WO2022210189A1 - Curing catalyst, resin composition, sealing material, adhesive, and cured product - Google Patents
Curing catalyst, resin composition, sealing material, adhesive, and cured product Download PDFInfo
- Publication number
- WO2022210189A1 WO2022210189A1 PCT/JP2022/013646 JP2022013646W WO2022210189A1 WO 2022210189 A1 WO2022210189 A1 WO 2022210189A1 JP 2022013646 W JP2022013646 W JP 2022013646W WO 2022210189 A1 WO2022210189 A1 WO 2022210189A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- manufactured
- resin composition
- compound
- mercaptomethylthio
- resin
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 13
- 239000003566 sealing material Substances 0.000 title claims abstract description 8
- 239000012945 sealing adhesive Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000003822 epoxy resin Substances 0.000 claims description 55
- 229920000647 polyepoxide Polymers 0.000 claims description 55
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- -1 thiol compounds Chemical class 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229920001187 thermosetting polymer Polymers 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 31
- 238000003756 stirring Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 17
- 239000013500 performance material Substances 0.000 description 17
- 239000000945 filler Substances 0.000 description 15
- 239000006087 Silane Coupling Agent Substances 0.000 description 13
- 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
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000004570 mortar (masonry) 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000126 substance Substances 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
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 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
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 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
- 239000010959 steel Substances 0.000 description 3
- 239000000725 suspension Substances 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
- DNVXWIINBUTFEP-UHFFFAOYSA-N 2-[(2-phenylphenoxy)methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1=CC=CC=C1 DNVXWIINBUTFEP-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
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-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
- 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
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 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
- 239000012948 isocyanate Substances 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
- 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
- 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
- 125000005543 phthalimide group Chemical group 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
- 239000002904 solvent Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 238000012360 testing 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
- 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
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- MBNMVPPPCZKPIJ-UHFFFAOYSA-N 1-[3-[3-[3-(2,5-dioxopyrrol-1-yl)phenoxy]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(OC=2C=C(OC=3C=C(C=CC=3)N3C(C=CC3=O)=O)C=CC=2)=C1 MBNMVPPPCZKPIJ-UHFFFAOYSA-N 0.000 description 1
- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
- GUIACFHOZIQGKX-UHFFFAOYSA-N 1-[4-[4-(2,5-dioxopyrrol-1-yl)phenyl]sulfonylphenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(S(=O)(=O)C=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=C1 GUIACFHOZIQGKX-UHFFFAOYSA-N 0.000 description 1
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- XHAFIUUYXQFJEW-UHFFFAOYSA-N 1-chloroethenylbenzene Chemical compound ClC(=C)C1=CC=CC=C1 XHAFIUUYXQFJEW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- JTINZFQXZLCHNS-UHFFFAOYSA-N 2,2-bis(oxiran-2-ylmethoxymethyl)butan-1-ol Chemical compound C1OC1COCC(CO)(CC)COCC1CO1 JTINZFQXZLCHNS-UHFFFAOYSA-N 0.000 description 1
- VAAWBNFNCBSMQF-UHFFFAOYSA-N 2,2-bis(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSCC(SCS)SCS VAAWBNFNCBSMQF-UHFFFAOYSA-N 0.000 description 1
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- WXDDGAZCUPULGL-UHFFFAOYSA-N 2,3-bis(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCC(SCS)CSCS WXDDGAZCUPULGL-UHFFFAOYSA-N 0.000 description 1
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- ABUWJLFYAOBREB-UHFFFAOYSA-N 2-(2-hydroxy-3-imidazol-1-ylpropyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(O)CN1C=CN=C1 ABUWJLFYAOBREB-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GQTBMBMBWQJACJ-UHFFFAOYSA-N 2-[(4-butan-2-ylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)CC)=CC=C1OCC1OC1 GQTBMBMBWQJACJ-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- GXANCFOKAWEPIS-UHFFFAOYSA-N 2-[(4-phenylphenoxy)methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1C1=CC=CC=C1 GXANCFOKAWEPIS-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- QTEWPHJCEXIMRJ-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCC(SCCS)CSCCS QTEWPHJCEXIMRJ-UHFFFAOYSA-N 0.000 description 1
- NKMOLEYVYVWWJC-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis[2-(3-sulfanylbutanoyloxy)ethyl]-1,3,5-triazinan-1-yl]ethyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCN1C(=O)N(CCOC(=O)CC(C)S)C(=O)N(CCOC(=O)CC(C)S)C1=O NKMOLEYVYVWWJC-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- KIVDBXVDNQFFFL-UHFFFAOYSA-N 2-[3-(2-sulfanylethylsulfanyl)-2,2-bis(2-sulfanylethylsulfanylmethyl)propyl]sulfanylethanethiol Chemical compound SCCSCC(CSCCS)(CSCCS)CSCCS KIVDBXVDNQFFFL-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- TWYISXLZCIVDDW-UHFFFAOYSA-N 2-methyl-n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C(C)=C TWYISXLZCIVDDW-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- VWJQYGOMEPVJRD-UHFFFAOYSA-N 3,3-bis(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCCC(SCS)SCS VWJQYGOMEPVJRD-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- DUYICINCNBSZMH-UHFFFAOYSA-N 3-[2,3-bis(3-sulfanylpropylsulfanyl)propylsulfanyl]propane-1-thiol Chemical compound SCCCSCC(SCCCS)CSCCCS DUYICINCNBSZMH-UHFFFAOYSA-N 0.000 description 1
- MOSSLXZUUKTULI-UHFFFAOYSA-N 3-[3-(2,5-dioxopyrrol-3-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(C=2C(NC(=O)C=2)=O)C=C1C1=CC(=O)NC1=O MOSSLXZUUKTULI-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- OJVQNVMHJWSOSY-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(O)=O)(C)C2C(O)=O OJVQNVMHJWSOSY-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical compound CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- UVYLEXYRTBDZNM-UHFFFAOYSA-N 4,4-diethyloxane-2,6-dione Chemical compound CCC1(CC)CC(=O)OC(=O)C1 UVYLEXYRTBDZNM-UHFFFAOYSA-N 0.000 description 1
- WGCKYCGUJYPRCV-UHFFFAOYSA-N 4,5-dimethyl-7-(2-methylprop-1-enyl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound CC(C)=CC1C=C(C)C(C)C2C(=O)OC(=O)C12 WGCKYCGUJYPRCV-UHFFFAOYSA-N 0.000 description 1
- CBEVWPCAHIAUOD-UHFFFAOYSA-N 4-[(4-amino-3-ethylphenyl)methyl]-2-ethylaniline Chemical compound C1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=CC=2)=C1 CBEVWPCAHIAUOD-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- CXXSQMDHHYTRKY-UHFFFAOYSA-N 4-amino-2,3,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1=C(O)C(CC2OC2)=C(CC2OC2)C(N)=C1CC1CO1 CXXSQMDHHYTRKY-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 1
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- JBBURRWEMSTGIX-UHFFFAOYSA-N 5-ethyl-5-methyl-1,3-bis(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound O=C1N(CC2OC2)C(=O)C(CC)(C)N1CC1CO1 JBBURRWEMSTGIX-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- LQOPXMZSGSTGMF-UHFFFAOYSA-N 6004-79-1 Chemical compound C1CC2C3C(=O)OC(=O)C3C1C2 LQOPXMZSGSTGMF-UHFFFAOYSA-N 0.000 description 1
- GAYWTJPBIQKDRC-UHFFFAOYSA-N 8-trimethoxysilyloctyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C(C)=C GAYWTJPBIQKDRC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- QYJABHZWCKRMIC-UHFFFAOYSA-N C1(=CC(=CC=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(=CC(=CC=C1)C=1C(=O)NC(C1)=O)C=1C(=O)NC(C1)=O Chemical compound C1(=CC(=CC=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(=CC(=CC=C1)C=1C(=O)NC(C1)=O)C=1C(=O)NC(C1)=O QYJABHZWCKRMIC-UHFFFAOYSA-N 0.000 description 1
- PQRWMWCSAKDSQW-UHFFFAOYSA-N CC1=NC=CN1CC(CN(C(C1=CC=CC=C11)=O)C1=O)O Chemical compound CC1=NC=CN1CC(CN(C(C1=CC=CC=C11)=O)C1=O)O PQRWMWCSAKDSQW-UHFFFAOYSA-N 0.000 description 1
- CXBMFEIFLOIBST-UHFFFAOYSA-N CCCCCCCCCCCC1=NC=CN1CC(CN(C(C1=CC=CC=C11)=O)C1=O)O Chemical compound CCCCCCCCCCCC1=NC=CN1CC(CN(C(C1=CC=CC=C11)=O)C1=O)O CXBMFEIFLOIBST-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- PUZHXYSDMURDFB-UHFFFAOYSA-N O(CCOCCOCCOC)C(CCCOCCOCCOBOCCOCCOCCOCCOC)OCCOCCOCCOC Chemical compound O(CCOCCOCCOC)C(CCCOCCOCCOBOCCOCCOCCOCCOC)OCCOCCOCCOC PUZHXYSDMURDFB-UHFFFAOYSA-N 0.000 description 1
- IBNOPHZBBDGZSJ-UHFFFAOYSA-N OC(CN1C(C2=CC=CC=C2)=NC=C1)CN(C(C1=CC=CC=C11)=O)C1=O Chemical compound OC(CN1C(C2=CC=CC=C2)=NC=C1)CN(C(C1=CC=CC=C11)=O)C1=O IBNOPHZBBDGZSJ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VSULQUDJBKAGDB-UHFFFAOYSA-N SCCC.SCCC.SCCC.SCCC.OCC(CO)(CO)CO Chemical compound SCCC.SCCC.SCCC.SCCC.OCC(CO)(CO)CO VSULQUDJBKAGDB-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- MALTWXYAYKZMJG-UHFFFAOYSA-N [1,2-bis(sulfanylmethylsulfanyl)-2-[1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethylsulfanyl]ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSC(SCS)C(SCS)SCS MALTWXYAYKZMJG-UHFFFAOYSA-N 0.000 description 1
- MKKUIBKEXGEELZ-UHFFFAOYSA-N [1,2-bis(sulfanylmethylsulfanyl)-2-[[5-[1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethylsulfanyl]-1,3-dithiolan-4-yl]sulfanylmethylsulfanyl]ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSC1SCSC1SCSC(SCS)C(SCS)SCS MKKUIBKEXGEELZ-UHFFFAOYSA-N 0.000 description 1
- JHVOWAGMIYZWGB-UHFFFAOYSA-N [1,3-bis(sulfanylmethylsulfanyl)-3-[1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanyl]propyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCSC(SCS)CC(SCS)SCS JHVOWAGMIYZWGB-UHFFFAOYSA-N 0.000 description 1
- RFAWDNBGSZZKPZ-UHFFFAOYSA-N [1,3-bis(sulfanylmethylsulfanyl)-3-[[6-[1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanyl]-1,3-dithian-4-yl]sulfanylmethylsulfanyl]propyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCSC1CC(SCSC(CC(SCS)SCS)SCS)SCS1 RFAWDNBGSZZKPZ-UHFFFAOYSA-N 0.000 description 1
- AFSQFGXTYWXFPP-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CO)CCCCC1 AFSQFGXTYWXFPP-UHFFFAOYSA-N 0.000 description 1
- KKVKUNIBLLLFHA-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CO)CCCCC1 KKVKUNIBLLLFHA-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- UCGZGVHUYXEZKZ-UHFFFAOYSA-N [2-[(1,3-dithietan-2-ylmethylsulfanylmethyldisulfanyl)methylsulfanyl]-1,2-bis(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSSCSCC1SCS1 UCGZGVHUYXEZKZ-UHFFFAOYSA-N 0.000 description 1
- DFQUSDPPYKEIFG-UHFFFAOYSA-N [2-[1-(1,3-dithietan-2-ylmethylsulfanylmethylsulfanylmethylsulfanyl)-2,2-bis(sulfanylmethylsulfanyl)ethyl]sulfanyl-1,2-bis(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SC(C(SCS)SCS)SCSCSCC1SCS1 DFQUSDPPYKEIFG-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- SBQJBBYMJCUVCI-UHFFFAOYSA-N [2-[2,2-bis(sulfanylmethylsulfanyl)ethyldisulfanyl]-1-(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CSSCC(SCS)SCS SBQJBBYMJCUVCI-UHFFFAOYSA-N 0.000 description 1
- JFTQMSXUSTXWAJ-UHFFFAOYSA-N [2-[2,2-bis(sulfanylmethylsulfanyl)ethylsulfanyl]-1-(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CSCC(SCS)SCS JFTQMSXUSTXWAJ-UHFFFAOYSA-N 0.000 description 1
- IJIYJUDUFMVYLK-UHFFFAOYSA-N [2-[3-[2,2-bis(sulfanylmethylsulfanyl)ethylsulfanyl]-2-[2,2-bis(sulfanylmethylsulfanyl)ethylsulfanylmethyl]propyl]sulfanyl-1-(sulfanylmethylsulfanyl)ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CSCC(CSCC(SCS)SCS)CSCC(SCS)SCS IJIYJUDUFMVYLK-UHFFFAOYSA-N 0.000 description 1
- XAAGVUQLDIOQGP-UHFFFAOYSA-N [3,3-bis[2,2-bis(sulfanylmethylsulfanyl)ethyl]-1,5,5-tris(sulfanylmethylsulfanyl)pentyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CC(CC(SCS)SCS)(CC(SCS)SCS)CC(SCS)SCS XAAGVUQLDIOQGP-UHFFFAOYSA-N 0.000 description 1
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 1
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- VLDJWLWRDVWISM-UHFFFAOYSA-N [3-(sulfanylmethylsulfanyl)-2,2-bis(sulfanylmethylsulfanylmethyl)propyl]sulfanylmethanethiol Chemical compound SCSCC(CSCS)(CSCS)CSCS VLDJWLWRDVWISM-UHFFFAOYSA-N 0.000 description 1
- FHKCCRRDKWJYCG-UHFFFAOYSA-N [3-[2,2-bis(sulfanylmethylsulfanyl)ethyl]-1,5,5-tris(sulfanylmethylsulfanyl)pentyl]sulfanylmethanethiol Chemical compound SCSC(SCS)CC(CC(SCS)SCS)CC(SCS)SCS FHKCCRRDKWJYCG-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- KYAJYRDCBUNEFT-UHFFFAOYSA-N [5-[1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethylsulfanyl]-1,3-dithiolan-4-yl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSC1SCSC1SCS KYAJYRDCBUNEFT-UHFFFAOYSA-N 0.000 description 1
- DJTLWOYBXWJGGN-UHFFFAOYSA-N [5-[[1,2-bis(sulfanylmethylsulfanyl)-2-[1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethylsulfanyl]ethyl]sulfanylmethyl]-1,3-dithiolan-4-yl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSC(SCS)C(SCS)SCC1SCSC1SCS DJTLWOYBXWJGGN-UHFFFAOYSA-N 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- MFIBZDZRPYQXOM-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 MFIBZDZRPYQXOM-UHFFFAOYSA-N 0.000 description 1
- ZGACYOKNEKDSNK-UHFFFAOYSA-N ac1mjht3 Chemical compound C1CC2(C)C3C(=O)OC(=O)C3C1(C(C)C)C=C2 ZGACYOKNEKDSNK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- IHUNBGSDBOWDMA-AQFIFDHZSA-N all-trans-acitretin Chemical compound COC1=CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1C IHUNBGSDBOWDMA-AQFIFDHZSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- NQFUSWIGRKFAHK-BDNRQGISSA-N alpha-Pinene epoxide Natural products C([C@@H]1O[C@@]11C)[C@@H]2C(C)(C)[C@H]1C2 NQFUSWIGRKFAHK-BDNRQGISSA-N 0.000 description 1
- 229930006723 alpha-pinene oxide Natural products 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- HECGKCOICWUUJU-UHFFFAOYSA-N bis(diphenylphosphanylmethyl)-phenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 HECGKCOICWUUJU-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- OZEHOHQZIRILDX-UHFFFAOYSA-N ctk1b7797 Chemical compound O=C1OC(=O)C2C1C1(C)CC2CC1 OZEHOHQZIRILDX-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 229940124568 digestive agent Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical class O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MDNFYIAABKQDML-UHFFFAOYSA-N heptyl 2-methylprop-2-enoate Chemical compound CCCCCCCOC(=O)C(C)=C MDNFYIAABKQDML-UHFFFAOYSA-N 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- KEZAKPHSMMMPQD-UHFFFAOYSA-N methylsulfanyl-(2-methylsulfanylphenyl)methanediamine Chemical compound CSC1=CC=CC=C1C(N)(N)SC KEZAKPHSMMMPQD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- HZGIOLNCNORPKR-UHFFFAOYSA-N n,n'-bis(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCC[Si](OC)(OC)OC HZGIOLNCNORPKR-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- ADGJZVKOKVENDN-UHFFFAOYSA-N n-(butoxymethyl)-2-methylprop-2-enamide Chemical compound CCCCOCNC(=O)C(C)=C ADGJZVKOKVENDN-UHFFFAOYSA-N 0.000 description 1
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 1
- YGRMNBNGHHDGCX-UHFFFAOYSA-N n-(ethoxymethyl)-2-methylprop-2-enamide Chemical compound CCOCNC(=O)C(C)=C YGRMNBNGHHDGCX-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- YOZHLACIXDCHPV-UHFFFAOYSA-N n-(methoxymethyl)-2-methylprop-2-enamide Chemical compound COCNC(=O)C(C)=C YOZHLACIXDCHPV-UHFFFAOYSA-N 0.000 description 1
- RMTGISUVUCWJIT-UHFFFAOYSA-N n-[3-[3-aminopropoxy(dimethoxy)silyl]propyl]-1-phenylprop-2-en-1-amine;hydrochloride Chemical compound Cl.NCCCO[Si](OC)(OC)CCCNC(C=C)C1=CC=CC=C1 RMTGISUVUCWJIT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery 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
- 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- 238000002076 thermal analysis method Methods 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F34/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain and having one or more carbon-to-carbon double bonds in a heterocyclic ring
-
- 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
-
- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G59/66—Mercaptans
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
- C08G2170/00—Compositions for adhesives
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the present invention relates to curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
- 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.
- the purpose of the present invention is to provide novel curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
- One embodiment of the present invention is a curing catalyst comprising a compound of structural formula (I) below.
- R 1 is a group selected from hydrogen, phenyl and C1-C17 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 or 1 or more and 3 or less.
- thermosetting resin may be an epoxy resin.
- the thermosetting resin may be a compound having a polymerizable double bond.
- a curing agent for the thermosetting resin may be further included.
- the curing agent may be one selected from the group consisting of oxygen-containing compounds, nitrogen-containing compounds, and thiol compounds.
- a further embodiment of the present invention is a sealing material, adhesive, or cured product containing any of the above resin compositions.
- a further embodiment of the present invention is a compound of structural formula (I) below.
- R 1 is a group selected from phenyl and C1-C17 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 OH and OAc
- n and m are integers, the sum of which is 1 or more and 12 or less.
- R 1 is a group selected from phenyl and C1-C10 alkyl
- R 2 , R 3 , R 5 are hydrogen, R4 is OH
- n and m may be one.
- the present invention has made it possible to provide novel curing catalysts, resin compositions, sealing materials, adhesives, and cured products.
- R 1 is a group selected from phenyl and C1-C17 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 OH and OAc
- n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less.
- R 1 is preferably selected from phenyl and C1-C11 alkyl.
- R 2 , R 3 and R 5 are preferably hydrogen.
- R4 is preferably OH.
- n and m are each 1.
- 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
- n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less.
- More preferably, the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
- this curing catalyst has a phthalimide skeleton, it is difficult for the curing catalyst to dissolve in the resin in an unintended temperature range in the resin composition, the pot life becomes longer, and it is useful as a curing catalyst for thermosetting resins. is.
- 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.
- epoxy resins and compounds having a polymerizable double bond group for example, (meth)acrylic compounds and maleimide compounds
- (meth)acrylic compounds and maleimide compounds can be exemplified.
- acryl and methacryl are collectively referred to as (meth)acryl.
- 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 composition of the present disclosure 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 16 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.,
- 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 Co., Ltd.; A-189 manufactured by Japan Co., Ltd.; Z-6062 manufactured by Dow Corning Toray; Sila Ace S810 manufactured by Himi Shoji Co., Ltd.; A-1891 manufactured by Dow Corning Toray Co., Ltd.; Z-6911 manufactured by Toray Dow Corning Co., Ltd.; Shin-Etsu Chemical Co., Ltd.; includes KBE-585), 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane (commercially available from Momentive Performance Materials Japan; A-1160).
- examples of the silane coupling agent having a sulfide group include bis(triethoxysilylpropyl) tetrasulfide
- examples of the silane coupling agent having a thioester group include 3-octanoylthio-1-propyltriethoxysilane (Commercially available products include A-LINK599 manufactured by Momentive Performance Materials Japan), and have an isocyanate group.
- 3-isocyanatopropyltriethoxysilane (commercially available products include KBE-9007 manufactured by Shin-Etsu Chemical Co., Ltd., A-1310 manufactured by Momentive Performance Materials Japan, etc.), 3 -Isocyanatopropyltrimethoxysilane (commercially available products include Y-5187 manufactured by Momentive Performance Materials Japan, GENIOSIL GF40 manufactured by Asahi Kasei Wacker Silicone Co., Ltd.) and the like.
- 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.
- Table 1 shows the evaluation results of the compounds.
- 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 device. 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
- Examples 7, 11, 12 Epoxy homopolymerization curing system> Compound 1, compound 5, and compound 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.
- Comparative Example 2 has a high melting point, it has a low molecular weight, so it is easily dissolved in epoxy resins and the like, and lacks stability.
- a comparison of the pot life of the resin composition revealed that the comparative examples were already cured in 4 hours, whereas the viscosity increase rate doubled in all the examples in 8 hours or longer.
- the resin composition in the example gelled within 10 minutes and had sufficient reactivity and curability.
- the curing catalyst of the present disclosure has a phthalimide skeleton, so it has high crystallinity and a higher melting point than the conventional adducts obtained by adding an epoxy resin and an imidazole derivative. , a stable resin composition is obtained in which the curing catalyst is less likely to dissolve in the resin at unintended temperatures.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
R1は、水素、フェニルおよびC1~C17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から選択される基であり(Ac:アセチル基の略号)、 nとmは整数であり、その和が1以上12以下または1以上3以下である。) One embodiment of the present invention is a curing catalyst comprising a compound of structural formula (I) below.
R 1 is a group selected from hydrogen, phenyl and C1-C17 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 or 1 or more and 3 or less. )
R1は、フェニルおよびC1~C17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、OHおよびOAc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12以下である。)
上記式中、
R1は、フェニルおよびC1~C10のアルキルから選択される基であり、
R2、R3、R5は、水素であり、
R4は、OHであり、
nとmは1であってもよい。 A further embodiment of the present invention is a compound of structural formula (I) below.
R 1 is a group selected from phenyl and C1-C17 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 OH and OAc;
n and m are integers, the sum of which is 1 or more and 12 or less. )
In the above formula,
R 1 is a group selected from phenyl and C1-C10 alkyl;
R 2 , R 3 , R 5 are hydrogen,
R4 is OH;
n and m may be one.
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2021-058849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. 2021-058849 filed on March 30, 2021, and is incorporated herein by reference to the basic application. .
本実施形態にかかる化合物は、
下記構造式(I)の化合物である。
R1は、フェニルおよびC1~C17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、OHおよびOAc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。)
R1は、フェニルおよびC1~C11のアルキルから選択されることが好ましい。R2、R3、R5は水素であることが好ましい。R4は、OHであることが好ましい。nとmは、それぞれ1であることが好ましい。 == compound ==
The compound according to this embodiment is
It is a compound of the following structural formula (I).
R 1 is a group selected from phenyl and C1-C17 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 OH and OAc;
n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less. )
R 1 is preferably selected from phenyl and C1-C11 alkyl. R 2 , R 3 and R 5 are preferably hydrogen. R4 is preferably OH. Preferably, n and m are each 1.
本実施形態にかかる硬化触媒は、下記の構造式(I)を有する化合物を含有する。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。)
より好ましくは、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 ==
The curing catalyst according to this embodiment contains 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;
n and m are integers, the sum of which is 1 or more and 12 or less, preferably 6 or less, more preferably 3 or less. )
More preferably, the sum of n and m is 1 when R4 is hydrogen, and both n and m are 1 when R4 is OH.
本明細書に開示の樹脂組成物は、構造式(I)を有する硬化触媒と、樹脂とを含有する。この樹脂組成物は、従来の硬化触媒を含有する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 ==
The resin composition disclosed herein contains a curing catalyst having structural formula (I) and a resin. This resin composition is more stable than resin compositions containing conventional curing catalysts, and has a longer pot life.
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.
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
本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 composition of the present disclosure 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.
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%.
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、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、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、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
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(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8は市販品(四国化成工業社より購入)を用いた。 (Compound 8) 2MZ-H
A commercially available product (purchased from Shikoku Kasei Co., Ltd.) was used as
<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。 == Method for evaluating 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).
硬化触媒としての化合物1~4、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>
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>
硬化触媒としての化合物1、化合物5、および化合物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>
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>
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>
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
<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4時間放置し、ポットライフとして4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。その後、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, the resin composition stored in a sealed container was left for 4 hours in an environment of 25 ° C. and 50% humidity. did. After that, every 4 hours, the viscosity of the resin composition was measured using an E-type viscometer (TVE-25H: manufactured by Toki Sangyo Co., Ltd., rotor name: 3 ° × R9.7) at 50 rpm and 25 ° C. Measurements were taken in the appropriate preset range (H, R, or U). Then, (viscosity after standing for each time)/(initial viscosity) was calculated as the thickening ratio after standing for each time.
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.
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.
樹脂組成物のポットライフの比較より、比較例では4時間ですでに硬化していたのに対し、実施例では、増粘率が2倍になるのがすべて8時間以上であった。 The melting point of the curing catalyst used in Examples was higher than that of Comparative Example 1. Although Comparative Example 2 has a high melting point, it has a low molecular weight, so it is easily dissolved in epoxy resins and the like, and lacks stability.
A comparison of the pot life of the resin composition revealed that the comparative examples were already cured in 4 hours, whereas the viscosity increase rate doubled in all the examples in 8 hours or longer.
Claims (12)
- 下記構造式(I)の化合物を有する、硬化触媒。
R1は、水素、フェニルおよびC1~C17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12以下である。) A curing catalyst having a compound of the following structural formula (I).
R 1 is a group selected from hydrogen, phenyl and C1-C17 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;
n and m are integers, the sum of which is 1 or more and 12 or less. ) - nとmの和が3以下である、請求項1に記載の硬化触媒。 The curing catalyst according to claim 1, wherein the sum of n and m is 3 or less.
- 請求項1または2に記載の硬化触媒と熱硬化性樹脂とを含有する樹脂組成物。 A resin composition containing the curing catalyst according to claim 1 or 2 and a thermosetting resin.
- 前記熱硬化性樹脂がエポキシ樹脂である、請求項3記載の樹脂組成物。 The resin composition according to claim 3, wherein the thermosetting resin is an epoxy resin.
- 前記熱硬化性樹脂が重合性二重結合を有する化合物である、請求項4に記載の樹脂組成物。 The resin composition according to claim 4, wherein the thermosetting resin is a compound having a polymerizable double bond.
- 前記熱硬化性樹脂の硬化剤をさらに含む、請求項4または5に記載の樹脂組成物。 The resin composition according to claim 4 or 5, further comprising a curing agent for said thermosetting resin.
- 前記硬化剤が、酸素含有化合物、窒素含有化合物、およびチオール化合物からなる群から選択される1つである請求項4~6のいずれか1項に記載の樹脂組成物。 The resin composition according to any one of claims 4 to 6, wherein the curing agent is one selected from the group consisting of oxygen-containing compounds, nitrogen-containing compounds and thiol compounds.
- 請求項3~7のいずれか1項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 any one of claims 3 to 7.
- 請求項3~7のいずれか1項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 any one of claims 3 to 7.
- 請求項3~7のいずれか1項に記載の樹脂組成物の硬化物。 A cured product of the resin composition according to any one of claims 3 to 7.
- 下記構造式(I)の化合物。
R1は、フェニルおよびC1~C17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、OHおよびOAc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12以下である。) A compound of the following structural formula (I).
R 1 is a group selected from phenyl and C1-C17 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 OH and OAc;
n and m are integers, the sum of which is 1 or more and 12 or less. ) - 請求項11に記載の化合物であって、式中、
R1は、フェニルおよびC1~C10のアルキルから選択される基であり、
R2、R3、R5は、水素であり、
R4は、OHであり、
nとmは1である化合物。 12. A compound of claim 11, wherein
R 1 is a group selected from phenyl and C1-C10 alkyl;
R 2 , R 3 , R 5 are hydrogen,
R4 is OH;
a compound in which n and m are 1;
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202280009235.XA CN116745281A (en) | 2021-03-30 | 2022-03-23 | Curing catalyst, resin composition, sealing material, adhesive, and cured product |
KR1020237020573A KR20230161929A (en) | 2021-03-30 | 2022-03-23 | Curing catalyst, resin composition, encapsulant, adhesive and cured material |
JP2023511074A JPWO2022210189A1 (en) | 2021-03-30 | 2022-03-23 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021-058849 | 2021-03-30 | ||
JP2021058849 | 2021-03-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022210189A1 true WO2022210189A1 (en) | 2022-10-06 |
Family
ID=83456663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/013646 WO2022210189A1 (en) | 2021-03-30 | 2022-03-23 | Curing catalyst, resin composition, sealing material, adhesive, and cured product |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPWO2022210189A1 (en) |
KR (1) | KR20230161929A (en) |
CN (1) | CN116745281A (en) |
TW (1) | TW202300487A (en) |
WO (1) | WO2022210189A1 (en) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58172392A (en) * | 1982-04-02 | 1983-10-11 | Hidetoshi Tsuchida | Imidazole-coordinated hem complex included in cyclodextrin and gas-absorbing and desorbing agent |
WO1988008840A1 (en) * | 1987-05-04 | 1988-11-17 | Centre National De La Recherche Scientifique (Cnrs | Anti-tumoral targetting agents, preparation thereof and applications |
WO2007071028A1 (en) * | 2005-12-23 | 2007-06-28 | St. Mary's University | Compounds, complexes and uses thereof |
JP2010524895A (en) * | 2007-04-18 | 2010-07-22 | プロビオドルグ エージー | Cyanoguanidine derivatives as glutaminyl cyclase inhibitors |
CN104876936A (en) * | 2015-05-25 | 2015-09-02 | 中国人民解放军第二军医大学 | Preparation of 2-hydroxy-1, 2-di-2-pyridylethanone and pyrazole class compound and application as medicine |
CN106749407A (en) * | 2017-01-06 | 2017-05-31 | 中国工程物理研究院核物理与化学研究所 | A kind of phosphoramidic acid base functionalized ion liquid and its production and use |
WO2019238786A1 (en) * | 2018-06-12 | 2019-12-19 | Ryvu Therapeutics S.A. | Modulators of stimulator of interferon genes (sting) |
-
2022
- 2022-03-23 WO PCT/JP2022/013646 patent/WO2022210189A1/en active Application Filing
- 2022-03-23 KR KR1020237020573A patent/KR20230161929A/en unknown
- 2022-03-23 CN CN202280009235.XA patent/CN116745281A/en active Pending
- 2022-03-23 JP JP2023511074A patent/JPWO2022210189A1/ja active Pending
- 2022-03-29 TW TW111111928A patent/TW202300487A/en unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58172392A (en) * | 1982-04-02 | 1983-10-11 | Hidetoshi Tsuchida | Imidazole-coordinated hem complex included in cyclodextrin and gas-absorbing and desorbing agent |
WO1988008840A1 (en) * | 1987-05-04 | 1988-11-17 | Centre National De La Recherche Scientifique (Cnrs | Anti-tumoral targetting agents, preparation thereof and applications |
WO2007071028A1 (en) * | 2005-12-23 | 2007-06-28 | St. Mary's University | Compounds, complexes and uses thereof |
JP2010524895A (en) * | 2007-04-18 | 2010-07-22 | プロビオドルグ エージー | Cyanoguanidine derivatives as glutaminyl cyclase inhibitors |
CN104876936A (en) * | 2015-05-25 | 2015-09-02 | 中国人民解放军第二军医大学 | Preparation of 2-hydroxy-1, 2-di-2-pyridylethanone and pyrazole class compound and application as medicine |
CN106749407A (en) * | 2017-01-06 | 2017-05-31 | 中国工程物理研究院核物理与化学研究所 | A kind of phosphoramidic acid base functionalized ion liquid and its production and use |
WO2019238786A1 (en) * | 2018-06-12 | 2019-12-19 | Ryvu Therapeutics S.A. | Modulators of stimulator of interferon genes (sting) |
Non-Patent Citations (1)
Title |
---|
VINCENT GAUCHOT; MATHIEU BRANCA; ANDREEA SCHMITZER: "Encapsulation of a Catalytic Imidazolium Salt into Avidin: Towards the Development of a Biohybrid Catalyst Active in Ionic Liquids", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 20, no. 6, 2 January 2014 (2014-01-02), DE, pages 1530 - 1538, XP071840907, ISSN: 0947-6539, DOI: 10.1002/chem.201303865 * |
Also Published As
Publication number | Publication date |
---|---|
KR20230161929A (en) | 2023-11-28 |
TW202300487A (en) | 2023-01-01 |
JPWO2022210189A1 (en) | 2022-10-06 |
CN116745281A (en) | 2023-09-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2720844C (en) | Use of filler that undergoes endothermic phase transition to lower the reaction exotherm of epoxy based compositions | |
KR101571184B1 (en) | High Tg epoxy systems for composite application | |
JP5624054B2 (en) | Homogeneous bismaleimide-triazine-epoxy compositions useful in the manufacture of electrical laminates | |
JP4952866B2 (en) | Cationic polymerization initiator and thermosetting epoxy resin composition | |
US9334426B2 (en) | Latent curing agent and epoxy compositions containing the same | |
EP1848754B8 (en) | Low shrinkage amine-curing epoxy resin compositions comprising a lactone | |
SG172874A1 (en) | Metallic compounds in non-brominated flame retardant epoxy resins | |
CN105237737A (en) | Dicyandiamide type epoxy resin curing agent and preparation method and application thereof | |
WO2022210189A1 (en) | Curing catalyst, resin composition, sealing material, adhesive, and cured product | |
WO2022210190A1 (en) | Amine derivative | |
WO2021201060A1 (en) | Epoxy amine adduct, curing catalyst, resin composition, sealing material, adhesive and cured article | |
JP7316009B2 (en) | Curing catalysts, resin compositions, encapsulants, adhesives, and cured products | |
WO2023074450A1 (en) | Clathrate compound, epoxy resin curing agent, and curable resin composition | |
WO2024089905A1 (en) | Resin composition, adhesive, sealant, cured product, semiconductor device and electronic component | |
JP2012219134A (en) | Resin composition for electronic component, and liquid sealing material and electronic component device obtained by using the composition | |
JP2006022153A (en) | Curable resin composition | |
JP2007106787A (en) | Thermosetting resin composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22780404 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2023511074 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280009235.X Country of ref document: CN |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 22780404 Country of ref document: EP Kind code of ref document: A1 |