JP2016034906A - Triazine compound, synthesis method of the compound, and epoxy resin composition - Google Patents
Triazine compound, synthesis method of the compound, and epoxy resin composition Download PDFInfo
- Publication number
- JP2016034906A JP2016034906A JP2014157439A JP2014157439A JP2016034906A JP 2016034906 A JP2016034906 A JP 2016034906A JP 2014157439 A JP2014157439 A JP 2014157439A JP 2014157439 A JP2014157439 A JP 2014157439A JP 2016034906 A JP2016034906 A JP 2016034906A
- Authority
- JP
- Japan
- Prior art keywords
- chemical formula
- isocyanate
- triazine
- diamino
- compound represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Triazine compound Chemical class 0.000 title claims abstract description 96
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 34
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title abstract description 18
- 238000001308 synthesis method Methods 0.000 title abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 53
- 239000000853 adhesive Substances 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 13
- HRQQXWKHBIDOGH-UHFFFAOYSA-N 6-(2-aminoethyl)-1,3,5-triazine-2,4-diamine Chemical compound NCCC1=NC(N)=NC(N)=N1 HRQQXWKHBIDOGH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- 150000003918 triazines Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 11
- 239000000654 additive Substances 0.000 abstract description 4
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 4
- 239000011147 inorganic material Substances 0.000 abstract description 4
- 239000007769 metal material Substances 0.000 abstract description 4
- 230000005012 migration Effects 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 4
- 239000005011 phenolic resin Substances 0.000 abstract description 4
- 239000004645 polyester resin Substances 0.000 abstract description 4
- 229920001225 polyester resin Polymers 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 description 43
- 238000001723 curing Methods 0.000 description 14
- 239000004593 Epoxy Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 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 6
- 239000003566 sealing material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011810 insulating material Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- NIPQBUQQXPVFSH-UHFFFAOYSA-N CO[Si](CCCNC(=O)NCCC1=NC(=NC(=N1)N)N)(OC)OC Chemical compound CO[Si](CCCNC(=O)NCCC1=NC(=NC(=N1)N)N)(OC)OC NIPQBUQQXPVFSH-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- OZEHOHQZIRILDX-UHFFFAOYSA-N ctk1b7797 Chemical compound O=C1OC(=O)C2C1C1(C)CC2CC1 OZEHOHQZIRILDX-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000012567 medical material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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 compound 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
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- 0 *c(c(*)c1S)c(*)c(*)c1S(N=C=O)=* Chemical compound *c(c(*)c1S)c(*)c(*)c1S(N=C=O)=* 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- GOOVAYJIVMBWPP-UHFFFAOYSA-N 1-bromo-2-isocyanatobenzene Chemical compound BrC1=CC=CC=C1N=C=O GOOVAYJIVMBWPP-UHFFFAOYSA-N 0.000 description 1
- VQVBCZQTXSHJGF-UHFFFAOYSA-N 1-bromo-3-isocyanatobenzene Chemical compound BrC1=CC=CC(N=C=O)=C1 VQVBCZQTXSHJGF-UHFFFAOYSA-N 0.000 description 1
- CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- VZNCSZQPNIEEMN-UHFFFAOYSA-N 1-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC=C1N=C=O VZNCSZQPNIEEMN-UHFFFAOYSA-N 0.000 description 1
- RIKWVZGZRYDACA-UHFFFAOYSA-N 1-fluoro-3-isocyanatobenzene Chemical compound FC1=CC=CC(N=C=O)=C1 RIKWVZGZRYDACA-UHFFFAOYSA-N 0.000 description 1
- DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
- VVNMGFXOVZRKQF-UHFFFAOYSA-N 1-iodo-2-isocyanatobenzene Chemical compound IC1=CC=CC=C1N=C=O VVNMGFXOVZRKQF-UHFFFAOYSA-N 0.000 description 1
- LZSQANBVKPXBLO-UHFFFAOYSA-N 1-iodo-3-isocyanatobenzene Chemical compound IC1=CC=CC(N=C=O)=C1 LZSQANBVKPXBLO-UHFFFAOYSA-N 0.000 description 1
- KVMKUTIUJGYHBA-UHFFFAOYSA-N 1-iodo-4-isocyanatobenzene Chemical compound IC1=CC=C(N=C=O)C=C1 KVMKUTIUJGYHBA-UHFFFAOYSA-N 0.000 description 1
- QUOBVYPFBJUOAJ-UHFFFAOYSA-N 1-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1 QUOBVYPFBJUOAJ-UHFFFAOYSA-N 0.000 description 1
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
- NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
- XFEWMFDVBLLXFE-UHFFFAOYSA-N 1-isocyanatodecane Chemical compound CCCCCCCCCCN=C=O XFEWMFDVBLLXFE-UHFFFAOYSA-N 0.000 description 1
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- YJJKYKYXZZCJEE-UHFFFAOYSA-N 2,2-diphenylethylphosphane Chemical compound C=1C=CC=CC=1C(CP)C1=CC=CC=C1 YJJKYKYXZZCJEE-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
- JAYGNDDSBFXWLC-UHFFFAOYSA-N 2,4-dichloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C(Cl)=C1 JAYGNDDSBFXWLC-UHFFFAOYSA-N 0.000 description 1
- JSMSCEBQAVDZIX-UHFFFAOYSA-N 2,4-dimethyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C(C)=C1 JSMSCEBQAVDZIX-UHFFFAOYSA-N 0.000 description 1
- RHPCYVNTFRAYEO-UHFFFAOYSA-N 2,6-dichloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N=C=O RHPCYVNTFRAYEO-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-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
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- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、新規なトリアジン化合物、該化合物の合成方法およびエポキシ樹脂組成物に関する。 The present invention relates to a novel triazine compound, a method for synthesizing the compound, and an epoxy resin composition.
エポキシ樹脂、フェノール樹脂、ポリエステル樹脂等のポリマーは、熱硬化性であって且つ耐腐食性、電気絶縁性に優れているため、電子部品やプリント基板関連の分野において、接着剤、導電性ペースト、レジストインキや、封止材、絶縁材、基板用マトリックス材等の原料として、広く使用されている。
しかしながら、このようなポリマーは、マイグレーションを抑制する機能、即ち絶縁材上の配線（回路）や電極を構成する金属が、高湿度の環境下において、電位差により絶縁材上を移行する現象を抑える機能に乏しいため、電子部品やプリント基板の絶縁不良を招来すると云う難点があった。
また、それらのポリマーと、銅等の金属材料やガラス基板等の無機材料との、更なる密着性の改善も求められていた。
Polymers such as epoxy resins, phenol resins, and polyester resins are thermosetting and excellent in corrosion resistance and electrical insulation, so in the fields of electronic components and printed circuit boards, adhesives, conductive pastes, It is widely used as a raw material for resist inks, sealing materials, insulating materials, substrate matrix materials, and the like.
However, such a polymer has a function to suppress migration, that is, a function to suppress a phenomenon that a metal constituting a wiring (circuit) or an electrode on an insulating material moves on the insulating material due to a potential difference in a high humidity environment. Therefore, there is a problem that it causes an insulation failure of electronic parts and printed circuit boards.
In addition, further improvement in adhesion between these polymers and a metal material such as copper or an inorganic material such as a glass substrate has been demanded.
このような課題を解決するための添加剤として、種々の物質が使用されている。中でもトリアジン骨格を有する物質が、前記のマイグレーションの抑制や、種々の金属との密着性の改善に有効であるとされている。
例えば、２，４−ジアミノ−６−ビニル−１，３，５−トリアジンや、その類縁体を用いる方法が、鎌形らにより提案されている（非特許文献１、特許文献１〜３）。
しかしながら、これらのトリアジン誘導体に由来する密着性は未だ十分とは言えなかった。
Various substances are used as additives for solving such problems. Among them, a substance having a triazine skeleton is said to be effective for suppressing the migration and improving the adhesion with various metals.
For example, a method using 2,4-diamino-6-vinyl-1,3,5-triazine or an analog thereof has been proposed by Kamagata et al. (Non-patent Document 1, Patent Documents 1 to 3).
However, the adhesion derived from these triazine derivatives has not been sufficient yet.
本発明は、より高い密着性向上効果を発揮するトリアジン化合物、該化合物の合成方法および該化合物を含有するエポキシ樹脂組成物を提供することを目的とする。 An object of this invention is to provide the triazine compound which exhibits the higher adhesive improvement effect, the synthesis method of this compound, and the epoxy resin composition containing this compound.
本発明者らは、前記の課題を解決するために鋭意研究を重ねた結果、ウレア結合を有するトリアジン化合物とすることにより、所期の目的を達成し得ることを見出し、本発明を完成するに至ったものである。
即ち、第１の発明は、化学式（I）、化学式（II）、化学式（III）または化学式（IV）で示されるトリアジン化合物である。
As a result of intensive studies to solve the above problems, the present inventors have found that the intended purpose can be achieved by using a triazine compound having a urea bond, and the present invention is completed. It has come.
That is, the first invention is a triazine compound represented by chemical formula (I), chemical formula (II), chemical formula (III) or chemical formula (IV).
第２の発明は、化学式（V）で示される２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンと、化学式（VI）で示されるイソシアネート化合物を反応させることを特徴とする前記化学式（I）で示されるトリアジン化合物の合成方法である。 In the second invention, 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine represented by the chemical formula (V) is reacted with the isocyanate compound represented by the chemical formula (VI). A method for synthesizing a triazine compound represented by the chemical formula (I).
第３の発明は、化学式（V）で示される２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンと、化学式（VII）で示されるイソシアネート化合物を反応させることを特徴とする前記化学式（II）で示されるトリアジン化合物の合成方法である。 The third invention is to react 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine represented by the chemical formula (V) with an isocyanate compound represented by the chemical formula (VII). A method for synthesizing a triazine compound represented by the chemical formula (II).
第４の発明は、化学式（V）で示される２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンと、化学式（VIII）で示されるイソシアネート化合物を反応させることを特徴とする前記化学式（III）で示されるトリアジン化合物の合成方法である。 The fourth invention is to react 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine represented by the chemical formula (V) with an isocyanate compound represented by the chemical formula (VIII). A method for synthesizing a triazine compound represented by the chemical formula (III).
第５の発明は、化学式（V）で示される２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンと、化学式（IX）で示されるイソシアネート化合物を反応させることを特徴とする前記化学式（IV）で示されるトリアジン化合物の合成方法。 The fifth invention is to react 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine represented by the chemical formula (V) with an isocyanate compound represented by the chemical formula (IX). A method for synthesizing a triazine compound represented by the above chemical formula (IV).
第６の発明は、第１の発明のトリアジン化合物を１種または２種以上含有することを特徴とするエポキシ樹脂組成物である。 A sixth invention is an epoxy resin composition characterized by containing one or more of the triazine compounds of the first invention.
第７の発明は、第１の発明のトリアジン化合物を１種または２種以上含有することを特徴とする接着剤用またはシール剤用エポキシ樹脂組成物である。 A seventh invention is an epoxy resin composition for adhesives or sealants, characterized by containing one or more of the triazine compounds of the first invention.
本発明のトリアジン化合物を、エポキシ樹脂、フェノール樹脂、ポリエステル樹脂、アクリル樹脂、ポリスチレン樹脂等のポリマーの添加剤として使用した場合には、当該トリアジン化合物がポリマー中に溶解または均一に分散して、電子部品やプリント基板等のマイグレーションの防止や、電子部品やプリント基板を構成する鉄、アルミ、銅、銀、白金等の金属材料および無機材料と、ポリマーとの密着性を高める効果を発揮することが期待される。 When the triazine compound of the present invention is used as an additive for a polymer such as an epoxy resin, a phenol resin, a polyester resin, an acrylic resin, or a polystyrene resin, the triazine compound is dissolved or uniformly dispersed in the polymer, and It can prevent migration of components and printed circuit boards, and can improve the adhesion between polymers and metal materials such as iron, aluminum, copper, silver, platinum, and inorganic materials that make up electronic components and printed circuit boards. Be expected.
以下、本発明を詳細に説明する。
本発明は、前記の化学式（I）、化学式（II）、化学式（III）または化学式（IV）で示されるトリアジン化合物であり、分子中にウレア結合を有する。
Hereinafter, the present invention will be described in detail.
The present invention is a triazine compound represented by the aforementioned chemical formula (I), chemical formula (II), chemical formula (III) or chemical formula (IV), and has a urea bond in the molecule.
化学式（I）で示されるトリアジン化合物の例としては、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−メチルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−エチルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−プロピルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−ブチルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−ヘキシルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−オクチルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−デシルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−ドデシルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−オクタデシルウレア等が挙げられる。
As an example of the triazine compound represented by the chemical formula (I),
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-methylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-ethylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-propylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-butylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-hexylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-octylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-decylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-dodecylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-octadecylurea and the like.
化学式（II）で示されるトリアジン化合物の例としては、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−［３−（トリメトキシシリル）プロピル］ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−［３−（トリエトキシシリル）プロピル］ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−［３−（トリイソプロポキシシリル）プロピル］ウレア等が挙げられる。
As an example of the triazine compound represented by the chemical formula (II),
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- [3- (trimethoxysilyl) propyl] urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- [3- (triethoxysilyl) propyl] urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- [3- (triisopropoxysilyl) propyl] urea and the like.
化学式（III）で示されるトリアジン化合物の例としては、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−フェニルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−メチルフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−メチルフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−メチルフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２，４−ジメチルフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２，６−ジメチルフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−クロロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−クロロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−クロロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２，４−ジクロロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２，６−ジクロロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−フルオロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−フルオロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−フルオロフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−ブロモフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−ブロモフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−ブロモフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−ヨードフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−ヨードフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−ヨードフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−ヒドロキシフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−ヒドロキシフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−ヒドロキシフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−メトキシフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−メトキシフェニル）ウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−メトキシフェニル）ウレア等が挙げられる。
As an example of the triazine compound represented by the chemical formula (III),
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-phenylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-methylphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-methylphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-methylphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2,4-dimethylphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2,6-dimethylphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-chlorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-chlorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-chlorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2,4-dichlorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2,6-dichlorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-fluorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-fluorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-fluorophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-bromophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-bromophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-bromophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-iodophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-iodophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-iodophenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-hydroxyphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-hydroxyphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-hydroxyphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-methoxyphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-methoxyphenyl) urea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-methoxyphenyl) urea and the like.
化学式（IV）で表されるトリアジン化合物の例としては、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−フェニルスルホニルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（２−メチルフェニル）スルホニルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（３−メチルフェニル）スルホニルウレア、
１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−（４−メチルフェニル）スルホニルウレア等が挙げられる。
As an example of the triazine compound represented by the chemical formula (IV),
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3-phenylsulfonylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (2-methylphenyl) sulfonylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (3-methylphenyl) sulfonylurea,
1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- (4-methylphenyl) sulfonylurea and the like.
これらのトリアジン化合物は、前記の化学式（V）で示される２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンと、前記の化学式（VI）、化学式（VII）、化学式（VIII）または化学式（IX）で示されるイソシアネート化合物を、適量の反応溶媒中において、適宜の反応温度および反応時間にて反応させることにより合成することができる。 These triazine compounds include 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine represented by the chemical formula (V), the chemical formula (VI), and the chemical formula (VII). It can be synthesized by reacting the isocyanate compound represented by the chemical formula (VIII) or the chemical formula (IX) in an appropriate amount of reaction solvent at an appropriate reaction temperature and reaction time.
化学式（VI）で示されるイソシアネート化合物の例としては、
メチルイソシアネート、
エチルイソシアネート、
プロピルイソシアネート、
ブチルイソシアネート、
ヘキシルイソシアネート、
オクチルイソシアネート、
デシルイソシアネート、
ドデシルイソシアネート、
オクタデシルイソシアネート
等が挙げられる。
As an example of the isocyanate compound represented by the chemical formula (VI),
Methyl isocyanate,
Ethyl isocyanate,
Propyl isocyanate,
Butyl isocyanate,
Hexyl isocyanate,
Octyl isocyanate,
Decyl isocyanate,
Dodecyl isocyanate,
Examples include octadecyl isocyanate.
化学式（VII）で示されるイソシアネート化合物の例としては、
３−（トリメトキシシリル）プロピルイソシアネート、
３−（トリエトキシシリル）プロピルイソシアネート、
３−（トリイソプロポキシシリル）プロピルイソシアネート
等が挙げられる。
As an example of the isocyanate compound represented by the chemical formula (VII),
3- (trimethoxysilyl) propyl isocyanate,
3- (triethoxysilyl) propyl isocyanate,
Examples include 3- (triisopropoxysilyl) propyl isocyanate.
化学式（VIII）で示されるイソシアネート化合物の例としては、
フェニルイソシアネート、
２−メチルフェニルイソシアネート、
３−メチルフェニルイソシアネート、
４−メチルフェニルイソシアネート、
２，４−ジメチルフェニルイソシアネート、
２，６−ジメチルフェニルイソシアネート、
２−クロロフェニルイソシアネート、
３−クロロフェニルイソシアネート、
４−クロロフェニルイソシアネート、
２，４−ジクロロフェニルイソシアネート、
２，６−ジクロロフェニルイソシアネート、
２−フルオロフェニルイソシアネート、
３−フルオロフェニルイソシアネート、
４−フルオロフェニルイソシアネート、
２−ブロモフェニルイソシアネート、
３−ブロモフェニルイソシアネート、
４−ブロモフェニルイソシアネート、
２−ヨードフェニルイソシアネート、
３−ヨードフェニルイソシアネート、
４−ヨードフェニルイソシアネート、
２−ヒドロキシフェニルイソシアネート、
３−ヒドロキシフェニルイソシアネート、
４−ヒドロキシフェニルイソシアネート、
２−メトキシフェニルイソシアネート、
３−メトキシフェニルイソシアネート、
４−メトキシフェニルイソシアネート
等が挙げられる。
As an example of the isocyanate compound represented by the chemical formula (VIII),
Phenyl isocyanate,
2-methylphenyl isocyanate,
3-methylphenyl isocyanate,
4-methylphenyl isocyanate,
2,4-dimethylphenyl isocyanate,
2,6-dimethylphenyl isocyanate,
2-chlorophenyl isocyanate,
3-chlorophenyl isocyanate,
4-chlorophenyl isocyanate,
2,4-dichlorophenyl isocyanate,
2,6-dichlorophenyl isocyanate,
2-fluorophenyl isocyanate,
3-fluorophenyl isocyanate,
4-fluorophenyl isocyanate,
2-bromophenyl isocyanate,
3-bromophenyl isocyanate,
4-bromophenyl isocyanate,
2-iodophenyl isocyanate,
3-iodophenyl isocyanate,
4-iodophenyl isocyanate,
2-hydroxyphenyl isocyanate,
3-hydroxyphenyl isocyanate,
4-hydroxyphenyl isocyanate,
2-methoxyphenyl isocyanate,
3-methoxyphenyl isocyanate,
4-methoxyphenyl isocyanate and the like can be mentioned.
化学式（IX）で示されるイソシアネート化合物の例としては、
ベンゼンスルホニルイソシアネート、
２−メチルベンゼンスルホニルイソシアネート、
３−メチルベンゼンスルホニルイソシアネート、
４−メチルベンゼンスルホニルイソシアネート、
２，４−ジメチルベンゼンスルホニルイソシアネート、
２，６−ジメチルベンゼンスルホニルイソシアネート、
２−クロロベンゼンスルホニルイソシアネート、
３−クロロベンゼンスルホニルイソシアネート、
４−クロロベンゼンスルホニルイソシアネート、
２，４−ジクロロベンゼンスルホニルイソシアネート、
２，６−ジクロロベンゼンスルホニルイソシアネート、
２−フルオロベンゼンスルホニルイソシアネート、
３−フルオロベンゼンスルホニルイソシアネート、
４−フルオロベンゼンスルホニルイソシアネート、
２−ブロモベンゼンスルホニルイソシアネート、
３−ブロモベンゼンスルホニルイソシアネート、
４−ブロモベンゼンスルホニルイソシアネート、
２−ヨードベンゼンスルホニルイソシアネート、
３−ヨードベンゼンスルホニルイソシアネート、
４−ヨードベンゼンスルホニルイソシアネート、
２−ヒドロキシベンゼンスルホニルイソシアネート、
３−ヒドロキシベンゼンスルホニルイソシアネート、
４−ヒドロキシベンゼンスルホニルイソシアネート、
２−メトキシベンゼンスルホニルイソシアネート、
３−メトキシベンゼンスルホニルイソシアネート、
４−メトキシベンゼンスルホニルイソシアネート
等が挙げられる。
As an example of the isocyanate compound represented by the chemical formula (IX),
Benzenesulfonyl isocyanate,
2-methylbenzenesulfonyl isocyanate,
3-methylbenzenesulfonyl isocyanate,
4-methylbenzenesulfonyl isocyanate,
2,4-dimethylbenzenesulfonyl isocyanate,
2,6-dimethylbenzenesulfonyl isocyanate,
2-chlorobenzenesulfonyl isocyanate,
3-chlorobenzenesulfonyl isocyanate,
4-chlorobenzenesulfonyl isocyanate,
2,4-dichlorobenzenesulfonyl isocyanate,
2,6-dichlorobenzenesulfonyl isocyanate,
2-fluorobenzenesulfonyl isocyanate,
3-fluorobenzenesulfonyl isocyanate,
4-fluorobenzenesulfonyl isocyanate,
2-bromobenzenesulfonyl isocyanate,
3-bromobenzenesulfonyl isocyanate,
4-bromobenzenesulfonyl isocyanate,
2-iodobenzenesulfonyl isocyanate,
3-iodobenzenesulfonyl isocyanate,
4-iodobenzenesulfonyl isocyanate,
2-hydroxybenzenesulfonyl isocyanate,
3-hydroxybenzenesulfonyl isocyanate,
4-hydroxybenzenesulfonyl isocyanate,
2-methoxybenzenesulfonyl isocyanate,
3-methoxybenzenesulfonyl isocyanate,
Examples include 4-methoxybenzenesulfonyl isocyanate.
前記の反応溶媒の例としては、メタノール、エタノール等のアルコール系溶剤、クロロホルム、ジクロロメタン等のハロゲン系溶剤、トルエン、ヘキサン等の炭化水素系溶剤、テトラヒドロフラン、１，４−ジオキサン等のエーテル系溶剤およびジメチルスルホキシド（ＤＭＳＯ）等が挙げられる。 Examples of the reaction solvent include alcohol solvents such as methanol and ethanol, halogen solvents such as chloroform and dichloromethane, hydrocarbon solvents such as toluene and hexane, ether solvents such as tetrahydrofuran and 1,4-dioxane, and the like. Examples thereof include dimethyl sulfoxide (DMSO).
前記の反応温度については、１０〜１００℃の範囲内で適宜設定することができる。また、前記の反応時間については、設定した反応温度に応じて決定されるが、０．５〜２４時間とすることが好ましく、１〜６時間とすることがより好ましい。 About the said reaction temperature, it can set suitably in the range of 10-100 degreeC. The reaction time is determined according to the set reaction temperature, but is preferably 0.5 to 24 hours, and more preferably 1 to 6 hours.
本発明のトリアジン化合物は、硬化剤と共に、更に必要に応じて硬化剤および硬化促進剤（硬化触媒）と共に、エポキシ化合物に１種または２種以上配合して、エポキシ樹脂組成物とすることができる。
前記のエポキシ化合物は、分子内に少なくとも２つのエポキシ基を有していればよいが、分子内に少なくとも２つのエポキシ基を有する物質と、分子内に１つのエポキシ基を有する物質の混合物であってもよい。
The triazine compound of the present invention can be blended with an epoxy compound together with a curing agent, and optionally with a curing agent and a curing accelerator (curing catalyst) to form an epoxy resin composition. .
The epoxy compound may have at least two epoxy groups in the molecule, but is a mixture of a substance having at least two epoxy groups in the molecule and a substance having one epoxy group in the molecule. May be.
この場合における本発明のトリアジン化合物の配合量は、エポキシ化合物１００重量部に対して、０．０１〜１５０重量部の割合とすることが好ましく、０．１〜５０重量部の割合とすることがより好ましい。
そして、硬化剤の配合量は、エポキシ化合物１００重量部に対して、０．０１〜３００重量部の割合とすることが好ましく、０．１〜２００重量部の割合とすることがより好ましい。
また、硬化促進剤の配合量は、エポキシ化合物１００重量部に対して０．０１〜２．０重量部の割合とすることが好ましく、０．１〜０．５重量部の割合とすることがより好ましい。
In this case, the amount of the triazine compound of the present invention is preferably 0.01 to 150 parts by weight, more preferably 0.1 to 50 parts by weight, based on 100 parts by weight of the epoxy compound. More preferred.
And it is preferable to set it as the ratio of 0.01-300 weight part with respect to 100 weight part of epoxy compounds, and, as for the compounding quantity of a hardening | curing agent, it is more preferable to set it as the ratio of 0.1-200 weight part.
Moreover, it is preferable to make the compounding quantity of a hardening accelerator into the ratio of 0.01-2.0 weight part with respect to 100 weight part of epoxy compounds, and to set it as the ratio of 0.1-0.5 weight part. More preferred.
前記のエポキシ化合物の例としては、
ビスフェノールＡ型エポキシ樹脂、
ビスフェノールＦ型エポキシ樹脂、
フェノールノボラック型エポキシ樹脂やクレゾールノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂、
脂環式エポキシ樹脂、
３′，４′−エポキシシクロヘキシルメチル−３，４−エポキシシクロヘキサンカルボキシレートのような環状脂環式エポキシ樹脂、
１，３，４，６−テトラグリシジルグリコールウリル、
１，３，４，６−テトラグリシジル−３ａ，６ａ−ジメチルグリコールウリル、
１，３，４，６−テトラグリシジル−３ａ，６ａ−ジフェニルグリコールウリル、
トリグリシジルイソシアヌレート、
モノアリルジグリシジルイソシアヌレート、
ジアリルモノグリシジルイソシアヌレートやヒダントイン型エポキシ樹脂等の含窒素環状エポキシ樹脂、
水添ビスフェノールＡ型エポキシ樹脂、
脂肪族系エポキシ樹脂、
グリシジルエーテル型エポキシ樹脂、
ビスフェノールＳ型エポキシ樹脂、
ビフェニル型エポキシ樹脂、
ジシクロ環型エポキシ樹脂、
ナフタレン型エポキシ樹脂やハロゲン化エポキシ樹脂等の他、
炭素−炭素二重結合およびグリシジル基を有する有機化合物と、ＳｉＨ基を有するケイ素化合物とのヒドロシリル化付加反応によるエポキシ変性オルガノポリシロキサン化合物（例えば、特開２００４−９９７５１号公報や特開２００６−２８２９８８号公報に開示されたエポキシ変性オルガノポリシロキサン化合物）が挙げられる。
なお、ここで云うエポキシ樹脂とは、硬化前のエポキシ化合物を指す。
As an example of the epoxy compound,
Bisphenol A type epoxy resin,
Bisphenol F type epoxy resin,
Novolac epoxy resins such as phenol novolac epoxy resins and cresol novolac epoxy resins,
Alicyclic epoxy resin,
Cyclic alicyclic epoxy resins such as 3 ', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate;
1,3,4,6-tetraglycidylglycoluril,
1,3,4,6-tetraglycidyl-3a, 6a-dimethylglycoluril,
1,3,4,6-tetraglycidyl-3a, 6a-diphenylglycoluril,
Triglycidyl isocyanurate,
Monoallyl diglycidyl isocyanurate,
Nitrogen-containing cyclic epoxy resins such as diallyl monoglycidyl isocyanurate and hydantoin type epoxy resins,
Hydrogenated bisphenol A type epoxy resin,
Aliphatic epoxy resin,
Glycidyl ether type epoxy resin,
Bisphenol S type epoxy resin,
Biphenyl type epoxy resin,
Dicyclo ring type epoxy resin,
In addition to naphthalene type epoxy resins and halogenated epoxy resins,
Epoxy-modified organopolysiloxane compounds by hydrosilylation addition reaction between an organic compound having a carbon-carbon double bond and a glycidyl group and a silicon compound having an SiH group (for example, JP-A-2004-99751 and JP-A-2006-282888) Epoxy-modified organopolysiloxane compounds disclosed in Japanese Patent Publication No.
In addition, the epoxy resin here refers to the epoxy compound before hardening.
前記の硬化剤の例としては、
フェノール性水酸基を有する化合物、
酸無水物やアミン類の他、
メルカプトプロピオン酸エステル、
エポキシ樹脂末端メルカプト化合物等のメルカプタン化合物、
トリフェニルホスフィン、
ジフェニルナフチルホスフィン、
ジフェニルエチルホスフィン等の有機ホスフィン系化合物、
芳香族ホスホニウム塩、
芳香族ジアゾニウム塩、
芳香族ヨードニウム塩、
芳香族セレニウム塩等が挙げられる。
As an example of the curing agent,
A compound having a phenolic hydroxyl group,
In addition to acid anhydrides and amines,
Mercaptopropionic acid ester,
Mercaptan compounds such as epoxy resin-terminated mercapto compounds,
Triphenylphosphine,
Diphenylnaphthylphosphine,
Organic phosphine compounds such as diphenylethylphosphine,
Aromatic phosphonium salts,
Aromatic diazonium salts,
Aromatic iodonium salt,
Aromatic selenium salts and the like can be mentioned.
前記のフェノール性水酸基を有する化合物の例としては、
ビスフェノールＡ、
ビスフェノールＦ、
ビスフェノールＳ、
テトラメチルビスフェノールＡ、
テトラメチルビスフェノールＦ、
テトラメチルビスフェノールＳ、
テトラクロロビスフェノールＡ、
テトラブロモビスフェノールＡ、
ジヒドロキシナフタレン、
フェノールノボラック、
クレゾールノボラック、
ビスフェノールＡノボラック、
臭素化フェノールノボラック、
レゾルシノール等が挙げられる。
Examples of the compound having a phenolic hydroxyl group include
Bisphenol A,
Bisphenol F,
Bisphenol S,
Tetramethylbisphenol A,
Tetramethylbisphenol F,
Tetramethylbisphenol S,
Tetrachlorobisphenol A,
Tetrabromobisphenol A,
Dihydroxynaphthalene,
Phenol novolac,
Cresol novolac,
Bisphenol A novolak,
Brominated phenol novolac,
Resorcinol and the like can be mentioned.
前記の酸無水物の例としては、
メチルテトラヒドロ無水フタル酸、
メチルヘキサヒドロ無水フタル酸、
ヘキサヒドロ無水フタル酸、
５−ノルボルネン−２，３−ジカルボン酸無水物、
無水トリメリット酸、
ナジック酸無水物、
ハイミック酸無水物、
メチルナジック酸無水物、
メチルビシクロ［２．２．１］ヘプタン−２，３−ジカルボン酸無水物、
ビシクロ［２．２．１］ヘプタン−２，３−ジカルボン酸無水物、
メチルノルボルナン−２，３−ジカルボン酸無水物等が挙げられる。
Examples of the acid anhydride include
Methyltetrahydrophthalic anhydride,
Methyl hexahydrophthalic anhydride,
Hexahydrophthalic anhydride,
5-norbornene-2,3-dicarboxylic anhydride,
Trimellitic anhydride,
Nadic acid anhydride,
Highmic anhydride,
Methyl nadic anhydride,
Methylbicyclo [2.2.1] heptane-2,3-dicarboxylic anhydride,
Bicyclo [2.2.1] heptane-2,3-dicarboxylic anhydride,
And methylnorbornane-2,3-dicarboxylic acid anhydride.
前記のアミン類の例としては、
ジエチレンジアミン、
トリエチレンテトラミン、
ヘキサメチレンジアミン、
ダイマー酸変性エチレンジアミン、
４，４′−ジアミノジフェニルスルホン、
４，４′−ジアミノジフェノールエーテル、
１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等や、
２−メチルイミダゾール、
２−エチル−４−メチルイミダゾール、
２−フェニルイミダゾール等のイミダゾール化合物が挙げられる。
Examples of the amines include
Diethylenediamine,
Triethylenetetramine,
Hexamethylenediamine,
Dimer acid-modified ethylenediamine,
4,4'-diaminodiphenyl sulfone,
4,4'-diaminodiphenol ether,
1,8-diazabicyclo [5.4.0] -7-undecene, etc.
2-methylimidazole,
2-ethyl-4-methylimidazole,
Examples include imidazole compounds such as 2-phenylimidazole.
前記の硬化促進剤の例としては、
１，８−ジアザビシクロ［５．４．０］−７−ウンデセン、ジエチレントリアミン、トリエチレンテトラミン、ベンジルジメチルアミン、トリエタノールアミン、ジメチルアミノエタノール、トリス(ジメチルアミノメチル)フェノール等のアミン化合物、
２−メチルイミダゾール、２−フェニルイミダゾール、２−フェニル−４−メチルイミダゾール、２−ヘプタデシルイミダゾール等のイミダゾール化合物、
トリブチルホスフィン、メチルジフェニルホスフィン、トリフェニルホスフィン、ジフェニルホスフィン、フェニルホスフィン等の有機ホスフィン化合物、
テトラブチルホスフォニウムブロマイド、テトラブチルホスホニウムジエチルホスホロジチオネート等のホスホニウム化合物、
テトラフェニルホスホニウム・テトラフェニルボレート、２−メチル−４−メチルイミダゾール・テトラフェニルボレート、Ｎ−メチルモルホリン・テトラフェニルボレート等のテトラフェニルボロン塩、
酢酸鉛、
オクチル酸錫、
ヘキサン酸コバルト等の脂肪族酸金属塩等が挙げられる。
なお、これらの物質のうちの一部は、前述の硬化剤としても使用される。
Examples of the curing accelerator include
Amine compounds such as 1,8-diazabicyclo [5.4.0] -7-undecene, diethylenetriamine, triethylenetetramine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol,
Imidazole compounds such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-heptadecylimidazole,
Organic phosphine compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine, phenylphosphine,
Phosphonium compounds such as tetrabutylphosphonium bromide, tetrabutylphosphonium diethyl phosphorodithioate,
Tetraphenylboron salts such as tetraphenylphosphonium tetraphenylborate, 2-methyl-4-methylimidazole tetraphenylborate, N-methylmorpholine tetraphenylborate,
Lead acetate,
Tin octylate,
Examples thereof include aliphatic acid metal salts such as cobalt hexanoate.
Some of these substances are also used as the aforementioned curing agent.
本発明のエポキシ樹脂組成物には、必要に応じて非晶性シリカ、結晶性シリカ、炭酸カルシウム、炭酸マグネシウム、アルミナ、マグネシア、クレー、タルク、ケイ酸カルシウム、酸化チタン等の無機充填材、セルロース、ガラス繊維、ボロン繊維、炭素繊維等の繊維状充填材、カーボンブラック、グラファイト、カーボンナノチューブ、フラーレン、酸化鉄、金、銀、アルミニウム粉、鉄粉、ニッケル、銅、亜鉛、クロム、半田、ナノサイズの金属結晶、金属間化合物等の導電性充填材、フェノール樹脂、ポリエステル樹脂、アクリル樹脂、ポリスチレン樹脂、ポリウレタン樹脂、ポリエーテル樹脂、メラミン樹脂、アクリル変性エポキシ樹脂、ウレタン変性エポキシ樹脂、ゴム変性エポキシ樹脂、アルキッド変性エポキシ樹脂等の各種ポリマーの他、エチレングリコール、プロピレングリコール等の脂肪族ポリオール、脂肪族または芳香族カルボン酸化合物、フェノール化合物等の炭酸ガス発生防止剤、ポリアルキレングリコール等の可撓性付与剤、酸化防止剤、可塑剤、滑剤、シラン系等のカップリング剤、無機充填材の表面処理剤、難燃剤、帯電防止剤、着色剤、帯電防止剤、レベリング剤、イオントラップ剤、摺動性改良剤、各種ゴム、耐衝撃性改良剤、揺変性付与剤、界面活性剤、表面張力低下剤、消泡剤、沈降防止剤、光拡散剤、紫外線吸収剤、抗酸化剤、離型剤、蛍光剤等の添加剤を配合することができる。 The epoxy resin composition of the present invention includes an inorganic filler such as amorphous silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, and titanium oxide as necessary. , Fiber filler such as glass fiber, boron fiber, carbon fiber, carbon black, graphite, carbon nanotube, fullerene, iron oxide, gold, silver, aluminum powder, iron powder, nickel, copper, zinc, chromium, solder, nano Size metal crystals, conductive fillers such as intermetallic compounds, phenol resin, polyester resin, acrylic resin, polystyrene resin, polyurethane resin, polyether resin, melamine resin, acrylic modified epoxy resin, urethane modified epoxy resin, rubber modified epoxy Various types of resin, alkyd-modified epoxy resin, etc. In addition to polymers, aliphatic polyols such as ethylene glycol and propylene glycol, aliphatic or aromatic carboxylic acid compounds, carbon dioxide generation inhibitors such as phenol compounds, flexibility imparting agents such as polyalkylene glycols, antioxidants, plastics Agents, lubricants, silane-based coupling agents, inorganic filler surface treatment agents, flame retardants, antistatic agents, coloring agents, antistatic agents, leveling agents, ion trapping agents, sliding properties improving agents, various rubbers, Additives such as impact resistance improvers, thixotropic agents, surfactants, surface tension reducing agents, antifoaming agents, anti-settling agents, light diffusing agents, ultraviolet absorbers, antioxidants, mold release agents, fluorescent agents, etc. Can be blended.
また、本発明のエポキシ樹脂組成物には、該エポキシ樹脂組成物の溶剤（溶液）化や粘度調整の為に、トルエン、キシレン、メチルエチルケトン、メチルイソブチルケトン、酢酸エチル、酢酸ブチル等の有機溶剤、ブチルグリシジルエーテル、Ｎ，Ｎ′−ジグリシジル−ｏ−トルイジン、フェニルグリシジルエーテル、スチレンオキサイド、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、１，６−ヘキサンジオールジグリシジルエーテル等の反応性希釈剤、ジオクチルフタレート、ジブチルフタレート、ジオクチルアジベート、石油系溶剤等の非反応性の希釈剤を配合することができる。 The epoxy resin composition of the present invention includes an organic solvent such as toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, and butyl acetate for solvent (solution) and viscosity adjustment of the epoxy resin composition, Reactive diluents such as butyl glycidyl ether, N, N′-diglycidyl-o-toluidine, phenyl glycidyl ether, styrene oxide, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, Non-reactive diluents such as dioctyl phthalate, dibutyl phthalate, dioctyl adipate and petroleum solvents can be blended.
本発明のエポキシ樹脂組成物は、その調製方法に特に制限はなく、前述の各成分を所定量計り取って撹拌混合することにより調製される。例えば、予備混合の後、ロール混練機、ニーダーや押出機等を用いて、混合あるいは溶融混練することにより調製することもできる。 The epoxy resin composition of the present invention is not particularly limited in its preparation method, and is prepared by measuring a predetermined amount of each of the aforementioned components and stirring and mixing them. For example, it can be prepared by mixing or melt-kneading using a roll kneader, a kneader, an extruder or the like after preliminary mixing.
本発明のエポキシ樹脂組成物は、その硬化方法に特に制限はなく、密閉式硬化炉や連続硬化が可能なトンネル炉等の従来公知の硬化装置を採用することができる。加熱源についても特に制約されることなく、熱風循環、赤外線加熱、高周波加熱等、従来公知の方法を採用することができる。硬化温度および硬化時間は、適宜設定すればよい。 The epoxy resin composition of the present invention is not particularly limited in its curing method, and a conventionally known curing device such as a closed curing furnace or a tunnel furnace capable of continuous curing can be employed. The heating source is not particularly limited, and conventionally known methods such as hot air circulation, infrared heating, and high frequency heating can be employed. The curing temperature and the curing time may be set as appropriate.
本発明のトリアジン化合物を１種または２種以上配合したエポキシ樹脂組成物の使用用途に特に制限はなく、樹脂製材料が使用される様々な分野、製品に適用することが可能であり、電気・電子材料用途、建築用途、土木用途、自動車用途、医療材料用途等に広く使用できる。 There are no particular restrictions on the usage of the epoxy resin composition containing one or more of the triazine compounds of the present invention, and it can be applied to various fields and products where resinous materials are used. It can be widely used for electronic material applications, architectural applications, civil engineering applications, automobile applications, medical material applications, and the like.
例えば、電気・電子材料用途における例としては、接着剤、シール剤、半導体封止剤、絶縁材料、熱伝導性材料、ホットメルト材料、塗料、ポッティング剤等が挙げられるが、より具体的には、プリント配線基板、層間絶縁膜、配線被覆膜等の電子部品の封止材料や層形成材料、カラーフィルター、フレキシブルディスプレイ用フィルム、レジスト材料、配向膜等の表示装置の形成材料、レジスト材料、バッファーコート膜等の半導体装置の形成材料、ホログラム、光導波路、光回路、光回路部品、反射防止膜等の光学部品の形成材料が挙げられる。 For example, examples of applications in electrical / electronic materials include adhesives, sealants, semiconductor sealants, insulating materials, heat conductive materials, hot melt materials, paints, potting agents, etc. Sealing materials and layer forming materials for electronic parts such as printed wiring boards, interlayer insulating films, wiring coating films, color filters, flexible display films, resist materials, forming materials for display devices such as alignment films, resist materials, Examples include a material for forming a semiconductor device such as a buffer coat film, and a material for forming an optical component such as a hologram, an optical waveguide, an optical circuit, an optical circuit component, and an antireflection film.
また、建築用途における材料の例としては、各種金属パネル・サイディングボード等の外装材の目地用シール材、コーティング材、プライマー等、外装材・下地材・天井材と内装材の間に使用するシール材、接着剤、注入材、制振材、防音材、電磁波遮蔽用導電性材料、パテ材等、外壁材・下地材へのタイル・石材接着用の接着剤、各種床への木質フローリング材・高分子材料系床シート・床タイル接着用の接着剤、粘着剤等、各種外装材・内装材のクラック補修用注入材等が挙げられ、土木用途における材料の例としては、道路・橋梁・トンネル・防波堤・各種コンクリート製品の目地用シール材、コーティング材、プライマー、塗料、注入材、パテ材、型取材、吹付材等が挙げられ、自動車用途における材料の例としては、自動車ボディーのシール材、コーティング材、緩衝材、制振材、防音材、吹付材等、自動車内装用の接着剤、粘着材、コーティング材、発泡材料等、自動車部品のシール材、接着剤等、トラック・バス等の各種鋼板継ぎ目用のシール材、接着剤、コーティング材等が挙げられ、医療材料用途における例としては、医療用ゴム材料、医療用粘着剤、医療機器シール材等が挙げられる。 Examples of materials used in building applications include seals used for joints between exterior materials such as various metal panels and exterior materials such as siding boards, coating materials and primers, and exterior materials, base materials, ceiling materials, and interior materials. Materials, adhesives, injection materials, damping materials, soundproofing materials, conductive materials for shielding electromagnetic waves, putty materials, etc., adhesives for tiles and stone materials to outer wall materials and base materials, wood flooring materials for various floors Polymer material floor sheets, adhesives for floor tile adhesion, adhesives, cracking injection materials for various exterior materials and interior materials, etc. Examples of materials in civil engineering applications include roads, bridges, tunnels -Seals for breakwaters and various concrete products, coating materials, primers, paints, injection materials, putty materials, molding materials, spray materials, etc. Examples of materials in automotive applications include automobile bodies Sealing materials, coating materials, cushioning materials, damping materials, soundproofing materials, spraying materials, etc., automotive interior adhesives, adhesive materials, coating materials, foamed materials, etc., automotive parts sealing materials, adhesives, etc. Examples include sealing materials for various steel plate joints such as baths, adhesives, and coating materials. Examples of medical materials include medical rubber materials, medical adhesives, and medical device sealing materials.
以下、本発明を実施例によって具体的に説明するが、本発明はこれらに限定されるものではない。実施例の合成試験に使用した主原料は、以下のとおりである。なお、２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジンは、特開昭６１−２１００７６号公報に記載の方法で合成した。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. The main raw materials used in the synthesis tests of the examples are as follows. 2,4-Diamino-6- (2-aminoethyl) -1,3,5-triazine was synthesized by the method described in JP-A No. 61-210076.
［主原料］
・３−（トリメトキシシリル）プロピルイソシアネート（東京化成工業社製）
[Main ingredients]
・ 3- (Trimethoxysilyl) propyl isocyanate (manufactured by Tokyo Chemical Industry Co., Ltd.)
〔実施例１〕
＜１−｛２−［４，６−ジアミノ−（１，３，５）トリアジン−２−イル］−エチル｝−３−［３−（トリメトキシシリル）プロピル］ウレアの合成＞
温度計を備えた１００ｍＬフラスコに、２，４−ジアミノ−６−（２−アミノエチル）−１，３，５−トリアジン1．５４ｇ（１０．０ｍｍｏｌ）、３−（トリメトキシシリル）プロピルイソシアネート２．０５ｇ（１０．０ｍｍｏｌ）およびＤＭＳＯ５０ｍＬを投入して、反応液を調製し、室温２０℃の下にて２４時間撹拌した。生成した固形物をろ別し、メタノールで洗浄した後、７０℃で乾燥し、白色結晶２．５１ｇ（収率７０％）を得た。
[Example 1]
<Synthesis of 1- {2- [4,6-diamino- (1,3,5) triazin-2-yl] -ethyl} -3- [3- (trimethoxysilyl) propyl] urea>
In a 100 mL flask equipped with a thermometer, 1.54 g (10.0 mmol) of 2,4-diamino-6- (2-aminoethyl) -1,3,5-triazine, 3- (trimethoxysilyl) propyl isocyanate 2 .05 g (10.0 mmol) and DMSO 50 mL were added to prepare a reaction solution, which was stirred at room temperature at 20 ° C. for 24 hours. The produced solid was filtered off, washed with methanol, and then dried at 70 ° C. to obtain 2.51 g of white crystals (yield 70%).
得られた結晶の１Ｈ−ＮＭＲスペクトルデータは、以下のとおりであり、得られた結晶は、化学式（II−１）で示される標題のトリアジン化合物であるものと同定した。
・1H-NMR(d6-DMSO) δ：6.60 (br, 4H), 3.46(s, 9H), 2.94-2.99(m, 2H), 2.81(t, 2H), 2.44(t, 2H), 1.43-1.47(m, 2H), 0.52(dd, 2H).
The 1 H-NMR spectral data of the obtained crystal are as follows, and the obtained crystal was identified as the title triazine compound represented by the chemical formula (II-1).
1 H-NMR (d 6 -DMSO) δ: 6.60 (br, 4H), 3.46 (s, 9H), 2.94-2.99 (m, 2H), 2.81 (t, 2H), 2.44 (t, 2H), 1.43-1.47 (m, 2H), 0.52 (dd, 2H).
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018043035A1 (en) * | 2016-08-30 | 2018-03-08 | リンテック株式会社 | Resin composition, resinous sheet, and semiconductor device |
| CN114350146A (en) * | 2022-01-06 | 2022-04-15 | 宁波群力紧固件制造有限公司 | High-strength bolt material and preparation method thereof |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60123572A (en) * | 1983-12-08 | 1985-07-02 | Shikoku Chem Corp | One-pack epoxy resin ink composition |
| JPS619428A (en) * | 1984-06-23 | 1986-01-17 | Shikoku Chem Corp | Epoxy resin composition |
| JPS61233013A (en) * | 1985-04-08 | 1986-10-17 | Shikoku Chem Corp | Method for curing polyepoxy resin |
| JPH06179662A (en) * | 1992-12-14 | 1994-06-28 | Shikoku Chem Corp | New carbamoyl compound and method for curing epoxy resin using the same compound |
| JPH0710871A (en) * | 1993-06-19 | 1995-01-13 | Shikoku Chem Corp | Diamino-s-triazine compound having imidaziline ring and curing of epoxy resin therewith |
| JPH0710850A (en) * | 1993-06-19 | 1995-01-13 | Shikoku Chem Corp | Diamino-s-triazine compound having carbamoyl group and method for curing epoxy resin with the compound |
| JPH0733766A (en) * | 1993-07-23 | 1995-02-03 | Shikoku Chem Corp | Diamino-s-triazine compound having imidazole ring and method for preventing copper from rusting using the same compound |
| JP2000063365A (en) * | 1998-06-12 | 2000-02-29 | Shikoku Chem Corp | Isocyanuric acid salt of new 2-substituted guanamine compound and flame-retardant resin composition containing isocyanuric acid salt of 2-substituted guanamine compound as active ingredient |
| JP2000154181A (en) * | 1998-06-10 | 2000-06-06 | Shikoku Chem Corp | New 2-substituted guanamine compound and flame retardant resin composition containing 2-substituted guanamine compound as active component |
-
2014
- 2014-08-01 JP JP2014157439A patent/JP6300680B2/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60123572A (en) * | 1983-12-08 | 1985-07-02 | Shikoku Chem Corp | One-pack epoxy resin ink composition |
| JPS619428A (en) * | 1984-06-23 | 1986-01-17 | Shikoku Chem Corp | Epoxy resin composition |
| JPS61233013A (en) * | 1985-04-08 | 1986-10-17 | Shikoku Chem Corp | Method for curing polyepoxy resin |
| JPH06179662A (en) * | 1992-12-14 | 1994-06-28 | Shikoku Chem Corp | New carbamoyl compound and method for curing epoxy resin using the same compound |
| JPH0710871A (en) * | 1993-06-19 | 1995-01-13 | Shikoku Chem Corp | Diamino-s-triazine compound having imidaziline ring and curing of epoxy resin therewith |
| JPH0710850A (en) * | 1993-06-19 | 1995-01-13 | Shikoku Chem Corp | Diamino-s-triazine compound having carbamoyl group and method for curing epoxy resin with the compound |
| JPH0733766A (en) * | 1993-07-23 | 1995-02-03 | Shikoku Chem Corp | Diamino-s-triazine compound having imidazole ring and method for preventing copper from rusting using the same compound |
| JP2000154181A (en) * | 1998-06-10 | 2000-06-06 | Shikoku Chem Corp | New 2-substituted guanamine compound and flame retardant resin composition containing 2-substituted guanamine compound as active component |
| JP2000063365A (en) * | 1998-06-12 | 2000-02-29 | Shikoku Chem Corp | Isocyanuric acid salt of new 2-substituted guanamine compound and flame-retardant resin composition containing isocyanuric acid salt of 2-substituted guanamine compound as active ingredient |
Non-Patent Citations (1)
| Title |
|---|
| 鎌形一夫ら: "２，４−ジアミノ−６−ビニル−ｓ−トリアジン化合物の銀の移行防止効果", 電子通信学会論文誌, vol. J69-C(1), JPN7017004147, 1986, pages pp. 126-130 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018043035A1 (en) * | 2016-08-30 | 2018-03-08 | リンテック株式会社 | Resin composition, resinous sheet, and semiconductor device |
| CN109563352A (en) * | 2016-08-30 | 2019-04-02 | 琳得科株式会社 | Resin combination, resin sheet and semiconductor device |
| JPWO2018043035A1 (en) * | 2016-08-30 | 2019-06-24 | リンテック株式会社 | Resin composition, resin sheet, and semiconductor device |
| CN109563352B (en) * | 2016-08-30 | 2021-10-22 | 琳得科株式会社 | Resin composition, resin sheet, and semiconductor device |
| CN114350146A (en) * | 2022-01-06 | 2022-04-15 | 宁波群力紧固件制造有限公司 | High-strength bolt material and preparation method thereof |
| CN114350146B (en) * | 2022-01-06 | 2024-03-29 | 宁波群力紧固件制造有限公司 | High-strength bolt material and preparation method thereof |
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