JP2006137940A - 導電性重合体の製造方法 - Google Patents
導電性重合体の製造方法 Download PDFInfo
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- JP2006137940A JP2006137940A JP2005297407A JP2005297407A JP2006137940A JP 2006137940 A JP2006137940 A JP 2006137940A JP 2005297407 A JP2005297407 A JP 2005297407A JP 2005297407 A JP2005297407 A JP 2005297407A JP 2006137940 A JP2006137940 A JP 2006137940A
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- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 36
- 239000002322 conducting polymer Substances 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- 239000000178 monomer Substances 0.000 claims abstract description 49
- 239000004094 surface-active agent Substances 0.000 claims abstract description 28
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- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 8
- -1 sulfonic acid compound Chemical class 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 15
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
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- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001302 tertiary amino group Chemical group 0.000 claims description 12
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
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- 0 *c1c[n](*)cc1* Chemical compound *c1c[n](*)cc1* 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
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- 239000000470 constituent Substances 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- YWPOLRBWRRKLMW-UHFFFAOYSA-M sodium;naphthalene-2-sulfonate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 YWPOLRBWRRKLMW-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
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- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- AVBCFBRGFCGJKX-UHFFFAOYSA-N thieno[3,4-d][1,3]dioxole Chemical compound S1C=C2OCOC2=C1 AVBCFBRGFCGJKX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C08L101/00—Compositions of unspecified macromolecular compounds
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Abstract
【解決手段】重合性単量体、界面活性剤、溶媒及び酸化剤の存在下、重合性単量体濃度が0.20〜2.8mol/L、かつ界面活性剤のモル比が重合性単量体1molに対し0.8〜1.6molである初期条件で重合することを特徴とする導電性重合体の製造方法及びその方法で得られる導電性重合体。
【選択図】なし
Description
これらの中でも、高い電気電導度を有するπ共役系高分子材料は、加工性に難のある金属系材料、金属酸化物系材料に変わる材料として、帯電防止材料、有機EL表示素子の構成部材、さらには固体電解コンデンサの固体電解質として利用されつつある。
特に近年はパーソナルコンピューターの需要が増し、さらに高性能化する中で、より高周波での動作に対応する電子部品類が求められるようになっているなど、高性能を有する製品が求められている。
また、電場や磁場などを利用した電磁気的な手法によってπ共役系高分子の重合規則性を高め、電気伝導度を改善する手法が数多く提案されているが、一般に専用設備を必要とし、また工業的には生産性及びコストの課題を有している。
[2]重合性単量体が一般式(I)
[3]重合性単量体が一般式(II)
[4]重合性単量体が2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシンである〔3〕の導電性重合体の製造方法、
[5]重合性単量体が一般式(III)
[6]重合性単量体がピロールである〔5〕の導電性重合体の製造方法、
[7]界面活性剤が有機スルホン酸化合物である〔1〕の導電性重合体の製造方法、
[8]有機スルホン酸化合物がナフタレンスルホン酸ナトリウムまたはその誘導体である〔7〕の導電性重合体の製造方法、
[9]酸化剤が鉄塩である〔1〕の導電性重合体の製造方法、
[10]界面活性剤のモル比が、重合性単量体1molに対し0.9〜1.5molである〔1〕の導電性重合体の製造方法、
[11]酸化剤のモル比が、重合性単量体1molに対し0.05〜1.5molである〔1〕の導電性重合体の製造方法、
[12]〔1〕乃至〔11〕のいずれかの製造方法で得られる導電性重合体。
本発明は、重合性単量体、界面活性剤、溶媒及び酸化剤の存在下で、重合性単量体濃度が0.2〜2.8mol/L、かつ界面活性剤のモル比が重合性単量体1molに対し0.8〜1.6molである初期条件で重合することを特徴とする導電性重合体の製造方法である。
また、炭素数1〜10の直鎖状もしくは分岐状の飽和または不飽和のアルコキシ基の具体例としては、例えばメトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、ペントキシ基、ヘキシルオキシ基、オクチルオキシ基等が挙げられる。
また、炭素数1〜10の直鎖状もしくは分岐状の飽和または不飽和のアルキルエステル基の具体例としては、例えばメチルエステル基、エチルエステル基、プロピルエステル基、イソプロピルエステル基、ブチルエステル基、ペンチルエステル基、ヘキシルエステル基、オクチルエステル基等が挙げられる。
蒸留水4mLを反応容器に入れ、界面活性剤として2−ナフタレンスルホン酸ナトリウム(以下、2NaNSと略す。)0.44g(2.1mmol,0.35mol/L相当)を加え、次に重合性単量体として2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン(以下、HTDOと略す。)0.28g(2.0mmol,0.33mol/L相当)を加え、撹拌した。この溶液に、水2mLに、酸化剤として硫酸鉄(III)を0.28g(0.7mmol,0.12mol/L相当)加えた溶液を1時間かけて滴下し、反応を開始した。反応は温度20℃で15時間撹拌しながら行った。得られた黒色重合体をろ過し、ろ液のpHが7程度になるまで蒸留水で洗浄し、次にアセトンで2回洗浄後、温度40℃の条件で10時間、真空乾燥を行った。得られた重合体の質量は0.17gであった。次に成形器を用いて3t/cm2の圧力下、減圧しながら直径1.3cmの円盤状ペレットを作製した。このペレットをLoresta IP MCP-T250(三菱化学社製)を用いて表面抵抗を測定し、得られた表面抵抗の値に膜厚を乗じて電気伝導度に換算した値を表1に示す。
界面活性剤を0.55g(2.6mmol,0.44mol/L相当)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.17gであり、電気伝導度を測定した結果を表1に示す。
酸化剤を0.20g(0.5mmol,0.086mol/L相当)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.16gであり、電気伝導度を測定した結果を表1に示す。
酸化剤を0.40g(1.0mmol,0.17mol/L相当)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.19gであり、電気伝導度を測定した結果を表1に示す。
酸化剤を0.56g(1.4mmol,0.24mol/L相当)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.19gであり、電気伝導度を測定した結果を表1に示す。
重合性単量体としてピロール(以下、PYと略す。)0.13g(2.0mmol,0.33mol/L相当)を用い、重合温度を5℃にした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.22gであり、電気伝導度を測定した結果を表1に示す。
蒸留水8mLを反応容器に入れ、界面活性剤として2NaNS 0.43g(2.1mmol,0.17mol/L相当)加え、次に重合性単量体としてHTDO 0.25g(1.8mmol/L,0.15mol/L相当)加え、撹拌した。この溶液に、水4mLに、酸化剤として硫酸鉄(III)を0.26g(0.65mmol,0.055mol/L相当)加えた溶液を1時間かけて滴下し、反応を開始した。反応は温度20℃で15時間撹拌しながら行った。以降は実施例1と同様の操作を行って黒色の重合体0.16gを得た。得られた重合体の電気伝導度の測定結果を表1に示す。
重合性単量体としてHTDOを2.6g(18mmol,3.1mol/L相当)、界面活性剤を4.1g(20mmol,3.3mol/L相当)、酸化剤を2.6g(6.5mmol,1.1mol/L相当)用いた以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.20gであり、電気伝導度を測定した結果を表1に示す。
界面活性剤を0.19g(0.91mmol,0.15mol/L)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.12gであり、電気伝導度を測定した結果を表1に示す。
界面活性剤を0.79g(3.8mmol,0.63mol/L相当)とした以外は実施例1と同様の条件で反応を行った。得られた重合体の質量は0.17gであり、電気伝導度を測定した結果を表1に示す。
Claims (12)
- 重合性単量体、界面活性剤、溶媒及び酸化剤の存在下、重合性単量体濃度が0.2〜2.8mol/L、かつ界面活性剤のモル比が重合性単量体1molに対し0.8〜1.6molである初期条件で重合することを特徴とする導電性重合体の製造方法。
- 重合性単量体が2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシンである請求項3に記載の導電性重合体の製造方法。
- 重合性単量体がピロールである請求項5に記載の導電性重合体の製造方法。
- 界面活性剤が有機スルホン酸化合物である請求項1に記載の導電性重合体の製造方法。
- 有機スルホン酸化合物がナフタレンスルホン酸ナトリウムまたはその誘導体である請求項7に記載の導電性重合体の製造方法。
- 酸化剤が鉄塩である請求項1に記載の導電性重合体の製造方法。
- 界面活性剤のモル比が、重合性単量体1molに対し0.9〜1.5molである請求項1に記載の導電性重合体の製造方法。
- 酸化剤のモル比が、重合性単量体1molに対し0.05〜1.5molである請求項1に記載の導電性重合体の製造方法。
- 請求項1乃至11のいずれか1項に記載の製造方法で得られる導電性重合体。
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JPS63101415A (ja) * | 1986-10-09 | 1988-05-06 | ロックウェル・インターナショナル・コーポレーション | 導電性ポリピロールの製造方法 |
JPH09268258A (ja) * | 1995-02-17 | 1997-10-14 | Matsushita Electric Ind Co Ltd | 導電性組成物及びその製造方法 |
JPH10308327A (ja) * | 1997-05-09 | 1998-11-17 | Matsushita Electric Ind Co Ltd | コンデンサの製造方法 |
JP2003160647A (ja) * | 2001-11-27 | 2003-06-03 | Tayca Corp | 導電性高分子およびそれを用いた固体電解コンデンサ |
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EP0298746A2 (en) * | 1987-07-10 | 1989-01-11 | COOKSON GROUP plc | Coated inorganic materials |
DE3729566A1 (de) * | 1987-09-04 | 1989-03-16 | Zipperling Kessler & Co | Intrinsisch leitfaehiges polymer in form eines dispergierbaren feststoffes, dessen herstellung und dessen verwendung |
DE3843412A1 (de) * | 1988-04-22 | 1990-06-28 | Bayer Ag | Neue polythiophene, verfahren zu ihrer herstellung und ihre verwendung |
US5324453A (en) * | 1992-08-07 | 1994-06-28 | Neste Oy | Electrically conducting polyaniline: method for emulsion polymerization |
DE69613414T2 (de) * | 1995-02-17 | 2001-11-08 | Matsushita Electric Industrial Co., Ltd. | Leitfähige Polymerzusammensetzung und Verfahren zur Herstellung derselben |
US6660188B1 (en) * | 1999-04-13 | 2003-12-09 | Showa Denko K.K. | Electrical conducting polymer, solid electrolytic capacitor and manufacturing method thereof |
EP1453877B1 (en) * | 2001-12-04 | 2007-03-28 | Agfa-Gevaert | Process for preparing an aqueous or non-aqueous solution or dispersion of a polythiophene or thiophene copolymer |
US6984341B2 (en) * | 2002-01-22 | 2006-01-10 | Elecon, Inc. | Mixtures comprising thiophene/anion dispersions and certain additives for producing coatings exhibiting improved conductivity, and methods related thereto |
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2005
- 2005-10-07 TW TW094135249A patent/TW200624461A/zh unknown
- 2005-10-12 KR KR1020077008583A patent/KR20070083689A/ko not_active Application Discontinuation
- 2005-10-12 CN CNA2005800351929A patent/CN101039985A/zh active Pending
- 2005-10-12 JP JP2005297407A patent/JP5098049B2/ja active Active
- 2005-10-12 US US11/665,162 patent/US20080125571A1/en not_active Abandoned
- 2005-10-12 EP EP05795296A patent/EP1802678A1/en not_active Withdrawn
- 2005-10-12 WO PCT/JP2005/019154 patent/WO2006041188A1/en active Application Filing
Patent Citations (4)
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JPS63101415A (ja) * | 1986-10-09 | 1988-05-06 | ロックウェル・インターナショナル・コーポレーション | 導電性ポリピロールの製造方法 |
JPH09268258A (ja) * | 1995-02-17 | 1997-10-14 | Matsushita Electric Ind Co Ltd | 導電性組成物及びその製造方法 |
JPH10308327A (ja) * | 1997-05-09 | 1998-11-17 | Matsushita Electric Ind Co Ltd | コンデンサの製造方法 |
JP2003160647A (ja) * | 2001-11-27 | 2003-06-03 | Tayca Corp | 導電性高分子およびそれを用いた固体電解コンデンサ |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007297500A (ja) * | 2006-04-28 | 2007-11-15 | Achilles Corp | 導電性高分子微粒子分散体及びそれを用いる導電性塗料 |
JP2009057520A (ja) * | 2007-09-03 | 2009-03-19 | Idemitsu Kosan Co Ltd | 可溶性の導電性ピロール系重合体及びその製造方法 |
JP2010275548A (ja) * | 2009-05-28 | 2010-12-09 | Showa Denko Kk | 高い導電率を有するポリ(3,4−アルキレンジオキシチオフェン)の製造方法 |
JP2011111521A (ja) * | 2009-11-26 | 2011-06-09 | Nec Tokin Corp | 導電性高分子懸濁液およびその製造方法、導電性高分子材料、電解コンデンサ、ならびに固体電解コンデンサおよびその製造方法 |
WO2011074380A1 (ja) * | 2009-12-18 | 2011-06-23 | テイカ株式会社 | 固体電解コンデンサ |
US8684576B2 (en) | 2009-12-18 | 2014-04-01 | Tayca Corporation | Solid electrolytic capacitor |
JP2011153224A (ja) * | 2010-01-27 | 2011-08-11 | Nec Tokin Corp | 導電性高分子懸濁液およびその製造方法、導電性高分子材料、固体電解コンデンサおよびその製造方法 |
JP2017171759A (ja) * | 2016-03-23 | 2017-09-28 | 東ソー株式会社 | 自己ドープ型ポリチオフェンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20080125571A1 (en) | 2008-05-29 |
TW200624461A (en) | 2006-07-16 |
WO2006041188A8 (en) | 2007-07-05 |
KR20070083689A (ko) | 2007-08-24 |
EP1802678A1 (en) | 2007-07-04 |
JP5098049B2 (ja) | 2012-12-12 |
WO2006041188A1 (en) | 2006-04-20 |
CN101039985A (zh) | 2007-09-19 |
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