WO2015111567A1 - 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
- WO2015111567A1 WO2015111567A1 PCT/JP2015/051348 JP2015051348W WO2015111567A1 WO 2015111567 A1 WO2015111567 A1 WO 2015111567A1 JP 2015051348 W JP2015051348 W JP 2015051348W WO 2015111567 A1 WO2015111567 A1 WO 2015111567A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- moisture
- meth
- light
- curable resin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 93
- 239000000853 adhesive Substances 0.000 title claims abstract description 28
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 32
- 230000003287 optical effect Effects 0.000 claims description 29
- 239000000945 filler Substances 0.000 claims description 21
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 18
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 17
- 239000011164 primary particle Substances 0.000 claims description 11
- 238000003860 storage Methods 0.000 abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 89
- -1 polymeric MDI Chemical compound 0.000 description 55
- 239000003822 epoxy resin Substances 0.000 description 34
- 229920000647 polyepoxide Polymers 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 32
- 229920005862 polyol Polymers 0.000 description 29
- 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 25
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 20
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 18
- 150000003077 polyols Chemical class 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004843 novolac epoxy resin Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
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- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 235000011187 glycerol Nutrition 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
- 150000002513 isocyanates Chemical class 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000009974 thixotropic effect Effects 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 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 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000013008 moisture curing Methods 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 229920001610 polycaprolactone Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000011163 secondary particle Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 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 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 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 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
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 2
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 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
- 239000007983 Tris buffer Substances 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- 230000008901 benefit Effects 0.000 description 2
- JFKWZVQEMSKSBU-UHFFFAOYSA-N benzyl 2-hydroxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(O)C(=O)OCC1=CC=CC=C1 JFKWZVQEMSKSBU-UHFFFAOYSA-N 0.000 description 2
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
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- 239000006229 carbon black Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 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 2
- 239000000203 mixture Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
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- 230000008569 process Effects 0.000 description 2
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
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- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([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])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- 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
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- C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/24—Catalysts containing metal compounds of tin
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- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- 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
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- 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
- C08G18/70—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
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
Definitions
- the present invention relates to a light moisture curable resin composition excellent in storage stability and adhesiveness. Moreover, this invention relates to the adhesive agent for electronic components and the adhesive agent for display elements which use this optical moisture hardening type resin composition.
- liquid crystal display elements In recent years, liquid crystal display elements, organic EL display elements, and the like are widely used as display elements having features such as thinness, light weight, and low power consumption.
- a photocurable resin composition is usually used for sealing a liquid crystal or a light emitting layer, bonding a substrate, an optical film, a protective film, or various members.
- a frame is being made (hereinafter also referred to as a narrow frame design).
- a photocurable resin composition may be applied to a portion where light does not reach sufficiently, and as a result, the photocurable resin composition applied to a portion where light does not reach is cured.
- a photothermosetting resin composition is used as a resin composition that can be sufficiently cured even when applied to a portion where light does not reach, and photocuring and thermosetting are also used in combination. There was a possibility of adversely affecting the elements and the like by heating.
- Patent Document 1 discloses a light containing a urethane prepolymer having at least one isocyanate group and at least one (meth) acryloyl group in the molecule.
- a method of using a moisture curable resin composition in combination with photocuring and moisture curing is disclosed.
- the light moisture curable resin composition as disclosed in Patent Document 1 has a problem that it is difficult to achieve both storage stability and adhesiveness.
- An object of the present invention is to provide a light moisture curable resin composition excellent in storage stability and adhesiveness. Another object of the present invention is to provide an adhesive for electronic parts and an adhesive for display elements using the light moisture curable resin composition.
- the present invention is an optical moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, a radical photopolymerization initiator, and a moisture removing agent.
- the present invention is described in detail below.
- the inventors of the present invention can preserve storage stability and adhesiveness by blending a light moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator with a moisture removing agent.
- the inventors have found that both of the above can be improved and have completed the present invention.
- the light moisture curable resin composition of the present invention contains a moisture removing agent.
- the moisture removing agent is not particularly limited, and examples thereof include those due to physical adsorption and those that chemically react with moisture.
- a compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group is suitably used.
- the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group has high reactivity with moisture, and the reaction between moisture-curable urethane resin and moisture during storage Has a role to prevent.
- the compound which has a urethane bond and an isocyanate group is handled as the said moisture hardening type urethane resin.
- the molecular weight is preferably small.
- the preferable upper limit of the molecular weight is 500, and the more preferable upper limit is 300. From the viewpoint of effectively removing moisture by increasing the reaction rate with moisture, compounds having an isocyanate group having an aromatic ring or an isothiocyanate group having an aromatic ring are preferred.
- the compound which has a carbodiimide group there is no restriction
- the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group that did not react with moisture contributes to the curing of the moisture-curable urethane resin, and has a crosslinking density.
- the cured product of the resulting optical moisture curable resin composition is excellent in adhesiveness.
- the minimum with the preferable molecular weight of the compound which has at least 1 sort (s) selected from the group which consists of the said isocyanate group, an isothiocyanate group, and a carbodiimide group is 100, and a more preferable minimum is 150.
- compounds having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group compounds having an isocyanate group are preferred.
- the compound similar to the polyisocyanate compound used as the raw material of the moisture curable urethane resin mentioned later may be sufficient, and may differ.
- the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group may be monofunctional or polyfunctional, It is preferable that it is bifunctional because it has moderate reactivity.
- the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group is for chemically removing moisture, but the light moisture curable type of the present invention.
- the compound having an isocyanate group specifically includes, for example, isophorone diisocyanate, 2, 4 -Tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate (NDI) , Norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris ( Isocyanatophenyl) thiophosphate, tetramethylxylene diis
- the compound having an isothiocyanate group specifically includes, for example, benzyl isothiocyanate, phenyl Examples include isothiocyanate, 4-phenylbutyl isothiocyanate, and 3-phenylpropyl isothiocyanate.
- the compound having a carbodiimide group specifically includes, for example, N, N-dicyclohexylcarbodiimide.
- Carbodilite LA-1 (Nisshinbo Co., Ltd.) and the like can be mentioned.
- the compound which has an isocyanate group is preferable from improving the crosslinking density and being excellent in the effect which makes the hardened
- These compounds having at least one group selected from the group consisting of isocyanate group, isothiocyanate group, and carbodiimide group may be used alone or in combination of two or more. .
- moisture removing agent other moisture removing agents other than the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group may be used.
- the other water removing agent include boron oxide, calcium oxide, magnesium oxide, chromium oxide, manganese oxide, iron oxide, copper oxide, silver oxide, indium oxide, barium oxide, lead oxide, phosphorus oxide, strontium oxide, Metal oxides such as activated alumina, metal sulfates such as magnesium sulfate, sodium sulfate and nickel sulfate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal hydrides, and aluminum oxide octylates Organometallic compounds, zeolite compounds, hydrotalcite compounds, silica gel, alumino silica gel, sodium dithionite, monovalent or polyhydric carboxylic acid anhydrides, acrylates, carbohydrazides, ascor
- These other moisture removing agents may be used alone or in combination of two or more. These other water removing agents may be used in combination with a compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group.
- the content of the moisture removing agent is preferably 0.05 parts by weight with a preferred lower limit and 10 parts by weight with respect to 100 parts by weight of the entire light moisture curable resin composition of the present invention.
- the content of the moisture removing agent is less than 0.05 parts by weight, the resulting light moisture curable resin composition may be inferior in storage stability and adhesiveness.
- the content of the moisture removing agent exceeds 10 parts by weight, the degree of cross-linking during curing of the moisture-curing urethane resin may be excessively increased, and may become hard and brittle.
- the more preferable lower limit of the content of the water removing agent is 0.1 parts by weight
- the more preferable upper limit is 5.0 parts by weight
- the still more preferable lower limit is 0.2 parts by weight
- the still more preferable upper limit is 3.0 parts by weight.
- the upper limit is 1.5 parts by weight.
- the light moisture curable resin composition of the present invention contains a radically polymerizable compound.
- the radical polymerizable compound is not particularly limited as long as it is a compound having a radical reactive functional group in the molecule, but a compound having an unsaturated double bond as the radical reactive functional group is suitable, and particularly reactive.
- a resin having a (meth) acryloyl group (hereinafter, also referred to as “(meth) acrylic resin”) is preferable.
- the “(meth) acryloyl group” means an acryloyl group or a methacryloyl group
- the “(meth) acryl” means acryl or methacryl.
- Examples of the (meth) acrylic resin include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy (meta) obtained by reacting (meth) acrylic acid with an epoxy compound.
- the “(meth) acrylate” means acrylate or methacrylate.
- Examples of the monofunctional compounds of the ester compounds include phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, various imide acrylates, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, Isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (Meth) acrylate, tetrahydrofurfuryl (me
- bifunctional ester compound examples include 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth).
- ester compound having three or more functional groups examples include pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, and ethylene oxide-added trimethylol.
- Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
- Examples of the epoxy compound as a raw material for synthesizing the epoxy (meth) acrylate include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 2,2′-diallyl bisphenol A type epoxy resin. , Hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol Novolac epoxy resin, orthocresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin, naphtha Ren phenol novolak type epoxy resin, glycidyl amine type epoxy resin, alkyl polyol type epoxy resin, rubber modified epoxy resin, glycidyl ester compounds, bisphenol A type episulfide resins.
- Examples of commercially available bisphenol A type epoxy resins include jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation), Epicron 850-S (manufactured by DIC Corporation), and the like.
- As what is marketed among the said bisphenol F-type epoxy resins jER806, jER4004 (all are the Mitsubishi Chemical company make) etc. are mentioned, for example.
- As what is marketed among the said bisphenol S-type epoxy resins, Epicron EXA1514 (made by DIC Corporation) etc. are mentioned, for example.
- Examples of commercially available 2,2′-diallylbisphenol A type epoxy resins include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
- Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
- Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
- Examples of commercially available naphthalene type epoxy resins include Epicron HP4032, Epicron EXA-4700 (both manufactured by DIC) and the like.
- Examples of commercially available phenol novolac epoxy resins include Epicron N-770 (manufactured by DIC).
- Examples of the ortho-cresol novolac type epoxy resin that are commercially available include epiclone N-670-EXP-S (manufactured by DIC).
- Examples of commercially available glycidylamine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical), Epicron 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical).
- Examples of commercially available alkyl polyol type epoxy resins include ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiklon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX-611. (Manufactured by Nagase ChemteX Corporation).
- Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolide PB (manufactured by Daicel Corporation), and the like.
- Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
- Examples of commercially available bisphenol A type episulfide resins include jERYL-7000 (manufactured by Mitsubishi Chemical Corporation).
- epoxy resins include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by NS Also, Mitsubishi Chemical Corporation), EXA-7120 (DIC Corporation), TEPIC (Nissan Chemical Corporation) and the like.
- Examples of commercially available epoxy (meth) acrylates include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRY370R ), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, Epoxy ester 200PA, Epoxy ester 80MF Epoxy ester 3002M, Epoxy ester 3002A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A, Epoxy ester 200EA, Epoxy ester 400EA (all manufactured by Kyoeisha Chemical Co., Ltd.), Denacol acrylate DA-141, Denacol acrylate DA-3
- the urethane (meth) acrylate is obtained, for example, by reacting 2 equivalents of a (meth) acrylic acid derivative having a hydroxyl group with 1 equivalent of a compound having two isocyanate groups in the presence of a catalytic amount of a tin-based compound. be able to.
- Examples of the isocyanate used as a raw material for the urethane (meth) acrylate include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4 ′.
- MDI Diisocyanate
- XDI xylylene diisocyanate
- XDI hydrogenated XDI
- lysine diisocyanate triphenylmethane triisocyanate
- Isocyanatephenyl tris (Isocyanatephenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6,11-undecane triisocyanate Doors and the like.
- isocyanate examples include, for example, a reaction between a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
- a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
- a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
- the resulting chain-extended isocyanate compound
- Examples of the (meth) acrylic acid derivative having a hydroxyl group, which is a raw material of the urethane (meth) acrylate include, for example, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, and 1,4-butane.
- Examples include epoxy (meth) acrylates such as epoxy (meth) acrylate.
- Examples of commercially available urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (both manufactured by Daicel Orunekusu, Inc.
- radical polymerizable compounds other than those described above can be used as appropriate.
- the other radical polymerizable compounds include N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, Examples include (meth) acrylamide compounds such as N-isopropyl (meth) acrylamide and N, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as styrene, ⁇ -methylstyrene, N-pyropidone, and N-vinylcaprolactone. .
- the radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting curability.
- a monofunctional radical polymerizable compound When only a monofunctional radically polymerizable compound is used, the resulting light moisture curable resin composition may be inferior in curability, and when only a polyfunctional radically polymerizable compound is used, the resulting light moisture cured
- the mold resin composition may be inferior in tackiness.
- the polyfunctional radically polymerizable compound is preferably bifunctional or trifunctional, and more preferably bifunctional.
- the radical polymerizable compound contains the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound
- the content of the polyfunctional radical polymerizable compound is the same as the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound.
- a preferable lower limit is 2 parts by weight and a preferable upper limit is 30 parts by weight with respect to a total of 100 parts by weight with the functional radical polymerizable compound.
- the content of the polyfunctional radically polymerizable compound is less than 2 parts by weight, the resulting light moisture curable resin composition may be inferior in curability.
- content of the said polyfunctional radically polymerizable compound exceeds 30 weight part, the optical moisture hardening type resin composition obtained may become inferior to tackiness.
- the minimum with more preferable content of the said polyfunctional radically polymerizable compound is 5 weight part, and a more preferable upper limit is 20 weight part.
- the optical moisture curable resin composition of the present invention contains a moisture curable urethane resin.
- the isocyanate group in the molecule is cured by reacting with moisture in the air or in the adherend.
- the obtained optical moisture hardening type resin composition is excellent in quick-curing property.
- the moisture curable urethane resin may have only one isocyanate group in one molecule, or may have two or more. Of these, urethane prepolymers having isocyanate groups at both ends are preferred.
- the urethane prepolymer can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
- polyol compound the well-known polyol compound normally used for manufacture of a polyurethane can be used, For example, polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol etc. are mentioned. These polyol compounds may be used independently and may be used in combination of 2 or more type.
- polyester polyol examples include a polyester polyol obtained by a reaction between a polyvalent carboxylic acid and a polyol, and a poly- ⁇ -caprolactone polyol obtained by ring-opening polymerization of ⁇ -caprolactone.
- polyvalent carboxylic acid used as a raw material for the polyester polyol examples include terephthalic acid, isophthalic acid, 1,5-naphthalic acid, 2,6-naphthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, and suberin.
- examples include acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, dodecamethylene dicarboxylic acid and the like.
- polyester polyol examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, and 1,6-hexane.
- Diol, diethylene glycol, cyclohexanediol, etc. are mentioned.
- polyether polyol examples include ring-opening polymers of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran, random copolymers or block copolymers of these and their derivatives, and bisphenol-type polyoxy An alkylene modified body etc. are mentioned.
- the modified bisphenol-type polyoxyalkylene is a polyether polyol obtained by addition reaction of alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to the active hydrogen portion of the bisphenol-type molecular skeleton, A random copolymer or a block copolymer may be used.
- the modified bisphenol-type polyoxyalkylene preferably has one or more alkylene oxides added to both ends of the bisphenol-type molecular skeleton. It does not specifically limit as a bisphenol type, A type, F type, S type etc. are mentioned, Preferably it is bisphenol A type.
- polyalkylene polyol examples include polybutadiene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.
- polycarbonate polyol examples include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.
- polyisocyanate compound examples include diphenylmethane diisocyanate, a liquid modified product of diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like.
- diphenylmethane diisocyanate and its modified products are preferred from the viewpoint of low vapor pressure, low toxicity, and ease of handling.
- the said polyisocyanate compound may be used independently and may be used in combination of 2 or more type.
- the said moisture hardening type urethane resin is obtained using the polyol compound which has a structure represented by following formula (1).
- a polyol compound having a structure represented by the following formula (1) it is possible to obtain a composition excellent in adhesiveness and a cured product that is flexible and has good elongation, and is compatible with the radical polymerizable compound. It will be excellent.
- a polyether polyol composed of a ring-opening polymerization compound of propylene glycol, a tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group.
- R represents hydrogen, a methyl group, or an ethyl group
- n is an integer of 1 to 10
- L is an integer of 0 to 5
- m is an integer of 1 to 500.
- n is preferably 1 to 5
- L is preferably 0 to 4
- m is preferably 50 to 200.
- L is 0 means the case where carbon bonded to R is directly bonded to oxygen.
- the moisture curable urethane resin may have a radical polymerizable functional group.
- the radical polymerizable functional group that the moisture curable urethane resin may have is preferably a group having an unsaturated double bond, and more preferably a (meth) acryloyl group from the viewpoint of reactivity.
- the moisture curable urethane resin having a radical polymerizable functional group is not included in the radical polymerizable compound and is treated as a moisture curable urethane resin.
- the preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 800, and the preferable upper limit is 10,000.
- the weight average molecular weight of the moisture curable urethane resin is less than 800, the crosslink density increases and flexibility may be impaired.
- the weight average molecular weight of the moisture curable urethane resin exceeds 10,000, the resulting light moisture curable resin composition may have poor applicability.
- the more preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 3000, and the more preferable upper limit is 6000.
- the said weight average molecular weight is a value calculated
- GPC gel permeation chromatography
- Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK). Moreover, tetrahydrofuran etc. are mentioned as a solvent used by GPC.
- the content of the moisture curable urethane resin is preferably 20 parts by weight with a preferred lower limit and 90 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable urethane resin.
- the resulting optical moisture curable resin composition may be inferior in moisture curable property. If the content of the moisture curable urethane resin exceeds 90 parts by weight, the resulting light moisture curable resin composition may be inferior in photocurability.
- a more preferable lower limit of the content of the moisture curable urethane resin is 30 parts by weight, a more preferable upper limit is 75 parts by weight, a still more preferable lower limit is 41 parts by weight, and a still more preferable upper limit is 70 parts by weight.
- the light moisture curable resin composition of the present invention contains a radical photopolymerization initiator.
- the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthones, and the like.
- Examples of commercially available photoradical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACUREOXE01, and Benzylin TPO from Benzylin SPO Benzoin ethyl ether, benzoin isopropyl ether (both manufactured by Tokyo Chemical Industry Co., Ltd.) and the like.
- the content of the photo radical polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the radical polymerizable compound.
- the content of the radical photopolymerization initiator is less than 0.01 part by weight, the resulting light moisture curable resin composition may not be sufficiently photocured.
- content of the said radical photopolymerization initiator exceeds 10 weight part, the storage stability of the obtained optical moisture hardening type resin composition may fall.
- the minimum with more preferable content of the said radical photopolymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.
- the light moisture curable resin composition of the present invention may contain a light shielding agent.
- the optical moisture hardening type resin composition of this invention becomes the thing excellent in light-shielding property, and can prevent the light leak of a display element.
- the “light-shielding agent” means a material having an ability of hardly transmitting light in the visible light region.
- the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Further, the light-shielding agent does not have to be black, and a material such as silica or talc, which will be described later as a filler, may be used as long as it has a capability of hardly transmitting light in the visible light region. Included in the agent. Of these, titanium black is preferable.
- Titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly for light having a wavelength of 370 to 450 nm, compared to the average transmittance for light having a wavelength of 300 to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby imparting light shielding properties to the light moisture curable resin composition of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region. Is a light-shielding agent.
- the light of the photo moisture curable resin composition of the present invention can be used. Curability can be further increased.
- the light-shielding agent contained in the light moisture curable resin composition of the present invention is preferably a highly insulating material, and titanium black is also preferable as the highly insulating light-shielding agent.
- the titanium black preferably has an optical density (OD value) of 3 or more, and more preferably 4 or more.
- the titanium black preferably has a blackness (L value) of 9 or more, more preferably 11 or more. The higher the light shielding property of the titanium black, the better. There is no particular upper limit to the OD value of the titanium black, but it is usually 5 or less.
- the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
- the display element manufactured using the light moisture curable resin composition of the present invention has a high contrast because there is no light leakage because the light moisture curable resin composition has sufficient light shielding properties. Image display quality.
- titanium black examples include 12S, 13M, 13M-C, 13R-N (all manufactured by Mitsubishi Materials Corporation), Tilak D (manufactured by Ako Kasei Co., Ltd.), and the like.
- the preferable lower limit of the specific surface area of the titanium black is 5 m 2 / g, the preferable upper limit is 40 m 2 / g, the more preferable lower limit is 10 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
- the preferable lower limit of the sheet resistance of the titanium black is 10 9 ⁇ / ⁇ when mixed with a resin (70% blending), and the more preferable lower limit is 10 11 ⁇ / ⁇ .
- the preferable lower limit of the volume resistance of the titanium black is 0.5 ⁇ ⁇ cm, the preferable upper limit is 3 ⁇ ⁇ cm, the more preferable lower limit is 1 ⁇ ⁇ cm, and the more preferable upper limit is 2.5 ⁇ ⁇ cm.
- the primary particle diameter of the light-shielding agent is appropriately selected depending on the application, such as the distance between the substrates of the display element, but the preferable lower limit is 30 nm and the preferable upper limit is 500 nm. It is. When the primary particle diameter of the light-shielding agent is less than 30 nm, the viscosity and thixotropy of the obtained light moisture-curable resin composition are greatly increased, and workability may be deteriorated.
- the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the obtained light moisture curable resin composition may be lowered, and the light-shielding property may be lowered.
- the more preferable lower limit of the primary particle diameter of the light shielding agent is 50 nm, and the more preferable upper limit is 200 nm.
- a preferable minimum is 0.05 weight% and a preferable upper limit is 10 weight%. If the content of the light shielding agent is less than 0.05% by weight, sufficient light shielding properties may not be obtained. When the content of the light-shielding agent is more than 10% by weight, the adhesiveness of the obtained light moisture curable resin composition to the substrate or the strength after curing may be lowered, or the drawing property may be lowered.
- the more preferable lower limit of the content of the light shielding agent is 0.1% by weight, the more preferable upper limit is 2% by weight, the still more preferable lower limit is 0.3% by weight, and the still more preferable upper limit is 1% by weight.
- the light moisture curable resin composition of the present invention may contain a filler from the viewpoint of adjusting the applicability and shape retention of the resulting light moisture curable resin composition.
- the light moisture curable resin composition of the present invention has suitable thixotropy and can sufficiently retain the shape after coating.
- the filler preferably has a primary particle diameter with a preferred lower limit of 1 nm and a preferred upper limit of 50 nm.
- the primary particle diameter of the filler is less than 1 nm, the resulting light moisture curable resin composition may be inferior in applicability.
- the primary particle diameter of the filler exceeds 50 nm, the resulting light moisture curable resin composition may be inferior in shape retention after coating.
- the more preferable lower limit of the primary particle diameter of the filler is 5 nm, the more preferable upper limit is 30 nm, the still more preferable lower limit is 10 nm, and the still more preferable upper limit is 20 nm.
- the primary particle size of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
- the filler may be present as secondary particles (a collection of a plurality of primary particles) in the light moisture curable resin composition of the present invention, and the preferred lower limit of the particle diameter of such secondary particles. Is 5 nm, the preferred upper limit is 500 nm, the more preferred lower limit is 10 nm, and the more preferred upper limit is 100 nm.
- the particle diameter of the secondary particles of the filler can be measured by observing the optical moisture curable resin composition of the present invention or a cured product thereof using a transmission electron microscope (TEM).
- TEM transmission electron microscope
- an inorganic filler is preferable and a silica, a talc, etc. are mentioned, for example.
- silica is preferable because the obtained light moisture curable resin composition is excellent in UV light transmittance.
- These fillers may be used independently and may be used in combination of 2 or more type.
- the filler is preferably subjected to a hydrophobic surface treatment.
- a hydrophobic surface treatment By the hydrophobic surface treatment, the resulting optical moisture curable resin composition is more excellent in shape retention after application.
- the hydrophobic surface treatment include silylation treatment, alkylation treatment, and epoxidation treatment. Especially, since it is excellent in the effect which improves shape retainability, a silylation process is preferable and a trimethylsilylation process is more preferable.
- Examples of the method for treating the filler with a hydrophobic surface include a method for treating the surface of the filler with a surface treatment agent such as a silane coupling agent.
- a surface treatment agent such as a silane coupling agent.
- the trimethylsilylated silica is prepared by, for example, synthesizing silica by a method such as a sol-gel method and spraying hexamethyldisilazane in a state where the silica is fluidized, or an organic solvent such as alcohol or toluene. It can be produced by a method in which silica is added, hexamethyldisilazane and water are added, and then water and an organic solvent are evaporated and dried with an evaporator.
- the content of the filler is preferably 0.1 parts by weight with a preferable lower limit and 20 parts by weight with respect to 100 parts by weight of the entire optical moisture-curable resin composition of the present invention.
- the content of the filler is less than 0.1 parts by weight, the obtained light moisture curable resin composition may be inferior in shape retention after coating.
- content of the said filler exceeds 20 weight part, the optical moisture hardening type resin composition obtained may become inferior to applicability
- the more preferred lower limit of the content of the filler is 0.5 parts by weight, the more preferred upper limit is 15 parts by weight, the still more preferred lower limit is 1 part by weight, the still more preferred upper limit is 12 parts by weight, and the particularly preferred lower limit is 2 parts by weight. It is.
- the light moisture curable resin composition of the present invention may further contain additives such as an ionic liquid, a solvent, metal-containing particles, and a reactive diluent as necessary.
- a method for producing the light moisture curable resin composition of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three roll, And a method of mixing a moisture curable urethane resin, a radical photopolymerization initiator, a moisture removing agent, and an additive to be added as necessary.
- a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three roll, And a method of mixing a moisture curable urethane resin, a radical photopolymerization initiator, a moisture removing agent, and an additive to be added as necessary.
- the moisture content of the light moisture curable resin composition of the present invention is 100 ppm or less.
- the moisture content exceeds 100 ppm, the moisture-curable urethane resin and moisture easily react during storage, and the optical moisture-curable resin composition is inferior in storage stability.
- the water content is more preferably 80 ppm or less. The water content can be measured by a Karl Fischer moisture measuring device.
- the preferable lower limit of the viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer is 50 Pa ⁇ s
- the preferable upper limit is 500 Pa ⁇ s.
- the viscosity is less than 50 Pa ⁇ s or more than 500 Pa ⁇ s
- the light moisture curable resin composition is applied to an adherend such as a substrate when used as an adhesive for electronic parts or an adhesive for display elements. The workability when doing so may deteriorate.
- a more preferred lower limit of the viscosity is 80 Pa ⁇ s
- a more preferred upper limit is 300 Pa ⁇ s
- a still more preferred upper limit is 200 Pa ⁇ s.
- the preferable lower limit of the thixotropic index of the light moisture curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0.
- the thixotropic index is less than 1.3 or exceeds 5.0, an adherend such as a substrate is used when the optical moisture curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements. The workability at the time of applying to may be deteriorated.
- the more preferable lower limit of the thixotropic index is 1.5, and the more preferable upper limit is 4.0.
- the thixotropic index is a viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer, and measured at 25 ° C. and 10 rpm using a cone plate viscometer. It means the value divided by the viscosity.
- the light moisture curable resin composition of the present invention can be particularly suitably used as an adhesive for electronic parts or an adhesive for display elements.
- An adhesive for electronic components using the light moisture curable resin composition of the present invention and a display element adhesive using the light moisture curable resin composition of the present invention are also included in the present invention. It is.
- the optical moisture hardening type resin composition excellent in storage stability and adhesiveness can be provided.
- (A) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the top
- (b) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the side.
- the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples. Moreover, according to this invention, the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.
- Examples 1 to 19 Comparative Examples 1 and 2
- each material was stirred with a planetary stirrer (manufactured by Shinky Co., Ltd., “Awatori Netaro”) and then mixed uniformly with a ceramic three roll.
- the optical moisture curable resin compositions of Examples 1 to 19 and Comparative Examples 1 and 2 were obtained.
- “urethane prepolymer A” is a urethane prepolymer having an isocyanate group at both ends described in Synthesis Example 1
- urethane prepolymer B is both ends described in Synthesis Example 2.
- the “urethane prepolymer C” is a urethane prepolymer having an isocyanate group and a methacryloyl group at the molecular end described in Synthesis Example 3.
- FIG. 1 is a schematic diagram (FIG. 1 (a)) showing a case where an adhesive evaluation sample is viewed from above, and a schematic diagram showing a case where the adhesive evaluation sample is viewed from the side (FIG. 1 (b)). showed that.
- the produced adhesive evaluation sample was pulled at a rate of 5 mm / sec in the shear direction using a tensile tester, and the strength when the substrate was peeled was measured.
- the optical moisture hardening type resin composition excellent in storage stability and adhesiveness can be provided.
- the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.
Abstract
Description
ところで、携帯電話、携帯ゲーム機等、各種表示素子付きモバイル機器が普及している現代において、表示素子の小型化は最も求められている課題であり、小型化の手法として、画像表示部を狭額縁化することが行われている(以下、狭額縁設計ともいう)。しかしながら、狭額縁設計においては、充分に光の届かない部分に光硬化型樹脂組成物が塗布されることがあり、その結果、光の届かない部分に塗布された光硬化型樹脂組成物は硬化が不充分となるという問題があった。そこで、光の届かない部分に塗布された場合でも充分に硬化できる樹脂組成物として光熱硬化型樹脂組成物を用い、光硬化と熱硬化とを併用することも行われているが、高温での加熱により素子等に悪影響を与えるおそれがあった。 In recent years, liquid crystal display elements, organic EL display elements, and the like are widely used as display elements having features such as thinness, light weight, and low power consumption. In these display elements, a photocurable resin composition is usually used for sealing a liquid crystal or a light emitting layer, bonding a substrate, an optical film, a protective film, or various members.
By the way, in the present age when mobile devices with various display elements such as mobile phones and portable game machines are widespread, downsizing of the display elements is the most demanded issue. A frame is being made (hereinafter also referred to as a narrow frame design). However, in a narrow frame design, a photocurable resin composition may be applied to a portion where light does not reach sufficiently, and as a result, the photocurable resin composition applied to a portion where light does not reach is cured. There was a problem that was insufficient. Therefore, a photothermosetting resin composition is used as a resin composition that can be sufficiently cured even when applied to a portion where light does not reach, and photocuring and thermosetting are also used in combination. There was a possibility of adversely affecting the elements and the like by heating.
以下に本発明を詳述する。 The present invention is an optical moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, a radical photopolymerization initiator, and a moisture removing agent.
The present invention is described in detail below.
上記水分除去剤は特に限定されず、物理的な吸着によるものや、化学的に水分と反応するもの等が挙げられる。 The light moisture curable resin composition of the present invention contains a moisture removing agent.
The moisture removing agent is not particularly limited, and examples thereof include those due to physical adsorption and those that chemically react with moisture.
また、上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物の分子量の好ましい下限は100、より好ましい下限は150である。 When using a compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group as the moisture removing agent, it is necessary to move through the system and react with moisture quickly. Therefore, the molecular weight is preferably small. Particularly, in the case of a compound having an isocyanate group or an isothiocyanate group, the preferable upper limit of the molecular weight is 500, and the more preferable upper limit is 300. From the viewpoint of effectively removing moisture by increasing the reaction rate with moisture, compounds having an isocyanate group having an aromatic ring or an isothiocyanate group having an aromatic ring are preferred. In addition, there is no restriction | limiting in particular in the compound which has a carbodiimide group. The compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group that did not react with moisture contributes to the curing of the moisture-curable urethane resin, and has a crosslinking density. As a result, the cured product of the resulting optical moisture curable resin composition is excellent in adhesiveness.
Moreover, the minimum with the preferable molecular weight of the compound which has at least 1 sort (s) selected from the group which consists of the said isocyanate group, an isothiocyanate group, and a carbodiimide group is 100, and a more preferable minimum is 150.
上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物は、単官能であってもよいし、多官能であってもよいが、水分に対して適度な反応性を有することから2官能であることが好ましい。
なお、上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物は、化学的に水分を除去するものであるが、本発明の光湿気硬化型樹脂組成物に使用する各材料を配合する前に、予め、必要に応じて、各材料に物理的な処理(後述するゼオライトのような他の水分除去剤による水分の除去)を行っておいてもよい。 Of the compounds having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group, compounds having an isocyanate group are preferred. When using the compound which has an isocyanate group as said moisture removal agent, the compound similar to the polyisocyanate compound used as the raw material of the moisture curable urethane resin mentioned later may be sufficient, and may differ.
The compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group may be monofunctional or polyfunctional, It is preferable that it is bifunctional because it has moderate reactivity.
The compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group is for chemically removing moisture, but the light moisture curable type of the present invention. Before blending each material to be used in the resin composition, if necessary, physical treatment (removal of water with other moisture removing agent such as zeolite described later) is performed on each material in advance. Also good.
上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物のうち、イソチオシアネート基を有する化合物としては、具体的には例えば、ベンジルイソチオシアネート、フェニルイソチオシアネート、4-フェニルブチルイソチオシアネート、3-フェニルプロピルイソチオシアネート等が挙げられる。
上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物のうち、カルボジイミド基を有する化合物としては、具体的には例えば、N,N-ジシクロヘキシルカルボジイミド、N,N-ジイソプロピルカルボジイミド、1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩、ビス(2,6-ジイソプロピルフェニル)カルボジイミド等が挙げられ、市販されているものとしては、例えば、カルボジライトLA-1(日清紡社製)等が挙げられる。
なかでも、架橋密度を向上させ、得られる光湿気硬化型樹脂組成物の硬化物を接着性に優れるものとする効果に優れることから、イソシアネート基を有する化合物が好ましい。これらのイソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物は、単独で用いられてもよいし、2種以上を組み合わせて用いられてもよい。 Among the compounds having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group, the compound having an isocyanate group specifically includes, for example, isophorone diisocyanate, 2, 4 -Tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate (NDI) , Norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris ( Isocyanatophenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6,11-undecane triisocyanate and the like.
Among the compounds having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group, the compound having an isothiocyanate group specifically includes, for example, benzyl isothiocyanate, phenyl Examples include isothiocyanate, 4-phenylbutyl isothiocyanate, and 3-phenylpropyl isothiocyanate.
Of the compounds having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group, the compound having a carbodiimide group specifically includes, for example, N, N-dicyclohexylcarbodiimide. , N, N-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, and the like. Carbodilite LA-1 (Nisshinbo Co., Ltd.) and the like can be mentioned.
Especially, the compound which has an isocyanate group is preferable from improving the crosslinking density and being excellent in the effect which makes the hardened | cured material of the obtained optical moisture-curable resin composition excellent in adhesiveness. These compounds having at least one group selected from the group consisting of isocyanate group, isothiocyanate group, and carbodiimide group may be used alone or in combination of two or more. .
これらの他の水分除去剤は、単独で用いてもよいし、2種以上を組み合わせて用いてもよい。また、これらの他の水分除去剤は、上記イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物と組み合わせて用いてもよい。 Further, as the moisture removing agent, other moisture removing agents other than the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group may be used. Examples of the other water removing agent include boron oxide, calcium oxide, magnesium oxide, chromium oxide, manganese oxide, iron oxide, copper oxide, silver oxide, indium oxide, barium oxide, lead oxide, phosphorus oxide, strontium oxide, Metal oxides such as activated alumina, metal sulfates such as magnesium sulfate, sodium sulfate and nickel sulfate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal hydrides, and aluminum oxide octylates Organometallic compounds, zeolite compounds, hydrotalcite compounds, silica gel, alumino silica gel, sodium dithionite, monovalent or polyhydric carboxylic acid anhydrides, acrylates, carbohydrazides, ascorbates, gallic acid, Alkoxysilane, carbon nanotube, activated carbon, cell Over scan powder.
These other moisture removing agents may be used alone or in combination of two or more. These other water removing agents may be used in combination with a compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group.
上記ラジカル重合性化合物としては、分子中にラジカル反応性官能基を有する化合物であれば特に限定されないが、ラジカル反応性官能基として不飽和二重結合を有する化合物が好適であり、特に反応性の面から(メタ)アクリロイル基を有する樹脂(以下、「(メタ)アクリル樹脂」ともいう)が好適である。
なお、本明細書において、上記「(メタ)アクリロイル基」は、アクリロイル基又はメタクリロイル基を意味し、上記「(メタ)アクリル」は、アクリル又はメタクリルを意味する。 The light moisture curable resin composition of the present invention contains a radically polymerizable compound.
The radical polymerizable compound is not particularly limited as long as it is a compound having a radical reactive functional group in the molecule, but a compound having an unsaturated double bond as the radical reactive functional group is suitable, and particularly reactive. From the surface, a resin having a (meth) acryloyl group (hereinafter, also referred to as “(meth) acrylic resin”) is preferable.
In the present specification, the “(meth) acryloyl group” means an acryloyl group or a methacryloyl group, and the “(meth) acryl” means acryl or methacryl.
なお、本明細書において、上記「(メタ)アクリレート」とは、アクリレート又はメタクリレートを意味する。 Examples of the (meth) acrylic resin include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy (meta) obtained by reacting (meth) acrylic acid with an epoxy compound. ) Urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with acrylate or isocyanate.
In the present specification, the “(meth) acrylate” means acrylate or methacrylate.
上記ビスフェノールF型エポキシ樹脂のうち市販されているものとしては、例えば、jER806、jER4004(いずれも三菱化学社製)等が挙げられる。
上記ビスフェノールS型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンEXA1514(DIC社製)等が挙げられる。
上記2,2’-ジアリルビスフェノールA型エポキシ樹脂のうち市販されているものとしては、例えば、RE-810NM(日本化薬社製)等が挙げられる。
上記水添ビスフェノール型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンEXA7015(DIC社製)等が挙げられる。
上記プロピレンオキシド付加ビスフェノールA型エポキシ樹脂のうち市販されているものとしては、例えば、EP-4000S(ADEKA社製)等が挙げられる。
上記レゾルシノール型エポキシ樹脂のうち市販されているものとしては、例えば、EX-201(ナガセケムテックス社製)等が挙げられる。
上記ビフェニル型エポキシ樹脂のうち市販されているものとしては、例えば、jERYX-4000H(三菱化学社製)等が挙げられる。
上記スルフィド型エポキシ樹脂のうち市販されているものとしては、例えば、YSLV-50TE(新日鉄住金化学社製)等が挙げられる。
上記ジフェニルエーテル型エポキシ樹脂のうち市販されているものとしては、例えば、YSLV-80DE(新日鉄住金化学社製)等が挙げられる。
上記ジシクロペンタジエン型エポキシ樹脂のうち市販されているものとしては、例えば、EP-4088S(ADEKA社製)等が挙げられる。
上記ナフタレン型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンHP4032、エピクロンEXA-4700(いずれもDIC社製)等が挙げられる。
上記フェノールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンN-770(DIC社製)等が挙げられる。
上記オルトクレゾールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンN-670-EXP-S(DIC社製)等が挙げられる。
上記ジシクロペンタジエンノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンHP7200(DIC社製)等が挙げられる。
上記ビフェニルノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、NC-3000P(日本化薬社製)等が挙げられる。
上記ナフタレンフェノールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、ESN-165S(新日鉄住金化学社製)等が挙げられる。
上記グリシジルアミン型エポキシ樹脂のうち市販されているものとしては、例えば、jER630(三菱化学社製)、エピクロン430(DIC社製)、TETRAD-X(三菱ガス化学社製)等が挙げられる。
上記アルキルポリオール型エポキシ樹脂のうち市販されているものとしては、例えば、ZX-1542(新日鉄住金化学社製)、エピクロン726(DIC社製)、エポライト80MFA(共栄社化学社製)、デナコールEX-611(ナガセケムテックス社製)等が挙げられる。
上記ゴム変性型エポキシ樹脂のうち市販されているものとしては、例えば、YR-450、YR-207(いずれも新日鉄住金化学社製)、エポリードPB(ダイセル社製)等が挙げられる。
上記グリシジルエステル化合物のうち市販されているものとしては、例えば、デナコールEX-147(ナガセケムテックス社製)等が挙げられる。
上記ビスフェノールA型エピスルフィド樹脂のうち市販されているものとしては、例えば、jERYL-7000(三菱化学社製)等が挙げられる。
上記エポキシ樹脂のうちその他に市販されているものとしては、例えば、YDC-1312、YSLV-80XY、YSLV-90CR(いずれも新日鉄住金化学社製)、XAC4151(旭化成社製)、jER1031、jER1032(いずれも三菱化学社製)、EXA-7120(DIC社製)、TEPIC(日産化学社製)等が挙げられる。 Examples of commercially available bisphenol A type epoxy resins include jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation), Epicron 850-S (manufactured by DIC Corporation), and the like.
As what is marketed among the said bisphenol F-type epoxy resins, jER806, jER4004 (all are the Mitsubishi Chemical company make) etc. are mentioned, for example.
As what is marketed among the said bisphenol S-type epoxy resins, Epicron EXA1514 (made by DIC Corporation) etc. are mentioned, for example.
Examples of commercially available 2,2′-diallylbisphenol A type epoxy resins include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
As what is marketed among the said hydrogenated bisphenol type | mold epoxy resins, Epicron EXA7015 (made by DIC Corporation) etc. are mentioned, for example.
Examples of commercially available propylene oxide-added bisphenol A type epoxy resins include EP-4000S (manufactured by ADEKA).
Examples of commercially available resorcinol type epoxy resins include EX-201 (manufactured by Nagase ChemteX Corporation).
Examples of commercially available biphenyl type epoxy resins include jERYX-4000H (manufactured by Mitsubishi Chemical Corporation).
Examples of commercially available sulfide type epoxy resins include YSLV-50TE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
Examples of commercially available naphthalene type epoxy resins include Epicron HP4032, Epicron EXA-4700 (both manufactured by DIC) and the like.
Examples of commercially available phenol novolac epoxy resins include Epicron N-770 (manufactured by DIC).
Examples of the ortho-cresol novolac type epoxy resin that are commercially available include epiclone N-670-EXP-S (manufactured by DIC).
As what is marketed among the said dicyclopentadiene novolak-type epoxy resins, epiclone HP7200 (made by DIC) etc. are mentioned, for example.
Examples of commercially available biphenyl novolac epoxy resins include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
Examples of commercially available naphthalene phenol novolac type epoxy resins include ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
Examples of commercially available glycidylamine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical), Epicron 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical).
Examples of commercially available alkyl polyol type epoxy resins include ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiklon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX-611. (Manufactured by Nagase ChemteX Corporation).
Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolide PB (manufactured by Daicel Corporation), and the like.
Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
Examples of commercially available bisphenol A type episulfide resins include jERYL-7000 (manufactured by Mitsubishi Chemical Corporation).
Other commercially available epoxy resins include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by NS Also, Mitsubishi Chemical Corporation), EXA-7120 (DIC Corporation), TEPIC (Nissan Chemical Corporation) and the like.
上記その他のラジカル重合性化合物としては、例えば、N,N-ジメチル(メタ)アクリルアミド、N-(メタ)アクロイルモルホリン、N-ヒドロキシエチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、N,N-ジメチルアミノプロピル(メタ)アクリルアミド等の(メタ)アクリルアミド化合物、スチレン、α-メチルスチレン、N-ピロピドン、N-ビニルカプロラクトン等のビニル化合物等が挙げられる。 In addition, other radical polymerizable compounds other than those described above can be used as appropriate.
Examples of the other radical polymerizable compounds include N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, Examples include (meth) acrylamide compounds such as N-isopropyl (meth) acrylamide and N, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as styrene, α-methylstyrene, N-pyropidone, and N-vinylcaprolactone. .
上記ウレタンプレポリマーは、1分子中に2個以上の水酸基を有するポリオール化合物と、1分子中に2個以上のイソシアネート基を有するポリイソシアネート化合物とを反応させることにより、得ることができる。 The moisture curable urethane resin may have only one isocyanate group in one molecule, or may have two or more. Of these, urethane prepolymers having isocyanate groups at both ends are preferred.
The urethane prepolymer can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
上記ビスフェノール型のポリオキシアルキレン変性体は、ビスフェノール型分子骨格の両末端に、1種又は2種以上のアルキレンオキシドが付加されていることが好ましい。ビスフェノール型としては特に限定されず、A型、F型、S型等が挙げられ、好ましくはビスフェノールA型である。 The modified bisphenol-type polyoxyalkylene is a polyether polyol obtained by addition reaction of alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to the active hydrogen portion of the bisphenol-type molecular skeleton, A random copolymer or a block copolymer may be used.
The modified bisphenol-type polyoxyalkylene preferably has one or more alkylene oxides added to both ends of the bisphenol-type molecular skeleton. It does not specifically limit as a bisphenol type, A type, F type, S type etc. are mentioned, Preferably it is bisphenol A type.
なかでも、プロピレングリコールや、テトラヒドロフラン(THF)化合物の開環重合化合物や、メチル基等の置換基を有するテトラヒドロフラン化合物の開環重合化合物からなるポリエーテルポリオールを用いることが好ましい。 Moreover, it is preferable that the said moisture hardening type urethane resin is obtained using the polyol compound which has a structure represented by following formula (1). By using a polyol compound having a structure represented by the following formula (1), it is possible to obtain a composition excellent in adhesiveness and a cured product that is flexible and has good elongation, and is compatible with the radical polymerizable compound. It will be excellent.
Among these, it is preferable to use a polyether polyol composed of a ring-opening polymerization compound of propylene glycol, a tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group.
なお、Lが0の場合とは、Rと結合した炭素が直接酸素と結合している場合を意味する。 In the formula (1), R represents hydrogen, a methyl group, or an ethyl group, n is an integer of 1 to 10, L is an integer of 0 to 5, and m is an integer of 1 to 500. n is preferably 1 to 5, L is preferably 0 to 4, and m is preferably 50 to 200.
The case where L is 0 means the case where carbon bonded to R is directly bonded to oxygen.
上記湿気硬化型ウレタン樹脂が有していてもよいラジカル重合性官能基としては、不飽和二重結合を有する基が好ましく、特に反応性の面から(メタ)アクリロイル基がより好ましい。
なお、ラジカル重合性官能基を有する湿気硬化型ウレタン樹脂は、ラジカル重合性化合物には含まず、湿気硬化型ウレタン樹脂として扱う。 Furthermore, the moisture curable urethane resin may have a radical polymerizable functional group.
The radical polymerizable functional group that the moisture curable urethane resin may have is preferably a group having an unsaturated double bond, and more preferably a (meth) acryloyl group from the viewpoint of reactivity.
The moisture curable urethane resin having a radical polymerizable functional group is not included in the radical polymerizable compound and is treated as a moisture curable urethane resin.
なお、本明細書において上記重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)で測定を行い、ポリスチレン換算により求められる値である。GPCによってポリスチレン換算による重量平均分子量を測定する際のカラムとしては、例えば、Shodex LF-804(昭和電工社製)等が挙げられる。また、GPCで用いる溶媒としては、テトラヒドロフラン等が挙げられる。 The preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 800, and the preferable upper limit is 10,000. When the weight average molecular weight of the moisture curable urethane resin is less than 800, the crosslink density increases and flexibility may be impaired. When the weight average molecular weight of the moisture curable urethane resin exceeds 10,000, the resulting light moisture curable resin composition may have poor applicability. The more preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 3000, and the more preferable upper limit is 6000.
In addition, the said weight average molecular weight is a value calculated | required by polystyrene conversion by measuring with a gel permeation chromatography (GPC) in this specification. Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK). Moreover, tetrahydrofuran etc. are mentioned as a solvent used by GPC.
上記光ラジカル重合開始剤としては、例えば、ベンゾフェノン系化合物、アセトフェノン系化合物、アシルフォスフィンオキサイド系化合物、チタノセン系化合物、オキシムエステル系化合物、ベンゾインエーテル系化合物、チオキサントン等が挙げられる。 The light moisture curable resin composition of the present invention contains a radical photopolymerization initiator.
Examples of the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthones, and the like.
なお、本明細書において、上記「遮光剤」は、可視光領域の光を透過させ難い能力を有する材料を意味する。 The light moisture curable resin composition of the present invention may contain a light shielding agent. By containing the said light-shielding agent, the optical moisture hardening type resin composition of this invention becomes the thing excellent in light-shielding property, and can prevent the light leak of a display element.
In the present specification, the “light-shielding agent” means a material having an ability of hardly transmitting light in the visible light region.
上記チタンブラックは、光学濃度(OD値)が、3以上であることが好ましく、4以上であることがより好ましい。また、上記チタンブラックは、黒色度(L値)が9以上であることが好ましく、11以上であることがより好ましい。上記チタンブラックの遮光性は高ければ高いほど良く、上記チタンブラックのOD値に好ましい上限は特に無いが、通常は5以下となる。 Titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly for light having a wavelength of 370 to 450 nm, compared to the average transmittance for light having a wavelength of 300 to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby imparting light shielding properties to the light moisture curable resin composition of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region. Is a light-shielding agent. Therefore, by using a photo radical polymerization initiator that can initiate a reaction with light having a wavelength (370 to 450 nm) at which the transmittance of titanium black is high, the light of the photo moisture curable resin composition of the present invention can be used. Curability can be further increased. On the other hand, the light-shielding agent contained in the light moisture curable resin composition of the present invention is preferably a highly insulating material, and titanium black is also preferable as the highly insulating light-shielding agent.
The titanium black preferably has an optical density (OD value) of 3 or more, and more preferably 4 or more. The titanium black preferably has a blackness (L value) of 9 or more, more preferably 11 or more. The higher the light shielding property of the titanium black, the better. There is no particular upper limit to the OD value of the titanium black, but it is usually 5 or less.
また、本発明の光湿気硬化型樹脂組成物を用いて製造した表示素子は、光湿気硬化型樹脂組成物が充分な遮光性を有するため、光の漏れ出しがなく高いコントラストを有し、優れた画像表示品質を有するものとなる。 The above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
In addition, the display element manufactured using the light moisture curable resin composition of the present invention has a high contrast because there is no light leakage because the light moisture curable resin composition has sufficient light shielding properties. Image display quality.
また、上記チタンブラックのシート抵抗の好ましい下限は、樹脂と混合された場合(70%配合)において、109Ω/□であり、より好ましい下限は1011Ω/□である。
更に、上記チタンブラックの体積抵抗の好ましい下限は0.5Ω・cm、好ましい上限は3Ω・cmであり、より好ましい下限は1Ω・cm、より好ましい上限は2.5Ω・cmである。 The preferable lower limit of the specific surface area of the titanium black is 5 m 2 / g, the preferable upper limit is 40 m 2 / g, the more preferable lower limit is 10 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
Moreover, the preferable lower limit of the sheet resistance of the titanium black is 10 9 Ω / □ when mixed with a resin (70% blending), and the more preferable lower limit is 10 11 Ω / □.
Furthermore, the preferable lower limit of the volume resistance of the titanium black is 0.5 Ω · cm, the preferable upper limit is 3 Ω · cm, the more preferable lower limit is 1 Ω · cm, and the more preferable upper limit is 2.5 Ω · cm.
なお、上記充填剤の一次粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)を用いて、上記充填剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
また、上記充填剤は、本発明の光湿気硬化型樹脂組成物中において二次粒子(一次粒子が複数集まったもの)として存在する場合があり、このような二次粒子の粒子径の好ましい下限は5nm、好ましい上限は500nm、より好ましい下限は10nm、より好ましい上限は100nmである。上記充填剤の二次粒子の粒子径は、本発明の光湿気硬化型樹脂組成物又はその硬化物を、透過型電子顕微鏡(TEM)を用いて観察することにより測定することができる。 The filler preferably has a primary particle diameter with a preferred lower limit of 1 nm and a preferred upper limit of 50 nm. When the primary particle diameter of the filler is less than 1 nm, the resulting light moisture curable resin composition may be inferior in applicability. When the primary particle diameter of the filler exceeds 50 nm, the resulting light moisture curable resin composition may be inferior in shape retention after coating. The more preferable lower limit of the primary particle diameter of the filler is 5 nm, the more preferable upper limit is 30 nm, the still more preferable lower limit is 10 nm, and the still more preferable upper limit is 20 nm.
The primary particle size of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
In addition, the filler may be present as secondary particles (a collection of a plurality of primary particles) in the light moisture curable resin composition of the present invention, and the preferred lower limit of the particle diameter of such secondary particles. Is 5 nm, the preferred upper limit is 500 nm, the more preferred lower limit is 10 nm, and the more preferred upper limit is 100 nm. The particle diameter of the secondary particles of the filler can be measured by observing the optical moisture curable resin composition of the present invention or a cured product thereof using a transmission electron microscope (TEM).
上記疎水性表面処理としては、シリル化処理、アルキル化処理、エポキシ化処理等が挙げられる。なかでも、形状保持性を向上させる効果に優れることから、シリル化処理が好ましく、トリメチルシリル化処理がより好ましい。 The filler is preferably subjected to a hydrophobic surface treatment. By the hydrophobic surface treatment, the resulting optical moisture curable resin composition is more excellent in shape retention after application.
Examples of the hydrophobic surface treatment include silylation treatment, alkylation treatment, and epoxidation treatment. Especially, since it is excellent in the effect which improves shape retainability, a silylation process is preferable and a trimethylsilylation process is more preferable.
具体的には例えば、上記トリメチルシリル化処理シリカは、例えば、シリカをゾルゲル法等の方法で合成し、シリカを流動させた状態でヘキサメチルジシラザンを噴霧する方法や、アルコール、トルエン等の有機溶媒中にシリカを加え、更に、ヘキサメチルジシラザンと水とを加えた後、水と有機溶媒とをエバポレーターで蒸発乾燥させる方法等により作製することができる。 Examples of the method for treating the filler with a hydrophobic surface include a method for treating the surface of the filler with a surface treatment agent such as a silane coupling agent.
Specifically, for example, the trimethylsilylated silica is prepared by, for example, synthesizing silica by a method such as a sol-gel method and spraying hexamethyldisilazane in a state where the silica is fluidized, or an organic solvent such as alcohol or toluene. It can be produced by a method in which silica is added, hexamethyldisilazane and water are added, and then water and an organic solvent are evaporated and dried with an evaporator.
なお、上記水分量は、カールフィッシャー水分測定装置により測定することができる。 It is preferable that the moisture content of the light moisture curable resin composition of the present invention is 100 ppm or less. When the moisture content exceeds 100 ppm, the moisture-curable urethane resin and moisture easily react during storage, and the optical moisture-curable resin composition is inferior in storage stability. The water content is more preferably 80 ppm or less.
The water content can be measured by a Karl Fischer moisture measuring device.
なお、本明細書において上記チクソトロピックインデックスとは、コーンプレート型粘度計を用いて25℃、1rpmの条件で測定した粘度を、コーンプレート型粘度計を用いて25℃、10rpmの条件で測定した粘度で除した値を意味する。 The preferable lower limit of the thixotropic index of the light moisture curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0. When the thixotropic index is less than 1.3 or exceeds 5.0, an adherend such as a substrate is used when the optical moisture curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements. The workability at the time of applying to may be deteriorated. The more preferable lower limit of the thixotropic index is 1.5, and the more preferable upper limit is 4.0.
In the present specification, the thixotropic index is a viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer, and measured at 25 ° C. and 10 rpm using a cone plate viscometer. It means the value divided by the viscosity.
ポリオールとして100重量部のポリテトラメチレンエーテルグリコール(三菱化学社製、「PTMG-2000」)と、0.01重量部のジブチル錫ジラウレートとを500mL容のセパラブルフラスコに入れ、真空下(20mmHg以下)、100℃で30分間撹拌し、混合した。その後常圧とし、ジイソシアネートとして26.5重量部のPure MDI(日曹商事社製)を入れ、80℃で3時間撹拌し、反応させ、ウレタンプレポリマーA(重量平均分子量2700)を得た。 (Synthesis Example 1 (Production of Urethane Prepolymer A))
100 parts by weight of polytetramethylene ether glycol (“PTMG-2000”, manufactured by Mitsubishi Chemical Corporation) and 0.01 parts by weight of dibutyltin dilaurate were placed in a 500 mL separable flask as a polyol, and under vacuum (20 mmHg or less) ), And stirred at 100 ° C. for 30 minutes and mixed. Thereafter, normal pressure was applied, and 26.5 parts by weight of Pure MDI (manufactured by Nisso Shoji Co., Ltd.) was added as diisocyanate, stirred at 80 ° C. for 3 hours and reacted to obtain urethane prepolymer A (weight average molecular weight 2700).
ポリオールとして100重量部のポリプロピレングリコール(旭硝子社製、「EXCENOL 2020」)と、0.01重量部のジブチル錫ジラウレートとを500mL容のセパラブルフラスコに入れ、真空下(20mmHg以下)、100℃で30分間撹拌し、混合した。その後常圧とし、ジイソシアネートとして26.5重量部のPure MDI(日曹商事社製)を入れ、80℃で3時間撹拌し、反応させ、ウレタンプレポリマーB(重量平均分子量2900)を得た。 (Synthesis Example 2 (Production of Urethane Prepolymer B))
As a polyol, 100 parts by weight of polypropylene glycol (manufactured by Asahi Glass Co., Ltd., “EXCENOL 2020”) and 0.01 part by weight of dibutyltin dilaurate are placed in a 500 mL separable flask, and are placed under vacuum (20 mmHg or less) at 100 ° C. Stir for 30 minutes and mix. Thereafter, normal pressure was applied, and 26.5 parts by weight of Pure MDI (manufactured by Nisso Shoji Co., Ltd.) was added as diisocyanate, stirred at 80 ° C. for 3 hours, and reacted to obtain urethane prepolymer B (weight average molecular weight 2900).
合成例1と同様にして得られたウレタンプレポリマーAの入った反応容器に、ヒドロキシエチルメタクリレート1.3重量部と、重合禁止剤としてN-ニトロソフェニルヒドロキシルアミンアルミニウム塩(和光純薬工業社製、「Q-1301」)0.14重量部とを添加し、窒素気流下、80℃で1時間撹拌混合して、分子末端にイソシアネート基とメタクリロイル基とを有するウレタンプレポリマーC(重量平均分子量3100)を得た。 (Synthesis Example 3 (Production of Urethane Prepolymer C))
In a reaction vessel containing urethane prepolymer A obtained in the same manner as in Synthesis Example 1, 1.3 parts by weight of hydroxyethyl methacrylate and N-nitrosophenylhydroxylamine aluminum salt as a polymerization inhibitor (manufactured by Wako Pure Chemical Industries, Ltd.) , "Q-1301") 0.14 parts by weight, and stirred and mixed at 80 ° C for 1 hour under a nitrogen stream, and urethane prepolymer C (weight average molecular weight) having an isocyanate group and a methacryloyl group at the molecular end. 3100).
表1、2に記載された配合比に従い、各材料を、遊星式撹拌装置(シンキー社製、「あわとり練太郎」)にて撹拌した後、セラミック3本ロールにて均一に混合して実施例1~19、比較例1、2の光湿気硬化型樹脂組成物を得た。
なお、表1、2における「ウレタンプレポリマーA」は合成例1に記載した、両末端にイソシアネート基を有するウレタンプレポリマーであり、「ウレタンプレポリマーB」は合成例2に記載した、両末端にイソシアネート基を有するウレタンプレポリマーであり、「ウレタンプレポリマーC」は合成例3に記載した、分子末端にイソシアネート基とメタクリロイル基とを有するウレタンプレポリマーである。 (Examples 1 to 19, Comparative Examples 1 and 2)
In accordance with the blending ratios described in Tables 1 and 2, each material was stirred with a planetary stirrer (manufactured by Shinky Co., Ltd., “Awatori Netaro”) and then mixed uniformly with a ceramic three roll. The optical moisture curable resin compositions of Examples 1 to 19 and Comparative Examples 1 and 2 were obtained.
In Tables 1 and 2, “urethane prepolymer A” is a urethane prepolymer having an isocyanate group at both ends described in Synthesis Example 1, and “urethane prepolymer B” is both ends described in Synthesis Example 2. The “urethane prepolymer C” is a urethane prepolymer having an isocyanate group and a methacryloyl group at the molecular end described in Synthesis Example 3.
実施例及び比較例で得られた各光湿気硬化型樹脂組成物について以下の評価を行った。結果を表1、2に示した。 <Evaluation>
The following evaluation was performed about each light moisture hardening type resin composition obtained by the Example and the comparative example. The results are shown in Tables 1 and 2.
実施例及び比較例で得られた各光湿気硬化型樹脂組成物を、25℃で1週間保管したときの粘度と、製造直後の初期粘度とを測定したときの(25℃、1週間保管後の粘度)/(初期粘度)で表される値を粘度変化率とし、粘度変化率が1.1未満であるものを「○」、1.1以上1.5未満であるものを「△」、1.5以上であるものを「×」として保存安定性を評価した。
なお、粘度は、コープレート型粘度計(東機産業社製、「VISCOMETER TV-22」)を用い、25℃において回転速度1rpmの条件で測定した。 (Storage stability)
When each of the light moisture curable resin compositions obtained in Examples and Comparative Examples was stored at 25 ° C. for 1 week and the initial viscosity immediately after production (25 ° C., after storage for 1 week) Viscosity) / (Initial Viscosity) is the rate of change in viscosity, the viscosity change rate being less than 1.1 is “◯”, and the viscosity change rate is 1.1 or more and less than 1.5 “Δ” The storage stability was evaluated with “×” being 1.5 or more.
The viscosity was measured using a coplate viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”) at 25 ° C. and a rotation speed of 1 rpm.
実施例及び比較例で得られた各光湿気硬化型樹脂組成物を脱水溶剤に溶かし、カールフィッシャー水分計(京都電子工業社製、「MKC-610」)にて水分量を測定した。 (amount of water)
Each optical moisture-curable resin composition obtained in the examples and comparative examples was dissolved in a dehydrated solvent, and the moisture content was measured with a Karl Fischer moisture meter (“MKC-610” manufactured by Kyoto Electronics Industry Co., Ltd.).
実施例及び比較例で得られた各光湿気硬化型樹脂組成物を、ディスペンス装置を用いて、ポリカーボネート基板に約2mmの幅で塗布した。その後、高圧水銀ランプを用いて、紫外線を500mJ/cm2照射することによって、光湿気硬化型樹脂組成物を光硬化させた。
その後、ポリカーボネート基板にガラス板を貼り合わせ、一晩放置することにより湿気硬化させて、接着性評価用サンプルを得た。
図1に接着性評価用サンプルを上から見た場合を示す模式図(図1(a))、及び、接着性評価用サンプルを横から見た場合を示す模式図(図1(b))を示した。
作製した接着性評価用サンプルを、引張り試験機を用いて、剪断方向に5mm/secの速度で引張り、基材が剥がれる際の強度を測定した。 (Adhesiveness)
Each optical moisture curable resin composition obtained in Examples and Comparative Examples was applied to a polycarbonate substrate with a width of about 2 mm using a dispensing apparatus. Then, the optical moisture curable resin composition was photocured by irradiating with ultraviolet rays at 500 mJ / cm 2 using a high pressure mercury lamp.
Thereafter, a glass plate was bonded to the polycarbonate substrate and left to stand overnight to cure the moisture, thereby obtaining an adhesive evaluation sample.
FIG. 1 is a schematic diagram (FIG. 1 (a)) showing a case where an adhesive evaluation sample is viewed from above, and a schematic diagram showing a case where the adhesive evaluation sample is viewed from the side (FIG. 1 (b)). showed that.
The produced adhesive evaluation sample was pulled at a rate of 5 mm / sec in the shear direction using a tensile tester, and the strength when the substrate was peeled was measured.
実施例及び比較例で得られた各光湿気硬化型樹脂組成物を、ディスペンス装置を用いて、ポリカーボネート基板に約2mmの幅で塗布した。その後、高圧水銀ランプを用いて、紫外線を500mJ/cm2照射することによって、光湿気硬化型樹脂組成物を光硬化させ、タック性の評価用サンプルを作製した。得られたタック性の評価用サンプルについて、タック試験機(レスカ社製、「TAC-100」)を用いてタック強度を測定した。 (Tackiness)
Each optical moisture curable resin composition obtained in Examples and Comparative Examples was applied to a polycarbonate substrate with a width of about 2 mm using a dispensing apparatus. Then, the optical moisture curing type resin composition was photocured by irradiating ultraviolet rays with 500 mJ / cm 2 using a high pressure mercury lamp, and a sample for evaluating tackiness was produced. The tack strength of the obtained sample for evaluation of tackiness was measured using a tack tester (“TAC-100” manufactured by Reska Co., Ltd.).
2 光湿気硬化型樹脂組成物
3 ガラス板 DESCRIPTION OF
Claims (8)
- ラジカル重合性化合物と、湿気硬化型ウレタン樹脂と、光ラジカル重合開始剤と、水分除去剤とを含有することを特徴とする光湿気硬化型樹脂組成物。 A photo moisture curable resin composition comprising a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a water removing agent.
- 水分除去剤は、イソシアネート基、イソチオシアネート基、及び、カルボジイミド基からなる群より選択される少なくとも1種の基を有する化合物を含有することを特徴とする請求項1記載の光湿気硬化型樹脂組成物。 2. The light moisture curable resin composition according to claim 1, wherein the moisture removing agent contains a compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group. object.
- 含有する水分量が100ppm以下であることを特徴とする請求項1又は2記載の光湿気硬化型樹脂組成物。 The light moisture-curable resin composition according to claim 1 or 2, wherein the moisture content is 100 ppm or less.
- ラジカル重合性化合物は、単官能ラジカル重合性化合物と多官能ラジカル重合性化合物とを含有することを特徴とする請求項1、2又は3記載の光湿気硬化型樹脂組成物。 4. The photo-moisture curable resin composition according to claim 1, wherein the radical polymerizable compound contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound.
- 遮光剤を含有することを特徴とする請求項1、2、3又は4記載の光湿気硬化型樹脂組成物。 The light moisture curable resin composition according to claim 1, 2, 3, or 4, further comprising a light shielding agent.
- 一次粒子径が1~50nmの充填剤を含有することを特徴とする請求項1、2、3、4又は5記載の光湿気硬化型樹脂組成物。 6. The photo-moisture curable resin composition according to claim 1, comprising a filler having a primary particle size of 1 to 50 nm.
- 請求項1、2、3、4、5又は6記載の光湿気硬化型樹脂組成物を用いてなることを特徴とする電子部品用接着剤。 An adhesive for electronic parts, comprising the optical moisture curable resin composition according to claim 1, 2, 3, 4, 5 or 6.
- 請求項1、2、3、4、5又は6記載の光湿気硬化型樹脂組成物を用いてなることを特徴とする表示素子用接着剤。 A light-moisture curable resin composition according to claim 1, 2, 3, 5, or 6.
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Cited By (2)
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WO2018074507A1 (en) * | 2016-10-19 | 2018-04-26 | 積水化学工業株式会社 | Organic el display element sealing agent, and method for producing organic el display element sealing agent |
WO2024009957A1 (en) * | 2022-07-04 | 2024-01-11 | 積水化学工業株式会社 | Light/moisture curable resin composition, cured product, use of light/moisture curable resin composition, and end face protection method |
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KR102528349B1 (en) * | 2021-04-21 | 2023-05-03 | 주식회사 한솔케미칼 | Dual curable resin composition and adhesive for display using the same |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05295064A (en) * | 1992-04-24 | 1993-11-09 | Dainippon Ink & Chem Inc | Moisture-curing polyurethane composition |
JPH0657232A (en) * | 1992-08-05 | 1994-03-01 | Dainippon Printing Co Ltd | Adhesive composition |
JPH0782546A (en) * | 1993-09-17 | 1995-03-28 | Toyo Ink Mfg Co Ltd | Visible-light-curing adhesive |
JP2001261725A (en) * | 2000-03-21 | 2001-09-26 | Showa Highpolymer Co Ltd | Water-reactive optically curable urethane resin composition, resin composition for frp lining, primer resin composition, and method for curing the same |
JP2004018621A (en) * | 2002-06-14 | 2004-01-22 | Nippon Shokubai Co Ltd | Radical-hardenable urethane resin composition |
JP2013503238A (en) * | 2009-08-27 | 2013-01-31 | バイエル・マテリアルサイエンス・リミテッド・ライアビリティ・カンパニー | Aliphatic moisture curable resins, coating compositions and related methods |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1135819A (en) * | 1997-07-18 | 1999-02-09 | Yokohama Rubber Co Ltd:The | Moisture curing type one pack polyurethane resin sealing material composition and its production |
JP2001064543A (en) * | 1999-08-27 | 2001-03-13 | Nippon Shokubai Co Ltd | Resin composition for curable coating material |
JP2001240811A (en) * | 2000-03-01 | 2001-09-04 | Sekisui Chem Co Ltd | Reactive adhesive composition and method of bonding framework member |
EP1834971A1 (en) * | 2006-03-13 | 2007-09-19 | Sika Technology AG | Moisture curable polyurethane composition having good low temperature properties |
JP5228370B2 (en) | 2007-04-27 | 2013-07-03 | 東亞合成株式会社 | One-part moisture-curing urethane hot melt adhesive composition and method of using the same |
EP2322571A1 (en) * | 2009-11-06 | 2011-05-18 | Sika Technology AG | Two component adhesive or sealant composition having an accelerating component |
CN103450817B (en) * | 2012-06-01 | 2017-07-04 | 汉高股份有限公司 | Adhesive composition |
CN103305174B (en) * | 2013-05-24 | 2015-01-21 | 南京林业大学 | Preparation method of light/humidity dual-curing polyurethane hot melt adhesive |
WO2015056717A1 (en) * | 2013-10-18 | 2015-04-23 | 積水化学工業株式会社 | Light/moisture-curable resin composition, adhesive for electronic component, and adhesive for display device |
-
2015
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05295064A (en) * | 1992-04-24 | 1993-11-09 | Dainippon Ink & Chem Inc | Moisture-curing polyurethane composition |
JPH0657232A (en) * | 1992-08-05 | 1994-03-01 | Dainippon Printing Co Ltd | Adhesive composition |
JPH0782546A (en) * | 1993-09-17 | 1995-03-28 | Toyo Ink Mfg Co Ltd | Visible-light-curing adhesive |
JP2001261725A (en) * | 2000-03-21 | 2001-09-26 | Showa Highpolymer Co Ltd | Water-reactive optically curable urethane resin composition, resin composition for frp lining, primer resin composition, and method for curing the same |
JP2004018621A (en) * | 2002-06-14 | 2004-01-22 | Nippon Shokubai Co Ltd | Radical-hardenable urethane resin composition |
JP2013503238A (en) * | 2009-08-27 | 2013-01-31 | バイエル・マテリアルサイエンス・リミテッド・ライアビリティ・カンパニー | Aliphatic moisture curable resins, coating compositions and related methods |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018074507A1 (en) * | 2016-10-19 | 2018-04-26 | 積水化学工業株式会社 | Organic el display element sealing agent, and method for producing organic el display element sealing agent |
JPWO2018074507A1 (en) * | 2016-10-19 | 2018-10-18 | 積水化学工業株式会社 | Sealant for organic EL display element and method for producing sealant for organic EL display element |
JP2019040872A (en) * | 2016-10-19 | 2019-03-14 | 積水化学工業株式会社 | Sealing agent for organic el display element and method for manufacturing the same |
JP6997062B2 (en) | 2016-10-19 | 2022-01-17 | 積水化学工業株式会社 | A method for manufacturing a sealant for an organic EL display element and a sealant for an organic EL display element. |
JP2022037060A (en) * | 2016-10-19 | 2022-03-08 | 積水化学工業株式会社 | Sealing agent for organic el display element and method for manufacturing the same |
WO2024009957A1 (en) * | 2022-07-04 | 2024-01-11 | 積水化学工業株式会社 | Light/moisture curable resin composition, cured product, use of light/moisture curable resin composition, and end face protection method |
Also Published As
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TWI685508B (en) | 2020-02-21 |
JP2016027173A (en) | 2016-02-18 |
JPWO2015111567A1 (en) | 2017-03-23 |
CN111574928A (en) | 2020-08-25 |
KR102245326B1 (en) | 2021-04-27 |
JP5836536B1 (en) | 2015-12-24 |
KR20160111323A (en) | 2016-09-26 |
TW201533079A (en) | 2015-09-01 |
JP6499561B2 (en) | 2019-04-10 |
CN105593247A (en) | 2016-05-18 |
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