JP5208633B2 - リン含有ベンゾオキサジン系モノマー、リン含有ベンゾオキサジン系モノマーの重合体、燃料電池用電極、燃料電池用電解質膜および燃料電池 - Google Patents
リン含有ベンゾオキサジン系モノマー、リン含有ベンゾオキサジン系モノマーの重合体、燃料電池用電極、燃料電池用電解質膜および燃料電池 Download PDFInfo
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- JP5208633B2 JP5208633B2 JP2008233675A JP2008233675A JP5208633B2 JP 5208633 B2 JP5208633 B2 JP 5208633B2 JP 2008233675 A JP2008233675 A JP 2008233675A JP 2008233675 A JP2008233675 A JP 2008233675A JP 5208633 B2 JP5208633 B2 JP 5208633B2
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- fuel cell
- chemical formula
- phosphorus
- group
- containing benzoxazine
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- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- 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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- 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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- H01M8/1034—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having phosphorus, e.g. sulfonated polyphosphazenes [S-PPh]
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- 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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- 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
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Description
・・・(化学式8)
・・・(化学式9)
・・・(化学式10)
・・・(化学式13)
・・・(化学式8)
・・・(化学式9)
・・・(化学式10)
・・・(化学式13)
100mlの1口の丸底フラスコに、トリス(4−ヒドロキシフェニル)リン酸塩(3.0g、0.008mol)、ホルムアルデヒド(1.68g 0.053mol)及び3,4−ジフルオロアニリン(3.41g、0.026mol)を順に入れた後、90℃のオイルバスで混合を実施した。
100mlの1口の丸底フラスコに、ビス(4−ヒドロキシフェニル)フェニルリン酸塩(10g、0.028mol)、ホルムアルデヒド(3.88g、0.123mol)、そして、3−アミノピリジン(5.78g、0.061mol)を順に入れた後、90℃のオイルバスで混合を実施した。
100mlの1口の丸底フラスコに、トリス(4−ヒドロキシフェニル)リン酸塩(1.5g、0.004mol)、ホルムアルデヒド(0.84g、0.0265mol)、そして、2,4,6−トリフルオロアニリン(1.94g、0.013mol)を順に入れた後、90℃のオイルバスで混合を実施した。
100mlの1口の丸底フラスコに、4−ヒドロキシフェニルジフェニルリン酸塩(1.5g、0.004mol)、ホルムアルデヒド(0.305g、0.01mol)、そして、3,4−ジフルオロアニリン(0.62g、0.005mol)を順に入れた後、90℃のオイルバスで混合を実施した。
250mlの1口の丸底フラスコに、トリス(4−ヒドロキシフェニル)リン酸塩(10g、0.027mol)、ホルムアルデヒド(5.56g、0.176mol)、そして、アニリン(8.2g、0.088mol)を順に入れた後、90℃のオイルバスで混合を実施した。
100mlの1口の丸底フラスコに、ビス(4−ヒドロキシフェニル)フェニルリン酸塩(5g、0.014mol)、ホルムアルデヒド(1.94g、0.061mol)、そして、3−フルオロアニリン(3.45g、0.031mol)を順に入れた後、90℃のオイルバスで混合を実施した。
100mlの1口の丸底フラスコに、4−ヒドロキシフェニルジフェニルリン酸塩(5g、0.0146mol)、ホルムアルデヒド(1.012g、0.032mol)、そして、2−アミノピリジン(1.515g、0.016mol)を順に入れた後、90℃のオイルバスで混合を実施した。
化学式12で表示されるt−PPO−a 20gとポリベンズイミダゾール10.8g、及びジメチルアセトアミドを混合して、それを約220℃範囲で硬化反応を実施して化学式12のt−PPO−aの重合体を収得した。
化学式12で表示されるt−PPO−aの代わりに化学式14で表されるm−PPO−2Aを使用したことを除いては、合成例8と同じ方法によって実施して、m−PPO−2APとポリベンズイミダゾールとの重合体を得ることができた。
100mlの1口の丸底フラスコに、t−ブチルフェノール(15g、0.1mol)、ホルムアルデヒド(6.31g、0.21mol)、そして、アニリン(10.24g、0.11mol)を順に入れた後、90℃のオイルバスで混合を実施した。
攪拌容器にカーボンに50質量%PtCoが担持された触媒1g及び溶媒NMP 3gを付加し、それを、モルタルを利用して攪拌してスラリーを作った。前記スラリーに、前記合成例3によって得た10質量%の化学式8で表されるtPPO−34DFAのNMP溶液を付加して、化学式8の化合物0.025gになるように添加してさらに攪拌した。
カソードの製造時に化学式8で表されるtPPO−34DFAの代わりに、化学式9のdPPO−3APを使用したことを除いては、実施例1と同じ方法によって実施してカソード及びそれを利用した燃料電池を製造した。
カソード製造時に化学式8で表されるtPPO−34DFAの代わりに、化学式10で表されるtPPO−246TFAを使用したことを除いては、実施例1と同じ方法によって実施してカソード及びそれを利用した燃料電池を製造した。
カソード製造時に化学式8で表されるtPPO−34DFAの代わりに、化学式11で表されるm−PPO−34DFAを使用したことを除いては、実施例1と同じ方法によって実施してカソード及びそれを利用した燃料電池を製造した。
カソード製造時に化学式8で表されるtPPO−34DFAを付加しないことを除いては、実施例1と同じ方法によって実施してカソード及びそれを利用した燃料電池を製造した。
攪拌容器に、カーボンに50質量%のPtCoが担持された触媒1g及び溶媒NMP 3gを付加した。これを、モルタルを利用して攪拌し、スラリーを作った。前記スラリーに、前記合成例1によって得たtBuPh−4FAのNMP溶液を付加して、tBuPh−4FA 0.025gになるように添加してさらに攪拌した。
電解質膜の製造時、化学式13のt−PPO−aの代わりに化学式14のd−PPO−4FAを使用したことを除いては、実施例5と同じ方法によって実施して、燃料電池用電解質膜及び燃料電池を製作した。
電解質膜の製造時、化学式13のt−PPO−aの代わりに化学式15のm−PPO−2APを使用したことを除いては、実施例5と同じ方法によって実施して、燃料電池用電解質膜及び燃料電池を製作した。
電解質膜の製造時、化学式13のt−PPO−a代わりに化学式9のt−PPO−34DFAを使用したことを除いては、実施例5と同じ方法によって実施して、燃料電池用電解質膜及び燃料電池を製作した。
攪拌容器に、カーボンに50質量%PtCoが担持された触媒1g及び溶媒NMP 3gを付加した。これを、モルタルを利用して攪拌して、スラリーを作った。前記スラリーに、10質量%の化学式12で表されるt−PPO−aのNMP溶液を付加して、化学式12の化合物0.025gになるように添加してさらに攪拌した。
カソードの製造時、化学式12で表されるt−PPO−aを使用せず、電解質膜としてポリベンズイミダゾール(PBI)膜を使用したことを除いては、実施例9と同じ方法によって燃料電池を製作した。
Claims (20)
- 下記化学式2〜化学式4で表される化合物のうち選択された一つ以上であることを特徴とする、リン含有ベンゾオキサジン系モノマー。
前記化学式3において、R2は、C6〜C10アリール基、またはC6〜C10アリールオキシ基であり、
前記化学式4において、R4及びR5は、C6〜C10アリール基であり、
前記化学式2〜化学式4において、R3は、下記構造式群で表される置換基の中から選択される。
- 前記化学式3で表される化合物は、下記化学式5で表される化合物であることを特徴とする、請求項1に記載のリン含有ベンゾオキサジン系モノマー。
前記化学式5において、R3は、下記構造式群で表示される置換基の中から選択される。
- 前記化学式4で表される化合物は、下記化学式7で表される化合物であることを特徴とする、請求項1に記載のリン含有ベンゾオキサジン系モノマー。
ここで、前記化学式7において、R3は、下記構造式群で表される置換基の中から選択される。
- 前記モノマーは、下記化学式8〜化学式11、化学式13〜化学式14で表される化合物の中から選択された一つであることを特徴とする、請求項1に記載のリン含有ベンゾオキサジン系モノマー。
・・・(化学式8)
・・・(化学式9)
・・・(化学式10)
・・・(化学式13)
- 請求項1〜請求項4のうちいずれか1項に記載のリン含有ベンゾオキサジン系モノマーの重合反応生成物、または、請求項1〜請求項4のうちいずれか1項に記載のリン含有ベンゾオキサジン系モノマーと架橋性化合物との重合反応生成物であることを特徴とする、リン含有ベンゾオキサジン系モノマーの重合体。
- 前記架橋性化合物は、ポリベンズイミダゾール、ポリベンズイミダゾール・塩基複合体、ポリベンズチアゾール、ポリベンゾオキサゾール、ポリイミドからなる群から選択された一つ以上であることを特徴とする、請求項5に記載のリン含有ベンゾオキサジン系モノマーの重合体。
- 前記架橋性化合物の含有量は、前記化学式1のベンゾオキサジン系モノマー100質量部を基準として、5〜95質量部であることを特徴とする、請求項5に記載のリン含有ベンゾオキサジン系モノマーの重合体。
- 請求項5に記載のリン含有ベンゾオキサジン系モノマーの重合体を含む触媒層を備えることを特徴とする、燃料電池用電極。
- 前記触媒層は、触媒を含むことを特徴とする、請求項8に記載の燃料電池用電極。
- 前記リン含有ベンゾオキサジン系モノマーの重合体の含有量は、触媒100質量部を基準として、0.1〜65質量部であることを特徴とする、請求項9に記載の燃料電池用電極。
- 前記触媒は、
白金単独、
白金と、金、パラジウム、ロジウム、イリジウム、ルテニウム、スズ、モリブデン、コバルト、クロムからなる群から選択された一種以上の金属を含む白金合金、または、
白金と、金、パラジウム、ロジウム、イリジウム、ルテニウム、スズ、モリブデン、コバルト、クロムからなる群から選択された一種以上の金属の混合物
であることを特徴とする、請求項9に記載の燃料電池用電極。 - 前記触媒は、
触媒金属、または触媒金属と触媒金属とがカーボン系担体に担持された担持触媒であり、
前記触媒金属は、
白金単独、
白金と、金、パラジウム、ロジウム、イリジウム、ルテニウム、スズ、モリブデン、コバルト、クロムからなる群から選択された一種以上の金属を含む白金合金、または、
白金と、金、パラジウム、ロジウム、イリジウム、ルテニウム、スズ、モリブデン、コバルト、クロムからなる群から選択された一種以上の金属の混合物
であることを特徴とする、請求項10に記載の燃料電池用電極。 - 前記触媒層は、リン酸及びC1〜C20有機ホスホン酸の中から選択された一つ以上のプロトン伝導体をさらに含むことを特徴とする、請求項8に記載の燃料電池用電極。
- ポリ(フッ化ビニリデン)、ポリテトラフルオロエチレン、テトラフルオロエチレン−ヘキサフルオロエチレン共重合体、FEP(fluorinated ethylenepropylene)、スチレンブタジエンラバー、ポリウレタンからなる群から選択された一つ以上のバインダーがさらに含まれることを特徴とする、請求項8に記載の燃料電池用電極。
- 前記触媒層は、触媒及びバインダーをさらに含み、
前記バインダーは、ポリ(フッ化ビニリデン)、ポリテトラフルオロエチレン、テトラフルオロエチレン−ヘキサフルオロエチレン共重合体、FEP、スチレンブタジエンラバー、ポリウレタンからなる群から選択された一つ以上であり、
前記バインダーの含有量は、触媒100質量部を基準として、0.1〜50質量部であることを特徴とする、請求項8に記載の燃料電池用電極。 - 請求項5に記載のリン含有ベンゾオキサジン系モノマーの重合体を含む燃料電池用電解質膜。
- 前記電解質膜は、リン酸及びC1〜C20有機ホスホン酸のうち選択された一つ以上のプロトン伝導体をさらに含むことを特徴とする、請求項16に記載の燃料電池用電解質膜。
- カソードと、
アノードと、
前記カソードおよび前記アノードの間に介在された電解質膜と、
を備え、
前記カソード及びアノードの中から選択された一つ以上は、
請求項5に記載のリン含有ベンゾオキサジン系モノマーの重合体及び触媒を含む触媒層を備える電極であることを特徴とする、燃料電池。 - 前記電解質膜は、
下記化学式2〜化学式4で表される化合物のうち選択された一つ以上であるリン含有ベンゾオキサジン系モノマーの重合反応生成物、または下記化学式2〜化学式4で表される化合物のうち選択された一つ以上であるリン含有ベンゾオキサジン系モノマーと架橋性化合物との重合反応生成物であるリン含有ベンゾオキサジン系モノマーの重合体を含む電解質膜であることを特徴とする、請求項18に記載の燃料電池。
前記化学式3において、R2は、C6〜C10アリール基、またはC6〜C10アリールオキシ基であり、
前記化学式4において、R4及びR5は、C6〜C10アリール基であり、
前記化学式2〜化学式4において、R3は、下記構造式群で表される置換基の中から選択される。
- カソードと、
アノードと、
前記カソードおよび前記アノードの間に介在され、請求項16に記載の燃料電池用電解質膜を含むことを特徴とする、燃料電池。
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Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI342322B (en) * | 2007-03-28 | 2011-05-21 | Grand Tek Advance Material Science Co Ltd | Halogen-free flame retardant epoxy resin composition, prepreg, and copper clad laminate |
EP2058321B1 (en) * | 2007-11-02 | 2014-01-08 | Samsung Electronics Co., Ltd. | Phosphorous containing monomer, polymer thereof, electrode for fuel cell including the polymer, electrolyte membrane for fuel cell including the polymer, and fuel cell using the electrode |
EP2366729B1 (en) * | 2009-04-24 | 2015-01-07 | Samsung Electronics Co., Ltd. | Cross-linked polyazole, method of preparing the polyazole, electrode for fuel cell including the cross-linked polyazole, electrolyte membrane for fuel cell including the cross-linked polyazole, method of manufacturing the electrolyte membrane, and fuel cell including the cross-linked polyazole |
CN102668204B (zh) * | 2009-11-14 | 2015-09-09 | 巴斯夫欧洲公司 | 使含氮聚合物机械稳定的方法 |
US9112232B2 (en) | 2010-02-05 | 2015-08-18 | Samsung Electronics Co., Ltd. | Composition, polymer thereof, electrode and electrolyte membrane for fuel cell, and fuel cell including the same |
WO2011108861A2 (en) | 2010-03-03 | 2011-09-09 | Samsung Electronics Co., Ltd. | Composition, method of preparing the composition, electrode including the composition, and fuel cell including the electrode |
DE102011007295A1 (de) * | 2011-04-13 | 2012-10-18 | Varta Microbattery Gmbh | Metall-Luft-Knopfzellen und ihre Herstellung |
KR101910574B1 (ko) * | 2011-12-19 | 2019-01-04 | 삼성전자주식회사 | 조성물, 이로부터 형성된 복합체, 이를 이용한 연료전지용 전극과 연료전지용 전해질막, 그 제조방법 및 이를 채용한 연료전지 |
CN103044348B (zh) * | 2012-12-13 | 2014-12-17 | 山东大学 | 含磺酸基的苯并噁嗪树脂及其制备方法和应用 |
CN103435812B (zh) * | 2013-08-21 | 2015-08-19 | 广东生益科技股份有限公司 | 一种苯并噁嗪中间体及其制备方法 |
JP2015174872A (ja) * | 2014-03-13 | 2015-10-05 | 日立化成株式会社 | ビスフェノール系樹脂、電極、鉛蓄電池及びこれらの製造方法、並びに、樹脂組成物 |
JP2015183171A (ja) * | 2014-03-26 | 2015-10-22 | 日立化成株式会社 | フェノール系樹脂、電極、鉛蓄電池及びこれらの製造方法、並びに、樹脂組成物 |
CN109608974B (zh) * | 2018-10-26 | 2020-09-18 | 合肥科天水性科技有限责任公司 | 一种氟化水性聚氨酯及其制备方法和用途 |
Family Cites Families (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4828699A (en) | 1987-08-20 | 1989-05-09 | Hoechst Celanese Corporation | Process for the production of microporous polybenzimidazole articles |
US5098985A (en) | 1988-10-11 | 1992-03-24 | The Dow Chemical Company | Copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties |
US5250633A (en) | 1991-01-29 | 1993-10-05 | Hoechst Celanese Corp. | Fibers and fibrets from blends of polybezimidazoles and aromatic polyamides, aromatic polyamide-hydrazides or aromatic polyamides containing heterocyclic linkages |
JPH05283082A (ja) | 1992-04-02 | 1993-10-29 | Mitsubishi Heavy Ind Ltd | ガス拡散電極及びその製造方法 |
US5410012A (en) | 1993-03-05 | 1995-04-25 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Poly(N-arylenebenzimidazoles) via aromatic nucleophilic displacement |
US5412059A (en) | 1993-04-05 | 1995-05-02 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polybenzimidazoles via aromatic nucleophilic displacement |
US5525436A (en) | 1994-11-01 | 1996-06-11 | Case Western Reserve University | Proton conducting polymers used as membranes |
JPH1025343A (ja) | 1996-07-10 | 1998-01-27 | Sumitomo Durez Co Ltd | 熱硬化性樹脂組成物 |
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 |
US6042968A (en) | 1997-07-16 | 2000-03-28 | Aventis Research & Technologies Gmbh & Co. Kg | Process for producing polybenzimidazole fabrics for use in fuel |
JPH1197011A (ja) | 1997-09-17 | 1999-04-09 | Unitika Ltd | 非水リチウム二次電池 |
AU3704400A (en) | 1999-03-04 | 2000-09-21 | E.I. Du Pont De Nemours And Company | Fused bicyclic oxazinone and thiazinone fungicides |
JP2001019844A (ja) * | 1999-07-09 | 2001-01-23 | Asahi Chem Ind Co Ltd | 硬化性ポリフェニレンエーテル樹脂組成物 |
US6682842B1 (en) | 1999-07-31 | 2004-01-27 | The Regents Of The University Of California | Composite electrode/electrolyte structure |
WO2001034581A1 (en) | 1999-11-05 | 2001-05-17 | The Dow Chemical Company | High char yield benzoxazine compositions |
CN1229886C (zh) | 1999-12-06 | 2005-11-30 | 日立化成工业株式会社 | 燃料电池、燃料电池隔板及其制造方法 |
JP2001270891A (ja) * | 2000-03-24 | 2001-10-02 | Asahi Kasei Corp | ベンゾオキサジン環を有するリン酸エステル |
JP2001271070A (ja) * | 2000-03-27 | 2001-10-02 | Asahi Kasei Corp | 難燃剤 |
JP2001345106A (ja) * | 2000-03-31 | 2001-12-14 | Japan Storage Battery Co Ltd | 燃料電池用電極およびその製造方法 |
GB0016752D0 (en) | 2000-07-08 | 2000-08-30 | Johnson Matthey Plc | Electrochemical structure |
WO2002014334A1 (fr) | 2000-08-10 | 2002-02-21 | Nippon Kayaku Kabushiki Kaisha | Composes phenoles, compositions de resine et produits polymerises obtenus a partir de ces compositions de resine |
US6855674B2 (en) | 2000-12-22 | 2005-02-15 | Infineum International Ltd. | Hydroxy aromatic Mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions |
US20020127474A1 (en) | 2001-01-09 | 2002-09-12 | E.C.R.-Electro-Chemical Research Ltd. | Proton-selective conducting membranes |
CA2431426C (en) | 2001-01-22 | 2010-08-24 | Vantico Ag | Flame-proofing agents |
KR20030081400A (ko) | 2001-01-26 | 2003-10-17 | 도레이 가부시끼가이샤 | 고분자 전해질막 및 그의 제조 방법 및 그것을 이용한고체 고분자형 연료 전지 |
JP2002260682A (ja) | 2001-03-02 | 2002-09-13 | Nisshinbo Ind Inc | 燃料電池セパレータ用組成物、燃料電池セパレータ及びその製造方法並びに固体高分子型燃料電池 |
CA2379505A1 (en) | 2001-04-02 | 2002-10-02 | Hidenori Tanaka | Coating composition containing benzoxazine compound |
JP2003012747A (ja) | 2001-06-28 | 2003-01-15 | Nippon Steel Chem Co Ltd | アセチニル基含有硬化性樹脂 |
JP2003012924A (ja) | 2001-07-02 | 2003-01-15 | Nippon Steel Chem Co Ltd | 硬化性樹脂組成物 |
US6620905B1 (en) | 2002-02-23 | 2003-09-16 | National Starch And Chemical Investment Holding Corporation | Curable compositions containing benzoxazine |
JPWO2003079475A1 (ja) | 2002-03-20 | 2005-07-21 | 株式会社三昌化工 | 燃料電池用セパレータ、その製造方法および該燃料電池用セパレータを用いた燃料電池 |
JP2003286320A (ja) | 2002-03-28 | 2003-10-10 | Nippon Steel Chem Co Ltd | アリル基含有熱硬化性樹脂及び硬化物 |
JP2003297386A (ja) * | 2002-04-08 | 2003-10-17 | Nisshinbo Ind Inc | 燃料電池セパレータ及びその製造方法 |
US7125624B2 (en) * | 2002-04-08 | 2006-10-24 | Nisshinbo Industries, Inc. | Fuel cell separator and method of manufacture |
JP4228040B2 (ja) | 2002-05-08 | 2009-02-25 | 東洋紡績株式会社 | スルホン酸基および/またはホスホン酸基を有するポリベンザゾール系化合物、それを含む樹脂組成物、樹脂成形物、固体高分子電解質膜、固体電解質膜/電極触媒層複合体およびその複合体の製造方法 |
CA2485971A1 (en) | 2002-05-13 | 2004-05-21 | Polyfuel, Inc. | Ion conductive block copolymers |
JP2004043547A (ja) | 2002-07-09 | 2004-02-12 | Nippon Steel Chem Co Ltd | イミド構造を有する熱硬化性樹脂、その硬化物及び熱硬化性樹脂組成物 |
WO2004009708A1 (ja) | 2002-07-19 | 2004-01-29 | Nippon Steel Chemical Co., Ltd. | 硬化性樹脂組成物 |
US6987163B2 (en) | 2002-08-07 | 2006-01-17 | Research Foundation Of The State University Of New York | Modified polybenzimidazole (PBI) membranes for enhanced polymer electrochemical cells |
DE10242017B4 (de) | 2002-09-11 | 2006-12-21 | Schill + Seilacher Aktiengesellschaft | Härter für Epoxidharze, dessen Verwendung und damit gehärtetes Epoxidharz |
JP2004103494A (ja) | 2002-09-12 | 2004-04-02 | Sansho Kako:Kk | 燃料電池用セパレータ、その製造方法および該燃料電池用セパレータを用いた燃料電池 |
DE10246461A1 (de) | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran enthaltend Polyazolblends und deren Anwendung in Brennstoffzellen |
JP3928611B2 (ja) | 2002-10-08 | 2007-06-13 | 東洋紡績株式会社 | ポリアリーレンエーテル系化合物、それを含有する組成物、およびそれらの製造方法 |
WO2004036679A1 (ja) | 2002-10-17 | 2004-04-29 | Toyo Boseki Kabushiki Kaisha | 複合イオン交換膜 |
JP4145640B2 (ja) | 2002-11-28 | 2008-09-03 | 新日鐵化学株式会社 | プリント回路基板用耐熱接着フィルム及びその製造方法 |
JP4317005B2 (ja) | 2003-03-25 | 2009-08-19 | 富士フイルム株式会社 | シリカゲル組成物、プロトン交換膜電極膜複合体、及び燃料電池 |
US20040206953A1 (en) | 2003-04-16 | 2004-10-21 | Robert Morena | Hermetically sealed glass package and method of fabrication |
WO2004101509A2 (en) | 2003-05-06 | 2004-11-25 | Case Western Reserve University | Functionalized benzoxazines, polymers and copolymers thereof |
US7157509B2 (en) | 2003-06-27 | 2007-01-02 | Henkel Corporation | Curable compositions |
JP4834949B2 (ja) | 2003-07-24 | 2011-12-14 | 東レ株式会社 | 熱硬化性樹脂組成物およびそれを用いた電子部品 |
US20050042961A1 (en) | 2003-08-18 | 2005-02-24 | Henkel Loctite Corporation | Curable compositions for advanced processes, and products made therefrom |
KR100528345B1 (ko) | 2003-08-29 | 2005-11-15 | 삼성에스디아이 주식회사 | 고분자 나노 복합막 및 이를 채용한 연료 전지 |
JP4380272B2 (ja) | 2003-09-08 | 2009-12-09 | 住友ベークライト株式会社 | エポキシ樹脂組成物およびそれを用いた半導体装置 |
US20050130006A1 (en) | 2003-09-17 | 2005-06-16 | Asahi Kasei Kabushiki Kaisha | Membrane electrode assembly for polymer electrolyte fuel cell |
KR100570640B1 (ko) | 2003-10-22 | 2006-04-12 | 삼성에스디아이 주식회사 | 바이폴러 플레이트용 복합재료 |
KR100570745B1 (ko) | 2003-10-30 | 2006-04-12 | 삼성에스디아이 주식회사 | 폴리(2,5-벤즈이미다졸)의 제조방법 |
JP2005283082A (ja) | 2004-03-29 | 2005-10-13 | Shigeyuki Nakamura | 燃焼ガス乾燥処理方式 |
KR100542203B1 (ko) | 2004-06-30 | 2006-01-10 | 삼성에스디아이 주식회사 | 연료전지용 바인더 조성물, 막-전극 접합체 및 막-전극접합체의 제조방법 |
US20070238723A1 (en) | 2004-10-15 | 2007-10-11 | Goble Stephen D | Benzoxazinyl-amidocyclopentyl-heterocyclic modulators of chemokine receptors |
JP2006147165A (ja) | 2004-11-16 | 2006-06-08 | Samsung Sdi Co Ltd | 固体高分子電解質膜とこの製造方法およびこれを用いた燃料電池 |
JP5140907B2 (ja) | 2005-06-03 | 2013-02-13 | 東洋紡株式会社 | プロトン伝導性高分子膜およびその製造方法およびそれを用いた燃料電池 |
EP1889863A4 (en) | 2005-06-09 | 2010-03-17 | Toyo Boseki | SULFONIC ACID GROUP-MAIN POLYMER, METHOD OF MANUFACTURING THEREOF, RESIN COMPOSITION CONTAINING SUCH SULPHONIC ACID GROUP POLYMER, POLYMER ELECTROLYTE MEMBRANE, POLYMER ELECTROLYTE MEMBRANE / ELECTRODE ARRANGEMENT AND FUEL CELL |
KR100818253B1 (ko) | 2005-09-03 | 2008-04-01 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물, 이를 포함한 전해질막 및 이를채용한 연료전지 |
KR100818254B1 (ko) | 2005-09-03 | 2008-03-31 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물, 이를 포함한 전해질막 및 이를채용한 연료전지 |
EP1760110B1 (en) | 2005-09-03 | 2011-11-02 | Samsung SDI Co., Ltd. | Polybenzoxazine-based compound, electrolyte membrane including the same, and fuel cell employing the electrolyte membrane |
KR100754374B1 (ko) | 2006-02-07 | 2007-08-31 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물을 이용한 전해질막 및 그제조방법 |
JP4839889B2 (ja) | 2006-02-28 | 2011-12-21 | カシオ計算機株式会社 | 液晶表示装置 |
KR100818255B1 (ko) * | 2006-05-29 | 2008-04-02 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물, 이를 포함한 전해질막 및 이를채용한 연료전지 |
KR101386162B1 (ko) | 2006-07-21 | 2014-04-18 | 삼성에스디아이 주식회사 | 연료전지용 전극 및 이를 채용한 연료전지 |
TWI295288B (en) | 2006-08-17 | 2008-04-01 | Univ Nat Chunghsing | New route for the synthesis of benzoxazine |
KR100745741B1 (ko) | 2006-08-22 | 2007-08-02 | 삼성에스디아이 주식회사 | 연료전지용 막 전극 접합체 및 이를 채용한 연료전지 |
KR100829552B1 (ko) | 2006-11-22 | 2008-05-14 | 삼성에스디아이 주식회사 | 연료전지용 전극 첨가제, 이를 포함한 연료전지용 전극, 그제조방법 및 이를이용한 연료전지 |
KR100893523B1 (ko) * | 2006-12-15 | 2009-04-17 | 삼성에스디아이 주식회사 | 연료전지용 전극, 그 제조방법 및 이를 채용한 연료전지 |
KR100790854B1 (ko) | 2006-12-29 | 2008-01-03 | 삼성에스디아이 주식회사 | 고분자 전해질막 및 이를 구비한 연료전지 |
KR101537311B1 (ko) | 2007-11-02 | 2015-07-17 | 삼성전자주식회사 | 연료전지용 전해질막 및 이를 이용한 연료전지 |
EP2062891B1 (en) | 2007-11-06 | 2012-08-08 | Samsung Electronics Co., Ltd. | Benzoxazine-based monomer, polymer thereof, electrode for fuel cell including the polymer, electrolyte membrane for fuel cell including the polymer, and fuel cell using the electrode |
CN101220153B (zh) | 2007-12-11 | 2010-04-07 | 山东大学 | 二元酚型含磷高阻燃性苯并噁嗪树脂的制备方法 |
EP2366729B1 (en) | 2009-04-24 | 2015-01-07 | Samsung Electronics Co., Ltd. | Cross-linked polyazole, method of preparing the polyazole, electrode for fuel cell including the cross-linked polyazole, electrolyte membrane for fuel cell including the cross-linked polyazole, method of manufacturing the electrolyte membrane, and fuel cell including the cross-linked polyazole |
US20110189581A1 (en) | 2010-02-04 | 2011-08-04 | Samsung Electronics Co., Ltd. | Compound, cross-linked material thereof, double cross-linked polymer thereof, and electrolyte membrane, electrode for fuel cell and fuel cell including same |
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2008
- 2008-09-10 EP EP11186727.1A patent/EP2433947B1/en not_active Ceased
- 2008-09-10 EP EP08164096A patent/EP2036912B1/en not_active Ceased
- 2008-09-11 JP JP2008233675A patent/JP5208633B2/ja not_active Expired - Fee Related
- 2008-09-11 KR KR1020080089999A patent/KR101015503B1/ko active IP Right Grant
- 2008-09-11 US US12/208,492 patent/US8192892B2/en active Active
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2012
- 2012-05-23 US US13/478,893 patent/US9243012B2/en active Active
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US8192892B2 (en) | 2012-06-05 |
US20120264909A1 (en) | 2012-10-18 |
KR101015503B1 (ko) | 2011-02-22 |
EP2433947B1 (en) | 2014-05-07 |
JP2009068011A (ja) | 2009-04-02 |
US9243012B2 (en) | 2016-01-26 |
US20090068543A1 (en) | 2009-03-12 |
EP2036912A1 (en) | 2009-03-18 |
KR20090027182A (ko) | 2009-03-16 |
EP2433947A1 (en) | 2012-03-28 |
EP2036912B1 (en) | 2012-08-08 |
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