JPH01115929A - ジアセチレン基を含有するポリアミドの製造方法 - Google Patents
ジアセチレン基を含有するポリアミドの製造方法Info
- Publication number
- JPH01115929A JPH01115929A JP27167287A JP27167287A JPH01115929A JP H01115929 A JPH01115929 A JP H01115929A JP 27167287 A JP27167287 A JP 27167287A JP 27167287 A JP27167287 A JP 27167287A JP H01115929 A JPH01115929 A JP H01115929A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- diacetylene
- containing diacetylene
- polymer
- 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.)
- Granted
Links
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000004952 Polyamide Substances 0.000 title claims description 19
- 229920002647 polyamide Polymers 0.000 title claims description 19
- 125000000962 organic group Chemical group 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 19
- -1 diamine compound Chemical class 0.000 abstract description 12
- 238000006116 polymerization reaction Methods 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006068 polycondensation reaction Methods 0.000 abstract description 5
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012761 high-performance material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- GRRYWLJOGFTFJH-UHFFFAOYSA-N 4-[4-(4-carbonochloridoylphenyl)buta-1,3-diynyl]benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C#CC#CC1=CC=C(C(Cl)=O)C=C1 GRRYWLJOGFTFJH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- LCEFDICNHKVNSF-UHFFFAOYSA-N but-2-ynedioyl dichloride Chemical compound ClC(=O)C#CC(Cl)=O LCEFDICNHKVNSF-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JPGRSTBIEYGVNO-UHFFFAOYSA-N methyl 4-ethynylbenzoate Chemical compound COC(=O)C1=CC=C(C#C)C=C1 JPGRSTBIEYGVNO-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polyamides (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27167287A JPH01115929A (ja) | 1987-10-29 | 1987-10-29 | ジアセチレン基を含有するポリアミドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27167287A JPH01115929A (ja) | 1987-10-29 | 1987-10-29 | ジアセチレン基を含有するポリアミドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01115929A true JPH01115929A (ja) | 1989-05-09 |
| JPH0359088B2 JPH0359088B2 (enrdf_load_stackoverflow) | 1991-09-09 |
Family
ID=17503270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27167287A Granted JPH01115929A (ja) | 1987-10-29 | 1987-10-29 | ジアセチレン基を含有するポリアミドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01115929A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002024785A1 (fr) * | 2000-09-21 | 2002-03-28 | Sumitomo Bakelite Company, Ltd. | Precurseur de resine resistant a la chaleur, resine resistante a la chaleur, couche isolante isolant et dispositif semiconducteur |
| US6518390B2 (en) | 2000-03-29 | 2003-02-11 | Sumitomo Bakelite Company, Ltd. | Precursor of a heat resistant resin, heat resistant resin, insulating film and semiconductor device |
| JP2005015406A (ja) * | 2003-06-27 | 2005-01-20 | Fuji Photo Film Co Ltd | 化合物、液晶材料、液晶組成物、光学フィルム、及び該化合物の製造方法 |
| EP1158839A3 (en) * | 2000-04-27 | 2006-01-11 | Fujitsu Limited | Organic luminous material and organic light-emitting device |
| WO2010036170A1 (en) * | 2008-09-23 | 2010-04-01 | Nexam Chemical Ab | Acetylenic polyamide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0198626A (ja) * | 1987-10-12 | 1989-04-17 | Agency Of Ind Science & Technol | ジアセチレン基を含有するポリアミドの成形体 |
-
1987
- 1987-10-29 JP JP27167287A patent/JPH01115929A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0198626A (ja) * | 1987-10-12 | 1989-04-17 | Agency Of Ind Science & Technol | ジアセチレン基を含有するポリアミドの成形体 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6518390B2 (en) | 2000-03-29 | 2003-02-11 | Sumitomo Bakelite Company, Ltd. | Precursor of a heat resistant resin, heat resistant resin, insulating film and semiconductor device |
| EP1158839A3 (en) * | 2000-04-27 | 2006-01-11 | Fujitsu Limited | Organic luminous material and organic light-emitting device |
| EP1760799A3 (en) * | 2000-04-27 | 2007-06-27 | Fujitsu Ltd. | Organic luminous material and organic light-emitting device |
| WO2002024785A1 (fr) * | 2000-09-21 | 2002-03-28 | Sumitomo Bakelite Company, Ltd. | Precurseur de resine resistant a la chaleur, resine resistante a la chaleur, couche isolante isolant et dispositif semiconducteur |
| KR100787284B1 (ko) * | 2000-09-21 | 2007-12-20 | 스미토모 베이클리트 컴퍼니 리미티드 | 내열성 수지 전구체, 내열성 수지 및 절연막 및 반도체장치 |
| JP2005015406A (ja) * | 2003-06-27 | 2005-01-20 | Fuji Photo Film Co Ltd | 化合物、液晶材料、液晶組成物、光学フィルム、及び該化合物の製造方法 |
| WO2010036170A1 (en) * | 2008-09-23 | 2010-04-01 | Nexam Chemical Ab | Acetylenic polyamide |
| US8492507B2 (en) | 2008-09-23 | 2013-07-23 | Nexam Chemical Ab | Acetylenic polyamide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0359088B2 (enrdf_load_stackoverflow) | 1991-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |