Partially fluorinated compounds and polymers

Claim 2

A compound of the formula wherein Y is independently selected from the group consisting of -CN, -CH 2 NH 2 , -COOH, -CH 2 0H, -CH 2 N=C=O, -CONH 2 , -CHO, -COCI, and -COOR, wherein R is C n H 2n+1 and n is an integer from 1 to 10, inclusive; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 3

A compound according to Claim 1 wherein Y is -CN.

Claim 4

A compound according to Claims 1 or 2 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 5

A compound according to Claims 1 or 2 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 6

A compound of the formula wherein Y is independently selected from the group consisting of -CN, -CH 2 NH 2 , -CH 2 OH, -CH 2 N=C=O, -CONH 2 , -CHO, -COCI, and -COOR, wherein R is C n H 2n+1 and n is an integer from 1 to 10, inclusive; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 7

A compound of the formula wherein Y is independently selected from the group consisting of -CN, -CH 2 NH 2 , -CH 2 OH, -CH 2 N=C=O, -CONH 2 , -CHO, -COCI, and -COOR, wherein R is C n H 2n+1 and n is an integer from 1 to 10, inclusive; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 8

A compound according to Claim 5 wherein Y is -CN.

Claim 9

A compound according to Claims 5 or 6 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 10

A compound according to Claims 5 or 6 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 11

A polymer (A) comprising 100 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NHCH 2 -, OCH 2 -, -C(=0), and -CH 2 NH-(C = O); X is independently selected from the group consisting of NH-, O-, and -C(=O), provided that when X is NHCH 2 - or OCH 2 -, X must be -C(=0), and also provided that when X is -C(=O) or -CH 2 NH(C=O), X must be NH- or 0-; Z is any divalent organic radical; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 12

A polymer (A) comprising 100 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NHCH 2 -, OCH 2 -, -C(=0), and -CH 2 NH-(C = O); X is independently selected from the group consisting of NH-, O-, and -C(=O), provided that when X is NHCH 2 - or OCH 2 -, X must be -C(=0), and also provided that when X is -C(=O) or -CH 2 NH(C=O), X must be NH- or 0-; Z is any divalent organic radical; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 13

A polymer (A) according to Claim 9 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 14

A polymer (A) according to Claim 9 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 15

A polymer (A) according to Claims 9, 10, or 11 wherein Z is selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from 1 to about 20 carbon atoms and containing from zero to about 10 ether linkages.

Claim 16

A polymer (A) according to Claim 12 wherein Z is selected from the group consisting of -C 6 H 4 -, -C 10 H 6 -, and -(CH 2 ) n - and n is an integer from 2 to 20.

Claim 17

A polymer (A) according to Claims 9, 10, or 11 wherein Z is -CH 2 CH 2 -R f '-CH 2 CH 2 -; X is -C(=0); and R f ' is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 18

A polymer (A) according to Claim 14 wherein R f ' is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 19

A polymer (A) according to Claim 14 wherein Rf is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 20

A polymer (A) according to Claims 9, 10, or 11 wherein Z is -CH 2 CH 2 CH 2 -R f '-CH 2 CH 2 CH 2 -; X is independently selected from the group consisting of -NH and -0; and Rf is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 21

A polymer (A) according to Claim 17 wherein R f ', is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 22

A polymer (A) according to Claim 17 wherein R f ' is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 23

A polymer (A) according to Claims 9, 10, or 11 wherein Z is any mesogenic divalent organic radical.

Claim 24

A polymer (A) according to Claim 20 wherein Z is of the formula -V-W-V- wherein V is a divalent radical independently selected from the group consisting of 1,4-phenylene, 4,4 - biphenylene, naphthylidene, 1,4-[2.2.2]-bicyclooctylidene, and 1,4-cyclohexylidene; and W is a divalent radical selected from the group consisting of -CH = N-, -N(O) = N-, -N = N-, -C(=O)-O-, -C = C-, -CH = CH-, -CH = C(CH 3 )-, -C( = O)-NH-, -CH = CH-CH = N-, -CH = CH-C( = 0)-0-, and -CH = N-N = CH-.

Claim 25

A copolymer (A) comprising from 1 to 99 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NHCH 2 -, OCH 2 -, -C(=O), and -CH 2 NH-(C = 0); X is independently selected from the group consisting of NH-, 0-, and -C(=O), provided that when X is NHCH 2 - or OCH 2 -, X must be -C(=O), and also provided that when X is -C(=0) or -CH 2 NH(C=O), X' must be NH- or 0-; Z is any divalent organic radical; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages; and from 99 to 1 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NH-, O-, and -C(=0); X is independently selected from the group consisting of NH-, 0-, and -C(=0), provided that when X is -C(=0), X must be NH- or O-, and also provided that when X is NH- or 0-, X must be -C(=0); and Z is any divalent organic radical independently selected.

Claim 26

A copolymer (A) comprising from 1 to 99 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NHCH 2 -, OCH 2 -, -C(=O), and -CH 2 NH-(C = 0); X is independently selected from the group consisting of NH-, 0-, and -C(=O), provided that when X is NHCH 2 - or OCH 2 -, X must be -C(=O), and also provided that when X is -C(=0) or -CH 2 NH(C=O), X' must be NH- or 0-; Z is any divalent organic radical; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages; and from 99 to 1 mole percent of at least one independently selected repeating unit of the formula wherein X is independently selected from the group consisting of NH-, O-, and -C(=0); X is independently selected from the group consisting of NH-, 0-, and -C(=0), provided that when X is -C(=0), X must be NH- or O-, and also provided that when X is NH- or 0-, X must be -C(=0); and Z is any divalent organic radical independently selected.

Claim 27

A copolymer (A) according to Claim 22 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 28

A copolymer (A) according to Claim 22 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 29

A copolymer (A) according to Claims 22, 23, or 24 wherein Z in repeating unit (3) and Z' in repeating unit (4) are independently selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from 1 to about 20 carbon atoms and containing from zero to about 10 ether linkages.

Claim 30

A copolymer (A) according to Claim 25 wherein at least one of Z or Z is selected from the group consisting of -C 6 H 4 -, -C 10 H 6 -, and -(CH 2 ) n - and n is an integer from 2 to 20.

Claim 31

A copolymer (A) according to Claims 22, 23, or 24 wherein at least one of Z or Z is -CH 2 CH 2 -R' f CH 2 CH 2 -; X is -C(=0); and R f ' is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 32

A copolymer (A) according to Claim 27 wherein Rf is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 33

A copolymer (A) according to Claim 27 wherein Rf is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 34

A copolymer (A) according to Claims 22, 23, or 24 wherein at least one of Z or Z is -CH 2 CH 2 CH 2 - R f '-CH 2 CH 2 CH 2 -; X is independently selected from the group consisting of -NH and -O; and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 35

A copolymer (A) according to Claim 30 wherein Rf is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 36

A copolymer (A) according to Claim 30 wherein R f ' is -(CF 2 CF 2 ) n and n is an integer from 1 to 6.

Claim 37

A copolymer (A) according to Claims 22, 23, or 24 wherein at least one of Z or Z is any mesogenic divalent organic radical independently selected.

Claim 38

A copolymer (A) according to Claim 33 wherein Z is of the formula -V-W-V- wherein v is a divalent radical independently selected from the group consisting of 1,4-phenylene, 4,4,- biphenylene, naphthylidene, 1,4-[2.2.2]-bicyclooctylidene, and 1,4-cyclohexylidene, and W is a divalent radical selected from the group consisting of -CH = N-, -N(O) = N-, -N = N-, -C( = 0)-0-, -C≡C-, -CH = CH-, -CH = C(CH 3 )-, -C( = O)-NH-, -CH = CH-CH = N-, -CH = CH-C( = O)-O-, and -CH = N-N = CH-.

Claim 39

A polymer (B) comprising 100 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 40

A polymer (B) comprising 100 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages.

Claim 41

A polymer (B) according to Claim 35 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 42

A polymer (B) according to Claim 35 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 43

A polymer (B) according to Claims 35, 36, or 37 wherein U is selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from about 6 to about 20 carbon atoms and containing from 0 to about 5 linkages selected from the group consisting of ether and sulfonyl.

Claim 44

A polymer (B) according to Claims 35, 36, or 37 wherein U is selected from the group consisting of 1,2,4,5-benzenetetrayl, 2,2-bis(3,4-phenylene)-propane, and 2,2-bis(3,4-phenylene)-1,1,1,3,3,3-hexafluoropropane.

Claim 45

A copolymer (B) comprising from 1 to 99 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages; and from 99 to 1 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and Z is any divalent organic radical.

Claim 46

A copolymer (B) comprising from 1 to 99 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and R f is a perfluorinated divalent organic radical selected from the group consisting of linear, branched, carbocyclic, and mixtures thereof having from 1 to about 40 carbon atoms and containing from zero to about 20 ether linkages; and from 99 to 1 mole percent of at least one independently selected repeating unit of the formula wherein U is any tetravalent organic radical and Z is any divalent organic radical.

Claim 47

A copolymer (B) according to Claim 40 wherein R f is the branched and carbocyclic 4,5-(2,2-trifluoromethyl)-1,3-dioxolanediyl.

Claim 48

A copolymer (B) according to Claim 40 wherein R f is -(CF 2 CF 2 ) n - and n is an integer from 1 to 6.

Claim 49

A copolymer (B) according to Claims 40, 41, or 42 wherein U in repeating unit (5) and U in repeating unit (6) are independently selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from about 6 to about 20 carbon atoms and containing from 0 to about 5 linkages selected from the group consisting of ether and sulfonyl.

Claim 50

A copolymer (B) according to Claim 43 wherein Z is selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from 1 to about 20 carbon atoms and containing from zero to about 10 ether linkages.

Claim 51

A copolymer (B) according to Claim 44 wherein Z is selected from the group consisting of 4,4 - diphenylene ether, m-phenylene, and p-phenylene.

Claim 52

A copolymer (B) according to Claims 40, 41, or 42 wherein U in repeating unit (5) and U in repeating unit (6) are independently selected from the group consisting of 1,2,4,5-benzenetetrayl, 2,2-bis-(3,4-phenylene)propane, and 2,2-bis(3,4-phenylene)-1,1,1,3,3,3-hexafluoropropane.

Claim 53

A copolymer (B) according to Claim 46 wherein Z is selected from the group consisting of linear, branched, carbocyclic, aromatic, and mixtures thereof having from 1 to about 20 carbon atoms and containing from zero to about 10 ether linkages.

Claim 54

A copolymer (B) according to Claim 47 wherein Z is selected from the group consisting of 4,4 - diphenylene ether, m-phenylene, and p-phenylene.