JP4347891B2 - ポリベンゾイミダゾール−ベンズアミド共重合体及びその製造方法、また前記共重合体から製造される電解質膜及びその製造方法 - Google Patents
ポリベンゾイミダゾール−ベンズアミド共重合体及びその製造方法、また前記共重合体から製造される電解質膜及びその製造方法 Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- 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]
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/12—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids with both amino and carboxylic groups aromatically bound
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- 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
- H01M8/1027—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
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- 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
- H01M8/1041—Polymer electrolyte composites, mixtures or blends
- H01M8/1046—Mixtures of at least one polymer and at least one additive
- H01M8/1048—Ion-conducting additives, e.g. ion-conducting particles, heteropolyacids, metal phosphate or polybenzimidazole with phosphoric acid
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- 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
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino carboxylic acids or of polyamines and polycarboxylic acids
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- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/06—Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
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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
- 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
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- Inorganic Chemistry (AREA)
- Composite Materials (AREA)
- Fuel Cell (AREA)
- Conductive Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
クィングペングリら、ケミストリーオブマテリアルズ(Chemistry of materials, ACS)、2003年、第15巻、p.4896‐4915 ウェインライトら、ジャーナルオブザエレクトロケミカルソサエティー(Journal of the Electrochemical. Society, ECS)、1995年、第142巻、L121 クィングペングリら、ソリッドステートイオン(Solid State Ionics, Elservier)、2004年、第168巻、177‐185。 アセンシオ外2名、ジャーナルオブポリマーサイエンス、2002年、 第40巻、p.3703‐3710 ジャーナルオブザエレクトロケミカルソサエティー(Journal of the Electrochemical. Society, ECS)、2004年、第151巻、p.A304‐ A310 キムヒョンジュン外7名、マクロモレキュラーラピッドコミュニケイションズ(Macromolecular Rapid Communications, Wiley)2004年、第25巻、p.894‐897
「ポリベンゾイミダゾール‐ベンズアミド[95‐5(単位:重量%)]共重合体の合成」
本実施例ではアミン基とカルボン酸基を同時に有するジアミノ安息香酸を用いてアミノ安息香酸と共重合させた。この場合使われるジアミノ安息香酸とアミノ安息香酸は再結晶によって精製した。蒸溜水100mLに5gのジアミノ安息香酸を入れて加熱し溶解させた。全部とけて溶液になった後に常温で徐々に冷やして茶色の針状の結晶を得た。アミノ安息香酸も同じ方法で精製した。このように精製された単量体を真空下で24時間乾燥させた後使用した。
「ポリベンゾイミダゾール‐ベンズアミド[90‐10(単位:重量%)]共重合体の合成」
アミノ安息香酸0.5gを使ったこと以外は実試例1と同一である。
「ポリベンゾイミダゾール‐ベンズアミド[77‐23(単位:重量%)]共重合体の合成」
アミノ安息香酸1.5gを使ったこと以外は実試例1と同一である。
「水素イオン伝導度の測定」
本発明で製造された電解質膜の水素イオン伝導度をZAHNER IM‐6インピーダンス分析機(impedance analyzer)を使って、1Hz‐1MHzの周波数(frequency)領域で0.001‐0.1mAのAC電流大きさ(current amplitude)範囲の定電流モード(galvanostatic mode)で常温から180℃まで無加湿状態において測定し、Nafion(登録商標)115の場合には加湿のない状態と100%の加湿条件とに分けて測定した。その結果を図1に示した。
「粘度の測定」
本発明で製造された電解質膜の粘度測定はウベローデ(Ubbelohde)粘度計を使って測定し、50mL体積のフラスコ中で、上で製造された電解質膜1gを98%の硫酸で溶かして0.2g/dLとした後、30℃の恒温槽の中で測定した。その結果を表1に示した。
「機械的強度の測定」
本発明で製造された電解質膜の機械的強度測定はLloyd LR‐ 10K ユニバーサルテスティング機器(universal testing machine)(UTM)で測定し、常温において、湿度25%の状態で、それぞれの電解質膜をASTM D638タイプ Vを満たすドッグ‐ボーン(dog-bone)形態のフィルムを製造してそれぞれ5回ずつ繰り返して測定した後、その引張強度の平均値を表1に示した。
「熱的安定性の測定(TGA)」
本発明で合成された電解質膜の熱的安定性(TGA)はTAインスツルメンツ熱重量分析器(TA instruments thermogravimetric analyzer)2050を使って、それぞれの電解質膜50mgを10℃/minで昇温させながら50℃から800℃まで測定した。その結果を図2に示した。
Claims (7)
- 200℃乃至250℃の温度及び窒素雰囲気下で精製されたジアミノ安息香酸をポリリン酸に溶解させた後、アミノ安息香酸を混合した後6時間以上撹拌して製造されることを特徴とする請求項1に記載のポリベンゾイミダゾール‐ベンズアミド共重合体の製造方法。
- 請求項1に記載の共重合体を、リン酸、硫酸またはポリリン酸でドーピングすることによって製造されることを特徴とする高分子電解質膜。
- 請求項1に記載の共重合体の重合直後、その重合溶液をガラス板またはステンレス板に載せ、50℃乃至150℃間のオーブンで1分乃至3日間保管してフィルム層を製造した後、フィルム内のポリリン酸を取り除き、リン酸、硫酸またはポリリン酸でドーピングすることによって製造されることを特徴とするポリベンゾイミダゾール‐ベンズアミド共重合体電解質膜の製造方法。
- 更に、フィルム内のポリリン酸を取り除く工程の前に、形成されたフィルムを常温以下の温度に急速冷却し(quenching)フィルムを固める段階を含むことを特徴とする請求項4に記載のポリベンゾイミダゾール‐ベンズアミド共重合体電解質膜の製造方法。
- 請求項3に記載の高分子電解質膜を用いることを特徴とする膜‐電極ユニット(MEA)。
- 請求項6に記載の膜‐電極ユニットを含んでなることを特徴とする燃料電池システム。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR20040102397A KR100738788B1 (ko) | 2004-12-07 | 2004-12-07 | 폴리벤즈이미다졸-벤즈아마이드 공중합체와 그의제조방법, 및 이로부터 제조된 전해질 막과 그의 제조방법 |
PCT/KR2005/003927 WO2006062301A1 (en) | 2004-12-07 | 2005-11-21 | Polybenzimidazole-benzamide copolymer, process for preparing the same, electrolyte membrane prepared therefrom and process for preparing the same |
Publications (2)
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JP2007511663A JP2007511663A (ja) | 2007-05-10 |
JP4347891B2 true JP4347891B2 (ja) | 2009-10-21 |
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JP2006546863A Active JP4347891B2 (ja) | 2004-12-07 | 2005-11-21 | ポリベンゾイミダゾール−ベンズアミド共重合体及びその製造方法、また前記共重合体から製造される電解質膜及びその製造方法 |
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US (1) | US7556876B2 (ja) |
EP (1) | EP1819751B1 (ja) |
JP (1) | JP4347891B2 (ja) |
KR (1) | KR100738788B1 (ja) |
CN (1) | CN1860155A (ja) |
AT (1) | ATE435254T1 (ja) |
CA (1) | CA2541367C (ja) |
DE (1) | DE602005015252D1 (ja) |
TW (1) | TWI316523B (ja) |
WO (1) | WO2006062301A1 (ja) |
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KR100738788B1 (ko) * | 2004-12-07 | 2007-07-12 | 주식회사 엘지화학 | 폴리벤즈이미다졸-벤즈아마이드 공중합체와 그의제조방법, 및 이로부터 제조된 전해질 막과 그의 제조방법 |
KR100819676B1 (ko) * | 2005-11-14 | 2008-04-03 | 주식회사 엘지화학 | 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 |
WO2015064908A1 (ko) | 2013-10-29 | 2015-05-07 | 연세대학교 산학협력단 | 연료전지용 고분자 전해질막, 이의 제조방법 및 이를 포함하는 연료전지 |
US10741568B2 (en) | 2018-10-16 | 2020-08-11 | Silicon Storage Technology, Inc. | Precision tuning for the programming of analog neural memory in a deep learning artificial neural network |
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BE788751A (fr) * | 1971-09-13 | 1973-01-02 | Teijin Ltd | Membranes polymeres permselectives |
US4394500A (en) * | 1981-08-07 | 1983-07-19 | E. I. Du Pont De Nemours And Company | Bead polymerization process for preparing polybenzimidazole |
BR9712247A (pt) * | 1996-10-01 | 1999-08-24 | Hoechst Ag | Processo par produzir filmes polim-ricos para uso como c-lulas de combust¡vel |
US5739344A (en) | 1996-12-06 | 1998-04-14 | The Dow Chemical Company | Preparation of an aminoarylaminoarazole |
US5945233A (en) * | 1997-07-16 | 1999-08-31 | Avents Research & Technologies Gmbh & Co. Kg | Process for producing polybenzimidazole pastes and gels for use in fuel cells |
US6124060A (en) | 1998-05-20 | 2000-09-26 | Honda Giken Kogyo Kabushiki Kaisha | Solid polymer electrolytes |
JP3833012B2 (ja) * | 1999-07-29 | 2006-10-11 | 信越化学工業株式会社 | エチレン性二重結合を有する単量体の重合体を製造する方法 |
US6478987B1 (en) * | 1999-09-20 | 2002-11-12 | Honda Giken Kogyo Kabushiki Kaisha | Proton conducting polymer, method for producing the same, solid polymer electrolyte and electrode |
KR100570745B1 (ko) | 2003-10-30 | 2006-04-12 | 삼성에스디아이 주식회사 | 폴리(2,5-벤즈이미다졸)의 제조방법 |
KR100738788B1 (ko) * | 2004-12-07 | 2007-07-12 | 주식회사 엘지화학 | 폴리벤즈이미다졸-벤즈아마이드 공중합체와 그의제조방법, 및 이로부터 제조된 전해질 막과 그의 제조방법 |
KR100819676B1 (ko) * | 2005-11-14 | 2008-04-03 | 주식회사 엘지화학 | 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 |
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- 2004-12-07 KR KR20040102397A patent/KR100738788B1/ko active IP Right Grant
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- 2005-11-03 TW TW094138561A patent/TWI316523B/zh active
- 2005-11-17 US US11/280,228 patent/US7556876B2/en active Active
- 2005-11-21 CN CNA2005800010708A patent/CN1860155A/zh active Pending
- 2005-11-21 WO PCT/KR2005/003927 patent/WO2006062301A1/en active Application Filing
- 2005-11-21 DE DE602005015252T patent/DE602005015252D1/de active Active
- 2005-11-21 EP EP05821010A patent/EP1819751B1/en active Active
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WO2006062301A1 (en) | 2006-06-15 |
EP1819751A1 (en) | 2007-08-22 |
EP1819751A4 (en) | 2008-07-02 |
TW200621855A (en) | 2006-07-01 |
CA2541367A1 (en) | 2006-06-07 |
US7556876B2 (en) | 2009-07-07 |
ATE435254T1 (de) | 2009-07-15 |
EP1819751B1 (en) | 2009-07-01 |
CN1860155A (zh) | 2006-11-08 |
KR100738788B1 (ko) | 2007-07-12 |
CA2541367C (en) | 2010-06-08 |
JP2007511663A (ja) | 2007-05-10 |
DE602005015252D1 (de) | 2009-08-13 |
KR20060063273A (ko) | 2006-06-12 |
US20060068259A1 (en) | 2006-03-30 |
TWI316523B (en) | 2009-11-01 |
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