Gas separation membrane and method for producing the same, and method for separating gas mixture, gas separation membrane module and gas separation apparatus using the same

1. A gas separation membrane comprising,

a separation-active membrane containing:

a compound represented by the following Formula (I) having a boiling point or a decomposition temperature of 200° C. or higher; and

a cross-linked polymer having at least one repeating unit represented by Formulae (II-1) to (II-3) below:

wherein, in Formula (I),

R 1 , R 2 and R 3 represent a hydrogen atom or a substituent;

W 1 represents a bivalent linking group;

R 1 and R 2 , R 1 and R 3 or R 2 and R 3 may be combined together to form a ring;

wherein, in each of Formulae (II-1) to (II-3):

each of R 4 , R 5 , R 6 , and R 7 independently represents a hydrogen atom or a substituent ,

J 1 , J 2 and J 3 represent —CO—, —COO—, —CONR 8 —, —O—, —O—, a methylene group , a phenylene group, or a —C 6 H 4 CO—group,

R 8 represents a hydrogen atom or a substituent,

A represents a dissociable group, and is at least one selected from a carboxyl group, a sulfonate group, a phosphate group, a hydroxyl group, —CONHSO 2 —R 11 , —SO 2 NHCO—R 12 or —SO 2 NHSO 2 —R 13 , provided that R 11 , R 12 and R 13 represent a substituent,

W 2 ,W 3 and W 4 represent a single bond or a bivalent linking group,

Y 1 and Y 2 represent an alkylene glycol residue structure wherein two hydrogen atoms have been removed from alkylene glycol, and

each of a, b and c independently represents an integer of 1 or more, x represents an integer of 0 or more, and L 1 represents an n-valent linking group, and

wherein, in the compound represented by Formula (I), [total molecular weight of a first amine group+total molecular weight of a second amine group]/[molecular weight of Formula (I)] is from 0.3 to 0.84.

2. The gas separation membrane according to claim 1 ,

wherein the cross-linked polymer has at least the repeating unit represented by Formula (II-1), and

a content of the repeating unit represented by Formula (II-1) is 10 to 90 mol% with respect to the total repeating units constituting the cross-linked polymer.

3. The gas separation membrane according to claim 1 , wherein the polymer containing the repeating units represented by Formulae (II-1) to (II-3) is formed by a compound represented by following Formulae (III), (IV), (V) or (VI):

wherein, in Formula (III), R 4 , J 1 , W 2 and A of Formula (III) have the same meaning as R 4 , J 1 , W 2 and A of Formula (II-1):

wherein, in Formula (IV), R 5 , J 2 , W 3 and Y 1 have the same meaning as R 5 , J 2 , W 3 and Y 1 of Formula (II-2),

R 9 represents a hydrogen atom or a substituent,

J 4 represents —CO—, —COO—, —CONR 10 —, —O—, —O—, a methylene group, a phenylene group or a —C 6 H 4 CO—group,

R 10 represents a hydrogen atom or a substituent, and

W 5 has the same meaning as W 3 of Formula (II-2):

wherein, in Formula (V), R 6 , J 3 , W 4 , Y 2 and R 7 of Formula (V) have the same meaning as R 6 , J 3 , W 4 , Y 2 and R 7 of Formula (II-3):

wherein, in Formula (VI), R 4 , R 5 , R 6 , R 7 , J 1 , J 2 , J 3 , W 2 , W 3 , W 4 , A, a, b, c, x, Y 1 and Y 2 have the same meaning as R 4 , R 5 , R 6 , R 7 , J 1 , J 2 , J 3 , W 2 , W 3 , W 4 , A, a, b, c, x, Y i and Y 2 of Formulae (II-1) to (II-3), and

R 9 , W 5 , and J 4 of Formula (VI) have the same meaning as R 9 , W 5 , and J 4 of Formula (IV).

4. The gas separation membrane according to claim 1 ,

wherein in Formulae (II-1) to (II-3), each of R 4 , R 5 , R 6 and R 7 independently represents a hydrogen atom or an alkyl group,

each of J 1 , J 2 and J 3 independently represents —CO—group, —COO—group, or —OCO—group,

each of W 2 , W 3 and W 4 independently represents a single bond, an alkylene group or an alkyleneoxy group, and

L 1 represents an alkylene group, or an alkyleneoxy group.

5. The gas separation membrane according to claim 1 ,

wherein, in Formula (I)

W 1 represents an alkylene group or an arylene group.

6. The gas separation membrane according to claim 1 ,

wherein the compound represented by Formula (I) and the polymer containing repeating units represented by Formulae (II-1) to (II-3) are fixed by covalent bonding.

7. The gas separation membrane according to claim 1 ,

wherein the gas separation membrane further comprises a porous membrane, and

the separation-active membrane is disposed at least on the surface of the porous membrane.

8. The gas separation membrane according to claim 1 ,

wherein the gas separation membrane separates at least one acid gas from a mix gas containing the at least one acid gas and at least one non-acid gas.

9. A method for producing the gas separation membrane according to claim 1 , comprising,

forming the gas separation membrane comprising the polymer containing at least one repeating unit represented by Formulae (II-1) to (II-3) and at least one compound represented by Formula (I) by heat curing.

10. A method for producing the gas separation membrane according to claim 1 , comprising,

forming the gas separation membrane comprising the polymer containing at least one repeating unit represented by Formulae (II-1) to (II-3) and at least one compound represented by Formula (I) by irradiating an active radiation.

11. A mixed gas separating method comprising,

separating at least one acid gas from a mixed gas containing the at least one acid gas and at least one non-acid gas by using the gas separation membrane according to claim 1 ,

wherein the acid gas is at least one selected from carbon dioxide, hydrogen sulfide, carbonyl sulfide, sulfur oxide (SOx), and nitrogen oxide (NOx), and

the non-acid gas is at least one selected from hydrogen, methane, nitrogen, and carbon monoxide.

12. The mixed gas separating method according to claim 11 ,

wherein the acid gas is carbon dioxide or hydrogen sulfide.

13. The mixed gas separating method according to claim 11 ,

wherein main components of the mixed gas are carbon dioxide and methane, or carbon dioxide and hydrogen.

14. A gas separation membrane module comprising the gas separation membrane according to claim 1 .

15. A gas separation apparatus comprising at least one of the gas separation membrane module according to claim 14 .