Anion Exchange Resin, Method For Producing Thereof, Electrolyte Membrane For Fuel Cell, Binder For Forming Electrode Catalyst Layer, Fuel Cell Electrode Catalyst Layer And Fuel Cell

Patent metadata

Field	Value
Publication number	US-2018265626-A1
Application number	US-201615762085-A
Country	US
Kind code	A1
Filing date	Sep 20, 2016
Priority date	Sep 22, 2015
Publication date	Sep 20, 2018
Grant date	—

Abstract

Provided are an anion exchange resin being capable of producing an electrolyte membrane for a fuel cell, a binder for forming an electrode catalyst layer and a fuel cell electrode catalyst layer, which have an improved physical property (anion conductivity); a method for producing thereof; an electrolyte membrane for a fuel cell, a binder for forming an electrode catalyst layer and a fuel cell electrode catalyst layer produced from the anion exchange resin; and a fuel cell having the electrolyte membrane or the electrode catalyst layer.
For example, the anion exchange resin is obtained by reacting a hydrophobic monomer with an aminoalkyl group-containing monomer, in which the hydrophobic monomer is composed of one aromatic ring or a plurality of aromatic rings to which two halogen atoms are bonded, and the aminoalkyl group-containing monomer is composed of one aromatic ring or a plurality of aromatic rings to which two halogen atoms are bonded and an aminoalkyl group is introduced; and by quaternizing the amino group. In the anion exchange resin, a divalent hydrophobic group formed by the residue of the hydrophobic monomer, and a divalent hydrophilic group formed by the residue of the quaternized aminoalkyl group-containing monomer are bonded via direct bond.

First claim

1 . An anion exchange resin, produced by:
(A) preparing a hydrophobic monomer or a hydrophobic oligomer,
wherein the hydrophobic monomer is composed of one aromatic ring, or is composed of a plurality of aromatic rings which are bonded 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic ring(s); and
wherein the hydrophobic oligomer is composed of a plurality of aromatic rings which are bonded 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 direct bond, wherein the plurality of aromatic rings are bonded repeatedly 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic rings at both terminals; (B) preparing an aminoalkyl group-containing monomer,
wherein the aminoalkyl group-containing monomer is composed of one aromatic ring, or is composed of a plurality of aromatic rings which are bonded 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic ring(s), and wherein at least one aromatic rings has an aminoalkyl group;
(C) reacting the hydrophobic monomer or the hydrophobic oligomer with the aminoalkyl group-containing monomer to synthesize a polymer; and (D) quaternizing the amino group in the polymer; wherein the residue of the hydrophobic monomer or the hydrophobic oligomer forms a divalent hydrophobic group; wherein the quaternized amino group forms an anion exchange group; wherein the residue of the quaternized aminoalkyl group-containing monomer forms a divalent hydrophilic group; and wherein the divalent hydrophobic group and the divalent hydrophilic group are bonded via direct bond.

2 . The anion exchange resin according to claim 1 , wherein the hydrophobic group comprises:
a bisphenol residue which may be substituted with a halogen atom, a pseudohalide or an alkyl group, as shown in the following formula (2); and/or an o-, m- or p-phenylene group which may be substituted with a halogen atom, a pseudohalide or an alkyl 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, a sulfur-containing group, an aromatic group, or direct bond, each of which may be substituted with a halogen atom or a pseudohalide; each Alk is the same or different and represents an alkyl group; each X is the same or different and represents a halogen atom or a pseudohalide; and p 1 , p 2 , q 1 , and q 2 are the same or different and represent an integer of 0 to 4.)

(In the formula, Alk represents an alkyl group; X represents a halogen atom or a pseudohalide; and p 1 and q 1 are the same or different and represent an integer of 0 to 4.)

3 . The anion exchange resin according to claim 1 , wherein the hydrophilic group comprises:
a bisphenol fluorene residue substituted with a substituent group having the anion exchange group, as shown in the following formula (3); and/or an o-, m- or p-phenylene group substituted with a substituent group having the anion exchange group, as shown in the following formula (3′).

(In the formula, R represents a hydrocarbon group, a silicon-containing group, a nitrogen-containing group, a phosphorus-containing group, an oxygen-containing group, a sulfur-containing group, an aromatic group, or direct bond, each of which may be substituted with a substituent group having the anion exchange group; each Alk is the same or different and represents an alkyl group; each X is the same or different and represents a halogen atom or a pseudohalide; each Ion is the same or different and represents a substituent group having an anion exchange group; p 1 , p 2 , q 1 , and q 2 are the same or different and represent an integer of 0 to 4; r 1 , r 2 , and r 3 are the same or different and represent an integer of 0 to 4, and at least one of r 1 , r 2 , and r 3 represents 1 or more.)

(In the formula, Alk represents an alkyl group; X represents a halogen atom or a pseudohalide; Ion represents a substituent group having an anion exchange group; p 1 and q 1 are represent an integer of 0 to 4; and r 1 represents an integer of 1 to 4.)

4 . An electrolyte membrane for a fuel cell, comprising the anion exchange resin according to claim 1 .

5 - 10 . (canceled)

11 . A method for producing an anion exchange resin, comprising:
(A) preparing a hydrophobic monomer or a hydrophobic oligomer,
wherein the hydrophobic monomer is composed of one aromatic ring, or is composed of a plurality of aromatic rings which are bonded 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic ring(s); and
wherein the hydrophobic oligomer is composed of a plurality of aromatic rings which are bonded 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 direct bond, wherein the plurality of aromatic rings are bonded repeatedly 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic rings at both terminals; (B) preparing an aminoalkyl group-containing monomer,
wherein the aminoalkyl group-containing monomer is composed of one aromatic ring, or is composed of a plurality of aromatic rings which are bonded 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 direct bond, and wherein two halogen atoms, pseudohalides or boronate groups are bonded to the aromatic ring(s), and wherein at least one aromatic rings has an aminoalkyl group;
(C) reacting the hydrophobic monomer or the hydrophobic oligomer with the aminoalkyl group-containing monomer to synthesize a polymer; and (D) quaternizing the amino gro

Assignees

• Univ Yamanashi
• Takahata Prec Japan Co Ltd

Inventors

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

Classifications

• C08G61/12 Primary

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• C08G2261/72

  Derivatisation · CPC title

• C08G2261/146

  Side-chains containing halogens · CPC title

• C08G65/40

  from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group · CPC title

• H01M8/0202

  Collectors; Separators, e.g. bipolar separators; Interconnectors · CPC title