JPS621651B2 - - Google Patents
Info
- Publication number
- JPS621651B2 JPS621651B2 JP13026081A JP13026081A JPS621651B2 JP S621651 B2 JPS621651 B2 JP S621651B2 JP 13026081 A JP13026081 A JP 13026081A JP 13026081 A JP13026081 A JP 13026081A JP S621651 B2 JPS621651 B2 JP S621651B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- bromo
- ethyl
- polymer
- general formula
- 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
- -1 arylene compound Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 229920000509 poly(aryleneethynylene) polymer Polymers 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 150000003335 secondary amines Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LTLVZQZDXQWLHU-UHFFFAOYSA-N 1-bromo-4-ethynylbenzene Chemical group BrC1=CC=C(C#C)C=C1 LTLVZQZDXQWLHU-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- AHDFNBLZEFXYOG-UHFFFAOYSA-N 6-bromo-9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=C(Br)C=C3C2=C1 AHDFNBLZEFXYOG-UHFFFAOYSA-N 0.000 description 2
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- RTLBWDBZMKHPPN-UHFFFAOYSA-N 3-ethenyl-9-ethylcarbazole Chemical compound C=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 RTLBWDBZMKHPPN-UHFFFAOYSA-N 0.000 description 1
- WNBBSHAXYFKBPZ-UHFFFAOYSA-N 9-dodecylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CCCCCCCCCCCC)C3=CC=CC=C3C2=C1 WNBBSHAXYFKBPZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13026081A JPS5832629A (ja) | 1981-08-21 | 1981-08-21 | ポリアリ−レン・エチニレンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13026081A JPS5832629A (ja) | 1981-08-21 | 1981-08-21 | ポリアリ−レン・エチニレンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5832629A JPS5832629A (ja) | 1983-02-25 |
| JPS621651B2 true JPS621651B2 (ko) | 1987-01-14 |
Family
ID=15030005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13026081A Granted JPS5832629A (ja) | 1981-08-21 | 1981-08-21 | ポリアリ−レン・エチニレンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5832629A (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4631298A (en) * | 1985-12-16 | 1986-12-23 | Ethyl Corporation | Mixed diamine chain extender |
| DE3719851A1 (de) * | 1987-06-13 | 1988-12-29 | Bayer Ag | Vinylencopolymerisate |
| US5227457A (en) * | 1988-02-17 | 1993-07-13 | Maxdem Incorporated | Rigid-rod polymers |
| US5646231A (en) * | 1988-02-17 | 1997-07-08 | Maxdem, Incorporated | Rigid-rod polymers |
-
1981
- 1981-08-21 JP JP13026081A patent/JPS5832629A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5832629A (ja) | 1983-02-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS62155230A (ja) | （２，２）−パラシクロフアン及びそれらの誘導体の製造方法 | |
| JPH04506352A (ja) | １，４―ビス―（４―ヒドロキシベンゾイル）―ベンゼンの製法 | |
| JP2004517042A (ja) | オレフィン置換芳香族または複素芳香族の製造方法 | |
| JPS60199847A (ja) | ３，５−ジメトキシ−４−アルコキシベンツアルデヒドの製法 | |
| JPS621651B2 (ko) | ||
| JPS5848532B2 (ja) | 準安定状態を有する安息香酸誘導体 | |
| CA1040656A (en) | Phenoxyalkylamine derivatives and preparation thereof | |
| JPH10195181A (ja) | 耐熱性ポリ−α，α−ジフルオロ−パラキシリレン膜 | |
| JP2730757B2 (ja) | 導電性複素環式重合体およびその製造方法 | |
| JPS6160850B2 (ko) | ||
| JPH04501861A (ja) | プロゲステロン―誘導体の製法 | |
| JPS6160851B2 (ko) | ||
| EP0059646A2 (en) | Conjugated polymers and processes for preparing and modifying them | |
| EP1120391B1 (en) | Molecular compounds containing novel carboxylic acid derivatives as the constituent compound | |
| JPH0399084A (ja) | マロンアミド誘導体金属錯体及び芳香族化合物用分離剤 | |
| JP2706554B2 (ja) | ４―トリフルオロメチルアニリン誘導体及びその製造法 | |
| JPH0327549B2 (ko) | ||
| JPS6337132B2 (ko) | ||
| SU258311A1 (ru) | Способ получени циклометаллотетрасилазанов | |
| JPH0586181A (ja) | 新規なポリアミド | |
| JP2564141B2 (ja) | アルキルベンゾチアゾール類の製造方法 | |
| JPH0465817B2 (ko) | ||
| JPH0215536B2 (ko) | ||
| JPH07505140A (ja) | ３−カルボニルアンドロスタジエン１７−カルボキシアミドの製法 | |
| JPS60161936A (ja) | α−（ペルフルオロアルキル）カルビノ−ルの製造方法 |