CN105473631A - Light/moisture-curable resin composition, adhesive for electronic components, and adhesive for display elements - Google Patents
Light/moisture-curable resin composition, adhesive for electronic components, and adhesive for display elements Download PDFInfo
- Publication number
- CN105473631A CN105473631A CN201580001617.8A CN201580001617A CN105473631A CN 105473631 A CN105473631 A CN 105473631A CN 201580001617 A CN201580001617 A CN 201580001617A CN 105473631 A CN105473631 A CN 105473631A
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- CN
- China
- Prior art keywords
- mentioned
- moisture
- curable resin
- methyl
- resin combination
- Prior art date
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- 239000011342 resin composition Substances 0.000 title abstract description 11
- 230000001070 adhesive effect Effects 0.000 title abstract 6
- 239000000853 adhesive Substances 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 229920005989 resin Polymers 0.000 claims description 114
- 239000011347 resin Substances 0.000 claims description 114
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 38
- 230000003287 optical effect Effects 0.000 claims description 22
- 238000010526 radical polymerization reaction Methods 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 16
- 239000011164 primary particle Substances 0.000 claims description 11
- 230000001235 sensitizing effect Effects 0.000 claims description 11
- 238000007711 solidification Methods 0.000 claims description 9
- 230000008023 solidification Effects 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 49
- 239000007870 radical polymerization initiator Substances 0.000 abstract 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 abstract 1
- -1 (methyl) acryl Chemical group 0.000 description 66
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 52
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 38
- 239000003822 epoxy resin Substances 0.000 description 37
- 229920000647 polyepoxide Polymers 0.000 description 37
- 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 22
- 238000000034 method Methods 0.000 description 22
- 229920005862 polyol Polymers 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 16
- 239000010936 titanium Substances 0.000 description 16
- 229910052719 titanium Inorganic materials 0.000 description 16
- 239000004593 Epoxy Chemical class 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 229930185605 Bisphenol Natural products 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000016 photochemical curing Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 229940117927 ethylene oxide Drugs 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 230000005661 hydrophobic surface Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 150000003553 thiiranes Chemical class 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000006227 trimethylsilylation reaction Methods 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical class ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- YUTHQCGFZNYPIG-UHFFFAOYSA-N 1-[2-(2-methylprop-2-enoyloxy)ethyl]cyclohexane-1,2-dicarboxylic acid Chemical compound CC(=C)C(=O)OCCC1(C(O)=O)CCCCC1C(O)=O YUTHQCGFZNYPIG-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- KZNJSFHJUQDYHE-UHFFFAOYSA-N 1-methylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1 KZNJSFHJUQDYHE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- ZTADSGAMBXVFBV-UHFFFAOYSA-N 1-phosphonooxypropan-2-yl prop-2-enoate Chemical compound OP(=O)(O)OCC(C)OC(=O)C=C ZTADSGAMBXVFBV-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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Abstract
The purpose of the present invention is to provide a light/moisture-curable resin composition that exhibits excellent light shielding properties and adhesive properties. Another purpose of the present invention is to provide an adhesive for electronic components and an adhesive for display elements, said adhesives comprising the light/moisture-curable resin composition. The present invention is a light/moisture-curable resin composition that contains a radically polymerizable compound, a moisture-curable urethane resin, a photo-radical polymerization initiator, and a light shielding agent.
Description
Technical field
The present invention relates to opacifying property and light moisture-curable resin combination excellent in adhesion.In addition, the present invention relates to and use this light moisture-curable resin combination and the electronic component-use caking agent made and display element caking agent.
Background technology
In recent years, as the display element with features such as slim, light weight, low power consumptions, liquid crystal display device, organic EL display element etc. are widely used.In these display elements, usually, in the sealing of liquid crystal, luminescent layer, substrate, blooming, protective membrane, various component bonding etc. in, employ photocurable resin composition.
In addition, in the various modern times day by day popularized with the mobile equipment of display element such as portable phone, portable game, the miniaturization of display element is the problem be required most, as the method for miniaturization, narrow edge (hereinafter also referred to as narrow edge design) has been carried out to image displaying part.But in narrow edge design, the part sometimes fully do not arrived at light is coated with photocurable resin composition, consequently, exist and coat the insufficient problem of the solidification of the photocurable resin composition of the part that light does not arrive.
In addition, even if when photocurable resin composition is configured at the part that light fully do not arrive, also there are the following problems: cannot carry out shading to from the luminescent part of display element through the light of photocurable resin composition, cause contrast gradient to reduce due to light leak.
Therefore, in order to give opacifying property to photocurable resin composition, the method for adding opalizer can be considered.But there is the insufficient problem of photocuring in the photocurable resin composition that with the addition of opalizer.Patent Document 1 discloses, even if coordinate the method for opalizer in the photo-thermal curing type resin combination fully solidified when also making it by heating when photocuring is insufficient, but, likely due to heating at high temperature, detrimentally affect is brought to element etc.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2006-099027 publication
Summary of the invention
Invent problem to be solved
The object of the present invention is to provide opacifying property and light moisture-curable resin combination excellent in adhesion.In addition, the object of the present invention is to provide and use this light moisture-curable resin combination and the electronic component-use caking agent made and display element caking agent.
For solving the means of problem
Smooth moisture-curable resin combination of the present invention contains free-radical polymerised compound, moisture-curable carbamate resins, optical free radical polymerization starter and opalizer.
Below the present invention is described in detail.
The discoveries such as the present inventor, the method making it solidify as not carrying out the heating under high temperature to the resin combination containing opalizer, by coordinating opalizer in the light moisture-curable resin combination containing free-radical polymerised compound, moisture-curable carbamate resins and optical free radical polymerization starter, thus all excellent light moisture-curable resin combination of both opacifying property and cementability can be obtained, to such an extent as to complete the present invention.
Smooth moisture-curable resin combination of the present invention contains opalizer.By containing above-mentioned opalizer, the opacifying property of smooth moisture-curable resin combination of the present invention becomes excellent, can prevent the light leak of display element.
It should be noted that, in this manual, above-mentioned " opalizer " refer to have make the light of visible region be difficult to through the material of ability.
As above-mentioned opalizer, can enumerate such as ferric oxide, titanium is black, nigrosine, cyanine are black, soccerballene, carbon black, resin-coated type carbon black etc.In addition, above-mentioned opalizer can not be also black, as long as have make the light of visible region be difficult to through the material of ability, silicon-dioxide, talcum etc. are also contained in above-mentioned opalizer by the material etc. exemplified as weighting agent described later.Wherein, preferred titanium is black.
Above-mentioned titanium is black is compared with the average transmittance of the light for wavelength 300 ~ 800nm, near ultra-violet region, and the material that particularly transmissivity of the light of wavelength 370 ~ 450nm is higher.That is, above-mentioned titanium is black is the opalizer with following character, namely, by covering the light of the wavelength of visible region fully, thus give opacifying property to smooth moisture-curable resin combination of the present invention, on the other hand, make the Transmission light of the wavelength near ultra-violet region.Therefore, by using the light of the wavelength (370 ~ 450nm) that the black transmissivity of above-mentioned titanium can be utilized to uprise to carry out the material of initiation reaction as optical free radical polymerization starter, thus the light solidified of smooth moisture-curable resin combination of the present invention can be increased further.In addition, on the other hand, as the opalizer contained in smooth moisture-curable resin combination of the present invention, the material that preferred insulativity is high, as the opalizer that insulativity is high, also preferably titanium is black.
The optical concentration (OD value) that above-mentioned titanium is black is preferably more than 3, is more preferably more than 4.In addition, the degree of blackness (L value) that above-mentioned titanium is black is preferably more than 9, more preferably more than 11.The opacifying property that above-mentioned titanium is black is more high better, and the preferred upper limit of the OD value that above-mentioned titanium is black is not particularly limited, and is generally less than 5.
Even the black not surface treated material of above-mentioned titanium, also given play to sufficient effect, can also use that surface utilizes the material of the organic composition process such as coupling agent, surface utilizes the surface treated titaniums such as the covered material of inorganic components such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium white, magnesium oxide black.Wherein, with the titanium of organic composition process black can improve further insulativity in preferred.
In addition, the liquid crystal display device manufactured for using smooth moisture-curable resin combination of the present invention, because light moisture-curable resin combination has sufficient opacifying property, therefore, it is possible to realization does not have spilling of light and has high-contrast, and there is excellent display quality of image.
Commercially available product in black as above-mentioned titanium, can enumerate such as 12S, 13M, 13M-C, 13R-N (being Mitsubishi Materials Corp's system), TilackD (red fringe changes into Inc.) etc.
The preferred lower limit of the specific surface area that above-mentioned titanium is black is 5m
2/ g, preferred upper limit is 40m
2/ g, more preferably lower limit is 10m
2/ g, more preferably the upper limit is 25m
2/ g.
In addition, the preferred lower limit of the sheet resistance (シ mono-foretells opposing) that above-mentioned titanium is black when with (70% coordinates) when mixed with resin, be 10
9Ω/, more preferably lower limit is 10
11Ω/.
In smooth moisture-curable resin combination of the present invention, the primary particle size of above-mentioned opalizer is such as the following according to the distance between the substrate of display element, purposes and suitably selecting, and preferred lower limit is 30nm, and preferred upper limit is 500nm.If the primary particle size of above-mentioned opalizer is less than 30nm, then the viscosity of the light moisture-curable resin combination of gained, thixotropy enlarge markedly sometimes, and operability is deteriorated.If the primary particle size of above-mentioned opalizer is greater than 500nm, then the dispersiveness of the opalizer in the light moisture-curable resin combination of gained sometimes reduces, and opacifying property reduces sometimes.More preferably the lower limit of the primary particle size of above-mentioned opalizer is 50nm, and more preferably the upper limit is 200nm.
The content of the above-mentioned opalizer in smooth moisture-curable resin combination entirety of the present invention is not particularly limited, and preferred lower limit is 0.05 % by weight, and preferred upper limit is 10 % by weight.If the content of above-mentioned opalizer is less than 0.05 % by weight, then sometimes cannot obtain sufficient opacifying property.If the content of above-mentioned opalizer is greater than 10 % by weight, then sometimes gained light moisture-curable resin combination relative to substrate etc. cementability, solidification after intensity reduce, or drawing property reduce.More preferably the lower limit of the content of above-mentioned opalizer is 0.1 % by weight, and more preferably the upper limit is 2 % by weight, and further preferred lower limit is 0.3 % by weight, and further preferred upper limit is 1 % by weight.
Smooth moisture-curable resin combination of the present invention contains free-radical polymerised compound.
As above-mentioned free-radical polymerised compound; as long as have the compound of free-radical reactive functional group in molecule; be not particularly limited; as free-radical reactive functional group; preferably there is the compound of unsaturated double-bond; particularly from reactive aspect, preferably there is the resin (hereinafter also referred to as " (methyl) acrylic resin ") of (methyl) acryl.
It should be noted that, in this specification sheets, above-mentioned " (methyl) acryl " represents acryl or methacryloyl, and above-mentioned " (methyl) acrylic acid or the like " represents acrylic acid or the like or methacrylic.
As above-mentioned (methyl) acrylic resin, can enumerate and such as obtain ester cpds by making (methyl) vinylformic acid react with the compound with hydroxyl; By epoxy group(ing) (methyl) acrylate making (methyl) vinylformic acid and epoxy compounds react and obtain; Carbamate (methyl) acrylate etc. is obtained by making isocyanic ester react with (methyl) acrylic acid derivative with hydroxyl.
It should be noted that, in this specification sheets, above-mentioned " (methyl) acrylate " refers to acrylate or methacrylic ester.
As the monofunctional compound in above-mentioned ester cpds, the phthalic imidine esters of acrylic acids such as such as N-acryloyl-oxyethyl hexahydrophthalic phthalimide can be enumerated, various imide acrylate, (methyl) vinylformic acid-2-hydroxyl ethyl ester, (methyl) 2-hydroxypropyl acrylate, (methyl) vinylformic acid-4-hydroxy butyl ester, (methyl) vinylformic acid-2-hydroxy butyl ester, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) Isooctyl acrylate monomer, (methyl) lauryl acrylate, (methyl) octadecyl acrylate, (methyl) isobornyl acrylate, (methyl) cyclohexyl acrylate, (methyl) vinylformic acid-2-methoxy acrylate, methoxyl group ethylene glycol (methyl) acrylate, (methyl) vinylformic acid-2-ethoxy ethyl ester, (methyl) vinylformic acid tetrahydro furfuryl ester, (methyl) benzyl acrylate, ethyl carbitol (methyl) acrylate, (methyl) acrylate, phenoxy group Diethylene Glycol (methyl) acrylate, phenoxy group polyoxyethylene glycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, 2,2,2-trifluoroethyl (methyl) acrylate, 2,2,3,3-tetra-fluoropropyl (methyl) acrylate, 1H, 1H, 5H-octafluoro amyl group (methyl) acrylate, imide (methyl) acrylate, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) n-butyl acrylate, (methyl) propyl acrylate, (methyl) ethyl acrylate, (methyl) n-octyl, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, the different myristin of (methyl) vinylformic acid, (methyl) vinylformic acid-2-butoxyethyl, (methyl) vinylformic acid-2-phenoxy ethyl, (methyl) vinylformic acid dicyclopentenyloxyethyl methacrylate, (methyl) isodecyl acrylate, diethylamino ethyl (methyl) acrylate, dimethyl aminoethyl (methyl) acrylate, 2-(methyl) acryloyl-oxyethyl succsinic acid, 2-(methyl) acryloyl-oxyethyl hexahydrophthalic acid, 2-(methyl) acryloyl-oxyethyl-2-hydroxypropylphthalate, (methyl) glycidyl acrylate, 2-(methyl) acryloyl-oxyethyl phosphoric acid ester etc.
In addition, as the compound of 2 officials' energy in above-mentioned ester cpds, such as BDO two (methyl) acrylate can be enumerated, 1,3 butylene glycol two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate, decamethylene-glycol two (methyl) acrylate, 2-normal-butyl-2-ethyl-1,3-PD two (methyl) acrylate, dipropylene glycol two (methyl) acrylate, tripropylene glycol two (methyl) acrylate, polypropylene glycol (methyl) acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, Diethylene Glycol two (methyl) acrylate, TEG two (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, propylene oxide addition dihydroxyphenyl propane two (methyl) acrylate, ethyleneoxide addition dihydroxyphenyl propane two (methyl) acrylate, ethyleneoxide addition Bisphenol F two (methyl) acrylate, dihydroxymethyl dicyclopentadienyl two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, ethylene-oxide-modified isocyanuric acid two (methyl) acrylate, 2-hydroxyl-3-(methyl) acryloxypropyl (methyl) acrylate, carbonate diol two (methyl) acrylate, polyether glycol two (methyl) acrylate, polyester glycol two (methyl) acrylate, polycaprolactone glycol two (methyl) acrylate, polybutadiene diol two (methyl) acrylate etc.
In addition, can above compound as 3 officials in above-mentioned ester cpds, such as tetramethylolmethane three (methyl) acrylate can be enumerated, trimethylolpropane tris (methyl) acrylate, propylene oxide addition trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition isocyanuric acid three (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, ditrimethylolpropane four (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, glycerol three (methyl) acrylate, propylene oxide addition glycerol three (methyl) acrylate, three (methyl) acryloyl-oxyethyl phosphoric acid ester etc.
As above-mentioned epoxy (methyl) acrylate, can enumerate and such as make epoxy compounds and (methyl) vinylformic acid conventionally react under the existence of basic catalyst and epoxy (methyl) acrylate etc. of acquisition.
As the epoxy compounds of the raw material become for the synthesis of above-mentioned epoxy (methyl) acrylate, such as bisphenol A type epoxy resin can be enumerated, bisphenol f type epoxy resin, bisphenol-s epoxy resin, 2, 2 '-diallyl bisphenol type epoxy resin, A Hydrogenated Bisphenol A type epoxy resin, propylene oxide addition bisphenol A type epoxy resin, Resorcinol type epoxy resin, biphenyl type epoxy resin, thioether-type epoxy resin, phenylbenzene ether type epoxy, dicyclopentadiene-type epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, o-cresol phenolic epoxy varnish, dicyclopentadiene novolac type epoxy resin, biphenyl phenolic resin varnish type epoxy resin, naphthol novolac type epoxy resin, glycidyl amine type epoxy resin, alkyl polyols type epoxy resin, modified rubber type epoxy resin, epihydric alcohol ester compound, bisphenol A-type episulfide resin etc.
As the commercially available product in above-mentioned bisphenol A type epoxy resin, such as jER828EL, jER1001, jER1004 (being Mitsubishi Chemical Ind's system), EPICLON850-S (DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned bisphenol f type epoxy resin, such as jER806, jER4004 (being Mitsubishi Chemical Ind's system) etc. can be enumerated.
As the commercially available product in above-mentioned bisphenol-s epoxy resin, such as EPICLONEXA1514 (DIC Inc.) etc. can be enumerated.
As above-mentioned 2, the commercially available product in 2 '-diallyl bisphenol type epoxy resin, can enumerate such as RE-810NM (Japanese chemical drug Inc.) etc.
As the commercially available product in above-mentioned A Hydrogenated Bisphenol A type epoxy resin, such as EPICLONEXA7015 (DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned propylene oxide addition bisphenol A type epoxy resin, such as EP-4000S (ADEKA Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned Resorcinol type epoxy resin, such as EX-201 (NagaseChemtex Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned biphenyl type epoxy resin, such as jERYX-4000H (Mitsubishi Chemical Ind's system) etc. can be enumerated.
As the commercially available product in above-mentioned thioether-type epoxy resin, such as YSLV-50TE (aurification Inc. is lived by Nippon Steel) etc. can be enumerated.
As the commercially available product in above-mentioned phenylbenzene ether type epoxy, such as YSLV-80DE (aurification Inc. is lived by Nippon Steel) etc. can be enumerated.
As the commercially available product in above-mentioned dicyclopentadiene-type epoxy resin, such as EP-4088S (ADEKA Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned naphthalene type epoxy resin, such as EPICLONHP4032, EPICLONEXA-4700 (being DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned phenol novolak type epoxy resin, such as EPICLONN-770 (DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned o-cresol phenolic epoxy varnish, such as EPICLONN-670-EXP-S (DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned dicyclopentadiene novolac type epoxy resin, such as EPICLONHP7200 (DIC Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned biphenyl phenolic resin varnish type epoxy resin, such as NC-3000P (Japanese chemical drug Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned naphthol novolac type epoxy resin, such as ESN-165S (aurification Inc. is lived by Nippon Steel) etc. can be enumerated.
As the commercially available product in above-mentioned glycidyl amine type epoxy resin, such as jER630 (Mitsubishi Chemical Ind's system), EPICLON430 (DIC Inc.), TETRAD-X (gas chemical company of Mitsubishi system) etc. can be enumerated.
As the commercially available product in abovementioned alkyl polyol type epoxy resin, such as ZX-1542 (aurification Inc. is lived by Nippon Steel), EPICLON726 (DIC Inc.), EPOLIGHT80MFA (chemical company of common prosperity society system), DENACOLEX-611 (NagaseChemtex Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned modified rubber type epoxy resin, such as YR-450, YR-207 (be Nippon Steel and live aurification Inc.), EPOLEADPB (Daicel Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned epihydric alcohol ester compound, such as DENACOLEX-147 (NagaseChemtex Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned bisphenol A-type episulfide resin, such as jERYL-7000 (Mitsubishi Chemical Ind's system) etc. can be enumerated.
As other commercially available product in above-mentioned epoxy resin, such as YDC-1312, YSLV-80XY, YSLV-90CR (be Nippon Steel and live aurification Inc.), XAC4151 (Asahi Kasei Corporation's system), jER1031, jER1032 (being Mitsubishi Chemical Ind's system), EXA-7120 (DIC Inc.), TEPIC (Nissan Chemical Inc.) etc. can be enumerated.
As the commercially available product in above-mentioned epoxy (methyl) acrylate, such as EBECRYL860 can be enumerated, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYLRDX63182 (being DAICELALLNEXLTD. system), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (being chemical industrial company of Xin Zhong village system), EPOXYESTERM-600A, EPOXYESTER40EM, EPOXYESTER70PA, EPOXYESTER200PA, EPOXYESTER80MFA, EPOXYESTER3002M, EPOXYESTER3002A, EPOXYESTER1600A, EPOXYESTER3000M, EPOXYESTER3000A, EPOXYESTER200EA, EPOXYESTER400EA (being chemical company of common prosperity society system), DENACOLACRYLATEDA-141, DENACOLACRYLATEDA-314, DENACOLACRYLATEDA-911 (being NagaseChemtex Inc.) etc.
Under above-mentioned carbamate (methyl) acrylate can be existed by the tin based compound such as at catalytic amount, compound 1 equivalent making to have 2 isocyanate group with there is (methyl) acrylic acid derivative 2 equivalent reaction of hydroxyl and obtain.
As the isocyanic ester of raw material becoming above-mentioned carbamate (methyl) acrylate, such as isophorone diisocyanate can be enumerated, 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, ditan-4, 4 '-vulcabond (MDI), hydrogenation MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornene alkyl diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenation XDI, lysinediisocyanate, triphenylmethane triisocyanate, three (isocyanate phenyl) thiophosphatephosphorothioate, tetramethylxylene diisocyanate, 1, 6, 11-undecane triisocyanate etc.
In addition, as above-mentioned isocyanic ester, can also use such as by the reaction of the polyvalent alcohols such as ethylene glycol, glycerol, Sorbitol Powder, TriMethylolPropane(TMP), (gathering) propylene glycol, carbonate diol, polyether glycol, polyester glycol, polycaprolactone glycol and excessive isocyanic ester and the isocyanate compound of the chain extension obtained.
As become above-mentioned carbamate (methyl) acrylate raw material, (methyl) acrylic acid derivative with hydroxyl, such as ethylene glycol, propylene glycol, 1 can be enumerated, ammediol, 1, epoxy (methyl) acrylate etc. such as list (methyl) acrylate of the trivalent alcohol such as list (methyl) acrylate, trimethylolethane, TriMethylolPropane(TMP), glycerol of the dibasic alcohol such as 3-butyleneglycol, BDO, polyoxyethylene glycol or two (methyl) acrylate, bisphenol type epoxy (methyl) acrylate.
As the commercially available product in above-mentioned carbamate (methyl) acrylate, such as M-1100 can be enumerated, M-1200, M-1210, M-1600 (being East Asia Synesis Company system), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (being DAICELALLNEXLTD. system), ArtresinUN-9000H, ArtresinUN-9000A, ArtresinUN-7100, ArtresinUN-1255, ArtresinUN-330, ArtresinUN-3320HB, ArtresinUN-1200TPK, ArtresinSH-500B (being Gen Shang industrial system), U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U-122P, U-108, U-108A, U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (being chemical industrial company of Xin Zhong village system), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (being chemical company of common prosperity society system) etc.
In addition, also other free-radical polymerised compounds other than the above can suitably be used.
As other above-mentioned free-radical polymerised compounds, such as N can be enumerated, N-dimethyl (methyl) acrylamide, N-(methyl) acryloyl morpholine, N-hydroxyethyl (methyl) acrylamide, N, the vinyl compounds etc. such as (methyl) acrylamide compound, vinylbenzene, alpha-methyl styrene, NVP, N-vinyl caprolactam such as N-diethyl (methyl) acrylamide, N-sec.-propyl (methyl) acrylamide, N, N-dimethylaminopropyl (methyl) acrylamide.
From viewpoints such as adjustment solidified nature, above-mentioned free-radical polymerised compound is preferably containing monofunctional free radical's polymerizable compound and multifunctional free-radical polymerised compound.When only using monofunctional free radical's polymerizable compound, the solidified nature of the light moisture-curable resin combination of gained is poor sometimes, and when only using multifunctional free-radical polymerised compound, the viscosity of the light moisture-curable resin combination of gained is poor sometimes.Wherein, the compound in the molecule as above-mentioned monofunctional free radical's polymerizable compound with nitrogen-atoms and carbamate (methyl) acrylate as above-mentioned multifunctional free-radical polymerised compound is more preferably combinationally used.In addition, above-mentioned multifunctional free-radical polymerised compound preferably 2 officials can or 3 officials can, more preferably 2 official's energy.
When above-mentioned free-radical polymerised compound contains above-mentioned monofunctional free radical's polymerizable compound and above-mentioned multifunctional free-radical polymerised compound, relative to total 100 weight part of above-mentioned monofunctional free radical's polymerizable compound and above-mentioned multifunctional free-radical polymerised compound, the preferred lower limit of the content of above-mentioned multifunctional free-radical polymerised compound is 2 weight parts, and preferred upper limit is 30 weight parts.If the content of above-mentioned multifunctional free-radical polymerised compound is less than 2 weight parts, then the solidified nature of the light moisture-curable resin combination of gained is poor sometimes.If the content of above-mentioned multifunctional free-radical polymerised compound is greater than 30 weight parts, then the viscosity of the light moisture-curable resin combination of gained is poor sometimes.More preferably the lower limit of the content of above-mentioned multifunctional free-radical polymerised compound is 5 weight parts, and more preferably the upper limit is 20 weight parts.
Smooth moisture-curable resin combination of the present invention contains moisture-curable carbamate resins.For above-mentioned moisture-curable carbamate resins, the reaction of moisture in intramolecular isocyanate group and air or in adherend and solidifying.In addition, with use have the compound of bridging property silyl etc. as moisture-curable composition situation compared with, the quick solidification of the light moisture-curable resin combination of gained is excellent.
For above-mentioned moisture-curable carbamate resins, in 1 molecule, only can contain 1 isocyanate group, also can containing more than 2.Wherein, preferably there is at two ends the carbamate prepolymer of isocyanate group.
Above-mentioned carbamate prepolymer can obtain by the following method, that is, make to have in 1 molecule the polyol compound of more than 2 hydroxyls, with 1 molecule in there is the isocyanate group of more than 2 polyisocyanates based compound react.
The hydroxyl of reaction usually in polyol compound (OH) of above-mentioned polyol compound and polyisocyanates based compound and the mol ratio of the isocyanate group (NCO) in polyisocyanates based compound are carry out in the scope of [NCO]/[OH]=2.0 ~ 2.5.
As above-mentioned polyol compound, the normally used known polyol compound of manufacture of urethane can be used in, such as polyester polyol, polyether glycol, tool alkylidene polyol, polycarbonate polyol etc. can be enumerated.These polyol compounds may be used alone, two or more kinds can also be used in combination.
As above-mentioned polyester polyol, can enumerate such as by the reaction of polycarboxylic acid and polyvalent alcohol and the polyester polyol obtained, poly-6-caprolactone polyvalent alcohol etc. that 6-caprolactone ring-opening polymerization is obtained.
As the above-mentioned polycarboxylic acid of raw material becoming above-mentioned polyester polyol, such as terephthalic acid, m-phthalic acid, 1 can be enumerated, 5-naphthalic acid, NDA, succsinic acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, nonane diacid, sebacic acid, decamethylene dicarboxylic acid, ten dimethylene dicarboxylic acid etc.
As the above-mentioned polyvalent alcohol of raw material becoming above-mentioned polyester polyol, such as ethylene glycol, propylene glycol, 1,3-PD, BDO, neopentyl glycol, 1,5-PD, 1,6-hexylene glycol, glycol ether, cyclohexane diol etc. can be enumerated.
As above-mentioned polyether glycol, the polyoxyalkylene-modified body etc. of the such as ring-opening polymerization polymer of ethylene glycol, propylene glycol, tetrahydrofuran (THF), 3-methyltetrahydrofuran and the random copolymers of they or they derivative or segmented copolymer, bisphenol type can be enumerated.
The polyoxyalkylene-modified body of above-mentioned bisphenol type makes the active hydrogen moieties of bisphenol type molecular skeleton and oxirane (such as, oxyethane, propylene oxide, butylene oxide ring, epoxy Trimethylmethane etc.) carry out addition reaction and the polyether glycol obtained, can be random copolymers, also can be segmented copolymer.
The polyoxyalkylene-modified body of above-mentioned bisphenol type preferably has one kind or two or more oxirane at two terminal additions of bisphenol type molecular skeleton.As bisphenol type, be not particularly limited, A type, F type, S type etc. can be enumerated, be preferably bisphenol A-type.
As above-mentioned polyalkylene polyol, such as polybutadiene polyol, hydrogenated butadiene polymer polyvalent alcohol, hydrogenated polyisoprene polyvalent alcohol etc. can be enumerated.
As above-mentioned polycarbonate polyol, such as polyhexamethylene carbonate polyol, poly-cyclohexanedimethyleterephthalate carbonate polyol etc. can be enumerated.
As above-mentioned polyisocyanate compound, the aqueous modifier of such as '-diphenylmethane diisocyanate, '-diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), tolylene diisocyanate, naphthalene-1,5-vulcabond etc. can be enumerated.Wherein, from vapour pressure, the aspect that toxicity is low, maneuverable aspect, preferred '-diphenylmethane diisocyanate and modifier thereof.Above-mentioned polyisocyanates based compound may be used alone, two or more kinds can also be used in combination.
In addition, above-mentioned moisture-curable carbamate resins preferably uses the polyol compound of the structure had represented by following formula (1) and the carbamate resins obtained.By using the polyol compound of the structure had represented by following formula (1), composition excellent in adhesion, softness and extend good cured article can be obtained, become the carbamate resins with the excellent compatibility of above-mentioned free-radical polymerised compound.
Wherein, preferably use comprise propylene glycol, tetrahydrofuran (THF) (THF) compound ring opening polymerizable compound, there is the polyether glycol of the ring opening polymerizable compound of the substituent tetrahydrofuran-compounds such as methyl.
In formula (1), R represents hydrogen, methyl or ethyl, and n is the integer of 1 ~ 10, and L is the integer of 0 ~ 5, and m is the integer of 1 ~ 500.N is preferably 1 ~ 5, L and is preferably 0 ~ 4, m and is preferably 50 ~ 200.
It should be noted that, L be 0 situation refer to, with the carbon of R bonding directly and the situation of oxygen bonding.
Further, above-mentioned moisture-curable carbamate resins can have free-radical polymerised functional group.
As the free-radical polymerised functional group that above-mentioned moisture-curable carbamate resins can have, preferably there is the group of unsaturated double-bond, particularly from reactive aspect, more preferably (methyl) acryl.
It should be noted that, the moisture-curable carbamate resins with free-radical polymerised functional group is not included in free-radical polymerised compound, but processes as moisture-curable carbamate resins.
The preferred lower limit of the weight-average molecular weight of above-mentioned moisture-curable carbamate resins is 800, and preferred upper limit is 10,000.If the weight-average molecular weight of above-mentioned moisture-curable carbamate resins is less than 800, then cross-linking density uprises sometimes, and flexibility is compromised.If the weight-average molecular weight of above-mentioned moisture-curable carbamate resins is greater than 10,000, then the coating of the light moisture-curable resin combination of gained is poor sometimes.More preferably the lower limit of the weight-average molecular weight of above-mentioned moisture-curable carbamate resins is 2000, and more preferably the upper limit is 8000, and further preferred lower limit is 3000, and further preferred upper limit is 6000.
It should be noted that, in this manual, above-mentioned weight-average molecular weight utilizes gel permeation chromatography (GPC) to measure, the value of being tried to achieve by polystyrene conversion.As the chromatographic column during weight-average molecular weight utilizing GPC mensuration based on polystyrene conversion, such as ShodexLF-804 (Showa electrician Inc.) etc. can be enumerated.In addition, as the solvent used in GPC, tetrahydrofuran (THF) etc. can be enumerated.
Relative to total 100 weight part of above-mentioned free-radical polymerised compound and above-mentioned moisture-curable carbamate resins, the preferred lower limit of the content of above-mentioned moisture-curable carbamate resins is 20 weight parts, and preferred upper limit is 90 weight parts.If the content of above-mentioned moisture-curable carbamate resins is less than 20 weight parts, then the moisture-curable of the light moisture-curable resin combination of gained is poor sometimes.If the content of above-mentioned moisture-curable carbamate resins is greater than 90 weight parts, then the light solidified of the light moisture-curable resin combination of gained is poor sometimes.More preferably the lower limit of the content of above-mentioned moisture-curable carbamate resins is 30 weight parts, and more preferably the upper limit is 75 weight parts, and further preferred lower limit is 41 weight parts, and further preferred upper limit is 70 weight parts.
Smooth moisture-curable resin combination of the present invention contains optical free radical polymerization starter.
As above-mentioned optical free radical polymerization starter; such as benzophenone based compound, methyl phenyl ketone based compound, acylphosphine oxide based compound, two luxuriant titanium sub-group compounds, oxime ester based compound, benzoin ether based compound, thioxanthone etc. can be enumerated; from the aspect that can obtain light solidified (deep solidified nature) composition excellent especially, preferred acylphosphine oxide based compound.In addition, the optical free radical polymerization starter that above-mentioned optical free radical polymerization starter preferably can be photosensitive as described above by the light of the wavelength region may of irradiation 370 ~ 450nm.
As above-mentioned acylphosphine oxide based compound, such as two (2,4,6-trimethylbenzoyl)-phenyl phosphine oxide, 2,4,6-trimethylbenzoyl diphenyl phosphine oxides etc. can be enumerated.
As the commercially available product in above-mentioned optical free radical polymerization starter, such as IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE4265, IRGACUREOXE01, LucirinTPO, (being BASFJapan Inc.), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (be Tokyo and change into industrial's system) etc. can be enumerated.
Relative to above-mentioned free-radical polymerised compound 100 weight part, the preferred lower limit of the content of above-mentioned optical free radical polymerization starter is 0.01 weight part, and preferred upper limit is 10 weight parts.If the content of above-mentioned optical free radical polymerization starter is less than 0.01 weight part, then the light moisture-curable resin combination of gained sometimes can not be made fully to carry out photocuring.If the content of above-mentioned optical free radical polymerization starter is greater than 10 weight parts, then the storage stability of the light moisture-curable resin combination of gained reduces sometimes.More preferably the lower limit of the content of above-mentioned optical free radical polymerization starter is 0.1 weight part, and more preferably the upper limit is 5 weight parts.
Smooth moisture-curable resin combination of the present invention can contain sensitizing agent.
Smooth moisture-curable resin combination of the present invention by containing above-mentioned sensitizing agent, and can obtain highly sensitive and the light moisture-curable resin combination of light solidified excellence.Above-mentioned sensitizing agent is preferably as described above by the sensitizing agent having been given play to sensitization effect by the rayed of the wavelength region may of 370 ~ 450nm.
Above-mentioned sensitizing agent preferably has sufficient optical absorption band in UV, visible light region, therefore, preferably containing the compound with at least one skeleton be selected from benzophenone skeletal, anthracene skeleton, anthraquinone skeleton, coumarin skeleton, thioxanthone skeleton and phthalocyanine frame, more preferably containing the compound with at least one skeleton be selected from anthracene skeleton and anthraquinone skeleton, thioxanthone skeleton.These compounds also can use as above-mentioned optical free radical polymerization starter.
As the above-mentioned compound with benzophenone skeletal, such as benzophenone, 2,4-dichloro benzophenones, 4 can be enumerated, 4 '-bis-(dimethylamino) benzophenone, 4,4 '-bis-(diethylamino) benzophenone etc.
As the above-mentioned compound with anthracene skeleton, such as 9,10-dibutoxy anthracenes, 9,10-dipropoxy anthraquinones, 9,10-oxyethyl group anthraquinones etc. can be enumerated.
As the above-mentioned compound with anthraquinone skeleton, such as 2-ethyl-anthraquinone, 1-methylanthracene quinone, Isosorbide-5-Nitrae-dihydroxyanthraquinone, 2-(2-hydroxyl-oxethyl)-anthraquinone etc. can be enumerated.
As the above-mentioned compound with coumarin skeleton, such as 7-diethylamino-4-methylcoumarin etc. can be enumerated.
As the above-mentioned compound with thioxanthone skeleton, such as 2,4-diethyl thioxanthones, CTX, ITX, 1-chloro-4-propyl group thioxanthone etc. can be enumerated.
As the above-mentioned compound with phthalocyanine frame, such as phthalocyanine etc. can be enumerated.
Among these sensitizing agents, the aspect of the composition that the solidified nature becoming light shielding part from the light moisture-curable resin combination of gained is excellent especially, preferred use 4, in 4 '-bis-(dimethylamino) benzophenone and 4,4 '-bis-(diethylamino) benzophenone at least any one.
Relative to above-mentioned Photoepolymerizationinitiater initiater 100 weight part, the preferred lower limit of the content of above-mentioned sensitizing agent is 2 weight parts, and preferred upper limit is 50 weight parts.If the content of above-mentioned sensitizing agent is less than 2 weight parts, then sensitization effect sometimes does not give full play to.If the content of above-mentioned sensitizing agent is greater than 50 weight parts, then the storage stability of the light moisture-curable resin combination of gained reduces sometimes.More preferably the lower limit of the content of above-mentioned sensitizing agent is 5 weight parts, and more preferably the upper limit is 40 weight parts.
From the view point of the coating, shape-holding property etc. of the light moisture-curable resin combination of adjustment gained, smooth moisture-curable resin combination of the present invention can contain weighting agent.By containing above-mentioned weighting agent, smooth moisture-curable resin combination of the present invention becomes and has suitable thixotropic composition, can keep the shape after being coated with fully.
The preferred lower limit of the primary particle size of above-mentioned weighting agent is 1nm, and preferred upper limit is 50nm.If the primary particle size of above-mentioned weighting agent is less than 1nm, then the coating of the light moisture-curable resin combination of gained is poor sometimes.If the primary particle size of above-mentioned weighting agent is greater than 50nm, then the shape-holding property after the coating of the light moisture-curable resin combination of gained is sometimes poor.More preferably the lower limit of the primary particle size of above-mentioned weighting agent is 5nm, and more preferably the upper limit is 30nm, and further preferred lower limit is 10nm, and further preferred upper limit is 20nm.
It should be noted that, the primary particle size of above-mentioned weighting agent can use NICOMP380ZLS (PARTICLESIZINGSYSTEMS Inc.), above-mentioned weighting agent is scattered in solvent (water, organic solvent etc.) and measures.
In addition, above-mentioned weighting agent sometimes exists with the form of offspring (particle of the multiple gathering of primary particle) in smooth moisture-curable resin combination of the present invention, the preferred lower limit of the particle diameter of such offspring is 5nm, preferred upper limit is 500nm, more preferably lower limit is 10nm, and more preferably the upper limit is 100nm.The particle diameter of the offspring of above-mentioned weighting agent can measure by using transmission electron microscope (TEM) to observe smooth moisture-curable resin combination of the present invention or its cured article.
As above-mentioned weighting agent, preferred inorganic filler, can enumerate such as silicon-dioxide, talcum, titanium oxide, zinc oxide, calcium carbonate etc.Wherein, the aspect of the composition of UV photopermeability excellence is become from the light moisture-curable resin combination of gained, preferred silicon-dioxide.These weighting agents may be used alone, two or more kinds can also be used in combination.
Above-mentioned weighting agent preferably carries out hydrophobic surface treatments and forms.By above-mentioned hydrophobic surface treatments, the light moisture-curable resin combination of gained becomes the more excellent composition of the shape-holding property after coating.
As above-mentioned hydrophobic surface treatments, silylanizing process, alkylation process, epoxy process etc. can be enumerated.Wherein, from the excellent effect aspect improving shape-holding property, preferred silylanizing process, more preferably trimethylsilylation process.
As the method for above-mentioned weighting agent being carried out to hydrophobic surface treatments, can enumerate such as, use the surface treatment agents such as silane coupling agent to process the method etc. on the surface of weighting agent.
Specifically such as, above-mentioned trimethylsilylation process silicon-dioxide can wait to make by the following method, such as, utilizes the method synthetic silicas such as sol-gel method, the method for hexamethyldisilazane of spraying under the state making silica flow; In the organic solvent such as alcohol, toluene, add silicon-dioxide, add hexamethyldisilazane and water further, then utilize evaporimeter to make the method etc. of water and organic solvent evaporation drying.
In all 100 weight parts of smooth moisture-curable resin combination of the present invention, the preferred lower limit of the content of above-mentioned weighting agent is 0.1 weight part, and preferred upper limit is 20 weight parts.If the content of above-mentioned weighting agent is less than 0.1 weight part, then the shape-holding property after the coating of the light moisture-curable resin combination of gained is sometimes poor.If the content of above-mentioned weighting agent is greater than 20 weight parts, then the coating of the light moisture-curable resin combination of gained is poor sometimes.More preferably the lower limit of the content of above-mentioned weighting agent is 0.5 weight part, and more preferably the upper limit is 15 weight parts, and further preferred lower limit is 1 weight part, and further preferred upper limit is 12 weight parts, and particularly preferably lower limit is 2 weight parts.
Smooth moisture-curable resin combination of the present invention can also contain the additives such as ionic liquid, solvent, metallic particle, reactive diluent as required.
As the method manufacturing smooth moisture-curable resin combination of the present invention, mixing machines such as such as using dispersed machine, homogeneous mixer, universal mixer, planetary mixer, kneader, three-roller can be enumerated, free-radical polymerised compound, moisture-curable carbamate resins, optical free radical polymerization starter, opalizer and the additive that adds as required are carried out the method etc. mixed.
Smooth moisture-curable resin combination of the present invention by rayed rapid solidification, and then makes its moisture-curable, can solidify fully thus.
It should be noted that, as the light source making to use during smooth moisture-curable resin combination photocuring of the present invention, be not only normally used high voltage mercury lamp, metal halide lamp, the light source of LED mode also can use.
The optical concentration (OD value) of the cured article of the 1mm thickness after smooth moisture-curable resin combination preferred consolidation of the present invention is more than 1.If above-mentioned OD value is less than 1, then opacifying property becomes insufficient sometimes, for there is spilling of light during display element, cannot obtain high-contrast.Above-mentioned OD value is more preferably more than 1.5.
Above-mentioned OD value is more high better, if raising above-mentioned OD value and coordinate opalizer too in large quantities, then can there is the reduction etc. of the operability caused due to thickening, therefore, in order to obtain the balance with the use level of opalizer, the preferred upper limit of the OD value of above-mentioned cured body is 4.
It should be noted that, the OD value after the solidification of above-mentioned smooth moisture-curable resin combination can use optical concentration meter to measure.The cured article measuring above-mentioned OD value can irradiate 500mJ/cm by using high voltage mercury lamp etc.
2ultraviolet and obtain.
Smooth moisture-curable resin combination of the present invention, use cone plate type viscometer 25 DEG C, the preferred lower limit of viscosity that records under the condition of 1rpm is 50Pas, preferred upper limit is 500Pas.If above-mentioned viscosity is less than 50Pas or is greater than 500Pas, then when sometimes light moisture-curable resin combination being used for electronic component-use caking agent, display element caking agent, operability when coating the adherends such as substrate is deteriorated.More preferably the lower limit of above-mentioned viscosity is 80Pas, and more preferably the upper limit is 300Pas, and further preferred upper limit is 200Pas.
The preferred lower limit of the thixotropy index of smooth moisture-curable resin combination of the present invention is 1.3, and preferred upper limit is 5.0.If above-mentioned thixotropy index is less than 1.3 or be greater than 5.0, then when sometimes light moisture-curable resin combination being used for electronic component-use caking agent, display element caking agent, operability when coating the adherends such as substrate is deteriorated.More preferably the lower limit of above-mentioned thixotropy index is 1.5, and more preferably the upper limit is 4.0.
It should be noted that, in this manual, above-mentioned thixotropy index refers to, use cone plate type viscometer 25 DEG C, the viscosity that records under the condition of 1rpm is divided by using cone plate type viscometer 25 DEG C, the viscosity that records under the condition of 10rpm and the value that obtains.
Smooth moisture-curable resin combination of the present invention particularly preferably can use as electronic component-use caking agent, display element caking agent.Use smooth moisture-curable resin combination of the present invention and the electronic component-use caking agent made and the display element caking agent that uses smooth moisture-curable resin combination of the present invention and make also are one of the present invention respectively.
Invention effect
According to the present invention, opacifying property and light moisture-curable resin combination excellent in adhesion can be provided.
Accompanying drawing explanation
Fig. 1 (a) is schematic diagram when representing the sample for evaluation from top view cementability, and Fig. 1 (b) represents the schematic diagram during sample for evaluation from horizontal observation cementability.
Embodiment
Below enumerate embodiment to be described in detail further to the present invention, but the present invention is not limited to these embodiments.In addition, according to the present invention, can provide and use this light moisture-curable resin combination and the electronic component-use caking agent made and display element caking agent.
(synthesis example 1 (making of carbamate prepolymer A))
Using polytetramethylene ether diol (Mitsubishi Chemical Ind's system of 100 weight parts as polyvalent alcohol, " PTMG-2000 ") and the dibutyl tin laurate of 0.01 weight part be added in the separable flask of 500mL capacity, under vacuo (below 20mmHg), stir 30 minutes and mix at 100 DEG C.Be set to normal pressure subsequently, add the PureMDI (Cao Itochu system) of 26.5 weight parts as vulcabond, within 3 hours, make it react 80 DEG C of stirrings, obtain carbamate prepolymer A (weight-average molecular weight 2700).
(synthesis example 2 (making of carbamate prepolymer B))
Using polypropylene glycol (the Asahi Glass Inc. of 100 weight parts as polyvalent alcohol, " EXCENOL2020 ") and the dibutyl tin laurate of 0.01 weight part be added to the separable flask of 500mL capacity, under vacuo (below 20mmHg), stir 30 minutes at 100 DEG C and mix.Be set to normal pressure subsequently, add the PureMDI (Cao Itochu system) of 26.5 weight parts as vulcabond, within 3 hours, make it react 80 DEG C of stirrings, obtain carbamate prepolymer B (weight-average molecular weight 2900).
(synthesis example 3 (making of carbamate prepolymer C))
To operate in the same manner as synthesis example 1 and in the reaction vessel of the carbamate prepolymer A obtained adding; add hydroxyethyl methylacrylate 1.3 weight part, as the N-nitrosophenylhydroxylamine aluminium salt of stopper (with light pure pharmaceutical worker's industry Inc.; " Q-1301 ") O.14 weight part; be uniformly mixed 1 hour under nitrogen flowing, at 80 DEG C, obtain the carbamate prepolymer C (weight-average molecular weight 3100) in molecular end with isocyanate group and methacryloyl.
(embodiment 1 ~ 16, comparative example 1,2)
According to the proportioning recorded in table 1,2, utilize planetary whipping appts (Thinky Inc., " ぁ ゎ と り Practice Taro ") by after each material stirring, utilize ceramic three-roller Homogeneous phase mixing, thus obtain the light moisture-curable resin combination of embodiment 1 ~ 16, comparative example 1,2.
It should be noted that; " carbamate prepolymer A " in table 1 is the carbamate prepolymer recording, have at two ends isocyanate group in synthesis example 1; " carbamate prepolymer B " is the carbamate prepolymer recording, have at two ends isocyanate group in synthesis example 2, and " carbamate prepolymer C " is the carbamate prepolymer recording, have in molecular end isocyanate group and methacryloyl in synthesis example 3.
< evaluates >
Following evaluation has been carried out for each smooth moisture-curable resin combination obtained in embodiment and comparative example.Show the result in table 1,2.
(opacifying property (OD value))
The each smooth moisture-curable resin combination obtained in embodiment and comparative example is coated Teflon (registered trademark) small pieces of 1mm thickness as on the demoulding polyethylene terephthalate (PET) of interval dose, further overlapping demoulding PET thereon, glass is utilized to extrude and form uniform thickness, then by using high voltage mercury lamp radiation 500mJ/cm
2ultraviolet, thus make light moisture-curable resin combination carry out photocuring.
Subsequently, make it carry out moisture-curable by placing an evening, thus obtain the opacifying property sample for evaluation of 1mm thickness.
For the opacifying property sample for evaluation of gained, optical concentration meter (X-rite Inc., " spectrometer ") is used to measure optical concentration (OD value).
(cementability)
Use distribution device, by each smooth moisture-curable resin combination obtained in embodiment and comparative example, coat polycarbonate substrate with the width of about 2mn.Subsequently, high voltage mercury lamp radiation 500mJ/cm is used
2ultraviolet, make light moisture-curable resin combination carry out photocuring thus.
Subsequently, sheet glass is fitted in polycarbonate substrate, place an evening, make its moisture-curable thus, thus obtain cementability sample for evaluation.
Illustrate in Fig. 1 and represented from the schematic diagram (Fig. 1 (a)) during top view cementability sample for evaluation and represent from the schematic diagram (Fig. 1 (b)) during horizontal observation cementability sample for evaluation.
Use tensile testing machine, along shear direction with the cementability sample for evaluation made by the speed tensile of 5mm/sec, thus determine intensity when base material is peeled off.
(deep solidified nature)
Use distribution device, by each smooth moisture-curable resin combination obtained in embodiment and comparative example, coat polycarbonate substrate with the width of about 2mm.Subsequently, high voltage mercury lamp radiation 500mJ/cm is used
2ultraviolet, make light moisture-curable resin combination carry out photocuring thus, thus produce deep solidified nature sample for evaluation.With infiltrating non-woven fabrics (the Asahi Chemical Industry's fiber company system having acetone, " Bemcot ") the deep solidified nature sample for evaluation of wiping gained time, overall for the cured article sample (deep solidification does not occur) easily taken off from substrate is evaluated as "×", the sample (deep solidification occurs an a part) cured article part being residued in substrate is evaluated as " △ ", the sample (deep solidification occurs major part) cured article major part residued on substrate is evaluated as "○", the sample (there occurs deep solidification) that can not be taken off from substrate completely by cured article is evaluated as " ◎ ", evaluate deep solidified nature thus.
[table 1]
[table 2]
Utilizability in industry
According to the present invention, opacifying property and light moisture-curable resin combination excellent in adhesion can be provided.In addition, according to the present invention, can provide and use this light moisture-curable resin combination and the electronic component-use caking agent made and display element caking agent.
Nomenclature
1 polycarbonate resin substrate
2 smooth moisture-curable resin combinations
3 sheet glass
Claims (8)
1. a light moisture-curable resin combination, is characterized in that, containing free-radical polymerised compound, moisture-curable carbamate resins, optical free radical polymerization starter and opalizer.
2. smooth moisture-curable resin combination according to claim 1, is characterized in that, the OD value of the cured article that the 1mm after solidification is thick is more than 1.
3. smooth moisture-curable resin combination according to claim 1 and 2, is characterized in that, free-radical polymerised compound contains monofunctional free radical's polymerizable compound and multifunctional free-radical polymerised compound.
4. the light moisture-curable resin combination according to any one of claims 1 to 3, is characterized in that, containing sensitizing agent.
5. the light moisture-curable resin combination according to any one of Claims 1 to 4, is characterized in that, optical free radical polymerization starter is acylphosphine oxide based compound.
6. the light moisture-curable resin combination according to any one of Claims 1 to 5, is characterized in that, is the weighting agent of 1 ~ 50nm containing primary particle size.
7. an electronic component-use caking agent, is characterized in that, uses the light moisture-curable resin combination according to any one of claim 1 ~ 6 to make.
8. a display element caking agent, is characterized in that, uses the light moisture-curable resin combination according to any one of claim 1 ~ 6 to make.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111283440.9A CN113801623A (en) | 2014-01-21 | 2015-01-20 | Adhesive for electronic component and adhesive for display element |
| CN202210318888.8A CN114702631A (en) | 2014-01-21 | 2015-01-20 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014-008733 | 2014-01-21 | ||
| JP2014008733 | 2014-01-21 | ||
| PCT/JP2015/051354 WO2015111570A1 (en) | 2014-01-21 | 2015-01-20 | Light/moisture-curable resin composition, adhesive for electronic components, and adhesive for display elements |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111283440.9A Division CN113801623A (en) | 2014-01-21 | 2015-01-20 | Adhesive for electronic component and adhesive for display element |
| CN202210318888.8A Division CN114702631A (en) | 2014-01-21 | 2015-01-20 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
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| CN105473631A true CN105473631A (en) | 2016-04-06 |
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| CN201580001617.8A Pending CN105473631A (en) | 2014-01-21 | 2015-01-20 | Light/moisture-curable resin composition, adhesive for electronic components, and adhesive for display elements |
| CN202111283440.9A Pending CN113801623A (en) | 2014-01-21 | 2015-01-20 | Adhesive for electronic component and adhesive for display element |
| CN202210318888.8A Pending CN114702631A (en) | 2014-01-21 | 2015-01-20 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
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| CN202111283440.9A Pending CN113801623A (en) | 2014-01-21 | 2015-01-20 | Adhesive for electronic component and adhesive for display element |
| CN202210318888.8A Pending CN114702631A (en) | 2014-01-21 | 2015-01-20 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
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| JP (2) | JP5845377B1 (en) |
| KR (2) | KR102242601B1 (en) |
| CN (3) | CN105473631A (en) |
| TW (1) | TWI655219B (en) |
| WO (1) | WO2015111570A1 (en) |
Cited By (2)
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| CN110105530A (en) * | 2019-05-10 | 2019-08-09 | 广州回天新材料有限公司 | A kind of UV moisture double cured resin preparation method |
| CN115353810A (en) * | 2022-09-08 | 2022-11-18 | 杭州之江有机硅化工有限公司 | UV and moisture dual-curing adhesive and preparation method and application thereof |
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| WO2015190499A1 (en) * | 2014-06-11 | 2015-12-17 | 積水化学工業株式会社 | Photo/moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
| JP6510788B2 (en) * | 2014-10-03 | 2019-05-08 | 積水化学工業株式会社 | Light moisture curable resin composition |
| WO2023153514A1 (en) * | 2022-02-14 | 2023-08-17 | 積水化学工業株式会社 | Photo/moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN113801623A (en) | 2021-12-17 |
| KR20160111322A (en) | 2016-09-26 |
| KR20210045503A (en) | 2021-04-26 |
| TWI655219B (en) | 2019-04-01 |
| JPWO2015111570A1 (en) | 2017-03-23 |
| JP2016028171A (en) | 2016-02-25 |
| CN114702631A (en) | 2022-07-05 |
| WO2015111570A1 (en) | 2015-07-30 |
| KR102242601B1 (en) | 2021-04-20 |
| JP6434890B2 (en) | 2018-12-05 |
| KR102372448B1 (en) | 2022-03-08 |
| JP5845377B1 (en) | 2016-01-20 |
| TW201533080A (en) | 2015-09-01 |
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Application publication date: 20160406 |