JP2007523066A5 - - Google Patents
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- Publication number
- JP2007523066A5 JP2007523066A5 JP2006551531A JP2006551531A JP2007523066A5 JP 2007523066 A5 JP2007523066 A5 JP 2007523066A5 JP 2006551531 A JP2006551531 A JP 2006551531A JP 2006551531 A JP2006551531 A JP 2006551531A JP 2007523066 A5 JP2007523066 A5 JP 2007523066A5
- Authority
- JP
- Japan
- Prior art keywords
- nitrogen
- polymer
- group
- membrane
- triazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 26
- 239000012528 membrane Substances 0.000 claims description 23
- 239000002131 composite material Substances 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 17
- 229920001940 conductive polymer Polymers 0.000 claims description 17
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 16
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 16
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002322 conducting polymer Substances 0.000 claims description 11
- 150000003852 triazoles Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 239000000446 fuel Substances 0.000 claims description 4
- 239000005518 polymer electrolyte Substances 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- -1 inorganic acid compound Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 210000003850 cellular structure Anatomy 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 238000002047 photoemission electron microscopy Methods 0.000 description 4
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53964104P | 2004-01-27 | 2004-01-27 | |
| US60/539,641 | 2004-01-27 | ||
| US61481404P | 2004-09-30 | 2004-09-30 | |
| US60/614,814 | 2004-09-30 | ||
| US11/044,527 US7576165B2 (en) | 2004-01-27 | 2005-01-26 | Heterocycle grafted monomers and related polymers and hybrid inorganic-organic polymer membranes |
| US11/044,527 | 2005-01-26 | ||
| PCT/US2005/002922 WO2005072413A2 (en) | 2004-01-27 | 2005-01-27 | Heterocycle grafted monomers and related polymers and hybrid inorganic-organic polymer membranes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007523066A JP2007523066A (ja) | 2007-08-16 |
| JP2007523066A5 true JP2007523066A5 (enExample) | 2008-03-13 |
| JP5171042B2 JP5171042B2 (ja) | 2013-03-27 |
Family
ID=34831063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551531A Expired - Fee Related JP5171042B2 (ja) | 2004-01-27 | 2005-01-27 | ポリマー電解質膜及びそれを含む燃料電池 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7576165B2 (enExample) |
| EP (1) | EP1713794B1 (enExample) |
| JP (1) | JP5171042B2 (enExample) |
| CN (1) | CN1926131B (enExample) |
| WO (1) | WO2005072413A2 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060083976A1 (en) * | 2004-06-09 | 2006-04-20 | California Institute Of Technology | Substituted nitrogen heterocycles as proton carriers for water-free proton exchange membranes for fuel cells |
| US7208243B2 (en) * | 2004-12-01 | 2007-04-24 | Toyota Technical Center Usa, Inc. | Proton exchange membranes using cycloaddition reaction between azide and alkyne containing components |
| KR100967295B1 (ko) * | 2005-07-15 | 2010-07-01 | 제이에스알 가부시끼가이샤 | 고체 고분자형 연료 전지용 전극 전해질 |
| US20070066762A1 (en) * | 2005-09-22 | 2007-03-22 | Acosta Erick J | Triazole-containing fluorinated polymers |
| WO2008048317A1 (en) | 2005-12-22 | 2008-04-24 | Ballard Power Systems Inc. | Water insoluble additive for improving conductivity of an ion exchange membrane |
| US7964651B2 (en) * | 2006-12-21 | 2011-06-21 | Toyota Motor Engineering & Manufacturing North America, Inc. | Sulfonyl grafted heterocycle materials for proton conducting electrolytes |
| FR2921517B1 (fr) * | 2007-09-26 | 2010-12-03 | Commissariat Energie Atomique | Membranes conductrices de protons pour pile a combustible presentant un gradient de protons et procedes de preparation desdites membranes |
| CN102066468B (zh) | 2008-04-24 | 2015-01-28 | 3M创新有限公司 | 质子传导材料 |
| US7947410B2 (en) * | 2008-08-22 | 2011-05-24 | Toyota Motor Engineering & Manufacturing North America, Inc. | Fuel cell electrodes with triazole modified polymers and membrane electrode assemblies incorporating same |
| WO2010104837A1 (en) | 2009-03-11 | 2010-09-16 | Isp Investments Inc. | Functionalized 4-and 5-vinyl substituted regioisomers of 1,2,3-triazoles via 1,3-dipolar cycloaddition and polymers thereof |
| WO2011005806A1 (en) * | 2009-07-08 | 2011-01-13 | Isp Investments Inc. | 4- and 5 substituted 1,2,3- triazole moieties with at least one remote polymerizable moiety and polymers thereof |
| US20110045381A1 (en) * | 2009-08-18 | 2011-02-24 | Gm Global Technology Operations, Inc. | Hydrocarbon PEM Membranes with Perfluorosulfonic Acid Groups for Automotive Fuel Cells |
| US9101886B2 (en) | 2009-11-10 | 2015-08-11 | Daimler Ag | Composite proton conducting membrane with low degradation and membrane electrode assembly for fuel cells |
| US20110111321A1 (en) * | 2009-11-10 | 2011-05-12 | Daimler Ag | Composite proton conducting membrane with low degradation and membrane electrode assembly for fuel cells |
| US8519074B2 (en) * | 2010-01-15 | 2013-08-27 | The University of Massachusettes | Comb polymers for supramolecular nanoconfinement |
| KR101767370B1 (ko) | 2011-07-29 | 2017-08-24 | 코오롱인더스트리 주식회사 | 연료전지용 고분자 전해질막 및 그 제조방법 |
| FR2992650B1 (fr) * | 2012-06-29 | 2014-08-08 | Peugeot Citroen Automobiles Sa | Procede de synthese de polymeres et leur utilisation pour realiser des membranes pour piles a combustible fonctionnant a faible humidite relative |
| CN103396551B (zh) * | 2012-09-14 | 2015-09-30 | 深圳市泰康新材料科技有限公司 | 一种咪唑基改性硅油及其制备与应用 |
| CN102945975A (zh) * | 2012-12-10 | 2013-02-27 | 厦门大学 | 吡啶鎓盐聚合物阴离子交换膜及其制备方法 |
| CN103346341A (zh) * | 2013-06-08 | 2013-10-09 | 上海大学 | 酸碱复合型高温质子交换膜及其制备方法 |
| CN103755650B (zh) * | 2013-10-24 | 2016-03-30 | 上海大学 | 三唑官能化的4,4’-二氟二苯砜类化合物及其合成方法 |
| CN108779275B (zh) * | 2016-02-03 | 2024-10-15 | 坎麦克斯动力有限责任公司 | 双极性离聚物膜 |
| US10950882B2 (en) | 2018-02-05 | 2021-03-16 | Toyota Jidosha Kabushiki Kaisha | Proton-conductive membrane and fuel cell |
| CN108417870B (zh) * | 2018-03-13 | 2021-03-23 | 中国科学院上海有机化学研究所 | 一种有机高温质子交换膜及其制备方法 |
| CN108777314B (zh) * | 2018-05-29 | 2020-08-07 | 中国科学院上海有机化学研究所 | 一种复合型有机膦酸高温质子交换膜及其制备方法 |
| CN108767298B (zh) * | 2018-05-29 | 2020-10-30 | 中国科学院上海有机化学研究所 | 一种有机高分子交联的有机膦酸高温质子交换膜及其制备方法 |
| CN108384170B (zh) * | 2018-05-29 | 2020-03-10 | 中国科学院上海有机化学研究所 | 一种交联型有机膦酸高温质子交换膜及其制备方法 |
| CN108598532B (zh) * | 2018-05-29 | 2020-08-07 | 中国科学院上海有机化学研究所 | 一种燃料电池用有机膦酸高温质子交换膜及其制备方法 |
| CN108666603B (zh) * | 2018-05-29 | 2020-03-10 | 中国科学院上海有机化学研究所 | 一种有机膦酸高温质子交换膜及其制备方法 |
| JP7103912B2 (ja) * | 2018-10-24 | 2022-07-20 | トヨタ自動車株式会社 | 橋架け構造を有するプロトン伝導膜及び燃料電池 |
| AU2020391106B2 (en) * | 2019-11-26 | 2024-03-21 | Gilead Sciences, Inc. | Processes and intermediates for preparing MCL1 inhibitors |
| US20240343696A1 (en) * | 2021-07-05 | 2024-10-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Compounds and uses thereof in the treatment and prevention of diseases and conditions associate with or aggravated by impaired mitophagy or oxidative stress |
| JP7636291B2 (ja) | 2021-08-04 | 2025-02-26 | トヨタ自動車株式会社 | プロトン伝導材料 |
| US12278363B1 (en) | 2024-04-29 | 2025-04-15 | Camx Power, Llc | Multiple morphology composite cathode materials providing high energy and long cycle life and cells employing the same |
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| US3122581A (en) | 1961-10-27 | 1964-02-25 | Union Carbide Corp | Preparation of phosphorus-containing organosilicon compounds |
| US3408420A (en) | 1964-04-30 | 1968-10-29 | Du Pont | Silane-modified olefinic copolymers |
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| FR2601017B1 (fr) | 1986-07-02 | 1988-09-23 | Centre Nat Rech Scient | Nouvelles compositions a base de derives de silice modifiee par des groupements organiques, leur preparation et leur application, notamment comme conducteurs protoniques |
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| EP0532408A1 (fr) | 1991-09-13 | 1993-03-17 | Saint-Gobain Vitrage International | Polymère conducteur protonique, application en tant qu'électrolyte dans des dispositifs électrochimiques |
| CH691209A5 (de) | 1993-09-06 | 2001-05-15 | Scherrer Inst Paul | Herstellungsverfahren für einen Polmerelektrolyten und elektrochemische Zelle mit diesem Polymerelektrolyten. |
| US5389726A (en) | 1994-05-05 | 1995-02-14 | Dow Corning Corporation | Nail lacquer primary film forming resin |
| DE19500253A1 (de) | 1995-01-05 | 1996-07-11 | Wacker Chemie Gmbh | Phosphorhaltige Organosiliciumverbindungen |
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| US6201064B1 (en) | 1997-11-06 | 2001-03-13 | Kaneka Corporation | Crosslinked rubber particles, graft copolymer particles and thermoplastic resin composition |
| US6096899A (en) | 1998-04-14 | 2000-08-01 | The Regents Of The University Of Michigan | Cylic imidazole compounds having relatively low hydrogen content and relatively high nitrogen content and polymers formed therefrom |
| US6124060A (en) | 1998-05-20 | 2000-09-26 | Honda Giken Kogyo Kabushiki Kaisha | Solid polymer electrolytes |
| US6310110B1 (en) | 1999-07-30 | 2001-10-30 | Michael A. Markowitz | Molecularly-imprinted material made by template-directed synthesis |
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| DE60020592T2 (de) | 1999-11-08 | 2006-05-04 | E.I. Du Pont De Nemours And Co., Wilmington | Feuchtigkeitshärtende schmelzverarbeitbare ethylenpfropfcopolymere |
| US6423784B1 (en) | 1999-12-15 | 2002-07-23 | 3M Innovative Properties Company | Acid functional fluoropolymer membranes and method of manufacture |
| JP2001199961A (ja) | 2000-01-21 | 2001-07-24 | Fuji Photo Film Co Ltd | 重合性溶融塩モノマー、電解質組成物および電気化学電池 |
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| DE10021106A1 (de) * | 2000-05-02 | 2001-11-08 | Univ Stuttgart | Polymere Membranen |
| DE10021104A1 (de) | 2000-05-02 | 2001-11-08 | Univ Stuttgart | Organisch-anorganische Membranen |
| JP3513097B2 (ja) * | 2000-09-29 | 2004-03-31 | 株式会社東芝 | プロトン伝導性膜およびそれを用いた燃料電池 |
| US20020127474A1 (en) | 2001-01-09 | 2002-09-12 | E.C.R.-Electro-Chemical Research Ltd. | Proton-selective conducting membranes |
| WO2002088222A1 (de) | 2001-03-13 | 2002-11-07 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Phosphorhaltige, organisch polymerisierbare silane und damit hergestellte kieselsäure-polykondensate |
| US6713643B2 (en) | 2001-05-24 | 2004-03-30 | Board Of Trustees Of Michigan State University | Ultrastable organofunctional microporous to mesoporous silica compositions |
| US6756436B2 (en) | 2001-06-26 | 2004-06-29 | Acushnet Company | Golf balls comprising highly-neutralized acid polymers |
| JP4004769B2 (ja) * | 2001-10-17 | 2007-11-07 | Ｎｅｃトーキン株式会社 | 電解液、並びにこれを用いた電気化学セル |
| DE10163518A1 (de) | 2001-12-21 | 2003-07-10 | Fraunhofer Ges Forschung | Protonenleitfähige Membranen/Schichten und Verfahren zu deren Herstellung |
| US6716908B2 (en) | 2002-01-30 | 2004-04-06 | Dow Corning Corporation | Alkoxysilyl functional silicone based materials |
| ATE463847T1 (de) | 2002-02-06 | 2010-04-15 | Battelle Memorial Institute | Polymerelektrolytmembranen zur verwendung in brennstoffzellen |
| AU2003237581A1 (en) | 2002-07-04 | 2004-01-23 | Ben-Gurion University Of The Negev | Highly conductive ordered ion exchange membranes |
| JP3884340B2 (ja) | 2002-07-10 | 2007-02-21 | 本田技研工業株式会社 | プロトン伝導性高分子固体電解質 |
| WO2005001037A2 (en) | 2003-05-28 | 2005-01-06 | Toyota Technical Center, Usa, Inc. | Electrolyte membranes based on alkyloxysilane grafted thermoplastic polymers |
| US7851580B2 (en) | 2003-05-28 | 2010-12-14 | Toyota Motor Engineering & Manufacturing North America, Inc. | Polymer electrolyte membranes (PEMs) based on imidazole ring terminated flexible branches grafted on hybrid inorganic-organic polymers |
| US7183370B2 (en) | 2003-09-11 | 2007-02-27 | Toyota Technical Center Usa, Inc | Phosphonic-acid grafted hybrid inorganic-organic proton electrolyte membranes (PEMs) |
-
2005
- 2005-01-26 US US11/044,527 patent/US7576165B2/en not_active Expired - Lifetime
- 2005-01-27 CN CN2005800064394A patent/CN1926131B/zh not_active Expired - Fee Related
- 2005-01-27 JP JP2006551531A patent/JP5171042B2/ja not_active Expired - Fee Related
- 2005-01-27 EP EP05712383.8A patent/EP1713794B1/en not_active Ceased
- 2005-01-27 WO PCT/US2005/002922 patent/WO2005072413A2/en not_active Ceased
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