KR100543121B1 - 전도성 고분자 폴리티오펜의 제조방법 - Google Patents
전도성 고분자 폴리티오펜의 제조방법 Download PDFInfo
- Publication number
- KR100543121B1 KR100543121B1 KR1020020077465A KR20020077465A KR100543121B1 KR 100543121 B1 KR100543121 B1 KR 100543121B1 KR 1020020077465 A KR1020020077465 A KR 1020020077465A KR 20020077465 A KR20020077465 A KR 20020077465A KR 100543121 B1 KR100543121 B1 KR 100543121B1
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- polythiophene
- producing
- acid catalyst
- polymer
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
Claims (8)
- 3, 4-디알콕시티오펜을 산 촉매 존재하에 용매 중에서 반응시켜 전도성 고분자 폴리티오펜을 제조하는 방법에 있어서,상기 3, 4-디알콕시티오펜은 아래 화학식(2)의 2,5-디할로티오펜이고, 상기 산 촉매는 루이스산, 산소산, 이성분산, 유기산 또는 고분자산 중에서 선택된 하나이며, 질소 조건하에서 반응시킴을 특징으로 하는 아래 화학식(1)의 단위 구조를 포함하는 전도성 고분자 폴리티오펜의 제조방법,화학식(1)화학식(2)상기 식 중, R1 과 R2 는 독립적으로 수소, C1-C4 알킬 그룹, 아릴 치환 C1-C4 알킬렌 그룹, C1-C4 알킬 치환 메틸렌 그룹, C1-C4 알킬기가 치환된 1,2-에틸렌, 1,3-프로필렌, 또는 1,2-시크로헥실렌 그룹 중에서 선택된 하나이고, X는 할로겐 원소인 Cl, Br 또는 I 중에서 선택된 하나이다.
- 제 1항에 있어서, 상기 R1 과 R2는 독립적으로 메틸렌, 1,2-에틸렌, 1,3-프로필렌 중에서 선택된 하나인 것을 특징으로 하는 폴리티오펜의 제조방법.
- 제 1항에 있어서, 상기 용매는 C6-C20의 지방족 및 방향족 탄화수소류, 할로겐 함유 탄화수소류, 케톤, 에테르, C2-C20 알콜, 술폭시드, 아미드, 또는 물 중에서 선택된 하나 임을 특징으로 하는 폴리티오펜의 제조방법.
- 제 3항에 있어서, 상기 용매 중 C6-C20의 지방족 및 방향족 탄화수소류는 알칸류, 알킬벤젠류, 페놀이며, 할로겐 함유 탄화수소류는 할로겐이 치환된 알칸류, 할로벤젠류이며, 케톤류는 아세톤, 프로파논, 부타논, 펜타논, 헥사논, 헵타논, 옥타논 아세토페논이며, 에테르류는 디에틸에테르, 테트라히드로휴란(THF), 디프로필에테르, 디브틸에테르, 메틸부틸에테르, 디페닐에테르, 디옥산(dioxane), 디그림(diglyme), 디에틸렌 글리콜(diethylene glycol), 에틸렌 글리콜(EG)이며, 술폭시드 계열은 디메틸술폭시드(dimethylsulfoxide: DMSO), 아미드 계열은 N,N-디메틸포름아미드(N,N-dimethylformamide: DMF), N-메틸아세트아미드(NMAA), N,N-디메틸아세트아미드(DMA), N-메틸프로피온아미드(NMPA), N-메틸피롤리디논(N-methylpyrrolidinone: NMP)으로서, 상기 용매를 하나 또는 둘 이상을 혼합하여 사용함을 특징으로 하는 폴리티오펜의 제조방법.
- 삭제
- 제 1항에 있어서, 상기 루이스산 촉매는 붕산염, 아연염, 주석염, 철염 중에서 선택된 하나이고, 산소산 촉매는 인산, 황산, 질산, 염산, 차아염소산 중에서 선택된 하나이며, 이성분산 촉매는 HF, HCl, HBr, HI 중에서 선택된 하나, 유기산 촉매는 카르복실산, 파라톨루엔술폰산, 술폰산 중에서 선택된 하나, 고분자산 촉매는 폴리스티렌술폰산, 폴리아크릴산, 폴리메타크릴산, 폴리말레인산, 폴리비닐술폰산 중에서 선택된 하나로서, 상기 산촉매를 하나 또는 둘 이상을 혼합하여 사용함을 특징으로 하는 폴리티오펜의 제조방법.
- 제 6항에 있어서, 상기 산 촉매는 삼불화보론(BF3), 인산, HI, 파라톨루엔술폰산, 폴리스티렌술폰산 중에서 선택된 하나 또는 둘 이상을 혼합하여 사용함을 특징으로 하는 폴리티오펜의 제조방법.
- 제 1항 내지 제 4항, 제 6항, 제 7항 중 어느 한 항에 있어서, 상기 전도성 고분자 폴리티오펜을 강 염기성 수용액에서 교반 후, 얻어진 분말을 극성 용매에 용해시켜 용액상으로 제조함을 특징으로 하는 폴리티오펜의 제조방법.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020020077465A KR100543121B1 (ko) | 2002-12-06 | 2002-12-06 | 전도성 고분자 폴리티오펜의 제조방법 |
US10/728,088 US7034104B2 (en) | 2002-12-06 | 2003-12-05 | Processes for preparing conductive macromolecular polythiophenes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020020077465A KR100543121B1 (ko) | 2002-12-06 | 2002-12-06 | 전도성 고분자 폴리티오펜의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20040049633A KR20040049633A (ko) | 2004-06-12 |
KR100543121B1 true KR100543121B1 (ko) | 2006-01-31 |
Family
ID=32906482
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020020077465A KR100543121B1 (ko) | 2002-12-06 | 2002-12-06 | 전도성 고분자 폴리티오펜의 제조방법 |
Country Status (2)
Country | Link |
---|---|
US (1) | US7034104B2 (ko) |
KR (1) | KR100543121B1 (ko) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1934658A (zh) * | 2004-03-24 | 2007-03-21 | 昭和电工株式会社 | 交联的自掺杂型导电聚合物、其制造方法、用该聚合物涂布的产品和电子器件 |
DE102005031349A1 (de) * | 2005-07-05 | 2007-01-11 | H.C. Starck Gmbh | Verfahren zur Herstellung von Polyethylendioxythiophenen |
EP1916244B1 (en) * | 2005-08-18 | 2013-12-04 | Nissan Chemical Industries, Ltd. | Thiophene compound having sulfonyl group and process for producing the same |
KR100823635B1 (ko) * | 2006-04-17 | 2008-04-21 | 김진열 | 이온 액체를 이용한 전도성 고분자의 나노입자의 제조방법및 이를 이용한 전도성 고분자 컴퍼지트 물질의 제조방법 |
US7649076B2 (en) * | 2006-05-18 | 2010-01-19 | University Of Florida Research Foundation, Inc. | Catalyst free polymerization of 3,4-alkylenedioxypyrrole and 3,4-alkylenedioxyfuran |
KR101087902B1 (ko) * | 2007-06-26 | 2011-11-30 | 데이카 가부시키가이샤 | 도전성 고분자 합성용 산화제겸 도판트, 이의 알콜 용액, 도전성 고분자 및 고체 전해 콘덴서 |
CN102850728B (zh) * | 2008-04-11 | 2015-07-22 | 索尔维美国有限公司 | 掺杂共轭聚合物、器件及器件的制造方法 |
KR100949399B1 (ko) * | 2008-07-11 | 2010-03-24 | 광 석 서 | 유기용제 분산성 전도성 고분자 및 이의 제조방법 |
WO2013059714A1 (en) * | 2011-10-21 | 2013-04-25 | C.R.Bard, Inc. | Systems and methods for ultrasound-based medical device assessment |
US10519328B2 (en) | 2012-10-28 | 2019-12-31 | Polym Technology Corporation | Composition and method for forming electroactive polymer solution or coating comprising conjugated heteroaromatic polymer, electroactive polymer solution, objects comprising the electroactive coating, and solid electrolytic capacitor and method for fabricating the same |
US9627147B2 (en) | 2012-10-28 | 2017-04-18 | Polym Technology Corporation | Composition and method for forming electroactive coating comprising conjugated heteroaromatic polymer, capacitor and antistatic object comprising the electroactive coating, and solid electrolytic capacitor and method for fabricating the same |
US9859062B2 (en) | 2012-10-28 | 2018-01-02 | Polym Technology Corporation | Composition and method for forming electroactive polymer solution or coating comprising conjugated heteroaromatic polymer, electroactive polymer solution, capacitor and antistatic object comprising the electroactive coating, and solid electrolytic capacitor and method for fabricating the same |
US9790330B2 (en) | 2012-10-28 | 2017-10-17 | Polym Technology Corporation | Method for forming conjugated heteroaromatic homopolymer and copolymer, and products thereof |
CN108165140B (zh) * | 2014-06-17 | 2020-05-22 | 博九通科技股份有限公司 | 电活性涂层及形成电活性涂层用的组合物 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4521589A (en) * | 1982-02-26 | 1985-06-04 | Tokyo Institute Of Technology | Linear poly(3-alkyl-2,5-thienylene) polymer |
JPS63234022A (ja) * | 1987-03-20 | 1988-09-29 | Sekisui Chem Co Ltd | 線状ポリ(2,5―チオフェン)の製造方法 |
US5035926A (en) * | 1988-04-22 | 1991-07-30 | Bayer Aktiengesellschaft | Method of imparting antistatic properties to a substrate by coating the substrate with a novel polythiophene |
US5066731A (en) * | 1987-10-26 | 1991-11-19 | Hoechst Aktiengesellschaft | Process for modifying electroconductive polymers using ion exchange |
US5109109A (en) * | 1988-02-09 | 1992-04-28 | Matsushita Electric Industrial Co., Ltd. | Process for producing aromatic or heterocyclic polymer with metal halides |
JPH0790060A (ja) * | 1990-02-08 | 1995-04-04 | Bayer Ag | 新規ポリチオフエン分散体及びその製造方法 |
-
2002
- 2002-12-06 KR KR1020020077465A patent/KR100543121B1/ko active IP Right Grant
-
2003
- 2003-12-05 US US10/728,088 patent/US7034104B2/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4521589A (en) * | 1982-02-26 | 1985-06-04 | Tokyo Institute Of Technology | Linear poly(3-alkyl-2,5-thienylene) polymer |
JPS63234022A (ja) * | 1987-03-20 | 1988-09-29 | Sekisui Chem Co Ltd | 線状ポリ(2,5―チオフェン)の製造方法 |
US5066731A (en) * | 1987-10-26 | 1991-11-19 | Hoechst Aktiengesellschaft | Process for modifying electroconductive polymers using ion exchange |
US5109109A (en) * | 1988-02-09 | 1992-04-28 | Matsushita Electric Industrial Co., Ltd. | Process for producing aromatic or heterocyclic polymer with metal halides |
US5035926A (en) * | 1988-04-22 | 1991-07-30 | Bayer Aktiengesellschaft | Method of imparting antistatic properties to a substrate by coating the substrate with a novel polythiophene |
JPH0790060A (ja) * | 1990-02-08 | 1995-04-04 | Bayer Ag | 新規ポリチオフエン分散体及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20040049633A (ko) | 2004-06-12 |
US20040171790A1 (en) | 2004-09-02 |
US7034104B2 (en) | 2006-04-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4518440B2 (ja) | 中性化合物の使用 | |
Elsenbaumer et al. | Processible and environmentally stable conducting polymers | |
KR100543121B1 (ko) | 전도성 고분자 폴리티오펜의 제조방법 | |
Pei et al. | Electrochromic and highly stable poly (3, 4-ethylenedioxythiophene) switches between opaque blue-black and transparent sky blue | |
JP5339229B2 (ja) | 超原子価ヨウ素反応剤を用いる芳香族化合物および複素環式芳香族化合物のポリマーの製造方法 | |
US7105237B2 (en) | Substituted thieno[3,4-B]thiophene polymers, method of making, and use thereof | |
KR101938922B1 (ko) | 산화성 중합을 통한 공액 중합체의 개선된 합성 및 관련 조성물 | |
US8304512B2 (en) | Benzodithiophene based materials compositions | |
US10538633B2 (en) | Conjugated heteroaromatic homopolymer and copolymer, and applications thereof | |
WO2011056903A1 (en) | Compositions and methods for generating conductive films and coatings of oligomers | |
Chotsuwan et al. | Investigation of the electrochromic properties of tri-block polyaniline-polythiophene-polyaniline under visible light | |
Yamamoto et al. | Neutral poly (3, 4-ethylenedioxythiophene-2, 5-diyl) s: preparation by organometallic polycondensation and their unique p-doping behavior | |
KR102265032B1 (ko) | 축합 헤테로 다환식 화합물 및 그 화합물을 사용한 도전성 폴리머의 제조 방법 | |
Li et al. | Major Classes of Conjugated Polymers and Synthetic Strategies | |
Xu et al. | Low potential electrodeposition of high‐quality and freestanding poly (3‐(6‐bromohexyl) thiophene) films | |
KR101158264B1 (ko) | 용매에 대한 용해도 및 분산성이 우수한 전도성 폴리아닐린 및 그 제조방법 | |
Kaur et al. | Fused heterocycle polymers | |
Zhang | Synthesis and study of (1) poly (2-decylthieno [3, 4-b] thiophene): A low bandgap conducting polymer and (2) poly (alkyl anthranilates): Processable polymers that produce polyaniline | |
Yavuz et al. | Optically Transparent Conducting Polymers from Fused Heterocycles | |
Ombaba | 3, 4-ethylenedioxythiophene derivatives with tuned properties & precursors for solid-state oxidative preparation of polythiophenes | |
Chen | Synthesis and characterization of polythiophene derivatives | |
Chenthamarakshan | Pyrrole-derived oligo-and polysquaraines: Synthesis, optical properties and conductivity studies | |
Lee | Optically transparent, water processable intrinsically conductive polymers | |
Welsh | High contrast and three color electrochromic polymers | |
Agfa-Gevaert | Conductive Polymers |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
N231 | Notification of change of applicant | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20130321 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20131115 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20150106 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20151020 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20161212 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20181108 Year of fee payment: 14 |