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1. (WO2010086652) DI-SUBSTITUTED PYRIDINIUM POLYMERS AND SYNTHESIS THEREOF
Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters Machine translation

CLAIMS

1. A method of producing a di-substituted pyridinium polymer, the method comprising the steps of: obtaining a 2, 3, or 4-substituted pyridine monomer of the formula NC5R4-R' -X, wherein R is selected from hydrogen, hydroxyl, and substituted or unsubstituted alkyl, alkoxy, aryl, alkaryl, aralkyl, and alkenyl groups, R' is a linking group, and X is a leaving group; and polymerising the 2, 3, or 4-substituted pyridine monomer by microwave-assisted polymerisation.

2. A method of claim 1, wherein the pyridine monomer is a 3-substituted pyridine monomer.

3. A method of claim 1 or 2, wherein R' is selected from an alkylene group, an alkenyl-containing group, an alkynyl-containing group, and a cyclopropanyl-containing group.

4. A method of claim 3, wherein R' is selected from a group -(CH2)m—, wherein m is an integer from 2 to 15, a group having from 2 to 15 carbon atoms containing one or more alkenyl groups, a group having from 2 to 15 carbon atoms containing one or more alkynyl groups, and cis- or trans-- (CH2) p-cyclopropanyl- (CH2) q- wherein p and q are the same or different and are integers from 1 to 6.

5. A method of claim 4, wherein R' is selected from methylene, ethylene, propylene, butylene, pentylene, hexylv, heptylene, octylene, nonylene, decylene, undecylene and dodecylene .

6. A method of any preceding claim, wherein X is a halide, triflate, mesylate or tosylate group.

7. A method of claim 6, wherein X is bromide, chloride or iodide .

8. A method of any preceding claim, wherein the pyridine monomer is selected from 3- (3-chloropropyl) pyridine, 3- (7-bromoheptyl) pyridine, 3- (7-chloroheptyl) pyridine, 3- (8-bromooctyl) pyridine, 3- (12-bromododecyl) pyridine and 3- (12-chlorododecyl ) pyridine.

9. A method of any preceding claim, wherein the pyridine monomer is dissolved in methanol prior to polymerisation.

10. A method of any preceding claim, wherein the microwave-assisted polymerisation step is carried out at a temperature between 1000C and 2000C.

11. A method of claim 10, wherein the microwave-assisted polymerisation step is carried out at a temperature of 1300C.

12. A method of any preceding claim, wherein the microwave-assisted polymerisation step is carried out from between 20 minutes and 80 hours.

13. A method of any preceding claim, wherein the microwave-assisted polymerisation step is carried out at a pressure of between 7 and 9 bar.

14. A method of claim 13, wherein the microwave-assisted polymerisation step is carried out at a pressure of 8 bar.

15. A method of any preceding claim, wherein the microwave-assisted polymerisation step is performed on a Biotage Initiator Microwave Synthesizer.

16. A method of claim 15, wherein the microwave-assisted polymerisation step is carried out at a power of 30 to 40 Watts.

17. A method of any preceding claim wherein the di-substituted pyridinium polymer produced is cyclic or linear.

18. A di-substituted pyridinium polymer obtained from a method of any preceding claim.

19. A di-substituted pyridinium polymer composition comprising polymer chains of the formula

NC5R4-R'- [X-N+C5R4-R' Jn-NC5R4-R' X or - [X"N+C5R4-R' ] n- wherein R is selected from hydrogen, hydroxyl, and substituted or unsubstituted alkyl, alkoxy, aryl, alkaryl, aralkyl, and alkenyl groups,

R' is a linking group,

X is a counter ion, n is the degree of polymerisation and is between 40 and 70, wherein at least 50% of the di-substituted pyridinium polymer chains in the composition have the same degree of polymerisation.

20. A di-substituted pyridinium polymer composition of claim 19 wherein at least 55% of the di-substituted pyridinium polymer chains in the composition have the same degree of polymerisation.

21. A di-substituted pyridinium polymer composition of claim 19 or 20 wherein n is 50 to 70.

22. A di-substituted pyridinium polymer composition of any one of claims 19 to 21, wherein the di-substituted-pyridinium polymer comprises pyridinium rings substituted by R' at the - A l -3 po s it ion .

23. A di-substituted pyridinium polymer composition of any one of claims 19 to 22, wherein R' is selected from an alkylene group, and alkenyl-containing group, an alkynyl-containing group, and a cyclopropanyl-containing group.

24. A di-substituted pyridinium polymer composition of claim

23, wherein R' is selected from a group -(CH2)m—, wherein m is an integer from 2 to 15, a group having from 2 to 15 carbon atoms containing one or more alkenyl groups, a group having from 2 to 15 carbon atoms containing one or more alkynyl groups, and cis- or trans- - (CH2) p-cyclopropanyl- (CH2) q- wherein p and q are the same or different and are integers from 1 to 6.

25. A di-substituted pyridinium polymer composition of claim

24, wherein R' is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene and dodecylene.

26. A di-substituted pyridinium polymer composition of any one of claims 19 to 25, wherein X is a halide, triflate, mesylate or tosylate group.

27. A di-substituted pyridinium polymer composition of claim 26, wherein X is bromide, chloride or iodide.

28. A di-substituted pyridinium polymer composition of any of claims 19 to 27 which is linear or cyclic.

29. Poly- ( 3- ( 12-bromododecyl) pyridine having 50 to 60 monomer units and a molecular weight of 12 to 15 kDa .

30. Poly- ( 3- ( 8-bromooctyl ) pyridine having 60 to 70 monomer units and a molecular weight of 11 to 13 kDa .

31. A di-substitued pyridinium polymer composition of any one of claims 19 to 30 for use as an antibacterial agent, an acetylcholine esterase inhibitor, a haemolytic agent, or a transfection reagent.

32. A method substantially as hereinbefore described with reference to the drawings.

33. A polymer composition substantially as hereinbefore described with reference to the drawings.