JP5236879B2 - 真性導電性重合体の分散液およびその製造方法 - Google Patents
真性導電性重合体の分散液およびその製造方法 Download PDFInfo
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- JP5236879B2 JP5236879B2 JP2006550052A JP2006550052A JP5236879B2 JP 5236879 B2 JP5236879 B2 JP 5236879B2 JP 2006550052 A JP2006550052 A JP 2006550052A JP 2006550052 A JP2006550052 A JP 2006550052A JP 5236879 B2 JP5236879 B2 JP 5236879B2
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Classifications
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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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/14—Treatment of polymer emulsions
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions 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 C08L61/00 - C08L77/00
- C08L79/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive 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
- Y02E60/13—Energy storage using capacitors
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Power Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
(a) 単量体から真性導電性重合体が調製され、重合時の温度は出発温度より5℃高い数値を超えないように制御され、
(b) 適当な剪断力を適用しながら、導電性重合体に比べ不活性である非導電性非重合極性物質の存在下に段階(a)の製品が粉砕混和および/または分散され、導電性重合体と極性物質との重量比は2:1〜1:10であり、
(c) 段階(b)の製品は室温で液体である分散剤中に分散され、導電性重合体と分散剤との重量比は1:10未満である。
・30dyn/cmより大の表面張力を持つ、
・導電性ではない(すなわち、10-6S/cm未満の導電率を持つ)、
・液体または固体であることができる、
・用いられた導電性重合体に比べ不活性である。すなわち、有意な化学反応を伴わない;とりわけ、酸化的または還元的かつ酸−塩基反応が望まれない、
・通常の条件下では、必ずしも分散助剤でなく、界面活性剤の物質群に該当しない。
a) 固体: 硫酸バリウム;二酸化チタン、特に、300nm未満の粒度を持つ超微細二酸化チタン;ピグメントイエロー18のような有機顔料;
b) 不活性溶媒: 水、DMF、DMSO、γ−ブチロラクトン、NMPおよび他のピロリドン誘導体、ジオキサン、THF;
であるが、この列挙は例示のためである。
− 電気導体(例えば、電気接点、電気導線、押しボタンスイッチ、電極等)または半導体として、
− 静電荷に対する防御として、
− 電磁波の遮蔽(EMI遮蔽)のため、
− マイクロ波吸収のため(遮蔽または加熱目的のため)、
− コンデンサ製造のため、または電解コンデンサにおける電解質の代替品として、
− いわゆる“スーパーコンデンサ”における電極または電極部品として(この種のコンデンサも二層コンデンサ(DLC)と呼ばれ、カーボンブラックおよび/またはグラファイト系であることが多い電気二重層の形成を特徴とする;これらは“電気化学二層コンデンサ”と言われることが多い)、
− ダイオード、とりわけ、トランジスタなどの半導体素子の製造のため、
− 光導電体として、または光起電力エネルギー変換において、
− 温度センサとして熱電効果を利用した金属または半金属を持つ組成において、または各種導電性重合体を持つ組成において(IR吸収)、または光起電力エネルギー変換において、
− センサとして、
− 例えばエレクトロクロミズム、マイクロ波吸収、熱電力等によるインジケータとして、
− 電気分解または電気合成工程において電気触媒電極として(例えば燃料電池において)、
− 光電気触媒反応または合成において、および光起電効果の場合に、
− 腐食防御において、例えば陽極腐食防御の場合に、
− アキュムレータにおける電極として、
− UV−および光安定性顔料として、
− エレクトロルミネッセンスシステムにおける電極または導線として(例えば、不透明ないわゆる“後方電極”として、または透明ないわゆる“前方電極”として)、
− 有機/重合性光ダイオードまたは太陽電池におけるホール注入層または陽極緩衝層または透明陽極として。
温度を制御するのに必要な冷却は、少なくとも0.02K/分、好ましくは0.05K/分の冷却速度で維持した。これらの冷却速度は、反応を開始しないで、各々の場合に用いられる反応容器で冷却を作動したときの温度変化を測定することにより決定した。
高速実験室用ミキサー中、実施例1のように調製したポリアニリンを、以下の表において各々の場合に示された比率で用いられた物質と共に3分間乾燥粉末として分散した。
実施例1にしたがい得られた粉末を実験室用混練機においてPMMAと共に溶融液中90℃で分散した。ポリアニリンとポリメチレンメタクリレートの混合物に対し約40重量%のポリアニリン濃度を用いた。
実施例2の予備分散液200gを流動床抽出装置において1リットルのキシレンで抽出した。残留水分70重量%で約400gが得られた。
実施例3の抽出残渣200gをビーズミルにおいて2.5時間600gのキシレンで分散させた。約4重量%のポリアニリン含量を持つ高粘度ペーストが得られた。
実施例4のペースト10gをジクロロ酢酸10gとジクロロメタン10gで希釈し、次に攪拌し、1500rpmの速度のスピンコート装置でガラス基材に塗布した。乾燥後、220S/cmの導電率を持つ150nmの層厚みができた。
実施例2の予備分散液50gをガラスフラスコにおいて300mlのクロロベンゼンで10分間洗浄した。混合物はろ過した。固形分40重量%とポリアニリン計算濃度約0.15重量%の湿潤残渣が得られた。
実施例6のろ過残渣0.2gを超音波下、10mlのクロロフェノールと混合し、エネルギー密度500W/m2の超音波に20分間暴露した。安定な分散液が生成された。
実施例7の分散液を10mlのクロロフェノールで希釈し、この希釈液8 mlをペトリ皿に注いだ。この皿を50℃の温度で6時間乾燥した。層厚み25μmと導電率540S/cmの自立皮膜が生成された。
Claims (19)
- 真性導電性重合体の粒子を含有する分散液であって、粒度は平均(重量)して1μm未満の分散液において、分散剤は室温で液体であり、この分散液から形成される層、皮膜またはシートは分散剤の除去後では100S/cmを超える導電率を持ち、上記真性導電性重合体はポリアニリンである、
ことを特徴とする分散液。 - 導電率が少なくとも200S/cmである
ことを特徴とする請求項1記載の分散液。 - 導電率が300S/cm〜3000S/cmである
ことを特徴とする請求項2記載の分散液。 - 分散剤が10000未満の相対粘度を持つ
ことを特徴とする上記請求項1乃至3のいずれか記載の分散液。 - 請求項1乃至4のいずれか記載の分散液の製造方法であって、
以下の順序で行われる製造方法:
(a) 単量体から真性導電性重合体が調製され、重合時の温度は出発温度より5℃高い数値を超えないように制御されると共に、重合中の温度上昇速度が1K/分未満であり、
(b) 適当な剪断力を適用しながら、導電性重合体に比べ不活性である非導電性非重合極性物質の存在下に段階(a)の製品が粉砕混和および/または分散され、導電性重合体と極性物質との重量比は2:1〜1:10であり、
(c) 段階(b)の製品は室温で液体である分散剤中に分散され、導電性重合体と分散剤との重量比は1:10未満である。 - 段階(b)において、さらに少なくとも1種類の非導電性重合体が存在する
ことを特徴とする請求項5記載の製造方法。 - 非導電性重合体が熱可塑性重合体である
ことを特徴とする請求項6記載の製造方法。 - 段階(b)の製品は後処理に付される
ことを特徴とする請求項5乃至7のいずれか記載の製造方法。 - 段階(b)の製品中の極性物質または非導電性重合体の一部は洗浄または抽出による後処理中に減少される
ことを特徴とする請求項8記載の製造方法。 - 次の分散段階(c)を支える溶媒および/または助剤が添加される
ことを特徴とする請求項5乃至9のいずれか記載の製造方法。 - 段階(c)の製品が後処理に付される
ことを特徴とする請求項5乃至10のいずれか記載の製造方法。 - 必要により続く付形工程を支える粘度調整剤、湿潤助剤、マトリックス重合体、安定剤、架橋助剤、蒸発調整剤および/または他の助剤および添加剤が添加される
ことを特徴とする請求項5乃至11のいずれか記載の製造方法。 - 添加は段階(c)前または段階(c)中に行われる
ことを特徴とする請求項12記載の製造方法。 - 段階(b)の製品の後処理中および/または分散段階(c)中に、25mN/mより大きい表面張力を持つ有機溶媒が用いられる
ことを特徴とする請求項5乃至13のいずれか記載の製造方法。 - 段階(b)の製品の後処理中に導電性重合体の濃度は、室温で固形の成分に対し少なくとも5重量%増大する
ことを特徴とする請求項8乃至14のいずれか記載の製造方法。 - 分散段階は、ボールミル、ビーズミル、3本ロール機、および高圧分散装置からなる群から選ばれる分散装置中で実施される
ことを特徴とする請求項5乃至15のいずれか記載の製造方法。 - 分散は超音波下で実施される
ことを特徴とする請求項5乃至15のいずれか記載の製造方法。 - 請求項1乃至4のいずれか記載の分散液、または請求項5乃至17のいずれか記載の製造方法にしたがい製造された分散液の使用。
- 成形品、自立皮膜または塗膜は電極、アンテナ、重合電子部品、コンデンサおよび二層コンデンサ(DLC)である
ことを特徴とする請求項18記載の使用。
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DE102004003784A DE102004003784B4 (de) | 2004-01-23 | 2004-01-23 | Dispersion intrinsisch leitfähigen Polyanilins und deren Verwendung |
DE102004003784.1 | 2004-01-23 | ||
PCT/EP2005/000595 WO2005070972A1 (de) | 2004-01-23 | 2005-01-21 | Dispersionen intrinsisch leitfähiger polymere und verfahren zu deren herstellung |
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CN (1) | CN100523005C (ja) |
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2004
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2005
- 2005-01-21 CN CNB2005800028275A patent/CN100523005C/zh not_active Expired - Fee Related
- 2005-01-21 KR KR1020067015215A patent/KR101138295B1/ko active IP Right Grant
- 2005-01-21 JP JP2006550052A patent/JP5236879B2/ja active Active
- 2005-01-21 US US10/597,170 patent/US7683124B2/en not_active Expired - Fee Related
- 2005-01-21 WO PCT/EP2005/000595 patent/WO2005070972A1/de active Application Filing
- 2005-01-21 CA CA002553467A patent/CA2553467A1/en not_active Abandoned
- 2005-01-21 EP EP05706959.3A patent/EP1706431B1/de not_active Not-in-force
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Also Published As
Publication number | Publication date |
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WO2005070972A1 (de) | 2005-08-04 |
CA2553467A1 (en) | 2005-08-04 |
DE102004003784A1 (de) | 2005-08-18 |
KR101138295B1 (ko) | 2012-04-24 |
US8344062B2 (en) | 2013-01-01 |
JP2007518859A (ja) | 2007-07-12 |
EP1706431A1 (de) | 2006-10-04 |
US7683124B2 (en) | 2010-03-23 |
CN1910204A (zh) | 2007-02-07 |
KR20070007274A (ko) | 2007-01-15 |
DE102004003784B4 (de) | 2011-01-13 |
US20100133478A1 (en) | 2010-06-03 |
CN100523005C (zh) | 2009-08-05 |
EP1706431B1 (de) | 2016-03-23 |
US20070267747A1 (en) | 2007-11-22 |
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