JPS6139981B2 - - Google Patents
Info
- Publication number
- JPS6139981B2 JPS6139981B2 JP5024579A JP5024579A JPS6139981B2 JP S6139981 B2 JPS6139981 B2 JP S6139981B2 JP 5024579 A JP5024579 A JP 5024579A JP 5024579 A JP5024579 A JP 5024579A JP S6139981 B2 JPS6139981 B2 JP S6139981B2
- Authority
- JP
- Japan
- Prior art keywords
- acetylene
- polymer
- group
- electron
- electrical conductivity
- 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.)
- Expired
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 58
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 58
- 229920000642 polymer Polymers 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000004065 semiconductor Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229930192627 Naphthoquinone Natural products 0.000 claims description 3
- 150000002791 naphthoquinones Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003623 transition metal compounds Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 239000013081 microcrystal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 2
- -1 5 − cyclopentadienyl Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 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 2
- 239000010936 titanium Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 1
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- IGIPYJUEWJRUGN-UHFFFAOYSA-N 2,6-dinitrocyclohexa-2,5-diene-1,4-dione Chemical compound [O-][N+](=O)C1=CC(=O)C=C([N+]([O-])=O)C1=O IGIPYJUEWJRUGN-UHFFFAOYSA-N 0.000 description 1
- DFJXWQJAMNCPII-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,5-dimethylcyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound CC1=CC(=C(C#N)C#N)C(C)=CC1=C(C#N)C#N DFJXWQJAMNCPII-UHFFFAOYSA-N 0.000 description 1
- JNDXMMOQWQUXML-UHFFFAOYSA-N 2-nitrosonaphthalen-1-amine Chemical compound C1=CC=C2C(N)=C(N=O)C=CC2=C1 JNDXMMOQWQUXML-UHFFFAOYSA-N 0.000 description 1
- JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 1
- DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 description 1
- JCEXBUYUHYXFME-UHFFFAOYSA-N 4-nitrosonaphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=C(N=O)C2=C1 JCEXBUYUHYXFME-UHFFFAOYSA-N 0.000 description 1
- ZVNOVIBCAIDQOE-UHFFFAOYSA-N 4-nitrosonaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(N=O)C2=C1 ZVNOVIBCAIDQOE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SLBHRPOLVUEFSG-UHFFFAOYSA-N naphthalene-2,6-dione Chemical compound O=C1C=CC2=CC(=O)C=CC2=C1 SLBHRPOLVUEFSG-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 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
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5024579A JPS55143703A (en) | 1979-04-25 | 1979-04-25 | High molecular semiconductor |
| PCT/JP1980/000052 WO1980002146A1 (en) | 1979-03-29 | 1980-03-28 | Process for preparing highly conductive acetylene high polymer |
| DE3041420A DE3041420C1 (de) | 1979-03-29 | 1980-03-28 | Verfahren zur Herstellung von elektrisch leitenden Acetylenhochpolymeren |
| US06/224,518 US4487709A (en) | 1979-03-29 | 1980-03-28 | Process for producing electrically conductive high polymer of acetylene |
| GB8037339A GB2061291B (en) | 1979-03-29 | 1980-03-28 | Process for preparing highly conductive acetylene high polymer |
| EP80900609A EP0026234B1 (en) | 1979-03-29 | 1980-10-23 | Process for preparing highly conductive acetylene high polymer |
| US06/657,266 US4594180A (en) | 1979-03-29 | 1984-10-03 | Process for producing electrically conductive high polymer of acetylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5024579A JPS55143703A (en) | 1979-04-25 | 1979-04-25 | High molecular semiconductor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55143703A JPS55143703A (en) | 1980-11-10 |
| JPS6139981B2 true JPS6139981B2 (en, 2012) | 1986-09-06 |
Family
ID=12853599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5024579A Granted JPS55143703A (en) | 1979-03-29 | 1979-04-25 | High molecular semiconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55143703A (en, 2012) |
-
1979
- 1979-04-25 JP JP5024579A patent/JPS55143703A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55143703A (en) | 1980-11-10 |
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