Granted Patent B2

US 8,030,405 · App. 12/434,761 · Granted Oct 4, 2011

Assignee: GM Global Technology Operations LLC

Abstract

Claims (76)

1. A polymer blend comprising:

a first polymer comprising a cyclobutyl moiety wherein the cyclobutyl moiety is:

and a non-ionic fluorine containing polymer.

2. The polymer blend of claim 1 wherein the first polymer comprises polymer segments 1 and 2:

[E 1 (SO 2 X) d ]—P 1 -Q 1 -P 2   1

E 2 -P 3 -Q 2 -P 4   2

wherein:

E 1 (SO 2 X) d is a sulfonated aromatic containing moiety;

E 1 is an aromatic containing moiety;

E 2 is an unsulfonated aromatic-containing and/or aliphatic-containing moiety;

X is an —OH, a halogen, an ester, or

d is the number of (SO 2 X) d attached to E 1 ;

P 1 , P 2 , P 3 , P 4 are each independently: absent, —O—, —S—, —SO—, —CO—, —SO 2 —, —NR 1 H—, NR 2 —, or —R 3 —;

R 2 is C 1-25 alkyl, C 1-25 aryl or C 1-25 arylene;

R 3 is C 1-25 alkylene, C 1-25 perfluoroalkylene, perfluoroalkyl ether, alkylether, or C 1-25 arylene;

R 4 is trifluoromethyl, C 1-25 alkyl, C 1-25 perfluoroalkylene, C 1-25 aryl, or another E 1 group; and

Q 1 , Q 2 are each independently a fluorinated cyclobutyl moiety.

3. The polymer blend of claim 1 wherein the first polymer comprises segments 3 and 4:

wherein:

E 1 , E 2 are each independently an aromatic-containing and/or aliphatic-containing moiety;

X is an —OH, a halogen, an ester, or

d is the number of (SO 2 X) d attached to E 1 ;

P 1 , P 2 , P 3 , P 4 are each independently: absent, —O—, —S—, —SO—, —CO—, —SO 2 —, —NH—, NR 2 —, or —R 3 —, and

R 2 is C 1-25 alkyl, C 1-25 aryl or C 1-25 arylene;

R 3 is C 1-25 alkylene, C 1-25 perfluoroalkylene, perfluoroalkyl ether, alkylether, or C 1-25 arylene;

R 4 is trifluoromethyl, C 1-25 alkyl, C 1-25 perfluoroalkylene, C 1-25 aryl, or another E 1 group;

R 8 (SO 2 X) d is a sulfonated aliphatic or aromatic containing moiety; and

Q 1 , Q 2 are each independently a fluorinated cyclobutyl moiety.

4. The polymer blend of claim 1 wherein the first polymer comprises segments 5 and 6:

E 1 (SO 2 X) d —P 1 -Q 1 -P 2   5

E 2 -P 3 -Q 2 -P 4   6

connected by a linking group L 1 to form polymer units 7 and 8:

wherein:

E 1 (SO 2 X) d is a sulfonated aromatic-containing moiety;

E 2 is an unsulfonated aromatic-containing and/or aliphatic-containing moiety;

L 1 is a linking group;

X is an —OH, a halogen, an ester, or

d is a number of (SO 2 X) functional groups attached to E 1 wherein d is an integer from 0 to 4;

P 1 , P 2 , P 3 , P 4 are each independently absent, —O—, —S—, —SO—, —SO 2 —, —CO—, —NH—, NR 2 —, —R 3 —, and

R 2 is C 1-25 alkyl, C 1-25 aryl or C 1-25 arylene;

R 3 is C 1-25 alkylene, C 1-25 perfluoroalkylene, or C 1-25 arylene;

R 4 is trifluoromethyl, C 1-25 alkyl, C 1-25 perfluoroalkylene, C 1-25 aryl, or another E 1 group;

Q 1 , Q 2 are each independently a fluorinated cyclobutyl moiety;

i is a number representing repetition of polymer segment 5; and,

j is a number representing repetition of a polymer segment 6.

5. The polymer blend of claim 1 wherein the first polymer comprises polymer segments 9 and 10:

E 1 (SO 2 X) d —P 1 -Q 1 -P 2   9

E 2 (SO 2 X) f —P 3   10

wherein:

E 1 , E 2 are each independently an aromatic or aliphatic-containing moiety wherein at least one of E 1 and E 2 include an aromatic group substituted with —SO 2 X;

X is an —OH, a halogen, an ester, or

d is the number of (SO 2 X) functional groups attached to E 1 wherein d is an integer from 0 to 4;

f is the number of (SO 2 X) functional groups attached to E 2 wherein f is an integer from 0 to 4;

P 1 , P 2 , P 3 are each independently absent, —O—, —S—, —SO—, —SO 2 —, —CO—, —NH—, NR 2 —, —R 3 —, and

R 2 is C 1-25 alkyl, C 1-25 aryl or C 1-25 arylene;

R 3 is C 1-25 alkylene, C 1-25 perfluoroalkylene, perfluoroalkyl ether, alkyl ether, or C 1-25 arylene;

R 4 is trifluoromethyl, C 1-25 alkyl, C 1-25 perfluoroalkylene, C 1-25 aryl, or another E 1 group; and

Q 1 is a fluorinated cyclobutyl moiety,

with the proviso that when d is greater than zero, f is zero and when f is greater than zero d is zero.

6. The polymer blend of claim 1 where the first polymer includes one or more of the following protogenic functional groups: —SO 3 H, COOH, PO 3 R 12 H, and combinations thereof, R 12 is H, aryl, phenyl, methyl, ethyl, propyl, butyl, and pentyl.

7. The polymer blend of claim 1 wherein the non-ionic fluorine containing polymer is selected from the group consisting of poly(tetrafluoroethlyene-co-ethylene), polyvinylidene difluoride, poly(vinylidene fluoride-co-hexafluoropropylene), poly(tetrafluoroethylene-co-propylene), terpolymer of vinylidene fluoride, hexafluoropropylene and tetrafluoroethylene, and terpolymer of ethylene, tetrafluoroethylene and perfluoromethylvinylether.

8. The polymer blend of claim 1 wherein the non-ionic fluorine containing polymer comprises a copolymer of vinylidene fluoride and hexafluoropropylene.

9. A polymer blend comprising:

an ionic polymer blend comprising an ionic polymer having a cyclobutyl moiety and an ionic moiety that does not contain a cyclobutyl moiety wherein the cyclobutyl moiety is:

and

a non-ionic fluorine containing polymer.

10. The polymer blend of claim 9 wherein the ionic moiety that does not contain a cyclobutyl moiety is selected from the group consisting of polymers, oligomers or additives containing an aryl sulfonic acid moiety, an alkyl sulfonic acid moiety, a perfluorosulfonic acid moiety, a partially fluorinated sulfonic acid moiety or a phosphonic acid containing moiety, and mixtures thereof.

11. The polymer blend of claim 2 wherein d is equal to the number of aromatic rings in E 1 .

12. The polymer blend of claim 2 wherein d is an integer from 0 to 4.

13. The polymer blend of claim 12 wherein E 1 comprises a component selected from the group consisting of:

14. The polymer blend of claim 3 wherein d is equal to the number of aromatic rings in E 1 .

15. The polymer blend of claim 3 wherein d is an integer from 0 to 4.

16. The polymer blend of claim 15 wherein E 1 comprises a component selected from the group consisting of:

17. The polymer blend of claim 4 wherein d is equal to the number of aromatic rings in E 1 .

18. The polymer blend of claim 4 wherein E 1 and E 2 each independently comprise a component selected from the group consisting of:

19. The polymer blend of claim 5 wherein E 1 and E 2 each independently comprise a component selected from the group consisting of:

Assignments (8)

Continuity (2)