Gemini surfactants containing an unsaturated linker for clay swelling inhibition

Patent metadata

Field	Value
Publication number	US-11566167-B2
Application number	US-201916718616-A
Country	US
Kind code	B2
Filing date	Dec 18, 2019
Priority date	Dec 18, 2019
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

Amidoamine-based gemini surfactants having dual chains connected via an alkenylene or alkynylene linker. Each chain contains a quaternary ammonium head group and an ethoxylated alkyl tail. A water-based drilling fluid containing the gemini surfactant is also provided. As examined by linear swelling and free swelling tests, the gemini surfactant is effective in reducing clay swelling.

First claim

The invention claimed is:

1. A surfactant of formula (I)

or a solvate thereof, a tautomer thereof, a stereoisomer thereof, or a mixture thereof;
wherein:
each of R 1 and R 2 are independently selected from the group consisting of a hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, and an optionally substituted arylalkyl;
each of R 3 and R 4 are independently selected from the group consisting of an optionally substituted alkyl, an optionally substituted cycloalkyl, and an optionally substituted arylalkyl;
L is a C 2-12 alkenylene or a C 2-12 alkynylene linker;
each of n is independently an integer in a range of 1-15;
each of x is independently an integer in a range of 5-21;
each of y is independently an integer in a range of 2-5; and
X is an anion selected from the group consisting of a halide ion, a hexafluorophosphate ion, a trifluoromethanesulfonate ion, and a tetrafluoroborate ion.

2. The surfactant of claim 1 , wherein each of R 1 and R 2 are independently a hydrogen, or a methyl.

3. The surfactant of claim 1 , wherein each of R 1 and R 2 are a hydrogen.

4. The surfactant of claim 1 , wherein each of R 3 and R 4 are independently selected from the group consisting of a methyl, an ethyl, and an isopropyl.

5. The surfactant of claim 1 , wherein each of R 3 and R 4 are a methyl.

6. The surfactant of claim 1 , wherein L is a linear C 2-8 alkenylene.

7. The surfactant of claim 6 , wherein L is selected from the group consisting of —CH 2 —CH═CH—CH 2 —, —(CH 2 ) 2 —CH═CH—(CH 2 ) 2 —, and —(CH 2 ) 3 —CH═CH—(CH 2 ) 3 —.

8. The surfactant is claim 7 , wherein L is —CH 2 —CH═CH—CH 2 —.

9. The surfactant of claim 1 , wherein L is a linear C 2-8 alkynylene.

10. The surfactant of claim 9 , wherein L is selected from the group consisting of —CH 2 —C≡C—CH 2 —, —(CH 2 ) 2 —C≡C—(CH 2 ) 2 —, and —(CH 2 ) 3 —C≡C—(CH 2 ) 3 —.

11. The surfactant of claim 10 , wherein L is —CH 2 —C≡C—CH 2 —.

12. The surfactant of claim 1 , wherein each of n is an integer in a range of 2-11.

13. The surfactant of claim 1 , wherein each of x is an integer in a range of 11-13.

14. The surfactant of claim 1 , wherein each of y is 3.

15. The surfactant of claim 1 , wherein X is bromide or chloride.

16. The surfactant of claim 1 , which is selected from the group consisting of:
a surfactant represented by formula (II)

 and a stereoisomer thereof;
a surfactant represented by formula (III)

 and a stereoisomer thereof; and mixtures thereof,
wherein:
each of n 1 and n 2 are independently an integer in a range of 2-11; and
each of x 1 and x 2 are independently an integer in a range of 11-13.

17. A drilling fluid, comprising:
an aqueous base fluid; and
the surfactant of claim 1 .

18. The drilling fluid of claim 17 , wherein the surfactant is represented by formula (II)

or a stereoisomer thereof, or a mixture thereof,
wherein:
each of n 1 is independently an integer in a range of 2-11; and
each of x 1 is independently an integer in a range of 11-13.

19. The drilling fluid of claim 17 , wherein the surfactant is present in an amount of 0.001-5 wt. % relative to a total weight of the drilling fluid.

20. The drilling fluid of claim 17 , which is substantially free of a potassium salt.

Assignees

• Univ King Fahd Pet & Minerals

Inventors

• Kamal Muhammad Shahzad
• Hussain S M Shakil
• Murtaza Mobeen
• MAHMOUD Mohamed

Classifications

• C09K2208/06

  Structured surfactants, i.e. well drilling or treating fluids with a lamellar or spherulitic phase · CPC title

• C09K8/604 Primary

  Polymeric surfactants · CPC title

• C09K2208/12

  Swell inhibition, i.e. using additives to drilling or well treatment fluids for inhibiting clay or shale swelling or disintegrating · CPC title

• C09K8/18

  characterised by the organic compounds · CPC title

• C09K8/035 Primary

  Organic additives · CPC title