Polyanionic surfactants and methods of making and using thereof

Patent metadata

Field	Value
Publication number	US-2025354063-A1
Application number	US-202519282657-A
Country	US
Kind code	A1
Filing date	Jul 28, 2025
Priority date	Apr 24, 2020
Publication date	Nov 20, 2025
Grant date	—

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

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 any of claims 1-2 , wherein w is an integer from 20 to 110, such as from 30 to 110, from 40 to 110, from 50 to 110, or from 60 to 110.

4 . The surfactant of any of claims 1-3 , 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 1 ; and
wherein ε is from 0.5 to 6, such as from 1 to 6, from 1.5 to 5, from 2 to 4.5, or from 2 to 4.

5 . The surfactant of any of claims 1-4 , 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 any of claims 1-4 , 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 any of claims 1-6 , 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 any of claims 7-8 , wherein x is from 5 to 50, such as from 10 to 50, from 20 to 45, from 25 to 45, or from 25 to 40.

10 . The surfactant of any of claims 7-9 , wherein y is from 5 to 45, such as from 10 to 40, from 15 to 40, from 15 to 30, or from 15 to 25.

11 . The surfactant of any of claims 7-10 , wherein the ratio of x:(y+z) is from 0.5:1 to 2:1.

12 . The surfactant of any of claims 7-10 , wherein y is 0 and z is 0.

13 . The surfactant of any of claims 1-12 , wherein each of the pendant polycarboxylate moieties comprises a pendant bicarboxylate moiety.

14 . The surfactant of any of claims 1-13 , wherein each of the pendant polycarboxylate moieties is defined by the formula below

or a salt thereof.

15 . The surfactant of any of claims 1-14 , 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 . 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.

17 . The mixture of claim 16 , wherein the first surfactant is present in an amount of from 5% by weight to 80% by weight, based on the total weight of the surfactant mixture; and
the second surfactant is present in an amount of from 5% by weight to 80% by weight, based on the total weight of the surfactant mixture.

18 . The mixture of any of claims 16-17 , wherein AO represents, individually for each occurrence, an alkyleneoxy group selected from an ethoxy group or a propoxy group.

19 . The surfactant of any of claims 16-18 , wherein w is, individually for each occurrence, an integer from 20 to 110, such as from 30 to 110, from 40 to 110, from 50 to 110, or from 60 to 110.

20 . The surfactant of any of claims 16-19 , wherein the sum of e and f is from 8 to 22.

21 . An aqueous composition comprising water and a surfactant defined by any of claims 1-15 .

22 . The composition of claim 21 , wherein the composition comprises a surfactant mixture defined by any of claims 16-20 .

23 . The composition of any of claims 21-22 , wherein the composition further comprises one or more co-surfactants, 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 surfa

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