IP Library › Granted Patent US 12,338,382
Granted Patent B2
US 12,338,382 · App. 16/500,250 · Granted Jun 24, 2025

Surfactants having non-conventional hydrophobes

Inventors: Upali Weerasooriya (Austin, TX); Peter Radford (Lenexa, KS); Kevin Sikkema (Overland Park, KS); John Boorem (Kansas City, KS); Aaron Boorem (Leavenworth, KS); Kurt Cheshire (Shawnee, KS); Kishore K. Mohanty (Austin, TX); Krishna Panthi (Cedar Park, TX); Himanshu Sharma (Austin, TX); Pinaki Ghosh (Austin, TX)
Assignee: Harcros Chemicals, Inc.
C09K23/00C07C59/125C07C217/28C07C305/10C09K8/584C09K23/16C11D1/06C11D1/29C11D1/722E21B43/16C11D2111/20
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Quick Facts
Patent No.
US 12,338,382
App. No.
16/500,250
Granted
Jun 24, 2025
Kind
B2
Abstract

The present invention is directed to surfactants with small hydrophobes, which are of non-conventional hydrophobe size. The surfactants of the present invention utilize a small hydrophobic moiety with a polyalkoxylate chain comprising PO, BO and/or EO groups, with optional ionic groups, such as anionic, cationic and zwitterionic, to achieve the desired hydrophilic-lipophilic balance (HLB). The present invention is further directed to formulations comprising the surfactants of the invention, and methods of using the surfactants of the invention, including in enhanced oil recovery applications.

Claims (43)

1. A compound having the formula:

R 1 —O—(PO x -EO y ) —Z

wherein R 1 is a branched C 3 to C 7 alkyl;

wherein x is 15-100;

wherein y is 10-250;

wherein (x+y)≥25; and

wherein Z is carboxylate.

2. The compound of claim 1 , wherein R 1 is selected from the group consisting of isopropyl, isobutyl, t-butyl, sec-butyl, and their isomers.

3. The compound of claim 2 , wherein R 1 is isobutyl, t-butyl, or sec-butyl.

4. The compound of claim 1 , wherein R 1 is methylpentyl.

5. The compound of claim 1 , wherein y is an integer from 65 to 105.

6. The compound of claim 5 , wherein x is greater than or equal to y.

7. An aqueous composition comprising the compound of claim 1 and a co-surfactant.

8. An emulsion comprising the aqueous composition of claim 7 and a hydrocarbon material.

9. A method of using the compound of claim 1 in an enhanced oil recovery method comprising:

contacting a hydrocarbon with the compound of claim 1 , wherein said hydrocarbon is in contact with a solid material in a petroleum reservoir; and

allowing said hydrocarbon material to separate from the solid material.

10. A method of using the compound of claim 1 in household, institutional or industrial cleaning comprising:

contacting a household, institutional or industrial surface with the compound of claim 1 .

11. A compound having the formula:

R 1 —O—(PO x -EO y ) —Z

wherein R 1 is C 1 , C 2 , or a branched C 3 or C 4 alkyl;

wherein x is 15-100;

wherein y is 10-250;

wherein (x+y)≥25; and

wherein Z is carboxylate.

12. A compound having the formula:

R 1 —O—(PO x -EO y ) —Z

wherein R 1 is a branched C 5 to C 8 ;

wherein x is 15-100;

wherein y is 10-250;

wherein (x+y)≥25; and

wherein Z is carboxylate.

13. An aqueous composition comprising the compound of claim 11 and a co-surfactant.

14. A method of using the compound of claim 11 in an enhanced oil recovery method comprising:

contacting a hydrocarbon with the compound of claim 11 , wherein said hydrocarbon is in contact with a solid material in a petroleum reservoir; and

allowing said hydrocarbon material to separate from the solid material.

15. An aqueous composition comprising the compound of claim 12 and a co-surfactant.

16. A method of using the compound of claim 12 in an enhanced oil recovery method comprising:

contacting a hydrocarbon with the compound of claim 12 , wherein said hydrocarbon is in contact with a solid material in a petroleum reservoir; and

allowing said hydrocarbon material to separate from the solid material.

17. An emulsion comprising the aqueous composition of claim 13 and a hydrocarbon material.

18. An emulsion comprising the aqueous composition of claim 15 and a hydrocarbon material.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2019
From: WEERASOORIYA, UPALI; RADFORD, PETER; SIKKEMA, KEVIN; BOOREM, JOHN; BOOREM, AARON; CHESHIRE, KURT
To: HARCROS CHEMICALS, INC.
Reel/Frame 050604/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2019
From: GHOSH, PINAKI; MOHANTY, KISHORE K.; PANTHI, KRISHNA; SHARMA, HIMANSHU
To: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 050604/0169 →
Continuity (2)
Provisional Application 62481393 · Apr 4, 2017
Related Publication 20210039060A1 · Feb 11, 2021
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