Polymers derived from 2,2′-bisimidazoles
Disclosed are compositions derived from 2,2′bisimidazoles building blocks and methods of making the same. The disclosed compositions are capable of withstanding temperatures up to 600° C. and substantially flame resistant.
1. A composition comprising a polymer obtained by polymerizing a mixture comprising a compound having the formula:
wherein:
R 1 is C 1 -C 10 alkyl or C 1 -C 10 perfluoroalkyl;
Y is N or N + —R 6 , wherein R 6 is C 1 -C 10 alkyl, wherein R 6 is optionally substituted with C 6 -C 14 aryl or C 1 -C 13 heteroaryl;
R 2 , R 2′ , R 3 , and R 3′ are, each independent of the other, selected from hydrogen; or
wherein R 2 and R 3 together form a 6 membered ring containing 6 carbon atoms; and/or
wherein R 2′ and R 3′ together form a 6 membered ring containing 6 carbon atoms;
R 4 and R 5 are each H or a group having the formula:
wherein when R 4 and R 5 are each H, the mixture further comprises a compound of formula X—R′—X, wherein X is a leaving group selected from chlorine, bromine, iodine, mesylate, triflate, and tosylate, and R′ is C 1 -C 10 alkyl or C 1 -C 10 alkoxy;
when R 4 and R 5 are each a group having the formula:
the mixture further comprises a compound having the formula:
when R 4 and R 5 are each a group having the formula:
the mixture further comprises a compound having the formula:
2. The composition according to claim 1 , wherein the mixture comprises a compound having the formula:
and a compound having the formula:
3. The composition according to claim 1 , wherein the mixture comprises a compound having the formula:
and a compound having the formula:
4. The composition according to claim 1 , wherein the mixture comprises a compound having the formula:
and the mixture further comprises a compound having the formula:
5. The composition according to claim 1 , wherein R 1 is selected from CH 2 CH 2 CH 2 CH 2 or CF 2 CF 2 CF 2 CF 2 .
6. The composition according to claim 1 , wherein Y is N.
7. The composition according to claim 1 , wherein Y is N + —R 6 and R 6 is C 1 -C 10 alkyl substituted by an imidazole or imidazolium cation.
8. The composition according to claim 7 , wherein R 6 has the formula:
9. A composition comprising a polymer obtained by polymerizing a mixture comprising a compound having the formula:
10. The composition according to claim 9 , wherein R 1 is selected from CH 2 CH 2 CH 2 CH 2 or CF 2 CF 2 CF 2 CF 2 .
11. The composition according to claim 9 , wherein Y is N.
12. The composition according to claim 9 , wherein Y is N + —R 6 and R 6 is C 1 -C 10 alkyl substituted by an imidazole or imidazolium cation.
13. The composition according to claim 12 , wherein R 6 has the formula: