Block copolymer, ion-exchange membrane and method of preparing block copolymer

Patent metadata

Field	Value
Publication number	US-11220583-B2
Application number	US-202016897818-A
Country	US
Kind code	B2
Filing date	Jun 10, 2020
Priority date	Nov 16, 2016
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

Abstract

A block copolymer, an ion-exchange membrane including the block copolymer and a method of preparing the block copolymer are provided. The block copolymer may include a hydrophobic repeating unit and a hydrophilic repeating unit.

First claim

What is claimed is:

1. An ion conductive block copolymer comprising:
a hydrophobic repeating unit represented by Formula 1 below; and
a hydrophilic repeating unit represented by Formula 3 below:

wherein in Formulae 1 and 3,
Ar 1 is an aromatic group including a single benzene ring or at least two benzene rings, the at least two benzene rings are directly connected to each other or are bonded to each other through a linking group selected from —O—, —S—, —S(O 2 )—, —(C(O))—, —(CF 2 ) n —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, an imide bond, an ether imide bond, phosphine, imidazole, or —(CH 2 ) n — in which n is an integer of 1 to 10, each of the benzene rings is unsubstituted or substituted with —COR 1 or —CN, and R 1 is an aromatic group including at least one benzene ring;
Ar′ 2 is an aromatic group including a single benzene ring or at least two benzene rings substituted with —COR 4 , R 4 or both, and R 4 is selected from the group consisting of high-density functional groups FG represented by:

wherein M is alkali metal, X is a negative ion of OH − , and n is a rational number of 1 to 20, and R 5 through R 7 are the same as or different from each other and are C 1 to C 6 alkyl, cyclohexane or benzyl;
Ar 3 and Ar′ 3 are each independently an aromatic group including a single benzene ring or at least two benzene rings, the at least two benzene rings are directly connected to each other or are bonded to each other through a linking group selected from —O—, —S—, —S(O 2 )—, —(C(O))—, —C(CH 3 ) 2 —, —(CH 2 ) n —, —C(CF 3 ) 2 —, or —(CF 2 ) n — in which n is an integer of 1 to 10, and each of the benzene rings is unsubstituted or substituted with a halogen ion, or —(CH 2 ) n CH 3 in which n is an integer of 0 to 6;
Ar 4 and Ar′ 4 are the same as or different from each other and are

wherein n is an integer of 1 or 2, and two of R a through R d are connected to a main chain of the block copolymer and the rest are the same as or different from each other and are hydrogen, benzene or alkyl;
A is —O—, —S—, or —S(O 2 )—;
z is an integer of 0 or 1; and
x and y are each independently an integer of 1 to 100,
n and m are each independently an integer of 1 to 1000.

2. The ion conductive block copolymer of claim 1 , wherein Ar 1 is selected from the group consisting of:

3. The ion conductive block copolymer of claim 1 , wherein Ar 1 is selected from the group consisting of:

wherein a and b are each independently an integer of 1 to 100.

4. The ion conductive block copolymer of claim 1 , wherein R 1 is selected from the group consisting of:

5. The ion conductive block copolymer of claim 1 , wherein Ar′ 2 is selected from the group consisting of:

6. The ion conductive block copolymer of claim 1 , wherein Ar′ 2 is selected from the group consisting of:

wherein a and b are each independently an integer of 1 to 100.

7. The ion conductive block copolymer of claim 1 , wherein Ar 3 and Ar′ 3 are each independently an aromatic group represented by Formulae 3a through 3d below:

wherein R 3 is fluorine (F), chlorine (Cl) hydroxy, acetylene, or —(CH 2 ) n CH 3 in which n is an integer of 0 to 10, W is —O—, —S—, —S(O 2 )—, —(C(O))—, —C(CH 3 ) 2 —, —(CH 2 ) n —, —C(CF 3 ) 2 —, or —(CF 2 ) n —in which n is an integer of 1 to 10, c is an integer of 0 to 4, and d is an integer of 0 to 100.

8. The ion conductive block copolymer of claim 1 , wherein Ar 3 and Ar′ 3 are selected from the group consisting of:

wherein n is an integer of 1 or 2.

9. A polymer electrolyte comprising the ion conductive block copolymer of claim 1 .

10. An ion-exchange membrane comprising the polymer electrolyte of claim 9 .

Assignees

• Korea Inst Energy Res

Inventors

• Bae Byungchan
• Yim Sung-Dae
• Kim Chang-Soo
• Lee Won-Yong
• Park Gu-Gon
• Yang Tae-Hyun
• Park Seok-Hee
• Kim Minjin
• Sohn Young-Jun
• Kim Seung-Gon
• Shin Dong Won
• Nugraha Adam Febriy-Anto

Classifications

• C08J5/2225

  containing fluorine · CPC title

• C08G61/02 Primary

  Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes · CPC title

• Y02E60/50

  Fuel cells · CPC title

• C08J5/2262 Primary

  containing fluorine · CPC title

• C08G65/4025

  (I) or (II) containing fluorine other than as leaving group (X) · CPC title