Gas separation membrane, gas separation module, gas separation device, and gas separation method

1. A gas separation membrane comprising:

a gas separation layer which is formed to include a polyimide compound,

wherein the polyimide compound includes a repeating unit represented by the following Formula (I),

in Formula (I), R represents a group having a structure represented by any of the following Formulae (I-1) to (I-28), X 1 to X 3 represent a single bond or a divalent linking group, L represents —CH═CH— or —CH 2 —, R 1 and R 2 represent a hydrogen atom or a substituent group, and the symbol “*” represents a binding site with respect to a carbonyl group in Formula (I),

R 3 represents a group selected from a group consisting of an alkyl group, a halogen atom, a carboxy group, a hydroxyl group, an alkylamino group, an arylamino group, an acylamino group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfo group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group,

A 1 to A 3 represent a hydrogen atom or a group selected from a group consisting of an alkyl group, a halogen atom, a carboxy group, a hydroxyl group, an alkylamino group, an arylamino group, an acylamino group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group, but all of A 1 to A 3 do not represent a hydrogen atom at the same time, and

at least one of R 3 , A 1 , A 2 , and A 3 represents a group selected from a group consisting of a carboxy group, a hydroxyl group, an alkylamino group, an acylamino group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group

2. The gas separation membrane according to claim 1 , wherein the polyimide compound is a copolymer comprising the repeating unit represented by Formula (I) and a repeating unit represented by the following Formula (II-a) or (II-b),

in Formulae (II-a) and (II-b), R has the same definition as that for R in Formula (I), R 4 to R 6 represent a substituent group, l1, m1, and n1 represent an integer of 0 to 4, and X 4 represents a single bond or a divalent linking group.

3. The gas separation membrane according to claim 1 , wherein the gas separation membrane is a composite gas separation membrane which includes the gas separation layer on the upper side of a support layer having gas permeability.

4. The gas separation membrane according to claim 3 , wherein the support layer is formed of a porous layer on a gas separation layer side and a non-woven fabric layer on a side opposite to the gas separation layer.

5. The gas separation membrane according to claim 1 ,

wherein, in a case where gas subjected to a separation treatment is mixed gas of carbon dioxide and methane, the permeation rate of carbon dioxide at 40° C. and 5 MPa is greater than 20 GPU, and

the ratio between permeation rates of carbon dioxide and methane (R CO2 /R CH4 ) is 15 or greater.

6. The gas separation membrane according to claim 4 , wherein the molecular weight cut-off of the porous layer is 100000 or less.

7. The gas separation membrane according to claim 1 , which is used to allow selective permeation of carbon dioxide from gas containing carbon dioxide and methane.

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

9. A gas separation device comprising the gas separation module according to claim 8 .

10. A gas separation method comprising:

allowing carbon dioxide to selectively permeate from gas containing carbon dioxide and methane using the gas separation membrane according to claim 1 .

11. A gas separation membrane comprising:

a gas separation layer which is formed to include a polyimide compound,

wherein the polyimide compound is a copolymer comprising a repeating unit represented by the following Formula (I) and a repeating unit represented by the following Formula (II-a) or (II-b),

in Formula (I), R represents a group having a structure represented by any of the following Formulae (I-1) to (I-28), X 1 to X 3 represent a single bond or a divalent linking group, L represents —CH═CH— or —CH 2 —, R 1 and R 2 represent a hydrogen atom or a substituent group, and the symbol “*” represents a binding site with respect to a carbonyl group in Formula (I),

R 3 represents a group selected from a group consisting of an alkyl group, a halogen atom, a carboxy group, a hydroxyl group, an alkylamino group, an arylamino group, an acylamino group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfo group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group,

A 1 to A 3 represent a hydrogen atom or a group selected from a group consisting of an alkyl group, a halogen atom, a carboxy group, a hydroxyl group, an alkylamino group, an arylamino group, an acylamino group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group, but all of A 1 to A 3 do not represent a hydrogen atom at the same time, and

at least one of R 3 , A 1 , A 2 , and A 3 represents a group selected from a group consisting of a carboxy group, a hydroxyl group, an alkylamino group, an acylamino group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, an imidazole group, a triazole group, a tetrazole group, a cyano group, a sulfonamide group, an alkylsulfonyl group, and a mercapto group

in Formulae (II-a) and (II-b), R has the same definition as that for R in Formula (I), R 4 to R 6 represent a substituent group, l1, m1, and n1 represent an integer of 0 to 4, and X 4 represents a single bond or a divalent linking group.

12. The gas separation membrane according to claim 11 , wherein the gas separation membrane is a composite gas separation membrane which includes the gas separation layer on the upper side of a support layer having gas permeability.

13. The gas separation membrane according to claim 12 , wherein the support layer is formed of a porous layer on a gas separation layer side and a non-woven fabric layer on a side opposite to the gas separation layer.

14. The gas separation membrane according to claim 11 ,

wherein, in a case where gas subjected to a separation treatment is mixed gas of carbon dioxide and methane, the permeation rate of carbon dioxide at 40° C. and 5 MPa is greater than 20 GPU, and

the ratio between permeation rates of carbon dioxide and methane (R CO2 /R CH4 ) is 15 or greater.

15. The gas separation membrane according to claim 13 , wherein the molecular weight cut-off of the porous layer is 100000 or less.

16. The gas separation membrane according to claim 11 , which is used to allow selective permeation of carbon dioxide from gas containing carbon dioxide and methane.

17. A gas separation module comprising the gas separation membrane according to claim 11 .

18. A gas separation device comprising the gas separation module according to claim 17 .

19. A gas separation method comprising:

allowing carbon dioxide to selectively permeate from gas containing carbon dioxide and methane using the gas separation membrane according to claim 11 .