the proviso that the sum of a and b is from 4 to 32.

16. An aqueous composition comprising water and the surfactant defined by claim 1 .

17. A method for treating a subterranean formation, the method comprising introducing an aqueous fluid comprising water and the surfactant defined by claim 1 through a wellbore into the subterranean formation.

18. A surfactant mixture comprising:
(a) a first surfactant defined by Formula II or a salt thereof;

(b) a second surfactant defined by Formula III or a salt thereof;

wherein
e is an integer from 0 to 32 and f is an integer from 0 to 32, with the proviso that the sum of e and f is from 4 to 32;
AO represents, individually for each occurrence, an alkyleneoxy group selected from an ethoxy group, a propoxy group, or a butoxy group;
w is an integer from 1 to 110; and
m is an integer from 1 to 6.

19. The surfactant of claim 18 , wherein the sum of e and f is from 8 to 22.

20. An aqueous composition comprising water and the surfactant mixture defined by claim 18 .

Assignees

• Chevron Usa Inc

Inventors

• Pinnawala Gayani W
• Palayangoda Sujeewa S
• Winslow Gregory A
• Dwarakanath Varadarajan

Classifications

• C09K8/68

  containing organic compounds · CPC title

• C09K8/584 Primary

  characterised by the use of specific surfactants · CPC title

• C09K23/12

  Sulfonates of aromatic or alkylated aromatic compounds · CPC title

• C09K8/86

  containing organic compounds · CPC title

• C09K8/602

  containing surfactants · CPC title