FR2473528A1 - Procede pour eviter la cristallisation des n,n' diphenylene bis imides dans les compositions thermodurcissables en contenant - Google Patents
Procede pour eviter la cristallisation des n,n' diphenylene bis imides dans les compositions thermodurcissables en contenant Download PDFInfo
- Publication number
- FR2473528A1 FR2473528A1 FR8000369A FR8000369A FR2473528A1 FR 2473528 A1 FR2473528 A1 FR 2473528A1 FR 8000369 A FR8000369 A FR 8000369A FR 8000369 A FR8000369 A FR 8000369A FR 2473528 A1 FR2473528 A1 FR 2473528A1
- Authority
- FR
- France
- Prior art keywords
- bis
- imide
- maleimide
- formula
- toluene
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 15
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 9
- 150000003949 imides Chemical class 0.000 title claims description 6
- 238000002425 crystallisation Methods 0.000 title claims description 4
- 230000008025 crystallization Effects 0.000 title claims description 4
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 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 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000746 allylic group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 241001125843 Trichiuridae Species 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 16
- 239000011347 resin Substances 0.000 abstract description 16
- 238000005266 casting Methods 0.000 abstract description 3
- 238000005470 impregnation Methods 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000004642 Polyimide Substances 0.000 abstract 1
- 229920001721 polyimide Polymers 0.000 abstract 1
- 238000001816 cooling Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002671 adjuvant Substances 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- AJBQAIDJQOJYFQ-UHFFFAOYSA-N methane;pyrrole-2,5-dione Chemical compound C.O=C1NC(=O)C=C1.O=C1NC(=O)C=C1 AJBQAIDJQOJYFQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000003254 radicals Chemical class 0.000 description 2
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 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
- -1 dimethylacryl ester Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 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
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000002348 vinylic group Chemical group 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)
Priority Applications (8)
| 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 |
| EP80401838A EP0032644B1 (fr) | 1980-01-09 | 1980-12-22 | Procédé pour éviter la cristallisation des N-N' diphénylène bis-imides dans les compositions thermodurcissables en contenant |
| DE8080401838T DE3066445D1 (en) | 1980-01-09 | 1980-12-22 | Process to avoid crystallisation of n-n' diphenylene bis imides in heat-curable compositions containing them |
| JP56000184A 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 |
| IE20/81A IE50803B1 (en) | 1980-01-09 | 1981-01-07 | Process for preventing the crystallisation of n,n'-diphenylene-bis-imides in thermosetting compositions in which they are present |
| CA000368138A CA1156796A (fr) | 1980-01-09 | 1981-01-08 | Procede pour eviter la cristallisation des n,n' diphenylene bis-imides dans les compositions thermodurcissables en contenant |
| DK5981A DK149899C (da) | 1980-01-09 | 1981-01-08 | Fremgangsmaade til fremstilling af termohaerdelige formstoffer paa basis af n,n'-diphenylen-bis-maleimider |
| US06/232,253 US4413107A (en) | 1980-01-09 | 1981-02-06 | Imido thermosetting compositions storage-stabilized against recrystallization of bis-imides therefrom |
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 |
|---|---|
| FR2473528A1 true FR2473528A1 (fr) | 1981-07-17 |
| FR2473528B1 FR2473528B1 (OSRAM) | 1984-11-16 |
Family
ID=9237355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8000369A Granted 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 |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1948841A1 (de) * | 1968-09-27 | 1970-04-30 | Tokyo Shibaura Electric Co | Waermebestaendige Harzzusammensetzungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1948841A1 (de) * | 1968-09-27 | 1970-04-30 | Tokyo Shibaura Electric Co | Waermebestaendige Harzzusammensetzungen |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1156796A (fr) | 1983-11-08 |
| JPS5856562B2 (ja) | 1983-12-15 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |