WO2015146873A1 - 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 - Google Patents
光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 Download PDFInfo
- Publication number
- WO2015146873A1 WO2015146873A1 PCT/JP2015/058657 JP2015058657W WO2015146873A1 WO 2015146873 A1 WO2015146873 A1 WO 2015146873A1 JP 2015058657 W JP2015058657 W JP 2015058657W WO 2015146873 A1 WO2015146873 A1 WO 2015146873A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- resin composition
- light
- acrylate
- moisture
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 83
- 239000000853 adhesive Substances 0.000 title claims abstract description 37
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 35
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 239000000945 filler Substances 0.000 claims description 20
- 239000007870 radical polymerization initiator Substances 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 6
- 238000013008 moisture curing Methods 0.000 claims description 4
- 239000003999 initiator Substances 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 90
- -1 polyol compound Chemical class 0.000 description 56
- 239000003822 epoxy resin Substances 0.000 description 33
- 229920000647 polyepoxide Polymers 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 32
- 239000004593 Epoxy Substances 0.000 description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 22
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 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 17
- 229920005862 polyol Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- 239000011164 primary particle Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000004843 novolac epoxy resin 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
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 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
- 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
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000004519 manufacturing process Methods 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
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000011163 secondary particle Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 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
- 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 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 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
- 239000000203 mixture Substances 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003553 thiiranes Chemical class 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- OVJHMJJVXOJMBB-UHFFFAOYSA-N 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)N(CCOC(=O)C=C)C(=O)C21 OVJHMJJVXOJMBB-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- CYXLGABBVLIUJZ-UHFFFAOYSA-N 2-(2-hydroxypropoxycarbonyl)benzoic acid Chemical compound CC(O)COC(=O)C1=CC=CC=C1C(O)=O CYXLGABBVLIUJZ-UHFFFAOYSA-N 0.000 description 1
- IEQWWMKDFZUMMU-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CCOC(=O)C=C IEQWWMKDFZUMMU-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- RUVNKAUVVBCURD-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)-3-prop-2-enylphenyl]propan-2-yl]-2-prop-2-enylphenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(CC=C)=CC=1C(C)(C)C(C=C1CC=C)=CC=C1OCC1CO1 RUVNKAUVVBCURD-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 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 1
- 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 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IFUSRXHTTSKNDI-UHFFFAOYSA-N isoindole-1,3-dione prop-2-enoic acid Chemical class C(C=C)(=O)O.C1(C=2C(C(N1)=O)=CC=CC2)=O IFUSRXHTTSKNDI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZCIJAGHWGVCOHJ-UHFFFAOYSA-N naphthalene phenol Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O ZCIJAGHWGVCOHJ-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000000600 sorbitol Substances 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
- 238000003860 storage Methods 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
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011787 zinc oxide 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/7664—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
-
- 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
-
- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Definitions
- the present invention relates to a light moisture curable resin composition excellent in flexibility, adhesiveness, and reliability in a high temperature and high humidity environment. 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 number average molecular weight. Thermosetting adhesives containing 600 to 1000 epoxy compounds are disclosed. However, the thermosetting adhesive as disclosed in Patent Document 1 is not suitable for bonding electronic components that may be damaged by heat.
- Patent Document 2 discloses a light moisture curable resin containing a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator. A method of using a composition and combining photocuring and moisture curing is disclosed.
- the light moisture curable resin composition as disclosed in Patent Document 2 has excellent flexibility, adhesiveness, and reliability (particularly creep resistance) in a high temperature and high humidity environment. It was difficult to do.
- the present invention contains a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator, and the moisture curable urethane resin has a polyoxyalkylene chain which may have a branched chain.
- the urethane resin A in which each alkylene group of the polyoxyalkylene chain has 4 or more carbon atoms, and a polyoxyalkylene chain which may have a branched chain, and the polyoxyalkylene It is a light moisture curable resin composition containing urethane resin B in which the carbon number of each alkylene group of the chain is 3 or less.
- each of the specific polyoxyalkylenes is used as the moisture curable urethane resin.
- 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 has a polyoxyalkylene chain which may have a branched chain, and the urethane resin A in which each alkylene group of the polyoxyalkylene chain has 4 or more carbon atoms, and It contains a urethane resin B having a polyoxyalkylene chain which may have a branched chain, and each alkylene group of the polyoxyalkylene chain having 3 or less carbon atoms.
- the urethane resin A and the urethane resin B in combination as the moisture curable urethane resin the light moisture curable resin composition of the present invention has flexibility, adhesiveness, and high temperature and high humidity environment. It will be excellent in all of the reliability.
- matters common to the urethane resin A and the urethane resin B are described as “moisture-curable urethane resin”.
- 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.
- a polyol compound used as the raw material of the urethane resin A for example, a polyoxyalkylene polyol in which each alkylene group has 4 or more carbon atoms can be used.
- the polyol compound used as the raw material of the urethane resin A may have a branched chain. Moreover, the upper limit with preferable carbon number of each alkylene group of the polyol compound used as the raw material of the said urethane resin A is five.
- the polyoxyalkylene polyol having 4 or more carbon atoms in each alkylene group include polytetramethylene ether glycol, polypentamethylene ether glycol, and polyhexamethylene ether glycol.
- a polyoxyalkylene polyol which may have a branched chain and each alkylene group has 3 or less carbon atoms can be used.
- the polyoxyalkylene polyol which has a branched chain and carbon number of each alkylene group is 3 or less.
- the polyoxyalkylene polyol having a branched chain and each alkylene group having 3 or less carbon atoms include polypropylene glycol and polyoxyethylene polyoxypropylene glycol.
- 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 urethane resin A is 800, and the preferable upper limit is 10,000.
- the weight average molecular weight of the urethane resin A is less than 800, the crosslink density is increased and flexibility may be impaired.
- the weight average molecular weight of the urethane resin A exceeds 10,000, the resulting optical moisture curable resin composition is inferior in coating property, or the crosslinking reaction (moisture curing reaction) does not proceed sufficiently and the curing is poor. Sometimes it becomes.
- the more preferable lower limit of the weight average molecular weight of the urethane resin A is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 2500, and the further 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 preferable lower limit of the weight average molecular weight of the urethane resin B is 800, and the preferable upper limit is 10,000.
- the weight average molecular weight of the urethane resin B is less than 800, the crosslink density increases, and the flexibility may be impaired.
- the weight average molecular weight of the urethane resin B exceeds 10,000, the resulting optical moisture curable resin composition is inferior in coatability or the crosslinking reaction (moisture curing reaction) does not proceed sufficiently, resulting in poor curing.
- the more preferable lower limit of the weight average molecular weight of the urethane resin B is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 2500, and the further preferable upper limit is 6000.
- the content of the urethane resin A is preferably 30 parts by weight and preferably 80 parts by weight with respect to a total of 100 parts by weight of the urethane resin A and the urethane resin B.
- the resulting optical moisture curable resin composition may be inferior in adhesiveness or reliability in a high temperature and high humidity environment.
- content of the said urethane resin A exceeds 80 weight part, the hardened
- the minimum with more preferable content of the said urethane resin A is 40 weight part, and a more preferable upper limit is 60 weight part.
- the content of the entire 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.
- the resulting light moisture curable resin composition may be inferior in photocurability.
- the more preferable lower limit of the content of the entire moisture curable urethane resin is 30 parts by weight, the more preferable upper limit is 75 parts by weight, the still more preferable lower limit is 41 parts by weight, and the still more preferable upper limit is 70 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 radical polymerizable compound having photopolymerizability, and is a compound having a radical reactive functional group in the molecule.
- a compound having a heavy bond is preferable, and a compound having a (meth) acryloyl group (hereinafter also referred to as “(meth) acrylic compound”) is particularly preferable from the viewpoint of reactivity.
- the “(meth) acryloyl” means acryloyl or methacryloyl
- the “(meth) acryl” means acryl or methacryl.
- Examples of the (meth) acrylic compound include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy (meth) acrylic obtained by reacting (meth) acrylic acid with an epoxy compound.
- the “(meth) acrylate” means acrylate or methacrylate.
- all the isocyanate groups of the isocyanate compound used as the raw material of the said urethane (meth) acrylate are used for formation of a urethane bond, and the said urethane (meth) acrylate does not have a residual isocyanate group.
- monofunctional compounds include, for example, phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, various imide acrylates, methyl (meth) acrylate, ethyl (meth) acrylate, and n-propyl (meth).
- n-butyl (meth) acrylate isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) Acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (Meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybut
- bifunctional ester compound examples include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth).
- ester compound having three or more functions examples include trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, and caprolactone.
- 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 compounds 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 can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with a compound having an isocyanate group in the presence of a catalytic amount of a tin-based compound.
- isocyanate compound used as the raw material for the urethane (meth) acrylate examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4.
- MDI '-Diisocyanate
- hydrogenated MDI polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanate) Phenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6,11-undecanetriiso Aneto and the like.
- the isocyanate compound can be obtained, for example, by a reaction between a polyol such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate. Chain-extended isocyanate compounds can also be used.
- a polyol such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
- Chain-extended isocyanate compounds can also be used.
- 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, N -(Meth) acrylamide compounds such as 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 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 materials such as silica, talc, and titanium, which will be described later as fillers, can be used as long as they have a capability of hardly transmitting light in the visible light region. Included in the light shielding 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
- 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 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.
- the particle size of the light-shielding agent can be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
- content of the said light shielding agent in the whole optical moisture hardening type resin composition of this invention is not specifically limited, 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. A more preferable lower limit of the content of the light shielding agent is 0.1% by weight, a more preferable upper limit is 2% by weight, and a 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 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).
- 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.
- 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
- the filler examples include silica, talc, titanium oxide, and zinc oxide.
- 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 1 part by weight at a preferable lower limit and 20 parts by weight at a preferable upper limit in 100 parts by weight of the entire light moisture curable resin composition of the present invention.
- the content of the filler is less than 1 part by weight, the resulting 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 2 parts by weight, the more preferred upper limit is 15 parts by weight, the still more preferred lower limit is 3 parts by weight, the still more preferred upper limit is 10 parts by weight, and the particularly preferred lower limit is 4 parts by weight. .
- 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, 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, and an additive to be added as necessary.
- 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 optical moisture curable resin composition is used as an adherend such as a substrate when used as an adhesive for electronic components 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 preferable lower limit of the tensile modulus at 25 ° C. of the cured product is 0.5 kgf / cm 2
- the preferable upper limit is 8 kgf / cm 2 . If the tensile elastic modulus is less than 0.5 kgf / cm 2, it is too soft, the cohesive force is weak, and the adhesive force may be low. When the tensile elastic modulus exceeds 8 kgf / cm 2 , flexibility may be impaired.
- a more preferred lower limit of the tensile modulus 1 kgf / cm 2, and more preferable upper limit is 6 kgf / cm 2.
- tensile modulus is 50% elongation by pulling the cured product at a speed of 10 mm / min using a tensile tester (for example, “EZ-Graph” manufactured by Shimadzu Corporation). It means the value measured as the force of time.
- 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.
- flexibility, adhesiveness, and the reliability in a high temperature, high humidity environment 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.
- (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.
- FIG. 1 is a schematic diagram (FIG.
- flexibility, adhesiveness, and the reliability in a high temperature, high humidity environment 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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。
このような電子部品の接着に用いられる接着剤として、光硬化型では光が当らない部分が発生し、充分な接着力を得ることができないため、例えば、特許文献1には、数平均分子量が600~1000であるエポキシ化合物を含有する熱硬化型の接着剤が開示されている。しかしながら、特許文献1に開示されているような熱硬化型の接着剤は、熱により損傷する可能性のある電子部品の接着には適さないものであった。
以下に本発明を詳述する。
以下、ウレタン樹脂A及びウレタン樹脂Bに共通する事項については、「湿気硬化型ウレタン樹脂」として記載する。
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。
上記各アルキレン基の炭素数が4以上であるポリオキシアルキレンポリオールとしては、ポリテトラメチレンエーテルグリコール、ポリペンタメチレンエーテルグリコール、ポリヘキサメチレンエーテルグリコール等が挙げられる。
上記分岐鎖を有し、かつ、各アルキレン基の炭素数が3以下であるポリオキシアルキレンポリオールとしては、ポリプロピレングリコール、ポリオキシエチレンポリオキシプロピレングリコール等が挙げられる。
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。
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。
上記ラジカル重合性化合物としては、光重合性を有するラジカル重合性化合物であればよく、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化合物(以下、「(メタ)アクリル化合物」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」は、アクリロイル又はメタクリロイルを意味し、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。
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。また、上記ウレタン(メタ)アクリレートの原料となるイソシアネート化合物のイソシアネート基は、全てウレタン結合の形成に用いられ、上記ウレタン(メタ)アクリレートは、残存イソシアネート基を有さない。
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。
上記エポキシ化合物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。
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)アクリロイルモルホリン、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や、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。
また、上記多官能ラジカル重合性化合物は、2官能又は3官能であることが好ましく、2官能であることがより好ましい。
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。
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。
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。
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。
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。
なお、上記遮光剤の粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)を用いて、上記遮光剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
上記充填剤は、一次粒子径の好ましい下限が1nm、好ましい上限が50nmである。上記充填剤の一次粒子径が1nm未満であると、得られる光湿気硬化型樹脂組成物が塗布性に劣るものとなることがある。上記充填剤の一次粒子径が50nmを超えると、得られる光湿気硬化型樹脂組成物が塗布後の形状保持性に劣るものとなることがある。上記充填剤の一次粒子径のより好ましい下限は5nm、より好ましい上限は30nm、更に好ましい下限は10nm、更に好ましい上限は20nmである。
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。
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。
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。
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。
なお、本明細書において上記「引張弾性率」は、引張り試験機(例えば、島津製作所社製、「EZ-Graph」)を用いて、硬化物を10mm/minの速度で引張り、50%伸びた時の力として測定される値を意味する。
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、ポリオキシテトラメチレン鎖を有するウレタンプレポリマーA-1(重量平均分子量2700)を得た。
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-1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時間撹拌し、混合しラジカル重合性官能基としてメタクリレート基を有し、かつ、ポリオキシテトラメチレン鎖を有するウレタンプレポリマーA-2(重量平均分子量3100)を得た。
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、ポリオキシプロピレン鎖を有するウレタンプレポリマーB(重量平均分子量2900)を得た。
表1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1~8、比較例1~3の光湿気硬化型樹脂組成物を得た。
なお、表1における「ウレタンプレポリマーA-1」は合成例1に記載した、ポリオキシテトラメチレン鎖を有し、かつ、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A-2」は合成例2に記載した、メタクリレート基及びポリオキシテトラメチレン鎖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3に記載した、ポリオキシプロピレン鎖を有し、かつ、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る。
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に示した。
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、100gの重りを置き、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(島津製作所社製、「Ez-Grapf」)を用いて、剪断方向に5mm/secの速度で引張り、ポリカーボネート基板とガラス板とが剥がれる際の強度を測定した。
上記「(接着性)」の評価における接着性評価用サンプルと同様にして高温高湿信頼性評価用サンプルを作製した。得られた高温高湿信頼性評価用サンプルのポリカーボネート基板の端に100gの重りを吊るし、サンプルを地面に対して垂直にぶら下げた状態で60℃、90RH%の恒温恒湿オーブンに入れ、24時間静置した。24時間静置後、ポリカーボネート基板とガラス板とが剥がれていなかった場合を「○」、ポリカーボネート基板とガラス板とが剥がれていた場合を「×」として、光湿気硬化型樹脂組成物の高温高湿信頼性(耐クリープ性)を評価した。
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、実施例及び比較例で得られた光湿気硬化型樹脂組成物を光硬化させ、その後、一晩放置することにより湿気硬化させた。得られた硬化物をダンベル状(「JIS K 6251」で規定される6号形)に打ち抜いて得られた試験片を、引張り試験機(島津製作所社製、「EZ-Graph」)を用いて、10mm/minの速度で引張り、50%伸びた時の力を弾性率として求めた。
2 光湿気硬化型樹脂組成物
3 ガラス板
Claims (7)
- 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を含有し、
前記湿気硬化型ウレタン樹脂は、分岐鎖を有していてもよいポリオキシアルキレン鎖を有し、かつ、該ポリオキシアルキレン鎖の各アルキレン基の炭素数が4以上であるウレタン樹脂A、及び、分岐鎖を有していてもよいポリオキシアルキレン鎖を有し、かつ、該ポリオキシアルキレン鎖の各アルキレン基の炭素数が3以下であるウレタン樹脂Bを含有する
ことを特徴とする光湿気硬化型樹脂組成物。 - ウレタン樹脂Aの含有量が、ウレタン樹脂Aとウレタン樹脂Bとの合計100重量部に対して30~80重量部であ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。
- 湿気硬化型ウレタン樹脂は、ラジカル重合性官能基を有す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。
- 遮光剤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。
- 充填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。
- 請求項1、2、3、4又は5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。
- 請求項1、2、3、4又は5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。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015517526A JP5989902B2 (ja) | 2014-03-26 | 2015-03-23 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
CN201580001962.1A CN105579477B (zh) | 2014-03-26 | 2015-03-23 | 光湿固化型树脂组合物、电子部件用粘接剂及显示元件用粘接剂 |
KR1020167004095A KR102271405B1 (ko) | 2014-03-26 | 2015-03-23 | 광 습기 경화형 수지 조성물, 전자 부품용 접착제, 및 표시 소자용 접착제 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014064245 | 2014-03-26 | ||
JP2014-064245 | 2014-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015146873A1 true WO2015146873A1 (ja) | 2015-10-01 |
Family
ID=54195387
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2015/058657 WO2015146873A1 (ja) | 2014-03-26 | 2015-03-23 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
Country Status (5)
Country | Link |
---|---|
JP (2) | JP5989902B2 (ja) |
KR (1) | KR102271405B1 (ja) |
CN (1) | CN105579477B (ja) |
TW (1) | TWI665280B (ja) |
WO (1) | WO2015146873A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017122145A (ja) * | 2016-01-05 | 2017-07-13 | 三菱ケミカル株式会社 | 重合組成物ならびに重合体及び成形体の製造方法 |
WO2020129994A1 (ja) * | 2018-12-18 | 2020-06-25 | 積水化学工業株式会社 | 光湿気硬化性ウレタン系化合物、光湿気硬化性ウレタンプレポリマー、及び光湿気硬化性樹脂組成物 |
EP3913028A4 (en) * | 2019-01-18 | 2022-09-21 | Sekisui Chemical Co., Ltd. | CURABLE RESIN COMPOSITION AND CURED BODY |
WO2023210394A1 (ja) * | 2022-04-25 | 2023-11-02 | 富士フイルム株式会社 | 組成物、膜、光センサおよび光センサの製造方法 |
JP7484090B2 (ja) | 2018-06-21 | 2024-05-16 | 三菱ケミカル株式会社 | 活性エネルギー線硬化性樹脂組成物、およびそれを用いたコーティング剤、ならびにシート |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107868620A (zh) * | 2017-11-21 | 2018-04-03 | 广东安普瑞新材料有限公司 | 一种黑色遮边uv胶 |
KR20210080352A (ko) * | 2018-10-23 | 2021-06-30 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 및 경화체 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5876828A (ja) * | 1981-10-30 | 1983-05-10 | Teijin Ltd | 感光性樹脂組成物 |
JPH01318028A (ja) * | 1988-06-17 | 1989-12-22 | Three Bond Co Ltd | 紫外線及び湿気硬化性ゴム弾性組成物 |
JPH069739A (ja) * | 1992-06-23 | 1994-01-18 | Hodogaya Chem Co Ltd | ポリウレタン系硬化性樹脂の製造方法 |
JP2001049225A (ja) * | 1999-06-02 | 2001-02-20 | Sekisui Chem Co Ltd | 湿気硬化型ウレタン系接着剤組成物又はシーリング剤組成物 |
JP2001062389A (ja) * | 1999-08-27 | 2001-03-13 | Nippon Shokubai Co Ltd | 土木建築用基材の表面処理方法 |
JP2002037832A (ja) * | 2000-07-24 | 2002-02-06 | Asahi Kasei Corp | 耐汚染性・耐タック性の優れたポリイソシアネート組成物 |
JP2005314681A (ja) * | 2004-03-31 | 2005-11-10 | Hodogaya Chem Co Ltd | 1液湿気硬化型ポリウレタン塗膜防水材 |
WO2008111323A1 (ja) * | 2007-03-15 | 2008-09-18 | Dic Corporation | 防水材用湿気硬化型ウレタン組成物及びウレタン防水材 |
JP2010037430A (ja) * | 2008-08-05 | 2010-02-18 | Sanyo Chem Ind Ltd | ポリウレタン系硬化性組成物 |
WO2015056717A1 (ja) * | 2013-10-18 | 2015-04-23 | 積水化学工業株式会社 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000178342A (ja) | 1998-12-17 | 2000-06-27 | Sumitomo Bakelite Co Ltd | 絶縁ペースト |
JP4342684B2 (ja) | 2000-03-21 | 2009-10-14 | 昭和高分子株式会社 | 水反応性光硬化性ウレタン樹脂組成物,frpライニング用樹脂組成物,プライマー樹脂組成物及びそれらの硬化方法 |
DE10350481A1 (de) * | 2003-10-29 | 2005-06-16 | Henkel Kgaa | Festigkeitsoptimierte Polymere mit gemischten Oxyalkyleneinheiten |
TWI410460B (zh) * | 2010-03-10 | 2013-10-01 | 紫外線感光性樹脂組成物以及其用途 | |
JP5488386B2 (ja) * | 2010-10-14 | 2014-05-14 | Dic株式会社 | 活性エネルギー線硬化性ホットメルトウレタン樹脂組成物、それを用いた電子機器用部材、及びパッキン |
CN103703087B (zh) * | 2011-07-22 | 2015-09-09 | H.B.富勒公司 | 用在电子器件上的单组分双固化粘合剂 |
-
2015
- 2015-03-23 WO PCT/JP2015/058657 patent/WO2015146873A1/ja active Application Filing
- 2015-03-23 JP JP2015517526A patent/JP5989902B2/ja active Active
- 2015-03-23 CN CN201580001962.1A patent/CN105579477B/zh active Active
- 2015-03-23 KR KR1020167004095A patent/KR102271405B1/ko active IP Right Grant
- 2015-03-24 TW TW104109283A patent/TWI665280B/zh active
-
2016
- 2016-07-22 JP JP2016144465A patent/JP2017014512A/ja active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5876828A (ja) * | 1981-10-30 | 1983-05-10 | Teijin Ltd | 感光性樹脂組成物 |
JPH01318028A (ja) * | 1988-06-17 | 1989-12-22 | Three Bond Co Ltd | 紫外線及び湿気硬化性ゴム弾性組成物 |
JPH069739A (ja) * | 1992-06-23 | 1994-01-18 | Hodogaya Chem Co Ltd | ポリウレタン系硬化性樹脂の製造方法 |
JP2001049225A (ja) * | 1999-06-02 | 2001-02-20 | Sekisui Chem Co Ltd | 湿気硬化型ウレタン系接着剤組成物又はシーリング剤組成物 |
JP2001062389A (ja) * | 1999-08-27 | 2001-03-13 | Nippon Shokubai Co Ltd | 土木建築用基材の表面処理方法 |
JP2002037832A (ja) * | 2000-07-24 | 2002-02-06 | Asahi Kasei Corp | 耐汚染性・耐タック性の優れたポリイソシアネート組成物 |
JP2005314681A (ja) * | 2004-03-31 | 2005-11-10 | Hodogaya Chem Co Ltd | 1液湿気硬化型ポリウレタン塗膜防水材 |
WO2008111323A1 (ja) * | 2007-03-15 | 2008-09-18 | Dic Corporation | 防水材用湿気硬化型ウレタン組成物及びウレタン防水材 |
JP2010037430A (ja) * | 2008-08-05 | 2010-02-18 | Sanyo Chem Ind Ltd | ポリウレタン系硬化性組成物 |
WO2015056717A1 (ja) * | 2013-10-18 | 2015-04-23 | 積水化学工業株式会社 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017122145A (ja) * | 2016-01-05 | 2017-07-13 | 三菱ケミカル株式会社 | 重合組成物ならびに重合体及び成形体の製造方法 |
JP7484090B2 (ja) | 2018-06-21 | 2024-05-16 | 三菱ケミカル株式会社 | 活性エネルギー線硬化性樹脂組成物、およびそれを用いたコーティング剤、ならびにシート |
WO2020129994A1 (ja) * | 2018-12-18 | 2020-06-25 | 積水化学工業株式会社 | 光湿気硬化性ウレタン系化合物、光湿気硬化性ウレタンプレポリマー、及び光湿気硬化性樹脂組成物 |
JPWO2020129994A1 (ja) * | 2018-12-18 | 2021-11-04 | 積水化学工業株式会社 | 光湿気硬化性ウレタン系化合物、光湿気硬化性ウレタンプレポリマー、及び光湿気硬化性樹脂組成物 |
JP7486414B2 (ja) | 2018-12-18 | 2024-05-17 | 積水化学工業株式会社 | 光湿気硬化性ウレタン系化合物、光湿気硬化性ウレタンプレポリマー、及び光湿気硬化性樹脂組成物 |
EP3913028A4 (en) * | 2019-01-18 | 2022-09-21 | Sekisui Chemical Co., Ltd. | CURABLE RESIN COMPOSITION AND CURED BODY |
WO2023210394A1 (ja) * | 2022-04-25 | 2023-11-02 | 富士フイルム株式会社 | 組成物、膜、光センサおよび光センサの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JP5989902B2 (ja) | 2016-09-07 |
CN105579477B (zh) | 2018-07-27 |
TW201546226A (zh) | 2015-12-16 |
JP2017014512A (ja) | 2017-01-19 |
KR20160140569A (ko) | 2016-12-07 |
CN105579477A (zh) | 2016-05-11 |
JPWO2015146873A1 (ja) | 2017-04-13 |
KR102271405B1 (ko) | 2021-06-30 |
TWI665280B (zh) | 2019-07-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5845362B2 (ja) | 電子部品用接着剤、及び、表示素子用接着剤 | |
JP5844504B1 (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP5989902B2 (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP6698524B2 (ja) | 硬化体、電子部品、表示素子、及び、光湿気硬化型樹脂組成物 | |
WO2015190499A1 (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP6434890B2 (ja) | 光湿気硬化型樹脂組成物 | |
JP6798791B2 (ja) | 電子部品用接着剤、及び、表示素子用接着剤 | |
JP6499561B2 (ja) | 光湿気硬化型樹脂組成物 | |
JP2016074783A (ja) | 光湿気硬化型樹脂組成物 | |
JP5824597B1 (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP2016074781A (ja) | 光湿気硬化型樹脂組成物 | |
JP2018002925A (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP2016147969A (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
WO2017094831A1 (ja) | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 | |
JP6622465B2 (ja) | 狭額縁設計表示素子用光湿気硬化型樹脂組成物硬化体 | |
JP2016074782A (ja) | 湿気硬化型樹脂組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201580001962.1 Country of ref document: CN |
|
ENP | Entry into the national phase |
Ref document number: 2015517526 Country of ref document: JP Kind code of ref document: A |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 15768135 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 20167004095 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 15768135 Country of ref document: EP Kind code of ref document: A1 |