JP5243067B2 - 導電性ポリマーの導電性向上方法 - Google Patents
導電性ポリマーの導電性向上方法 Download PDFInfo
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- 229920001940 conductive polymer Polymers 0.000 title claims description 125
- 238000000034 method Methods 0.000 title claims description 33
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 116
- 239000001569 carbon dioxide Substances 0.000 claims description 58
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000003960 organic solvent Substances 0.000 claims description 26
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 14
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 13
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 13
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229920000767 polyaniline Polymers 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000010419 fine particle Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 229920000144 PEDOT:PSS Polymers 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- -1 polyparaphenylene Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
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- H01G11/22—Electrodes
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Description
請求項1は、
耐圧容器内に、導電性ポリマーと水と前記導電性ポリマーに対する相溶性を有する有機溶剤と二酸化炭素とを収容し、前記二酸化炭素が超臨界状態となるように、前記耐圧容器内を加熱加圧することを特徴とする導電性ポリマーの導電性向上方法であり、
請求項2は、
前記導電性ポリマーが、ポリスチレンスルホン酸の水溶液中で3,4−エチレンジオキシチオフェンを重合することにより得られる生成物及び/又はポリアニリンである前記請求項1に記載の導電性ポリマーの導電性向上方法であり、
請求項3は、
前記有機溶剤が、ジメチルスルホキシド、ポリエチレングリコール、N−メチルピロリドン、及びN,N−ジメチルホルムアミドよりなる群から選択される少なくとも一種である前記請求項1又は2に記載の導電性ポリマーの導電性向上方法であり、
請求項4は、
前記加熱加圧が、7〜25MPaに加圧しつつ、85〜110℃に加熱し、その温度及び圧力を0.5〜4時間にわたって維持することである前記請求項1〜3のいずれか一項に記載の導電性ポリマーの導電性向上方法である。
図1に示すように、まず、内容積500mLの耐圧容器2内に、処理前の平均粒径が0.4μmである導電性ポリマー(商品名:Baytron P)1w/oの水ディスパーション液10mLと純水9gとDMSO 1.1gとを装入した。
実施例1で使用された導電性ポリマー(商品名:Baytron P)1w/o水ディスパーション液10mLとDMSO 1.1gとを混合して50〜100℃で乾燥し、その後、製膜操作を実施した。この導電性ポリマーの抵抗値を前記実施例1と同様にして測定したところ、104Ω/□であった。
実施例2においては、実施例1におけるDMSO 1.1gの代わりにNMP(N−メチルピロリドン)1.03gを用い、実施例3においては、実施例1におけるDMSO 1.1gの代わりにエチレングリコール1.11gを用いた外は前記実施例1と同様に実施した。
前記実施例1における導電性ポリマー(商品名:Baytron P)を導電性ポリマー(商品名:Baytron PHCV4)に代えた他は前記実施例1と同様にして実施した。
前記比較例1における導電性ポリマー(商品名:Baytron P)を導電性ポリマー(商品名:Baytron PHCV4)に代えた他は前記比較例1と同様にして実施した。
実施例5においては、実施例4におけるDMSO 1.1gの代わりにNMP(N−メチルピロリドン)1.03gを用い、実施例6においては、実施例4におけるDMSO 1.1gの代わりにエチレングリコール1.11gを用いた外は前記実施例1と同様に実施した。
実施例7〜9においては、実施例1における導電性ポリマー(商品名:Baytron P)1w/oの水ディスパーション液10mLの代わりにポリアニリン4〜8w/oの水ディスパーション液10mLを使用した外は前記実施例1〜3と同様に実施した。
2 耐圧容器
2A 攪拌器
3 二酸化炭素ボンベ
3A ポンプ
3B バルブ
4 水貯留タンク
4A ポンプ
4B バルブ
5 バルブ
6 第2耐圧容器
7 バルブ
8 コイル状反応器
Claims (4)
- 耐圧容器内に、導電性ポリマーと水と前記導電性ポリマーに対する相溶性を有する有機溶剤と二酸化炭素とを収容し、前記二酸化炭素が超臨界状態となるように、前記耐圧容器内を加熱加圧することを特徴とする導電性ポリマーの導電性向上方法。
- 前記導電性ポリマーが、ポリスチレンスルホン酸の水溶液中で3,4−エチレンジオキシチオフェンを重合することにより得られる生成物及び/又はポリアニリンである前記請求項1に記載の導電性ポリマーの導電性向上方法。
- 前記有機溶剤が、ジメチルスルホキシド、ポリエチレングリコール、N−メチルピロリドン、及びN,N−ジメチルホルムアミドよりなる群から選択される少なくとも一種である前記請求項1又は2に記載の導電性ポリマーの導電性向上方法。
- 前記加熱加圧が、7〜25MPaに加圧しつつ、85〜110℃に加熱し、その温度及び圧力を0.5〜4時間にわたって維持することである前記請求項1〜3のいずれか一項に記載の導電性ポリマーの導電性向上方法。
Priority Applications (5)
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JP2008060106A JP5243067B2 (ja) | 2008-03-10 | 2008-03-10 | 導電性ポリマーの導電性向上方法 |
RU2010141565/04A RU2462485C2 (ru) | 2008-03-10 | 2008-03-11 | Способ улучшения проводимости проводящего полимерного продукта |
US12/920,989 US8188212B2 (en) | 2008-03-10 | 2008-03-11 | Method of enhancing conductivity of conductive polymer product |
PCT/JP2008/000533 WO2009113125A1 (ja) | 2008-03-10 | 2008-03-11 | 導電性ポリマーの導電性向上方法 |
EP20080720419 EP2253656B1 (en) | 2008-03-10 | 2008-03-11 | Method of enhancing conductivity of conductive polymer |
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JP2008060106A JP5243067B2 (ja) | 2008-03-10 | 2008-03-10 | 導電性ポリマーの導電性向上方法 |
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JP2009215422A JP2009215422A (ja) | 2009-09-24 |
JP5243067B2 true JP5243067B2 (ja) | 2013-07-24 |
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US (1) | US8188212B2 (ja) |
EP (1) | EP2253656B1 (ja) |
JP (1) | JP5243067B2 (ja) |
RU (1) | RU2462485C2 (ja) |
WO (1) | WO2009113125A1 (ja) |
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WO2008155879A1 (ja) * | 2007-06-18 | 2008-12-24 | Akita University | 導電性高分子の被膜製造方法 |
JP5041606B2 (ja) * | 2009-10-02 | 2012-10-03 | 日機装株式会社 | リチウムイオン二次電池における改質微粉状正極物質の製造方法 |
JP5008153B2 (ja) * | 2009-10-26 | 2012-08-22 | 日機装株式会社 | リチウムイオン二次電池における改質微粉状正極物質の製造方法 |
JP5740925B2 (ja) * | 2010-11-15 | 2015-07-01 | ナガセケムテックス株式会社 | 導電性コーティング組成物及び積層体 |
CN104059432B (zh) * | 2013-03-20 | 2016-01-06 | 北京阿格蕾雅科技发展有限公司 | 透明碳纳米管高分子复合导电墨水及其制备方法 |
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US5855819A (en) | 1997-03-27 | 1999-01-05 | University Of North Carolina At Chapel Hill | Synthesis of conductive polymers in liquid and supercritical CO2 |
US6156235A (en) * | 1997-11-10 | 2000-12-05 | World Properties, Inc. | Conductive elastomeric foams by in-situ vapor phase polymerization of pyrroles |
US6890584B2 (en) | 2000-06-28 | 2005-05-10 | Agfa-Gevaert | Flexographic ink containing a polymer or copolymer of a 3,4-dialkoxythiophene |
JP4144778B2 (ja) * | 2001-11-06 | 2008-09-03 | 国立大学法人東京工業大学 | イオン伝導性高分子およびその製造方法ならびにその処理方法 |
DE60219197T2 (de) * | 2001-12-04 | 2008-01-03 | Agfa-Gevaert | Verfahren zur herstellung von lösungen oder dispersionen von polythiophenepolymeren |
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US7247230B2 (en) | 2003-08-08 | 2007-07-24 | Northeastern University | Electrochemical synthesis and processing of conducting polymers in supercritical media |
FI116626B (fi) | 2004-01-27 | 2006-01-13 | Valtion Teknillinen | Menetelmä johtavien polymeeripinnoitteiden saostamiseksi ylikriittisessä hiilidioksidissa |
US7338620B2 (en) | 2004-03-17 | 2008-03-04 | E.I. Du Pont De Nemours And Company | Water dispersible polydioxythiophenes with polymeric acid colloids and a water-miscible organic liquid |
JP2006111798A (ja) | 2004-10-18 | 2006-04-27 | Nikkiso Co Ltd | ポリマー微粒子創製方法、およびポリマー微粒子創製装置 |
US20080274275A1 (en) | 2004-11-29 | 2008-11-06 | Japan Science And Technology Agency | Method For Preparing Composite Fine Particles |
DE102005016727A1 (de) | 2005-04-11 | 2006-10-26 | H.C. Starck Gmbh | Elektrolytkondensatoren mit polymerer Außenschicht und Verfahren zu ihrer Herstellung |
DE102005043829A1 (de) | 2005-09-13 | 2007-04-05 | H.C. Starck Gmbh | Verfahren zur Herstellung von Elektrolytkondensatoren mit hoher Nennspannung |
WO2008155879A1 (ja) | 2007-06-18 | 2008-12-24 | Akita University | 導電性高分子の被膜製造方法 |
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2008
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EP2253656B1 (en) | 2014-05-14 |
EP2253656A1 (en) | 2010-11-24 |
RU2462485C2 (ru) | 2012-09-27 |
RU2010141565A (ru) | 2012-04-20 |
JP2009215422A (ja) | 2009-09-24 |
WO2009113125A1 (ja) | 2009-09-17 |
US8188212B2 (en) | 2012-05-29 |
EP2253656A4 (en) | 2011-09-28 |
US20110071265A1 (en) | 2011-03-24 |
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