IP Library Granted Patent US 12,489,130
Granted Patent B2
US 12,489,130 · App. 17/909,833 · Granted Dec 2, 2025

Fluoropolymer comprising pendent groups with ionic bis(sulfonyl)imide moiety and perfluoroether terminal group

Inventors: Matthew J. Lindell (Woodbury, MN); Michael A. Yandrasits (Hastings, MN); Andrew T. Haug (Woodbury, MN)
Assignee: 3M Innovative Properties Company
H01M8/1039C08F8/34C08F8/44C08F214/262C08G65/007C08G65/3348H01M8/1027H01M8/103H01M8/1032C08G2650/48H01M2008/1095
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Quick Facts
Patent No.
US 12,489,130
App. No.
17/909,833
Granted
Dec 2, 2025
Kind
B2
Abstract

A fluoropolymer is described comprising pendent groups having the formula: —(CF 2 ) a —(OC b F 2b ) c —(OC e F 2e )—SO 2 —[NX 2 —SO 2 (CF 2 ) f —SO 2 ] d —NX 1 —SO 2 —Rf wherein Rf is a perfluoroether and X 1 and X 2 are independently cationic counterions. Also described are various articles including catalyst ink, polymer electrolyte membranes, and membrane electrode assemblies comprising the fluoropolymer described herein; as well as a method of making a fluoropolymer.

Claims (28)

1 . A fluoropolymer comprising pendent groups according to the formula:

(OCF e F 2e )—SO 2 —[NX 2 —SO 2 (CF 2 ) f —SO 2 ] d —NX 1 —SO 2 —Rf

wherein

Rf is a perfluoroether;

e and f independently range from 2 to 6;

d 1, or greater than 1; and

X 1 and X 2 are independently cationic counterions.

2 . The fluoropolymer of claim 1 wherein Rf is a perfluoroether having 3 to 12 perfluorinated carbon atoms.

3 . The fluoropolymer of claim 1 wherein X 1 and X 2 are hydrogen ion.

4 . The fluoropolymer of claim 1 wherein the fluroropolymer further comprises up to 10 mol % of pendent groups comprising at least one bis(sulfonyl)imide moiety and a terminal group selected from sulfonic acid and sulfonamide.

5 . The fluoropolymer of claim 1 wherein the fluoropolymer comprises 5 to 50 mol % of the pendent groups.

6 . The fluoropolymer of claim 1 wherein the fluoropolymer comprises a backbone comprising 50 to 95 mol % polymerized units of —[CF 2 —CF 2 ]—.

7 . The fluoropolymer of claim 1 wherein the fluoropolymer has an electrochemical oxygen permeability coefficient at 80° C. of at least

i) 1.1E-13 at 25% relative humidity;

ii) 1.5E-13 at 50% relative humidity;

iii) 2.2E-13 at 100% relative humidity; or

a combination thereof.

8 . The fluoropolymer of claim 1 wherein the fluoropolymer has an oxygen permeability coefficient at 23° C. and zero relative humidity of at least 8.5E-15.

9 . The fluoropolymer of claim 1 wherein the fluoropolymer has an ionic conductivity at 80° C. of at least

i) 0.001, 0.005, or 0.010 S/cm at 25% relative humidity;

ii) 0.010, 0.020, 0.030, 0.040, or 0.050 S/cm at 50% relative humidity;

iii) 0.050, 0.10, 0.15, 0.20, or 0.25 S/cm at 90% relative humidity; or

a combination thereof.

10 . The fluoropolymer of claim 1 wherein the fluoropolymer is dispersed in an organic solvent.

11 . The fluoropolymer of claim 1 wherein the fluoropolymer is dispersed in an aqueous solvent or water and water-miscible organic solvent mixture.

12 . A catalyst ink comprising the fluoropolymer of claim 1 .

13 . A polymer electrolyte membrane prepared from the fluoropolymer of claim 1 .

14 . A membrane electrode assembly comprising the fluoropolymer of claim 1 as a catalyst ink or as a polymer electrolyte membrane.

Assignments (2)
CONFIRMATORY LICENSE Recorded May 15, 2024
From: 3M COMPANY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 067415/0608 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2022
From: LINDELL, MATTHEW J.; YANDRASITS, MICHAEL A.; HAUG, ANDREW T.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 061012/0409 →
Continuity (2)
Provisional Application 63001716 · Mar 30, 2020
Related Publication 20240204227A1 · Jun 20, 2024
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