TW202346406A - 化合物、硬化性樹脂組合物及硬化物 - Google Patents
化合物、硬化性樹脂組合物及硬化物 Download PDFInfo
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- TW202346406A TW202346406A TW112109120A TW112109120A TW202346406A TW 202346406 A TW202346406 A TW 202346406A TW 112109120 A TW112109120 A TW 112109120A TW 112109120 A TW112109120 A TW 112109120A TW 202346406 A TW202346406 A TW 202346406A
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
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- 238000002715 modification method Methods 0.000 description 1
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- 229910052863 mullite Inorganic materials 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
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- HUWUUMUEMQWJKZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-benzylpropane-1,3-diamine Chemical compound NCCCN(CCCN)CC1=CC=CC=C1 HUWUUMUEMQWJKZ-UHFFFAOYSA-N 0.000 description 1
- CMDGBXZMCXCQFG-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-butylpropane-1,3-diamine Chemical compound CCCCN(CCCN)CCCN CMDGBXZMCXCQFG-UHFFFAOYSA-N 0.000 description 1
- BQUQUASUHNZZLS-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCN(CCCN)C1CCCCC1 BQUQUASUHNZZLS-UHFFFAOYSA-N 0.000 description 1
- ZKKMLXOYLORBLV-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-ethylpropane-1,3-diamine Chemical compound NCCCN(CC)CCCN ZKKMLXOYLORBLV-UHFFFAOYSA-N 0.000 description 1
- LUZCQJHUWNIZNZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-pentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCN LUZCQJHUWNIZNZ-UHFFFAOYSA-N 0.000 description 1
- CSIOOUSJMRKIAQ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-propylpropane-1,3-diamine Chemical compound NCCCN(CCC)CCCN CSIOOUSJMRKIAQ-UHFFFAOYSA-N 0.000 description 1
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-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
- NGRXSVVLBWDAHG-UHFFFAOYSA-N n,n-bis(propan-2-ylamino)ethanamine Chemical compound CC(C)NN(CC)NC(C)C NGRXSVVLBWDAHG-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
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- WLNSKTSWPYTNLY-UHFFFAOYSA-N n-ethyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCNCCN(C)C WLNSKTSWPYTNLY-UHFFFAOYSA-N 0.000 description 1
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical group CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical group CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- HATIEXJZXOLRAO-UHFFFAOYSA-N octanedihydrazide Chemical compound NNC(=O)CCCCCCC(=O)NN HATIEXJZXOLRAO-UHFFFAOYSA-N 0.000 description 1
- KEJVUXJFDYXFSK-UHFFFAOYSA-N octyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCC)C1=CC=CC=C1 KEJVUXJFDYXFSK-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052609 olivine Inorganic materials 0.000 description 1
- 239000010450 olivine Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical group NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-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
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Abstract
本發明係一種化合物,其由下述式(1)表示。
式中,R
1表示氫原子或甲基,R
2~R
5分別獨立地表示氫原子、碳數1~10之烷基、碳數1~10之烷氧基、碳數1~10之烷醯氧基、碳數1~10之烷氧羰基、碳數1~10之烷醯胺基、鹵素原子、羥基、硝基或腈基,A
1表示碳數1~20之伸烷基,A
2表示伸丙基或伸異丙基。
Description
本發明係關於一種化合物及硬化性樹脂組合物。詳細而言,本發明係關於一種具有環氧基之醯亞胺化合物,又,係關於一種含有上述化合物、環氧樹脂及硬化劑之硬化性樹脂組合物。
環氧樹脂作為塗料、接著劑、各種成形材料等之成分廣泛用於工業中。
於將環氧樹脂用於上述用途之情形時,通常與硬化劑組合使用,作為該硬化劑,已知有酸酐系硬化劑、胺系硬化劑、酚系硬化劑等各種硬化劑。
上述硬化劑根據用途區分使用,例如咪唑系硬化劑與加成聚合型硬化劑不同,為陰離子聚合型硬化劑,故而少量添加即可硬化,又,揮發性低且毒性低之性質亦有用,因此可適宜地用於電氣/電子零件。
然而,於單獨使用咪唑系硬化劑之情形時,難以取得硬化性與儲存穩定性之平衡。為提高儲存穩定性,例如於專利文獻1中提出將咪唑化合物與環氧樹脂之反應物用於環氧硬化系統,於專利文獻2中提出一種包含改性咪唑、改性胺及酚化合物之環氧樹脂用硬化劑組合物。
另一方面,即便於使用該等各種改性咪唑之情形時,硬化性樹脂組合物之儲存穩定性亦仍未能令人滿意。
[先前技術文獻]
[專利文獻]
專利文獻1:美國專利第4066625號說明書
專利文獻2:日本專利特開2007-297493號公報
[發明所欲解決之問題]
因此,本發明所欲解決之問題在於提供一種可獲得儲存穩定性優異之硬化性樹脂組合物之材料。
[解決問題之技術手段]
本發明者等人進行了努力研究,結果發現,藉由硫醚鍵將醯亞胺部位與環氧部位鍵結而獲得之特定化合物可提高儲存穩定性,從而完成了本發明。
即,本發明係一種化合物,其由下述式(1)表示。
[化1]
式中,R
1表示氫原子或甲基,R
2、R
3、R
4及R
5(以下亦記為「R
2~R
5」)分別獨立地表示氫原子、碳數1~10之烷基、碳數1~10之烷氧基、碳數1~10之烷醯氧基、碳數1~10之烷氧羰基、碳數1~10之烷醯胺基、碳數1~10之醯胺基、鹵素原子、羥基、硝基或腈基,A
1表示碳數1~20之伸烷基,A
2表示伸丙基或伸異丙基。
又,本發明提供一種硬化性樹脂組合物,其含有上述化合物作為(A)成分,含有環氧樹脂作為(B)成分,及含有硬化劑作為(C)成分。
又,本發明提供一種上述硬化性樹脂組合物之硬化物。
[發明之效果]
根據本發明,可提供一種硬化物之熱穩定性優異且儲存穩定性優異之硬化性樹脂組合物。本發明之硬化性樹脂組合物可適宜地用作一液硬化型之硬化性樹脂組合物。
以下,對本發明之化合物進行說明。
本發明之化合物為下述式(1)所表示之化合物。
[化2]
上述式(1)中,R
1表示氫原子或甲基,R
2~R
5分別獨立地表示氫原子、碳數1~10之烷基、碳數1~10之烷氧基、碳數1~10之烷醯氧基、碳數1~10之烷氧羰基、碳數1~10之烷醯胺基、碳數1~10之醯胺基、鹵素原子、羥基、硝基或腈基,A
1表示碳數1~20之伸烷基,A
2表示伸丙基或伸異丙基。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之烷基,例如可例舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、2-乙基己基、壬基、異壬基、癸基及異癸基等。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之烷氧基,例如可例舉:甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基及癸氧基等。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之烷醯氧基,例如可例舉:甲醯氧基、乙醯氧基、丙醯氧基、丁醯氧基、庚醯氧基、辛醯氧基、壬醯氧基、癸醯氧基等。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之烷氧羰基,例如可例舉:甲氧羰基、乙氧羰基、丙氧羰基、丁氧羰基、戊氧羰基、己氧羰基、庚氧羰基、辛氧羰基、壬氧羧基、癸氧羰基等。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之烷醯胺基,例如可例舉:甲醯胺基、乙醯胺基、丙醯胺基、丁醯胺基、戊醯胺基、己醯胺基、庚醯胺基、辛醯胺基、壬醯胺基、癸醯胺基等。
作為上述式(1)中之R
2~R
5所表示之碳數1~10之醯胺基,例如可例舉:甲醯胺基、乙醯胺基、正丙醯胺基、異丙醯胺基、第三丁醯胺基、N,N-二甲醯胺基、N,N-二乙醯胺基、N,N-二正丙醯胺基、N,N-二異丙醯胺基、N,N-二第三丁醯胺基。
作為上述式(1)中之R
2~R
5所表示之鹵素原子,例如可例舉氟、氯、溴及碘等。
作為上述式(1)中之A
2所表示之碳數1~20之伸烷基,例如可例舉:亞甲基、伸乙基、伸丙基、伸異丙基、伸丁基、伸戊基、伸己基、伸庚基、伸辛基、伸壬基、癸烯基、十一碳烯基、十二碳烯基、十三碳烯基、十四碳烯基、十五碳烯基、十六碳烯基、十七碳烯基、十八碳烯基、十九碳烯基、二十碳烯基等。
上述式(1)所表示之化合物之中,自可容易地製造之觀點出發,較佳為R
2~R
5分別獨立地為氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基之化合物,特佳為R
3或R
4為氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基之化合物。尤其是,特佳為R
2、R
4及R
5為氫原子且R
3為氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基之化合物。
又,較佳為A
1為碳數1~4之伸烷基之化合物,更佳為A
1為碳數1~3之伸烷基之化合物,特佳為A
1為碳數1~2之伸烷基之化合物。
進而,自容易獲取原料之觀點出發,R
1較佳為氫原子。
上述式(1)所表示之化合物中之較佳化合物為下述式(1A)所表示之化合物及/或(1B)所表示之化合物,亦可為該等之混合物。於其為混合物之情形時,下述式(1A)所表示之化合物及/或(1B)所表示之化合物之質量比(1A):(1B)可為1:0.01~100。
[化3]
上述式(1A)中,R
1a表示氫原子或甲基,R
6分別獨立地表示氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基。
[化4]
上述式(1B)中,R
1b表示氫原子或甲基,R
7分別獨立地表示氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基。
尤其是,上述式(1A)所表示之化合物及上述式(1B)所表示之化合物中,關於R
1a及R
1b,作為較佳基,可例舉作為上述R
1而於上文所述之基。尤其是,作為R
3、R
6及R
7,較佳為氫原子、甲基、鹵素原子、硝基。於使用式(1A)所表示之化合物及上述式(1B)所表示之化合物作為上述式(1)所表示之化合物中之較佳化合物之情形時,式(1A)之R
6及式(1B)之R
7可相同,亦可不同。又,於上述情形時,式(1A)之R
1a及式(1B)之R
1b可相同,亦可不同。
以下示出特別適宜之化合物。
[化5]
[化6]
[化7]
[化8]
[化9]
[化10]
[化11]
[化12]
[化13]
[化14]
[化15]
[化16]
[化17]
[化18]
本發明之式(1)所表示之化合物之製造方法並無特別限定,例如可根據下述方案製造。
此處,硫醇化合物(a)與烯丙基縮水甘油醚及/或烯丙基β-甲基縮水甘油醚(以下有時亦統稱為「烯丙基縮水甘油醚類」)(b)之反應係藉由於硫醇化合物(a)與烯丙基縮水甘油醚類(b)之不飽和鍵之間發生之硫醇-烯反應而進行者。
[化19]
上述式中之R
1~R
5、A
1及A
2與上述式(1)中之各符號相同。
上述反應中使用之硫醇化合物(a)為公知化合物,其製造方法並無限制,例如為藉由使可具有取代基之鄰苯二甲酸酐與胺基烷硫醇於溶劑中反應而容易地獲得者。作為胺基烷硫醇,可例舉:胺基甲硫醇、2-胺基乙硫醇、3-胺基-1-丙硫醇、4-胺基-1-丁硫醇、5-胺基-1-戊硫醇、6-胺基-1-己硫醇等。
作為於上述可具有取代基之鄰苯二甲酸酐與胺基烷硫醇之反應中使用之溶劑,並無特別限制,例如可例舉:戊烷、己烷、庚烷、環己烷等飽和烴類;苯、甲苯、二甲苯、乙苯等芳香族烴類;二氯甲烷、氯仿、四氯化碳、二氯乙烷、氯苯、二氯苯等鹵化烴類;二乙醚、二異丙醚、1,2-二甲氧基乙烷、雙(2-甲氧基乙基)醚、1,2-雙(2-甲氧基乙氧基)乙烷、雙[2-(2-甲氧基乙氧基)乙基]醚、四氫呋喃、1,3-二㗁烷、1,4-二㗁烷、苯甲醚等醚類;苯酚、鄰氯酚、間氯酚、對氯酚、鄰甲酚、間甲酚、對甲酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚等酚類;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二乙基乙醯胺、N,N-二甲基甲氧基乙醯胺、六甲基磷醯胺等醯胺類;N-甲基-2-吡咯啶酮、N-甲基己內醯胺等內醯胺類;二甲基亞碸、二苯基亞碸、二甲基碸、二苯基碸、環丁碸等含硫溶劑類、1,3-二甲基-2-咪唑啶酮等。該等有機溶劑可單獨使用,亦可將2種以上混合而使用。
有機溶劑之使用量並無特別限制,相對於可具有取代基之鄰苯二甲酸酐與胺基烷硫醇之合計1質量份,為0.1~10000質量份,較佳為1~100質量份。反應有機溶劑較佳為溶解原料而形成溶液,但亦可於漿料狀態下進行反應。
上述可具有取代基之鄰苯二甲酸酐與胺基烷硫醇之反應可於通常用於醯亞胺化之有機鹼觸媒或酸觸媒之存在下進行。
作為上述有機鹼觸媒,例如可例舉:三乙胺、三丁胺、三戊胺、N,N-二甲基苯胺、N,N-二乙基苯胺、吡啶、α-甲基吡啶、β-甲基吡啶、γ-甲基吡啶、2,4-二甲基吡啶、2,6-二甲基吡啶、喹啉及異喹啉等,但較佳為吡啶及γ-甲基吡啶。該等有機鹼觸媒可單獨使用,亦可將2種以上組合而使用。
作為上述酸觸媒,例如可例舉:鹽酸、溴化氫、碘化氫、硫酸、無水硫酸、硝酸、磷酸、亞磷酸、磷鎢酸、磷鉬酸等無機酸類;甲磺酸、乙磺酸、三氟甲磺酸、苯磺酸、對甲苯磺酸等磺酸類;乙酸、草酸等羧酸類;氯乙酸、二氯乙酸、三氯乙酸、氟乙酸、二氟乙酸、三氟乙酸等鹵化羧酸類;二氧化矽、氧化鋁、活性白土等固體酸類;陽離子型離子交換樹脂等。尤其是,較適宜為硫酸、磷酸及對甲苯磺酸。該等酸觸媒可單獨使用,亦可將2種以上組合而使用。又,該等酸觸媒亦可為與二胺化合物之鹽。
上述觸媒之使用量並無特別限制,只要反應速度實質上提高即可,相對於可具有取代基之鄰苯二甲酸酐及胺基烷硫醇之合計1莫耳,為0.001~10莫耳,較佳為0.005~5莫耳,進而較佳為0.01~1莫耳。
上述可具有取代基之鄰苯二甲酸酐與胺基烷硫醇之反應時間根據所使用之原料之種類、溶劑之種類、觸媒之種類、及反應溫度等而不同,但作為標準,為1~24小時,通常為數個小時。直接進行熱醯亞胺化時,作為標準,進行反應直至蒸餾出之水大致達到理論量。
上述酸酐與胺基烷硫醇之反應之壓力並無特別限制,通常為大氣壓即可。反應氛圍並無特別限制,通常為空氣、氮氣、氦氣、氖氣或氬氣氛圍,較佳為作為惰性氣體之氮氣及氬氣氛圍。
上述反應結束後,將式(a)所表示之硫醇化合物進行單離之方法並無特別限定,於目標物自反應溶劑中析出之情形時,藉由過濾或離心分離進行單離即可。另一方面,於目標物溶解於溶劑中之情形時,於減壓下蒸餾去除溶劑、於反應混合物中添加適當之不良溶劑、或將反應混合物排出至不良溶劑等使目標物析出,藉由過濾或離心分離進行單離即可。
於需要進一步精製單離出之式(a)所表示之硫醇化合物之情形時,採用已知為常規法之方法精製即可,作為該方法,可例舉:蒸餾精製法、再結晶法、管柱層析法、污泥處理及活性碳處理等。
又,烯丙基縮水甘油醚及/或烯丙基β-甲基縮水甘油醚(b)可藉由使烯丙醇與表氯醇及/或β-甲基表氯醇於觸媒之存在下視需要於溶劑中於20~120℃反應數個小時~十幾個小時而獲得。
作為上述反應中使用之觸媒,例如可例舉:鹼性化合物、有機磷系化合物、三級胺、及路易斯酸等。作為鹼性化合物,例如可例舉:氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化鈣、氫氧化鎂等鹼金屬或鹼土類金屬之氫氧化物。作為有機磷系化合物,例如可例舉:三環己基膦、三丁基膦、三辛基膦、環己基二苯基膦、二環己基苯基膦、丁基二苯基膦、二丁基苯基膦、辛基二苯基膦、二辛基苯基膦、三苯基膦等。作為三級胺,可例舉:三甲胺、三乙胺、三丙胺、三丁胺、二氮雜雙環十一烯、二氮雜雙環壬烯、1-甲基咪唑等。作為路易斯酸,例如可例舉:三氟化硼、氯化鋁、甲基二氯鋁、二甲基氯鋁、三甲基鋁、氯化鎂、溴化鎂、四氯化鈦、雙三氟甲磺酸二氯鈦、雙三氟甲磺酸雙環戊二烯基鈦、雙氟磺酸二氯鈦、四氯化錫、雙三氟甲磺酸錫(II)等。上述觸媒可單獨使用1種,亦可將2種以上組合而使用。
作為上述反應中使用之溶劑,例如可例舉:甲基溶纖劑、乙基溶纖劑、異丙基溶纖劑、丁基溶纖劑、丙二醇單甲醚、二乙二醇單甲醚、三乙二醇單甲醚、聚乙二醇單甲醚、乙二醇二甲醚、二乙二醇二甲醚、三乙二醇二甲醚及聚乙二醇二甲醚等二醇醚溶劑;乙酸乙酯、乙酸丁酯、乙酸戊酯、乳酸乙酯及苯甲酸甲酯等酯系溶劑;直鏈己烷、直鏈庚烷及直鏈辛烷等脂肪族烴系溶劑;環己烷及乙基環己烷等脂環式烴系溶劑;丙酮、甲基乙基酮及甲基異丁基酮等酮系溶劑;苯、甲苯及二甲苯等芳香族烴溶劑;以及石油系溶劑等。上述溶劑可單獨使用1種,亦可將2種以上組合而使用。
上述硫醇化合物(a)與烯丙基縮水甘油醚類(b)之反應係可藉由於溶劑中使用觸媒於15~100℃反應數個小時~數天而製造。
再者,上述反應中,由於難以控制烯丙基之α位及β位上之反應,因此以混合物之形式獲得A
2為直鏈伸丙基之化合物與A
2為伸異丙基之化合物,但該等可不單離而使用。
作為可於上述反應中使用之觸媒,可使用公知之熱自由基起始劑,例如可例舉:2,2'-偶氮二異丁腈、2,2'-偶氮雙(異丁酸甲酯)、2,2'-偶氮雙-2,4-二甲基戊腈、1,1'-偶氮雙(1-乙醯氧基-1-苯乙烷)等偶氮系化合物;過氧化苯甲醯、過氧化二第三丁基苯甲醯、過氧化特戊酸第三丁酯及過氧化二碳酸二(4-第三丁基環己基)酯等過氧化物;過硫酸銨、過硫酸鈉及過硫酸鉀等過硫酸鹽等。
上述觸媒之使用量並無特別限制,只要反應速度實質上提高即可,相對於硫醇化合物(a)及烯丙基縮水甘油醚類(b)之合計1莫耳,為0.001~10莫耳,較佳為0.005~5莫耳,進而較佳為0.01~1莫耳。
上述硫醇化合物(a)與上述烯丙基縮水甘油醚類(b)之反應中之溶劑之使用較為任意,作為所使用之溶劑,並無特別限制,例如可例舉:戊烷、己烷、庚烷、環己烷等飽和烴類;苯、甲苯、二甲苯、乙苯等芳香族烴類;二氯甲烷、氯仿、四氯化碳、二氯乙烷、氯苯、二氯苯等鹵化烴類;二乙醚、二異丙醚、1,2-二甲氧基乙烷、雙(2-甲氧基乙基)醚、1,2-雙(2-甲氧基乙氧基)乙烷、雙[2-(2-甲氧基乙氧基)乙基]醚、四氫呋喃、1,3-二㗁烷、1,4-二㗁烷、苯甲醚等醚類;苯酚、鄰氯酚、間氯酚、對氯酚、鄰甲酚、間甲酚、對甲酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚等酚類;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二乙基乙醯胺、N,N-二甲基甲氧基乙醯胺、六甲基磷醯胺等醯胺類;N-甲基-2-吡咯啶酮、N-甲基己內醯胺等內醯胺類;二甲基亞碸、二苯基亞碸、二甲基碸、二苯基碸、環丁碸等含硫溶劑類、1,3-二甲基-2-咪唑啶酮等。該等有機溶劑可單獨使用,亦可將2種以上混合而使用。
上述溶劑之使用量並無特別限制,相對於硫醇化合物(a)與烯丙基縮水甘油醚類(b)之合計1質量份,為0.1~10000質量份,較佳為1~100質量份。溶劑較佳為溶解原料而形成溶液,但亦可於漿料狀態下進行反應。
反應時間根據所使用之原料之種類、溶劑之種類、觸媒之種類、及反應溫度等而不同,但作為標準,為1~24小時,通常為數個小時。
上述反應中之反應壓力並無特別限制,通常為大氣壓即可。反應氛圍並無特別限制,通常為空氣、氮氣、氦氣、氖氣或氬氣氛圍,較佳為作為惰性氣體之氮氣及氬氣氛圍。
上述反應結束後,將式(1)所表示之化合物進行單離之方法並無特別限定,於目標物自溶劑中析出之情形時,藉由過濾或離心分離進行單離即可。另一方面,於目標物溶解於溶劑中之情形時,於減壓下蒸餾去除溶劑、於反應混合物中添加適當之不良溶劑、或將反應混合物排出至不良溶劑等使目標物析出,藉由過濾或離心分離進行單離即可。
於需要進一步精製單離出之式(1)所表示之化合物之情形時,採用已知為常規法之方法精製即可,作為該方法,可例舉:蒸餾精製法、再結晶法、管柱層析法、污泥處理及活性碳處理等。
其次,對本發明之硬化性樹脂組合物進行說明。
本發明之硬化性樹脂組合物含有上述式(1)所表示之化合物作為(A)成分,含有環氧樹脂作為(B)成分,及含有硬化劑作為(C)成分。
本發明中使用之作為(B)成分之環氧樹脂為分子中具有至少2個環氧基者即可,可對分子結構、分子量等並無特別限制地使用。
作為上述環氧樹脂,可例舉:對苯二酚、間苯二酚、鄰苯二酚及間苯三酚等單核多酚化合物之聚縮水甘油醚化物;二羥基萘、聯苯酚、亞甲基二苯酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基二苯酚、亞異丙基二苯酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代二苯酚、磺基二苯酚、氧基二苯酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆及萜酚等多核多酚化合物之聚縮水甘油醚化物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫甘醇、二環戊二烯二甲醇、2,2-雙(4-羥基環己基)丙烷(氫化雙酚A)、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇及雙酚A-環氧烷加成物等多元醇化合物之聚縮水甘油醚化物;馬來酸、富馬酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、均苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸及內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯化物及甲基丙烯酸縮水甘油酯之均聚物或共聚物;N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)苯胺及N,N,N',N'-四(2,3-環氧丙基)-4,4-二胺基二苯甲烷等具有縮水甘油基胺基之環氧化合物;乙烯基環己烯二環氧化物、環戊二烯二環氧化物、3,4-環氧環己烷羧酸3,4-環氧環己基甲酯、6-甲基環己烷羧酸3,4-環氧-6-甲基環己基甲酯及己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等環狀烯烴化合物之環氧化物;環氧化聚丁二烯及環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物;異氰尿酸三縮水甘油酯等雜環化合物。又,該等環氧樹脂可以藉由末端異氰酸酯之預聚物而內部交聯之形式使用,又,亦可以藉由多元之活性氫化合物(多酚、聚胺、含羰基化合物、聚磷酸酯等)而高分子量化之形式使用。環氧樹脂可單獨使用,亦可併用2種以上。
本發明中使用之作為(C)成分之硬化劑,例如可例舉:酸酐系硬化劑、酚系硬化劑、胺系硬化劑、聚硫醇系硬化劑及咪唑系硬化劑等。
作為上述酸酐系硬化劑,例如可例舉:雙環庚烯二甲酸酐、鄰苯二甲酸酐、馬來酸酐、甲基雙環庚烯二甲酸酐、琥珀酸酐、四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐-馬來酸酐加成物、二苯甲酮四羧酸二酐、偏苯三甲酸酐、均苯四甲酸二酐及氫化甲基耐地酸酐等。
作為上述酚系硬化劑,例如可例舉:苯酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、芳香族烴甲醛樹脂改性酚樹脂、二環戊二烯苯酚加成型樹脂、苯酚芳烷基樹脂(ZYLOCK樹脂)、萘酚芳烷基樹脂、三酚基甲烷樹脂、四酚基乙烷樹脂、萘酚酚醛清漆樹脂、萘酚-苯酚共縮合酚醛清漆樹脂、萘酚-甲酚共縮合酚醛清漆樹脂、聯苯改性酚樹脂(酚核藉由雙亞甲基連結之多酚化合物)、聯苯改性萘酚樹脂(酚核藉由雙亞甲基連結之多元萘酚化合物)、胺基三𠯤改性酚樹脂(分子結構中具有酚骨架、三𠯤環及一級胺基之化合物)、及含烷氧基芳香環改性酚醛清漆樹脂(酚核及含烷氧基芳香環藉由甲醛連結之多酚化合物)等多酚化合物。
作為上述胺系硬化劑,例如可例舉:乙二胺、1,2-丙二胺、1,3-丙二胺、1,3-丁二胺、1,4-丁二胺、六亞甲基二胺及間苯二甲胺等伸烷基二胺類;二伸乙基三胺、三伸乙基三胺及四伸乙基五胺等聚烷基聚胺類;1,4-環己二胺、1,3-環己二胺、1,3-二胺基甲基環己烷、1,2-環己二胺、1,4-二胺基-3,6-二乙基環己烷、4,4'-二胺基二環己基甲烷、1,3-雙(胺基甲基)環己烷、1,4-雙(胺基甲基)環己烷、4,4'-二胺基二環己基丙烷、雙(4-胺基環己基)碸、4,4'-二胺基二環己基醚、2,2'-二甲基-4,4'-二胺基二環己基甲烷、異佛爾酮二胺及降𦯉烯二胺等脂環式聚胺類;二胺基二苯甲烷、二胺基二苯基碸、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二胺基苯、1-甲基-3,5-二乙基-2,6-二胺基苯、1,3,5-三乙基-2,6-二胺基苯、3,3'-二乙基-4,4'-二胺基二苯甲烷及3,5,3',5'-四甲基-4,4'-二胺基二苯甲烷等芳香族聚胺類;N,N-二甲胺基乙基胺、N,N-二乙胺基乙基胺、N,N-二異丙胺基乙基胺、N,N-二烯丙基胺基乙基胺、N,N-苄基甲胺基乙基胺、N,N-二苄基胺基乙基胺、N,N-環己基甲胺基乙基胺、N,N-二環己基胺基乙基胺、N-(2-胺基乙基)吡咯啶、N-(2-胺基乙基)哌啶、N-(2-胺基乙基)𠰌啉、N-(2-胺基乙基)哌𠯤、N-(2-胺基乙基)-N'-甲基哌𠯤、N,N-二甲胺基丙基胺、N,N-二乙胺基丙基胺、N,N-二異丙基胺基丙基胺、N,N-二烯丙基胺基丙基胺、N,N-苄基甲胺基丙基胺、N,N-二苄基胺基丙基胺、N,N-環己基甲胺基丙基胺、N,N-二環己基胺基丙基胺、N-(3-胺基丙基)吡咯啶、N-(3-胺基丙基)哌啶、N-(3-胺基丙基)𠰌啉、N-(3-胺基丙基)哌𠯤、N-(3-胺基丙基)-N'-甲基哌啶、4-(N,N-二甲基胺基)苄胺、4-(N,N-二乙基胺基)苄胺、4-(N,N-二異丙基胺基)苄胺、N,N,-二甲基異佛爾酮二胺、N,N-二甲基二胺基環己烷、N,N,N'-三甲基乙二胺、N'-乙基-N,N-二甲基乙二胺、N,N,N'-三乙基乙二胺、N'-乙基-N,N-二甲基丙二胺、N'-乙基-N,N-二苄基胺基丙基胺;N,N-(雙胺基丙基)-N-甲基胺、N,N-雙胺基丙基乙基胺、N,N-雙胺基丙基丙基胺、N,N-雙胺基丙基丁基胺、N,N-雙胺基丙基戊基胺、N,N-雙胺基丙基己基胺、N,N-雙胺基丙基-2-乙基己基胺、N,N-雙胺基丙基環己基胺、N,N-雙胺基丙基苄胺、N,N-雙胺基丙基烯丙基胺、雙[3-(N,N-二甲基胺基丙基)]胺、雙[3-(N,N-二乙基胺基丙基)]胺、雙[3-(N,N-二異丙基胺基丙基)]胺、雙[3-(N,N-二丁基胺基丙基)]胺;乙二醯肼、丙二醯肼、琥珀酸二醯肼、戊二酸二醯肼、己二酸二醯肼、辛二酸二醯肼、壬二酸二醯肼、癸二酸二醯肼及鄰苯二甲酸二醯肼等二元酸二醯肼;雙氰胺、苯并胍胺及乙醯胍胺等胍化合物;三聚氰胺等。
又,亦可使用上述胺類改性而成之改性胺系硬化劑。作為改性方法,可例舉:與羧酸之脫水縮合、與環氧樹脂之加成反應、與異氰酸酯之加成反應、麥可加成反應、曼尼希反應、與脲之縮合反應、及與酮之縮合反應等。
作為可用於上述胺類之改性之羧酸,例如可例舉:馬來酸、富馬酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、均苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸及內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸等。
作為可用於上述胺類之改性之環氧化合物,例如可例舉作為上述(B)成分之環氧樹脂而例示之環氧化合物。
作為可用於上述胺類之改性之異氰酸酯化合物,例如可例舉:2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯、苯二異氰酸酯、苯二甲基二異氰酸酯、四甲基苯二甲基二異氰酸酯、1,5-萘二異氰酸酯、1,5-四氫萘二異氰酸酯、3,3'-二甲基二苯基-4,4'-二異氰酸酯及二甲氧基苯胺二異氰酸酯等芳香族二異氰酸酯;異佛爾酮二異氰酸酯、二環己基甲烷-4,4'-二異氰酸酯、反式-1,4-環己基二異氰酸酯及降𦯉烯二異氰酸酯等脂環式二異氰酸酯;四亞甲基二異氰酸酯、1,6-六亞甲基二異氰酸酯、2,2,4及/或(2,4,4)-三甲基六亞甲基二異氰酸酯及離胺酸二異氰酸酯等脂肪族二異氰酸酯;上述例示之二異氰酸酯之異氰尿酸酯三聚物、縮二脲三聚物及三羥甲基丙烷加成化合物等;三苯甲烷三異氰酸酯、1-甲基苯-2,4,6-三異氰酸酯及二甲基三苯甲烷四異氰酸酯等。進而,該等異氰酸酯化合物亦可以碳二醯亞胺改性、異氰尿酸酯改性、縮二脲改性等改性物之形式使用,亦可以藉由各種封端劑封端而成之封端異氰酸酯之形式使用。
作為上述聚硫醇系硬化劑,例如可例舉:季戊四醇四(3-巰基丙酸酯)、季戊四醇四(巰基乙酸酯)、二季戊四醇六(3-巰基丙酸酯)、二季戊四醇六(3-巰基丁酸酯)、1,3,4,6-四(2-巰基乙基)-1,3,4,6-四氮雜八氫并環戊二烯-2,5-二酮、1,3,5-三(3-巰基丙基)-1,3,5-三𠯤-2,4,6(1H,3H,5H)-三酮、4-巰基甲基-1,8-二巰基-3,6-二硫雜辛烷、4,8-、4,7-或5,7-二巰基甲基-1,11-二巰基-3,6,9-三硫雜十一烷、及1,3,4,6-四(2-巰基乙基)甘脲等。
作為上述咪唑系硬化劑,例如可例舉:2-甲基咪唑、2-乙基-4-甲基咪唑、2-異丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、2-胺基丙基咪唑、1-苯基甲基-2-咪唑、1-苯基甲基-2-乙基-4-甲基咪唑、1-苯基甲基-2-苯基咪唑、1-丁氧基羰基乙基-2-甲基咪唑、1-丁氧基羰基乙基-2-乙基-4-甲基咪唑、1-丁氧基羰基乙基-2-苯基咪唑、1-(2-乙基己基)羰基乙基-2-甲基咪唑、1-(2-乙基己基)羰基乙基-2-乙基-4-甲基咪唑、1-(2-乙基己基)羰基乙基-2-苯基咪唑、1-辛氧基羰基乙基-2-甲基咪唑、1-辛氧基羰基乙基-2-乙基-4-甲基咪唑、1-辛氧基羰基乙基-2-苯基咪唑、己二醇-雙(2-甲基咪唑基乙酸)酯、己二醇-雙(2-乙基-4-甲基咪唑基乙酸)酯、己二醇-雙(2-苯基咪唑基乙酸)酯、癸二醇-雙(2-甲基咪唑基乙酸)酯、癸二醇-雙(2-乙基-4-甲基咪唑基乙酸)酯、癸二醇-雙(2-苯基咪唑基乙酸)酯、三環戊烷二甲醇-雙(2-甲基咪唑基乙酸)酯、三環戊烷二甲醇-雙(2-乙基-4-甲基咪唑基乙酸)酯、三環戊烷二甲醇-雙(2-苯基咪唑基乙酸)酯、1-(2-羥基萘基甲基)-2-甲基咪唑、1-(2-羥基萘基甲基)-2-乙基-4-甲基咪唑、1-(2-羥基萘基甲基)-2-苯基咪唑及咪唑矽烷(例如,四國化成工業製造;2MUSIZ)等。該等亦可以與偏苯三甲酸、異三聚氰酸及硼等之鹽之形式使用。又,可與上述胺系硬化劑同樣地進行環氧改性後使用。
作為可用作(C)成分之硬化劑之市售品,例如可例舉:ADEKA HARDENER EH-3636AS、ADEKA HARDENER EH-4351S(ADEKA製造;雙氰胺型潛在性硬化劑)、ADEKA HARDENER EH-5011S、ADEKA HARDENER EH-5046S(ADEKA製造;咪唑型潛在性硬化劑)、ADEKA HARDENER EH-4357S、ADEKA HARDENER EH-5057P、ADEKA HARDENER EH-5057PK(ADEKA製造;聚胺型潛在性硬化劑)、Amicure PN-23、Amicure PN-40(Ajinomoto Fine-Techno製造;胺加成物系潛在性硬化劑)、Amicure VDH(Ajinomoto Fine-Techno製造;醯肼系潛在性硬化劑)、Fujicure FXR-1020(T&K TOKA製造;潛在性硬化劑)、Curezol (四國化成工業製造;咪唑系硬化劑)、TS-G(四國化成工業製造;聚硫醇系硬化劑)、DPMP、PEMP(SC有機化學製造;聚硫醇系硬化劑)及PETG(澱化學製造;聚硫醇系硬化劑)等。
硬化劑可單獨使用,亦可併用2種以上。
本發明中使用之(C)成分之硬化劑中,較佳為咪唑系硬化劑,尤其是2-甲基咪唑、2-乙基-4-甲基咪唑等由於較少量之使用即可促成硬化且可獲得與作為(A)成分之式(1)所表示之化合物之協同效應,故而較佳。
本發明之作為(C)成分之硬化劑之調配量並無特別限定,相對於作為(B)成分之環氧樹脂100質量份,較佳為0.01~100質量份,更佳為1~70質量份,進而較佳為1~50質量份,特佳為3~30質量份。
本發明中,視需要可併用上述硬化劑與公知之環氧樹脂硬化促進劑。作為硬化促進劑,例如可例舉:三苯基膦等膦類;溴化四苯基鏻等鏻鹽;二甲苄胺及2,4,6-三(二甲胺甲基)苯酚等胺類;三甲基氯化銨等四級銨鹽類;3-(對氯苯基)-1,1-二甲脲、3-(3,4-二氯苯基)-1,1-二甲脲、3-苯基-1,1-二甲脲、異佛爾酮二異氰酸酯-二甲脲、及甲苯二異氰酸酯-二甲脲等脲類;三氟化硼與胺類之錯合物、及三氟化硼與醚化合物之錯合物等。該等硬化促進劑可單獨使用,亦可併用2種以上。環氧樹脂硬化促進劑之含量並無特別限制,可根據硬化性樹脂組合物之用途而適當設定。
本發明之硬化性樹脂組合物含有上述式(1)所表示之化合物作為(A)成分,特佳為含有上述式(1A)及/或(1B)所表示之化合物之至少1種作為(A)成分,尤佳為含有上述式(1A-1)、(1B-1)、(1A-2)、(1B-2)、(1A-3)、(1B-3)、(1A-4)或(1B-4)所表示之化合物之至少一種作為(A)成分,其原因在於可獲得熱穩定性及儲存穩定性優異之硬化性樹脂組合物,最佳為含有(1A-1)或(1B-1)所表示之化合物之至少一種作為(A)成分。
相對於(C)成分100質量份,(A)成分之含量較佳為1~2000質量份,更佳為10~1000質量份,進而較佳為30~1000質量份。若(A)成分之含量為1質量份以上,則可獲得硬化性樹脂組合物之穩定性賦予效果,若為2000質量份以下,則可獲得充分之硬化性。
硬化性樹脂組合物中,相對於組合物中之溶劑及填充劑以外之成分之合計量,(A)成分之含量與(B)成分之含量之合計量較適宜為5質量%以上,更適宜為10質量%以上,亦存在20質量%以上之情形。
本發明之硬化性樹脂組合物可含有填充劑。
作為上述填充劑,例如可例舉:熔融二氧化矽及結晶二氧化矽等二氧化矽;氫氧化鎂、氫氧化鋁、鉬酸鋅、碳酸鈣、碳酸矽、矽酸鈣、鈦酸鉀、氧化鈹、氧化鋯、鋯英石、橄欖石、塊滑石、尖晶石、莫來石及二氧化鈦等粉體、以及將該等球形化而獲得之珠粒、玻璃纖維、紙漿纖維、合成纖維及陶瓷纖維等纖維等。
本發明之硬化性樹脂組合物可含有各種溶劑。
作為上述有機溶劑,例如可例舉:四氫呋喃、1,2-二甲氧基乙烷及1,2-二乙氧基乙烷等醚類;異丁醇、正丁醇、異丙醇、正丙醇、戊醇、苄醇、呋喃甲醇及四氫呋喃甲醇等醇類;甲基乙基酮、甲基異丙基酮及甲基丁基酮等酮類;苯、甲苯及二甲苯等芳香族烴;三乙胺、吡啶、二㗁烷及乙腈等。
本發明之硬化性樹脂組合物視需要可含有其他各種添加劑。
作為上述添加劑,可例舉:γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-N'-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-苯胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三乙氧基矽烷、乙烯基三乙氧基矽烷、N-β-(N-乙烯基苄基胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷及γ-巰基丙基三甲氧基矽烷等矽烷偶合劑;聯苯酚等酚化合物;單烷基縮水甘油醚等反應性稀釋劑;鄰苯二甲酸二辛酯、鄰苯二甲酸二丁酯、苄醇及煤焦油等非反應性稀釋劑(塑化劑);玻璃布、芳香族聚醯胺布、碳纖維等補強材料;顏料;堪地里拉蠟、巴西棕櫚蠟、木蠟、蟲蠟、蜂蠟、羊毛脂、鯨蠟、褐煤蠟、石油蠟、脂肪族蠟、脂肪族酯、脂肪族醚、芳香族酯及芳香族醚等潤滑劑;增黏劑;觸變劑;消泡劑;防銹劑;磷系、酚系及硫系抗氧化劑;紫外線吸收劑;受阻胺系穩定劑;膠體二氧化矽及膠體氧化鋁等常用之添加劑。本發明中,進而亦可併用氰酸酯樹脂、二甲苯樹脂及石油樹脂等黏著性樹脂類。
本發明之硬化性樹脂組合物因含有特定之化合物而可成為儲存穩定性優異且硬化物之熱穩定性優異者。即,認為本發明之化合物由於具有以醯亞胺骨架為中心之特定結構而與硬化劑發生作用,使得儲存穩定性提高,由於具有環氧基而於硬化後未發生游離,因此硬化物之熱穩定性不會降低。本發明之硬化性樹脂組合物可適宜地用作一液硬化型之硬化性樹脂組合物。作為本發明之硬化性樹脂組合物之用途,並無特別限制,例如可例舉:電子零件接著劑、電子零件密封材料、澆鑄材料、塗料及結構接著劑等。
[實施例]
其次,藉由實施例及比較例進一步詳細地說明本發明,但本發明並不受該等實施例之任何限定。
[實施例1]
於安裝有迪安-斯塔克管及李比希冷凝管之50 mL之二口燒瓶中加入鄰苯二甲酸酐(1.4904 g、10.062 mmol)、及2-胺基乙硫醇(0.7766 g、10.066 mmol)後,添加甲苯(10 mL),進行加熱回流。16小時後,於空氣冷卻後,用蒸發器將反應溶液濃縮。利用矽膠管柱層析法將所得混合物進行精製(己烷/乙酸乙酯=3/1(體積比)),藉此以淡黃色固體之形式獲得硫醇化合物(1.9237 g、9.282 mmol、產率92%)。
於50 mL之二口燒瓶中加入上述所得之硫醇化合物(1.0359 g、4.998 mmol)及AIBN(2,2'-偶氮二異丁腈、41.8 mg、0.25 mmol),並設為氮氣氛圍。其後,添加藉由減壓操作而除去了殘存氧之N,N-二甲基甲醯胺(5 mL)而製成均勻溶液後,添加烯丙基縮水甘油醚(0.5827 g、5.105 mmol),藉由於70℃加熱所得溶液而進行反應。16小時後,於空氣冷卻後,用蒸發器將反應溶液濃縮。利用矽膠管柱層析法將所得混合物進行精製(己烷/乙酸乙酯=3/1~2/1體積比),藉此以淡黃色液體之形式獲得環氧醯亞胺(1.3525 g、4.185 mmol、產率84%)。
所得淡黃色液體之
1H-NMR測定結果示於圖1。使用氘氯仿作為測定溶劑。
根據該等結果,確認所得淡黃色液體為圖1中記載之化合物1A-1與化合物1B-1[質量比87/13]之混合物(以下記為「EP-IMIDE」)。
[實施例2]
於樣品瓶中加入Adeka Resin EP-4100L(ADEKA製造;雙酚A型環氧樹脂)(BADGE)613.1 mg(1.801 mmol)、實施例1中所得化合物之混合物(EP-IMIDE)194.5 mg(0.6052 mmol)、及2-乙基-4-甲基咪唑(EMI)22.0 mg(0.1997 mmol)並加以混合,藉此製備液狀硬化性樹脂組合物。
將上述硬化性樹脂組合物之一部分(10 mg)移至鋁鍋,於130℃硬化3小時,於升溫速度10℃、氮氣氛圍下對所得硬化物進行熱重量分析。
又,藉由將上述硬化性樹脂組合物於室溫保存於暗處並確認組合物之流動性,來評估儲存穩定性。結果示於表1。再者,表1中之調配比係將環氧樹脂之莫耳數設為100時之莫耳比。
[比較例1]BADGE:EMI=100:5
於樣品瓶中加入Adeka Resin EP-4100L(ADEKA製造;雙酚A型環氧樹脂)(BADGE)680.3 mg(1.998 mmol)及EMI(22.0 mg、0.1997 mmol)並加以混合,藉此製備液狀硬化性樹脂組合物。
[評估1:熱穩定性]
將上述硬化性樹脂組合物之一部分(8 mg)移至鋁鍋,於130℃硬化3小時,於升溫速度10℃、氮氣氛圍下對所得硬化物進行熱重量分析。5%重量損失溫度超過300℃者判斷為合格(A),將其示於表1。
又,藉由將上述硬化性樹脂組合物於室溫保存於暗處並確認組合物之流動性,來評估儲存穩定性。結果示於表1。
[評估2:儲存穩定性]
於直徑13 mm、高度40 mm之玻璃瓶中以液面位於距瓶下5分之1高度之量加入硬化性樹脂組合物,並蓋上瓶蓋。將其以傾斜90°之方式置於水平桌面上,觀察1分鐘後之狀態,確認是否具有流動性。於硬化性樹脂組合物之形狀發生變化之情形時,確認其具有流動性,於無變化之情形時,確認其不具有流動性。每放置1天,進行1次評估,流動性消失時評估結束。流動性可保持之天數示於表1。於流動性可保持3天以上之情形時,判斷為儲存穩定性合格(A),不滿足此項者判斷為儲存穩定性不合格(B)。
[表1]
實施例2 | 比較例1 | |||
組成(莫耳比) | (A)醯亞胺化合物 | EP-IMIDE | 34 | |
(B)環氧樹脂 | EP-4100L | 100 | 100 | |
(C)硬化劑 | EMI | 11 | 10 | |
評估1 | 熱重量分析 | 5%重量損失溫度(℃) | 327 | 404 |
10%重量損失溫度(℃) | 370 | 414 | ||
判定熱穩定性是否合格 | A | A | ||
評估2 | 儲存穩定性(天) | 7 | 2 | |
判定儲存穩定性是否合格 | A | B |
由上述評估結果可知,藉由使用本發明之化合物之EP-IMIDE,硬化物之熱穩定性與不添加醯亞胺化合物之情形同樣地優異,且與不添加醯亞胺化合物之情形相比,儲存穩定性提高5天。
[產業上之可利用性]
根據本發明,尤其可提供一種儲存穩定性優異之一液硬化型之硬化性樹脂組合物,例如可適宜地用於電子零件接著劑、電子零件密封材料、澆鑄材料、塗料、結構接著劑等。
圖1係表示實施例1中所製造之化合物之
1H-NMR測定結果之圖表。
Claims (7)
- 一種化合物,其由下述式(1)表示, [化1] 式(1)中,R 1表示氫原子或甲基,R 2、R 3、R 4及R 5分別獨立地表示氫原子、碳數1~10之烷基、碳數1~10之烷氧基、碳數1~10之烷醯氧基、碳數1~10之烷氧羰基、碳數1~10之烷醯胺基、碳數1~10之醯胺基、鹵素原子、羥基、硝基或腈基,A 1表示碳數1~20之伸烷基,A 2表示伸丙基或伸異丙基。
- 如請求項1之化合物,其由下述式(1A)或(1B)表示, [化2] 上述式(1A)中,R 1a表示氫原子或甲基,R 6表示氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基; [化3] 上述式(1B)中,R 1b表示氫原子或甲基,R 7表示氫原子、碳數1~4之烷基、鹵素原子、羥基或硝基。
- 一種硬化性樹脂組合物,其含有如請求項1或2之化合物作為(A)成分,含有環氧樹脂作為(B)成分,及含有硬化劑作為(C)成分。
- 如請求項3之硬化性樹脂組合物,其中作為(C)成分之硬化劑含有咪唑系硬化劑。
- 如請求項3或4之硬化性樹脂組合物,其中作為(A)成分之化合物之含量相對於作為(C)成分之硬化劑100質量份為1~2000質量份,作為(C)成分之硬化劑之含量相對於作為(B)成分之環氧樹脂100質量份為0.01~100質量份。
- 如請求項3或4之硬化性樹脂組合物,其為一液硬化型。
- 一種硬化物,其係如請求項3至6中任一項之硬化性樹脂組合物之硬化物。
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