CA1110394A - Epoxide resin mixtures - Google Patents
Epoxide resin mixturesInfo
- Publication number
- CA1110394A CA1110394A CA280,575A CA280575A CA1110394A CA 1110394 A CA1110394 A CA 1110394A CA 280575 A CA280575 A CA 280575A CA 1110394 A CA1110394 A CA 1110394A
- Authority
- CA
- Canada
- Prior art keywords
- contain
- mixtures according
- formula
- epoxide
- alkenyl
- 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 abstract description 53
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 18
- 239000003822 epoxy resin Substances 0.000 title claims description 10
- -1 epoxide compounds Chemical class 0.000 claims abstract description 28
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 24
- 150000002170 ethers Chemical class 0.000 claims abstract description 11
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000004642 Polyimide Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229920001721 polyimide Polymers 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229930185605 Bisphenol Natural products 0.000 claims description 10
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 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 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920006037 cross link polymer Polymers 0.000 claims description 3
- 125000005462 imide group Chemical group 0.000 claims description 3
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000005770 Eugenol Substances 0.000 claims description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 229960002217 eugenol Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000008379 phenol ethers Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 claims 2
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 claims 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 11
- 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 10
- 239000000047 product Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
- 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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- MBUAAMOJATXYKR-UHFFFAOYSA-N 4-bis(4-aminophenoxy)phosphinothioyloxyaniline Chemical compound C1=CC(N)=CC=C1OP(=S)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 MBUAAMOJATXYKR-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- ZYPZVOKVDNSKLP-UHFFFAOYSA-N tris(4-aminophenyl) phosphate Chemical compound C1=CC(N)=CC=C1OP(=O)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 ZYPZVOKVDNSKLP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH774676A CH621810A5 (en, 2012) | 1976-06-17 | 1976-06-17 | |
| CH7746/76 | 1976-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1110394A true CA1110394A (en) | 1981-10-06 |
Family
ID=4329853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA280,575A Expired CA1110394A (en) | 1976-06-17 | 1977-06-15 | Epoxide resin mixtures |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4127615A (en, 2012) |
| JP (1) | JPS52154896A (en, 2012) |
| CA (1) | CA1110394A (en, 2012) |
| CH (1) | CH621810A5 (en, 2012) |
| DE (1) | DE2726846C2 (en, 2012) |
| FR (1) | FR2355047A1 (en, 2012) |
| GB (1) | GB1548318A (en, 2012) |
| IT (1) | IT1082105B (en, 2012) |
| NL (1) | NL184010C (en, 2012) |
| ZA (1) | ZA773607B (en, 2012) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5341399A (en) * | 1976-09-28 | 1978-04-14 | Toshiba Corp | Heat resistant resin composition |
| US4288359A (en) * | 1977-11-04 | 1981-09-08 | E. I. Du Pont De Nemours And Company | Epoxy imide compositions |
| US4296219A (en) * | 1978-03-31 | 1981-10-20 | Hitachi, Ltd. | Bismide-ether compounds, compositions thereof, and method of producing same |
| JPS54155297A (en) * | 1978-05-30 | 1979-12-07 | Toshiba Corp | Resin composition |
| JPS5536212A (en) * | 1978-09-06 | 1980-03-13 | Mitsui Toatsu Chem Inc | Thermosetting resin composition |
| US4269953A (en) * | 1979-04-02 | 1981-05-26 | General Dynamics Corporation | Method of crosslinking aromatic thermoplastic polymers using a biphenylene terminated compound |
| US4294877A (en) * | 1979-04-05 | 1981-10-13 | E. I. Du Pont De Nemours And Company | Epoxy imide compositions |
| US4294743A (en) * | 1979-04-05 | 1981-10-13 | E. I. Du Pont De Nemours And Company | Epoxy imide |
| US4384128A (en) * | 1981-04-03 | 1983-05-17 | E. I. Du Pont De Nemours And Company | Perfluoroglycidyl ethers |
| US4363898A (en) * | 1981-04-03 | 1982-12-14 | E. I. Du Pont De Nemours And Company | Perfluorodiglycidyl ethers |
| US4377705A (en) * | 1981-04-03 | 1983-03-22 | E. I. Du Pont De Nemours And Company | Perfluorodiglycidyl ethers and precursors therefor |
| US4360645A (en) * | 1981-04-03 | 1982-11-23 | E. I. Du Pont De Nemours And Company | Perfluoroglycidyl ethers |
| JPS5827713A (ja) * | 1981-08-12 | 1983-02-18 | Japan Atom Energy Res Inst | 重合体組成物 |
| CH647249A5 (de) * | 1981-12-23 | 1985-01-15 | Ciba Geigy Ag | Lagerstabile, waermehaertbare, einen polymerisationskatalysator enthaltende mischungen auf polyimidbasis. |
| US4552935A (en) * | 1983-01-13 | 1985-11-12 | Ciba-Geigy Corporation | Heat-curable epoxy resin mixtures containing imide compounds and condensation products of phenols, amines and aldehydes or ketones |
| CA1229196A (en) * | 1983-07-18 | 1987-11-10 | General Electric Company | Polyimide molding compositions |
| US4579916A (en) * | 1983-11-15 | 1986-04-01 | Ciba-Geigy Corporation | Curable mixtures containing an epoxide resin, an imide and a curing catalyst |
| CA1245726A (en) * | 1984-01-19 | 1988-11-29 | Francis A. L'esperance | Laser incisional device |
| JPS60252628A (ja) * | 1984-05-28 | 1985-12-13 | Mitsui Petrochem Ind Ltd | 熱硬化性樹脂組成物 |
| US4692272A (en) * | 1984-10-15 | 1987-09-08 | Stauffer Chemical Company | Thermally stable adhesive comprising soluble polyimide resin and epoxy resin |
| ATE34570T1 (de) * | 1985-02-01 | 1988-06-15 | Ciba Geigy Ag | (acylthiopropyl)-polyphenole. |
| EP0204659B1 (de) * | 1985-06-06 | 1991-11-21 | Ciba-Geigy Ag | Polyepoxide und deren Verwendung |
| US4652398A (en) * | 1985-09-12 | 1987-03-24 | Stauffer Chemical Company | Rapid curing, thermally stable adhesive composition comprising epoxy resin, polyimide, reactive solvent, and crosslinker |
| EP0225174A3 (en) * | 1985-11-26 | 1989-04-12 | Sumitomo Chemical Company, Limited | Thermosetting resin composition and a composite material comprising the cured product of the resin composition as its matrix |
| US4826927A (en) * | 1986-01-13 | 1989-05-02 | Ciba-Geigy Corporation | Mixtures containing polymides alkenyphenols and either epoxide group-free adducts or another polyimide |
| JPS62207354A (ja) * | 1986-03-07 | 1987-09-11 | Sumitomo Chem Co Ltd | 熱硬化性樹脂組成物 |
| JPS6335014U (en, 2012) * | 1986-08-25 | 1988-03-07 | ||
| US4740330A (en) * | 1986-09-03 | 1988-04-26 | The Dow Chemical Company | Method for allylating aromatic hydroxyl-containing compounds |
| US4808717A (en) * | 1986-09-17 | 1989-02-28 | Sumitomo Chemical Company, Limited | Thermosetting resin composition |
| US4902778A (en) * | 1988-02-18 | 1990-02-20 | Basf Aktiengesellschaft | Propenylphenoxy-terminated oligomeric tougheners and their use in toughening thermosetting bismaleimide resin compositions |
| US4923928A (en) * | 1988-02-18 | 1990-05-08 | Basf Aktiengesellschaft | Thermosetting bismaleimide resin composition containing an adduct of a propenylphenol and an epoxy compound |
| US5003018A (en) * | 1988-04-29 | 1991-03-26 | Basf Aktiengesellschaft | Slurry mixing of bismaleimide resins |
| US5189128A (en) * | 1988-06-20 | 1993-02-23 | Ciba-Geigy Corporation | Solution stable polyimide resin systems |
| US5183865A (en) * | 1988-12-27 | 1993-02-02 | Ford Motor Company | Thermosettable powder compositions of polymaleimide and allyl-functional prepolymer |
| US5037689A (en) * | 1989-02-17 | 1991-08-06 | Basf Aktiengesellschaft | Toughened thermosetting structural materials |
| US4975221A (en) * | 1989-05-12 | 1990-12-04 | National Starch And Chemical Investment Holding Corporation | High purity epoxy formulations for use as die attach adhesives |
| US4988785A (en) * | 1989-06-30 | 1991-01-29 | Allied-Signal | Bismaleimide resin based on indane bisphenol |
| JP2524011B2 (ja) * | 1991-05-23 | 1996-08-14 | 株式会社日立製作所 | 高圧コイル注型用熱硬化性樹脂組成物、該組成物で注型、硬化してなるモ―ルドコイル、パネル |
| US5637387A (en) * | 1991-06-03 | 1997-06-10 | Ciba-Geigy Corporation | Storage-stable advanced polymaleimide compositions |
| US5290882A (en) * | 1991-08-13 | 1994-03-01 | Shin-Etsu Chemical Co., Ltd. | Thermosetting resin compositions |
| JP2669247B2 (ja) * | 1992-02-13 | 1997-10-27 | 信越化学工業株式会社 | 熱硬化性樹脂組成物 |
| WO2000029210A1 (fr) * | 1998-11-18 | 2000-05-25 | Daikin Industries, Ltd. | Structure polymere contenant du fluor a adhesivite haute temperature, et materiau de glissement utilisant ladite structure |
| JP2001164091A (ja) * | 1999-12-13 | 2001-06-19 | Japan Epoxy Resin Kk | エポキシ樹脂組成物 |
| AU2003301550A1 (en) * | 2002-10-22 | 2004-05-13 | Henkel Corporation | Co-curable compositions |
| ATE346877T1 (de) * | 2003-04-16 | 2006-12-15 | Huntsman Adv Mat Switzerland | Härtungsbeschleuniger für epoxyharzzusammensetzungen härtend bei niedriger temperatur |
| DE102022202880A1 (de) | 2022-03-24 | 2023-09-28 | Siemens Aktiengesellschaft | Pulverlackformulierung zur Isolation des Wickelkopfes einer elektrischen rotierenden Maschine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125349C (en, 2012) * | 1965-02-04 | 1900-01-01 | ||
| JPS4912600B1 (en, 2012) * | 1970-05-13 | 1974-03-26 | ||
| FR2142742B1 (en, 2012) * | 1971-06-24 | 1974-04-26 | Rhone Poulenc Sa | |
| DE2118690A1 (de) * | 1971-04-17 | 1973-02-01 | Reichhold Albert Chemie Ag | Verfahren zur herstellung von polyimiden |
| FR2142741B1 (en, 2012) * | 1971-06-24 | 1973-06-29 | Rhone Poulenc Sa | |
| US4005154A (en) * | 1971-06-24 | 1977-01-25 | Rhone-Poulenc S.A. | Curing 1,2-epoxy with prepolymer based on polyamines and oligomers possessing imide groups |
| FR2201313B1 (en, 2012) * | 1972-10-02 | 1975-01-03 | Rhone Poulenc Sa | |
| FR2204655B1 (en, 2012) * | 1972-10-31 | 1976-01-30 | Rhone Poulenc Ind Fr | |
| US3962182A (en) * | 1972-11-21 | 1976-06-08 | Aerojet-General Corporation | Imide oxirane reactions |
| JPS5129760B2 (en, 2012) * | 1973-06-06 | 1976-08-27 | ||
| JPS5216515B2 (en, 2012) * | 1973-11-14 | 1977-05-10 | ||
| US3920768A (en) * | 1974-01-14 | 1975-11-18 | Union Carbide Corp | Arylimide-epoxy resin composites |
| FR2259860B1 (en, 2012) * | 1974-02-04 | 1976-12-03 | Rhone Poulenc Ind | |
| JPS535920B2 (en, 2012) * | 1974-06-03 | 1978-03-02 |
-
1976
- 1976-06-17 CH CH774676A patent/CH621810A5/de not_active IP Right Cessation
-
1977
- 1977-06-06 US US05/803,498 patent/US4127615A/en not_active Expired - Lifetime
- 1977-06-14 DE DE2726846A patent/DE2726846C2/de not_active Expired
- 1977-06-15 CA CA280,575A patent/CA1110394A/en not_active Expired
- 1977-06-16 GB GB25206/77A patent/GB1548318A/en not_active Expired
- 1977-06-16 IT IT24760/77A patent/IT1082105B/it active
- 1977-06-16 FR FR7718453A patent/FR2355047A1/fr active Granted
- 1977-06-16 NL NLAANVRAGE7706650,A patent/NL184010C/xx not_active IP Right Cessation
- 1977-06-16 ZA ZA00773607A patent/ZA773607B/xx unknown
- 1977-06-17 JP JP7197077A patent/JPS52154896A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2355047A1 (fr) | 1978-01-13 |
| CH621810A5 (en, 2012) | 1981-02-27 |
| FR2355047B1 (en, 2012) | 1980-04-18 |
| NL7706650A (nl) | 1977-12-20 |
| NL184010C (nl) | 1989-03-16 |
| JPS52154896A (en) | 1977-12-22 |
| IT1082105B (it) | 1985-05-21 |
| GB1548318A (en) | 1979-07-11 |
| JPS5728416B2 (en, 2012) | 1982-06-16 |
| DE2726846A1 (de) | 1977-12-29 |
| US4127615A (en) | 1978-11-28 |
| DE2726846C2 (de) | 1986-09-11 |
| ZA773607B (en) | 1978-05-30 |
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