CA2309194A1 - Compositions polymeres conductrices - Google Patents
Compositions polymeres conductrices Download PDFInfo
- Publication number
- CA2309194A1 CA2309194A1 CA002309194A CA2309194A CA2309194A1 CA 2309194 A1 CA2309194 A1 CA 2309194A1 CA 002309194 A CA002309194 A CA 002309194A CA 2309194 A CA2309194 A CA 2309194A CA 2309194 A1 CA2309194 A1 CA 2309194A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- fluid mixture
- polyaniline
- solvent
- sulfonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 7
- 229920000767 polyaniline Polymers 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000012530 fluid Substances 0.000 claims abstract description 25
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 16
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 15
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960005215 dichloroacetic acid Drugs 0.000 claims abstract description 8
- 229920000775 emeraldine polymer Polymers 0.000 claims abstract description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002166 wet spinning Methods 0.000 claims abstract description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 239000000758 substrate Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- -1 1,1-dimethyl-2-hydroxyethyl Chemical group 0.000 claims description 5
- DBXNUXBLKRLWFA-UHFFFAOYSA-N N-(2-acetamido)-2-aminoethanesulfonic acid Chemical compound NC(=O)CNCCS(O)(=O)=O DBXNUXBLKRLWFA-UHFFFAOYSA-N 0.000 claims description 5
- AJTVSSFTXWNIRG-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OCC[NH+](CCO)CCS([O-])(=O)=O AJTVSSFTXWNIRG-UHFFFAOYSA-N 0.000 claims description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000007991 ACES buffer Substances 0.000 claims description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 claims description 2
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims description 2
- MQLJIOAPXLAGAP-UHFFFAOYSA-N 3-[amino(azaniumylidene)methyl]sulfanylpropane-1-sulfonate Chemical compound NC(=N)SCCCS(O)(=O)=O MQLJIOAPXLAGAP-UHFFFAOYSA-N 0.000 claims description 2
- XCBLFURAFHFFJF-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)azaniumyl]-2-hydroxypropane-1-sulfonate Chemical compound OCCN(CCO)CC(O)CS(O)(=O)=O XCBLFURAFHFFJF-UHFFFAOYSA-N 0.000 claims description 2
- JVQYSWDUAOAHFM-UHFFFAOYSA-N 3-methyl-2-oxovaleric acid Chemical compound CCC(C)C(=O)C(O)=O JVQYSWDUAOAHFM-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229940107700 pyruvic acid Drugs 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 2
- 239000010408 film Substances 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical group OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000002019 doping agent Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000002860 competitive effect Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007712 rapid solidification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Un mélange polymère conducteur fluide destiné à être utilisé dans la préparation de revêtements de films et de fibres est principalement constitué d'une polyaniline sous forme de base (de préférence d'émeraldine sous forme de base). Dans cette invention on dope la polyaniline avec un acide sulfonique comprenant en plus d'au moins un groupe acide sulfonique, un deuxième groupe fonctionnel à liaison hydrogène et on disperse cette aniline dopée dans un solvant acide présentant une valeur pK¿a? inférieure à 4,5 mais sensiblement supérieure (plus positive) à celle de l'acide sulfonique. L'acide sulfonique fonctionnel semble agir en tant qu'agent de solvatation ainsi qu'en tant que dopant et permet de former des mélanges à forte teneur en solides dans les solvants acides (jusqu'à environ 15 % en poids si on le compare avec un maximum d'environ 10 % dans des mélanges classiques à base de NMP) desquels on peut extraire le solvant avec un solvant concurrent (par exemple dans un procédé de filage au mouillé); ceci permettant de produire des films et des fibres étirables à froid (et à chaud). L'acide sulfonique préféré est le 2-acrylamido-2-méthyle-1-acide propane sulfonique (AMPSA) ou son oligomère et le solvant acide préféré est l'acide dichloroacétique. Le solvant concurrent peut être l'acétone, le méthyle isobutyle cétone ou l'acétate de butyle.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9723464.5 | 1997-11-07 | ||
| GBGB9723464.5A GB9723464D0 (en) | 1997-11-07 | 1997-11-07 | Conductive polymer compositions |
| GBGB9801159.6A GB9801159D0 (en) | 1998-01-21 | 1998-01-21 | Conductive polymer compositions |
| GB9801159.6 | 1998-01-21 | ||
| PCT/GB1998/003241 WO1999024991A1 (fr) | 1997-11-07 | 1998-10-30 | Compositions polymeres conductrices |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2309194A1 true CA2309194A1 (fr) | 1999-05-20 |
Family
ID=26312561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002309194A Abandoned CA2309194A1 (fr) | 1997-11-07 | 1998-10-30 | Compositions polymeres conductrices |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1029329A1 (fr) |
| JP (1) | JP2001522898A (fr) |
| AU (1) | AU9637798A (fr) |
| CA (1) | CA2309194A1 (fr) |
| WO (1) | WO1999024991A1 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5888582A (en) * | 1997-12-09 | 1999-03-30 | Kemet Electronics Corp. | Polyaniline solutions with bicyclic terpene solvent |
| FR2796379B1 (fr) * | 1999-07-13 | 2002-05-24 | Commissariat Energie Atomique | Acides sulfoniques et phosphoniques et leur utilisation comme dopants pour la fabrication de films conducteurs de polyaniline et pour la fabrication de materiaux composites conducteurs a base de polyaniline |
| US6982514B1 (en) | 2000-05-22 | 2006-01-03 | Santa Fe Science And Technology, Inc. | Electrochemical devices incorporating high-conductivity conjugated polymers |
| US6936955B1 (en) | 2000-08-04 | 2005-08-30 | Santa Fe Science And Technology, Inc. | Conjugated polymer actuator responsive to electrical stimulation |
| KR100401349B1 (ko) * | 2000-09-20 | 2003-10-17 | 스마트텍 주식회사 | 전도성 폴리아닐린 방사용액의 제조 방법 |
| AUPR831101A0 (en) * | 2001-10-16 | 2001-11-08 | University Of Wollongong, The | Separation and recovery of precious metals using polymer materials |
| KR20050074519A (ko) * | 2002-10-30 | 2005-07-18 | 산타 페 사이언스 앤드 테크놀로지, 인코포레이티드 | 폴리아닐린 섬유의 스피닝, 도핑, 디도핑 그리고 리도핑 |
| AU2003293334A1 (en) | 2002-12-02 | 2004-06-23 | Santa Fe Science And Technology, Inc. | Resistive heating using polyaniline fiber |
| US7288871B1 (en) | 2003-07-03 | 2007-10-30 | Santa Fe Science And Technology, Inc. | Solid-in-hollow polymer fiber electrochemical devices |
| US7463040B2 (en) | 2003-08-01 | 2008-12-09 | Santa Fe Science And Technology, Inc. | Multifunctional conducting polymer structures |
| WO2005096392A2 (fr) | 2004-03-31 | 2005-10-13 | The Yokohama Rubber Co., Ltd. | Électrolyte pour dispositif photovoltaïque, dispositif photovoltaïque et pile solaire sensibilisée à la matière colorante comprenant cette électrolyte. |
| US8691028B2 (en) * | 2006-05-10 | 2014-04-08 | The Boeing Company | Article having a hexavalent-chromium-free, corrosion-inhibiting organic conversion coating thereon, and its preparation |
| JP5515089B2 (ja) * | 2008-06-05 | 2014-06-11 | 日産自動車株式会社 | 導電性高分子繊維およびその製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262195A (en) * | 1990-11-05 | 1993-11-16 | Brewer Science | Soluble conducting polymers and their use in manufacturing electronic devices |
| US5520852A (en) * | 1994-06-08 | 1996-05-28 | Neste Oy | Processible electrically conducting polyaniline compositions |
| KR970058474A (ko) * | 1995-12-20 | 1997-07-31 | 정몽원 | 전자파 차폐용 케이스 |
-
1998
- 1998-10-30 AU AU96377/98A patent/AU9637798A/en not_active Abandoned
- 1998-10-30 WO PCT/GB1998/003241 patent/WO1999024991A1/fr not_active Ceased
- 1998-10-30 JP JP2000519900A patent/JP2001522898A/ja active Pending
- 1998-10-30 CA CA002309194A patent/CA2309194A1/fr not_active Abandoned
- 1998-10-30 EP EP98950224A patent/EP1029329A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999024991A1 (fr) | 1999-05-20 |
| JP2001522898A (ja) | 2001-11-20 |
| AU9637798A (en) | 1999-05-31 |
| EP1029329A1 (fr) | 2000-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |