GB1277790A - Resin forming compositions containing maleimide and bismaleimide derivatives - Google Patents
Resin forming compositions containing maleimide and bismaleimide derivativesInfo
- Publication number
- GB1277790A GB1277790A GB4493269A GB4493269A GB1277790A GB 1277790 A GB1277790 A GB 1277790A GB 4493269 A GB4493269 A GB 4493269A GB 4493269 A GB4493269 A GB 4493269A GB 1277790 A GB1277790 A GB 1277790A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- maleimide
- maleic anhydride
- peroxide
- formulμ
- 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 abstract 3
- 229920005989 resin Polymers 0.000 title abstract 2
- 239000011347 resin Substances 0.000 title abstract 2
- 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 title 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- -1 maleimide compound Chemical class 0.000 abstract 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 abstract 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 abstract 1
- CJENYVWFVWQVPS-UHFFFAOYSA-N 1-(3-nitrophenyl)pyrrole-2,5-dione Chemical class [O-][N+](=O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 CJENYVWFVWQVPS-UHFFFAOYSA-N 0.000 abstract 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract 1
- UNTJKLFCBQDRMZ-UHFFFAOYSA-N 3-(2,5-dioxo-1-phenylpyrrol-3-yl)oxy-1-phenylpyrrole-2,5-dione Chemical compound O(C=1C(=O)N(C(C1)=O)C1=CC=CC=C1)C=1C(=O)N(C(C1)=O)C1=CC=CC=C1 UNTJKLFCBQDRMZ-UHFFFAOYSA-N 0.000 abstract 1
- BTUZQYJLOSUOAV-UHFFFAOYSA-N 3-[(2,5-dioxo-1-phenylpyrrol-3-yl)methyl]-1-phenylpyrrole-2,5-dione Chemical compound O=C1N(C=2C=CC=CC=2)C(=O)C=C1CC(C1=O)=CC(=O)N1C1=CC=CC=C1 BTUZQYJLOSUOAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical class C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229920006015 heat resistant resin Polymers 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 229930004008 p-menthane Natural products 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N trans-p-menthane Natural products CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 abstract 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 abstract 1
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/303—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 H01B3/38 or H01B3/302
- H01B3/306—Polyimides or polyesterimides
-
- 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
- C08F22/00—Homopolymers and 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
- C08F22/36—Amides or imides
-
- 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
- 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
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
- C08G73/127—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G73/16—Polyester-imides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
1277790 Maleimide copolymers YOKYO SHIBAURA ELECTRIC CO Ltd 11 Sept 1969 [27 Sept 1968 11 June 1969 30 July 1969] 44932/69 Heading C3P Heat resistant resins are prepared by copolymerizing in the presence of peroxide initiators mixtures comprising at least one maleimide compound and at least one bismaleimide compound of formulµ where R 1 is phenyl, methylphenyl, chlorophenyl, nitrophenyl or -(CH 2 CH 2 ) n CH 3 where n is 1 to 6; R 2 is H or alkyl; and R 3 is 4,4<SP>1</SP>- methylenediphenylene or 4,4<SP>1</SP>-oxydiphenylene; optionally together with (a) an unsaturated polyester resin of formulµ where R 4 is -CH=CH- or -C(CH 3 )=CH-, R 5 is 1,4-cyclohexylene or -(CH 2 CH 2 ) n - and R 6 is p-phenylene or -(CH 2 CH 2 ) n -where n is 1 to 6, or (b) an imide ester of formula where R 2 and R 3 are as defined above and R 7 is the radical of a dihydric alcohol or of n<SP>1</SP> moles of dihydric alcohol esterified with n<SP>1</SP> - 1 moles of dibasic acid. The components may be melted together to form moulding, casting and laminating compositions. Specified peroxides are dicumyl and dibenzyl peroxides, t-butyl perbenzoate and p-menthane peroxide. Many examples are given describing resins obtained by melting together two or more of N-phenyl-, N-3-chlorophenyl- and N-3-nitrophenyl maleimides, methylene-bis-(N-phenyl maleimide) and oxy-bis-(N-phenyl maleimide); optionally with polyesters derived from adipic acid, maleic anhydride and ethylene glycol or dimethyl terephthalate, maleic anhydride and ethylene glycol, or an imide ester derived from p,p<SP>1</SP>- eiaminodiphenylmethane, N-methyl-2-pyrrolidone, maleic anhydride and trimellitic anhydride; and curing in the presence of t-butyl perbenzoate, p-menthane hydroperoxide or dicumyl peroxide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6951568 | 1968-09-27 | ||
| JP4540769A JPS4832187B1 (en) | 1969-06-11 | 1969-06-11 | |
| JP5965169A JPS4832188B1 (en) | 1969-07-30 | 1969-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1277790A true GB1277790A (en) | 1972-06-14 |
Family
ID=27292225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4493269A Expired GB1277790A (en) | 1968-09-27 | 1969-09-11 | Resin forming compositions containing maleimide and bismaleimide derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1948841A1 (en) |
| FR (1) | FR2020542A1 (en) |
| GB (1) | GB1277790A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515962A (en) * | 1982-08-05 | 1985-05-07 | Ciba Geigy Corporation | Allyl or methallyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imides and bisimides |
| US4604437A (en) * | 1984-01-31 | 1986-08-05 | Ciba-Geigy Corporation | Polymer from substituted, unsaturated, bicyclic imide |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2324684A1 (en) * | 1975-09-19 | 1977-04-15 | Rhone Poulenc Ind | THERMOSETTING COMPOSITIONS BASED ON BIS-MALEIMIDE AND N-VINYLPYRROLIDONE-2 |
| FR2473528A1 (en) * | 1980-01-09 | 1981-07-17 | Rhone Poulenc Ind | PROCESS FOR PREVENTING THE CRYSTALLIZATION OF N, N 'DIPHENYLENE BIS IMIDES IN THERMOSETTING COMPOSITIONS CONTAINING |
| WO1989008670A1 (en) * | 1988-03-07 | 1989-09-21 | Aristech Chemical Corporation | Thermosetting composition from maleimide, olefinic monomer and unsaturated polyester |
-
1969
- 1969-09-10 FR FR6930848A patent/FR2020542A1/fr not_active Withdrawn
- 1969-09-11 GB GB4493269A patent/GB1277790A/en not_active Expired
- 1969-09-26 DE DE19691948841 patent/DE1948841A1/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515962A (en) * | 1982-08-05 | 1985-05-07 | Ciba Geigy Corporation | Allyl or methallyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imides and bisimides |
| US4667003A (en) * | 1982-08-05 | 1987-05-19 | Ciba-Geigy Corporation | Crosslinked polymers prepared from allyl or methallyl-bicyclo[2,2,1]hept-5-ene-2,3-dicarboxylic acid imides and bisimides |
| US4604437A (en) * | 1984-01-31 | 1986-08-05 | Ciba-Geigy Corporation | Polymer from substituted, unsaturated, bicyclic imide |
| US4742166A (en) * | 1984-01-31 | 1988-05-03 | Ciba-Geigy Corporation | Substituted, unsaturated, bicyclic imides and polymers thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2020542A1 (en) | 1970-07-17 |
| DE1948841A1 (en) | 1970-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |