Ion-exchange polymer and production method therefor, electrolyte membrane and production method therefor, and composition for producing ion-exchange polymer

Patent metadata

Field	Value
Publication number	US-10279342-B2
Application number	US-201615251055-A
Country	US
Kind code	B2
Filing date	Aug 30, 2016
Priority date	Mar 7, 2014
Publication date	May 7, 2019
Grant date	May 7, 2019

Abstract

In a case where the sum of a1, b1, and c1 is 1.000, a1 is 0.000 to 0.750, b1 is 0.240 to 0.990, and c1 is 0.001 to 0.100. L represents an alkylene group, L1 and L2 each represent a divalent linking group, R1 is a hydrogen atom or an alkyl group, R2 and R3 each represent an alkyl group or an allyl group, X1− and X2− each represent an inorganic or organic anion, and Y represents a halogen atom. Z1 represents —O— or —NRa—, and Ra represents a hydrogen atom or an alkyl group.

First claim

What is claimed is:

1. An ion-exchange polymer, comprising:
a structure represented by the following General Formula (1),

wherein, in General Formula (1), in a case where the sum of a1, b1, and c1 is 1.000, a1 is 0.000 to 0.750, b1 is 0.240 to 0.990, and c1 is 0.001 to 0.100, L represents an alkylene group, L 1 and L 2 each independently represent a divalent linking group, R 1 represents a hydrogen atom or an alkyl group, R 2 and R 3 each independently represent an alkyl group or an allyl group, X 1 − and X 2 − each independently represent an inorganic anion or an organic anion, Y represents a halogen atom, Z 1 represents —O— or —NRa—, and here, Ra represents a hydrogen atom or an alkyl group.

2. The ion-exchange polymer according to claim 1 ,
wherein the structure is a structure represented by the following General Formula (2),

wherein, in General Formula (2), in a case where the sum of a2, b2, c2, and d2 is 1.000, a2 is 0.000 to 0.750, b2 is 0.240 to 0.990, c2 is 0.001 to 0.100, and d2 is 0.000 to 0.100, L, L 1 , L 2 , R 1 to R 3 , X 1 − , X 2 − , Y, and Z 1 have the same meaning as L, L 1 , L 2 , R 1 to R 3 , X 1 − , X 2 − , Y, and Z 1 in General Formula (1), respectively, Z 2 represents a group represented by the following General Formula (P-d1) or (P-d2), and Z 2 may include both the group represented by General Formula (P-d1) or the group represented by General Formula (P-d2), and

wherein L, L 1 , R 1 to R 3 , X 1 − , and Z 1 in General Formulas P-d1) and (P-d2) have the same meaning as L, L 1 , R 1 to R 3 , X 1 − , Z 1 in General Formula (2), respectively, and here, * represents the portion to which L is bonded.

3. The ion-exchange polymer according to claim 1 ,
wherein c1 or c2 is 0.005 to 0.075.

4. The ion-exchange polymer according to claim 1 ,
wherein b1 or b2 is 0.700 to 0.980, and c1 or c2 is 0.015 to 0.050.

5. The ion-exchange polymer according to claim 1 , which is formed by polymerizing and curing a composition containing at least one of a compound represented by the following General Formula (M-b) and at least one of compound represented by the following General Formula (M-c),

wherein, in General Formulas (M-b) and (M-c), R 1 represents a hydrogen atom or an alkyl group, R 2 and R 3 each independently represent an alkyl group or an allyl group, L represents an alkylene group, L 1 and L 2 each independently represent a divalent linking group, X 1 − represents an inorganic anion or an organic anion, Z 1 represents —O— or —NRa—, and here, Ra represents a hydrogen atom or an alkyl group.

6. The ion-exchange polymer according to claim 5 ,
wherein the composition further contains a compound represented by the following General Formula (M-d2),

wherein, in General Formula (M-d2), R 1 represents a hydrogen atom or an alkyl group, R 2 and R 3 each independently represent an alkyl group or an allyl group, L represents an alkylene group, Z 1 represents —O— or —NRa—, and here, Ra represents a hydrogen atom or an alkyl group.

7. The ion-exchange polymer according to claim 5 ,
wherein the composition further contains a compound represented by the following General Formula (L-c),
Y a -L 2 -Y  General Formula (L-c)

wherein, in General Formula (L-c), L 2 represents a divalent linking group, Y and Y a each independently represent a halogen atom.

8. The ion-exchange polymer according to claim 5 ,
wherein 25.0 mol % to 99.0 mol % of the compound represented by General Formula (M-b) is included with respect to the entire monomer components in the polymer obtained by polymerizing and curing.

9. The ion-exchange polymer according to claim 5 ,
wherein 50.0 mol % to 98.0 mol % of the compound represented by General Formula (M-b) is included with respect to the entire monomer components in the polymer obtained by polymerizing and curing.

10. The ion-exchange polymer according to claim 5 , which is formed by polymerizing and curing by irradiating the composition with active radiation.

11. An electrolyte membrane, comprising:
at least one ion-exchange polymer according to claim 1 .

12. The electrolyte membrane according to claim 11 , comprising:
a support.

13. The electrolyte membrane according to claim 12 ,
wherein the support is selected from woven fabric and non-woven fabric.

14. The electrolyte membrane according to claim 12 , which is formed by impregnating the support with the composition, and then polymerizing and curing the composition.

15. A composition for production of an ion-exchange polymer according to claim 1 , comprising:
a compound represented by the following General Formula (M-b);
a compound represented by the following General Formula (M-c);
a water-soluble solvent; and
a polymerization inhibitor,

wherein, in General Formulas (M-b) and (M-c), R 1 represents a hydrogen atom or an alkyl group, R 2 and R 3 each independently represent an alkyl group or an allyl group, L represents an alkylene group, L 1 and L 2 each independently represent a divalent linking group, X 1 − represents an inorganic anion or an organic anion, Z 1 represents —O— or —NRa—, and here, Ra represents a hydrogen atom or an alkyl group.

16. The composition for production of an ion-exchange polymer according to claim 15 , further comprising:
a compound represented by the following General Formula (M-d2),

wherein, in General Formula (M-d2), R 1 represents a hydrogen atom or an alkyl group, R 2 and R 3 each independently represent an alkyl group or an allyl group, L represents an alkylene group, Z 1 represents —O— or —NRa—, and here, Ra represents a hydrogen atom or an alkyl group.

17. The composition for production of an ion-exchange polymer according to claim 15 , further comprising:
a compound represented by the following General Formula (L-c),
Y a -L 2 -Y  General Formula (L-c)

wherein, in General Formula (L-c), L 2 represents a divalent linking group, Y and Y a each independently represents a halogen atom.

18. The composition for production of an ion-exchange polymer according to claim 15 ,
wherein the water-soluble solvent is water.

19. The composition for production of an ion-exchange polymer according to claim 15 ,
wherein the compound represented by General Formula (M-b) is contained in the composition in 60 parts by mass to 98 parts by mass with respect to 100 parts by mass of the composition.

20. A production method for an ion-exchange polymer, comprising:
irradiating the composition for production of an ion-exchange polymer according to claim 15 with active radiation to be polymerized and cured.

21. A production method for an electrolyte membrane, comprising:
impregnating the support with the composition for production o

Assignees

• Fujifilm Corp

Inventors

• Inomata Sotaro
• Kodama Keisuke
• Sano Satoshi
• Kaminaga Kuniyuki

Classifications

• B01D2325/42

  Ion-exchange membranes · CPC title

• B01J41/14 Primary

  obtained by reactions only involving unsaturated carbon-to-carbon bonds · CPC title

• Y02P70/56

  Cross-Sectional Technologies · mapped topic

• B01D71/40

  Polymers of unsaturated acids or derivatives thereof, e.g. salts, amides, imides, nitriles, anhydrides, esters · CPC title

• H01M2008/1095

  Fuel cells with polymeric electrolytes · CPC title