Anion exchange resin, electrolyte membrane, binder for forming electrode catalyst layer, fuel cell electrode catalyst layer and fuel cell

Patent metadata

Field	Value
Publication number	US-10734663-B2
Application number	US-201816043682-A
Country	US
Kind code	B2
Filing date	Jul 24, 2018
Priority date	Jul 24, 2017
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

An anion exchange resin capable of producing an electrolyte membrane, a binder for forming an electrode catalyst layer and a fuel cell electrode catalyst layer, which have improved chemical properties and mechanical properties; an electrolyte membrane and a binder for forming an electrode catalyst layer produced from the anion exchange resin; and a fuel cell having the electrolyte membrane or the electrode catalyst layer.

First claim

What is claimed is:

1. An anion exchange resin, comprising:
a divalent hydrophobic group being composed of one aromatic ring, or being composed of two aromatic rings which are connected to each other via a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, a divalent sulfur-containing group, or carbon-carbon bond; and
a divalent hydrophilic group being composed of one polycyclic compound, or being composed of a plurality of polycyclic compounds which are connected to each other via a linking group and/or carbon-carbon bond, wherein the linking group is a divalent hydrocarbon group, a divalent silicon-containing group, a divalent nitrogen-containing group, a divalent phosphorus-containing group, a divalent oxygen-containing group, or a divalent sulfur-containing group, and at least one of the linking group or the polycyclic compound is connected to an anion exchange group via a divalent saturated hydrocarbon group having a carbon number of 2 or more;
wherein the anion exchange resin comprises a hydrophobic unit being composed of the hydrophobic group alone, or being composed of a plurality of hydrophobic groups repeated via ether bond, thioether bond, or carbon-carbon bond;
wherein the anion exchange resin comprises a hydrophilic unit being composed of the hydrophilic group alone, or being composed of a plurality of hydrophilic groups repeated via ether bond, thioether bond, or carbon-carbon bond; and
wherein the hydrophobic unit and the hydrophilic unit are connected via ether bond, thioether bond, or carbon-carbon bond.

2. The anion exchange resin according to claim 1 , wherein the hydrophobic group comprises a bisphenol residue which is substituted with a halogen atom, a pseudohalide, an alkyl group, or an aryl group, as shown in the following formula (2);

(In the formula, R represents a hydrocarbon group, a silicon-containing group, a nitrogen-containing group, a phosphorus-containing group, an oxygen-containing group, or a sulfur-containing group, which are substituted with a halogen atom or a pseudohalide, or direct bond; each Alk is the same or different and represents an alkyl group or an aryl group; each X is the same or different and represents a halogen atom or a pseudohalide; and a, b, c, and d are the same or different and represent an integer of 0 to 4).

3. The anion exchange resin according to claim 2 , wherein the hydrophobic group comprises a bisphenol residue which is substituted with a halogen atom, a pseudohalide, an alkyl group, or an aryl group, as shown in the following formula (1);

(In the formula, Alk, X, a, b, c, and d have the same meaning as Alk, X, a, b, c, and d in said formula (2); each Z is the same or different and represents carbon atom or silicon atom; each R is the same or different and represents a silicon-containing group, a nitrogen-containing group, a phosphorus-containing group, an oxygen-containing group, a sulfur-containing group, or direct bond; I represents an integer of 1 or more; h, h′, h″, i i′, i″, j, and k are the same or different and represent an integer of 0 or more).

4. The anion exchange resin according to claim 3 , wherein in said formula (1), Z is a carbon atom; R is direct bond; X is fluorine atom; and h, h′, h″, i, i′, i″, j, and k are 0.

5. The anion exchange resin according to claim 1 , wherein the hydrophilic group comprises a fluorene residue as shown in the following formula (3);

(In the formula, Ion and Ion′ are the same or different and represent an anion exchange group; and y and z are the same or different and represent an integer of 2 to 20).

6. An electrolyte membrane, comprising the anion exchange resin according to claim 1 .

7. A binder for forming an electrode catalyst layer, comprising the anion exchange resin according claim 1 .

8. The anion exchange resin according to claim 2 , wherein the hydrophilic group comprises a fluorene residue as shown in the following formula (3);

(In the formula, Ion and Ion′ are the same or different and represent an anion exchange group; and y and z are the same or different and represent an integer of 2 to 20).

9. The anion exchange resin according to claim 3 , wherein the hydrophilic group comprises a fluorene residue as shown in the following formula (3);

(In the formula, Ion and Ion′ are the same or different and represent an anion exchange group; and y and z are the same or different and represent an integer of 2 to 20).

10. The anion exchange resin according to claim 4 , wherein the hydrophilic group comprises a fluorene residue as shown in the following formula (3);

(In the formula, Ion and Ion′ are the same or different and represent an anion exchange group; and y and z are the same or different and represent an integer of 2 to 20).

11. The electrolyte membrane according to claim 6 , wherein the hydrophobic group comprises a bisphenol residue which is substituted with a halogen atom, a pseudohalide, an alkyl group, or an aryl group, as shown in the following formula (2);

(In the formula, R represents a hydrocarbon group, a silicon-containing group, a nitrogen-containing group, a phosphorus-containing group, an oxygen-containing group, or a sulfur-containing group, which are substituted with a halogen atom or a pseudohalide, or direct bond; each Alk is the same or different and represents an alkyl group or an aryl group; each X is the same or different and represents a halogen atom or a pseudohalide; and a, b, c, and d are the same or different and represent an integer of 0 to 4).

12. The electrolyte membrane according to claim 11 , wherein the hydrophobic group comprises a bisphenol residue which is substituted with a halogen atom, a pseudohalide, an alkyl group, or an aryl group, as shown in the following formula (1);

(In the formula, Alk, X, a, b, c, and d have the same meaning as Alk, X, a, b, c, and d in said formula (2); each Z is the same or different and represents carbon atom or silicon atom; each R is the same or different and represents a silicon-containing group, a nitrogen-containing group, a phosphorus-containing group, an oxygen-containing group, a sulfur-containing group, or direct bond; I represents an integer of 1 or more; h, h′, h″, i, i′, i″, j, and k are the same or different and represent an integer of 0 or more).

13. The electrolyte membrane according to claim 12 , wherein in said formula (1), Z is a carbon atom; R is direct bond; X is fluorine atom; and h, h′, h″, i, i′, i″, j, and k are 0.

14. The electrolyte membrane according to claims 6 , wherein the hydrophilic group comprises a fluorene residue as shown in the following formula (3);

Assignees

• Univ Yamanashi
• Takahata Prec Co Ltd

Inventors

• Miyatake Kenji
• Miyake Junpei
• Ono Hideaki
• Shimada Manai
• Yokota Naoki
• YOSHIMURA Natsumi
• Takano Aoi
• Asazawa Koichiro
• Nishino Eriko
• Kuwabara Yui

Classifications

• Y02E60/50

  Fuel cells · CPC title

• H01M8/1046

  Mixtures of at least one polymer and at least one additive · CPC title

• H01M8/1037

  having silicon, e.g. sulfonated crosslinked polydimethylsiloxanes · CPC title

• C08J5/2262

  containing fluorine · CPC title

• C08J2365/00

  Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08J2307/00 - C08J2357/00, C08J2361/00 take precedence); Derivatives of such polymers · CPC title