JPS6324003B2 - - Google Patents
Info
- Publication number
- JPS6324003B2 JPS6324003B2 JP14205679A JP14205679A JPS6324003B2 JP S6324003 B2 JPS6324003 B2 JP S6324003B2 JP 14205679 A JP14205679 A JP 14205679A JP 14205679 A JP14205679 A JP 14205679A JP S6324003 B2 JPS6324003 B2 JP S6324003B2
- Authority
- JP
- Japan
- Prior art keywords
- anhydride
- formula
- imide
- compound
- ethylenically unsaturated
- 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 imide compound Chemical class 0.000 claims description 33
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 6
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 3
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- ZGNVVBYRELJWOC-UHFFFAOYSA-N aniline furan-2,5-dione Chemical compound C1(C=C/C(=O)O1)=O.NC1=CC=CC=C1 ZGNVVBYRELJWOC-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical class C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Epoxy Resins (AREA)
- Indole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14205679A JPS5667326A (en) | 1979-11-05 | 1979-11-05 | Imide type compound and production thereof |
| EP80106787A EP0028419A3 (en) | 1979-11-05 | 1980-11-04 | Imides and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14205679A JPS5667326A (en) | 1979-11-05 | 1979-11-05 | Imide type compound and production thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17697887A Division JPS6388178A (ja) | 1987-07-17 | 1987-07-17 | イミド系化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5667326A JPS5667326A (en) | 1981-06-06 |
| JPS6324003B2 true JPS6324003B2 (https=) | 1988-05-19 |
Family
ID=15306382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14205679A Granted JPS5667326A (en) | 1979-11-05 | 1979-11-05 | Imide type compound and production thereof |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0028419A3 (https=) |
| JP (1) | JPS5667326A (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56161457A (en) * | 1980-05-17 | 1981-12-11 | Kanegafuchi Chem Ind Co Ltd | Heat-resisting resin composition |
| DE3478116D1 (en) * | 1984-06-26 | 1989-06-15 | Toray Industries | A method for preparing polyimide prepolymers |
| KR100729015B1 (ko) * | 2000-01-04 | 2007-06-14 | 어섹스 팔마큐티칼스 인코포레이티드 | Ｎ,ｏ-아미도말로네이트 백금 착화합물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878172A (en) * | 1968-12-19 | 1975-04-15 | Rhone Poulenc Sa | Process for preparing heat resistant resin from unsaturated bis-imide and diamine |
| GB1395761A (en) * | 1971-03-18 | 1975-05-29 | Gen Electric | Process for making polyimide prepolymer and product produced thereby |
| FR2142741B1 (https=) * | 1971-06-24 | 1973-06-29 | Rhone Poulenc Sa | |
| FR2142740B1 (https=) * | 1971-06-24 | 1973-06-29 | Rhone Poulenc Sa | |
| CA978691A (en) * | 1971-07-12 | 1975-11-25 | Eugene A. Burns | Polyimides and methods of producing same |
| US3842143A (en) * | 1972-11-02 | 1974-10-15 | Ciba Geigy Corp | Processable polyimides and polyamideimides containing polyolefinic unsaturated imides |
| FR2303836A1 (fr) * | 1975-03-10 | 1976-10-08 | Rhone Poulenc Ind | Polymeres a groupement imide comportant un polyester exempt d'insaturation aliphatique |
| CH615935A5 (https=) * | 1975-06-19 | 1980-02-29 | Ciba Geigy Ag |
-
1979
- 1979-11-05 JP JP14205679A patent/JPS5667326A/ja active Granted
-
1980
- 1980-11-04 EP EP80106787A patent/EP0028419A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5667326A (en) | 1981-06-06 |
| EP0028419A2 (en) | 1981-05-13 |
| EP0028419A3 (en) | 1981-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS59139358A (ja) | 単量体化合物およびその製造方法 | |
| JPS6324003B2 (https=) | ||
| JPH01294662A (ja) | ポリマレイミド化合物およびその製造方法 | |
| CN117466850B (zh) | 一种4-苯基乙炔基邻苯二甲酸酐的制备方法 | |
| JPS5851955B2 (ja) | ５−（２，５−ジオキソテトラヒドロ−３−フラニル）−３−メチル−３−シクロヘキセン−１，２−ジカルボン酸無水物 | |
| WO1987003871A1 (fr) | Composes aromatiques de bismaleimido et procede de preparation | |
| JPS6143339B2 (https=) | ||
| JPS5952660B2 (ja) | ポリマレイミドの製造方法 | |
| CA2062538A1 (en) | Aromatic trisanhydrides | |
| JPS6388178A (ja) | イミド系化合物 | |
| JPH0623196B2 (ja) | 末端二重結合を有するジアセチレン基含有イミド化合物 | |
| JP2844878B2 (ja) | エーテル基を有するマレイミド樹脂の製造方法 | |
| CN116239790B (zh) | 基于呋喃二甲酸的羧基封端超支化聚酰胺、其制法与应用 | |
| JP3551493B2 (ja) | 新規ビスオキサゾリン化合物 | |
| JPS6366164A (ja) | ビスマレイミド類の製造方法 | |
| JPH0649025A (ja) | ナフタレン環含有不飽和イミド化合物 | |
| JPS5921868B2 (ja) | 重合性多マレイミド化合物の製法 | |
| JPS6183158A (ja) | Ｎ，Ｎ′−ｍ−フエニレンビスマレイミドの製造方法 | |
| JPH01211562A (ja) | 新規なビスマレイミド化合物及びその製造法 | |
| JPH047369B2 (https=) | ||
| JPH0717600B2 (ja) | ビスマレイミド化合物およびその製造方法 | |
| JPS6333495B2 (https=) | ||
| JPH0578555B2 (https=) | ||
| JPS62167760A (ja) | ビスマレイミドおよびその製造方法 | |
| JPH0446155A (ja) | ４―（ヒドロキシフェノキシ）フェニルマレイミドおよびその製造方法 |