IP Library Granted Patent US 12,398,313
Granted Patent B2
US 12,398,313 · App. 18/091,232 · Granted Aug 26, 2025

Ionic liquid chain transfer agent as well treatment additive

Inventors: Evan Samples (Houston, TX); Ronald Bosch (Houston, TX); Denise Nicole Benoit (Houston, TX); Antonio Recio (Houston, TX)
Assignee: Halliburton Energy Services, Inc.
C09K8/608C08F120/60E21B43/16C09K2208/12
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,398,313
App. No.
18/091,232
Granted
Aug 26, 2025
Kind
B2
Abstract

Well treatment fluids comprise well treatment additives comprising an ionic liquid. Method of treating a subterranean formation may comprise contacting the subterranean formation with the well treatment additive, wherein the well treatment additive comprises an ionic liquid comprising a cation and an anion having the following formula: [R 1 R 2 R 3 R 4 N] + [X] − , wherein R 1 , R 2 , R 3 , R 4 are individually selected from the group consisting of an alkyl group, a hydroxyalkyl group, and a combination thereof provided that at least one of R 1 , R 2 , R 3 , R 4 is the hydroxyalkyl group, and wherein the anion X − comprises at least one anion selected from the group consisting of F − , Cl − , Br − , I − , H 2 PO 4 − , HPO 4 2− , PO 4 3− , HSO 4 − , C 7 H 7 OSO 3 − , C 7 H 7 SO 3 − , SO 4 2− , CH 3 SO 3 − , C 2 H 5 SO 3 − , CH 3 OSO 3 − , C 2 H 5 OSO 3 − , and combinations thereof.

Claims (17)

1. A method of treating a subterranean formation, comprising:

contacting the subterranean formation with a well treatment additive,

wherein the well treatment additive comprises:

an ionic liquid consisting of a cation and an anion having the following formula: [R 1 R 2 R 3 R 4 N] + [X] − ,

wherein R 1 , R 2 , R 3 , and R 4 are individually selected from the group consisting of an alkyl group, a hydroxyalkyl group, and a combination thereof provided that at least one of R 1 , R 2 , R 3 , or R 4 is the hydroxyalkyl group, and

wherein the anion X − consists of C 2 H 5 OSO 3 − , and

an ionic liquid polymer that is a reaction product of methacrylamide and the ionic liquid,

wherein the ionic liquid acts as a chain transfer agent and controls a molecular weight of the ionic liquid polymer, wherein the ionic liquid polymer has a molecular weight in a range of 25,000 to 50,000,

wherein the ionic liquid that is remaining after formation of the reaction product and not in the ionic liquid polymer is present in an amount of about 1 wt % to about 10 wt % of the well treatment additive;

wherein the ionic liquid polymer is present in an amount from about 0.1 wt % to about 55 wt %; and

wherein the well treatment additive is present in a treatment fluid of the subterranean formation in an amount of about 0.1 wt % to about 0.6 wt % of the treatment fluid.

2. The method of claim 1 , wherein the ionic liquid is a hydroxyalkyl ammonium sulfate.

3. The method of claim 1 , wherein the ionic liquid is ethyl (2-hydroxyethyl) dimethylammonium ethyl sulfate.

4. The method of claim 1 , wherein the ionic liquid polymer is a reaction product of methacrylamide and ethyl (2-hydroxyethyl) dimethylammonium ethyl sulfate.

5. The method of claim 1 , wherein the well treatment additive stabilizes clay in the subterranean formation.

6. The method of claim 1 , further comprising introducing a treatment fluid comprising the well treatment additive into a wellbore to contact the subterranean formation.

7. The method of claim 1 , wherein the well treatment additive comprises a solvent in an amount of about 1 wt % to about 99 wt % by weight of the well treatment additive.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2023
From: SAMPLES, EVAN; BOSCH, RONALD; BENOIT, DENISE NICOLE; RECIO, ANTONIO
To: HALLIBURTON ENERGY SERVICES, INC.
Reel/Frame 062426/0313 →
Continuity (1)
Related Publication 20240228861A1 · Jul 11, 2024
References Cited (44)
US 6608005B2 · Palmer · 2003 [cited by examiner]
US 9702219B2 · Stanciu · 2017 [cited by examiner]
US 10072203B2 · Chen et al. · 2018 [cited by applicant]
US 10087384B2 · Reid et al. · 2018 [cited by applicant]
US 10351760B2 · Schultheiss · 2019 [cited by examiner]
US 10844263B2 · Aston · 2020 [cited by examiner]
US 10988657B2 · Shumway et al. · 2021 [cited by applicant]
US 11124692B2 · Weers · 2021 [cited by examiner]
US 11254881B2 · Weers · 2022 [cited by examiner]
US 11485915B2 · Weers et al. · 2022 [cited by applicant]
US 20070254822A1 · Szarvas et al. · 2007 [cited by applicant]
US 20090029880A1 · Berry · 2009 [cited by examiner]
US 20140378638A1 · Wang · 2014 [cited by applicant]
US 20150047849A1 · Wicker, Jr. · 2015 [cited by examiner]
US 20170145282A1 · Shumway et al. · 2017 [cited by applicant]
US 20190051326A1 · Kondo et al. · 2019 [cited by applicant]
US 20210155846A1 · Xu et al. · 2021 [cited by applicant]
CA 2951371 · 2016 [cited by applicant]
CA 3105166 · 2020 [cited by applicant]
CN 104402742 · 2015 [cited by applicant]
CN 104497994 · 2015 [cited by applicant]
CN 104498960 · 2015 [cited by applicant]
CN 103320797 · 2015 [cited by applicant]
CN 109987723 · 2019 [cited by applicant]
CN 209797599 · 2019 [cited by applicant]
CN 111826244 · 2020 [cited by applicant]
CN 111875504 · 2020 [cited by applicant]
CN 111892499 · 2020 [cited by applicant]
CN 111908626 · 2020 [cited by applicant]
CN 112093918 · 2020 [cited by applicant]
CN 112777758 · 2021 [cited by applicant]
EP 3820961 · 2021 [cited by applicant]
GB 2433951 · 2007 [cited by applicant]
GB 2444614A · 2008 [cited by applicant]
JP 5717112 · 2015 [cited by applicant]
WO 2014098871A2 · 2014 [cited by applicant]
WO 2016010520 · 2016 [cited by applicant]
Tadeusz Biedroń; Przemyslaw Kubisa (2007). Chain transfer to ionic liquid in an anionic polymerization of methyl methacrylate. , 45(17), 4168-4172. [cited by applicant]
Macromolecules, One-Pot Synthesis of Ion-Containing CO2-Based Polycarbonates Using Protic Ionic Liquids as Chain Transfer Agents, Huang, et al., American Chemical Society, 2018. [cited by applicant]
Journal of Polymer Science: Part A: Polymer Chemistry, 2007, 45, 4168 & 4172. [cited by applicant]
Rosen, Mark A. et al. “Carbon-11 Choline: Synthesis, Purification, and Brain Uptake Inhibition by 2-Dimethylaminoethanol.” The Journal of Nuclear Medicine, vol. 26, No. 12, Dec. 1985, pp. 1424-1428, p. 1424. PDF file. 5… [cited by applicant]
Earl, Gary W. et al. “Quaternary Methyl Carbonates: Novel Agents For Fabric Conditioning.” Journal of Surfactants and Detergents, vol. 8, No. 4, Oct. 2005, pp. 325-329, p. 325; scheme 1. PDF file. 5 pages. [cited by applicant]
International Search Report and Written Opinion for International Patent Application No. PCT/US2023/027223 dated Oct. 17, 2023. PDF file. 13 pages. [cited by applicant]
Quaternary Ammonium Salts, Chemicke Listy, Mar. 2017, pp. 197-205 (Year: 2017). [cited by applicant]