WO2022210190A1 - Amine derivative - Google Patents
Amine derivative Download PDFInfo
- Publication number
- WO2022210190A1 WO2022210190A1 PCT/JP2022/013647 JP2022013647W WO2022210190A1 WO 2022210190 A1 WO2022210190 A1 WO 2022210190A1 JP 2022013647 W JP2022013647 W JP 2022013647W WO 2022210190 A1 WO2022210190 A1 WO 2022210190A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- manufactured
- resin composition
- mercaptomethylthio
- amine derivative
- epoxy
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 32
- 238000002844 melting Methods 0.000 claims abstract description 35
- 230000008018 melting Effects 0.000 claims abstract description 35
- 125000005543 phthalimide group Chemical group 0.000 claims abstract description 11
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 9
- 239000003822 epoxy resin Substances 0.000 claims description 57
- 229920000647 polyepoxide Polymers 0.000 claims description 57
- 239000011342 resin composition Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 40
- 238000010438 heat treatment Methods 0.000 claims description 21
- 230000004927 fusion Effects 0.000 claims description 13
- 230000000977 initiatory effect Effects 0.000 claims description 12
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 239000003566 sealing material Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000001723 curing Methods 0.000 description 55
- 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 31
- 238000003756 stirring Methods 0.000 description 27
- -1 maleimide compounds Chemical class 0.000 description 23
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- 239000013500 performance material Substances 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000000945 filler Substances 0.000 description 15
- 239000006087 Silane Coupling Agent Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 229920006310 Asahi-Kasei Polymers 0.000 description 10
- 229920004482 WACKER® Polymers 0.000 description 10
- 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
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000004570 mortar (masonry) Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- DUILGEYLVHGSEE-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1CO1 DUILGEYLVHGSEE-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- DNVXWIINBUTFEP-UHFFFAOYSA-N 2-[(2-phenylphenoxy)methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1=CC=CC=C1 DNVXWIINBUTFEP-UHFFFAOYSA-N 0.000 description 3
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 3
- 102100027123 55 kDa erythrocyte membrane protein Human genes 0.000 description 3
- 101001057956 Homo sapiens 55 kDa erythrocyte membrane protein Proteins 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- RHTXCFRIEYHAHM-UHFFFAOYSA-N 1-(2-methylimidazol-1-yl)-3-phenoxypropan-2-ol Chemical compound CC1=NC=CN1CC(O)COC1=CC=CC=C1 RHTXCFRIEYHAHM-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 2
- BVRXXBNZYYMNMI-UHFFFAOYSA-N 2-(2-imidazol-1-ylethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCN1C=CN=C1 BVRXXBNZYYMNMI-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- YJKVPVDNBHRYDZ-UHFFFAOYSA-N 2-[2-(2-methylimidazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound CC1=NC=CN1CCN1C(=O)C2=CC=CC=C2C1=O YJKVPVDNBHRYDZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 241000233805 Phoenix Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical class C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- LPVHVQFTYXQKAP-YFKPBYRVSA-N (4r)-3-formyl-2,2-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC1(C)SC[C@@H](C(O)=O)N1C=O LPVHVQFTYXQKAP-YFKPBYRVSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- XVNGTGZGWDPIRR-UHFFFAOYSA-N 1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCS XVNGTGZGWDPIRR-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 description 1
- 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
- KOTWFRRMBONCPA-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O.O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O KOTWFRRMBONCPA-UHFFFAOYSA-N 0.000 description 1
- UFFVWIGGYXLXPC-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1N1C(=O)C=CC1=O UFFVWIGGYXLXPC-UHFFFAOYSA-N 0.000 description 1
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- JPPLPDOXWBVPCW-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC JPPLPDOXWBVPCW-UHFFFAOYSA-N 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IJJNTMLAAKKCML-UHFFFAOYSA-N tribenzyl borate Chemical compound C=1C=CC=CC=1COB(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 IJJNTMLAAKKCML-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 description 1
- HWJYGSDXNANCJM-UHFFFAOYSA-N tridodecyl borate Chemical compound CCCCCCCCCCCCOB(OCCCCCCCCCCCC)OCCCCCCCCCCCC HWJYGSDXNANCJM-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- WZGVRXXJKGXOBR-UHFFFAOYSA-N trihexadecyl borate Chemical compound CCCCCCCCCCCCCCCCOB(OCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCC WZGVRXXJKGXOBR-UHFFFAOYSA-N 0.000 description 1
- KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- GZKLCETYSGSMRA-UHFFFAOYSA-N trioctadecyl borate Chemical compound CCCCCCCCCCCCCCCCCCOB(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC GZKLCETYSGSMRA-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- DLVYHYUFIXLWKV-UHFFFAOYSA-N tris(2-ethylhexyl) borate Chemical compound CCCCC(CC)COB(OCC(CC)CCCC)OCC(CC)CCCC DLVYHYUFIXLWKV-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
- FYAMVEZOQXNCIE-UHFFFAOYSA-N tris(3-methylphenyl) borate Chemical compound CC1=CC=CC(OB(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 FYAMVEZOQXNCIE-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Definitions
- the present invention relates to amine derivatives.
- a one-component adhesive contains a main agent and a curing catalyst, or a main agent, a curing agent, and a curing catalyst. Cure catalysts are believed to have the greatest impact on the pot life and cure conditions of adhesives.
- An object of the present invention is to provide a novel amine derivative.
- the value of (melting start temperature at a heating rate of 50 ° C./min)/(melting start temperature at a heating rate of 10 ° C./min) is 1.00. It is an amine derivative having a phthalimide skeleton having a ratio of 1.10 or less.
- the value of (the melting initiation temperature at a heating rate of 50° C./min)/(the melting initiation temperature at a heating rate of 10° C./min) may be 1.00 or more and 1.01 or less.
- the absolute value of (maximum heat flow [mW / mg]) / (heat of fusion [J / g]) is 0.01 or more and 0.10 It may be below.
- the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) may be 0.023 or more and 0.045 or less.
- Another embodiment of the present invention is a curing catalyst for an epoxy resin containing any of the above amine derivatives, a resin composition containing the curing catalyst, a sealing material or adhesive containing the resin composition, or It is a cured product of the resin composition.
- a further embodiment of the present invention is any of the above methods for producing an amine derivative, comprising the step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
- the amine derivative is an epoxyamine adduct.
- Amine derivatives that exhibit such skeletons and properties are useful as curing catalysts for thermosetting resins such as epoxy resins and compounds with polymerizable double bond groups (for example, (meth)acrylic compounds and maleimide compounds).
- thermosetting resins such as epoxy resins and compounds with polymerizable double bond groups
- (meth)acrylic compounds and maleimide compounds for example, (meth)acrylic compounds and maleimide compounds.
- the curing catalyst and resin composition using the amine derivative according to the present invention are described below.
- acryl and methacryl are collectively referred to as (meth)acryl.
- the amine derivative according to one embodiment of the present invention has a long pot life and sufficient curing when used as a curing catalyst for an epoxy resin or a compound having a polymerizable double bond group ((meth)acrylic compound or maleimide compound). show gender.
- the melting point of this amine derivative can be determined by the following procedure using, for example, a differential scanning calorimeter (DSC 204 F1 Phoenix (registered trademark)) (manufactured by NETZSCH).
- DSC 204 F1 Phoenix (registered trademark) manufactured by NETZSCH.
- NETZSCH differential scanning calorimeter
- 5 mg of each resin composition is weighed into an aluminum pan, sealed with an aluminum lid, and then a hole is made in the center of the lid with a needle to prepare a measurement sample.
- the heat flow mW/mg
- the temperature at which the peak top is obtained on the graph is calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 8.0.2), and that temperature is taken as the melting point.
- the heat flow at the melting point (that is, the maximum heat flow) and the area of the peak at the melting point (that is, the heat of fusion) are analyzed by the analysis software of the device. Then the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) can be calculated. Next, the heat flow (mW/mg) was measured in the range of 25 to 250° C. under the conditions of a heating rate of 10° C./min and a heating rate of 50° C./min, and the melting initiation temperature (° C.) under each condition was determined. Analyzed, the temperature increase rate dependence can be calculated as (melting start temperature at a temperature increase rate of 50° C./min)/(melting start temperature at a temperature increase rate of 10° C./min).
- the temperature increase rate dependence of this amine derivative is the temperature increase rate dependence when the heat flow (mW/mg) is measured at a temperature increase rate of 10 ° C./min and 50 ° C./min.
- the melting start temperature at 10° C./min)/(melting start temperature at a heating rate of 10° C./min) is preferably 1.00 or more and 1.10 or less, and is 1.00 or more and 1.08 or less. is more preferably 1.00 or more and 1.05 or less, even more preferably 1.00 or more and 1.02 or less, and even more preferably 1.00 or more and 1.01 or less.
- the absolute value of the maximum heat flow/heat of fusion is preferably 0.007 or more, and preferably 0.01 or more. is more preferably 0.023 or more, preferably 0.1 or less, more preferably 0.07 or less, and even more preferably 0.045 or less.
- the term "curing catalyst” means a catalyst having a function of promoting the initiation and/or progress of polymerization when the main agent is self-polymerized or when the main agent and the curing agent are polymerized. do.
- the curing catalyst may be incorporated only at the terminal of the polymer.
- R 1 is a group selected from hydrogen, phenyl and C1-C17, preferably C1-C11 alkyl
- R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl
- R4 is a group selected from hydrogen, OH and OAc (Ac: abbreviation for acetyl group)
- n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, More preferably, it is 3 or less.
- the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
- the synthesis method includes a step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
- this curing catalyst has a phthalimide skeleton and satisfies the above specific parameters, the curing catalyst is less likely to dissolve in the resin in an unintended temperature range in the resin composition, resulting in a longer pot life and heat curing. It is useful as a curing catalyst for hardening resins.
- the curing catalyst disclosed herein may contain one or more compounds having the structural formula (I). It may also contain one or more curing catalysts other than the compound having structural formula (I).
- the resin is not particularly limited, but a thermosetting resin is preferred. Specifically, epoxy resins and compounds having a polymerizable double bond group (for example, (meth)acrylic compounds and maleimide compounds) can be exemplified.
- Epoxy resin The epoxy resin is not particularly limited, and may be a monofunctional epoxy resin or a multifunctional epoxy resin.
- a monofunctional epoxy resin is an epoxy resin having one epoxy group, and has been conventionally used as a reactive diluent to adjust the viscosity of an epoxy resin composition.
- Monofunctional epoxy resins are roughly classified into aliphatic monofunctional epoxy resins and aromatic monofunctional epoxy resins. From the viewpoint of volatility, the monofunctional epoxy resin preferably has an epoxy equivalent of 180 to 400 g/eq.
- aromatic monofunctional epoxy resins include phenyl glycidyl ether, cresyl glycidyl ether, p-s-butylphenyl glycidyl ether, styrene oxide, p-tert-butylphenyl glycidyl ether, o-phenylphenol glycidyl ether, m- Examples include, but are not limited to, phenylphenol glycidyl ether, p-phenylphenol glycidyl ether, N-glycidyl phthalimide, and the like.
- p-tert-butylphenyl glycidyl ether and phenyl glycidyl ether are preferred, and p-tert-butylphenyl glycidyl ether is particularly preferred.
- aliphatic monofunctional epoxy resins include n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, ⁇ -pinene oxide, allyl glycidyl ether, 1-vinyl-3,4-epoxycyclohexane, 1,2-epoxy-4 -(2-methyloxiranyl)-1-methylcyclohexane, 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, neodecanoic acid glycidyl ester, etc. can be, but are not limited to:
- a polyfunctional epoxy resin is an epoxy resin having two or more epoxy groups. Accordingly, the resin composition of the present disclosure may include difunctional epoxy resins, trifunctional epoxy resins, tetrafunctional epoxy resins, and the like. Polyfunctional epoxy resins are roughly classified into aliphatic polyfunctional epoxy resins and aromatic polyfunctional epoxy resins.
- aliphatic polyfunctional epoxy resins examples include (poly)ethylene glycol diglycidyl ether, (poly)propylene glycol diglycidyl ether, butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether.
- diepoxy resins such as ether, trimethylolpropane diglycidyl ether, polytetramethylene ether glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, cyclohexane type diglycidyl ether, dicyclopentadiene type diglycidyl ether; Triepoxy resins such as methylolpropane triglycidyl ether, glycerin triglycidyl ether; vinyl (3,4-cyclohexene) dioxide, 2-(3,4-epoxycyclohexyl)-5,1-spiro-(3,4-epoxy Cycloaliphatic epoxy resins such as cyclohexyl)-m-dioxane; glycidylamine type epoxy resins such as tetraglycidylbis(aminomethyl)cyclohexane; h
- cyclohexane-type diglycidyl ether means that two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having one cyclohexane ring as a base structure.
- a compound having a structure is meant.
- dicyclopentadiene-type diglycidyl ether refers to a compound having a structure in which two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having a dicyclopentadiene skeleton as a base structure. means.
- cyclohexane-type diglycidyl ether cyclohexanedimethanol diglycidyl ether is particularly preferred.
- Aromatic polyfunctional epoxy resins are polyfunctional epoxy resins having a structure containing aromatic rings such as benzene rings. Many conventional epoxy resins, such as bisphenol A type epoxy resin, are of this type. Examples of aromatic polyfunctional epoxy resins include bisphenol A type epoxy resins; branched polyfunctional bisphenol A type epoxy resins such as p-glycidyloxyphenyldimethyltrisbisphenol A diglycidyl ether; bisphenol F type epoxy resins; type epoxy resin; bisphenol S type epoxy resin; novolac type epoxy resin; tetrabromobisphenol A type epoxy resin; fluorene type epoxy resin; biphenyl aralkyl epoxy resin; ,3′,5,5′-tetramethyl-4,4′-diglycidyloxybiphenyl; diglycidylaniline, diglycidyltoluidine, triglycidyl-p-aminophenol, tetraglycidyl-m- glycidylamine-type epoxy resins
- aromatic polyfunctional epoxy resins bisphenol F-type epoxy resins, bisphenol A-type epoxy resins and glycidylamine-type epoxy resins are preferable, and among them, those having an epoxy equivalent of 90 to 200 g/eq are preferable.
- the polymer compound having a polymerizable double bond group is not particularly limited.
- compounds having an alkyl group include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, normal butyl acrylate, normal Butyl methacrylate, normal hexyl acrylate, normal hexyl methacrylate, normal heptyl acrylate, normal heptyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, normal lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, etc.; compounds having cyclohexyl acrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobornyl methacryl
- trimethylolpropane triacrylate pentaerythritol triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.
- Multifunctional (meth)acrylates of polyol derivatives such as; Pentaerythritol triarylate, pentaerythritol tetraarylate, trimethylolpropane triarylate and other polyfunctional arylates; Aronix M-7100, Aronix M-8030, Aronix M-8060 polyester (meth)acrylates such as Toagosei Co., Ltd.; Co., Ltd.), Aronix M-305, Aronix M-309, Aronix M-310, M-315, M-320, Aronix M-350, Aronix M-360, Aronix M-370, Aronix M-400, Aronix M-402, Aronix M-408, Aronix M-450, (all manufactured by Toagosei Co., Ltd.), Neomer TA-401, TA-505, EA-301, DA-600 (both Sanyo Chemical Industries Co., Ltd.) ), NK Ester A-TMPT, NK Ester
- compounds having a maleimide group include N,N'-(4,4'-diphenylmethane)bismaleimide, bisphenol A diphenyletherbismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'- Diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6'-bismaleimido-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl) ) methane, m-phenylenebismaleimide (N,N′-1,3-phenylenebismaleimide), 1,6-bismaleimidohexane, 1,2-bismaleimidoethane (N,N′-ethylenedimaleimide), N,N'-(1,2-phenylene)bismaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyl
- dimer acid-modified bismaleimide It is also possible to use dimer acid-modified bismaleimide.
- dimer acid-modified bismaleimides include liquid bismaleimides BMI-689, BMI-1500 and BMI-1700, and solid bismaleimides BMI-3000 (all manufactured by Designer Molecules).
- the resin compositions disclosed herein may contain one or more curing agents.
- Curing agents that may be contained in the resin composition of the present disclosure are not particularly limited, but include, for example, nitrogen-containing compounds such as amines and their derivatives; , oxygen-containing compounds such as phenol-terminated epoxy resins; sulfur-containing compounds such as thiol compounds.
- Nitrogen-containing compounds such as amines and derivatives thereof are not particularly limited, but aliphatic polyamines such as triethylenetetramine, tetraethylenepentamine, m-xylenediamine, trimethylhexamethylenediamine, and 2-methylpentamethylenediamine, isophorone diamine.
- Epomic Q-640 Epomic Q-643 (Mitsui Chemicals, trade name), DETDA80 (Lonza, trade name), Thothamine HM-205 (Nippon Steel & Sumikin Chemical Co., Ltd., trade name), etc. is mentioned.
- the acid anhydride-based curing agent is not particularly limited, but for example, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, methylhimic acid anhydride, alkenyl-substituted Succinic anhydride, glutaric anhydride and the like can be mentioned.
- Phenolic curing agents refer to monomers, oligomers, and polymers generally having phenolic hydroxyl groups, such as phenol novolac resins and their alkylated or allylated products, cresol novolak resins, phenol aralkyl (including phenylene and biphenylene skeleton) resins, and naphthol aralkyls. Resins, triphenol methane resins, dicyclopentadiene type phenol resins, and the like. Among them, allylphenol novolac resin is preferable.
- Thiol compounds include hydrolyzable polyfunctional thiol compounds and non-hydrolyzable polyfunctional thiol compounds.
- hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanate Nurate (manufactured by SC Organic Chemical Co., Ltd.: TEMPIC), pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: PEMP), tetraethylene glycol bis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.) : EGMP-4), dipentaerythritol hexakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: DPMP), pentaerythritol tetrakis (3-mercaptobutyrate) (manu
- non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluril (trade name: TS-G, manufactured by Shikoku Kasei Co., Ltd.), (1,3, 4,6-tetrakis(3-mercaptopropyl)glycoluril (trade name: C3 TS-G, manufactured by Shikoku Kasei Co., Ltd.), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4 ,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercapto Propyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-dimethylglycoluril,
- non-hydrolyzable polyfunctional thiol compound it is also possible to use a trifunctional or higher polythiol compound having two or more sulfide bonds in the molecule.
- thiol compounds include 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercapto propylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,7- dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, tetrakis(mercaptomethylthiomethyl) Methane
- the ratio of the curing catalyst in the resin composition is not particularly limited, it is preferably 0.01 to 50 wt%, more preferably 0.01 to 30 wt%, relative to the thermosetting resin in the resin composition. More preferably, it is 0.01 to 20 wt%.
- the pot life is defined as the time until the thickening ratio of the resin composition doubles from the initial value, and the pot life in the epoxy-thiol curing system is preferably 8 hours or longer, more preferably 12 hours or longer. , more preferably 24 hours or longer. Also in other curing systems, a longer pot life is preferable from the viewpoint of stability.
- the curable composition of the present disclosure may optionally contain, for example, the following in addition to the main agent, curing catalyst, and curing agent.
- Stabilizer A stabilizer can be added to the resin composition of the present disclosure in order to improve its storage stability and prolong its pot life.
- Various known stabilizers can be used as stabilizers for one-component adhesives based on epoxy resins. preferable.
- liquid borate compounds examples include 2,2′-oxybis(5,5′-dimethyl-1,3,2-oxaborinane), trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, tri - n-butylborate, tripentylborate, triallylborate, trihexylborate, tricyclohexylborate, trioctylborate, trinonylborate, tridecylborate, tridodecylborate, trihexadecylborate, trioctadecylborate, tris(2 -ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentoxatetradecyl)(1,4,7-trioxaundecyl) Borane, tribenzylborate, triphenylborate,
- aluminum chelate for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used.
- organic acid for example, barbituric acid can be used.
- filler A filler can be added to the resin composition of the present disclosure.
- fillers include silica fillers, glass fillers, alumina fillers, titanium oxide fillers, boron nitride fillers, aluminum nitride fillers, talc fillers, calcium carbonate fillers, resin fillers (e.g., polytetrafluoroethylene (PTFE) fillers, silicone rubber fillers, etc.), conductive fillers such as silver, copper and nickel.
- the shape is not particularly limited, and may be hollow, spherical, or amorphous.
- the filler may be surface-treated.
- Coupling agent A coupling agent can be added to the resin composition of the present disclosure.
- the coupling agent is preferably a silane coupling agent, and various silane coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto can be used. These silane coupling agents may be used alone or in combination of two or more.
- Silane coupling agents include, for example, vinyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-1003, Momentive Performance Materials Japan Co., Ltd.; A -171, Dow Corning Toray Co., Ltd.; Z-6300, Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL XL10, Himi Shoji Co., Ltd.; KBE-1003, Momentive Performance Materials Japan; A-151, Dow Corning Toray; Z-6519, Asahi Kasei Wacker Silicone; GENIOSIL GF56, Himi Shoji; Sila Ace S220, etc.
- vinyltriacetoxysilane commercially available from Asahi Kasei Wacker Silicone; GENIOSIL GF62
- vinyltris(2-methoxyethoxy)silane commercially available from Momentive Performance Materials Japan
- A-172 vinylmethyldimethoxysilane
- commercially available products include Momentive Performance Materials Japan; A-2171, Asahi Kasei Wacker Silicone; GENIOSIL XL12, etc.
- octenyltri Methoxysilane commercially available from Shin-Etsu Chemical Co., Ltd.; includes KBM-1083
- allyltrimethoxysilane commercially available from Dow Corning Toray; includes Z-6825
- p-styryltrimethoxysilane Commercially available products include KBM-1403 manufactured by Shin-Etsu Chemical Co., Ltd.).
- silane coupling agents having an acrylic group include 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-5103, etc.), and the like.
- silane coupling agents having a methacryl group include 3-methacryloxypropylmethyldimethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-502, Toray Dow Corning Co., Ltd.; Z-6033, etc.).
- 3-methacryloxypropyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-503, Momentive Performance Materials Japan Co., Ltd.; A-174, Dow Corning Toray Co., Ltd.; Z-6030 , Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF31, Himi Shoji Co., Ltd.; Sila Ace S710, etc.), 3-methacryloxypropylmethyldiethoxysilane (commercially available products include Shin-Etsu Chemical Co., Ltd.; KBE-502.
- N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-602; Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-95, Himi Shoji Co.; Sila Ace S310, etc.
- N-2-(aminoethyl)-3-aminopropyltrimethoxysilane commercially available from Shin-Etsu Chemical KBM-603, Momentive Performance Materials Japan; A-1120, Momentive Performance Materials Japan; A-1122, Dow Corning Toray; Z-6020, Dow Toray Z-6094 manufactured by Corning Corporation; Z-6094 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-91 manufactured by Himi Shoji Co.; KBM-903, manufactured by Momentive Performance Materials Japan; A-1110, manufactured by Dow Corning Toray Co.,
- the resin composition of the present disclosure may contain other additives such as carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, digestive agents, etc., within a range that does not impair the object of the present invention.
- Foaming agents, thixotropic agents, viscosity modifiers, flame retardants, coloring agents, solvents and the like can be added.
- the type and amount of each additive are as per conventional methods.
- the resin composition disclosed herein can be used, for example, as sealing materials and fillers for electronic components, dam materials, conductive or insulating adhesives, die attach materials, films, coating agents, shielding materials, and the like. can. In addition, it can be used for paints, composite materials such as pipe materials and tank materials, floor materials, civil engineering and construction materials such as membranes, adhesives, and the like, but the usage is not limited to these.
- Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 100 g, 0.363 mmol) was gradually added to the resulting solution over about 10 minutes. After dissolving everything, the mixture was heated to 70° C. and stirred at the same temperature for 6 hours. After cooling to room temperature, water (about 200 mL) was added and stirred to precipitate crystals. The resulting solid was suction filtered, washed twice with water and twice with IPA, and then dried to obtain compound 1 (85.7 g) (61% recovery).
- the measured physical properties of the product are as follows.
- 2-Methyl-1H-imidazole (manufactured by Shikoku Kasei Co., Ltd., 21.8 g, 266 mmol) was dissolved in a mixed solvent of toluene (78.7 mL) and methanol (17.7 mL), heated to 80° C., and Denacol EX was prepared.
- a toluene (38.1 mL) solution of -141 (manufactured by Nagase ChemteX Corporation, 22.0 g, 147 mmol) was added dropwise over 1 hour, followed by stirring at the same temperature for 1 hour.
- 2-methyl-1-H-imidazole (manufactured by Shikoku Kasei Co., Ltd., 150 g, 1.83 mol) was dissolved in a mixed solvent of toluene (443 mL) and methanol (121 mL) at room temperature. and heated to reflux with stirring.
- 2- ⁇ [([1,1′-biphenyl]-2-yl)oxy]methyl ⁇ oxirane (manufactured by Sanko Co., Ltd., 210 g, 0.913 mol, epoxy equivalent 230 g/eq) was added to toluene at room temperature. (363 mL) was added dropwise at a rate of 3.75 mL/min.
- the temperature corresponding to the melting point and at which a peak is obtained on the graph was calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 8.0.2). Compounds 1-6 and 8 gave clear peaks, but Compound 7 did not give a clear peak.
- the heat flow at the melting point i.e., maximum heat flow
- the area of the peak i.e., heat of fusion
- the heat flow (mW/mg) was measured under the conditions of a heating rate of 10°C/min and a heating rate of 50°C/min, and the melting initiation temperature (°C) under each condition was analyzed. Then, as the temperature increase rate dependence, (melting start temperature at a temperature increase rate of 50° C./min)/(melting start temperature at a temperature increase rate of 10° C./min) was calculated.
- the melting initiation temperature is the temperature at the intersection of the tangent line with the maximum gradient among the tangent lines of the melting peak curve and the DSC baseline on the lower temperature side than the melting point.
- Table 1 shows the evaluation results of the compound (curing catalyst).
- Epoxy-thiol curing system Compounds 1 to 4, 6, 7, and 8 as curing catalysts were put into EXA835LV (manufactured by DIC), which is an epoxy resin, and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. Then, EXA835LV or a mixture of EXA835LV and CDMDG (manufactured by Showa Denko KK) was added and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device.
- EXA835LV manufactured by DIC
- CDMDG manufactured by Showa Denko KK
- PEMP manufactured by SC Organic Chemical Co., Ltd.
- SC Organic Chemical Co., Ltd. which is a thiol resin
- stirring and defoaming were performed under vacuum to obtain a resin composition.
- Epoxy-thiol curing system Compound 1 as a curing catalyst was added to a mixture obtained by dispersing EXA835LV and TS720 (manufactured by Cabot Specialty Chemicals) using a three-roll mill and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus. C3TSG (manufactured by Shikoku Kasei Kogyo Co., Ltd.), which is a thiol resin, was added thereto and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
- EXA835LV and TS720 manufactured by Cabot Specialty Chemicals
- Epoxy homopolymerization curing system > Compounds 1, 5 and 6 as curing catalysts were put into EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus to obtain a resin composition.
- Epoxy-acid anhydride curing system Compound 1 as a curing catalyst was put into EXA835LV, which is an epoxy resin, and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus. Then, YDF8170 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) was added and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device.
- EXA835LV an epoxy resin
- Epoxy-phenol curing system > Compound 1 as a curing catalyst was added to EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. EXA835LV was put in there and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device. Furthermore, MEH8005 (manufactured by Meiwa Kasei Co., Ltd.), which is a phenolic resin, was added and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
- MEH8005 manufactured by Meiwa Kasei Co., Ltd.
- Acrylic-thiol curing system > M7100 (manufactured by Toagosei Co., Ltd.) as an acrylic resin, OMNIRAD184 (manufactured by IGM resins B.V.) as a photoradical generator, Q-1301 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a polymerization inhibitor, and a stabilizing agent.
- TS720 was dispersed with a three-roll mill as a component, and compound 1 as a curing catalyst was added to the resulting mixture and further dispersed with a three-roll mill. After PEMP was added thereto and mixed, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device to obtain a resin composition.
- the time before gelation (referred to as gel time) was measured using a gelation tester (GT-D-15A: manufactured by Eucalyptus Giken Co., Ltd.).
- a hot plate was set to 100° C., 120° C., or 150° C., and the resin composition was transferred onto the hot plate using a test rod.
- the gel time was defined as the time from touching the resin composition with a test rod until it became stringy.
- the resin composition in the example gelled within 10 minutes and had sufficient reactivity and curability.
- the curing catalyst of the present disclosure can be used not only in epoxy-thiol curing systems, but also in epoxy homopolymerization systems, epoxy-acid anhydride systems, epoxy-phenol systems, and acrylate-thiol systems. is.
- the curing catalyst of the present disclosure has a phthalimide skeleton, so it has high crystallinity and a higher melting point than conventional adducts obtained by adding an epoxy resin and an imidazole derivative. , a resin composition which is stable, hardly causes the curing catalyst to dissolve in the resin at an unintended temperature, and has a long pot life can be obtained.
- the present invention has made it possible to provide novel amine derivatives.
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Abstract
The purpose of the present invention is to provide a novel amine derivative. The present invention provides an amine derivative having a phthalimide backbone, wherein according to differential scanning calorimetry (DSC), the value of (melting start temperature at a temperature increase speed of 50°C/min)/(melting start temperature at a temperature increase speed of 10°C/min) is 1.00 to 1.10.
Description
本発明は、アミン誘導体に関する。
The present invention relates to amine derivatives.
一液性の接着剤には主剤と硬化触媒、または主剤と硬化剤と硬化触媒が含まれる。硬化触媒は接着剤の可使時間と硬化条件に最も影響を与えると考えられている。
A one-component adhesive contains a main agent and a curing catalyst, or a main agent, a curing agent, and a curing catalyst. Cure catalysts are believed to have the greatest impact on the pot life and cure conditions of adhesives.
現在、一液性の接着剤に用いられる硬化触媒は多種市販されているが、熱硬化性樹脂や熱可塑性樹脂にアミン等の官能基が修飾しているタイプ(特開昭59-053526号公報;特開平3-177418号公報)、アミン系硬化触媒を高分子体のシェルで覆ったシェルタイプ(特開2000-080146号公報)、エポキシ樹脂とイミダゾールをアダクトしただけのタイプ(特開昭60-004524号公報)が主流である。
At present, various types of curing catalysts used for one-component adhesives are commercially available. ; JP-A-3-177418), a shell type in which an amine-based curing catalyst is covered with a polymer shell (JP-A-2000-080146), a type in which an epoxy resin and imidazole are just adducted (JP-A-60 -004524) is the mainstream.
本発明は、新規なアミン誘導体を提供することを目的とする。
An object of the present invention is to provide a novel amine derivative.
本発明の一実施態様は、示差走査熱量測定(DSC)において、(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.10以下である、フタルイミド骨格を有するアミン誘導体である。前記(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.01以下であってもよい。昇温速度10℃/minの示差走査熱量測定(DSC)において、融解における、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が0.01以上0.10以下であってもよい。前記(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が0.023以上0.045以下であってもよい。
In one embodiment of the present invention, in differential scanning calorimetry (DSC), the value of (melting start temperature at a heating rate of 50 ° C./min)/(melting start temperature at a heating rate of 10 ° C./min) is 1.00. It is an amine derivative having a phthalimide skeleton having a ratio of 1.10 or less. The value of (the melting initiation temperature at a heating rate of 50° C./min)/(the melting initiation temperature at a heating rate of 10° C./min) may be 1.00 or more and 1.01 or less. In differential scanning calorimetry (DSC) at a heating rate of 10 ° C./min, the absolute value of (maximum heat flow [mW / mg]) / (heat of fusion [J / g]) is 0.01 or more and 0.10 It may be below. The absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) may be 0.023 or more and 0.045 or less.
本発明の他の実施態様は、上記いずれかのアミン誘導体を含有するエポキシ樹脂の硬化触媒、その硬化触媒を含有する樹脂組成物、その樹脂組成物を含有する封止材もしくは接着剤、またはその樹脂組成物の硬化物である。
本発明のさらなる実施態様は、フタルイミド骨格を有し、かつ1つのエポキシ基を有する化合物を、アミンにアダクトする工程を含む、上記いずれかのアミン誘導体の製造方法である。 Another embodiment of the present invention is a curing catalyst for an epoxy resin containing any of the above amine derivatives, a resin composition containing the curing catalyst, a sealing material or adhesive containing the resin composition, or It is a cured product of the resin composition.
A further embodiment of the present invention is any of the above methods for producing an amine derivative, comprising the step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
本発明のさらなる実施態様は、フタルイミド骨格を有し、かつ1つのエポキシ基を有する化合物を、アミンにアダクトする工程を含む、上記いずれかのアミン誘導体の製造方法である。 Another embodiment of the present invention is a curing catalyst for an epoxy resin containing any of the above amine derivatives, a resin composition containing the curing catalyst, a sealing material or adhesive containing the resin composition, or It is a cured product of the resin composition.
A further embodiment of the present invention is any of the above methods for producing an amine derivative, comprising the step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
==関連文献とのクロスリファレンス==
本出願は、2021年3月30日付で出願した日本国特許出願特願2021-058236に基づく優先権を主張するものであり、当該基礎出願を引用することにより、本明細書に含めるものとする。 == Cross-reference with related literature ==
This application claims priority based on Japanese Patent Application No. 2021-058236 filed on March 30, 2021, and is incorporated herein by reference to the basic application. .
本出願は、2021年3月30日付で出願した日本国特許出願特願2021-058236に基づく優先権を主張するものであり、当該基礎出願を引用することにより、本明細書に含めるものとする。 == Cross-reference with related literature ==
This application claims priority based on Japanese Patent Application No. 2021-058236 filed on March 30, 2021, and is incorporated herein by reference to the basic application. .
本発明の目的、特徴、利点、及びそのアイデアは、本明細書の記載により、当業者には明らかであり、本明細書の記載から、当業者であれば、容易に本発明を再現できる。以下に記載された発明の実施の形態及び具体的な実施例などは、本発明の好ましい実施態様を示すものであり、例示又は説明のために示されているのであって、本発明をそれらに限定するものではない。本明細書で開示されている本発明の意図並びに範囲内で、本明細書の記載に基づき、様々な改変並びに修飾ができることは、当業者にとって明らかである。
The purpose, features, advantages, and ideas of the present invention are clear to those skilled in the art from the description of the present specification, and those skilled in the art can easily reproduce the present invention from the description of the present specification. DETAILED DESCRIPTION OF THE INVENTION The embodiments, specific examples, and the like set forth below are indicative of preferred embodiments of the invention, and are presented by way of illustration or description, without regard to the invention. It is not limited. Based on the description herein, it will be apparent to those skilled in the art that various alterations and modifications can be made within the spirit and scope of the invention disclosed herein.
==アミン誘導体==
本明細書に開示のアミン誘導体は、フタルイミド骨格を有し、示差走査熱量測定(DSC)において、(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.10以下である。アミン誘導体は、エポキシアミンアダクトであることが好ましい。 == amine derivative ==
The amine derivative disclosed herein has a phthalimide skeleton, and in differential scanning calorimetry (DSC), (melting initiation temperature at a heating rate of 50° C./min)/(melting initiation temperature at a heating rate of 10° C./min) temperature) is 1.00 or more and 1.10 or less. Preferably, the amine derivative is an epoxyamine adduct.
本明細書に開示のアミン誘導体は、フタルイミド骨格を有し、示差走査熱量測定(DSC)において、(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.10以下である。アミン誘導体は、エポキシアミンアダクトであることが好ましい。 == amine derivative ==
The amine derivative disclosed herein has a phthalimide skeleton, and in differential scanning calorimetry (DSC), (melting initiation temperature at a heating rate of 50° C./min)/(melting initiation temperature at a heating rate of 10° C./min) temperature) is 1.00 or more and 1.10 or less. Preferably, the amine derivative is an epoxyamine adduct.
このような骨格と特性を示すアミン誘導体は、エポキシ樹脂や重合性二重結合基を有する化合物(例えば、(メタ)アクリル化合物やマレイミド化合物)などの熱硬化性樹脂の硬化触媒として有用である。以下、本発明に係るアミン誘導体を使用した硬化触媒および樹脂組成物などについて説明する。なお、本明細書では、アクリルとメタクリルを総称して、(メタ)アクリルと記載するものとする。
Amine derivatives that exhibit such skeletons and properties are useful as curing catalysts for thermosetting resins such as epoxy resins and compounds with polymerizable double bond groups (for example, (meth)acrylic compounds and maleimide compounds). The curing catalyst and resin composition using the amine derivative according to the present invention are described below. In this specification, acryl and methacryl are collectively referred to as (meth)acryl.
==アミン誘導体の特徴==
本発明の一実施形態に係るアミン誘導体は、エポキシ樹脂や重合性二重結合基を有する化合物((メタ)アクリル化合物やマレイミド化合物)に対する硬化触媒として用いたときのポットライフが長く、十分な硬化性を示す。 == Characteristics of amine derivatives ==
The amine derivative according to one embodiment of the present invention has a long pot life and sufficient curing when used as a curing catalyst for an epoxy resin or a compound having a polymerizable double bond group ((meth)acrylic compound or maleimide compound). show gender.
本発明の一実施形態に係るアミン誘導体は、エポキシ樹脂や重合性二重結合基を有する化合物((メタ)アクリル化合物やマレイミド化合物)に対する硬化触媒として用いたときのポットライフが長く、十分な硬化性を示す。 == Characteristics of amine derivatives ==
The amine derivative according to one embodiment of the present invention has a long pot life and sufficient curing when used as a curing catalyst for an epoxy resin or a compound having a polymerizable double bond group ((meth)acrylic compound or maleimide compound). show gender.
このアミン誘導体の融点は、例えば、示差走査熱量測定装置(DSC 204 F1 Phoenix(登録商標))(NETZSCH製)を用いて、次の手順で求めることができる。まず、アルミパンに各樹脂組成物5mgを計量し、アルミ製の蓋でシーリングした後、その蓋の中心に針で穴を開けて測定サンプルを準備する。次に、この測定サンプルを、窒素雰囲気下(100mL/分)、25℃から250℃の温度範囲、昇温速度10℃/分の条件で昇温しながら熱流(mW/mg)を測定する。グラフ上でピークトップが得られる温度を解析ソフト(NETZSCH Proteus-Thermal Analysis バージョン8.0.2)で算出し、その温度を融点とする。
The melting point of this amine derivative can be determined by the following procedure using, for example, a differential scanning calorimeter (DSC 204 F1 Phoenix (registered trademark)) (manufactured by NETZSCH). First, 5 mg of each resin composition is weighed into an aluminum pan, sealed with an aluminum lid, and then a hole is made in the center of the lid with a needle to prepare a measurement sample. Next, the heat flow (mW/mg) is measured while raising the temperature of this measurement sample under the conditions of a nitrogen atmosphere (100 mL/min), a temperature range of 25° C. to 250° C., and a heating rate of 10° C./min. The temperature at which the peak top is obtained on the graph is calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 8.0.2), and that temperature is taken as the melting point.
上述のようにして融点を算出するときに、融点における熱流(すなわち、最大熱流)と、融点におけるピークの面積(すなわち、融解熱)を装置の解析ソフトによって解析する。そして、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値を計算できる。次に、25~250℃の範囲で、昇温速度10℃/分と昇温速度50℃/分の条件で熱流(mW/mg)を測定し、各条件での融解開始温度(℃)を解析し、昇温速度依存度として、(昇温速度50℃/分の時の融解開始温度)/(昇温速度10℃/分の時の融解開始温度)を算出できる。
When calculating the melting point as described above, the heat flow at the melting point (that is, the maximum heat flow) and the area of the peak at the melting point (that is, the heat of fusion) are analyzed by the analysis software of the device. Then the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) can be calculated. Next, the heat flow (mW/mg) was measured in the range of 25 to 250° C. under the conditions of a heating rate of 10° C./min and a heating rate of 50° C./min, and the melting initiation temperature (° C.) under each condition was determined. Analyzed, the temperature increase rate dependence can be calculated as (melting start temperature at a temperature increase rate of 50° C./min)/(melting start temperature at a temperature increase rate of 10° C./min).
(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が大きくなるほど、意図しない温度域での硬化触媒の樹脂への溶解が起こりにくいため、ポットライフが長くなることが期待できる。また、昇温速度依存度が小さくなるほど、意図した温度域での硬化触媒の樹脂への溶解が瞬時に起こるため、十分なポットライフを維持したまま、十分な硬化性が期待できる。
The larger the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]), the longer the pot life because the curing catalyst is less likely to dissolve in the resin in an unintended temperature range. can be expected. In addition, as the temperature increase rate dependence decreases, the curing catalyst dissolves in the resin in the intended temperature range instantaneously, so sufficient curability can be expected while maintaining a sufficient pot life.
このアミン誘導体の昇温速度依存度は昇温速度10℃/分および50℃/分の条件で熱流(mW/mg)を測定したときの昇温速度依存度、すなわち(昇温速度50℃/分の時の融解開始温度)/(昇温速度10℃/分の時の融解開始温度)が、1.00以上1.10以下であることが好ましく、1.00以上1.08以下であることがより好ましく、1.00以上1.05以下であることがさらに好ましく、1.00以上1.02以下であることがさらに好ましく、1.00以上1.01以下であることがさらに好ましい。また、昇温速度10℃/分の条件で熱流(mW/mg)を測定したときの、最大熱流/融解熱の絶対値が0.007以上であることが好ましく、0.01以上であることがより好ましく、0.023以上であることがさらに好ましく、そして0.1以下であることが好ましく、0.07以下であることがより好ましく、0.045以下であることがさらに好ましい。
The temperature increase rate dependence of this amine derivative is the temperature increase rate dependence when the heat flow (mW/mg) is measured at a temperature increase rate of 10 ° C./min and 50 ° C./min. The melting start temperature at 10° C./min)/(melting start temperature at a heating rate of 10° C./min) is preferably 1.00 or more and 1.10 or less, and is 1.00 or more and 1.08 or less. is more preferably 1.00 or more and 1.05 or less, even more preferably 1.00 or more and 1.02 or less, and even more preferably 1.00 or more and 1.01 or less. In addition, when the heat flow (mW/mg) is measured at a heating rate of 10°C/min, the absolute value of the maximum heat flow/heat of fusion is preferably 0.007 or more, and preferably 0.01 or more. is more preferably 0.023 or more, preferably 0.1 or less, more preferably 0.07 or less, and even more preferably 0.045 or less.
==硬化触媒==
本明細書に開示のフタルイミド骨格を有するアミン誘導体を含む硬化触媒の一実施形態は、下記の構造式(I)を有する化合物を含有する硬化触媒である。なお、本明細書において、硬化触媒(curing catalyst)とは、主剤が自己重合するか、または主剤と硬化剤が重合する時に、その重合の開始及び/又は進行を促進する機能を有する触媒を意味する。なお、硬化触媒は、重合体の末端のみに取り込まれることがある。
(式中、
R1は、水素、フェニルおよびC1~C17、好ましくはC1~C11のアルキルから選択される基であり、
R2、R3、R5は、それぞれ独立して、水素およびC1~C6のアルキルから選択される基であり、
R4は、水素、OHおよびOAc(Ac:アセチル基の略号)から選択される基であり、 nとmは整数であり、その和が1以上であって、12以下、好ましくは6以下、より好ましくは3以下である。)
好ましくは、R4が水素のときnとmの和が1で、R4がOHのときnもmも1である。 == Curing catalyst ==
One embodiment of the curing catalyst comprising an amine derivative having a phthalimide skeleton disclosed herein is a curing catalyst containing a compound having the following structural formula (I). In the present specification, the term "curing catalyst" means a catalyst having a function of promoting the initiation and/or progress of polymerization when the main agent is self-polymerized or when the main agent and the curing agent are polymerized. do. In addition, the curing catalyst may be incorporated only at the terminal of the polymer.
(In the formula,
R 1 is a group selected from hydrogen, phenyl and C1-C17, preferably C1-C11 alkyl,
R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl;
R4 is a group selected from hydrogen, OH and OAc (Ac: abbreviation for acetyl group), n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, More preferably, it is 3 or less. )
Preferably, the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
本明細書に開示のフタルイミド骨格を有するアミン誘導体を含む硬化触媒の一実施形態は、下記の構造式(I)を有する化合物を含有する硬化触媒である。なお、本明細書において、硬化触媒(curing catalyst)とは、主剤が自己重合するか、または主剤と硬化剤が重合する時に、その重合の開始及び/又は進行を促進する機能を有する触媒を意味する。なお、硬化触媒は、重合体の末端のみに取り込まれることがある。
R1は、水素、フェニルおよびC1~C17、好ましくはC1~C11のアルキルから選択される基であり、
R2、R3、R5は、それぞれ独立して、水素およびC1~C6のアルキルから選択される基であり、
R4は、水素、OHおよびOAc(Ac:アセチル基の略号)から選択される基であり、 nとmは整数であり、その和が1以上であって、12以下、好ましくは6以下、より好ましくは3以下である。)
好ましくは、R4が水素のときnとmの和が1で、R4がOHのときnもmも1である。 == Curing catalyst ==
One embodiment of the curing catalyst comprising an amine derivative having a phthalimide skeleton disclosed herein is a curing catalyst containing a compound having the following structural formula (I). In the present specification, the term "curing catalyst" means a catalyst having a function of promoting the initiation and/or progress of polymerization when the main agent is self-polymerized or when the main agent and the curing agent are polymerized. do. In addition, the curing catalyst may be incorporated only at the terminal of the polymer.
R 1 is a group selected from hydrogen, phenyl and C1-C17, preferably C1-C11 alkyl,
R 2 , R 3 , R 5 are each independently a group selected from hydrogen and C1-C6 alkyl;
R4 is a group selected from hydrogen, OH and OAc (Ac: abbreviation for acetyl group), n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, More preferably, it is 3 or less. )
Preferably, the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
これらの化合物は、実施例に記載の方法および公知の方法を用いて、容易に製造可能である。化合物がエポキシアミンアダクトの場合、その合成方法は、フタルイミド骨格を有し、かつ1つのエポキシ基を有する化合物を、アミンにアダクトする工程を含む。
These compounds can be easily produced using the methods described in the Examples and known methods. When the compound is an epoxyamine adduct, the synthesis method includes a step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
この硬化触媒は、フタルイミド骨格を有することにより上記特定のパラメータを満たすため、樹脂組成物中で、意図しない温度域での硬化触媒の樹脂への溶解が起こりにくく、ポットライフが長くなり、熱硬化性樹脂の硬化触媒として有用である。
Since this curing catalyst has a phthalimide skeleton and satisfies the above specific parameters, the curing catalyst is less likely to dissolve in the resin in an unintended temperature range in the resin composition, resulting in a longer pot life and heat curing. It is useful as a curing catalyst for hardening resins.
本明細書に開示の硬化触媒は、構造式(I)を有する化合物の1種または複数種を含有してもよい。また、構造式(I)を有する化合物以外の1種または複数種の他の硬化触媒を含有してもよい。
The curing catalyst disclosed herein may contain one or more compounds having the structural formula (I). It may also contain one or more curing catalysts other than the compound having structural formula (I).
==樹脂組成物==
本明細書に開示のフタルイミド骨格を有するアミン誘導体を含む樹脂組成物の一実施形態は、構造式(I)を有する硬化触媒と、樹脂とを含有する樹脂組成物である。この樹脂組成物は、従来の硬化触媒を使用した樹脂組成物より安定であり、可使時間が長いという特徴を有する。 == resin composition ==
One embodiment of the resin composition containing the amine derivative having a phthalimide skeleton disclosed herein is a resin composition containing a curing catalyst having the structural formula (I) and a resin. This resin composition is more stable than resin compositions using conventional curing catalysts, and has a longer pot life.
本明細書に開示のフタルイミド骨格を有するアミン誘導体を含む樹脂組成物の一実施形態は、構造式(I)を有する硬化触媒と、樹脂とを含有する樹脂組成物である。この樹脂組成物は、従来の硬化触媒を使用した樹脂組成物より安定であり、可使時間が長いという特徴を有する。 == resin composition ==
One embodiment of the resin composition containing the amine derivative having a phthalimide skeleton disclosed herein is a resin composition containing a curing catalyst having the structural formula (I) and a resin. This resin composition is more stable than resin compositions using conventional curing catalysts, and has a longer pot life.
樹脂は特に限定されないが、熱硬化性樹脂が好ましい。具体的には、エポキシ樹脂や重合性二重結合基を有する化合物(例えば、(メタ)アクリル化合物やマレイミド化合物)が例示できる。
The resin is not particularly limited, but a thermosetting resin is preferred. Specifically, epoxy resins and compounds having a polymerizable double bond group (for example, (meth)acrylic compounds and maleimide compounds) can be exemplified.
(1)エポキシ樹脂
エポキシ樹脂は特に限定されず、単官能エポキシ樹脂であっても、多官能エポキシ樹脂であってもよい。
単官能エポキシ樹脂は、エポキシ基を1個有するエポキシ樹脂であり、従来から反応性希釈剤としてエポキシ樹脂組成物の粘度調整に用いられている。単官能エポキシ樹脂は、脂肪族単官能エポキシ樹脂と芳香族単官能エポキシ樹脂に大別される。揮発性の観点から、単官能エポキシ樹脂は、エポキシ当量が180~400g/eqであることが好ましい。 (1) Epoxy resin The epoxy resin is not particularly limited, and may be a monofunctional epoxy resin or a multifunctional epoxy resin.
A monofunctional epoxy resin is an epoxy resin having one epoxy group, and has been conventionally used as a reactive diluent to adjust the viscosity of an epoxy resin composition. Monofunctional epoxy resins are roughly classified into aliphatic monofunctional epoxy resins and aromatic monofunctional epoxy resins. From the viewpoint of volatility, the monofunctional epoxy resin preferably has an epoxy equivalent of 180 to 400 g/eq.
エポキシ樹脂は特に限定されず、単官能エポキシ樹脂であっても、多官能エポキシ樹脂であってもよい。
単官能エポキシ樹脂は、エポキシ基を1個有するエポキシ樹脂であり、従来から反応性希釈剤としてエポキシ樹脂組成物の粘度調整に用いられている。単官能エポキシ樹脂は、脂肪族単官能エポキシ樹脂と芳香族単官能エポキシ樹脂に大別される。揮発性の観点から、単官能エポキシ樹脂は、エポキシ当量が180~400g/eqであることが好ましい。 (1) Epoxy resin The epoxy resin is not particularly limited, and may be a monofunctional epoxy resin or a multifunctional epoxy resin.
A monofunctional epoxy resin is an epoxy resin having one epoxy group, and has been conventionally used as a reactive diluent to adjust the viscosity of an epoxy resin composition. Monofunctional epoxy resins are roughly classified into aliphatic monofunctional epoxy resins and aromatic monofunctional epoxy resins. From the viewpoint of volatility, the monofunctional epoxy resin preferably has an epoxy equivalent of 180 to 400 g/eq.
芳香族単官能エポキシ樹脂の例としては、フェニルグリシジルエーテル、クレジルグリシジルエーテル、p-s-ブチルフェニルグリシジルエーテル、スチレンオキシド、p-tert-ブチルフェニルグリシジルエーテル、o-フェニルフェノールグリシジルエーテル、m-フェニルフェノールグリシジルエーテル、p-フェニルフェノールグリシジルエーテル、N-グリシジルフタルイミド等を挙げることができるが、これらに限定されない。これらのうち、p-tert-ブチルフェニルグリシジルエーテル及びフェニルグリシジルエーテルが好ましく、p-tert-ブチルフェニルグリシジルエーテルが特に好ましい。
Examples of aromatic monofunctional epoxy resins include phenyl glycidyl ether, cresyl glycidyl ether, p-s-butylphenyl glycidyl ether, styrene oxide, p-tert-butylphenyl glycidyl ether, o-phenylphenol glycidyl ether, m- Examples include, but are not limited to, phenylphenol glycidyl ether, p-phenylphenol glycidyl ether, N-glycidyl phthalimide, and the like. Among these, p-tert-butylphenyl glycidyl ether and phenyl glycidyl ether are preferred, and p-tert-butylphenyl glycidyl ether is particularly preferred.
脂肪族単官能エポキシ樹脂の例としては、n-ブチルグリシジルエーテル、2-エチルヘキシルグリシジルエーテル、α-ピネンオキシド、アリルグリシジルエーテル、1-ビニル-3,4-エポキシシクロヘキサン、1,2-エポキシ-4-(2-メチルオキシラニル)-1-メチルシクロヘキサン、1,3-ビス(3-グリシドキシプロピル)-1,1,3,3-テトラメチルジシロキサン、ネオデカン酸グリシジルエステル等を挙げることができるが、これらに限定されない。
Examples of aliphatic monofunctional epoxy resins include n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, α-pinene oxide, allyl glycidyl ether, 1-vinyl-3,4-epoxycyclohexane, 1,2-epoxy-4 -(2-methyloxiranyl)-1-methylcyclohexane, 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, neodecanoic acid glycidyl ester, etc. can be, but are not limited to:
多官能エポキシ樹脂とは、2個以上のエポキシ基を有するエポキシ樹脂をいう。従って、本開示の樹脂組成物は、2官能エポキシ樹脂、3官能エポキシ樹脂、4官能エポキシ樹脂、などを含んでもよい。多官能エポキシ樹脂は、脂肪族多官能エポキシ樹脂と芳香族多官能エポキシ樹脂に大別される。
A polyfunctional epoxy resin is an epoxy resin having two or more epoxy groups. Accordingly, the resin composition of the present disclosure may include difunctional epoxy resins, trifunctional epoxy resins, tetrafunctional epoxy resins, and the like. Polyfunctional epoxy resins are roughly classified into aliphatic polyfunctional epoxy resins and aromatic polyfunctional epoxy resins.
脂肪族多官能エポキシ樹脂の例としては、(ポリ)エチレングリコールジグリシジルエーテル、(ポリ)プロピレングリコールジグリシジルエーテル、ブタンジオールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、1,6-ヘキサンジオールジグリシジルエーテル、トリメチロールプロパンジグリシジルエーテル、ポリテトラメチレンエーテルグリコールジグリシジルエーテル、グリセリンジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、シクロヘキサン型ジグリシジルエーテル、ジシクロペンタジエン型ジグリシジルエーテルのようなジエポキシ樹脂;トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテルのようなトリエポキシ樹脂;ビニル(3,4-シクロヘキセン)ジオキシド、2-(3,4-エポキシシクロヘキシル)-5,1-スピロ-(3,4-エポキシシクロヘキシル)-m-ジオキサンのような脂環式エポキシ樹脂;テトラグリシジルビス(アミノメチル)シクロヘキサンのようなグリシジルアミン型エポキシ樹脂;1,3-ジグリシジル-5-メチル-5-エチルヒダントインのようなヒダントイン型エポキシ樹脂;及び-1,3-ビス(3-グリシドキシプロピル)-1,1,3,3-テトラメチルジシロキサンのようなシリコーン骨格を有するエポキシ樹脂などが挙げられるが、これらに限定されない。
Examples of aliphatic polyfunctional epoxy resins include (poly)ethylene glycol diglycidyl ether, (poly)propylene glycol diglycidyl ether, butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether. diepoxy resins such as ether, trimethylolpropane diglycidyl ether, polytetramethylene ether glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, cyclohexane type diglycidyl ether, dicyclopentadiene type diglycidyl ether; Triepoxy resins such as methylolpropane triglycidyl ether, glycerin triglycidyl ether; vinyl (3,4-cyclohexene) dioxide, 2-(3,4-epoxycyclohexyl)-5,1-spiro-(3,4-epoxy Cycloaliphatic epoxy resins such as cyclohexyl)-m-dioxane; glycidylamine type epoxy resins such as tetraglycidylbis(aminomethyl)cyclohexane; hydantoins such as 1,3-diglycidyl-5-methyl-5-ethylhydantoin. type epoxy resin; and epoxy resins having a silicone skeleton such as -1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, but are limited to these not.
前記の例のうち、「シクロヘキサン型ジグリシジルエーテル」とは、2個のグリシジル基が、各々エーテル結合を介して、1個のシクロヘキサン環を母体構造として有する2価の飽和炭化水素基に結合した構造を有する化合物を意味する。「ジシクロペンタジエン型ジグリシジルエーテル」とは、2個のグリシジル基が、各々エーテル結合を介して、ジシクロペンタジエン骨格を母体構造として有する2価の飽和炭化水素基に結合した構造を有する化合物を意味する。また、シクロヘキサン型ジグリシジルエーテルとしては、シクロヘキサンジメタノールジグリシジルエーテルが特に好ましい。
Among the above examples, "cyclohexane-type diglycidyl ether" means that two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having one cyclohexane ring as a base structure. A compound having a structure is meant. The term "dicyclopentadiene-type diglycidyl ether" refers to a compound having a structure in which two glycidyl groups are each bonded via an ether bond to a divalent saturated hydrocarbon group having a dicyclopentadiene skeleton as a base structure. means. As the cyclohexane-type diglycidyl ether, cyclohexanedimethanol diglycidyl ether is particularly preferred.
芳香族多官能エポキシ樹脂は、ベンゼン環等の芳香環を含む構造を有する多官能エポキシ樹脂である。ビスフェノールA型エポキシ樹脂など、従来頻用されているエポキシ樹脂にはこの種のものが多い。芳香族多官能エポキシ樹脂の例としては、ビスフェノールA型エポキシ樹脂;p-グリシジルオキシフェニルジメチルトリスビスフェノールAジグリシジルエーテルのような分岐状多官能ビスフェノールA型エポキシ樹脂;ビスフェノールF型エポキシ樹脂;ビスフェノールE型エポキシ樹脂;ビスフェノールS型エポキシ樹脂;ノボラック型エポキシ樹脂;テトラブロモビスフェノールA型エポキシ樹脂;フルオレン型エポキシ樹脂;ビフェニルアラルキルエポキシ樹脂;1,4-フェニルジメタノールジグリシジルエーテルのようなジエポキシ樹脂;3,3',5,5'-テトラメチル-4,4'-ジグリシジルオキシビフェニルのようなビフェニル型エポキシ樹脂;ジグリシジルアニリン、ジグリシジルトルイジン、トリグリシジル-p-アミノフェノール、テトラグリシジル-m-キシリレンジアミンのようなグリシジルアミン型エポキシ樹脂;及びナフタレン環含有エポキシ樹脂などが挙げられるが、これらに限定されない。
Aromatic polyfunctional epoxy resins are polyfunctional epoxy resins having a structure containing aromatic rings such as benzene rings. Many conventional epoxy resins, such as bisphenol A type epoxy resin, are of this type. Examples of aromatic polyfunctional epoxy resins include bisphenol A type epoxy resins; branched polyfunctional bisphenol A type epoxy resins such as p-glycidyloxyphenyldimethyltrisbisphenol A diglycidyl ether; bisphenol F type epoxy resins; type epoxy resin; bisphenol S type epoxy resin; novolac type epoxy resin; tetrabromobisphenol A type epoxy resin; fluorene type epoxy resin; biphenyl aralkyl epoxy resin; ,3′,5,5′-tetramethyl-4,4′-diglycidyloxybiphenyl; diglycidylaniline, diglycidyltoluidine, triglycidyl-p-aminophenol, tetraglycidyl-m- glycidylamine-type epoxy resins such as xylylenediamine; and naphthalene ring-containing epoxy resins, but are not limited thereto.
芳香族多官能エポキシ樹脂としては、ビスフェノールF型エポキシ樹脂、ビスフェノールA型エポキシ樹脂及びグリシジルアミン型エポキシ樹脂が好ましく、中でもそのエポキシ当量が90~200g/eqであるものが好ましい。
As aromatic polyfunctional epoxy resins, bisphenol F-type epoxy resins, bisphenol A-type epoxy resins and glycidylamine-type epoxy resins are preferable, and among them, those having an epoxy equivalent of 90 to 200 g/eq are preferable.
(2)重合性二重結合基を有する化合物
重合性二重結合基を有する高分子化合物は特に限定されないが、ビニル基、特に(メタ)アクリル基やマレイミド基を、反応性二重結合基として有する高分子化合物が好ましい。 (2) Compound having a polymerizable double bond group The polymer compound having a polymerizable double bond group is not particularly limited. A polymer compound having
重合性二重結合基を有する高分子化合物は特に限定されないが、ビニル基、特に(メタ)アクリル基やマレイミド基を、反応性二重結合基として有する高分子化合物が好ましい。 (2) Compound having a polymerizable double bond group The polymer compound having a polymerizable double bond group is not particularly limited. A polymer compound having
(メタ)アクリル化合物のうち、例えば、アルキル基を持つ化合物として、メチルアクリレート、メチルメタクリレート、エチルアクリレート、エチルメタクリレート、n-プロピルアクリレート、n-プロピルメタクリレート、イソプロピルアクリレート、イソプロピルメタクリレート、ノルマルブチルアクリレート、ノルマルブチルメタクリレート、ノルマルヘキシルアクリレート、ノルマルヘキシルメタクリレート、ノルマルヘプチルアクリレート、ノルマルヘプチルメタクリレート、2-エチルヘキシルアクリレート、2-エチルヘキシルメタクリレート、ノルマルラウリルアクリレート、ラウリルメタクリレート、ステアリルアクリレート、ステアリルメタクリレート等;脂環式炭化水素基を有する化合物として、シクロヘキシルアクリレート、シクロヘキシルメタクリレート、イソボルニルアクリレート、イソボルニルメタクリレート等;芳香族基を有するビニル系単量体として、スチレン、α-メチルスチレン、α-クロロスチレン、ビニルトルエン等;水酸基を有する化合物として、2-ヒドロキシエチルアクリレート、2-ヒドロキシエチルメタクリレート、2-ヒドロキシプロピルアクリレート、2-ヒドロキシプロピルメタクリレート、3-ヒドロキシプロピルアクリレート、3-ヒドロキシプロピルメタクリレート、4-ヒドロキシブチルアクリレート、4-ヒドロキシブチルメタクリレート、ジエチレングリコールモノアクリレート、シクロヘキサンジメタノールモノアクリレート、シクロヘキサンジメタノールモノメタクリレート等;(メタ)アクリルアミド類として、アクリルアミド、N-メチロールアクリルアミド、N-メトキシメチルアクリルアミド、N-エトキシメチルアクリルアミド、N-イソブトキシメチルアクリルアミド、N-ブトキシメチルアクリルアミド、メタクリルアミド、N-メチロールメタクリルアミド、N-メトキシメチルメタクリルアミド、N-エトキシメチルメタクリルアミド、N-イソブトキシメチルメタクリルアミド、N-ブトキシメチルメタクリルアミド等が例示できる。また、ビニル基を3個以上有する化合物として、トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジトリメチロールプロパンテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート等のポリオール誘導体の多官能(メタ)アクリレート;ペンタエリスリトールトリアリレート、ペンタエリスリトールテトラアリレート、トリメチロールプロパントリアリレート等の多官能アリレート;アロニックスM-7100、アロニックスM-8030、アロニックスM-8060(いずれも東亞合成(株)製)等のポリエステル(メタ)アクリレート;EO変性多官能アクリレート、PO変性多官能アクリレート、PETIA、PETRA、TMPTA、TMPEOTA、OTA480、EBECRYL12、EBECRYL40、EBECRYL140、DPHA(いずれもダイセル・サイテック(株)製)、アロニックスM-305、アロニックスM-309、アロニックスM-310、M-315、M-320、アロニックスM-350、アロニックスM-360、アロニックスM-370、アロニックスM-400、アロニックスM-402、アロニックスM-408、アロニックスM-450、(いずれも東亞合成(株)製)、ネオマーTA-401、TA-505、EA-301、DA-600(いずれも三洋化成工業(株)製)、NKエステルA-TMPT、NKエステルAD-TMP、NKエステルA-TMPT-3EO、NKエステルA-TMPT-9EO、NKエステルA-TM-4E、NKエステルA-TM-4P、NKエステルTMPT-9EO、NKエステルA-DPH、NKエステルA-TMMT、NKエステルA-9550、NKエステルATM-35E、NKエステルTMPT(いずれも新中村化学工業(株)製)などのポリエーテル(メタ)アクリレート等が例示できる。
Among (meth)acrylic compounds, for example, compounds having an alkyl group include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, normal butyl acrylate, normal Butyl methacrylate, normal hexyl acrylate, normal hexyl methacrylate, normal heptyl acrylate, normal heptyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, normal lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, etc.; compounds having cyclohexyl acrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, etc.; vinyl monomers having an aromatic group, styrene, α-methylstyrene, α-chlorostyrene, vinyltoluene, etc.; 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxy Butyl methacrylate, diethylene glycol monoacrylate, cyclohexanedimethanol monoacrylate, cyclohexanedimethanol monomethacrylate, etc.; Examples include methylacrylamide, N-butoxymethylacrylamide, methacrylamide, N-methylolmethacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylmethacrylamide, N-isobutoxymethylmethacrylamide, and N-butoxymethylmethacrylamide. . Further, as compounds having 3 or more vinyl groups, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate. Multifunctional (meth)acrylates of polyol derivatives such as; Pentaerythritol triarylate, pentaerythritol tetraarylate, trimethylolpropane triarylate and other polyfunctional arylates; Aronix M-7100, Aronix M-8030, Aronix M-8060 polyester (meth)acrylates such as Toagosei Co., Ltd.; Co., Ltd.), Aronix M-305, Aronix M-309, Aronix M-310, M-315, M-320, Aronix M-350, Aronix M-360, Aronix M-370, Aronix M-400, Aronix M-402, Aronix M-408, Aronix M-450, (all manufactured by Toagosei Co., Ltd.), Neomer TA-401, TA-505, EA-301, DA-600 (both Sanyo Chemical Industries Co., Ltd.) ), NK Ester A-TMPT, NK Ester AD-TMP, NK Ester A-TMPT-3EO, NK Ester A-TMPT-9EO, NK Ester A-TM-4E, NK Ester A-TM-4P, NK Ester TMPT -9EO, NK Ester A-DPH, NK Ester A-TMMT, NK Ester A-9550, NK Ester ATM-35E, NK Ester TMPT (both manufactured by Shin-Nakamura Chemical Co., Ltd.) and other polyether (meth)acrylates etc. can be exemplified.
例えば、マレイミド基を持つ化合物として、N,N’-(4,4’-ジフェニルメタン)ビスマレイミド、ビスフェノール A ジフェニルエーテルビスマレイミド、3,3'-ジメチル-5,5'-ジエチル-4,4'-ジフェニルメタンビスマレイミド、4-メチル-1,3-フェニレンビスマレイミド、1,6’-ビスマレイミド-(2,2,4-トリメチル)ヘキサン、ビス-(3-エチル-5-メチル-4-マレイミドフェニル)メタン、m-フェニレンビスマレイミド(N,N’-1,3-フェニレンビスマレイミド)、1,6-ビスマレイミドヘキサン、1,2-ビスマレイミドエタン(N,N'-エチレンジマェイミド)、N,N'-(1,2-フェニレン)ビスマレイミド、N,N'-1,4-フェニレンジマレイミド、N,N'-(スルホニルジ-p-フェニレン)ジマレイミド、N,N'-[3,3'-(1,3-フェニレンジオキシ)ジフェニル]ビスマレイミド等が挙げられる。また、ダイマー酸変性ビスマレイミドを用いることも可能である。例えば、ダイマー酸変性ビスマレイミドとして、液状のビスマレイミドであるBMI-689、BMI-1500、BMI-1700、または固形のビスマレイミドであるBMI-3000(いずれもDesigner molecules社製)が挙げられる。
For example, compounds having a maleimide group include N,N'-(4,4'-diphenylmethane)bismaleimide, bisphenol A diphenyletherbismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'- Diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6'-bismaleimido-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl) ) methane, m-phenylenebismaleimide (N,N′-1,3-phenylenebismaleimide), 1,6-bismaleimidohexane, 1,2-bismaleimidoethane (N,N′-ethylenedimaleimide), N,N'-(1,2-phenylene)bismaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyldi-p-phenylene)dimaleimide, N,N'-[3 , 3′-(1,3-phenylenedioxy)diphenyl]bismaleimide and the like. It is also possible to use dimer acid-modified bismaleimide. Examples of dimer acid-modified bismaleimides include liquid bismaleimides BMI-689, BMI-1500 and BMI-1700, and solid bismaleimides BMI-3000 (all manufactured by Designer Molecules).
<硬化剤>
本明細書に開示の樹脂組成物は、1種または複数種の硬化剤を含有してもよい。
本開示の樹脂組成物が含有してもよい硬化剤は特に限定されないが、例えば、アミンとその誘導体などの窒素含有化合物;カルボン酸末端ポリエステル、酸無水物系、フェノール系、ビスフェノールA及びクレゾールノボラック、フェノール末端エポキシ樹脂などの酸素含有化合物;チオール化合物などの含硫黄化合物が挙げられる。 <Curing agent>
The resin compositions disclosed herein may contain one or more curing agents.
Curing agents that may be contained in the resin composition of the present disclosure are not particularly limited, but include, for example, nitrogen-containing compounds such as amines and their derivatives; , oxygen-containing compounds such as phenol-terminated epoxy resins; sulfur-containing compounds such as thiol compounds.
本明細書に開示の樹脂組成物は、1種または複数種の硬化剤を含有してもよい。
本開示の樹脂組成物が含有してもよい硬化剤は特に限定されないが、例えば、アミンとその誘導体などの窒素含有化合物;カルボン酸末端ポリエステル、酸無水物系、フェノール系、ビスフェノールA及びクレゾールノボラック、フェノール末端エポキシ樹脂などの酸素含有化合物;チオール化合物などの含硫黄化合物が挙げられる。 <Curing agent>
The resin compositions disclosed herein may contain one or more curing agents.
Curing agents that may be contained in the resin composition of the present disclosure are not particularly limited, but include, for example, nitrogen-containing compounds such as amines and their derivatives; , oxygen-containing compounds such as phenol-terminated epoxy resins; sulfur-containing compounds such as thiol compounds.
アミンとその誘導体などの窒素含有化合物は特に限定されないが、トリエチレンテトラアミン、テトラエチレンペンタミン、m-キシレンジアミン、トリメチルヘキサメチレンジアミン、2-メチルペンタメチレンジアミンなどの脂肪族ポリアミン、イソフォロンジアミン、1,3-ビスアミノメチルシクロヘキサン、ビス(4-アミノシクロヘキシル)メタン、ノルボルネンジアミン、1,2-ジアミノシクロヘキサンなどの脂環式ポリアミン、N-アミノエチルピペラジン、1,4-ビス(2-アミノ-2-メチルプロピル)ピペラジンなどのピペラジン型のポリアミン、ジエチルトルエンジアミン、ジメチルチオトルエンジアミン、4,4’-ジアミノ-3,3’-ジエチルジフェニルメタン、ビス(メチルチオ)トルエンジアミン、ジアミノジフェニルメタン、m-フェニレンジアミン、ジアミノジフェニルスルホン、ジエチルトルエンジアミン、トリメチレンビス(4-アミノベンゾエート)、ポリテトラメチレンオキシド-ジ-p-アミノベンゾエートなどの芳香族ポリアミン類が例示できる。市販品としては、エピキュア-W、エピキュア-Z(油化シェルエポキシ株式会社、商品名)、jERキュア(登録商標)-W、jERキュア(登録商標)-Z(三菱ケミカル株式会社、商品名)、カヤハードA-A、カヤハードA-B、カヤハードA-S(日本化薬株式会社、商品名)、トートアミンHM-205(新日鉄住金化学株式会社、商品名)、アデカハードナーEH-101(株式会社ADEKA、商品名)、エポミックQ-640、エポミックQ-643(三井化学株式会社、商品名)、DETDA80(Lonza社、商品名)、トートアミンHM-205(新日鉄住金化学株式会社、商品名)等が挙げられる。
Nitrogen-containing compounds such as amines and derivatives thereof are not particularly limited, but aliphatic polyamines such as triethylenetetramine, tetraethylenepentamine, m-xylenediamine, trimethylhexamethylenediamine, and 2-methylpentamethylenediamine, isophorone diamine. , 1,3-bisaminomethylcyclohexane, bis(4-aminocyclohexyl)methane, norbornenediamine, alicyclic polyamines such as 1,2-diaminocyclohexane, N-aminoethylpiperazine, 1,4-bis(2-amino -piperazine-type polyamines such as 2-methylpropyl)piperazine, diethyltoluenediamine, dimethylthiotoluenediamine, 4,4′-diamino-3,3′-diethyldiphenylmethane, bis(methylthio)toluenediamine, diaminodiphenylmethane, m- Aromatic polyamines such as phenylenediamine, diaminodiphenylsulfone, diethyltoluenediamine, trimethylenebis(4-aminobenzoate), and polytetramethyleneoxide-di-p-aminobenzoate can be exemplified. Commercially available products include Epicure-W, Epicure-Z (Yuka Shell Epoxy Co., Ltd., trade name), jER Cure (registered trademark)-W, jER Cure (registered trademark)-Z (Mitsubishi Chemical Co., Ltd., trade name). , Kayahard AA, Kayahard AB, Kayahard AS (Nippon Kayaku Co., Ltd., trade name), Thothamine HM-205 (Nippon Steel & Sumikin Chemical Co., Ltd., trade name), Adeka Hardner EH-101 (Co., Ltd. ADEKA, trade name), Epomic Q-640, Epomic Q-643 (Mitsui Chemicals, trade name), DETDA80 (Lonza, trade name), Thothamine HM-205 (Nippon Steel & Sumikin Chemical Co., Ltd., trade name), etc. is mentioned.
酸無水物系硬化剤は特に限定されないが、例えば、メチルテトラヒドロフタル酸無水物、メチルヘキサヒドロフタル酸無水物、アルキル化テトラヒドロフタル酸無水物、メチルハイミック酸無水物、アルケニル基で置換されたコハク酸無水物、グルタル酸無水物等が挙げられる。特に、3,4-ジメチル-6-(2-メチル-1-プロペニル)-1,2,3,6-テトラヒドロフタル酸無水物、1-イソプロピル-4-メチル-ビシクロ[2.2.2]オクト-5-エン-2,3-ジカルボン酸無水物、ノルボルナン-2,3-ジカルボン酸無水物、メチルノルボルナン-2,3-ジカルボン酸無水物、水素化メチルナジック酸無水物、アルケニル基で置換されたコハク酸無水物、ジエチルグルタル酸無水物が好ましい。
The acid anhydride-based curing agent is not particularly limited, but for example, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, methylhimic acid anhydride, alkenyl-substituted Succinic anhydride, glutaric anhydride and the like can be mentioned. especially 3,4-dimethyl-6-(2-methyl-1-propenyl)-1,2,3,6-tetrahydrophthalic anhydride, 1-isopropyl-4-methyl-bicyclo [2.2.2] Oct-5-ene-2,3-dicarboxylic anhydride, norbornane-2,3-dicarboxylic anhydride, methylnorbornane-2,3-dicarboxylic anhydride, hydrogenated methylnadic anhydride, substituted with alkenyl groups succinic anhydride and diethylglutaric anhydride are preferred.
フェノール系硬化剤はフェノール性水酸基を有するモノマー、オリゴマー、ポリマー全般をいい、例えば、フェノールノボラック樹脂およびそのアルキル化物またはアリル化物、クレゾールノボラック樹脂、フェノールアラルキル(フェニレン、ビフェニレン骨格を含む)樹脂、ナフトールアラルキル樹脂、トリフェノールメタン樹脂、ジシクロペンタジエン型フェノール樹脂等が挙げられる。中でも、アリルフェノールノボラック樹脂が好ましい。
Phenolic curing agents refer to monomers, oligomers, and polymers generally having phenolic hydroxyl groups, such as phenol novolac resins and their alkylated or allylated products, cresol novolak resins, phenol aralkyl (including phenylene and biphenylene skeleton) resins, and naphthol aralkyls. Resins, triphenol methane resins, dicyclopentadiene type phenol resins, and the like. Among them, allylphenol novolac resin is preferable.
チオール化合物には、加水分解性の多官能チオール化合物、非加水分解性の多官能チオール化合物が含まれる。
Thiol compounds include hydrolyzable polyfunctional thiol compounds and non-hydrolyzable polyfunctional thiol compounds.
加水分解性の多官能チオール化合物の例としては、トリメチロールプロパントリス(3-メルカプトプロピオネート)(SC有機化学社製:TMMP)、トリス-[(3-メルカプトプロピオニルオキシ)-エチル]-イソシアヌレート(SC有機化学社製:TEMPIC)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)(SC有機化学社製:PEMP)、テトラエチレングリコールビス(3-メルカプトプロピオネート)(SC有機化学社製:EGMP-4)、ジペンタエリスリトールヘキサキス(3-メルカプトプロピオネート)(SC有機化学社製:DPMP)、ペンタエリスリトールテトラキス(3-メルカプトブチレート)(昭和電工社製:カレンズMT(登録商標)PE1)、1,3,5-トリス(3-メルカプトブチリルオキシエチル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン(昭和電工社製:カレンズMT(登録商標)NR1)等を挙げることができる。
Examples of hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanate Nurate (manufactured by SC Organic Chemical Co., Ltd.: TEMPIC), pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: PEMP), tetraethylene glycol bis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.) : EGMP-4), dipentaerythritol hexakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: DPMP), pentaerythritol tetrakis (3-mercaptobutyrate) (manufactured by Showa Denko Co., Ltd.: Karenz MT (registered trademark) ) PE1), 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (manufactured by Showa Denko Co., Ltd.: Karenz MT (registered trademark) NR1) and the like can be mentioned.
非加水分解性多官能チオール化合物の例としては、1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリル(商品名:TS-G、四国化成工業社製)、(1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリル(商品名:C3 TS-G、四国化成工業社製)、1,3,4,6-テトラキス(メルカプトメチル)グリコールウリル、1,3,4,6-テトラキス(メルカプトメチル)-3a-メチルグリコールウリル、1,3,4,6-テトラキス(2-メルカプトエチル)-3a-メチルグリコールウリル、1,3,4,6-テトラキス(3-メルカプトプロピル)-3a-メチルグリコールウリル、1,3,4,6-テトラキス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、1,3,4,6-テトラキス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、1,3,4,6-テトラキス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、1,3,4,6-テトラキス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、1,3,4,6-テトラキス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、1,3,4,6-テトラキス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、ペンタエリスリトールトリプロパンチオール(商品名:PEPT、SC有機化学社製)、ペンタエリスリトールテトラプロパンチオール等が挙げられる。
Examples of non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluril (trade name: TS-G, manufactured by Shikoku Kasei Co., Ltd.), (1,3, 4,6-tetrakis(3-mercaptopropyl)glycoluril (trade name: C3 TS-G, manufactured by Shikoku Kasei Co., Ltd.), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4 ,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercapto Propyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-dimethylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a,6a - dimethyl glycol uril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a,6a-dimethyl glycol uril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-diphenyl glycol uril , 1,3,4,6-tetrakis(2-mercaptoethyl)-3a,6a-diphenylglycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a,6a-diphenylglycoluril, penta Erythritol trippropanethiol (trade name: PEPT, manufactured by SC Organic Chemical Co., Ltd.), pentaerythritol tetrapropanethiol, and the like can be mentioned.
非加水分解性多官能チオール化合物としては、分子内にスルフィド結合を2つ以上有する3官能以上のポリチオール化合物を使用することもできる。このようなチオール化合物としては、例えば、1,2,3-トリス(メルカプトメチルチオ)プロパン、1,2,3-トリス(2-メルカプトエチルチオ)プロパン、1,2,3-トリス(3-メルカプトプロピルチオ)プロパン、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、テトラキス(メルカプトメチルチオメチル)メタン、テトラキス(2-メルカプトエチルチオメチル)メタン、テトラキス(3-メルカプトプロピルチメチル)メタン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタン、1,1,5,5-テトラキス(メルカプトメチルチオ)-3-チアペンタン、1,1,6,6-テトラキス(メルカプトメチルチオ)-3,4-ジチアヘキサン、2,2-ビス(メルカプトメチルチオ)エタンチオール、3-メルカプトメチルチオ-1,7-ジメルカプト-2,6-ジチアヘプタン、3,6-ビス(メルカプトメチルチオ)-1,9-ジメルカプト-2,5,8-トリチアノナン、3-メルカプトメチルチオ-1,6-ジメルカプト-2,5-ジチアヘキサン、1,1,9,9-テトラキス(メルカプトメチルチオ)-5-(3,3-ビス(メルカプトメチルチオ)-1-チアプロピル)3,7-ジチアノナン、トリス(2,2-ビス(メルカプトメチルチオ)エチル)メタン、トリス(4,4-ビス(メルカプトメチルチオ)-2-チアブチル)メタン、テトラキス(2,2-ビス(メルカプトメチルチオ)エチル)メタン、テトラキス(4,4-ビス(メルカプトメチルチオ)-2-チアブチル)メタン、3,5,9,11-テトラキス(メルカプトメチルチオ)-1,13-ジメルカプト-2,6,8,12-テトラチアトリデカン、3,5,9,11,15,17-ヘキサキス(メルカプトメチルチオ)-1,19-ジメルカプト-2,6,8,12,14,18-ヘキサチアノナデカン、9-(2,2-ビス(メルカプトメチルチオ)エチル)-3,5,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,6,8,10,12,16-ヘキサチアヘプタデカン、3,4,8,9-テトラキス(メルカプトメチルチオ)-1,11-ジメルカプト-2,5,7,10-テトラチアウンデカン、3,4,8,9,13,14-ヘキサキス(メルカプトメチルチオ)-1,16-ジメルカプト-2,5,7,10,12,15-ヘキサチアヘキサデカン、8-[ビス(メルカプトメチルチオ)メチル]-3,4,12,13-テトラキス(メルカプトメチルチオ)-1,15-ジメルカプト-2,5,7,9,11,14-ヘキサチアペンタデカン、4,6-ビス[3,5-ビス(メルカプトメチルチオ)-7-メルカプト-2,6-ジチアヘプチルチオ]-1,3-ジチアン、4-[3,5-ビス(メルカプトメチルチオ)-7‐メルカプト-2,6-ジチアヘプチルチオ]-6-メルカプトメチルチオ-1,3-ジチアン、1,1-ビス[4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ]-1,3-ビス(メルカプトメチルチオ)プロパン、1-[4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ]-3-[2,2-ビス(メルカプトメチルチオ)エチル]-7,9-ビス(メルカプトメチルチオ)-2,4,6,10-テトラチアウンデカン、3-[2-(1,3-ジチエタニル)]メチル-7,9-ビス(メルカプトメチルチオ)-1,11-ジメルカプト-2,4,6,10-テトラチアウンデカン、9-[2-(1,3-ジチエタニル)]メチル-3,5,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,6,8,10,12,16-ヘキサチアヘプタデカン、3-[2-(1,3-ジチエタニル)]メチル-7,9,13,15-テトラキス(メルカプトメチルチオ)-1,17-ジメルカプト-2,4,6,10,12,16-ヘキサチアヘプタデカン等の脂肪族ポリチオール化合物;4,6-ビス[4-(6-メルカプトメチルチオ)-1,3-ジチアニルチオ]-6-[4-(6‐メルカプトメチルチオ)-1,3-ジチアニルチオ]-1,3-ジチアン、4-[3,4,8,9‐テトラキス(メルカプトメチルチオ)-11-メルカプト-2,5,7,10-テトラチアウンデシル]-5-メルカプトメチルチオ-1,3-ジチオラン、4,5-ビス[3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ]-1,3-ジチオラン、4-[3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ]-5-メルカプトメチルチオ-1,3-ジチオラン、4-[3-ビス(メルカプトメチルチオ)メチル-5,6-ビス(メルカプトメチルチオ)-8-メルカプト-2,4,7-トリチアオクチル]-5-メルカプトメチルチオ-1,3-ジチオラン、2-{ビス[3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ]メチル}-1,3-ジチエタン、2-[3,4-ビス(メルカプトメチルチオ)-6-メルカプト-2,5-ジチアヘキシルチオ]メルカプトメチルチオメチル-1,3-ジチエタン、2-[3,4,8,9-テトラキス(メルカプトメチルチオ)-11-メルカプト-2,5,7,10-テトラチアウンデシルチオ]メルカプトメチルチオメチル-1,3-ジチエタン、2-[3-ビス(メルカプトメチルチオ)メチル-5,6-ビス(メルカプトメチルチオ)-8-メルカプト-2,4,7-トリチアオクチル]メルカプトメチルチオメチル-1,3-ジチエタン、4-{1-[2-(1,3-ジチエタニル)]-3-メルカプト-2-チアプロピルチオ}-5-[1,2-ビス(メルカプトメチルチオ)-4-メルカプト-3-チアブチルチオ]-1,3-ジチオラン等の環式構造を有するポリチオール化合物が挙げられる。
As the non-hydrolyzable polyfunctional thiol compound, it is also possible to use a trifunctional or higher polythiol compound having two or more sulfide bonds in the molecule. Examples of such thiol compounds include 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercapto propylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,7- dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, tetrakis(mercaptomethylthiomethyl) Methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthymethyl)methane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercapto methylthio)ethane, 1,1,5,5-tetrakis(mercaptomethylthio)-3-thiapentane, 1,1,6,6-tetrakis(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio) ) ethanethiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis(mercaptomethylthio)-1,9-dimercapto-2,5,8-trithianone, 3-mercaptomethylthio- 1,6-dimercapto-2,5-dithiahexane, 1,1,9,9-tetrakis(mercaptomethylthio)-5-(3,3-bis(mercaptomethylthio)-1-thiapropyl)3,7-dithianone, tris (2,2-bis(mercaptomethylthio)ethyl)methane, tris(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, tetrakis(2,2-bis(mercaptomethylthio)ethyl)methane, tetrakis(4) , 4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetrakis(mercaptomethylthio)-1,13-dimercapto-2,6,8,12-tetrathiatridecane, 3, 5,9,11,15,17-hexakis(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathianonadecane, 9-(2,2-bis(mercaptomethylthio) ) ethyl)-3,5,13,15-tetrakis(mercaptomethylthio)- 1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3,4,8,9-tetrakis(mercaptomethylthio)-1,11-dimercapto-2,5,7,10 -tetrathiaundecane, 3,4,8,9,13,14-hexakis(mercaptomethylthio)-1,16-dimercapto-2,5,7,10,12,15-hexathiahexadecane, 8-[bis( mercaptomethylthio)methyl]-3,4,12,13-tetrakis(mercaptomethylthio)-1,15-dimercapto-2,5,7,9,11,14-hexathiapentadecane, 4,6-bis[3, 5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-1,3-dithiane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-di Thiaheptylthio]-6-mercaptomethylthio-1,3-dithiane, 1,1-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-bis(mercaptomethylthio)propane, 1 -[4-(6-mercaptomethylthio)-1,3-dithianylthio]-3-[2,2-bis(mercaptomethylthio)ethyl]-7,9-bis(mercaptomethylthio)-2,4,6,10 -tetrathiaundecane, 3-[2-(1,3-dithietanyl)]methyl-7,9-bis(mercaptomethylthio)-1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9- [2-(1,3-dithietanyl)]methyl-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3-[2-(1,3-dithietanyl)]methyl-7,9,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,4,6,10,12,16-hexathiahepta Aliphatic polythiol compounds such as decane; 4,6-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-6-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1 ,3-dithiane, 4-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7,10-tetrathiaundecyl]-5-mercaptomethylthio-1,3-dithiolane , 4,5-bis[3,4-bis(mercaptomethylthio)-6-mercapto-2 ,5-dithiahexylthio]-1,3-dithiolane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-5-mercaptomethylthio-1,3 -dithiolane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiooctyl]-5-mercaptomethylthio-1,3-dithiolane , 2-{bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-1,3-dithiethane, 2-[3,4-bis(mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7 , 10-tetrathiaundecylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7 -trithiaoctyl]mercaptomethylthiomethyl-1,3-dithietane, 4-{1-[2-(1,3-dithietanyl)]-3-mercapto-2-thiapropylthio}-5-[1,2- Examples include polythiol compounds having a cyclic structure such as bis(mercaptomethylthio)-4-mercapto-3-thiabutylthio]-1,3-dithiolane.
<樹脂組成物の構成割合>
樹脂組成物中の硬化触媒の割合は特に限定されないが、樹脂組成物中の熱硬化性樹脂に対して、0.01~50wt%であることが好ましく、0.01~30wt%であることがより好ましく、0.01~20wt%であることがさらに好ましい。 <Composition ratio of resin composition>
Although the ratio of the curing catalyst in the resin composition is not particularly limited, it is preferably 0.01 to 50 wt%, more preferably 0.01 to 30 wt%, relative to the thermosetting resin in the resin composition. More preferably, it is 0.01 to 20 wt%.
樹脂組成物中の硬化触媒の割合は特に限定されないが、樹脂組成物中の熱硬化性樹脂に対して、0.01~50wt%であることが好ましく、0.01~30wt%であることがより好ましく、0.01~20wt%であることがさらに好ましい。 <Composition ratio of resin composition>
Although the ratio of the curing catalyst in the resin composition is not particularly limited, it is preferably 0.01 to 50 wt%, more preferably 0.01 to 30 wt%, relative to the thermosetting resin in the resin composition. More preferably, it is 0.01 to 20 wt%.
樹脂組成物の増粘倍率が初期の2倍になるまでの時間をポットライフとし、エポキシ-チオール硬化系におけるポットライフは、8時間以上であることが好ましく、12時間以上であることがより好ましく、24時間以上であることがさらに好ましい。その他の硬化系においても、ポットライフは長い方が安定性の観点から好ましい。
The pot life is defined as the time until the thickening ratio of the resin composition doubles from the initial value, and the pot life in the epoxy-thiol curing system is preferably 8 hours or longer, more preferably 12 hours or longer. , more preferably 24 hours or longer. Also in other curing systems, a longer pot life is preferable from the viewpoint of stability.
<樹脂組成物のそのほかの成分>
本開示の硬化性組成物は、主剤、硬化触媒、硬化剤以外に、例えば以下に述べるものを必要に応じて含有してもよい。 <Other components of the resin composition>
The curable composition of the present disclosure may optionally contain, for example, the following in addition to the main agent, curing catalyst, and curing agent.
本開示の硬化性組成物は、主剤、硬化触媒、硬化剤以外に、例えば以下に述べるものを必要に応じて含有してもよい。 <Other components of the resin composition>
The curable composition of the present disclosure may optionally contain, for example, the following in addition to the main agent, curing catalyst, and curing agent.
(1)安定剤
本開示の樹脂組成物には、その貯蔵安定性を向上させ、ポットライフを長くするために、安定剤を添加することができる。エポキシ樹脂を主剤とする一液型接着剤の安定剤として公知の種々の安定剤を使用することができるが、液状ホウ酸エステル化合物、アルミキレート及び有機酸からなる群から選択される少なくとも1つが好ましい。 (1) Stabilizer A stabilizer can be added to the resin composition of the present disclosure in order to improve its storage stability and prolong its pot life. Various known stabilizers can be used as stabilizers for one-component adhesives based on epoxy resins. preferable.
本開示の樹脂組成物には、その貯蔵安定性を向上させ、ポットライフを長くするために、安定剤を添加することができる。エポキシ樹脂を主剤とする一液型接着剤の安定剤として公知の種々の安定剤を使用することができるが、液状ホウ酸エステル化合物、アルミキレート及び有機酸からなる群から選択される少なくとも1つが好ましい。 (1) Stabilizer A stabilizer can be added to the resin composition of the present disclosure in order to improve its storage stability and prolong its pot life. Various known stabilizers can be used as stabilizers for one-component adhesives based on epoxy resins. preferable.
液状ホウ酸エステル化合物の例としては、2,2'-オキシビス(5,5'-ジメチル-1,3,2-オキサボリナン)、トリメチルボレート、トリエチルボレート、トリ-nプロピルボレート、トリイソプロピルボレート、トリ-n-ブチルボレート、トリペンチルボレート、トリアリルボレート、トリヘキシルボレート、トリシクロヘキシルボレート、トリオクチルボレート、トリノニルボレート、トリデシルボレート、トリドデシルボレート、トリヘキサデシルボレート、トリオクタデシルボレート、トリス(2-エチルヘキシロキシ)ボラン、ビス(1,4,7,10-テトラオキサウンデシル)(1,4,7,10,13-ペンタオキサテトラデシル)(1,4,7-トリオキサウンデシル)ボラン、トリベンジルボレート、トリフェニルボレート、トリ-o-トリルボレート、トリ-m-トリルボレート、トリエタノールアミンボレート等が挙げられる。
Examples of liquid borate compounds include 2,2′-oxybis(5,5′-dimethyl-1,3,2-oxaborinane), trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, tri - n-butylborate, tripentylborate, triallylborate, trihexylborate, tricyclohexylborate, trioctylborate, trinonylborate, tridecylborate, tridodecylborate, trihexadecylborate, trioctadecylborate, tris(2 -ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentoxatetradecyl)(1,4,7-trioxaundecyl) Borane, tribenzylborate, triphenylborate, tri-o-tolylborate, tri-m-tolylborate, triethanolamineborate and the like.
アルミキレートとしては、例えばアルミキレートA(川研ファインケミカル株式会社製)を用いることができる。有機酸としては、例えばバルビツール酸を用いることができる。
As the aluminum chelate, for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used. As an organic acid, for example, barbituric acid can be used.
(2)充填剤
本開示の樹脂組成物には、充填剤を添加することができる。
充填剤の具体的な例としては、シリカフィラー、ガラスフィラー、アルミナフィラー、酸化チタンフィラー、窒化ホウ素フィラー、窒化アルミフィラー、タルクフィラー、炭酸カルシウムフィラー、樹脂フィラー(例えば、ポリテトラフルオロエチレン(PTFE)フィラー、シリコーンゴムフィラーなど)、銀や銅やニッケルなどの導電性フィラー等が挙げられる。形状は特に限られず、中空状であっても、球状であっても、不定形であってもよい。また、充填剤は、表面処理されたものであってもよい。 (2) Filler A filler can be added to the resin composition of the present disclosure.
Specific examples of fillers include silica fillers, glass fillers, alumina fillers, titanium oxide fillers, boron nitride fillers, aluminum nitride fillers, talc fillers, calcium carbonate fillers, resin fillers (e.g., polytetrafluoroethylene (PTFE) fillers, silicone rubber fillers, etc.), conductive fillers such as silver, copper and nickel. The shape is not particularly limited, and may be hollow, spherical, or amorphous. Moreover, the filler may be surface-treated.
本開示の樹脂組成物には、充填剤を添加することができる。
充填剤の具体的な例としては、シリカフィラー、ガラスフィラー、アルミナフィラー、酸化チタンフィラー、窒化ホウ素フィラー、窒化アルミフィラー、タルクフィラー、炭酸カルシウムフィラー、樹脂フィラー(例えば、ポリテトラフルオロエチレン(PTFE)フィラー、シリコーンゴムフィラーなど)、銀や銅やニッケルなどの導電性フィラー等が挙げられる。形状は特に限られず、中空状であっても、球状であっても、不定形であってもよい。また、充填剤は、表面処理されたものであってもよい。 (2) Filler A filler can be added to the resin composition of the present disclosure.
Specific examples of fillers include silica fillers, glass fillers, alumina fillers, titanium oxide fillers, boron nitride fillers, aluminum nitride fillers, talc fillers, calcium carbonate fillers, resin fillers (e.g., polytetrafluoroethylene (PTFE) fillers, silicone rubber fillers, etc.), conductive fillers such as silver, copper and nickel. The shape is not particularly limited, and may be hollow, spherical, or amorphous. Moreover, the filler may be surface-treated.
(3)カップリング剤
本開示の樹脂組成物には、カップリング剤を添加することができる。カップリング剤は、シランカップリング剤が好ましく、エポキシ系、アミノ系、ビニル系、メタクリル系、アクリル系、メルカプト系等の各種シランカップリング剤を用いることができる。これらのシランカップリング剤は、単独で用いても、2種以上を併用してもよい。 (3) Coupling agent A coupling agent can be added to the resin composition of the present disclosure. The coupling agent is preferably a silane coupling agent, and various silane coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto can be used. These silane coupling agents may be used alone or in combination of two or more.
本開示の樹脂組成物には、カップリング剤を添加することができる。カップリング剤は、シランカップリング剤が好ましく、エポキシ系、アミノ系、ビニル系、メタクリル系、アクリル系、メルカプト系等の各種シランカップリング剤を用いることができる。これらのシランカップリング剤は、単独で用いても、2種以上を併用してもよい。 (3) Coupling agent A coupling agent can be added to the resin composition of the present disclosure. The coupling agent is preferably a silane coupling agent, and various silane coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto can be used. These silane coupling agents may be used alone or in combination of two or more.
シランカップリング剤としては、例えば、アルケニル基を有するシランカップリング剤として、ビニルトリメトキシシラン(市販品としては信越化学工業社製;KBM-1003、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-171、東レ・ダウコーニング社製;Z-6300、旭化成ワッカーシリコーン社製;GENIOSIL XL10、日美商事社製;サイラエースS210等が挙げられる)、ビニルトリエトキシシラン(市販品としては信越化学工業社製;KBE-1003、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-151、東レ・ダウコーニング社製;Z-6519、旭化成ワッカーシリコーン社製;GENIOSIL GF56、日美商事社製;サイラエースS220等が挙げられる)、ビニルトリアセトキシシラン(市販品としては旭化成ワッカーシリコーン社製;GENIOSIL GF62が挙げられる)、ビニルトリス(2-メトキシエトキシ)シラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-172が挙げられる)、ビニルメチルジメトキシシラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-2171、旭化成ワッカーシリコーン社製;GENIOSIL XL12等が挙げられる)、オクテニルトリメトキシシラン(市販品としては信越化学工業社製;KBM-1083が挙げられる)、アリルトリメトキシシラン(市販品として東レ・ダウコーニング社製;Z-6825が挙げられる)、p-スチリルトリメトキシシラン(市販品としては信越化学工業社製;KBM-1403等が挙げられる)。例えば、アクリル基を有するシランカップリング剤として、3-アクリロキシプロピルトリメトキシシラン、3-アクリロキシプロピルトリエトキシシラン(市販品としては信越化学工業社製;KBM-5103等が挙げられる)等が挙げられ、メタクリル基を有するシランカップリング剤として、3-メタクリロキシプロピルメチルジメトキシシラン(市販品としては信越化学工業社製;KBM-502、東レ・ダウコーニング社製;Z-6033等が挙げられる)、3-メタクリロキシプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-503、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-174、東レ・ダウコーニング社製;Z-6030、旭化成ワッカーシリコーン社製;GENIOSIL GF31、日美商事社製;サイラエースS710等が挙げられる)、3-メタクリロキシプロピルメチルジエトキシシラン(市販品としては信越化学工業社製;KBE-502が挙げられる)、3-メタクリロキシプロピルトリエトキシシラン(信越化学工業社製;KBE-503、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;Y-9936が挙げられる)、メタクリロキシオクチルトリメトキシシラン(信越化学工業社製;KBM-5803が挙げられる)等が挙げられ、エポキシ基を有するシランカップリング剤として、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン(市販品としては信越化学工業社製;KBM-303、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-186、東レ・ダウコーニング社製;Z-6043、日美商事社製;サイラエースS530等が挙げられる)、3-グリシドキシプロピルメチルジメトキシシラン(市販品としては信越化学工業社製;KBM-402、東レ・ダウコーニング社製;Z-6044、日美商事社製;サイラエースS520等が挙げられる)、3-グリシドキシプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-403、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-187、東レ・ダウコーニング社製;Z-6040、旭化成ワッカーシリコーン社製;GENIOSIL GF80、日美商事社製サイラエースS510等が挙げられる)、3-グリシドキシプロピルメチルジエトキシシラン(市販品としては信越化学工業社製;KBE-402が挙げられる)、3-グリシドキシプロピルトリエトキシシラン(市販品としては信越化学工業社製;KBE-403、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1871、旭化成ワッカーシリコーン社製;GENIOSIL GF82等が挙げられる)、グリシドキシオクチルトリメトキシシラン(市販品としては信越化学工業社製;KBM-4803が挙げられる)等が挙げられ、アミノ基を有するシランカップリング剤として、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン(信越化学工業社製;KBM-602、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-2120、旭化成ワッカーシリコーン社製;GENIOSIL GF-95、日美商事社製;サイラエースS310等が挙げられる)、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-603、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1120、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1122、東レ・ダウコーニング社製;Z-6020、東レ・ダウコーニング社製;Z-6094、旭化成ワッカーシリコーン社製;GENIOSIL GF-91、日美商事社製;サイラエースS320等が挙げられる)、3-アミノプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-903、モメンティブ・パフォーマンス・マテリアルズ・ジャパン製;A-1110、東レ・ダウコーニング株式会社製;Z-6610、日美商事社製;サイラエースS360等が挙げられる)、3-アミノプロピルトリエトキシシラン(市販品としては信越化学工業社製;KBE-903、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1100、東レ・ダウコーニング社製;Z-6011、日美商事社製;サイラエースS330等が挙げられる)、3-トリエトキシシリル-N-(1,3-ジメチル-ブチリデン)プロピルアミン(市販品としては信越化学工業社製;KBE-9103、日美商事社製のサイラエースS340等が挙げられる)、N-フェニル-3-アミノプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-573、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;Y-9669、東レ・ダウコーニング社製;Z-6883等が挙げられる)、N,N’-ビス[3-(トリメトキシシリル)プロピル]エチレンジアミン(市販品としては日美商事社製;サイラエースXS1003が挙げられる)、N-(ビニルベンジル)-2-アミノエチル-3-アミノプロピルトリメトキシシランの塩酸塩(市販品としては信越化学工業社製;KBM-575、東レ・ダウコーニング社製;Z-6032、日美商事社製;サイラエースS350等が挙げられる)等が挙げられ、イソシアヌレート基を有するシランカップリング剤として、トリス-(トリメトキシシリルプロピル)イソシアヌレート(市販品としては信越化学工業社製のKBM-9659が挙げられる)が挙げられ、メルカプト基を有するシランカップリング剤として、3-メルカプトプロピルメチルジメトキシシラン(市販品としては信越化学工業社製;KBM-802、東レ・ダウコーニング社製;Z-6852等が挙げられる)、3-メルカプトプロピルトリメトキシシラン(市販品としては信越化学工業社製;KBM-803、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-189、東レ・ダウコーニング社製;Z-6062、日美商事社製;サイラエースS810等が挙げられる)、3-メルカプトプロピルトリエトキシシラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1891、東レ・ダウコーニング社製;Z-6911が挙げられる)等が挙げられ、ウレイド基を有するシランカップリング剤として、3-ウレイドプロピルトリアルコキシシラン(市販品として信越化学工業社製;KBE-585が挙げられ)、3-ウレイドプロピルトリメトキシシラン、3-ウレイドプロピルトリエトキシシラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1160が挙げられる)等が挙げられ、スルフィド基を有するシランカップリング剤として、ビス(トリエトキシシリルプロピル)テトラスルフィドが挙げられ、チオエステル基を有するシランカップリング剤として、3-オクタノイルチオ-1-プロピルトリエトキシシラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-LINK599が挙げられる)が挙げられ、イソシアネート基を有するシランカップリング剤として、3-イソシアネートプロピルトリエトキシシラン(市販品としては信越化学工業社製;KBE-9007、モメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;A-1310等が挙げられる)、3-イソシアネートプロピルトリメトキシシラン(市販品としてはモメンティブ・パフォーマンス・マテリアルズ・ジャパン社製;Y-5187、旭化成ワッカーシリコーン社製;GENIOSIL GF40等が挙げられる)等が挙げられる。
Silane coupling agents include, for example, vinyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-1003, Momentive Performance Materials Japan Co., Ltd.; A -171, Dow Corning Toray Co., Ltd.; Z-6300, Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL XL10, Himi Shoji Co., Ltd.; KBE-1003, Momentive Performance Materials Japan; A-151, Dow Corning Toray; Z-6519, Asahi Kasei Wacker Silicone; GENIOSIL GF56, Himi Shoji; Sila Ace S220, etc. ), vinyltriacetoxysilane (commercially available from Asahi Kasei Wacker Silicone; GENIOSIL GF62), vinyltris(2-methoxyethoxy)silane (commercially available from Momentive Performance Materials Japan) A-172), vinylmethyldimethoxysilane (commercially available products include Momentive Performance Materials Japan; A-2171, Asahi Kasei Wacker Silicone; GENIOSIL XL12, etc.), octenyltri Methoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; includes KBM-1083), allyltrimethoxysilane (commercially available from Dow Corning Toray; includes Z-6825), p-styryltrimethoxysilane (Commercially available products include KBM-1403 manufactured by Shin-Etsu Chemical Co., Ltd.). For example, silane coupling agents having an acrylic group include 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-5103, etc.), and the like. and silane coupling agents having a methacryl group include 3-methacryloxypropylmethyldimethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-502, Toray Dow Corning Co., Ltd.; Z-6033, etc.). ), 3-methacryloxypropyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-503, Momentive Performance Materials Japan Co., Ltd.; A-174, Dow Corning Toray Co., Ltd.; Z-6030 , Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF31, Himi Shoji Co., Ltd.; Sila Ace S710, etc.), 3-methacryloxypropylmethyldiethoxysilane (commercially available products include Shin-Etsu Chemical Co., Ltd.; KBE-502. ), 3-methacryloxypropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.; KBE-503, Momentive Performance Materials Japan; Y-9936), methacryloxyoctyltrimethoxysilane (Shin-Etsu Chemical manufactured by KBM-5803) and the like, and as a silane coupling agent having an epoxy group, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-303, manufactured by Momentive Performance Materials Japan; A-186, manufactured by Dow Corning Toray; Z-6043, manufactured by Himi Shoji; Sila Ace S530, etc.), 3-glycidoxypropyl Methyldimethoxysilane (commercially available products include KBM-402 manufactured by Shin-Etsu Chemical Co., Ltd.; Z-6044 manufactured by Dow Corning Toray; Methoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-403, Momentive Performance Materials Japan Co., Ltd.; A-187, Dow Corning Toray Co., Ltd.; Z-6040, Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF80, Sila Ace S510 manufactured by Himi Shoji Co., Ltd.), 3-glycidoxypropylmethyldiethoxysilane (commercially available is manufactured by Shin-Etsu Chemical Co., Ltd.; includes KBE-402), 3-glycidoxypropyltriethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBE-403, manufactured by Momentive Performance Materials Japan; A-1871, manufactured by Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF82, etc.), glycidoxyoctyltrimethoxysilane (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-4803 is included), etc., and amino groups. as a silane coupling agent having N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-602; Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-95, Himi Shoji Co.; Sila Ace S310, etc.), N-2-(aminoethyl)-3-aminopropyltrimethoxysilane (commercially available from Shin-Etsu Chemical KBM-603, Momentive Performance Materials Japan; A-1120, Momentive Performance Materials Japan; A-1122, Dow Corning Toray; Z-6020, Dow Toray Z-6094 manufactured by Corning Corporation; Z-6094 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.; GENIOSIL GF-91 manufactured by Himi Shoji Co.; KBM-903, manufactured by Momentive Performance Materials Japan; A-1110, manufactured by Dow Corning Toray Co., Ltd.; Z-6610, manufactured by Himi Shoji Co., Ltd.; Ethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBE-903, Momentive Performance Materials Japan Co., Ltd.; A-1100, Dow Corning Toray Co., Ltd.; Z-6011, Himi Shoji Co., Ltd.; Sila Ace S330, etc.), 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine (commercially available products: KBE-9103 manufactured by Shin-Etsu Chemical Co., Ltd., Sila Ace S340 manufactured by Himi Shoji Co., Ltd., etc.) ), N-phenyl-3-aminopropyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-573, Momentive Performance, Y-9669 manufactured by Materials Japan Co., Ltd., Z-6883 manufactured by Dow Corning Toray Co., Ltd.), N,N'-bis[3-(trimethoxysilyl)propyl]ethylenediamine (commercially available in Japan Sila Ace XS1003 manufactured by Mishoji Co., Ltd.), N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane hydrochloride (commercially available products manufactured by Shin-Etsu Chemical Co., Ltd.; KBM-575, Toray・ Dow Corning Co., Ltd.; Z-6032, Nimi Shoji Co., Ltd.; Sila Ace S350, etc.), etc., and as a silane coupling agent having an isocyanurate group, tris-(trimethoxysilylpropyl) isocyanurate ( Commercially available products include KBM-9659 manufactured by Shin-Etsu Chemical Co., Ltd.), and as a silane coupling agent having a mercapto group, 3-mercaptopropylmethyldimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM -802, manufactured by Dow Corning Toray; Z-6852, etc.), 3-mercaptopropyltrimethoxysilane (commercially available from Shin-Etsu Chemical Co., Ltd.; KBM-803, Momentive Performance Materials Japan) A-189, manufactured by Dow Corning Toray Co., Ltd.; Z-6062, manufactured by Himi Shoji Co., Ltd.; Japan Co.; A-1891, Dow Corning Toray; Z-6911) and the like, and as a silane coupling agent having a ureido group, 3-ureidopropyltrialkoxysilane (commercially available from Shin-Etsu Chemical manufactured by Kogyo Co., Ltd.; includes KBE-585), 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane (commercially available products manufactured by Momentive Performance Materials Japan; includes A-1160) Examples of the silane coupling agent having a sulfide group include bis(triethoxysilylpropyl) tetrasulfide, and examples of the silane coupling agent having a thioester group include 3-octanoylthio-1-propyltriethoxysilane (commercially available products manufactured by Momentive Performance Materials Japan; As a coupling agent, 3-isocyanatopropyltriethoxysilane (commercially available products include Shin-Etsu Chemical Co., Ltd.; KBE-9007, Momentive Performance Materials Japan; A-1310, etc.), 3- Isocyanatopropyltrimethoxysilane (commercially available products include Y-5187 manufactured by Momentive Performance Materials Japan, and GENIOSIL GF40 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.).
(4)その他の添加剤
本開示の樹脂組成物には、本発明の目的を損なわない範囲で、その他の添加剤、例えばカーボンブラック、チタンブラック、イオントラップ剤、レベリング剤、酸化防止剤、消泡剤、揺変剤、粘度調整剤、難燃剤、着色剤、溶剤等を添加することができる。各添加剤の種類、添加量は常法通りである。 (4) Other Additives The resin composition of the present disclosure may contain other additives such as carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, digestive agents, etc., within a range that does not impair the object of the present invention. Foaming agents, thixotropic agents, viscosity modifiers, flame retardants, coloring agents, solvents and the like can be added. The type and amount of each additive are as per conventional methods.
本開示の樹脂組成物には、本発明の目的を損なわない範囲で、その他の添加剤、例えばカーボンブラック、チタンブラック、イオントラップ剤、レベリング剤、酸化防止剤、消泡剤、揺変剤、粘度調整剤、難燃剤、着色剤、溶剤等を添加することができる。各添加剤の種類、添加量は常法通りである。 (4) Other Additives The resin composition of the present disclosure may contain other additives such as carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, digestive agents, etc., within a range that does not impair the object of the present invention. Foaming agents, thixotropic agents, viscosity modifiers, flame retardants, coloring agents, solvents and the like can be added. The type and amount of each additive are as per conventional methods.
==樹脂組成物の利用方法==
本明細書に開示の樹脂組成物は、例えば、電子部品用の封止材や充填材、ダム材、導電性あるいは絶縁性の接着剤、ダイアタッチ材、フィルム、コート剤、シールド材などに利用できる。他にも塗料、パイプ用材、タンク用材などの複合材料、床材、メンブレンなどの土木建築材料、接着剤、などに用いることができるが、利用方法はこれらに限定されない。 == How to use the resin composition ==
The resin composition disclosed herein can be used, for example, as sealing materials and fillers for electronic components, dam materials, conductive or insulating adhesives, die attach materials, films, coating agents, shielding materials, and the like. can. In addition, it can be used for paints, composite materials such as pipe materials and tank materials, floor materials, civil engineering and construction materials such as membranes, adhesives, and the like, but the usage is not limited to these.
本明細書に開示の樹脂組成物は、例えば、電子部品用の封止材や充填材、ダム材、導電性あるいは絶縁性の接着剤、ダイアタッチ材、フィルム、コート剤、シールド材などに利用できる。他にも塗料、パイプ用材、タンク用材などの複合材料、床材、メンブレンなどの土木建築材料、接着剤、などに用いることができるが、利用方法はこれらに限定されない。 == How to use the resin composition ==
The resin composition disclosed herein can be used, for example, as sealing materials and fillers for electronic components, dam materials, conductive or insulating adhesives, die attach materials, films, coating agents, shielding materials, and the like. can. In addition, it can be used for paints, composite materials such as pipe materials and tank materials, floor materials, civil engineering and construction materials such as membranes, adhesives, and the like, but the usage is not limited to these.
==化合物の合成方法==
(化合物1)2-[2-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneの合成
DMA(ジメチルアセトアミド)(200g)とマグネチックスターラーの入っている反応容器に、キュアゾール2MZ-H(四国化成工業社製、39.9g、0.486mol)を撹拌しながら加え、60℃に加熱して溶解させた。得られた溶液にデナコールEX-731(ナガセケムテックス社製、100g、0.363mmol)を約10分間かけて少しずつ加えた。全て溶解後、70℃まで加熱し、同じ温度で6時間撹拌した。常温まで冷却後、水(約200mL)を加えて撹拌し、結晶を析出させた。生じた固体を吸引ろ過し、水で2回、IPAで2回、洗浄した後、乾燥させ、化合物1(85.7g)(回収率61%)を得た。生成物の物性測定値は以下の通りである。
==Method for Synthesizing Compounds==
(Compound 1) Synthesis of 2-[2-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione
Curesol 2MZ-H (manufactured by Shikoku Kasei Kogyo Co., Ltd., 39.9 g, 0.486 mol) was added with stirring to a reaction vessel containing DMA (dimethylacetamide) (200 g) and a magnetic stirrer, and heated to 60°C. to dissolve. Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 100 g, 0.363 mmol) was gradually added to the resulting solution over about 10 minutes. After dissolving everything, the mixture was heated to 70° C. and stirred at the same temperature for 6 hours. After cooling to room temperature, water (about 200 mL) was added and stirred to precipitate crystals. The resulting solid was suction filtered, washed twice with water and twice with IPA, and then dried to obtain compound 1 (85.7 g) (61% recovery). The measured physical properties of the product are as follows.
(化合物1)2-[2-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneの合成
(Compound 1) Synthesis of 2-[2-hydroxy-3-(2-methyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione
1H NMR(DMSO-d6): 7.89-7.78ppm (m, 4H), 7.05ppm (s, 1H), 6.67ppm (s, 1), 5.37ppm (d, 4.8Hz, 1H), 4.08-3.95ppm (m, 2H), 3.83 (dd, 8.6Hz, 15Hz, 1H), 3.62ppm (dd, 7.6Hz, 13.6Hz, 1H), 3.57ppm (dd, 4.8Hz, 13.6Hz, 1H), 2.26ppm (s, 3H)
1 H NMR(DMSO-d6): 7.89-7.78ppm (m, 4H), 7.05ppm (s, 1H), 6.67ppm (s, 1), 5.37ppm (d, 4.8Hz, 1H), 4.08-3.95ppm (m, 2H), 3.83 (dd, 8.6Hz, 15Hz, 1H), 3.62ppm (dd, 7.6Hz, 13.6Hz, 1H), 3.57ppm (dd, 4.8Hz, 13.6Hz, 1H), 2.26ppm (s , 3H)
(化合物2)2-[2-hydroxy-3-(1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione(CAS登録番号:112086-61-0)の合成
DMA(10mL)の入っている反応容器に、キュアゾールSIZ(四国化成工業社製、1.65g、24.3mmol)をスターラーで撹拌しながら加え、60℃に加熱して溶解させた。得られた溶液にデナコールEX-731(ナガセケムテックス社製、5.00g、23.1mmol)を5分間かけて少しずつ加えた。全て溶解後、70℃まで加熱し、同じ温度で6時間撹拌した。常温まで冷却後、水(約15mL)を加え15℃にて撹拌し、結晶を析出させた。生じた固体を吸引ろ過して水で洗浄した後、乾燥させ、固体として化合物2(3.69g)を得た。生成物の物性測定値は以下の通りである。
(Compound 2) Synthesis of 2-[2-hydroxy-3-(1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione (CAS Registry Number: 112086-61-0)
Curesol SIZ (manufactured by Shikoku Kasei Kogyo Co., Ltd., 1.65 g, 24.3 mmol) was added to a reaction vessel containing DMA (10 mL) while stirring with a stirrer, and dissolved by heating to 60°C. Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 5.00 g, 23.1 mmol) was gradually added to the obtained solution over 5 minutes. After dissolving everything, the mixture was heated to 70° C. and stirred at the same temperature for 6 hours. After cooling to room temperature, water (about 15 mL) was added and the mixture was stirred at 15°C to precipitate crystals. The resulting solid was filtered by suction, washed with water, and dried to obtain compound 2 (3.69 g) as a solid. The measured physical properties of the product are as follows.
1H NMR (400 MHz DMSO-d6): 7.93-7.77ppm (m, 4H), 7.58ppm (s, 1H), 7.16ppm (s, 1H), 6.84ppm (s, 1H), 5.41ppm (d, 5.6 Hz), 4.11ppm (dd, 3.2Hz, 13.6Hz, 1H), 4.04-3.94ppm (m, 1H), 3.89ppm (dd, 7.2Hz, 14Hz, 1H), 3.60-3.47ppm (m, 2H)
1 H NMR (400 MHz DMSO-d6): 7.93-7.77ppm (m, 4H), 7.58ppm (s, 1H), 7.16ppm (s, 1H), 6.84ppm (s, 1H), 5.41ppm (d, 5.6Hz), 4.11ppm (dd, 3.2Hz, 13.6Hz, 1H), 4.04-3.94ppm (m, 1H), 3.89ppm (dd, 7.2Hz, 14Hz, 1H), 3.60-3.47ppm (m, 2H)
(化合物3)2-[2-hydroxy-3-(2-phenyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneの合成
DMA(10mL)の入っている反応容器に、キュアゾール2PZ-PW(四国化成工業社製、3.50g、24.3mmol)をスターラーで撹拌しながら加え、60℃に加熱して溶解させた。得られた溶液にデナコールEX-731(ナガセケムテックス社製、5.00g、23.1mmol)を5分間かけて少しずつ加えた。全て溶解後、70℃まで加熱し、同じ温度で23時間撹拌した。常温まで冷却した後、水(約15mL)を加えて15℃で撹拌し、結晶を析出させた。生じた固体を吸引ろ過して水で洗浄後、乾燥させ、粗結晶4.04gを得た。
(Compound 3) Synthesis of 2-[2-hydroxy-3-(2-phenyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione
Curesol 2PZ-PW (manufactured by Shikoku Kasei Kogyo Co., Ltd., 3.50 g, 24.3 mmol) was added to a reaction vessel containing DMA (10 mL) while stirring with a stirrer, and heated to 60° C. to dissolve. Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 5.00 g, 23.1 mmol) was gradually added to the obtained solution over 5 minutes. After all was dissolved, the mixture was heated to 70° C. and stirred at the same temperature for 23 hours. After cooling to room temperature, water (about 15 mL) was added and the mixture was stirred at 15°C to precipitate crystals. The resulting solid was filtered by suction, washed with water, and dried to obtain 4.04 g of crude crystals.
粗結晶3.00gに0.5N塩酸1.7mLを加え、乳鉢ですり潰し、得られた粉体に水を加えて懸濁させた。得られた懸濁液を吸引ろ過し、固体をクロロホルム(約50mL)に溶解させて分液ロートに移し、得られた溶液を、水-飽和重曹水-食塩水で、この順に洗浄した。クロロホルム層を硫酸ナトリウムで脱水したのち、液相分離ろ紙でろ過し、有機層をロータリーエバポレーターで濃縮した。得られたオレンジ色の油状物に酢酸エチルおよびヘキサンを加えて結晶化させ、結晶を吸引ろ過した後、減圧乾燥することで、固体として化合物3(1.33g)を得た。生成物の物性測定値は以下の通りである。
1.7 mL of 0.5N hydrochloric acid was added to 3.00 g of the crude crystals and ground in a mortar, and water was added to the resulting powder to suspend it. The resulting suspension was suction filtered, the solid was dissolved in chloroform (about 50 mL) and transferred to a separating funnel, and the resulting solution was washed with water-saturated sodium bicarbonate solution-brine in this order. After the chloroform layer was dehydrated with sodium sulfate, it was filtered through liquid phase separation filter paper, and the organic layer was concentrated with a rotary evaporator. Ethyl acetate and hexane were added to the resulting orange oil to crystallize, and the crystals were suction-filtered and dried under reduced pressure to obtain compound 3 (1.33 g) as a solid. The measured physical properties of the product are as follows.
1H NMR (400 MHz DMSO-d6) : 7.90-7.79ppm (m, 4H), 7.63-7.54ppm (m, 2H), 7.39-7.26 (m, 4H), 6.97ppm (s, 1H), 5.54ppm (d, 5.6Hz, 1H), 4.17-3.92ppm (m, 3H), 3.57ppm (dd, 6.8Hz, 13.6Hz, 1H), 3.45ppm (dd, 5.6Hz, 13.6Hz, 1H)
1 H NMR (400 MHz DMSO-d6) : 7.90-7.79ppm (m, 4H), 7.63-7.54ppm (m, 2H), 7.39-7.26 (m, 4H), 6.97ppm (s, 1H), 5.54ppm (d, 5.6Hz, 1H), 4.17-3.92ppm (m, 3H), 3.57ppm (dd, 6.8Hz, 13.6Hz, 1H), 3.45ppm (dd, 5.6Hz, 13.6Hz, 1H)
(化合物4)2-[2-hydroxy-3-(2-undecyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneの合成
DMA(15mL)の入っている反応容器に、キュアゾールC11Z(四国化成工業社製、5.14g、24.3mmol)をスターラーで撹拌しながら加え、60℃に加熱して溶解させた。得られた溶解液にデナコールEX-731(ナガセケムテックス社製、5.00g、23.1mmol)を5分間かけて少しずつ加えた。全てが溶解した後、70℃まで加熱し、同じ温度で23時間撹拌した。常温まで冷却後、水(約20mL)を加えて15℃で撹拌し、結晶を析出させた。得られた結晶を吸引ろ過し、水で洗浄後、乾燥させ粗結晶5.70gを得た。
(Compound 4) Synthesis of 2-[2-hydroxy-3-(2-undecyl-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione
Curesol C11Z (manufactured by Shikoku Kasei Kogyo Co., Ltd., 5.14 g, 24.3 mmol) was added to a reaction vessel containing DMA (15 mL) while stirring with a stirrer, and heated to 60° C. to dissolve. Denacol EX-731 (manufactured by Nagase ChemteX Corporation, 5.00 g, 23.1 mmol) was added little by little to the resulting solution over 5 minutes. After everything was dissolved, it was heated to 70° C. and stirred at the same temperature for 23 hours. After cooling to room temperature, water (approximately 20 mL) was added and the mixture was stirred at 15°C to precipitate crystals. The obtained crystals were suction-filtered, washed with water, and dried to obtain 5.70 g of crude crystals.
粗結晶3.00gに1N塩酸1.8mLを加え、乳鉢ですり潰し、得られた粉体に水を加えて懸濁させた。得られた懸濁液を吸引ろ過し、固体をクロロホルム(約50mL)に溶解させて分液ロートに移し、得られた溶液を、水-飽和重曹水-食塩水で、この順に洗浄した。クロロホルム層を硫酸マグネシウムで脱水したのち、液相分離ろ紙でろ過し、有機層をロータリーエバポレーターで濃縮した。得られた白色固体に酢酸エチルおよびヘキサンを加えて懸濁させたのち、懸濁液を吸引ろ過し、得られた結晶減圧乾燥することで、化合物4(1.97g)を得た。生成物の物性測定値は以下の通りである。
1.8 mL of 1N hydrochloric acid was added to 3.00 g of crude crystals and ground in a mortar, and water was added to the resulting powder to suspend it. The resulting suspension was suction filtered, the solid was dissolved in chloroform (about 50 mL) and transferred to a separating funnel, and the resulting solution was washed with water-saturated sodium bicarbonate solution-brine in this order. After the chloroform layer was dehydrated with magnesium sulfate, it was filtered through liquid phase separation filter paper, and the organic layer was concentrated with a rotary evaporator. Ethyl acetate and hexane were added to the resulting white solid to suspend it, and the suspension was suction-filtered, and the obtained crystals were dried under reduced pressure to obtain Compound 4 (1.97 g). The measured physical properties of the product are as follows.
1H NMR (400 MHz DMSO-d6): 7.91-7.81ppm (m, 4H), 7.04ppm (s, 1H), 6.70ppm (s, 1H), 5.37ppm (d, 5.6Hz, 1H), 4.05-3.93ppm (m, 2H), 3.82ppm (dd, 8.8Hz, 15.2Hz, 1H), 3.63ppm (dd, 7.8Hz, 14Hz, 1H), 3.53ppm (dd, 4.8Hz, 14Hz)
1 H NMR (400 MHz DMSO-d6): 7.91-7.81ppm (m, 4H), 7.04ppm (s, 1H), 6.70ppm (s, 1H), 5.37ppm (d, 5.6Hz, 1H), 4.05- 3.93ppm (m, 2H), 3.82ppm (dd, 8.8Hz, 15.2Hz, 1H), 3.63ppm (dd, 7.8Hz, 14Hz, 1H), 3.53ppm (dd, 4.8Hz, 14Hz)
(化合物5)2-[2-(2-methyl-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
化合物5(CAS登録番号:858512-76-2)は市販品(FCH Group社より購入)を用いた。 (Compound 5) 2-[2-(2-methyl-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
Compound 5 (CAS registration number: 858512-76-2) was a commercially available product (purchased from FCH Group).
化合物5(CAS登録番号:858512-76-2)は市販品(FCH Group社より購入)を用いた。 (Compound 5) 2-[2-(2-methyl-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
Compound 5 (CAS registration number: 858512-76-2) was a commercially available product (purchased from FCH Group).
(化合物6)2-[2-(1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
化合物6(CAS登録番号:72459-53-1)は市販品(Enamine社より購入)を用いた。 (Compound 6) 2-[2-(1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
Compound 6 (CAS registration number: 72459-53-1) was a commercially available product (purchased from Enamine).
化合物6(CAS登録番号:72459-53-1)は市販品(Enamine社より購入)を用いた。 (Compound 6) 2-[2-(1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione
Compound 6 (CAS registration number: 72459-53-1) was a commercially available product (purchased from Enamine).
(化合物7)1-(2-methyl-1H-imidazole-1-yl)-3-phenoxypropan-2-olの合成
(Compound 7) Synthesis of 1-(2-methyl-1H-imidazole-1-yl)-3-phenoxypropan-2-ol
2-Methyl-1H-imidazole(四国化成工業社製、21.8g、266mmol)をトルエン(78.7mL)とメタノール(17.7mL)の混合溶媒に溶解させ、80℃に昇温し、デナコールEX-141(ナガセケムテックス社製、22.0g、147mmol)のトルエン(38.1mL)溶液を1時間かけて滴下し、その後、同温度で1時間攪拌した。得られた溶液を室温まで冷却し、減圧下で溶媒を留去し、1-(2-methyl-1H-imidazole-1-yl)-3-phenoxypropan-2-ol(47.85g)を黄色固体として得た。生成物の同定は1HNMRより行い、目的物が得られていることを確認した。
2-Methyl-1H-imidazole (manufactured by Shikoku Kasei Co., Ltd., 21.8 g, 266 mmol) was dissolved in a mixed solvent of toluene (78.7 mL) and methanol (17.7 mL), heated to 80° C., and Denacol EX was prepared. A toluene (38.1 mL) solution of -141 (manufactured by Nagase ChemteX Corporation, 22.0 g, 147 mmol) was added dropwise over 1 hour, followed by stirring at the same temperature for 1 hour. The resulting solution was cooled to room temperature, the solvent was removed under reduced pressure, and 1-(2-methyl-1H-imidazole-1-yl)-3-phenoxypropan-2-ol (47.85 g) was obtained as a yellow solid. obtained as The product was identified by 1 HNMR, and it was confirmed that the desired product was obtained.
(化合物8)1-[([1,1’-biphenyl]-2-yl)oxy]-3-(2-methyl-1H-imidazole-1-yl)propan-2-olの合成
(Compound 8) Synthesis of 1-[([1,1'-biphenyl]-2-yl)oxy]-3-(2-methyl-1H-imidazole-1-yl)propan-2-ol
2-methyl-1-H-imidazole(四国化成工業社製、150g、1.83mol)を、室温でトルエン(443mL)とメタノール(121mL)の混合溶媒に溶解して得られた溶液を、80℃に加熱し、撹拌しながら還流した。得られた溶液に、2-{[([1,1’-biphenyl]-2-yl)oxy]methyl}oxirane(三光社製、210g、0.913mol、エポキシ当量230g/eq)を室温でトルエン(363mL)に溶解した溶液を滴下速度3.75mL/minで添加した。全量滴下した後、得られた混合物を80℃で75分間撹拌した。その後、得られた反応物をエバポレーターを用いて50℃で溶媒を留去し、化合物8(392g)を得た。生成物の同定は1HNMRより行い、目的物が得られていることを確認した。
2-methyl-1-H-imidazole (manufactured by Shikoku Kasei Co., Ltd., 150 g, 1.83 mol) was dissolved in a mixed solvent of toluene (443 mL) and methanol (121 mL) at room temperature. and heated to reflux with stirring. To the resulting solution, 2-{[([1,1′-biphenyl]-2-yl)oxy]methyl}oxirane (manufactured by Sanko Co., Ltd., 210 g, 0.913 mol, epoxy equivalent 230 g/eq) was added to toluene at room temperature. (363 mL) was added dropwise at a rate of 3.75 mL/min. After dropping the entire amount, the resulting mixture was stirred at 80° C. for 75 minutes. After that, the solvent was distilled off from the obtained reactant at 50° C. using an evaporator to obtain compound 8 (392 g). The product was identified by 1 HNMR, and it was confirmed that the desired product was obtained.
==化合物の評価==
<融点の測定>
示差走査熱量測定装置(DSC 204 F1 Phoenix(登録商標))(NETZSCH社製)を用いて融点を測定した。まず、アルミパンに合成した化合物5mgを計量し、アルミ製の蓋でシーリングした後、その蓋の中心に針で穴を開けて測定サンプルを準備した。次に、この測定サンプルを窒素雰囲気下(100mL/分)、25~250℃の範囲で、速度10℃/分の条件で昇温しながら熱流(mW/mg)を測定した。融点に相当し、グラフ上でピークが得られる温度を解析ソフト(NETZSCH Proteus-Thermal Analysis バージョン8.0.2)で算出した。化合物1-6、8では明確なピークが得られたが、化合物7では、明確なピークが得られなかった。
次に、融点における熱流(すなわち、最大熱流)と、ピークの面積(すなわち、融解熱)を装置の解析ソフトによって解析し、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値を計算した。
さらに、25~250℃の範囲で、昇温速度10℃/分と昇温速度50℃/分の条件で熱流(mW/mg)を測定し、各条件での融解開始温度(℃)を解析し、昇温速度依存度として、(昇温速度50℃/分の時の融解開始温度)/(昇温速度10℃/分の時の融解開始温度)を算出した。なお、融解開始温度とは、融点よりも低温側において、融解ピーク曲線の接線のうち最大勾配となる接線と、DSCのベースラインとの交点の温度である。 == Evaluation of compounds ==
<Measurement of melting point>
The melting point was measured using a differential scanning calorimeter (DSC 204 F1 Phoenix (registered trademark)) (manufactured by NETZSCH). First, 5 mg of the synthesized compound was weighed in an aluminum pan, sealed with an aluminum lid, and a hole was made in the center of the lid with a needle to prepare a measurement sample. Next, the heat flow (mW/mg) was measured while raising the temperature of this measurement sample in a nitrogen atmosphere (100 mL/min) in the range of 25 to 250° C. at a rate of 10° C./min. The temperature corresponding to the melting point and at which a peak is obtained on the graph was calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 8.0.2). Compounds 1-6 and 8 gave clear peaks, but Compound 7 did not give a clear peak.
Next, the heat flow at the melting point (i.e., maximum heat flow) and the area of the peak (i.e., heat of fusion) are analyzed by the analysis software of the apparatus, (maximum heat flow [mW / mg]) / (heat of fusion [J / g] ) was calculated.
Furthermore, in the range of 25 to 250°C, the heat flow (mW/mg) was measured under the conditions of a heating rate of 10°C/min and a heating rate of 50°C/min, and the melting initiation temperature (°C) under each condition was analyzed. Then, as the temperature increase rate dependence, (melting start temperature at a temperature increase rate of 50° C./min)/(melting start temperature at a temperature increase rate of 10° C./min) was calculated. The melting initiation temperature is the temperature at the intersection of the tangent line with the maximum gradient among the tangent lines of the melting peak curve and the DSC baseline on the lower temperature side than the melting point.
<融点の測定>
示差走査熱量測定装置(DSC 204 F1 Phoenix(登録商標))(NETZSCH社製)を用いて融点を測定した。まず、アルミパンに合成した化合物5mgを計量し、アルミ製の蓋でシーリングした後、その蓋の中心に針で穴を開けて測定サンプルを準備した。次に、この測定サンプルを窒素雰囲気下(100mL/分)、25~250℃の範囲で、速度10℃/分の条件で昇温しながら熱流(mW/mg)を測定した。融点に相当し、グラフ上でピークが得られる温度を解析ソフト(NETZSCH Proteus-Thermal Analysis バージョン8.0.2)で算出した。化合物1-6、8では明確なピークが得られたが、化合物7では、明確なピークが得られなかった。
次に、融点における熱流(すなわち、最大熱流)と、ピークの面積(すなわち、融解熱)を装置の解析ソフトによって解析し、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値を計算した。
さらに、25~250℃の範囲で、昇温速度10℃/分と昇温速度50℃/分の条件で熱流(mW/mg)を測定し、各条件での融解開始温度(℃)を解析し、昇温速度依存度として、(昇温速度50℃/分の時の融解開始温度)/(昇温速度10℃/分の時の融解開始温度)を算出した。なお、融解開始温度とは、融点よりも低温側において、融解ピーク曲線の接線のうち最大勾配となる接線と、DSCのベースラインとの交点の温度である。 == Evaluation of compounds ==
<Measurement of melting point>
The melting point was measured using a differential scanning calorimeter (DSC 204 F1 Phoenix (registered trademark)) (manufactured by NETZSCH). First, 5 mg of the synthesized compound was weighed in an aluminum pan, sealed with an aluminum lid, and a hole was made in the center of the lid with a needle to prepare a measurement sample. Next, the heat flow (mW/mg) was measured while raising the temperature of this measurement sample in a nitrogen atmosphere (100 mL/min) in the range of 25 to 250° C. at a rate of 10° C./min. The temperature corresponding to the melting point and at which a peak is obtained on the graph was calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 8.0.2). Compounds 1-6 and 8 gave clear peaks, but Compound 7 did not give a clear peak.
Next, the heat flow at the melting point (i.e., maximum heat flow) and the area of the peak (i.e., heat of fusion) are analyzed by the analysis software of the apparatus, (maximum heat flow [mW / mg]) / (heat of fusion [J / g] ) was calculated.
Furthermore, in the range of 25 to 250°C, the heat flow (mW/mg) was measured under the conditions of a heating rate of 10°C/min and a heating rate of 50°C/min, and the melting initiation temperature (°C) under each condition was analyzed. Then, as the temperature increase rate dependence, (melting start temperature at a temperature increase rate of 50° C./min)/(melting start temperature at a temperature increase rate of 10° C./min) was calculated. The melting initiation temperature is the temperature at the intersection of the tangent line with the maximum gradient among the tangent lines of the melting peak curve and the DSC baseline on the lower temperature side than the melting point.
==樹脂組成物の作製方法==
== Method for preparing resin composition ==
<実施例1~4、6、比較例1、2:エポキシ-チオール硬化系>
硬化触媒としての化合物1~4、6、7、8をエポキシ樹脂であるEXA835LV(DIC社製)に投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、EXA835LV、またはEXA835LVとCDMDG(昭和電工社製)の混合物を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらに、チオール樹脂であるPEMP(SC有機化学社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Examples 1 to 4, 6, Comparative Examples 1, 2: Epoxy-thiol curing system>
Compounds 1 to 4, 6, 7, and 8 as curing catalysts were put into EXA835LV (manufactured by DIC), which is an epoxy resin, and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. Then, EXA835LV or a mixture of EXA835LV and CDMDG (manufactured by Showa Denko KK) was added and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device. Furthermore, PEMP (manufactured by SC Organic Chemical Co., Ltd.), which is a thiol resin, was added and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
硬化触媒としての化合物1~4、6、7、8をエポキシ樹脂であるEXA835LV(DIC社製)に投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、EXA835LV、またはEXA835LVとCDMDG(昭和電工社製)の混合物を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらに、チオール樹脂であるPEMP(SC有機化学社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Examples 1 to 4, 6, Comparative Examples 1, 2: Epoxy-thiol curing system>
<実施例5:エポキシ-チオール硬化系>
EXA835LVとTS720(キャボット・スペシャルティー・ケミカルズ社製)を3本ロールミルで分散した混合物へ硬化触媒としての化合物1を投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、チオール樹脂であるC3TSG(四国化成工業社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 5: Epoxy-thiol curing system>
Compound 1 as a curing catalyst was added to a mixture obtained by dispersing EXA835LV and TS720 (manufactured by Cabot Specialty Chemicals) using a three-roll mill and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus. C3TSG (manufactured by Shikoku Kasei Kogyo Co., Ltd.), which is a thiol resin, was added thereto and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
EXA835LVとTS720(キャボット・スペシャルティー・ケミカルズ社製)を3本ロールミルで分散した混合物へ硬化触媒としての化合物1を投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、チオール樹脂であるC3TSG(四国化成工業社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 5: Epoxy-thiol curing system>
<実施例7、11、12:エポキシホモ重合硬化系>
硬化触媒としての化合物1、5、6、をEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式撹拌脱泡装置を用いて、真空下にて撹拌及び脱泡を行い、樹脂組成物を得た。 <Examples 7, 11, 12: Epoxy homopolymerization curing system>
Compounds 1, 5 and 6 as curing catalysts were put into EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus to obtain a resin composition.
硬化触媒としての化合物1、5、6、をEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式撹拌脱泡装置を用いて、真空下にて撹拌及び脱泡を行い、樹脂組成物を得た。 <Examples 7, 11, 12: Epoxy homopolymerization curing system>
<実施例8:エポキシ-酸無水物硬化系>
硬化触媒としての化合物1をエポキシ樹脂であるEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、YDF8170(新日鐵住金化学社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらにそこへ酸無水物樹脂であるYH306(三菱ケミカル社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 8: Epoxy-acid anhydride curing system>
Compound 1 as a curing catalyst was put into EXA835LV, which is an epoxy resin, and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming apparatus. Then, YDF8170 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) was added and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device. Furthermore, YH306 (manufactured by Mitsubishi Chemical Co., Ltd.), which is an acid anhydride resin, was added thereto and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
硬化触媒としての化合物1をエポキシ樹脂であるEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、YDF8170(新日鐵住金化学社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらにそこへ酸無水物樹脂であるYH306(三菱ケミカル社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 8: Epoxy-acid anhydride curing system>
<実施例9:エポキシ-フェノール硬化系>
硬化触媒としての化合物1をEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、EXA835LVを投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらにそこへフェノール樹脂であるMEH8005(明和化成社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 9: Epoxy-phenol curing system>
Compound 1 as a curing catalyst was added to EXA835LV and mixed. Thereafter, the mixture was ground in a mortar until no aggregation occurred, and stirred and defoamed under vacuum using a planetary stirring and defoaming device. EXA835LV was put in there and mixed. Thereafter, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device. Furthermore, MEH8005 (manufactured by Meiwa Kasei Co., Ltd.), which is a phenolic resin, was added and mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming were performed under vacuum to obtain a resin composition.
硬化触媒としての化合物1をEXA835LVに投入して混合した。その後、乳鉢で凝集が無くなるまですり潰し、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。そこへ、EXA835LVを投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行った。さらにそこへフェノール樹脂であるMEH8005(明和化成社製)を投入して混合した。その後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 9: Epoxy-phenol curing system>
<実施例10:アクリル-チオール硬化系>
アクリル樹脂であるM7100(東亞合成社製)、光ラジカル発生剤であるOMNIRAD184(IGM resins B.V.社製)、重合禁止剤としてQ-1301(富士フィルム和光純薬社製)、搖変剤としてTS720を3本ロールミルで分散させ、得られた混合物に、硬化触媒としての化合物1を投入し、さらに3本ロールミルで分散させた。そこへ、PEMPを投入して混合した後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 10: Acrylic-thiol curing system>
M7100 (manufactured by Toagosei Co., Ltd.) as an acrylic resin, OMNIRAD184 (manufactured by IGM resins B.V.) as a photoradical generator, Q-1301 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a polymerization inhibitor, and a stabilizing agent. TS720 was dispersed with a three-roll mill as a component, andcompound 1 as a curing catalyst was added to the resulting mixture and further dispersed with a three-roll mill. After PEMP was added thereto and mixed, stirring and defoaming were performed under vacuum using a planetary stirring and defoaming device to obtain a resin composition.
アクリル樹脂であるM7100(東亞合成社製)、光ラジカル発生剤であるOMNIRAD184(IGM resins B.V.社製)、重合禁止剤としてQ-1301(富士フィルム和光純薬社製)、搖変剤としてTS720を3本ロールミルで分散させ、得られた混合物に、硬化触媒としての化合物1を投入し、さらに3本ロールミルで分散させた。そこへ、PEMPを投入して混合した後、遊星式攪拌脱泡装置を用いて、真空下にて攪拌及び脱泡を行い、樹脂組成物を得た。 <Example 10: Acrylic-thiol curing system>
M7100 (manufactured by Toagosei Co., Ltd.) as an acrylic resin, OMNIRAD184 (manufactured by IGM resins B.V.) as a photoradical generator, Q-1301 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a polymerization inhibitor, and a stabilizing agent. TS720 was dispersed with a three-roll mill as a component, and
==樹脂組成物の評価方法==
<ポットライフの測定>
樹脂組成物の初期粘度を、E型粘度計(TVE‐25H:東機産業社製、ロータ名称:3°×R9.7)を用いて、50rpm、25℃で、予め設定された適切なレンジ(H、R、またはU)で測定した。次に、25℃、湿度50%の環境下にて、密閉容器に保存した樹脂組成物を放置し、4時間ごとに、その樹脂組成物の粘度を、E型粘度計(TVE‐25H:東機産業社製、ロータ名称:3°×R9.7)を用いて、50rpm、25℃で
、予め設定された適切なレンジ(H、R、またはU)で測定した。そして、(各時間における放置した後の粘度)/(初期粘度)を算出して各時間における放置後の増粘倍率とし、ポットライフとして8時間以内に硬化しなかったものを○、硬化したものを×とした。 == Evaluation method of resin composition ==
<Measurement of pot life>
The initial viscosity of the resin composition is measured using an E-type viscometer (TVE-25H: manufactured by Toki Sangyo Co., Ltd., rotor name: 3 ° × R9.7) at 50 rpm, 25 ° C., an appropriate range set in advance Measured in (H, R, or U). Next, leave the resin composition stored in a sealed container in an environment of 25 ° C. and 50% humidity, and measure the viscosity of the resin composition every 4 hours with an E-type viscometer (TVE-25H: East Using a rotor name: 3°×R9.7 manufactured by Kisangyo Co., Ltd., measurement was performed at 50 rpm and 25° C. in a preset appropriate range (H, R, or U). Then, (viscosity after standing at each time) / (initial viscosity) is calculated as the thickening ratio after standing at each time. was x.
<ポットライフの測定>
樹脂組成物の初期粘度を、E型粘度計(TVE‐25H:東機産業社製、ロータ名称:3°×R9.7)を用いて、50rpm、25℃で、予め設定された適切なレンジ(H、R、またはU)で測定した。次に、25℃、湿度50%の環境下にて、密閉容器に保存した樹脂組成物を放置し、4時間ごとに、その樹脂組成物の粘度を、E型粘度計(TVE‐25H:東機産業社製、ロータ名称:3°×R9.7)を用いて、50rpm、25℃で
、予め設定された適切なレンジ(H、R、またはU)で測定した。そして、(各時間における放置した後の粘度)/(初期粘度)を算出して各時間における放置後の増粘倍率とし、ポットライフとして8時間以内に硬化しなかったものを○、硬化したものを×とした。 == Evaluation method of resin composition ==
<Measurement of pot life>
The initial viscosity of the resin composition is measured using an E-type viscometer (TVE-25H: manufactured by Toki Sangyo Co., Ltd., rotor name: 3 ° × R9.7) at 50 rpm, 25 ° C., an appropriate range set in advance Measured in (H, R, or U). Next, leave the resin composition stored in a sealed container in an environment of 25 ° C. and 50% humidity, and measure the viscosity of the resin composition every 4 hours with an E-type viscometer (TVE-25H: East Using a rotor name: 3°×R9.7 manufactured by Kisangyo Co., Ltd., measurement was performed at 50 rpm and 25° C. in a preset appropriate range (H, R, or U). Then, (viscosity after standing at each time) / (initial viscosity) is calculated as the thickening ratio after standing at each time. was x.
<ゲルタイムの測定>
ゲル化する前の時間(ゲルタイムを称する)を、ゲル化試験機(GT-D-15A:ユーカリ技研社製)を用いて測定した。ホットプレートを100℃、120℃、または150℃に設定し、試験棒にて樹脂組成物をホットプレート上に転写した。試験棒で樹脂組成物に触れて、糸引きする状態になるまでの時間をゲルタイムとした。 <Measurement of gel time>
The time before gelation (referred to as gel time) was measured using a gelation tester (GT-D-15A: manufactured by Eucalyptus Giken Co., Ltd.). A hot plate was set to 100° C., 120° C., or 150° C., and the resin composition was transferred onto the hot plate using a test rod. The gel time was defined as the time from touching the resin composition with a test rod until it became stringy.
ゲル化する前の時間(ゲルタイムを称する)を、ゲル化試験機(GT-D-15A:ユーカリ技研社製)を用いて測定した。ホットプレートを100℃、120℃、または150℃に設定し、試験棒にて樹脂組成物をホットプレート上に転写した。試験棒で樹脂組成物に触れて、糸引きする状態になるまでの時間をゲルタイムとした。 <Measurement of gel time>
The time before gelation (referred to as gel time) was measured using a gelation tester (GT-D-15A: manufactured by Eucalyptus Giken Co., Ltd.). A hot plate was set to 100° C., 120° C., or 150° C., and the resin composition was transferred onto the hot plate using a test rod. The gel time was defined as the time from touching the resin composition with a test rod until it became stringy.
==結果==
以上の樹脂組成物の各構成成分の分量と評価結果を表2~3にまとめた。 == Results ==
Tables 2 and 3 summarize the amount of each constituent component of the above resin composition and the evaluation results.
以上の樹脂組成物の各構成成分の分量と評価結果を表2~3にまとめた。 == Results ==
Tables 2 and 3 summarize the amount of each constituent component of the above resin composition and the evaluation results.
表1~表3に示すように、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が大きく、昇温速度依存度の小さい化合物1~6を用いた樹脂組成物では、樹脂組成物作製後8時間経っても粘度はほとんど変わらなかった。一方、明確な融解ピークが得られず、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値の算出ができなかった化合物7では、エポキシ樹脂などに溶解しやすく、4時間以内に硬化した。(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が小さく、昇温速度依存度の大きい化合物8も、8時間以内に硬化した。このように、実施例の樹脂組成物のほうが、ポットライフが長かった。
As shown in Tables 1 to 3, the absolute value of (maximum heat flow [mW / mg]) / (heat of fusion [J / g]) is large, and resins using compounds 1 to 6 with small temperature rise rate dependence The viscosity of the composition hardly changed even after 8 hours from the preparation of the resin composition. On the other hand, compound 7, for which no clear melting peak could be obtained and the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) could not be calculated, was easily dissolved in epoxy resin and the like. , cured within 4 hours. Compound 8, which had a small absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) and had a large dependence on the heating rate, also cured within 8 hours. Thus, the resin compositions of Examples had a longer pot life.
実施例における樹脂組成物は、10分以内にゲル化し、十分な反応性および硬化性があった。
The resin composition in the example gelled within 10 minutes and had sufficient reactivity and curability.
また、表3に示すように、エポキシ-チオール硬化系だけでなく、エポキシホモ重合系、エポキシ-酸無水物系、エポキシ-フェノール系、アクリレート-チオール系においても、本開示の硬化触媒は利用可能である。特に、エポキシ-チオール硬化系の硬化触媒として好ましい。
In addition, as shown in Table 3, the curing catalyst of the present disclosure can be used not only in epoxy-thiol curing systems, but also in epoxy homopolymerization systems, epoxy-acid anhydride systems, epoxy-phenol systems, and acrylate-thiol systems. is. In particular, it is preferable as a curing catalyst for an epoxy-thiol curing system.
このように、本開示の硬化触媒は、フタルイミド骨格を有することにより、結晶性が高く、エポキシ樹脂とイミダゾール誘導体を付加させた従来のアダクト体よりも高融点であり、また本開示の硬化触媒によって、安定で、意図しない温度における硬化触媒の樹脂への溶解が起こりにくく、ポットライフの長い樹脂組成物が得られる。
Thus, the curing catalyst of the present disclosure has a phthalimide skeleton, so it has high crystallinity and a higher melting point than conventional adducts obtained by adding an epoxy resin and an imidazole derivative. , a resin composition which is stable, hardly causes the curing catalyst to dissolve in the resin at an unintended temperature, and has a long pot life can be obtained.
本発明によって、新規なアミン誘導体を提供することができるようになった。
The present invention has made it possible to provide novel amine derivatives.
Claims (10)
- 示差走査熱量測定(DSC)において、
(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.10以下である、フタルイミド骨格を有するアミン誘導体。 In differential scanning calorimetry (DSC),
An amine derivative having a phthalimide skeleton, wherein the value of (melting initiation temperature at a heating rate of 50° C./min)/(melting initiation temperature at a heating rate of 10° C./min) is 1.00 or more and 1.10 or less. - 前記(昇温速度50℃/minの融解開始温度)/(昇温速度10℃/minの融解開始温度)の値が1.00以上1.02以下である、請求項1に記載のアミン誘導体。 2. The amine derivative according to claim 1, wherein the value of (the melting initiation temperature at a heating rate of 50° C./min)/(the melting initiation temperature at a heating rate of 10° C./min) is 1.00 or more and 1.02 or less. .
- 昇温速度10℃/minの示差走査熱量測定(DSC)において、
融解における、(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が0.01以上0.10以下である、請求項1または2に記載のアミン誘導体。 In differential scanning calorimetry (DSC) with a heating rate of 10 ° C./min,
3. The amine derivative according to claim 1, wherein the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) in melting is 0.01 or more and 0.10 or less. - 前記(最大熱流[mW/mg])/(融解熱[J/g])の絶対値が0.023以上0.045以下である、請求項3に記載のアミン誘導体。 The amine derivative according to claim 3, wherein the absolute value of (maximum heat flow [mW/mg])/(heat of fusion [J/g]) is 0.023 or more and 0.045 or less.
- 請求項1~4のいずれか1項に記載のアミン誘導体を含有する、エポキシ樹脂の硬化触媒。 An epoxy resin curing catalyst containing the amine derivative according to any one of claims 1 to 4.
- 請求項5に記載の硬化触媒を含有する樹脂組成物。 A resin composition containing the curing catalyst according to claim 5.
- 請求項6に記載の樹脂組成物を含有する、封止材。 A sealing material containing the resin composition according to claim 6.
- 請求項6に記載の樹脂組成物を含有する、接着剤。 An adhesive containing the resin composition according to claim 6.
- 請求項6に記載の樹脂組成物の硬化物。 A cured product of the resin composition according to claim 6.
- フタルイミド骨格を有し、かつ1つのエポキシ基を有する化合物を、アミンにアダクトする工程を含む、請求項1~4のいずれか1項に記載のアミン誘導体の製造方法。 The method for producing an amine derivative according to any one of claims 1 to 4, comprising a step of adducting a compound having a phthalimide skeleton and one epoxy group to an amine.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3379685A (en) * | 1964-08-31 | 1968-04-23 | Ciba Ltd | Curable epoxy compound composition of matter |
US4619941A (en) * | 1984-11-19 | 1986-10-28 | American Cyanamid Company | N-[(1H-imidazol-1-yl)alkyl]-1H-indolecarboxamides useful as thromboxane synthetase inhibitors and antihypertensive agents |
WO1988008840A1 (en) * | 1987-05-04 | 1988-11-17 | Centre National De La Recherche Scientifique (Cnrs | Anti-tumoral targetting agents, preparation thereof and applications |
JPH10218859A (en) * | 1997-02-04 | 1998-08-18 | Shikoku Chem Corp | Trimellitimide derivative and its production |
WO2014104272A1 (en) * | 2012-12-28 | 2014-07-03 | 日本臓器製薬株式会社 | Cinnamic acid amide derivative |
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- 2022-03-23 WO PCT/JP2022/013647 patent/WO2022210190A1/en active Application Filing
- 2022-03-29 TW TW111111929A patent/TW202300488A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3379685A (en) * | 1964-08-31 | 1968-04-23 | Ciba Ltd | Curable epoxy compound composition of matter |
US4619941A (en) * | 1984-11-19 | 1986-10-28 | American Cyanamid Company | N-[(1H-imidazol-1-yl)alkyl]-1H-indolecarboxamides useful as thromboxane synthetase inhibitors and antihypertensive agents |
WO1988008840A1 (en) * | 1987-05-04 | 1988-11-17 | Centre National De La Recherche Scientifique (Cnrs | Anti-tumoral targetting agents, preparation thereof and applications |
JPH10218859A (en) * | 1997-02-04 | 1998-08-18 | Shikoku Chem Corp | Trimellitimide derivative and its production |
WO2014104272A1 (en) * | 2012-12-28 | 2014-07-03 | 日本臓器製薬株式会社 | Cinnamic acid amide derivative |
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