IP Library Granted Patent US 8,470,895
Granted Patent B2
US 8,470,895 · App. 12/656,336 · Granted Jun 25, 2013

Polymer electrolyte membrane comprising alkylether graft chain and method of producing the same

Inventors: Yasunari Maekawa (Takasaki, JP); Kazuyuki Enomoto (Takasaki, JP); Nobuhiro Kihara (Hiratsuka, JP)
Assignees: Japan Atomic Energy Agency; Kanagawa University
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Quick Facts
Patent No.
US 8,470,895
App. No.
12/656,336
Granted
Jun 25, 2013
Kind
B2
Abstract

A method of producing an electrolyte membrane for use in a fuel cell, including: performing radiation-induced graft polymerization of a vinyl monomer having a nucleophilic functional group selected from an acylvinyl ether derivative, a styrene derivative, and a methacrylic acid derivative, with a polymer substrate having a fluorine-containing polymer, an olefin-containing polymer, or an aromatic polymer; deprotecting an ester bond of a graft chain on the polymer substrate introduced by the radiation-induced graft polymerization; and introducing an alkylethersulfonic acid structure into the nucleophilic functional group of the graft chain thus deprotected, by use of an electrophilic reagent selected from cyclic sulfonic acid ester and alkylhalide sulfonate.

Claims (11)

1. A method of producing an electrolyte membrane comprising alkylether graft chains for use in a fuel cell, comprising:

performing radiation-induced graft polymerization of a vinyl monomer having nucleophilic functional groups, the vinyl monomer selected from an acylvinyl ether derivative, a styrene derivative, and a methacrylic acid derivative, with a polymer substrate comprising a polymer selected from a fluorine-containing polymer, an olefinic polymer, and an aromatic polymer;

deprotecting the nucleophilic functional group, which is protected by an ester bond, of a graft chain on the polymer substrate introduced by the radiation-induced graft polymerization; and

introducing an alkylethersulfonic acid structure into the deprotected nucleophilic functional group of the graft chain, by use of an electrophilic reagent selected from cyclic sulfonic acid ester and alkylhalide-sulfonate.

2. The method of claim 1 , wherein:

the acylvinyl ether derivative is selected from the group consisting of vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate;

the styrene derivative is selected from the group consisting of 2-hydroxystyrene, 3-hydroxystyrene, 4-hydroxystyrene, 4-(methylhydroxystyrene), 4-(1-ethylhydroxystyrene), 4-(1-hydroxy-1-methylethylstyrene), 4-acetoxystyrene, 4-t-butyloxycarboxystyrene, and 4-acetoxymethylstyrene; and

the methacrylic acid derivative is selected from the group consisting of 1-hydroxymethylacrylic acid, 1-(1-hydroxyethyl)acrylic acid, methyl 1-hydroxymethyl acrylate, methyl 1-(1-hydroxyethyl) acrylate, ethyl 1-hydroxymethyl acrylate, ethyl 1-(1-hydroxyethyl) acrylate, 1-acetoxymethylacrylic acid, 1-(acetoxyethyl)acrylic acid, methyl 1-acetoxymethyl acrylate, and methyl 1-(acetoxyethyl) acrylate.

3. The method of claim 1 wherein:

the cyclic sulfonic acid ester is selected from the group consisting of 1,3-propanesultone, 1,4-butanesultone, 1,1,2,2-tetrafluoroethylsultone, and 1,1,2,2,3,3-hexafluoropropanesultone; and

the alkyl halide sulfonic acid is selected from the group consisting of sodium 2-bromoethylsulfonate and sodium 3-bromopropylsulfonate.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2019
From: JAPAN ATOMIC ENERGY AGENCY
To: NATIONAL INSTITUTES FOR QUANTUM AND RADIOLOGICAL SCIENCE AND TECHNOLOGY
Reel/Frame 048614/0521 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2010
From: MAEKAWA, YASUNARI; ENOMOTO, KAZUYUKI; KIHARA, NOBUHIRO
To: JAPAN ATOMIC ENERGY AGENCY; KANAGAWA UNIVERSITY
Reel/Frame 024343/0114 →
Priority Claims (1)
JP 2009-022352 · Feb 3, 2009 · national
Continuity (1)
Related Publication 20100216901A1 · Aug 26, 2010