JPS5856562B2 - Ｎ，ｎ′−ジフエニレンビスイミドを内在せる熱硬化性組成物中での該イミドの晶出防止方法 - Google Patents
Ｎ，ｎ′−ジフエニレンビスイミドを内在せる熱硬化性組成物中での該イミドの晶出防止方法Info
- Publication number
- JPS5856562B2 JPS5856562B2 JP56000184A JP18481A JPS5856562B2 JP S5856562 B2 JPS5856562 B2 JP S5856562B2 JP 56000184 A JP56000184 A JP 56000184A JP 18481 A JP18481 A JP 18481A JP S5856562 B2 JPS5856562 B2 JP S5856562B2
- Authority
- JP
- Japan
- Prior art keywords
- bisimide
- bismaleimide
- ambient temperature
- thermosetting composition
- combination
- 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
- 239000000203 mixture Substances 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 11
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 8
- 238000002425 crystallisation Methods 0.000 title claims description 4
- 230000008025 crystallization Effects 0.000 title claims description 4
- 150000003949 imides Chemical class 0.000 title description 6
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 25
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 238000000859 sublimation Methods 0.000 claims 1
- 230000008022 sublimation Effects 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000003860 storage Methods 0.000 description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 239000004645 polyester resin Substances 0.000 description 6
- -1 tolylene bismaleimide Chemical compound 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- BAZXQZYWJSBDRG-UHFFFAOYSA-N pyrrole-2,5-dione;toluene Chemical compound CC1=CC=CC=C1.O=C1NC(=O)C=C1.O=C1NC(=O)C=C1 BAZXQZYWJSBDRG-UHFFFAOYSA-N 0.000 description 3
- WFJYXGTWVLVHNK-UHFFFAOYSA-N 3-[6-(2,5-dioxopyrrol-3-yl)-3,5,5-trimethylhexyl]pyrrole-2,5-dione Chemical compound C=1C(=O)NC(=O)C=1CC(C)(C)CC(C)CCC1=CC(=O)NC1=O WFJYXGTWVLVHNK-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/404—Imides, e.g. cyclic imides substituted imides comprising oxygen other than the carboxy oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8000369A FR2473528A1 (fr) | 1980-01-09 | 1980-01-09 | Procede pour eviter la cristallisation des n,n' diphenylene bis imides dans les compositions thermodurcissables en contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56106911A JPS56106911A (en) | 1981-08-25 |
| JPS5856562B2 true JPS5856562B2 (ja) | 1983-12-15 |
Family
ID=9237355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56000184A Expired JPS5856562B2 (ja) | 1980-01-09 | 1981-01-06 | Ｎ，ｎ′−ジフエニレンビスイミドを内在せる熱硬化性組成物中での該イミドの晶出防止方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4413107A (OSRAM) |
| EP (1) | EP0032644B1 (OSRAM) |
| JP (1) | JPS5856562B2 (OSRAM) |
| CA (1) | CA1156796A (OSRAM) |
| DE (1) | DE3066445D1 (OSRAM) |
| DK (1) | DK149899C (OSRAM) |
| FR (1) | FR2473528A1 (OSRAM) |
| IE (1) | IE50803B1 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4520145A (en) * | 1982-07-21 | 1985-05-28 | The Boots Company Plc | Modified thermosetting imide resins with improved fracture toughness |
| DE3481915D1 (de) * | 1983-11-04 | 1990-05-17 | Technochemie Gmbh | Haertbare bisimidharzmischungen. |
| FR2605636B1 (fr) * | 1986-10-24 | 1989-02-24 | Rhone Poulenc Chimie | Polymeres a groupements imides sans diamine et leurs procedes de preparation |
| US5221723A (en) * | 1987-06-23 | 1993-06-22 | Ciba-Geigy Corporation | Thermally stable bisimido copolymerizates |
| CA1307605C (fr) * | 1987-06-23 | 1992-09-15 | Rene Arpin | Polymeres a groupements imides sans diamine et leur procede de preparation |
| US5112924A (en) * | 1987-07-15 | 1992-05-12 | Hercules Incorporated | Bismaleimide compositions containing high glass transition temperature and soluble reactive oligomers and composites prepared therefrom |
| US5260411A (en) * | 1988-04-20 | 1993-11-09 | Polytechnic University | Polyimide resins |
| US5003018A (en) * | 1988-04-29 | 1991-03-26 | Basf Aktiengesellschaft | Slurry mixing of bismaleimide resins |
| FR2672896B1 (fr) * | 1991-02-15 | 1993-06-04 | Aerospatiale Soc Nat Industrielle | Procede de durcissement sous rayonnement ionisant d'une resine bis-maleimide et d'un materiau composite utilisant cette resine. |
| US5932635A (en) * | 1991-07-30 | 1999-08-03 | Cytec Technology Corp. | Tackified prepreg systems |
| US5371173A (en) * | 1992-11-25 | 1994-12-06 | Northwestern University | Poled polymeric nonlinear optical materials |
| IL154576A0 (en) | 2000-08-22 | 2003-09-17 | Cytec Tech Corp | Flexible polymer element as toughening agent in prepregs |
| AU2004297228A1 (en) * | 2003-12-03 | 2005-06-23 | Nektar Therapeutics Al, Corporation | Method of preparing maleimide functionalized polymers |
| CA2597652A1 (en) * | 2005-02-16 | 2006-08-24 | Cytec Technology Corp. | Bismaleimide resin with high temperature thermal stability |
| CA2607652C (en) * | 2005-05-09 | 2013-06-18 | Cytec Technology Corp. | Resin-soluble thermoplastic veil for composite materials |
| GB0717507D0 (en) | 2007-09-07 | 2007-10-17 | Cytec Tech Corp | Composite materials and their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2020542A1 (OSRAM) * | 1968-09-27 | 1970-07-17 | Tokyo Shibaura Electric Co | |
| US4298720A (en) * | 1979-07-23 | 1981-11-03 | Mitsui Toatsu Chemicals Incorporated | Thermosetting resin composition from maleimide compound and alkenyl phenol |
-
1980
- 1980-01-09 FR FR8000369A patent/FR2473528A1/fr active Granted
- 1980-12-22 DE DE8080401838T patent/DE3066445D1/de not_active Expired
- 1980-12-22 EP EP80401838A patent/EP0032644B1/fr not_active Expired
-
1981
- 1981-01-06 JP JP56000184A patent/JPS5856562B2/ja not_active Expired
- 1981-01-07 IE IE20/81A patent/IE50803B1/en not_active IP Right Cessation
- 1981-01-08 CA CA000368138A patent/CA1156796A/fr not_active Expired
- 1981-01-08 DK DK5981A patent/DK149899C/da not_active IP Right Cessation
- 1981-02-06 US US06/232,253 patent/US4413107A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1156796A (fr) | 1983-11-08 |
| FR2473528A1 (fr) | 1981-07-17 |
| JPS56106911A (en) | 1981-08-25 |
| US4413107A (en) | 1983-11-01 |
| DK5981A (da) | 1981-07-10 |
| IE50803B1 (en) | 1986-07-23 |
| IE810020L (en) | 1981-07-09 |
| DK149899C (da) | 1987-05-04 |
| EP0032644B1 (fr) | 1984-02-01 |
| EP0032644A1 (fr) | 1981-07-29 |
| DE3066445D1 (en) | 1984-03-08 |
| FR2473528B1 (OSRAM) | 1984-11-16 |
| DK149899B (da) | 1986-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5856562B2 (ja) | Ｎ，ｎ′−ジフエニレンビスイミドを内在せる熱硬化性組成物中での該イミドの晶出防止方法 | |
| US3876726A (en) | Vinyl ester urethanes | |
| FR2542752A1 (fr) | Compositions de bis-maleimide-epoxy et matieres fibreuses preimpregnees, moulees | |
| JPS5855969B2 (ja) | コウカカノウナエポキシジユシソセイブツ | |
| JPS5871914A (ja) | ポリ（オキサゾリドン／ウレタン）熱硬化性樹脂及びその製造方法 | |
| JPS60250026A (ja) | エポキシ樹脂組成物 | |
| JPH04227913A (ja) | 新規の硬化性組成物 | |
| 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 | |
| US3215586A (en) | Modified epoxidized polybutadiene resin composition | |
| JPS5853916A (ja) | 熱硬化性エポキシド樹脂組成物 | |
| JPS59204613A (ja) | 耐熱性樹脂組成物 | |
| JPH01256535A (ja) | ヒンダードジアミンから製造したイミド基含有熱硬化性プレポリマーの製造方法 | |
| FR2462458A1 (fr) | Composition de resine thermodurcissable a base de maleimides | |
| JPS5946979B2 (ja) | 新規なスルホンアミド化合物重合体の製造方法 | |
| US4004959A (en) | Unsaturated polyester with polyimide-ammonia prepolymers as thermosetting laminate | |
| JPH0826117B2 (ja) | 不飽和ビニルエステル樹脂組成物およびその増粘組成物 | |
| JPS60252653A (ja) | 不飽和ポリエステル樹脂 | |
| Rhodes | Advances in anhydride epoxy systems | |
| JPH07224121A (ja) | 熱硬化性樹脂組成物 | |
| JPS6116918A (ja) | アルコ−ル変性ポリアミドイミド樹脂粉末の製造法 | |
| JPH08295734A (ja) | ポリイミド系樹脂およびその製法 | |
| JPS60147437A (ja) | 樹脂組成物 | |
| JPH0466259B2 (OSRAM) | ||
| JPS62270622A (ja) | 相互侵入性高分子網目状ポリイミドおよびその製造方法 | |
| US3640960A (en) | Stabilized polyimidazopyrrolones compositions and method of preparation |