CA2463429A1 - Crosslinkable aromatic resin having protonic acid group, and ion conductive polymer membrane, binder and fuel cell using the resin - Google Patents

Crosslinkable aromatic resin having protonic acid group, and ion conductive polymer membrane, binder and fuel cell using the resin Download PDF

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Publication number
CA2463429A1
CA2463429A1 CA002463429A CA2463429A CA2463429A1 CA 2463429 A1 CA2463429 A1 CA 2463429A1 CA 002463429 A CA002463429 A CA 002463429A CA 2463429 A CA2463429 A CA 2463429A CA 2463429 A1 CA2463429 A1 CA 2463429A1
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CA
Canada
Prior art keywords
aromatic
resin
crosslinkable
group
protonic acid
Prior art date
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Granted
Application number
CA002463429A
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French (fr)
Other versions
CA2463429C (en
Inventor
Junichi Ishikawa
Takashi Kuroki
Satoko Fujiyama
Takehiko Omi
Tomoyuki Nakata
Yuichi Okawa
Kazuhisa Miyazaki
Shigeharu Fujii
Shoji Tamai
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Mitsui Chemicals Inc
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Individual
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Publication of CA2463429A1 publication Critical patent/CA2463429A1/en
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Publication of CA2463429C publication Critical patent/CA2463429C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • C08G65/485—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/126—Polyphenylene oxides modified by chemical after-treatment
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
    • H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
    • H01M8/103—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having nitrogen, e.g. sulfonated polybenzimidazoles [S-PBI], polybenzimidazoles with phosphoric acid, sulfonated polyamides [S-PA] or sulfonated polyphosphazenes [S-PPh]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
    • H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. in situ polymerisation or in situ crosslinking
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
    • H01M8/1018—Polymeric electrolyte materials
    • H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
    • H01M8/1081—Polymeric electrolyte materials characterised by the manufacturing processes starting from solutions, dispersions or slurries exclusively of polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/20—Cross-linking
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2371/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/8605—Porous electrodes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/90—Selection of catalytic material
    • H01M4/92—Metals of platinum group
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/10—Fuel cells with solid electrolytes
    • H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Sustainable Development (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Energy (AREA)
  • Electrochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Fuel Cell (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Inert Electrodes (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

The invention provides a crosslinkable aromatic resin having a protonic acid group and a crosslinkable group, suitable for electrolytic membranes and binders used in fuel cells, etc., and electrolytic polymer membranes, binders and fuel cells using the resin. The crosslinkable aromatic resin has a crosslinkable group, which is not derived from the protonic acid group and can form a polymer network without any elimination component. This resin exhibits excellent ion conductivity, heat resistance, water resistance, adhesion property and low methanol permeability.
Preferably, the crosslinkable group is composed of a C1 to C10 alkyl group directly bonded to the aromatic ring and a carbonyl group, or a carbon-carbon double bond or triple bond. The aromatic resins such as aromatic polyethers, aromatic polyamides, aromatic polyimides, aromatic polyamideimides, aromatic polyazoles,etc., which contain such a crosslinkable group, are preferred as the crosslinkable aromatic resins having a protonic acid group and a crosslinkable group.
CA002463429A 2001-10-10 2002-10-10 Crosslinkable aromatic resin having protonic acid group, and ion conductive polymer membrane, binder and fuel cell using the resin Expired - Fee Related CA2463429C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2001312799 2001-10-10
JP2001-312799 2001-10-10
JP2002-182252 2002-06-21
JP2002182252 2002-06-21
PCT/JP2002/010536 WO2003033566A1 (en) 2001-10-10 2002-10-10 Crosslinkable aromatic resins having protonic acid groups, and ion-conductive polymer membranes, binders, and fuel cells made by using the same

Publications (2)

Publication Number Publication Date
CA2463429A1 true CA2463429A1 (en) 2003-04-24
CA2463429C CA2463429C (en) 2008-07-29

Family

ID=26623831

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002463429A Expired - Fee Related CA2463429C (en) 2001-10-10 2002-10-10 Crosslinkable aromatic resin having protonic acid group, and ion conductive polymer membrane, binder and fuel cell using the resin

Country Status (9)

Country Link
US (1) US7345135B2 (en)
EP (1) EP1457511B1 (en)
JP (1) JP4076951B2 (en)
KR (2) KR100660433B1 (en)
CN (1) CN100462389C (en)
CA (1) CA2463429C (en)
DE (1) DE60232993D1 (en)
TW (1) TWI236486B (en)
WO (1) WO2003033566A1 (en)

Families Citing this family (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4501052B2 (en) * 2002-01-24 2010-07-14 東洋紡績株式会社 Thermally crosslinkable polymer solid electrolyte, polymer solid electrolyte membrane and method for producing the same
US7332530B2 (en) * 2002-08-02 2008-02-19 Celanese Ventures Gmbh Proton-conducting polymer membrane comprising a polymer with sulphonic acid groups and use thereof in fuel cells
DE10258175A1 (en) * 2002-12-12 2004-07-08 General Motors Corp., Detroit Block copolymers for use as solid polymer electrolytes e.g. in fuel cells have a segment with acidic substituents for proton transport and an acid-free segment giving mechanical integrity
US7816057B2 (en) * 2003-01-15 2010-10-19 Sendyne Corporation Fuel supply method for direct methanol fuel cell
JP4812248B2 (en) * 2003-01-22 2011-11-09 日東電工株式会社 Fuel cell
JP4135558B2 (en) 2003-05-21 2008-08-20 Ｊｓｒ株式会社 Polyarylene having sulfonic acid group and method for producing the same, and proton conducting membrane for direct methanol fuel cell
JP4496718B2 (en) * 2003-06-06 2010-07-07 宇部興産株式会社 POLYMER ELECTROLYTE MEMBRANE AND METHOD FOR PRODUCING THE SAME
US20050042489A1 (en) * 2003-07-11 2005-02-24 Kenji Fukuta Laminate useful as a membrane-electrode assembly for fuel cells, production process therefor and a fuel cell provided with the laminate
JP4720091B2 (en) * 2004-02-27 2011-07-13 東洋紡績株式会社 Ion exchange membrane
JP4955198B2 (en) * 2003-09-19 2012-06-20 Ｊｓｒ株式会社 Membrane-electrode structure for polymer electrolyte fuel cell
JP2005162772A (en) 2003-11-28 2005-06-23 Jsr Corp Proton conductor composition and proton conducting membrane
DE602004016469D1 (en) 2003-12-09 2008-10-23 Honda Motor Co Ltd Membrane electrode assembly and polymer electrolyte fuel cell containing the same
KR100953545B1 (en) * 2004-03-23 2010-04-21 삼성에스디아이 주식회사 Supported catalyst and its manufacturing method
US9346673B2 (en) 2004-06-23 2016-05-24 Samsung Sdi Co., Ltd. Electrode for fuel cell, membrane-electrode assembly for fuel cell comprising the same, fuel cell system comprising the same, and method for preparing the electrode
US8288058B2 (en) 2004-07-23 2012-10-16 Mitsui Chemicals, Inc. Binder for fuel cell, composition for forming electrode, electrode, and fuel cell using the electrode
KR101232445B1 (en) * 2004-09-03 2013-02-12 도레이 카부시키가이샤 Polyelectrolyte material, polyelectrolyte component, membrane electrode composite body, and polyelectrolyte type fuel cell
KR100578981B1 (en) 2004-09-08 2006-05-12 삼성에스디아이 주식회사 Electrode for fuel cell, fuel cell system comprising same
JP2006100058A (en) * 2004-09-29 2006-04-13 Fujitsu Ltd Electrolyte composition, solid electrolyte membrane and polymer electrolyte fuel cell
US7972725B2 (en) * 2004-11-08 2011-07-05 3M Innovative Properties Company Polyimide electrode binders
KR100669456B1 (en) * 2004-11-26 2007-01-15 삼성에스디아이 주식회사 Electrode for fuel cell, fuel cell comprising same and method for manufacturing electrode for fuel cell
KR100658675B1 (en) 2004-11-26 2006-12-15 삼성에스디아이 주식회사 Electrode for fuel cell, fuel cell comprising same and method for manufacturing electrode for fuel cell
JP4773085B2 (en) * 2004-12-24 2011-09-14 旭化成イーマテリアルズ株式会社 Polyazole solution
KR20060087140A (en) 2005-01-28 2006-08-02 삼성에스디아이 주식회사 Polymer electrolyte membrane and fuel cell employing same
JP4867174B2 (en) * 2005-02-14 2012-02-01 東レ株式会社 POLYMER ELECTROLYTE MATERIAL, POLYMER ELECTROLYTE MEMBRANE, MEMBRANE ELECTRODE COMPOSITION AND POLYMER ELECTROLYTE TYPE FUEL CELL USING SAME
JP5044132B2 (en) * 2005-07-07 2012-10-10 富士フイルム株式会社 Manufacturing method and manufacturing equipment of solid electrolyte film
JP5044131B2 (en) 2005-07-07 2012-10-10 富士フイルム株式会社 Production method and production facility for solid electrolyte multilayer film
KR100684797B1 (en) 2005-07-29 2007-02-20 삼성에스디아이 주식회사 Electrode for fuel cell, membrane-electrode assembly comprising same and fuel cell system comprising same
KR100707163B1 (en) 2005-10-12 2007-04-13 삼성에스디아이 주식회사 Solid acid, polymer electrolyte membrane containing same and fuel cell employing same
US7598337B2 (en) * 2005-12-20 2009-10-06 General Electric Company Mixed-sulfonation block copolymers
JP4688157B2 (en) * 2005-12-28 2011-05-25 トヨタ自動車株式会社 Method for producing catalyst for fuel cell electrode
KR101255538B1 (en) 2006-02-22 2013-04-16 삼성에스디아이 주식회사 Sulfonated copolymer comprising crosslinkable functional group and fuel cell comprising polymerization product of the same
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TWI456826B (en) * 2007-02-22 2014-10-11 Toray Industries Resins for binder for electrodes of lithium ion secondary batteries, compositions and pastes containing the same and electrodes of lithium ion secondary batteries using the same
JP5412718B2 (en) * 2007-09-05 2014-02-12 東レ株式会社 POLYMER ELECTROLYTE MOLDED MANUFACTURING METHOD, POLYMER ELECTROLYTE MATERIAL, POLYMER ELECTROLYTE COMPONENT, MEMBRANE ELECTRODE COMPOSITE AND POLYMER ELECTROLYTE FUEL CELL
KR100934529B1 (en) * 2007-10-11 2009-12-29 광주과학기술원 Sulfonated poly (arylene ether) copolymer having a crosslinked structure inside the polymer chain, sulfonated poly (arylene ether) copolymer having a crosslinked structure inside and at the end of the polymer chain, and a polymer electrolyte membrane using the same
EP2048182A1 (en) * 2007-10-11 2009-04-15 Gwangju Institute of Science and Technology Sulfonate poly(arylene ether) having crosslinkable moiety combined in chain of polymer, sulfonated poly(arylene ether) having crosslinkable moieties combined in polymer and at polymer end group, and polymer electrolyte membrane using sulfonated poly(arylene ether)
KR100936069B1 (en) * 2007-10-25 2010-01-12 연세대학교 산학협력단 Semi-crosslinked polymer membrane, preparation method thereof and direct methanol fuel cell comprising the same
JP2009193682A (en) * 2008-02-12 2009-08-27 Mitsubishi Gas Chem Co Inc Method for producing membrane-electrode assembly
EP2344568B1 (en) 2008-09-23 2017-12-20 Nexam Chemical AB Acetylenic polyamide
WO2010074625A1 (en) * 2008-12-22 2010-07-01 Nexam Chemical Ab Acetylenic aromatic polyether
WO2011136029A1 (en) * 2010-04-28 2011-11-03 国立大学法人神戸大学 Semi-permeable composite membrane
JP2014502776A (en) * 2010-12-20 2014-02-03 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー High molecular weight ionomers and ion conductive compositions for use as one or more electrodes in fuel cells
EP2948423B1 (en) * 2013-01-28 2022-08-31 Delsper LP Extrusion-resistant compositions for sealing and wear components
WO2015066496A1 (en) 2013-11-01 2015-05-07 Virginia Tech Intellectual Properties, Inc. Crosslinked polymer compositions for gas separation membranes
FR3024146B1 (en) * 2014-07-23 2018-02-16 Cdp Innovation NOVEL POLYMERS CONTAINING BIS (SULFONYL) GRAFTED LITHIUM OR SODIUM SALTS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS ELECTROLYTES FOR BATTERIES
CN104557532B (en) * 2015-01-13 2017-03-01 西安力邦制药有限公司 Bigeminy benzene derivative and its application
KR101791528B1 (en) 2015-09-09 2017-10-31 한국화학연구원 Crosslinker containing electron withdrawing group for ion exchangable polymer, ion exchangable-crosslinked polymer crosslinked by the crosslinker and use thereof
KR101732878B1 (en) 2016-01-29 2017-05-08 경상대학교산학협력단 Anion-exchange membrane based on polyether ether ketone, preparation method thereof and anion-exchange membrane fuel cell comprising the same
JP7035037B6 (en) * 2016-10-11 2023-12-18 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． Blocked poly(etheretherketone) copolymers and corresponding synthetic methods and articles
JP7254726B2 (en) * 2017-06-26 2023-04-10 ビーエーエスエフ ソシエタス・ヨーロピア Novel membrane polymers and membranes
CN110914336A (en) * 2017-07-20 2020-03-24 巴斯夫欧洲公司 Sulfonated polyaryl ether sulfone and its membrane
US10364324B2 (en) 2017-08-17 2019-07-30 The United States of Ameirca as represented by the Secretary of the Air Force Poly(2,6-dimethyl-1,4-phenylene-oxide) derivatives with sulfonyl pendant groups and methods therefor
DE102018119446A1 (en) * 2018-08-09 2020-02-13 Carl Freudenberg Kg Crosslinking of polyaryl ether ketones
JP7418985B2 (en) * 2018-09-28 2024-01-22 太陽ホールディングス株式会社 Curable compositions, dry films, cured products, and electronic components
CN111393580B (en) * 2020-04-02 2022-12-13 宁夏清研高分子新材料有限公司 Polyarylethersulfone composite material and preparation method thereof
CN111403666B (en) * 2020-04-13 2022-12-20 上海极紫科技有限公司 Composition of high-temperature-resistant lithium battery diaphragm and preparation and crosslinking methods thereof
CN112915818B (en) * 2021-01-20 2022-05-20 北京化工大学 Heat-induced cross-linked phenolphthalein-based polybenzoxazole gas separation membrane material and preparation method thereof
WO2023001793A1 (en) * 2021-07-20 2023-01-26 Green Hydrogen Systems Improved durability of diaphragm for higher temperature electrolysis
CN118126505B (en) * 2024-05-08 2024-07-05 成都紫江包装有限公司 Plastic bottle and forming process thereof

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2002A (en) * 1841-03-12 Tor and planter for plowing
JPS5291788A (en) 1976-01-27 1977-08-02 Kanegafuchi Chem Ind Co Ltd Production of ion exchange membrane
JPS5299982A (en) 1976-02-17 1977-08-22 Kanegafuchi Chem Ind Co Ltd Production of ion exchanger
JPS63305904A (en) 1987-06-08 1988-12-13 Asahi Chem Ind Co Ltd Modifying method for sulfonic acid-type semi permeable membrane
JPH02248434A (en) 1989-03-22 1990-10-04 Asahi Glass Co Ltd Improved cation exchanger
JP3072850B2 (en) 1990-09-21 2000-08-07 旭硝子株式会社 Cation exchange membrane
JPH04144062A (en) 1990-10-04 1992-05-18 Toshiba Corp Manufacture of electrolyte matrix for fuel cell
EP0574791B1 (en) * 1992-06-13 1999-12-22 Aventis Research & Technologies GmbH & Co. KG Polymer electrolyte membrane and process for its manufacture
WO1996029359A1 (en) * 1995-03-20 1996-09-26 Hoechst Aktiengesellschaft Polymer electrolytes and process for their production
US5795496A (en) 1995-11-22 1998-08-18 California Institute Of Technology Polymer material for electrolytic membranes in fuel cells
JP3861367B2 (en) 1996-04-18 2006-12-20 住友化学株式会社 POLYMER ELECTROLYTE, MANUFACTURING METHOD THEREOF, AND FUEL CELL COMPRISING THE SAME
FR2748485B1 (en) * 1996-05-07 1998-08-07 Commissariat Energie Atomique SULPHONATED POLYIMIDES, MEMBRANES PREPARED THEREWITH, AND FUEL CELL DEVICE COMPRISING SUCH MEMBRANES
DE19622337C1 (en) 1996-06-04 1998-03-12 Dlr Deutsche Forschungsanstalt Networking of modified engineering thermoplastics
JP3970390B2 (en) 1997-08-22 2007-09-05 旭化成株式会社 Membrane-electrode assembly for solid polymer fuel cell
US6090895A (en) 1998-05-22 2000-07-18 3M Innovative Properties Co., Crosslinked ion conductive membranes
CA2343184C (en) * 1998-09-11 2010-06-29 Victrex Manufacturing Limited Ion-exchange polymers
JP3692274B2 (en) 1999-02-09 2005-09-07 日清紡績株式会社 Fuel cell separator and solid polymer fuel cell
US6180559B1 (en) 1999-03-02 2001-01-30 Eastman Chemical Company Supported catalysts and catalyst support materials and process for the manufacture of 1,2-epoxybutane
DE19919708A1 (en) 1999-04-30 2001-03-01 Univ Stuttgart Gradual alkylation of polymeric amines
RU2252022C2 (en) * 1999-08-30 2005-05-20 Дебиофарм С.А. Stable pharmaceutical preparation of oxaliplatinum for parenteral injection
FR2799198B1 (en) * 1999-10-04 2002-05-03 Commissariat Energie Atomique SULPHONATED POLYMIDES, MEMBRANES PREPARED THEREWITH AND FUEL CELL DEVICE COMPRISING SUCH MEMBRANES
US7361729B2 (en) 2000-09-20 2008-04-22 Virginia Tech Intellectual Properties, Inc. Ion-conducting sulfonated polymeric materials
JP2002105199A (en) * 2000-09-29 2002-04-10 Kanegafuchi Chem Ind Co Ltd Proton conductive polyimide resin composition, proton conductive polyimide membrane and polymer electrolyte fuel cell using the same
JP2002121281A (en) * 2000-10-18 2002-04-23 Kanegafuchi Chem Ind Co Ltd A method for producing a polyamic acid copolymer, a polyimide copolymer, and a polyimide film.
JP4161249B2 (en) 2001-04-24 2008-10-08 東洋紡績株式会社 Ion conductive aromatic polyether
JP3703016B2 (en) * 2001-06-01 2005-10-05 住友電気工業株式会社 POLYMER ELECTROLYTE MEMBRANE AND METHOD FOR PRODUCING THE SAME
JP2002367627A (en) * 2001-06-04 2002-12-20 Sumitomo Electric Ind Ltd Sulfonated polyimide polymer electrolyte membrane and method for producing the same
JP2003068327A (en) 2001-08-28 2003-03-07 Kanegafuchi Chem Ind Co Ltd Fuel cell membrane
JP4208455B2 (en) 2001-11-16 2009-01-14 東洋紡績株式会社 Sulfonated fluorine-containing polymer, resin composition containing the same, and polymer electrolyte membrane
JP4501052B2 (en) 2002-01-24 2010-07-14 東洋紡績株式会社 Thermally crosslinkable polymer solid electrolyte, polymer solid electrolyte membrane and method for producing the same
JP4517272B2 (en) 2002-01-24 2010-08-04 東洋紡績株式会社 Photocrosslinkable polymer solid electrolyte, cross-linked polymer solid electrolyte membrane and method for producing the same
JP3973503B2 (en) 2002-07-11 2007-09-12 三井化学株式会社 Ion conductive binder for fuel cell, electrode forming composition and varnish, and fuel cell

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