IP Library Granted Patent US 9,350,035
Granted Patent B2
US 9,350,035 · App. 14/446,453 · Granted May 24, 2016

Cross-linked polymer electrolyte membranes

Inventor: Rameshwar Yadav (Farmington, MI)
Assignee: NISSAN NORTH AMERICA, INC.
H01M8/1023H01M8/1039H01M2300/0082
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Quick Facts
Patent No.
US 9,350,035
App. No.
14/446,453
Granted
May 24, 2016
Kind
B2
Abstract

Crosslinked polymers are produced by polymerizing a styrene-based comonomer with a bifunctional styrenated crosslinkable monomer comprising the following straight chain formula: CH 2 ═CH—C 6 H 4 —CH 2 —(OCH 2 CH 2 ) n —O—CH 2 —C 6 H 4 —CH═CH 2 . The styrenated crosslinkable monomer can be produced from a two arm polyethylene glycol having a molecular weight between 200 g/mol and 35,000 g/mol. The styrenated crosslinkable monomer can also be produced from a two arm polyethylene oxide having a molecular weight between 100 kg/mol and 800 kg/mol. The styrenated crosslinkable monomer can also be produced from a four arm polyethylene glycol. Polymer electrolyte membranes are produced from the crosslinked polymers.

Claims (23)

1. A polymer electrolyte membrane for a fuel cell comprising a crosslinked polymer produced by polymerizing a styrene-based comonomer with a styrenated crosslinkable monomer comprising the following straight chain formula:

CH 2 ═CH—C 6 H 4 —CH 2 —(OCH 2 CH 2 ) n —O—CH 2 —C 6 H 4 —CH═CH 2 ,

wherein the crosslinked polymer has the following Formula A:

wherein X=SO 3 H + or R f —SO 3 H + , with R f =—(CF 2 ) m —O—CF 2 CF 2 — and m=2-7 in which R f is obtained from I—(CF 2 ) m —O—CF 2 —CF 2 —SO 2 F, with m=2-7.

2. The polymer electrolyte membrane of claim 1 , wherein the styrenated crosslinkable monomer is produced from a two arm polyethylene glycol having a molecular weight between 200 g/mol and 35,000 g/mol.

3. The polymer electrolyte membrane of claim 1 , wherein the styrenated crosslinkable monomer is produced from a two arm polyethylene oxide having a molecular weight between 100 kg/mol and 800 kg/mol.

4. The polymer electrolyte membrane of claim 1 , wherein the styrenated crosslinkable monomer is produced from a four arm polyethylene glycol.

5. The polymer electrolyte membrane of claim 1 , wherein the crosslinked polymer is a fluorinated crosslinked polymer having the following formula:

6. The polymer electrolyte membrane of claim 1 , wherein the crosslinked polymer is further polymerized with a free radical scavenger.

7. The polymer electrolyte membrane of claim 1 , wherein the crosslinked polymer is further polymerized with a free radical scavenger selected from 4-hydroxy styrene and 4-vinylaniline, the crosslinked polymer having free radical scavengers and shown in the following formula, wherein Z=OH or NH 2 :

8. The polymer electrolyte membrane of claim 1 , wherein the styrene-based comonomer has the formula CH 2 ═CH—C 6 H 4 —SO 3 H + and the crosslinked polymer has the Formula A wherein X=SO 3 H + .

9. The polymer electrolyte membrane of claim 1 , wherein the styrene-based comonomer has the formula CH 2 ═CH—C 6 H 4 —SO 3 Na + and the crosslinked polymer has the Formula A wherein X=SO 3 H + .

10. The polymer electrolyte membrane of claim 1 , wherein the styrene-based comonomer has the formula CH 2 ═CH—C 6 H 4 —SO 2 Cl or CH 2 ═CH—C 6 H 4 —SO 2 F and the crosslinked polymer has the Formula A wherein X=SO 3 H + .

11. The polymer electrolyte membrane of claim 1 , wherein the styrene-based comonomer has the formula CH 2 ═CH—C 6 H 4 —Br, and the crosslinked polymer has the Formula A wherein X=R f —SO 3 H + , with R f =—(CF 2 ) m —O—CF 2 CF 2 — and m=2-7 in which R f is obtained from I—(CF 2 ) m —O—CF 2 —CF 2 —SO 2 F, with m=2-7.

12. The polymer electrolyte membrane of claim 1 , wherein the styrene-based comonomer has the formula CH 2 ═CH—C 6 H 4 —OH, and the crosslinked polymer has the Formula A wherein X=—O—R f —SO 3 H + , with R f =—(CF 2 ) m —O—CF 2 CF 2 — and m=2-7 in which R f is obtained from I—(CF 2 ) m —O—CF 2 —CF 2 —SO 2 F, m=2-7.

13. The polymer electrolyte membrane of claim 1 further comprising a porous support on which the crosslinked polymer is supported.

14. A polymer electrolyte membrane for a fuel cell comprising a crosslinked polymer produced by polymerizing a styrene-based comonomer with a styrenated crosslinkable monomer comprising the following straight chain formula:

CH 2 ═CH—C 6 H 4 —CH 2 —(OCH 2 CH 2 ) n —O—CH 2 —C 6 H 4 —CH═CH 2 ,

wherein the styrenated crosslinkable monomer is produced by functionalizing polyethylene glycols with vinyl benzyl chloride, the crosslinked polymer having the formula:

wherein X=SO 3 H + or R f —SO 3 H + , with R f =—(CF 2 ) m —O—CF 2 CF 2 — and m=2-7 in which R f is obtained from I—(CF 2 ) m —O—CF 2 —CF 2 —SO 2 F, m=2-7.

15. The polymer electrolyte membrane of claim 14 further comprising a porous support on which the crosslinked polymer is supported.

16. The polymer electrolyte membrane of claim 14 , wherein the polyethylene glycol has a molecular weight between 200 g/mol and 35,000 g/mol.

17. The polymer electrolyte membrane of claim 14 , wherein the polyethylene glycol is a two arm polyethylene oxide having a molecular weight between 100 kg/mol and 800 kg/mol.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2016
From: NISSAN NORTH AMERICA, INC.
To: NISSAN MOTOR CO., LTD.
Reel/Frame 039492/0353 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 30, 2014
From: YADAV, RAMESHWAR
To: NISSAN NORTH AMERICA, INC.
Reel/Frame 033419/0177 →
Continuity (1)
Related Publication 20160036082A1 · Feb 4, 2016