IP Library Granted Patent US 10,734,663
Granted Patent B2
US 10,734,663 · App. 16/043,682 · Granted Aug 4, 2020

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

Inventors: Kenji Miyatake (Yamanashi, JP); Junpei Miyake (Yamanshi, JP); Hideaki Ono (Yamanashi, JP); Manai Shimada (Yamanashi, JP); Naoki Yokota (Yamanashi, JP); Natsumi Yoshimura (Yamanashi, JP); Aoi Takano (Shiga, JP); Koichiro Asazawa (Shiga, JP); Eriko Nishino (Shiga, JP); Yui Kuwabara (Shiga, JP)
Assignees: UNIVERSITY OF YAMANASHI; TAKAHATA PRECISION CO., LTD.
H01M8/1023C08J5/225C08J5/2237C08J5/2262H01M4/8668H01M8/1037H01M8/1039H01M8/1046C08J2365/00H01M2008/1095
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Quick Facts
Patent No.
US 10,734,663
App. No.
16/043,682
Granted
Aug 4, 2020
Kind
B2
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.

Claims (35)

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);

(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).

15. The binder for forming an electrode catalyst layer according to claim 7 , 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).

16. The binder for forming an electrode catalyst layer according to claim 15 , 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).

17. The binder for forming an electrode catalyst layer according to claim 16 , 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.

18. The binder for forming an electrode catalyst layer according to claim 7 , 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).

Assignments (3)
CHANGE OF ASSIGNEE'S ADDRESS Recorded Sep 14, 2021
From: TAKAHATA PRECISION CO., LTD.
To: TAKAHATA PRECISION CO., LTD.
Reel/Frame 057501/0278 →
CHANGE OF NAME Recorded Aug 19, 2019
From: TAKAHATA PRECISION JAPAN CO., LTD.
To: TAKAHATA PRECISION CO., LTD.
Reel/Frame 050092/0955 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2018
From: MIYATAKE, KENJI; MIYAKE, JUNPEI; ONO, HIDEAKI; SHIMADA, MANAI; YOKOTA, NAOKI; YOSHIMURA, NATSUMI; TAKANO, AOI; ASAZAWA, KOICHIRO; NISHINO, ERIKO; KUWABARA, YUI
To: UNIVERSITY OF YAMANASHI; TAKAHATA PRECISION JAPAN CO., LTD.
Reel/Frame 046443/0360 →
Priority Claims (1)
JP 2017-143135 · Jul 24, 2017 · national
Continuity (1)
Related Publication 20190027767A1 · Jan 24, 2019
Cited By (1)
US 12,624,157