JP2015514730A5 - - Google Patents
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- Publication number
- JP2015514730A5 JP2015514730A5 JP2015506134A JP2015506134A JP2015514730A5 JP 2015514730 A5 JP2015514730 A5 JP 2015514730A5 JP 2015506134 A JP2015506134 A JP 2015506134A JP 2015506134 A JP2015506134 A JP 2015506134A JP 2015514730 A5 JP2015514730 A5 JP 2015514730A5
- Authority
- JP
- Japan
- Prior art keywords
- dione
- ethyne
- bis
- isobenzofuran
- diyl
- 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
- 238000000034 method Methods 0.000 claims 15
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- RZNRHYDJQKHHOQ-UHFFFAOYSA-N 4-[2-(1,3-dioxo-2-benzofuran-4-yl)ethynyl]-2-benzofuran-1,3-dione Chemical compound O=C1OC(=O)C2=C1C=CC=C2C#CC1=CC=CC2=C1C(=O)OC2=O RZNRHYDJQKHHOQ-UHFFFAOYSA-N 0.000 claims 7
- -1 chloro - Chemical class 0.000 claims 7
- SKHCDRLTAOLKHQ-UHFFFAOYSA-N 4-iodo-2-benzofuran-1,3-dione Chemical compound IC1=CC=CC2=C1C(=O)OC2=O SKHCDRLTAOLKHQ-UHFFFAOYSA-N 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical group [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 238000005406 washing Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000003599 detergent Substances 0.000 claims 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 241000255925 Diptera Species 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 150000003839 salts Chemical group 0.000 claims 2
- XGZRRDYHYZLYIJ-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)ethynyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C#CC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 XGZRRDYHYZLYIJ-UHFFFAOYSA-N 0.000 claims 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012459 cleaning agent Substances 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12164900.8A EP2653467B1 (en) | 2012-04-20 | 2012-04-20 | Process for producing (ethyne-1,2-diyl)bis(isobenzofuran-1,3- dione) |
| EP12164900.8 | 2012-04-20 | ||
| PCT/EP2013/054686 WO2013156200A1 (en) | 2012-04-20 | 2013-03-08 | Process for producing (ethyne-1,2-diyl)bis(isobenzofuran-1,3- dione) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015514730A JP2015514730A (ja) | 2015-05-21 |
| JP2015514730A5 true JP2015514730A5 (cg-RX-API-DMAC7.html) | 2016-04-14 |
| JP6138237B2 JP6138237B2 (ja) | 2017-05-31 |
Family
ID=47843291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015506134A Active JP6138237B2 (ja) | 2012-04-20 | 2013-03-08 | （エチン−１，２−ジイル）ビス（イソベンゾフラン−１，３−ジオン）を生成する方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9018401B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2653467B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6138237B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102081717B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104245685B (cg-RX-API-DMAC7.html) |
| ES (1) | ES2523824T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2014145135A (cg-RX-API-DMAC7.html) |
| TW (1) | TW201406741A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013156200A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160208097A1 (en) | 2015-01-15 | 2016-07-21 | Rohm And Haas Electronic Materials Llc | Polyimide compositions and methods |
| JP6750146B2 (ja) * | 2015-10-13 | 2020-09-02 | 株式会社ピーアイ技術研究所 | 電着用ポリイミド及びそれを含む電着塗料組成物 |
| CN109575019B (zh) * | 2018-12-26 | 2020-04-14 | 苏州闻智生物科技有限公司 | 一种5-溴-7-氮杂吲哚的制备方法 |
| CN117304149B (zh) * | 2023-09-28 | 2025-12-12 | 常州市尚科新材料有限公司 | 4-苯乙炔苯酐的合成方法 |
| CN119506538A (zh) * | 2024-11-18 | 2025-02-25 | 马鞍山钢铁股份有限公司 | 一种取向硅钢酸洗卷及其制备方法、取向硅钢成品 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956322A (en) | 1975-03-14 | 1976-05-11 | General Electric Company | Dianhydrides of bis-(orthodicarboxyphenyloxyphenyl)acetylene and bis-(ortho-dicarboxyphenyloxyphenyl)2,2-dichloroethylene |
| US3983093A (en) | 1975-05-19 | 1976-09-28 | General Electric Company | Novel polyetherimides |
| US4973707A (en) | 1989-07-31 | 1990-11-27 | General Electric Company | Acetylene bis-phthalic compounds and polyimides made therefrom |
| DE3936297A1 (de) | 1989-11-01 | 1991-05-02 | Bayer Ag | Verfahren zur herstellung von symmetrischen diarylacetylenen |
| US5567800A (en) | 1994-10-28 | 1996-10-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Imide oligomers endcapped with phenylethynyl phthalic anhydrides and polymers therefrom |
| JPH11180970A (ja) * | 1997-12-17 | 1999-07-06 | Mitsui Chem Inc | 炭素炭素三重結合を有するジカルボン酸無水物の製造方法 |
| JP4913962B2 (ja) * | 2001-08-30 | 2012-04-11 | マナック株式会社 | フェニルエチニルフタル酸無水物誘導体の製造方法 |
| JP4299521B2 (ja) * | 2002-09-30 | 2009-07-22 | 富士フイルム株式会社 | エチニル基を有する無水フタル酸化合物およびその製造方法 |
| JP4574403B2 (ja) * | 2004-03-25 | 2010-11-04 | 富士フイルム株式会社 | アリールエチニルフタル酸誘導体及び該誘導体の製造方法 |
| US7015304B1 (en) * | 2004-07-23 | 2006-03-21 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Solvent free low-melt viscosity imide oligomers and thermosetting polyimide composites |
| CN1312145C (zh) * | 2004-08-03 | 2007-04-25 | 上海市合成树脂研究所 | 4－苯乙炔苯酐的制备方法 |
| JP2006151903A (ja) * | 2004-11-30 | 2006-06-15 | Fuji Photo Film Co Ltd | エチニルフタル酸無水物誘導体及びエチニルフタル酸誘導体の製造方法 |
| CN101550121A (zh) * | 2008-04-01 | 2009-10-07 | 四川大学 | 由4-溴邻苯二甲酸制备4-苯乙炔邻苯二甲酸酐的方法 |
| JP5485890B2 (ja) * | 2008-07-31 | 2014-05-07 | マナック株式会社 | 無水フタル酸誘導体の製造方法 |
| CN102844291B (zh) | 2010-04-16 | 2015-06-17 | 聂克斯姆化学有限公司 | 新型交联剂 |
| EP2569343B1 (en) * | 2010-05-14 | 2015-07-08 | Nexam Chemical AB | Catalysis of cross-linking |
| WO2012131063A1 (en) | 2011-04-01 | 2012-10-04 | Nexam Chemical Ab | Improved oligo- and polyimides |
-
2012
- 2012-04-20 EP EP12164900.8A patent/EP2653467B1/en active Active
- 2012-04-20 ES ES12164900.8T patent/ES2523824T3/es active Active
-
2013
- 2013-03-08 KR KR1020147032487A patent/KR102081717B1/ko active Active
- 2013-03-08 CN CN201380020284.4A patent/CN104245685B/zh active Active
- 2013-03-08 RU RU2014145135A patent/RU2014145135A/ru unknown
- 2013-03-08 JP JP2015506134A patent/JP6138237B2/ja active Active
- 2013-03-08 US US14/394,489 patent/US9018401B2/en active Active
- 2013-03-08 WO PCT/EP2013/054686 patent/WO2013156200A1/en not_active Ceased
- 2013-04-19 TW TW102113926A patent/TW201406741A/zh unknown
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