Back to results
US 2013/0171528 A1Published application
Organo-Copper Reagents for Attaching Perfluorosulfonic Acid Groups to Polyolefins
AssigneeGM Global Technology Operations LLC
InventorsTIMOTHY J. FULLER, LIJUN ZOU, MICHAEL R. SCHOENEWEISS
Life of this patent
Estimating the term…
Abstract
An ion conducting membrane for fuel cells involves coupling a compound having a sulfonic acid group with a polymeric backbone. Each of the compounds having a sulfonic acid group and the polymeric backbone are first functionalized with a halogen.
Claims19
A method of forming an ion conducting polymeric membrane for fuel cells, the method comprising:
- a) reacting a polymer having formula 1 with a compound having formula 2
- in the presence of an organocuprate compound to form a polymer having formula (3):
- wherein:
- X1, X2 are each independently a halogen;
- R1, R2, and R3 are each independently hydrogen or C1-C6 alkyl;
- R4, R5 are each independently phenyl, C1-C12 alkyl, C1-C12 alkyl ether, C1-C12 fluoroalkyl, C1-C12 fluoroalkyl ether, C7-C30 arylalkyl, C7-C30 phenylalkyl, C7-C12 aryl, —(CH2)r— or —(CF2)p—O—(CF2)q—;
- Z is hydrogen or a metal;
- n is a number from 10 to 500;
- and
- p, q, r are each independently an integer from 2 to 10;
- and
- b) forming a membrane from the polymer having formula (3).
9 more elements
A method of forming an ion conducting polymeric membrane for fuel cells, the method comprising:
- a) reacting a compound having formula 4 with a compound having formula 5
- R7—O—R6—X3 (4)
- X2—R5—SO3Z (5)
- in the presence of an organocuprate compound to form a compound having formula 6:
- R7—O—R6—R5—SO2Z (6)
- b) converting the compound having formula 6 to a compound having formula 7:
- reacting the compound having formula 7 with a compound having formula 8 to form a polymer having formula 9:
- wherein:
- X1, X2, X3 are each independently a halogen;
- R1, R2, and R3 are each independently hydrogen or C1-C6 alkyl;
- R4, R5 are each independently phenyl, C1-C12 alkyl, C1-C12 alkyl ether, C1-C12 fluoroalkyl, C1-C12 fluoroalkyl ether, C7-C30 arylalkyl, C7-C30 phenylalkyl, C7-C12 aryl, —(CH2)r—, or —(CF2)p—P—(CF2)q—;
- R6 is phenyl, C1-C12 alkyl, C1-C12 alkyl ether, C1-C12 fluoroalkyl, C1-C12 fluoroalkyl ether, C7-C30 arylalkyl, C7-C30 phenylalkyl, C7-C12 aryl, —(CH2)r—, or —(CF2)p—O—(CF2)q—;
- Z is hydrogen or a metal;
- n is a number from 10 to 500;
- and
- p, q, r are each independently an integer from 2 to 10;
- and
- c) forming a membrane from the polymer having formula 9.
15 more elements
Dependencies are inferred from the claim text.