IP Library Granted Patent US 8,664,282
Granted Patent B2
US 8,664,282 · App. 12/809,364 · Granted Mar 4, 2014

Process to prepare crosslinkable trifluorostyrene polymers and membranes

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Quick Facts
Patent No.
US 8,664,282
App. No.
12/809,364
Granted
Mar 4, 2014
Kind
B2
Abstract

Described herein is a process to prepare crosslinkable polymers based on trifluorostyrene, and their use as polymer electrolyte membranes.

Claims (13)

1. A process to prepare a crosslinked membrane, comprising the steps:

a. providing a copolymer comprising repeat units of Formulae (V) and (VI)

wherein Rf and Rf′ are independently a linear or branched perfluoroalkylene group, optionally containing oxygen or chlorine; X is Br or Cl; and Q is F, Br, or Cl;

b. forming a membrane from the copolymer;

c. hydrolyzing the —SO 2 Q moiety to form a —SO 3 H moiety or salt thereof; and

d. exposing the copolymer to radiation to form a crosslinked polymer, either before or after formation into a membrane;

wherein the monomer of Formula VI can enable copolymerization, crosslinking and oxidation to a stable polymer electrolyte membrane that is conductive at low relative humidity, having through-plane conductivity, at 25% relative humidity and 80° C., of at least 13 mS/cm, and transverse direction swelling of not more than 78%.

2. The process of claim 1 wherein Rf and Rf′ are independently selected from the group consisting of (CF 2 ) r wherein r=1 to 20, (CF 2 CF 2 ) r OCF 2 CF 2 wherein r=1 to 6, and (CF 2 CF(CF 3 )O) r CF 2 CF 2 wherein r=1 to 8.

3. The process of claim 1 wherein the copolymer additionally comprises repeat units of Formula (VII)

4. The process of claim 1 wherein Formula (V) is Formula (Va) and Formula (VI) is Formula (VIa)

wherein Q is F and X is Br.

5. The process of claim 1 , further comprising converting the —S moieties of both Formulae (V) and (VI) into —SO 2 — moieties to form an oxidized copolymer by contacting said —S— moieties with an oxidizing agent, either before or after formation into a membrane.

6. The process of claim 4 , wherein the membrane has through-plane conductivity, at 25% relative humidity and 80° C., of at least 24 mS/cm, and transverse direction swelling of not more than 57%.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2014
From: ROELOFS, MARK GERRIT; TEASLEY, MARK F
To: E. I. DUPONT DE NEMOURS AND COMPANY
Reel/Frame 032469/0959 →