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US 8,044,146 B1Granted
Combination of main-chain and side-chain sulfonation of PFCB-6F high-temperature fuel cell membranes
AssigneeGM Global Technology Operations LLC
InventorsLijun Zou, Sean M. MacKinnon, Timothy J. Fuller
Life of this patent
Estimating the term…
Abstract
A polymer useful as an ion conducting membrane for fuel cell applications includes both main chain and side chain protogenic groups. Methods for preparing the polymer include addition of the side chains both before and after addition of the protogenic groups.
Claims24
A polymer having formula 1:
- wherein:
- Z1, Z2, and Z3 are each independently —SO2X, —PO3H2, or —COX;
- d is the number of Z2 attached to E1;
- f is the number of Z3 attached to E2;
- E1 and E2 are each independently an aromatic-containing moiety;
- A is absent or O or a chain extender having a carbon backbone;
- X is an —OH, a halogen, an ester, or
- P1, P2, P3, P4 are each independently absent, —O—, —S—, —SO—, —SO2—, —CO—, —NH—, NR2—, or —R3—;
- R2 is C1-25 alkyl, C1-25 aryl, or C1-25 arylene;
- R3 is C1-25 alkylene, C1-25 perfluoroalkylene, or C1-25 arylene;
- R4 is trifluoromethyl, C1-25 alkyl, C1-25 perfluoroalkylene, C1-25 aryl, or another E1 group;
- i and j are each independently an integer from 1 to 10,000;
- and
- Q1 and Q2 are each independently a fluorinated cyclobutyl moiety.
11 more elements
A method of making a polymer having formula 1:
- wherein:
- Z1, Z2, and Z3 are each independently —SO2X, —PO3H2, or —COX;
- d is the number of Z2 attached to E1;
- f is the number of Z3 attached to E2;
- E1 and E2 are each independently an aromatic-containing moiety;
- A is absent or O or a chain extender having a carbon backbone;
- X is an —OH, a halogen, an ester, or
- P1, P2, P3, P4 are each independently absent, —O—, —S—, —SO—, —SO2—, —CO—, —NH—, NR2—, or —R3—;
- R2 is C1-25 alkyl, C1-25 aryl, or C1-25 arylene;
- R3 is C1-25 alkylene, C1-25 perfluoroalkylene, or C1-25 arylene;
- R4 is trifluoromethyl, C1-25 alkyl, C1-25 perfluoroalkylene, C1-25 aryl, or another E1 group;
- i and j are each independently an integer from 1 to 10,000;
- and
- Q1 and Q2 are each independently a fluorinated cyclobutyl moiety, the method comprising:
- a) reacting a compound having formula 2 with a compound having formula 3 for form a compound having formula 4:
- b) adding protogenic groups to moiety E1 and/or E2 to form the compound having formula 1.
13 more elements
A method of making a polymer having formula 1:
- wherein:
- Z1, Z2, and Z3 are each independently —SO2X, —PO3H2, or —COX;
- d is the number of Z2 attached to E1;
- f is the number of Z3 attached to E2;
- E1 and E2 are each independently an aromatic-containing moiety;
- A is absent or O or a chain extender having a carbon backbone;
- X is an —OH, a halogen, an ester, or
- P1, P2, P3, P4 are each independently absent, —O—, —S—, —SO—, —SO2—, —CO—, —NH—, NR2—, or —R3—;
- R2 is C1-25 alkyl, C1-25 aryl, or C1-25 arylene;
- R3 is C1-25 alkylene, C1-25 perfluoroalkylene, or C1-25 arylene;
- R4 is trifluoromethyl, C1-25 alkyl, C1-25 perfluoroalkylene, C1-25 aryl, or another E1 group;
- i and j are each independently an integer from 1 to 10,000;
- and
- Q1 and Q2 are each independently a fluorinated cyclobutyl moiety, the method comprising:
- a) adding a protogenic group to moiety E1 and/or E2 in a compound having formula 2 to form the compound having formula 5:
- b) reacting the compound having formula 5 with a compound having formula 3 to form the compound having formula 1:
13 more elements
Dependencies are inferred from the claim text.