JP2007517095A - 直接フッ素化により架橋されたポリマー電解質膜 - Google Patents
直接フッ素化により架橋されたポリマー電解質膜 Download PDFInfo
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/1023—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes
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- C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
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- 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
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Abstract
Description
YOSO2−CF2−CF2−CF2−CF2−O−(ポリマー 骨格)
(式中、Yは、H+またはアルカリ金属カチオンなどの1価のカチオンである)で表される高フッ素化骨格と反復ペンダント基とを含有する。一般には、この膜はキャスト膜である。一般には、このポリマーは、22,000を超える水和物を有する。一般には、このポリマーは、800〜1200の当量を有する。
ポリマーの「当量」(EW)とは、基の1つの当量を中和するポリマーの量を意味する。
ポリマーの「水和物」(HP)とは、ポリマーの当量を掛けた膜中にあるスルホン酸基の1当量当たりの膜に吸収された水の当量(モル)の数を意味する。
「高フッ素化」とは、フッ素を40重量%以上、一般には50重量%以上、さらに一般には60重量%以上を含有することを意味する。
R1の例として、
−(CF2)n−(式中nは、1、2、3、4、5、6、7、8、9、10、11、12、13、14、または15)
(−CF2CF(CF3)−)n(式中nは、1、2、3、4、または5)
(−CF(CF3)CF2−)n(式中nは、1、2、3、4、または5)
(−CF2CF(CF3)−)n−CF2−(式中nは、1、2、3、または4)
(−O−CF2CF2−)n(式中nは、1、2、3、4、5、6、または7)
(−O−CF2CF2CF2−)n(式中nは、1、2、3、4、または5)
(−O−CF2CF2CF2CF2−)n(式中nは、1、2、または3)
(−O−CF2CF(CF3)−)n(式中nは、1、2、3、4、または5)
(−O−CF2CF(CF2CF3)−)n(式中nは、1、2、または3)
(−O−CF(CF3)CF2−)n(式中nは、1、2、3、4、または5)
(−O−CF(CF2CF3)CF2−)n(式中nは、1、2、または3)
(−O−CF2CF(CF3)−)n−O−CF2CF2−(式中nは、1、2、3、または4)
(−O−CF2CF(CF2CF3)−)n−O−CF2CF2−(式中nは、1、2、または3)
(−O−CF(CF3)CF2−)n−O−CF2CF2−(式中nは、1、2、3、または4)
(−O−CF(CF2CF3)CF2−)n−O−CF2CF2−(式中nは、1、2、または3)
−O−(CF2)n−(式中nは、1、2、3、4、5、6、7、8、9、10、11、12、13、または14)が挙げられる。
Rは、一般には、−O−CF2CF2CF2CF2−SO2Xまたは−O−CF2−CF(CF3)−O−CF2−CF2−SO2Xおよび最も一般には、−O−CF2CF2CF2CF2−SO2X(式中Xは、ハロゲンである)である。この−SO2X基は、重合過程において最も一般には、−SO2Fである。すなわち、Xは、Fであり、フッ化スルホニル基は、一般には、イオノマーとしてフルオロポリマーを使用する前に−SO3Hに加水分解する。
Claims (10)
- a)ハロゲン化スルホニル基を含む第1のペンダント基を含有する非ペルフルオロ化ポリマーを提供する工程と、
b)前記ポリマーを直接フッ素化する工程と、を含む、架橋ポリマーを製造する方法。 - a)非ペルフルオロ化ポリマーである第1のポリマーと、ハロゲン化スルホニル基を含む第1のペンダント基を含む第2のポリマーとのポリマー混合物を提供する工程と、
b)前記ポリマー混合物を直接フッ素化する工程と、を含む、架橋ポリマー混合物を製造する方法。 - 前記第1のポリマーがテトラフルオロエチレン(TFE)と、ヘキサフルオロプロピレン(HFP)とフッ化ビニリデン(VDF)とのターポリマーである、請求項2に記載の方法。
- 前記ポリマーを直接フッ素化する工程b)の後に、
d)前記ハロゲン化スルホニル基をスルホン酸基に転化する工程をさらに含む、請求項1〜3のいずれか一項に記載の方法。 - 前記第1のペンダント基が式−R1−SO2X(式中Xは、ハロゲンであり、R1 は、1〜15個の炭素原子と0〜4個の酸素原子とを含む分枝状または非分枝状ペルフルオロアルキルまたはペルフルオロエーテル基である)で表される、請求項1〜4のいずれか一項に記載の方法。
- 前記ポリマーを直接フッ素化する工程b)の前に、
c)前記ポリマーを膜に成形する工程をさらに含む、請求項1〜5のいずれか一項に記載の方法。 - 工程c)が、多孔性の担体マトリックスに前記ポリマーを吸収させることを含む、請求項6に記載の方法。
- 前記膜の厚さが90ミクロン以下である、請求項6または7に記載の方法。
- 請求項1〜5のいずれか一項に記載の方法で製造した架橋ポリマーを含む、ポリマー電解質膜。
- 請求項6〜8のいずれか一項に記載の方法で製造したポリマー電解質膜。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US10/738,083 US7173067B2 (en) | 2003-12-17 | 2003-12-17 | Polymer electrolyte membranes crosslinked by direct fluorination |
PCT/US2004/038966 WO2005061559A1 (en) | 2003-12-17 | 2004-11-19 | Polymer electrolyte membranes crosslinked by direct fluorination |
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JP2007517095A true JP2007517095A (ja) | 2007-06-28 |
JP2007517095A5 JP2007517095A5 (ja) | 2008-01-17 |
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JP2006545669A Pending JP2007517095A (ja) | 2003-12-17 | 2004-11-19 | 直接フッ素化により架橋されたポリマー電解質膜 |
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US (2) | US7173067B2 (ja) |
EP (1) | EP1694718A1 (ja) |
JP (1) | JP2007517095A (ja) |
KR (1) | KR20070008544A (ja) |
CN (1) | CN100560612C (ja) |
CA (1) | CA2550285A1 (ja) |
TW (1) | TW200533687A (ja) |
WO (1) | WO2005061559A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104448369A (zh) * | 2014-11-14 | 2015-03-25 | 南京理工大学 | 一类接枝全交联型质子交换膜及其制备方法 |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7071271B2 (en) * | 2003-10-30 | 2006-07-04 | 3M Innovative Properties Company | Aqueous emulsion polymerization of functionalized fluoromonomers |
US7259208B2 (en) * | 2003-11-13 | 2007-08-21 | 3M Innovative Properties Company | Reinforced polymer electrolyte membrane |
US7074841B2 (en) * | 2003-11-13 | 2006-07-11 | Yandrasits Michael A | Polymer electrolyte membranes crosslinked by nitrile trimerization |
US7265162B2 (en) * | 2003-11-13 | 2007-09-04 | 3M Innovative Properties Company | Bromine, chlorine or iodine functional polymer electrolytes crosslinked by e-beam |
US7179847B2 (en) * | 2003-11-13 | 2007-02-20 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by e-beam |
US7060756B2 (en) * | 2003-11-24 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolyte with aromatic sulfone crosslinking |
US7112614B2 (en) * | 2003-12-08 | 2006-09-26 | 3M Innovative Properties Company | Crosslinked polymer |
US7060738B2 (en) * | 2003-12-11 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by ultraviolet radiation |
US7214740B2 (en) * | 2005-05-03 | 2007-05-08 | 3M Innovative Properties Company | Fluorinated ionomers with reduced amounts of carbonyl end groups |
US20070218334A1 (en) * | 2006-03-16 | 2007-09-20 | Bonorand Lukas M | Methods for making sulfonated non-aromatic polymer electrolyte membranes |
WO2008054420A2 (en) * | 2005-12-22 | 2008-05-08 | E. I. Du Pont De Nemours And Company | Chemically stabilized ionomers containing inorganic fillers |
WO2007109106A1 (en) * | 2006-03-16 | 2007-09-27 | Bdf Ip Holdings Ltd. | Fluorination of a porous hydrocarbon-based polymer for use as composite membrane |
US20080199753A1 (en) * | 2007-02-19 | 2008-08-21 | Gm Global Technology Operations, Inc. | Fluorine Treatment of Polyelectrolyte Membranes |
CN103788280B (zh) * | 2008-04-24 | 2016-08-17 | 3M创新有限公司 | 质子传导材料 |
US8785023B2 (en) * | 2008-07-07 | 2014-07-22 | Enervault Corparation | Cascade redox flow battery systems |
US7820321B2 (en) * | 2008-07-07 | 2010-10-26 | Enervault Corporation | Redox flow battery system for distributed energy storage |
US8480917B2 (en) | 2008-12-12 | 2013-07-09 | Samsung Electronics Co., Ltd. | Solid electrolyte polymer, polymer actuator using cross-linked polyvinylidene fluoride-based polymer, and method of manufacturing the polymer actuator |
US9450262B2 (en) * | 2009-06-12 | 2016-09-20 | Solvay Specialty Polymers Italy S.P.A. | Fluoroionomers dispersions having a low surface tension, low liquid viscosity and high solid content |
CN101817228B (zh) * | 2010-04-12 | 2014-06-18 | 江苏昊华光伏科技有限公司 | 基于pvdf的多层共密合薄膜的制备方法及其产品 |
WO2011129967A2 (en) | 2010-04-16 | 2011-10-20 | 3M Innovative Properties Company | Proton conducting materials |
EP2577787B1 (en) | 2010-05-25 | 2016-10-05 | 3M Innovative Properties Company | Reinforced electrolyte membrane |
US8916281B2 (en) | 2011-03-29 | 2014-12-23 | Enervault Corporation | Rebalancing electrolytes in redox flow battery systems |
US8980484B2 (en) | 2011-03-29 | 2015-03-17 | Enervault Corporation | Monitoring electrolyte concentrations in redox flow battery systems |
WO2018077668A1 (en) * | 2016-10-28 | 2018-05-03 | Solvay Specialty Polymers Italy S.P.A. | Method for cross-linking polymers |
JP6569653B2 (ja) * | 2016-12-08 | 2019-09-04 | 株式会社村田製作所 | 巻線型コイル部品 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4844360A (ja) * | 1971-09-08 | 1973-06-26 | ||
US3853828A (en) * | 1973-11-21 | 1974-12-10 | Us Army | Process for crosslinking fluorocarbon polymers |
JP2001283866A (ja) * | 2000-03-31 | 2001-10-12 | Japan Storage Battery Co Ltd | 燃料電池用ガス拡散電極およびその製造方法 |
JP2002324559A (ja) * | 2001-02-23 | 2002-11-08 | Toyota Central Res & Dev Lab Inc | 多官能化電解質及びこれを用いた電気化学デバイス並びに多官能化電解質の製造方法 |
JP2003346815A (ja) * | 2002-05-30 | 2003-12-05 | Toyota Central Res & Dev Lab Inc | 膜電極接合体、及びその製造方法 |
WO2004066426A1 (ja) * | 2003-01-20 | 2004-08-05 | Asahi Glass Company, Limited | 固体高分子型燃料電池用電解質材料の製造方法及び固体高分子型燃料電池用膜電極接合体 |
Family Cites Families (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3282875A (en) * | 1964-07-22 | 1966-11-01 | Du Pont | Fluorocarbon vinyl ether polymers |
GB1184321A (en) | 1968-05-15 | 1970-03-11 | Du Pont | Electrochemical Cells |
US3635926A (en) * | 1969-10-27 | 1972-01-18 | Du Pont | Aqueous process for making improved tetrafluoroethylene / fluoroalkyl perfluorovinyl ether copolymers |
US4000356A (en) * | 1972-06-19 | 1976-12-28 | Dynamit Nobel Aktiengesellschaft | Process for the preparation of thermoplastically workable fluoro-olefin polymers |
US4169023A (en) * | 1974-02-04 | 1979-09-25 | Tokuyama Soda Kabushiki Kaisha | Electrolytic diaphragms, and method of electrolysis using the same |
US4035565A (en) * | 1975-03-27 | 1977-07-12 | E. I. Du Pont De Nemours And Company | Fluoropolymer containing a small amount of bromine-containing olefin units |
US4073752A (en) | 1975-06-02 | 1978-02-14 | The B. F. Goodrich Company | High normality ion exchange membranes containing entrapped electrostatically bulky multicharged ions and method of production |
GB1518387A (en) | 1975-08-29 | 1978-07-19 | Asahi Glass Co Ltd | Fluorinated cation exchange membrane and use thereof in electrolysis of an alkali metal halide |
US4508603A (en) * | 1976-08-22 | 1985-04-02 | Asahi Glass Company Ltd. | Fluorinated cation exchange membrane and use thereof in electrolysis of an alkali metal halide |
JPS5329291A (en) | 1976-09-01 | 1978-03-18 | Toyo Soda Mfg Co Ltd | Cation exchange membrane and production of the same |
JPS5397988A (en) | 1977-02-08 | 1978-08-26 | Toyo Soda Mfg Co Ltd | Production of cation exchange membrane |
FR2387260A1 (fr) | 1977-04-12 | 1978-11-10 | Rhone Poulenc Ind | Membranes echangeuses d'ions |
JPS53134088A (en) | 1977-04-28 | 1978-11-22 | Asahi Glass Co Ltd | Production of fluorocopolymer having ion exchange groups and its crosslinked article |
US4230549A (en) * | 1977-05-31 | 1980-10-28 | Rai Research Corporation | Separator membranes for electrochemical cells |
JPS53149881A (en) * | 1977-06-03 | 1978-12-27 | Asahi Glass Co Ltd | Strengthened cation exchange resin membrane and production thereof |
DE2964904D1 (en) * | 1978-09-05 | 1983-03-31 | Ici Plc | Sulphonated polyarylethersulphone copolymers and process for the manufacture thereof |
US4281092A (en) * | 1978-11-30 | 1981-07-28 | E. I. Du Pont De Nemours And Company | Vulcanizable fluorinated copolymers |
US4242498A (en) * | 1979-04-09 | 1980-12-30 | Frosch Robert A | Process for the preparation of fluorine containing crosslinked elastomeric polytriazine and product so produced |
US4330654A (en) * | 1980-06-11 | 1982-05-18 | The Dow Chemical Company | Novel polymers having acid functionality |
US4470889A (en) * | 1980-06-11 | 1984-09-11 | The Dow Chemical Company | Electrolytic cell having an improved ion exchange membrane and process for operating |
DE3023455A1 (de) * | 1980-06-24 | 1982-01-14 | Hoechst Ag, 6000 Frankfurt | Verfahren zur fluorierung von polymeren und perfluorierte ionenaustauscher |
US4334082A (en) | 1980-09-26 | 1982-06-08 | E. I. Du Pont De Nemours And Company | Dialkyl perfluoro-ω-fluoroformyl diesters and monomers and polymers therefrom |
US4414159A (en) * | 1980-09-26 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Vinyl ether monomers and polymers therefrom |
ZA818207B (en) * | 1980-11-27 | 1982-10-27 | Ici Australia Ltd | Permselective membranes |
US4391844A (en) * | 1981-06-26 | 1983-07-05 | Diamond Shamrock Corporation | Method for making linings and coatings from soluble cross-linkable perfluorocarbon copolymers |
US4454247A (en) * | 1981-12-14 | 1984-06-12 | E. I. Du Pont De Nemours & Company | Ion exchange membranes |
US4440917A (en) * | 1981-12-14 | 1984-04-03 | E. I. Du Pont De Nemours & Company | Vinyl ethers monomers and polymers therefrom |
WO1986000624A1 (fr) * | 1984-07-13 | 1986-01-30 | Societe Atochem | Nouveau polymere fluore ionique, son procede de preparation et les membranes d'electrolyse formees a partir de ce polymere |
JPH0641494B2 (ja) * | 1984-08-31 | 1994-06-01 | 旭化成工業株式会社 | 架橋可能な含フツ素共重合体 |
US4686024A (en) * | 1985-02-01 | 1987-08-11 | The Green Cross Corporation | Novel perfluoro chemicals and polyfluorinated compounds and process for production of the same |
US4743419A (en) * | 1985-03-04 | 1988-05-10 | The Dow Chemical Company | On-line film fluorination method |
US4755567A (en) * | 1985-11-08 | 1988-07-05 | Exfluor Research Corporation | Perfluorination of ethers in the presence of hydrogen fluoride scavengers |
JP2750594B2 (ja) | 1989-02-01 | 1998-05-13 | 旭化成工業株式会社 | 高分子量ポリイミドイルアミジンとその製造法および用途 |
US5693748A (en) * | 1989-02-01 | 1997-12-02 | Asahi Kasei Kogyo Kabushiki Kaisha | High molecular weight polyimidoylamidine and a polytriazine derived therefrom |
US5986012A (en) * | 1989-04-24 | 1999-11-16 | E. I. Du Pont De Nemours And Company | Fluorination of radiation crosslinked perfluoroelastomers |
US5260351A (en) * | 1989-04-24 | 1993-11-09 | E. I. Du Pont De Nemours And Company | Radiation curing of perfluoroelastomers |
IT1235545B (it) | 1989-07-10 | 1992-09-09 | Ausimont Srl | Fluoroelastomeri dotati di migliore processabilita' e procedimento di preparazione |
US5852148A (en) * | 1991-07-10 | 1998-12-22 | Minnesota Mining & Manufacturing Company | Perfluoroalkyl halides and derivatives |
US6048952A (en) | 1991-07-10 | 2000-04-11 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
US5264508A (en) * | 1992-06-25 | 1993-11-23 | The Dow Chemical Company | Polymers of haloperfluoro and perfluoro ethers |
US5330626A (en) * | 1993-02-16 | 1994-07-19 | E. I. Du Pont De Nemours And Company | Irradiation of polymeric ion exchange membranes to increase water absorption |
WO1995010541A1 (fr) * | 1993-10-12 | 1995-04-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Copolymere de perfluorocarbone ayant des groupes fonctionnels et procede pour sa production |
US5466930A (en) * | 1994-02-23 | 1995-11-14 | Florida State University | Solid scintillators for detecting radioactive ions in solution |
US5447993A (en) * | 1994-04-19 | 1995-09-05 | E. I. Du Pont De Nemours And Company | Perfluoroelastomer curing |
JP3298321B2 (ja) * | 1994-08-31 | 2002-07-02 | ダイキン工業株式会社 | ビニリデンフルオライド系共重合体水性分散液、ビニリデンフルオライド系シード重合体水性分散液およびそれらの製法 |
US6254978B1 (en) * | 1994-11-14 | 2001-07-03 | W. L. Gore & Associates, Inc. | Ultra-thin integral composite membrane |
USRE37307E1 (en) * | 1994-11-14 | 2001-08-07 | W. L. Gore & Associates, Inc. | Ultra-thin integral composite membrane |
USRE37701E1 (en) * | 1994-11-14 | 2002-05-14 | W. L. Gore & Associates, Inc. | Integral composite membrane |
US5547551A (en) * | 1995-03-15 | 1996-08-20 | W. L. Gore & Associates, Inc. | Ultra-thin integral composite membrane |
US5795496A (en) * | 1995-11-22 | 1998-08-18 | California Institute Of Technology | Polymer material for electrolytic membranes in fuel cells |
DE19622337C1 (de) * | 1996-06-04 | 1998-03-12 | Dlr Deutsche Forschungsanstalt | Vernetzung von modifizierten Engineering Thermoplasten |
US5798417A (en) * | 1996-10-15 | 1998-08-25 | E. I. Du Pont De Nemours And Company | (Fluorovinyl ether)-grafted high-surface-area polyolefins and preparation thereof |
US5747546A (en) * | 1996-12-31 | 1998-05-05 | The Dow Chemical Company | Ion-exchange polymers having an expanded microstructure |
DE69835366T2 (de) * | 1997-03-31 | 2007-07-19 | Daikin Industries, Ltd. | Verfahren zur herstellung von perfluorvinylethersulfonsäure-derivaten |
WO1999005126A1 (fr) * | 1997-07-25 | 1999-02-04 | Acep Inc. | Composes ioniques perfluorovinyliques et leur utilisation dans des materiaux conducteurs |
US6248469B1 (en) * | 1997-08-29 | 2001-06-19 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
JPH11111310A (ja) * | 1997-09-30 | 1999-04-23 | Aisin Seiki Co Ltd | 燃料電池用の固体高分子電解質膜およびその製造方法 |
DE19854728B4 (de) * | 1997-11-27 | 2006-04-27 | Aisin Seiki K.K., Kariya | Polymerelektrolyt-Brennstoffzelle |
US6462228B1 (en) * | 1997-12-22 | 2002-10-08 | 3M Innovative Properties Company | Process for preparation of fluorinated sulfinates |
JPH11204121A (ja) * | 1998-01-19 | 1999-07-30 | Aisin Seiki Co Ltd | 固体高分子電解質型燃料電池 |
DE69940033D1 (de) * | 1998-01-30 | 2009-01-15 | Hydro Quebec | Verfahren zur Herstellung von vernetzten sulfonierten Polymeren |
KR20010041541A (ko) * | 1998-03-03 | 2001-05-25 | 메리 이. 보울러 | 실질적으로 플루오르화된 이오노머 |
JP4150867B2 (ja) | 1998-05-13 | 2008-09-17 | ダイキン工業株式会社 | 燃料電池に使用するのに適した固体高分子電解質用材料 |
US6090895A (en) * | 1998-05-22 | 2000-07-18 | 3M Innovative Properties Co., | Crosslinked ion conductive membranes |
JP2002517537A (ja) * | 1998-05-29 | 2002-06-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 染色できるフルオロ重合体の繊維及びフィルム |
CN1318075A (zh) * | 1998-09-15 | 2001-10-17 | 国际电力有限公司 | 水基接枝 |
US6385769B1 (en) * | 1999-02-03 | 2002-05-07 | International Business Machines Corporation | Text based object oriented program code with a visual program builder and parser support for predetermined and not predetermined formats |
US6255370B1 (en) * | 1999-04-29 | 2001-07-03 | Railroad-Solutions, Llc | Rail spike retention and tie preservation mixture and method |
US6277512B1 (en) * | 1999-06-18 | 2001-08-21 | 3M Innovative Properties Company | Polymer electrolyte membranes from mixed dispersions |
JP4539896B2 (ja) | 1999-09-17 | 2010-09-08 | 独立行政法人産業技術総合研究所 | プロトン伝導性膜、その製造方法及びそれを用いた燃料電池 |
US6423784B1 (en) * | 1999-12-15 | 2002-07-23 | 3M Innovative Properties Company | Acid functional fluoropolymer membranes and method of manufacture |
JP4352546B2 (ja) * | 1999-12-22 | 2009-10-28 | ユニマテック株式会社 | フルオロエラストマー、その製造方法、架橋性組成物およびその硬化物 |
US6780935B2 (en) * | 2000-02-15 | 2004-08-24 | Atofina Chemicals, Inc. | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
DE10021104A1 (de) | 2000-05-02 | 2001-11-08 | Univ Stuttgart | Organisch-anorganische Membranen |
US6982303B2 (en) * | 2000-05-19 | 2006-01-03 | Jochen Kerres | Covalently cross-linked polymers and polymer membranes via sulfinate alkylation |
DE10024576A1 (de) * | 2000-05-19 | 2001-11-22 | Univ Stuttgart | Kovalent und ionisch vernetzte Polymere und Polymermembranen |
CA2312194A1 (fr) * | 2000-06-13 | 2001-12-13 | Mario Boucher | Elastomeres reticulables fluores bromosulfones a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
IT1318593B1 (it) * | 2000-06-23 | 2003-08-27 | Ausimont Spa | Ionomeri fluorurati. |
IT1318669B1 (it) | 2000-08-08 | 2003-08-27 | Ausimont Spa | Ionomeri fluorurati solfonici. |
EP1359142A4 (en) | 2001-02-01 | 2007-06-13 | Asahi Chemical Ind | PERFLUOROVINYL ETHER MONOMER HAVING A SULFONAMIDE GROUP |
ITMI20010383A1 (it) | 2001-02-26 | 2002-08-26 | Ausimont Spa | Membrane idrofiliche porose |
US6503378B1 (en) * | 2001-04-23 | 2003-01-07 | Motorola, Inc. | Polymer electrolyte membrane and method of fabrication |
US7045571B2 (en) | 2001-05-21 | 2006-05-16 | 3M Innovative Properties Company | Emulsion polymerization of fluorinated monomers |
KR20040041695A (ko) * | 2001-10-15 | 2004-05-17 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 메탄올 투과율의 감소를 위하여 폴리아민이 흡수된, 연료전지용 고체 중합체 막 |
US6727386B2 (en) * | 2001-10-25 | 2004-04-27 | 3M Innovative Properties Company | Aromatic imide and aromatic methylidynetrissulfonyl compounds and method of making |
US6624328B1 (en) * | 2002-12-17 | 2003-09-23 | 3M Innovative Properties Company | Preparation of perfluorinated vinyl ethers having a sulfonyl fluoride end-group |
US7348088B2 (en) | 2002-12-19 | 2008-03-25 | 3M Innovative Properties Company | Polymer electrolyte membrane |
US7071271B2 (en) * | 2003-10-30 | 2006-07-04 | 3M Innovative Properties Company | Aqueous emulsion polymerization of functionalized fluoromonomers |
US7265162B2 (en) * | 2003-11-13 | 2007-09-04 | 3M Innovative Properties Company | Bromine, chlorine or iodine functional polymer electrolytes crosslinked by e-beam |
US7259208B2 (en) * | 2003-11-13 | 2007-08-21 | 3M Innovative Properties Company | Reinforced polymer electrolyte membrane |
US7074841B2 (en) * | 2003-11-13 | 2006-07-11 | Yandrasits Michael A | Polymer electrolyte membranes crosslinked by nitrile trimerization |
US7179847B2 (en) * | 2003-11-13 | 2007-02-20 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by e-beam |
US7060756B2 (en) * | 2003-11-24 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolyte with aromatic sulfone crosslinking |
US7112614B2 (en) * | 2003-12-08 | 2006-09-26 | 3M Innovative Properties Company | Crosslinked polymer |
US7060738B2 (en) * | 2003-12-11 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by ultraviolet radiation |
-
2003
- 2003-12-17 US US10/738,083 patent/US7173067B2/en not_active Expired - Fee Related
-
2004
- 2004-11-19 EP EP04811655A patent/EP1694718A1/en not_active Withdrawn
- 2004-11-19 CN CNB2004800398615A patent/CN100560612C/zh not_active Expired - Fee Related
- 2004-11-19 WO PCT/US2004/038966 patent/WO2005061559A1/en active Application Filing
- 2004-11-19 CA CA002550285A patent/CA2550285A1/en not_active Abandoned
- 2004-11-19 KR KR1020067014164A patent/KR20070008544A/ko not_active Application Discontinuation
- 2004-11-19 JP JP2006545669A patent/JP2007517095A/ja active Pending
- 2004-12-03 TW TW093137278A patent/TW200533687A/zh unknown
-
2007
- 2007-01-03 US US11/619,372 patent/US7326737B2/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4844360A (ja) * | 1971-09-08 | 1973-06-26 | ||
US3853828A (en) * | 1973-11-21 | 1974-12-10 | Us Army | Process for crosslinking fluorocarbon polymers |
JP2001283866A (ja) * | 2000-03-31 | 2001-10-12 | Japan Storage Battery Co Ltd | 燃料電池用ガス拡散電極およびその製造方法 |
JP2002324559A (ja) * | 2001-02-23 | 2002-11-08 | Toyota Central Res & Dev Lab Inc | 多官能化電解質及びこれを用いた電気化学デバイス並びに多官能化電解質の製造方法 |
JP2003346815A (ja) * | 2002-05-30 | 2003-12-05 | Toyota Central Res & Dev Lab Inc | 膜電極接合体、及びその製造方法 |
WO2004066426A1 (ja) * | 2003-01-20 | 2004-08-05 | Asahi Glass Company, Limited | 固体高分子型燃料電池用電解質材料の製造方法及び固体高分子型燃料電池用膜電極接合体 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104448369A (zh) * | 2014-11-14 | 2015-03-25 | 南京理工大学 | 一类接枝全交联型质子交换膜及其制备方法 |
Also Published As
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US20050137351A1 (en) | 2005-06-23 |
CN1902235A (zh) | 2007-01-24 |
US20070105966A1 (en) | 2007-05-10 |
TW200533687A (en) | 2005-10-16 |
US7326737B2 (en) | 2008-02-05 |
CN100560612C (zh) | 2009-11-18 |
US7173067B2 (en) | 2007-02-06 |
WO2005061559A1 (en) | 2005-07-07 |
EP1694718A1 (en) | 2006-08-30 |
CA2550285A1 (en) | 2005-07-07 |
KR20070008544A (ko) | 2007-01-17 |
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