WO2022113523A1 - Composition de résine époxyde, produit durci et complexe - Google Patents
Composition de résine époxyde, produit durci et complexe Download PDFInfo
- Publication number
- WO2022113523A1 WO2022113523A1 PCT/JP2021/036599 JP2021036599W WO2022113523A1 WO 2022113523 A1 WO2022113523 A1 WO 2022113523A1 JP 2021036599 W JP2021036599 W JP 2021036599W WO 2022113523 A1 WO2022113523 A1 WO 2022113523A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- resin composition
- component
- elastic modulus
- storage elastic
- Prior art date
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 115
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 115
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000010438 heat treatment Methods 0.000 claims abstract description 33
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 14
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims abstract description 6
- 238000003860 storage Methods 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000012298 atmosphere Substances 0.000 claims description 17
- 238000012423 maintenance Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 230000006866 deterioration Effects 0.000 abstract description 17
- 238000001723 curing Methods 0.000 description 20
- 238000012360 testing method Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 12
- 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 11
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- -1 Alkylene glycol Chemical compound 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000004615 ingredient Substances 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
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000007718 adhesive strength test Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000007602 hot air drying Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- WUIQPLSONDMSBW-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(CC)COCC1CO1 WUIQPLSONDMSBW-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- JROOCDXTPKCUIO-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)CCOCC1CO1 JROOCDXTPKCUIO-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- CAYJDIDYXCENIR-UHFFFAOYSA-N 2-[5-(oxiran-2-ylmethoxy)pentoxymethyl]oxirane Chemical compound C1OC1COCCCCCOCC1CO1 CAYJDIDYXCENIR-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CUGPDVWIMLFIQR-UHFFFAOYSA-N 2-methylpropan-2-olate;rubidium(1+) Chemical compound [Rb+].CC(C)(C)[O-] CUGPDVWIMLFIQR-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical group C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000009957 hemming Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
- C08G59/68—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 catalysts used
Definitions
- the present invention relates to epoxy resin compositions, cured products and composites.
- epoxy resin compositions have excellent adhesive strength, sealing properties, high strength, heat resistance, electrical properties, and chemical resistance, and therefore have been excellent in adhesives, sealing agents, potting agents, coating agents, conductive pastes, etc. It has been used for various purposes. However, it is known that many of the above characteristics have temperature dependence, and the characteristics generally deteriorate significantly above the glass transition temperature.
- Japanese Patent Application Laid-Open No. 2006-63154 contains a cured product containing an epoxy compound and an anionic polymerization initiator such as potassium acetate, which can suppress deterioration of characteristics due to heating.
- the resulting epoxy resin composition is disclosed.
- Composition [2] The epoxy resin composition according to [1], wherein the tan ⁇ peak value (25 to 350 ° C.) of the cured product cured by heating in an atmosphere of 120 ° C. for 120 minutes is 0.19 or less.
- the storage elastic modulus maintenance rate 250 ° C storage elastic modulus (GPa) / 25 ° C.
- the compound of the general formula (1) of the component (B) is contained in a ratio of 0.001 to 5.0 mol with respect to 1 mol (total amount) of the epoxy group of the component (A) [5]. ]
- the epoxy resin composition according to. [7] The epoxy resin composition according to [5] or [6], wherein M of the general formula (1) of the component (B) is potassium.
- the epoxy resin composition according to any one of [1] to [7] which does not contain a curing agent for epoxy resin or a curing accelerator for epoxy resin.
- the epoxy resin composition according to any one of [1] to [8] which does not contain a monofunctional epoxy resin.
- the tan ⁇ peak value (25 to 350 ° C.) of the cured product cured by heating for 120 minutes in an atmosphere of 120 ° C. is 0.19 or less, and the storage elastic modulus maintenance rate (storage elastic modulus at 250 ° C. (250 ° C.)
- the present invention comprises an epoxy resin having a glycidyl group bifunctional or higher in one molecule as a component (A), and a polymerization initiator having a butoxy group and an alkali metal in one molecule as a component (B).
- X to Y is used in the meaning which includes the numerical values (X and Y) described before and after it as the lower limit value and the upper limit value, and means "X or more and Y or less”.
- any epoxy resin having two or more functional glycidyl groups in one molecule can be used without particular limitation.
- the component (A) can be used as a liquid or a solid at 25 ° C., but a liquid component (A) is preferably liquid at 25 ° C. from the viewpoint of obtaining handleability.
- the handling property means that the epoxy resin composition has a low viscosity and is easy to apply.
- the component (A) may have two or more glycidyl groups in one molecule, but preferably has two glycidyl groups in one molecule (two glycidyl groups in one molecule). The group is present) is preferred.
- the content (A) is not particularly limited, but for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type, bisphenol AD type epoxy resin and other bisphenol type epoxy resin, hydrided bisphenol type epoxy resin, and the like.
- the commercially available product of the component (A) is not particularly limited, but for example, jER (registered trademark) 828, 1001, 801, 806, 807, 152, 604, 630, 871, YX8000, YX8034, YX4000 (Mitsubishi Chemical Co., Ltd.).
- jER registered trademark
- Epicron registered trademarks 830, 850, 830LVP, 850CRP, 835LV, HP4032D, 703, 720, 726, 820 (manufactured by DIC Corporation)
- EP4920 (manufactured by ADEKA CORPORATION); TEPIC (registered trademark) series (manufactured by Nissan Chemical Industry Co., Ltd.); KF-101, KF-1001, KF-105, X-22-163B, X-22-9002 (Shinetsu Chemical Co., Ltd.) (Manufactured by Kogyo Co., Ltd.); Denacol EX411, 314, 201, 212, 252 (manufactured by Nagase ChemteX Corporation); DER-331, 332, 334, 431, 542 (manufactured by Dow Chemical Co., Ltd.); YH-434, YH-434L (Manufactured by Nippon Steel Sumitomo Chemical Co., Ltd.), etc., but are not limited to these.
- the component (B) according to the present invention is not particularly limited as long as it is a polymerization initiator having a butoxy group and an alkali metal in one molecule.
- it is intended to provide an epoxy resin composition capable of obtaining a cured product having low temperature curability and suppressing deterioration of characteristics due to heating by selecting the component (B) of the present invention among the polymerization initiators.
- the butoxy groups include an n-butoxy group (CH 3 CH 2 CH 2 CH 2 -O-), an isobutoxy group ((CH 3 ) 2 CHCH 2 -O-), and a sec-butoxy group (CH 3 CH 2 ).
- the tert-butoxy group is preferable from the viewpoint of low-temperature curability and further improvement of the effect of suppressing deterioration of characteristics due to heating.
- examples of the component (B) include the polymerization initiator of the general formula (1).
- M represents an alkali metal.
- the alkali metal include lithium, sodium, potassium, rubidium and the like, preferably sodium and potassium, and particularly preferably potassium.
- the component (A) is three-dimensionally crosslinked at the time of curing (for example, by a curing catalyst), but this reaction leaves many uncrosslinked portions. There is a problem that this uncrosslinked portion contributes to a sharp decrease in the storage elastic modulus and leads to a change in the characteristics of the epoxy resin composition due to a temperature change.
- the present invention has found an epoxy resin composition that can obtain a cured product that is less affected by the glass transition point by using the component (B) according to the present invention among the polymerization initiators. The reason why the cured product of the epoxy resin composition is less affected by the glass transition point by the component (B) according to the present invention is not clear, but the component (B) according to the present invention is the component (A) according to the present invention.
- an epoxy resin composition having an extremely small tan ⁇ peak value can be obtained by controlling the polymerization reaction of the above and suppressing or eliminating the rapid decrease in the storage elastic coefficient by reducing the number of uncrosslinked portions.
- the technical scope of the present invention is not limited by the above reasoning.
- the component (B) can further improve low temperature curability, it is preferable to dilute it with an organic solvent having a boiling point of 50 to 150 ° C., and more preferably, an organic substance having a boiling point of 55 to 100 ° C. It is a solvent.
- the organic solvent is not particularly limited, and examples thereof include THF (tetrahydrofuran, boiling point 66 ° C.), n-hexane (boiling point 69 ° C.), 2-methyl-2-propanol (boiling point 83 ° C.), and the like.
- the concentration is not particularly specified, but for example, the component (B) is 1 to 99% by mass, more preferably 5 to 50% by mass.
- component (B) examples include lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, rubidium tert-butoxide and the like, with sodium tert-butoxide and potassium tert-butoxide being particularly preferable. Further, it is potassium tert-butoxide because it is possible to provide an epoxy resin composition capable of obtaining a cured product having low temperature curability and suppressing deterioration of characteristics due to heating. These may be used alone or in combination of two or more.
- the amount of the component (B) added is not particularly limited, but is preferably 0.1 to 20 parts by mass, more preferably 0.3 to 10 parts by mass with respect to 100 parts by mass of the component (A). More preferably, it is 0.5 to 5 parts by mass.
- the amount of the component (B) added is 0.7 with respect to 100 parts by mass of the component (A). It is preferably about 2.8 parts by mass, and particularly preferably more than 0.7 parts by mass and less than 2.8 parts by mass.
- the above-mentioned addition amount means the amount of the active ingredient.
- the compound of the general formula (1) of the component (B) is contained in 0.001 to 5.0 mol. , More preferably 0.003 to 1.0 mol, and particularly preferably 0.003 to 0.5 mol.
- an epoxy resin composition capable of further obtaining a cured product having low temperature curability and capable of suppressing deterioration of characteristics due to heating.
- the addition amount of the compound of the general formula (1) of the component (B) is the amount of the component (A).
- the total amount of the epoxy group (or glycidyl group) is 1 mol, it is preferably 0.01 to 0.05 mol, and more preferably more than 0.01 mol and less than 0.05 mol.
- any additive component can be further contained as long as the characteristics of the epoxy resin composition are not impaired.
- the component include an adhesive improving component such as a filler, a plasticizer, a solvent, a monofunctional epoxy resin, a curing agent for an epoxy resin, a curing accelerator for an epoxy resin, a photoinitiator, and a silane coupling agent, and a dispersant.
- an adhesive improving component such as a filler, a plasticizer, a solvent, a monofunctional epoxy resin, a curing agent for an epoxy resin, a curing accelerator for an epoxy resin, a photoinitiator, and a silane coupling agent, and a dispersant.
- Leveling agents, wetting agents, surfactants such as defoaming agents, antistatic agents, surface lubricants, rust preventives, preservatives, storage stabilizers such as borate esters, leology adjusters, colorants, UV absorbers , Antioxidant and the like may be contained.
- the epoxy resin composition of the present invention does not contain a curing agent for epoxy resin, a curing accelerator for epoxy resin, and a monofunctional epoxy resin.
- the epoxy resin composition does not contain a curing agent for epoxy resin or a curing accelerator for epoxy resin. In a preferred embodiment of the present invention, the epoxy resin composition does not contain a curing agent for epoxy resin and a curing accelerator for epoxy resin.
- the epoxy resin composition does not contain a monofunctional epoxy resin (an epoxy resin in which one glycidyl group is present in one molecule).
- Examples of the filler include organic powder, inorganic powder, metallic powder and the like.
- Examples of the filler of the inorganic powder include silica, glass, alumina, mica, ceramics, silicone rubber powder, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, clay minerals, diatomaceous earth and the like.
- the addition of the inorganic powder is not particularly limited, but is preferably 0.01 to 500 parts by mass, more preferably 0.1 to 300 parts by mass, and particularly preferably 0.1 to 300 parts by mass with respect to 100 parts by mass of the component (A). 3 to 150 parts by mass. These may be used alone or in combination of two or more.
- the silica can be blended for the purpose of adjusting the viscosity of the epoxy resin composition or improving the mechanical strength of the cured product.
- those hydrophobized with organochlorosilanes, polyorganosiloxane, hexamethyldisilazane and the like can be used.
- Specific examples of silica include, for example, trade names Aerosil (registered trademark) R974, R972, R972V, R972CF, R805, R812, R812S, R816, R8200, RY200, RX200, RY200S, R202 and the like (manufactured by Nippon Aerosil Co., Ltd.). Commercially available products can be mentioned. These may be used alone or in combination of two or more.
- Examples of the organic powder include polyethylene, polypropylene, nylon, crosslinked acrylic, crosslinked polystyrene, polyester, polyvinyl alcohol, polyvinyl butyral, and polycarbonate.
- the amount of the organic powder added is preferably 0.01 to 500 parts by mass, more preferably 0.1 to 300 parts by mass, and particularly preferably 3 to 3 parts by mass with respect to 100 parts by mass of the component (A). It is 150 parts by mass. These may be used alone or in combination of two or more.
- the metallic powder is not particularly limited, and examples thereof include gold powder, silver powder, copper powder, nickel powder, palladium powder, tungsten powder, plating powder, and alumina powder.
- the amount of the metallic powder added is preferably 0.01 to 500 parts by mass, more preferably 0.1 to 300 parts by mass, and particularly preferably 3 with respect to 100 parts by mass of the component (A). ⁇ 150 parts by mass. These may be used alone or in combination of two or more.
- the epoxy resin composition of the present invention can be produced by a conventionally known method. For example, a predetermined amount of the component (A), the component (B), and other optional components are blended, and a mixing means such as a mixer such as a planetary mixer is used, preferably at a temperature of 10 to 70 ° C., more preferably. It can be produced by mixing at 20 to 50 ° C., particularly preferably at room temperature (25 ° C.), preferably for 0.1 to 5 hours, more preferably for 30 minutes to 3 hours, and particularly preferably for about 60 minutes.
- a mixing means such as a mixer such as a planetary mixer is used, preferably at a temperature of 10 to 70 ° C., more preferably. It can be produced by mixing at 20 to 50 ° C., particularly preferably at room temperature (25 ° C.), preferably for 0.1 to 5 hours, more preferably for 30 minutes to 3 hours, and particularly preferably for about 60 minutes.
- the epoxy resin composition of the present invention can be suitably used as an adhesive. That is, a complex adhered using the epoxy resin composition of the present invention is also an embodiment of the present invention.
- ⁇ Applying method> As a method for applying the epoxy resin composition of the present invention to a substrate, a known adhesive method is used. For example, methods such as dispensing, spraying, inkjet printing, screen printing, gravure printing, dipping, and spin coating using an automatic coating machine can be used.
- a cured product obtained by curing the epoxy resin composition of the present invention is also an embodiment of the present invention.
- a cured product obtained by heat-curing the epoxy resin composition of the present invention is also a form of the present invention.
- the temperature and time for heating may be as long as they can be sufficiently cured, but for example, at 75 to 160 ° C., for example, 10 seconds to 300 minutes, preferably 20 seconds to 180 minutes, and more preferably 30 seconds to 150 minutes. It is appropriate to heat under the condition of minutes. Preferably, the conditions of 75 to 160 ° C. for 20 seconds to 180 minutes are suitable.
- the main curing may be carried out after preheating at a temperature of 40 to 75 ° C. for 30 to 90 minutes.
- the epoxy resin composition contains an organic solvent (for example, ethanol), the preheating is preferable because the organic solvent can be volatilized.
- the epoxy resin composition of the present invention preferably has a storage elastic modulus of 5% or more, more preferably 5 to 99%, and even more preferably 5 to 99%, from the viewpoint of less deterioration of characteristics due to heating. It is 7 to 95%, particularly preferably 10 to 80%. That is, in a preferred embodiment of the present invention, the epoxy resin composition has a storage elastic modulus retention rate (250 ° C. storage elastic modulus (GPa) / 25 ° C.) of the cured product cured by heating in an atmosphere of 120 ° C. for 120 minutes.
- the storage elastic modulus (GPa) ⁇ 100) is 5% or more (more preferably 5 to 99%, still more preferably 7 to 95%, particularly preferably 10 to 80%).
- the storage elastic modulus retention rate of the epoxy resin composition adopts the value measured according to the following method. Specifically, the test method is as follows.
- the epoxy resin composition of the present invention was preheated in an atmosphere of 70 ° C. for 60 minutes and then heated in an atmosphere of 120 ° C. for 120 minutes to be cured to obtain a strip-shaped test piece of 10 mm ⁇ 50 mm ⁇ 0.5 mm. rice field.
- This test piece was measured using a dynamic viscoelasticity measuring device DMS6100 (manufactured by Hitachi High-Tech Science Co., Ltd.) in a tensile mode with a temperature range of 25 to 350 ° C., a heating rate of 5 ° C./min, and a frequency of 1 Hz.
- the storage elastic modulus E'(GPa) at 25 ° C. and the storage elastic modulus E'(GPa) at 250 ° C. were measured, and the storage elastic modulus maintenance rate (%) was determined by the following formula.
- Storage elastic modulus maintenance rate (%) (Storage modulus E'at 250 ° C / storage elastic modulus E'at 25 ° C) x 100
- the epoxy resin composition of the present invention preferably has a tan ⁇ peak value of 0.19 or less, more preferably 0.18 or less, and particularly preferably 0.14, from the viewpoint of less deterioration of characteristics due to heating. It is as follows. That is, in a preferred embodiment of the present invention, the epoxy resin composition has a tan ⁇ peak value (25 to 350 ° C.) of 0.19 or less (more preferably) of the cured product cured by heating in an atmosphere of 120 ° C. for 120 minutes. Is 0.18 or less, particularly preferably 0.14 or less). Since the lower the tan ⁇ peak value is, the more preferable it is, the lower limit is not particularly limited, and it is usually more than 0, but for example, it is more than 0.02, preferably 0.05 or more.
- the tan ⁇ peak value of the epoxy resin composition adopts the value measured according to the following method. Specifically, the test method is as follows.
- the epoxy resin composition of the present invention was preheated in an atmosphere of 70 ° C. for 60 minutes and then heated in an atmosphere of 120 ° C. for 120 minutes to be cured to obtain a strip-shaped test piece of 10 mm ⁇ 50 mm ⁇ 0.5 mm. rice field.
- This test piece was measured using a dynamic viscoelasticity measuring device DMS6100 (manufactured by Hitachi High-Tech Science Co., Ltd.) in a tensile mode with a temperature range of 25 to 350 ° C., a heating rate of 5 ° C./min, and a frequency of 1 Hz.
- the tan ⁇ peak value in the temperature range of 25 to 350 ° C. was calculated.
- a cured product that is less affected by the glass transition point means that the tan ⁇ peak value is 0.19 or less. Further, the smaller the tan ⁇ peak value, the less the deterioration of physical properties due to heating. Specifically, the tan ⁇ peak value is preferably 0.18 or less, and more preferably 0.14 or less.
- the tan ⁇ peak value (25 to 350 ° C.) of the cured product cured by heating in an atmosphere of 120 ° C. for 120 minutes is 0.19 or less, and the storage elastic modulus maintenance rate (250 ° C.) is maintained.
- the present invention relates to a cured product obtained by curing the epoxy resin composition of the present invention, which has a storage elastic modulus (GPa) / 25 ° C. storage elastic modulus (GPa) ⁇ 100) of 5% or more.
- reaction start temperature by differential scanning calorimetry is preferably 75 to 160 ° C., more preferably.
- the temperature is 80 to 140 ° C, particularly preferably 85 to 120 ° C.
- the value measured according to the following method is adopted as the reaction start temperature by the differential scanning calorimetry of the epoxy resin composition.
- the test method is as follows.
- the reaction start temperature was measured using differential scanning calorimetry (DSC).
- DSC differential scanning calorimetry
- a DSC110 manufactured by Seiko Instruments Inc. was used for the DSC measurement, and the temperature was raised from 30 to 200 ° C. at a heating rate of 10 ° C./min under a nitrogen atmosphere.
- the reaction start temperature was defined as the temperature at the intersection of the baseline of the graph of the DSC measurement result and the tangent at the inflection of the peak.
- the epoxy resin composition of the present invention can be used in various fields (for example, as an adhesive) such as an automobile field, a railroad vehicle field, an aerospace field, an electric / electronic component field, a construction field, and a civil engineering field, but is preferable. , In the automotive field.
- Adhesive applications in the automobile field are not particularly limited, but may include caulking (hemming) adhesion for fixing the outer panel and the inner panel, and more specifically, panels constituting automobile doors, pillars, and roofs. Adhesion, adhesion between the body and the roof, etc.
- ⁇ Ingredient (A)> a1 Bisphenol A type diglycidyl ether having an epoxy equivalent of 189 (jER (registered trademark) 828 manufactured by Mitsubishi Chemical Corporation, liquid at 25 ° C., having bifunctional glycidyl group in one molecule)
- a'1 Monoglycidyl phenyl ether (molecular weight 150) (reagent) (having one functional glycidyl group in one molecule)
- b1 Potassium tert-butoxide (molecular weight 112) (solution consisting of 12% by mass of active ingredient and 88% by mass of THF) (reagent)
- b'2 Aluminum secondary butoxide (molecular weight 246) (Organix AL-3001 manufactured by Matsumoto Fine Chemical Co., Ltd.)
- b'3 Epoxy adduct-type latent curing agent obtained using an imidazole compound (Ajinomoto Fine-Techno Co., Ltd. Amicure PN-23)
- b'4 Potassium acetate (molecular weight 98) (reagent)
- the epoxy resin composition obtained above was evaluated for low temperature curability, reaction start temperature (° C.), storage elastic modulus maintenance rate (%), and tan ⁇ peak value according to the following method.
- the test methods of the tests (1) to (4) used in the examples and comparative examples in Table 1 are as follows. The results are shown in Table 1. In addition, "-" in the table means not evaluated.
- reaction start temperature was measured using differential scanning calorimetry (DSC), and the results are shown in Table 1.
- DSC110 manufactured by Seiko Instruments Inc. was used for the DSC measurement, and the temperature was raised from 30 to 200 ° C. at a heating rate of 10 ° C./min under a nitrogen atmosphere.
- the reaction start temperature was defined as the temperature at the intersection of the baseline of the graph of the DSC measurement result and the tangent at the inflection of the peak. Further, "-" in the table means unevaluated, and Comparative Examples 1, 2, 4, and 5 are unevaluated.
- the reaction starting temperature is preferably 75 to 160 ° C., more preferably 75 to 160 ° C., using differential scanning calorimetry (DSC) from the viewpoint that it can be applied to applications requiring low temperature curability.
- the temperature is 80 to 140 ° C, particularly preferably 85 to 120 ° C.
- Storage elastic modulus maintenance rate (%) (Storage modulus E'at 250 ° C / storage elastic modulus E'at 25 ° C) x 100
- "-" in the table means not evaluated.
- the storage elastic modulus maintenance rate is preferably 5 to 99%, more preferably 7 to 95%, and particularly preferably 10 to 80% from the viewpoint of less deterioration of characteristics due to heating. be.
- the tan ⁇ peak value is preferably 0.19 or less, more preferably 0.18 or less, and particularly preferably 0.14 or less, from the viewpoint that the characteristic deterioration due to heating is small.
- Comparative Examples 1 and 2 in Table 1 are compositions using the b'1 component or the b'2 component instead of the component (B) of the present invention, but the result was that the low temperature curability was inferior. ..
- Comparative Example 3 is a composition using the b'3 component instead of the component (B) of the present invention, but the storage elastic modulus retention rate is due to the tan ⁇ peak value of 0.20. Was an inferior result.
- Comparative Example 5 was a composition in which the a'1 component was used instead of the component (A) of the present invention, but the result was that the low temperature curability was inferior.
- Example 1 The epoxy resin composition of Example 1 was placed in a metal container (diameter 5 cm) and placed in a hot air drying oven set at 70 ° C. for 60 minutes to volatilize the THF in the epoxy resin composition. Then, the epoxy resin composition is applied to a test piece made of SPCC-SD having a width of 25 mm, a length of 100 mm, and a thickness of 1 mm. Then, another SPCC-SD test piece was attached and fixed with a clip so that the overlapping surface was 25 mm ⁇ 10 mm. Then, it was cured in a hot air drying oven set at 120 ° C. for 120 minutes to obtain a test piece.
- the shear adhesion strength (unit: MPa) was measured at 25 ° C. with a universal tensile tester (tensile speed 10 mm / min.) According to JIS K6850: 1999. The result of Example 1 was 6.9 MPa.
- the tensile shear adhesive strength is preferably 4 MPa or more, more preferably 5 MPa or more.
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Abstract
L'objectif de la présente invention est de fournir une composition de résine époxyde qui a une aptitude au durcissement à basse température (75-160 °C), et à partir de laquelle un produit durci qui peut supprimer la détérioration des caractéristiques due au chauffage peut être obtenu. Une composition de résine époxyde selon la présente invention comprend : en tant que composant (A), une résine époxyde ayant au moins deux groupes glycidyle fonctionnels dans une molécule ; et en tant que composant (B), un initiateur de polymérisation ayant un groupe butoxy et un métal alcalin dans une molécule.
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JP2000053760A (ja) * | 1998-08-10 | 2000-02-22 | Toagosei Co Ltd | オキセタニル基を有する高分子量重合体の製造方法 |
WO2012070387A1 (fr) * | 2010-11-25 | 2012-05-31 | 旭化成イーマテリアルズ株式会社 | Résine époxy et composition de résine |
JP2014034680A (ja) * | 2012-08-10 | 2014-02-24 | Asahi Kasei E-Materials Corp | エポキシ樹脂組成物、硬化物及び電子部材 |
JP2019151682A (ja) * | 2018-02-28 | 2019-09-12 | 株式会社Adeka | アニオン重合開始剤及び該アニオン重合開始剤を含有する重合性組成物 |
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JP2000053760A (ja) * | 1998-08-10 | 2000-02-22 | Toagosei Co Ltd | オキセタニル基を有する高分子量重合体の製造方法 |
WO2012070387A1 (fr) * | 2010-11-25 | 2012-05-31 | 旭化成イーマテリアルズ株式会社 | Résine époxy et composition de résine |
JP2014034680A (ja) * | 2012-08-10 | 2014-02-24 | Asahi Kasei E-Materials Corp | エポキシ樹脂組成物、硬化物及び電子部材 |
JP2019151682A (ja) * | 2018-02-28 | 2019-09-12 | 株式会社Adeka | アニオン重合開始剤及び該アニオン重合開始剤を含有する重合性組成物 |
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