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

Patent metadata

Field	Value
Publication number	US-10040035-B2
Application number	US-201615074790-A
Country	US
Kind code	B2
Filing date	Mar 18, 2016
Priority date	Sep 20, 2013
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

In this case, at least one of R3, A1, A2, and A3 represents a specific polar group.

First claim

What is claimed is:

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 separati

Assignees

• Fujifilm Corp

Inventors

• Usami Ryota
• Hironaka Koji
• Sano Satoshi
• Narita Takeshi

Classifications

• B01D2257/504

  Carbon dioxide · CPC title

• B01D53/228

  characterised by specific membranes · CPC title

• B01D2256/245

  Methane · CPC title

• C08G73/1071

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title

• C08G73/10

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title