DE1620930A1 - Verfahren zur Herstellung von leitendem polymerem Material - Google Patents
Verfahren zur Herstellung von leitendem polymerem MaterialInfo
- Publication number
- DE1620930A1 DE1620930A1 DE19661620930 DE1620930A DE1620930A1 DE 1620930 A1 DE1620930 A1 DE 1620930A1 DE 19661620930 DE19661620930 DE 19661620930 DE 1620930 A DE1620930 A DE 1620930A DE 1620930 A1 DE1620930 A1 DE 1620930A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- poly
- mixture
- tcnq
- hgtcnq
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 239000000463 material Substances 0.000 title claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 65
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 25
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 18
- 229920000885 poly(2-vinylpyridine) Polymers 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 7
- 229920001940 conductive polymer Polymers 0.000 claims description 3
- -1 poly (N, N-dimethylaminoethyl Chemical group 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 5
- MZQXJATZBSCDKH-UHFFFAOYSA-N 1-butyl-2-ethenylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1C=C MZQXJATZBSCDKH-UHFFFAOYSA-N 0.000 claims 1
- YCUMLVMRGKEZPB-UHFFFAOYSA-M 1-ethenylpyridin-1-ium;iodide Chemical compound [I-].C=C[N+]1=CC=CC=C1 YCUMLVMRGKEZPB-UHFFFAOYSA-M 0.000 claims 1
- 241000257303 Hymenoptera Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- HMLSBRLVTDLLOI-UHFFFAOYSA-N 1-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)C(C)OC(=O)C(C)=C HMLSBRLVTDLLOI-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- WASJFLRMRDGSBD-UHFFFAOYSA-N 2-[4-(dicyanomethyl)phenyl]propanedinitrile Chemical compound N#CC(C#N)C1=CC=C(C(C#N)C#N)C=C1 WASJFLRMRDGSBD-UHFFFAOYSA-N 0.000 description 1
- DTJIKSRARSRPBU-UHFFFAOYSA-N 2-ethenyl-1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1C=C DTJIKSRARSRPBU-UHFFFAOYSA-N 0.000 description 1
- GQPSOBOYCYYGBH-UHFFFAOYSA-N 3-butyl-2-ethenylpyridine Chemical compound CCCCC1=CC=CN=C1C=C GQPSOBOYCYYGBH-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- BZRLYGTWEDFWCR-UHFFFAOYSA-N amino 2-methylpent-2-enoate Chemical compound CCC=C(C)C(=O)ON BZRLYGTWEDFWCR-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920002246 poly[2-(dimethylamino)ethyl methacrylate] polymer Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 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
- H01B1/121—Charge-transfer complexes
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44268/65A GB1113216A (en) | 1965-10-19 | 1965-10-19 | Polymer process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620930A1 true DE1620930A1 (de) | 1970-05-14 |
Family
ID=10432513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620930 Pending DE1620930A1 (de) | 1965-10-19 | 1966-10-19 | Verfahren zur Herstellung von leitendem polymerem Material |
Country Status (6)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5132314B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-08-24 | 1976-09-11 | ||
| CA1046127A (en) * | 1974-10-14 | 1979-01-09 | Matsushita Electric Industrial Co., Ltd. | Secondary-electron multiplier including electron-conductive high-polymer composition |
| JPS6013257B2 (ja) * | 1976-02-20 | 1985-04-05 | 松下電器産業株式会社 | 二次電子増倍体およびその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346444A (en) * | 1964-08-24 | 1967-10-10 | Gen Electric | Electrically conductive polymers and process of producing the same |
-
1965
- 1965-10-19 GB GB44268/65A patent/GB1113216A/en not_active Expired
-
1966
- 1966-10-09 JP JP6838166A patent/JPS4518665B1/ja active Pending
- 1966-10-10 US US585248A patent/US3448177A/en not_active Expired - Lifetime
- 1966-10-19 NL NL6614696A patent/NL6614696A/xx unknown
- 1966-10-19 BE BE688509D patent/BE688509A/xx unknown
- 1966-10-19 DE DE19661620930 patent/DE1620930A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4518665B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-06-26 |
| GB1113216A (en) | 1968-05-08 |
| BE688509A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-31 |
| US3448177A (en) | 1969-06-03 |
| NL6614696A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2803528C2 (de) | Schwermetallionen-Adsorbens und dessen Verwendung zum Adsorbieren von Schwermetallionen | |
| DE1959142A1 (de) | Polymerloesung | |
| DE2521985A1 (de) | Verfahren zur herstellung eines polyphenylenaethers | |
| DE1495898A1 (de) | Polymere,Heteroatome enthaltende Acetylenverbindungen | |
| DE3537739C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE69214750T2 (de) | Verfahren zur Herstellung von Tribromstyrol und beta-Bromethyltribrombenzol | |
| DE1620930A1 (de) | Verfahren zur Herstellung von leitendem polymerem Material | |
| DE2056076A1 (de) | Vinyl pyridin/Divinylbenzol Copoly mensat, Verfahren zu dessen Herstellung und Anwendung desselben | |
| DE2431796C2 (de) | Verfahren zur Herstellung von N,N, N',N'-Tetraarylchinondiimonium-Salzen | |
| DE1770605A1 (de) | Verfahren zur Oxydation von Phenolen | |
| DE2630134A1 (de) | Bis-(vinylbenzyl)-monomere | |
| EP0643108B1 (de) | Imidazolylmethylierte Kupferphthalocyaninfarbstoffe | |
| DE2750542A1 (de) | Verfahren zur herstellung von polymeren, die freie oder in salzform befindliche aminische gruppen und quaternaere ammoniumgruppen enthalten sowie die dabei erhaltenen produkte | |
| DE2124591C3 (de) | Verfahren zum Herstellen von Polyäthylen | |
| DE3126264A1 (de) | Polymere mit mindestens zwei stabilen und reversibel umwandelbaren oxidationsstufen und ihre anwendung als redoxsysteme und in der elektrotechnik sowie zur antistatischen ausruestung von kunststoffen | |
| DE3873920T2 (de) | Oligopyridinliganden, verfahren zu ihrer herstellung und ihre verwendung als komplexbildnermittel. | |
| DE68912820T2 (de) | Verfahren zum Herstellen leitender heterozyklischer Polymere, neuer heterozyklischer leitender Polymere, neuer Zwischenerzeugnisse zur Herstellung der Polymere und Synthese der Zwischenerzeugnisse. | |
| DE2829390A1 (de) | Nickelstabilisatorzusammensetzung fuer polyolefine | |
| DE3447463C1 (de) | Verfahren zur Herstellung einer permselektiven und flexiblen Anionenaustauschermembran | |
| DE3829753A1 (de) | Elektrisch leitende polymermischungen | |
| DE1668175C3 (de) | Verfahren zum Monochlorieren von Polyphenylenäthern | |
| DE2241671C3 (de) | Elektrisch leitende Hochpolymerzusammensetzung | |
| DE1693218C3 (de) | 26.12.63 USA 333729 Aminium- und Diimoniumsalze von N,N,N', N'-Tetrakis-(p-aminophenyl)-pphenylendiaminen und -benzidinen American Cyanamid Co., Wayne, N.J. (V.StA.) | |
| DE895152C (de) | Verfahren zur Herstellung von wasserloeslichen Kondensationserzeugnissen | |
| DE1570923A1 (de) | Verfahren zur Herstellung von 1-Olefinpolymerisaten und -mischpolymerisaten |