KR20160111322A - 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
- KR20160111322A KR20160111322A KR1020157033386A KR20157033386A KR20160111322A KR 20160111322 A KR20160111322 A KR 20160111322A KR 1020157033386 A KR1020157033386 A KR 1020157033386A KR 20157033386 A KR20157033386 A KR 20157033386A KR 20160111322 A KR20160111322 A KR 20160111322A
- Authority
- KR
- South Korea
- Prior art keywords
- moisture
- light
- resin composition
- meth
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 91
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 33
- 239000000853 adhesive Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000013008 moisture curing Methods 0.000 claims abstract description 42
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 23
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 14
- 239000000945 filler Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 239000011164 primary particle Substances 0.000 claims description 11
- 238000001723 curing Methods 0.000 claims description 9
- 239000003504 photosensitizing agent Substances 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 10
- 230000000379 polymerizing effect Effects 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 77
- -1 methacryloyl group Chemical group 0.000 description 49
- 239000003822 epoxy resin Substances 0.000 description 41
- 229920000647 polyepoxide Polymers 0.000 description 41
- 229920005862 polyol Polymers 0.000 description 28
- 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 21
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 239000004593 Epoxy Substances 0.000 description 18
- 150000003077 polyols Chemical class 0.000 description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 17
- 239000010936 titanium Substances 0.000 description 17
- 229910052719 titanium Inorganic materials 0.000 description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 239000000126 substance Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 11
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 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
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 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
- 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
- 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
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000004381 surface treatment Methods 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
- 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 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000011163 secondary particle Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 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
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000012965 benzophenone Substances 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
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 238000006227 trimethylsilylation reaction Methods 0.000 description 2
- 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
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-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
- 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
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- 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
본 발명은, 차광성 및 접착성이 우수한 광 습기 경화형 수지 조성물을 제공하는 것을 목적으로 한다. 또한, 본 발명은 그 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제 및 표시 소자용 접착제를 제공하는 것을 목적으로 한다. 본 발명은, 라디칼 중합성 화합물과, 습기 경화형 우레탄 수지와, 광 라디칼 중합 개시제와, 차광제를 함유하는 광 습기 경화형 수지 조성물이다.An object of the present invention is to provide a light moisture curable resin composition excellent in light shielding property and adhesive property. It is another object of the present invention to provide an adhesive for electronic parts and an adhesive for a display element which are obtained by using the resin composition for optical and moisture curing. The present invention is a light moisture-curing resin composition containing a radical polymerizing compound, a moisture-curing urethane resin, a photo-radical polymerization initiator, and a light-shielding agent.
Description
본 발명은 차광성 및 접착성이 우수한 광 습기 경화형 수지 조성물에 관한 것이다. 또한, 본 발명은 그 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제 및 표시 소자용 접착제에 관한 것이다.The present invention relates to a light moisture curable resin composition excellent in light shielding property and adhesive property. The present invention also relates to an adhesive for an electronic part and an adhesive for a display element which are produced by using the resin composition for optical and moisture-setting.
최근, 박형, 경량, 저소비 전력 등의 특징을 갖는 표시 소자로서, 액정 표시 소자나 유기 EL 표시 소자 등이 널리 이용되고 있다. 이들 표시 소자에서는 통상, 액정이나 발광층의 밀봉, 기판이나 광학 필름이나 보호 필름이나 각종 부재의 접착 등에 광 경화형 수지 조성물이 사용되고 있다.2. Description of the Related Art In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having features such as thinness, light weight, and low power consumption. In these display devices, a photo-curable resin composition is usually used for sealing of a liquid crystal or a light-emitting layer, or for bonding a substrate, an optical film, a protective film or various members.
그런데, 휴대 전화, 휴대 게임기 등 각종 표시 소자가 부착된 모바일 기기가 보급되고 있는 현대에 있어서, 표시 소자의 소형화는 무엇보다도 요청되고 있는 과제이며, 소형화의 수법으로서 화상 표시부를 협프레임화하는 것이 행해지고 있다 (이하, 협프레임 설계라고도 한다). 그러나, 협프레임 설계에 있어서는, 충분히 광이 도달하지 않는 부분에 광 경화형 수지 조성물이 도포되는 경우가 있어, 그 결과, 광이 도달하지 않는 부분에 도포된 광 경화형 수지 조성물은 경화가 불충분해진다는 문제가 있었다.However, in the modern age in which mobile devices with various display devices such as mobile phones and portable game devices are in widespread use, miniaturization of display devices is a most demanded problem. As a method of miniaturization, the image display unit is narrowed (Hereinafter, also referred to as a narrow frame design). However, in the narrow-frame design, the light-curable resin composition may be applied to a portion where light does not sufficiently reach. As a result, the problem that the light curable resin composition applied to a portion where light does not reach becomes insufficient .
또, 광 경화형 수지 조성물이 충분히 광이 도달하지 않는 부분에 배치되어 있는 경우에도 표시 소자의 발광부로부터 광 경화형 수지 조성물을 투과하는 광을 차광할 수 없어, 광 누설에 의해 콘트라스트를 낮춰 버린다는 문제가 있었다.In addition, even when the photo-curable resin composition is disposed at a portion where light does not sufficiently reach, it is difficult to shield light transmitted through the light-curable resin composition from the light emitting portion of the display element, .
그래서, 광 경화형 수지 조성물에 차광성을 부여하기 위해 차광제를 첨가하는 방법을 고려할 수 있다. 그러나, 차광제를 첨가한 광 경화형 수지 조성물은 광 경화가 불충분해진다는 문제가 있었다. 특허문헌 1 에는, 광 경화가 불충분한 경우라도 가열에 의해 충분히 경화시킬 수 있는 광열 경화형 수지 조성물에 차광제를 배합하는 방법이 개시되어 있지만, 고온에서의 가열에 의해 소자 등에 악영향을 미칠 우려가 있었다.Therefore, a method of adding a light shielding agent to impart light shielding property to the photo-curable resin composition can be considered. However, the photo-curable resin composition to which the light-shielding agent is added has a problem that the photo-curing is insufficient. Patent Document 1 discloses a method of blending a light-shielding agent in a photo-setting resin composition which can be sufficiently cured by heating even when the photo-curing is insufficient, but there is a fear that the heating at a high temperature may adversely affect the elements .
본 발명은 차광성 및 접착성이 우수한 광 습기 경화형 수지 조성물을 제공하는 것을 목적으로 한다. 또한, 본 발명은 그 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제 및 표시 소자용 접착제를 제공하는 것을 목적으로 한다.An object of the present invention is to provide a light moisture curable resin composition excellent in light shielding property and adhesive property. It is another object of the present invention to provide an adhesive for electronic parts and an adhesive for a display element which are obtained by using the resin composition for optical and moisture curing.
본 발명은, 라디칼 중합성 화합물과, 습기 경화형 우레탄 수지와, 광 라디칼 중합 개시제와, 차광제를 함유하는 광 습기 경화형 수지 조성물이다.The present invention is a light moisture-curing resin composition containing a radical polymerizing compound, a moisture-curing urethane resin, a photo-radical polymerization initiator, and a light-shielding agent.
이하에 본 발명을 상세히 서술한다.Hereinafter, the present invention will be described in detail.
본 발명자들은, 차광제를 함유하는 수지 조성물을 고온에서의 가열을 실시하지 않고 경화시키는 방법으로서, 라디칼 중합성 화합물과 습기 경화형 우레탄 수지와 광 라디칼 중합 개시제를 함유하는 광 습기 경화형 수지 조성물에 차광제를 배합함으로써, 차광성과 접착성의 양방이 우수한 광 습기 경화형 수지 조성물을 얻을 수 있음을 알아내어, 본 발명을 완성시키기에 이르렀다.The present inventors have found that, as a method of curing a resin composition containing a light-shielding agent without heating at a high temperature, a light-moisture-curing resin composition containing a radical polymerizing compound, a moisture-curing urethane resin and a photo- , A light moisture-curing resin composition excellent in both light shielding property and adhesive property can be obtained, and the present invention has been accomplished.
본 발명의 광 습기 경화형 수지 조성물은 차광제를 함유한다. 상기 차광제를 함유함으로써, 본 발명의 광 습기 경화형 수지 조성물은 차광성이 우수한 것으로 되어 표시 소자의 광 누설을 방지할 수 있는 것이 된다.The light moisture-curing resin composition of the present invention contains a light-shielding agent. By containing the above-mentioned light-shielding agent, the light moisture-curing resin composition of the present invention is excellent in light shielding property, so that light leakage of the display element can be prevented.
또한, 본 명세서에 있어서, 상기 「차광제」는 가시광 영역의 광을 잘 투과시키지 않는 능력을 갖는 재료를 의미한다.In the present specification, the above-mentioned " light shielding agent " means a material having a capability of not transmitting light in the visible light region well.
상기 차광제로는, 예를 들어, 산화철, 티탄 블랙, 아닐린 블랙, 시아닌 블랙, 풀러렌, 카본 블랙, 수지 피복형 카본 블랙 등을 들 수 있다. 또한, 상기 차광제는 흑색을 나타내는 것이 아니어도 되고, 가시광 영역의 광을 잘 투과시키지 않는 능력을 갖는 재료이면, 실리카나 탤크 등, 후술하는 충전제로서 예시하는 재료 등도 상기 차광제에 포함된다. 그 중에서도 티탄 블랙이 바람직하다.Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. The light-shielding agent may not be black, and a material exemplified as a filler to be described later, such as silica or talc, is also included in the light-shielding agent as long as it has a capability of not transmitting light in the visible light region. Among them, titanium black is preferable.
상기 티탄 블랙은, 파장 300 ∼ 800 ㎚ 의 광에 대한 평균 투과율과 비교하여 자외선 영역 부근, 특히 파장 370 ∼ 450 ㎚ 의 광에 대한 투과율이 높아지는 물질이다. 즉, 상기 티탄 블랙은, 가시광 영역의 파장의 광을 충분히 차폐함으로써 본 발명의 광 습기 경화형 수지 조성물에 차광성을 부여하는 한편, 자외선 영역 부근의 파장의 광은 투과시키는 성질을 갖는 차광제이다. 따라서, 광 라디칼 중합 개시제로서, 상기 티탄 블랙의 투과율이 높아지는 파장 (370 ∼ 450 ㎚) 의 광에 의해 반응을 개시 가능한 것을 사용함으로써, 본 발명의 광 습기 경화형 수지 조성물의 광 경화성을 보다 증대시킬 수 있다. 또한 한편으로, 본 발명의 광 습기 경화형 수지 조성물에 함유되는 차광제로는 절연성이 높은 물질이 바람직하고, 절연성이 높은 차광제로서도 티탄 블랙이 바람직하다.The titanium black is a material having a higher transmittance to light in the vicinity of the ultraviolet ray region, particularly in the wavelength range of 370 to 450 nm, as compared with the average transmittance in the wavelength range of 300 to 800 nm. That is, the titanium black is a light-shielding agent having properties of imparting light shielding properties to the light moisture-setting type resin composition of the present invention by sufficiently shielding light having a wavelength in the visible light region while transmitting light having a wavelength near the ultraviolet light region. Therefore, as the photo radical polymerization initiator, it is possible to further increase the photo-curability of the photo-moisture-setting type resin composition of the present invention by using a material capable of initiating the reaction by light having a wavelength (370 to 450 nm) at which the transmittance of the titanium black becomes high have. On the other hand, as the light-shielding agent contained in the photo-moisture-setting type resin composition of the present invention, a material having high insulating property is preferable, and titanium black is preferable as a light-shielding agent having high insulating property.
상기 티탄 블랙은, 광학 농도 (OD 값) 가 3 이상인 것이 바람직하고, 4 이상인 것이 보다 바람직하다. 또한, 상기 티탄 블랙은, 흑색도 (L 값) 가 9 이상인 것이 바람직하고, 11 이상인 것이 보다 바람직하다. 상기 티탄 블랙의 차광성은 높으면 높을수록 좋으며, 상기 티탄 블랙의 OD 값에 바람직한 상한은 특별히 없지만, 통상은 5 이하가 된다.The titanium black preferably has an optical density (OD value) of 3 or more, 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 is, the better, and the preferable upper limit to the OD value of the titanium black is not particularly limited, but it is usually 5 or less.
상기 티탄 블랙은, 표면 처리되어 있지 않은 것이라도 충분한 효과를 발휘하지만, 표면이 커플링제 등의 유기 성분으로 처리되어 있는 것이나, 산화규소, 산화티탄, 산화게르마늄, 산화알루미늄, 산화지르코늄, 산화마그네슘 등의 무기 성분으로 피복되어 있는 것 등, 표면 처리된 티탄 블랙을 사용할 수도 있다. 그 중에서도, 유기 성분으로 처리되어 있는 것은 보다 절연성을 향상시킬 수 있는 점에서 바람직하다.The titanium black exhibits a sufficient effect even if it is not surface-treated. However, the titanium black may be one having a surface treated with an organic component such as a coupling agent, or a metal oxide such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide Or a titanium black coated with an inorganic component such as titanium black. Among them, those treated with an organic component are preferable in that they can further improve the insulation.
또한, 본 발명의 광 습기 경화형 수지 조성물을 사용하여 제조한 표시 소자는, 광 습기 경화형 수지 조성물이 충분한 차광성을 갖기 때문에, 광의 누설이 없고 높은 콘트라스트를 가져, 우수한 화상 표시 품질을 갖는 것이 된다.Further, in the display device manufactured using the photo-moisture-setting type resin composition of the present invention, since the photo-moisture-setting type resin composition has sufficient light shielding property, there is no leakage of light, high contrast is obtained, and excellent image display quality is obtained.
상기 티탄 블랙 중 시판되고 있는 것으로는, 예를 들어, 12S, 13M, 13M-C, 13R-N (모두 미츠비시 마테리알사 제조), 틸랙 D (아코 카세이사 제조) 등을 들 수 있다.Examples of commercially available titanium black include 12S, 13M, 13M-C and 13R-N (all manufactured by Mitsubishi Materials Corporation) and Tilac D (manufactured by Akokase Corporation).
상기 티탄 블랙의 비표면적의 바람직한 하한은 5 ㎡/g, 바람직한 상한은 40 ㎡/g 이고, 보다 바람직한 하한은 10 ㎡/g, 보다 바람직한 상한은 25 ㎡/g 이다.The preferable lower limit of the specific surface area of the titanium black is 5
또한, 상기 티탄 블랙의 시트 저항의 바람직한 하한은, 수지와 혼합된 경우 (70 % 배합) 에 있어서, 109 Ω/□ 이고, 보다 바람직한 하한은 1011 Ω/□ 이다.The preferable lower limit of the sheet resistance of the titanium black is 10 9 ? /? When mixed with the resin (70%), and the lower limit is more preferably 10 11 ? / ?.
본 발명의 광 습기 경화형 수지 조성물에 있어서, 상기 차광제의 일차 입자 직경은, 표시 소자의 기판간 거리 이하 등, 용도에 따라 적절히 선택되지만, 바람직한 하한은 30 ㎚, 바람직한 상한은 500 ㎚ 이다. 상기 차광제의 일차 입자 직경이 30 ㎚ 미만이면, 얻어지는 광 습기 경화형 수지 조성물의 점도나 틱소트로피가 크게 증대되어 버려, 작업성이 나빠지는 경우가 있다. 상기 차광제의 일차 입자 직경이 500 ㎚ 를 초과하면, 얻어지는 광 습기 경화형 수지 조성물 중에 있어서의 차광제의 분산성이 저하되어, 차광성이 저하되는 경우가 있다. 상기 차광제의 일차 입자 직경의 보다 바람직한 하한은 50 ㎚, 보다 바람직한 상한은 200 ㎚ 이다.In the photo-moisture-setting type resin composition of the present invention, the primary particle diameter of the light-shielding agent is appropriately selected according to the application, such as the distance between the substrates of the display element, etc., but the preferred lower limit is 30 nm and the preferred upper limit is 500 nm. When the light-shielding agent has a primary particle diameter of less than 30 nm, the viscosity and thixotropy of the obtained moisture-curable resin composition are greatly increased, and the workability is sometimes deteriorated. When the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the resulting photo-moisture-setting type resin composition is lowered and the light-shielding property may be lowered. A more preferable lower limit of the primary particle diameter of the light shielding agent is 50 nm, and a more preferable upper limit is 200 nm.
본 발명의 광 습기 경화형 수지 조성물 전체에 있어서의 상기 차광제의 함유량은 특별히 한정되지 않지만, 바람직한 하한은 0.05 중량%, 바람직한 상한은 10 중량% 이다. 상기 차광제의 함유량이 0.05 중량% 미만이면, 충분한 차광성이 얻어지지 않는 경우가 있다. 상기 차광제의 함유량이 10 중량% 를 초과하면, 얻어지는 광 습기 경화형 수지 조성물의 기판 등에 대한 접착성이나 경화 후의 강도가 저하되거나, 묘화성이 저하되거나 하는 경우가 있다. 상기 차광제의 함유량의 보다 바람직한 하한은 0.1 중량%, 보다 바람직한 상한은 2 중량%, 더욱 바람직한 하한은 0.3 중량%, 더욱 바람직한 상한은 1 중량% 이다.The content of the above-mentioned light-shielding agent in the entire moisture-curing resin composition of the present invention is not particularly limited, but the lower limit is preferably 0.05% by weight and the upper limit is preferably 10% by weight. When 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 adhesion of the resultant light moisture curable resin composition to a substrate or the like may be lowered or the strength after curing may be lowered. A more preferable lower limit of the content of the light-shielding agent is 0.1 wt%, a more preferable upper limit is 2 wt%, a still more preferable lower limit is 0.3 wt%, and a more preferable upper limit is 1 wt%.
본 발명의 광 습기 경화형 수지 조성물은, 라디칼 중합성 화합물을 함유한다.The moisture-curing resin composition of the present invention contains a radically polymerizable compound.
상기 라디칼 중합성 화합물로는, 분자 중에 라디칼 반응성 관능기를 갖는 화합물이면 특별히 한정되지 않지만, 라디칼 반응성 관능기로서 불포화 2 중 결합을 갖는 화합물이 바람직하고, 특히 반응성의 면에서 (메트)아크릴로일기를 갖는 수지 (이하,「(메트)아크릴 수지」라고도 한다) 가 바람직하다.The radically 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 a radical reactive functional group is preferable, and a compound having a (meth) acryloyl group (Hereinafter also referred to as " (meth) acrylic resin ").
또한, 본 명세서에 있어서, 상기 「(메트)아크릴로일기」는 아크릴로일기 또는 메타크릴로일기를 의미하고, 상기 「(메트)아크릴」은 아크릴 또는 메타크릴을 의미한다.In the present specification, the term "(meth) acryloyl group" means an acryloyl group or a methacryloyl group, and the term "(meth) acryl" means acryl or methacryloyl.
상기 (메트)아크릴 수지로는, 예를 들어, (메트)아크릴산에 수산기를 갖는 화합물을 반응시킴으로써 얻어지는 에스테르 화합물, (메트)아크릴산과 에폭시 화합물을 반응시킴으로써 얻어지는 에폭시(메트)아크릴레이트, 이소시아네이트에 수산기를 갖는 (메트)아크릴산 유도체를 반응시킴으로써 얻어지는 우레탄(메트)아크릴레이트 등을 들 수 있다.Examples of the (meth) acrylic resin include an ester compound obtained by reacting a compound having a hydroxyl group in (meth) acrylic acid, an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with an epoxy compound, (Meth) acrylic acid derivatives having at least one functional group selected from the group consisting of (meth) acrylate and (meth) acrylate.
또한, 본 명세서에 있어서, 상기 「(메트)아크릴레이트」란 아크릴레이트 또는 메타크릴레이트를 의미한다.In the present specification, the term "(meth) acrylate" means acrylate or methacrylate.
상기 에스테르 화합물 중 단관능의 것으로는, 예를 들어, N-아크릴로일옥시에틸헥사하이드로프탈이미드 등의 프탈이미드아크릴레이트류나 각종 이미드아크릴레이트, 2-하이드록시에틸(메트)아크릴레이트, 2-하이드록시프로필(메트)아크릴레이트, 4-하이드록시부틸(메트)아크릴레이트, 2-하이드록시부틸(메트)아크릴레이트, 이소부틸(메트)아크릴레이트, t-부틸(메트)아크릴레이트, 이소옥틸(메트)아크릴레이트, 라우릴(메트)아크릴레이트, 스테아릴(메트)아크릴레이트, 이소보르닐(메트)아크릴레이트, 시클로헥실(메트)아크릴레이트, 2-메톡시에틸(메트)아크릴레이트, 메톡시에틸렌글리콜(메트)아크릴레이트, 2-에톡시에틸(메트)아크릴레이트, 테트라하이드로푸르푸릴(메트)아크릴레이트, 벤질(메트)아크릴레이트, 에틸카르비톨(메트)아크릴레이트, 페녹시에틸(메트)아크릴레이트, 페녹시디에틸렌글리콜(메트)아크릴레이트, 페녹시폴리에틸렌글리콜(메트)아크릴레이트, 메톡시폴리에틸렌글리콜(메트)아크릴레이트, 2,2,2-트리플루오로에틸(메트)아크릴레이트, 2,2,3,3-테트라플루오로프로필(메트)아크릴레이트, 1H,1H,5H-옥타플루오로펜틸(메트)아크릴레이트, 이미드(메트)아크릴레이트, 메틸(메트)아크릴레이트, 에틸(메트)아크릴레이트, n-부틸(메트)아크릴레이트, 프로필(메트)아크릴레이트, 2-에틸헥실(메트)아크릴레이트, n-옥틸(메트)아크릴레이트, 이소노닐(메트)아크릴레이트, 이소미리스틸(메트)아크릴레이트, 2-부톡시에틸(메트)아크릴레이트, 2-페녹시에틸(메트)아크릴레이트, 비시클로펜테닐(메트)아크릴레이트, 이소데실(메트)아크릴레이트, 디에틸아미노에틸(메트)아크릴레이트, 디메틸아미노에틸(메트)아크릴레이트, 2-(메트)아크릴로일옥시에틸숙신산, 2-(메트)아크릴로일옥시에틸헥사하이드로프탈산, 2-(메트)아크릴로일옥시에틸2-하이드록시프로필프탈레이트, 글리시딜(메트)아크릴레이트, 2-(메트)아크릴로일옥시에틸포스페이트 등을 들 수 있다.Examples of the monofunctional compound in the ester compound include phthalimide acrylates such as N-acryloyloxyethylhexahydrophthalimide, various imide acrylates, 2-hydroxyethyl (meth) acryl (Meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (Meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl ) Acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, ethylcarbitol , Phenox (Meth) acrylate, phenoxyethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 2,2,2-trifluoroethyl (Meth) acrylate, imide (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (Meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, propyl (meth) acrylate, (Meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, bicyclopentenyl (meth) acrylate, isodecyl Diethylaminoethyl (meth) acrylate, dimethylaminoethyl ( Acrylates such as 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, glycidyl (Meth) acrylate, 2- (meth) acryloyloxyethyl phosphate, and the like.
또한, 상기 에스테르 화합물 중 2 관능의 것으로는, 예를 들어, 1,4-부탄디올디(메트)아크릴레이트, 1,3-부탄디올디(메트)아크릴레이트, 1,6-헥산디올디(메트)아크릴레이트, 1,9-노난디올디(메트)아크릴레이트, 1,10-데칸디올디(메트)아크릴레이트, 2-n-부틸-2-에틸-1,3-프로판디올디(메트)아크릴레이트, 디프로필렌글리콜디(메트)아크릴레이트, 트리프로필렌글리콜디(메트)아크릴레이트, 폴리프로필렌 글리콜(메트)아크릴레이트, 에틸렌글리콜디(메트)아크릴레이트, 디에틸렌글리콜디(메트)아크릴레이트, 테트라에틸렌글리콜디(메트)아크릴레이트, 폴리에틸렌글리콜디(메트)아크릴레이트, 프로필렌옥사이드 부가 비스페놀 A 디(메트)아크릴레이트, 에틸렌옥사이드 부가 비스페놀 A 디(메트)아크릴레이트, 에틸렌옥사이드 부가 비스페놀 F 디(메트)아크릴레이트, 디메틸올디시클로펜타디에닐디(메트)아크릴레이트, 네오펜틸글리콜디(메트)아크릴레이트, 에틸렌옥사이드 변성 이소시아누르산디(메트)아크릴레이트, 2-하이드록시-3-(메트)아크릴로일옥시프로필(메트)아크릴레이트, 카보네이트디올디(메트)아크릴레이트, 폴리에테르디올디(메트)아크릴레이트, 폴리에스테르디올디(메트)아크릴레이트, 폴리카프로락톤디올디(메트)아크릴레이트, 폴리부타디엔디올디(메트)아크릴레이트 등을 들 수 있다.Examples of the bifunctional compound in the ester compound include 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,6- Acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 2-n-butyl- Acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (Meth) acrylate, ethylene oxide adduct bisphenol A (meth) acrylate, ethylene oxide adduct bisphenol A (meth) acrylate, ethylene oxide adduct bisphenol A Meth) acrylate, (Meth) acrylate, ethylene oxide modified diisocyanurate di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, (Meth) acrylate, polycaprolactone diol di (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (Meth) acrylate, and the like.
또한, 상기 에스테르 화합물 중 3 관능 이상의 것으로는, 예를 들어, 펜타에리트리톨트리(메트)아크릴레이트, 트리메틸올프로판트리(메트)아크릴레이트, 프로필렌옥사이드 부가 트리메틸올프로판트리(메트)아크릴레이트, 에틸렌옥사이드 부가 트리메틸올프로판트리(메트)아크릴레이트, 카프로락톤 변성 트리메틸올프로판트리(메트)아크릴레이트, 에틸렌옥사이드 부가 이소시아누르산트리(메트)아크릴레이트, 디펜타에리트리톨펜타(메트)아크릴레이트, 디펜타에리트리톨헥사(메트)아크릴레이트, 디트리메틸올프로판테트라(메트)아크릴레이트, 펜타에리트리톨테트라(메트)아크릴레이트, 글리세린트리(메트)아크릴레이트, 프로필렌옥사이드 부가 글리세린트리(메트)아크릴레이트, 트리스(메트)아크릴로일옥시에틸포스페이트 등을 들 수 있다.Examples of the trifunctional or higher functional group in the ester compound include pentaerythritol tri (meth) acrylate, trimethylol propane tri (meth) acrylate, propylene oxide added trimethylol propane tri (meth) acrylate, ethylene (Meth) acrylate, ethylene oxide adduct isocyanuric acid tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethylene oxide adduct isocyanuric acid tri (meth) (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylol propane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, glycerin tri , Tris (meth) acryloyloxyethyl phosphate, and the like.
상기 에폭시(메트)아크릴레이트로는, 예를 들어, 에폭시 화합물과 (메트)아크릴산을 통상적인 방법에 따라서 염기성 촉매의 존재하에서 반응시킴으로써 얻어지는 것 등을 들 수 있다.The epoxy (meth) acrylate includes, for example, those obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
상기 에폭시(메트)아크릴레이트를 합성하기 위한 원료가 되는 에폭시 화합물로는, 예를 들어, 비스페놀 A 형 에폭시 수지, 비스페놀 F 형 에폭시 수지, 비스페놀 S 형 에폭시 수지, 2,2'-디알릴비스페놀 A 형 에폭시 수지, 수소 첨가 비스페놀형 에폭시 수지, 프로필렌 옥사이드 부가 비스페놀 A 형 에폭시 수지, 레조르시놀형 에폭시 수지, 비페닐형 에폭시 수지, 술파이드형 에폭시 수지, 디페닐에테르형 에폭시 수지, 디시클로펜타디엔형 에폭시 수지, 나프탈렌형 에폭시 수지, 페놀노볼락형 에폭시 수지, 오르토크레졸노볼락형 에폭시 수지, 디시클로펜타디엔노볼락형 에폭시 수지, 비페닐노볼락형 에폭시 수지, 나프탈렌페놀노볼락형 에폭시 수지, 글리시딜아민형 에폭시 수지, 알킬폴리올형 에폭시 수지, 고무 변성형 에폭시 수지, 글리시딜에스테르 화합물, 비스페놀 A 형 에피술파이드 수지 등을 들 수 있다.Examples of the epoxy compound to be 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, 2,2'-diallyl bisphenol A Type epoxy resin, a hydrogenated bisphenol type epoxy resin, a propylene oxide-added bisphenol A type epoxy resin, a resorcinol type epoxy resin, a biphenyl type epoxy resin, a sulfide type epoxy resin, a diphenyl ether type epoxy resin, a dicyclopentadiene type Epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, orthocresol novolak type epoxy resin, dicyclopentadiene novolak type epoxy resin, biphenyl novolac type epoxy resin, naphthalene phenol novolak type epoxy resin, Alkylpolyol type epoxy resin, rubber modified epoxy resin, glycidyl ester compound Water, bisphenol A type episulfide resin, and the like.
상기 비스페놀 A 형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, jER828EL, jER1001, jER1004 (모두 미츠비시 화학사 제조), 에피클론 850-S (DIC 사 제조) 등을 들 수 있다.Examples of commercially available bisphenol A type epoxy resins include jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation) and Epiclon 850-S (manufactured by DIC Corporation).
상기 비스페놀 F 형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, jER806, jER4004 (모두 미츠비시 화학사 제조) 등을 들 수 있다.Examples of commercially available bisphenol F type epoxy resins include, for example, jER806 and jER4004 (all manufactured by Mitsubishi Chemical Corporation).
상기 비스페놀 S 형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 EXA1514 (DIC 사 제조) 등을 들 수 있다.Examples of commercially available bisphenol S epoxy resins include Epiclon EXA1514 (manufactured by DIC Corporation) and the like.
상기 2,2'-디알릴비스페놀 A 형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, RE-810NM (닛폰 화약사 제조) 등을 들 수 있다.Examples of commercially available 2,2'-diallyl bisphenol A type epoxy resins include RE-810NM (manufactured by Nippon Yakusho Co., Ltd.) and the like.
상기 수소 첨가 비스페놀형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 EXA7015 (DIC 사 제조) 등을 들 수 있다.Examples of the hydrogenated bisphenol-type epoxy resin commercially available include Epiclon EXA7015 (manufactured by DIC Corporation) and the like.
상기 프로필렌옥사이드 부가 비스페놀 A 형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, EP-4000S (ADEKA 사 제조) 등을 들 수 있다.Examples of the propylene oxide-added bisphenol A type epoxy resin commercially available include EP-4000S (manufactured by ADEKA) and the like.
상기 레조르시놀형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, EX-201 (나가세 켐텍스사 제조) 등을 들 수 있다.Examples of commercially available resorcinol-type epoxy resins include EX-201 (manufactured by Nagase ChemteX Corporation) and the like.
상기 비페닐형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, jER YX-4000H (미츠비시 화학사 제조) 등을 들 수 있다.Examples of commercially available biphenyl type epoxy resins include, for example, jER YX-4000H (manufactured by Mitsubishi Chemical Corporation).
상기 술파이드형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, YSLV-50TE (신닛테츠 스미킨 화학사 제조) 등을 들 수 있다.Examples of commercially available sulfide type epoxy resins include YSLV-50TE (manufactured by Shinnitetsu Sumikin Chemical Co., Ltd.) and the like.
상기 디페닐에테르형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, YSLV-80DE (신닛테츠 스미킨 화학사 제조) 등을 들 수 있다.Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Shinnitetsu Sumikin Chemical Industry Co., Ltd.) and the like.
상기 디시클로펜타디엔형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, EP-4088S (ADEKA 사 제조) 등을 들 수 있다.Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA) and the like.
상기 나프탈렌형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 HP4032, 에피클론 EXA-4700 (모두 DIC 사 제조) 등을 들 수 있다.Examples of commercially available naphthalene type epoxy resins include Epiclon HP4032 and Epiclon EXA-4700 (both manufactured by DIC).
상기 페놀노볼락형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 N-770 (DIC 사 제조) 등을 들 수 있다.Examples of commercially available phenol novolak epoxy resins include Epiclon N-770 (manufactured by DIC Corporation) and the like.
상기 오르토크레졸노볼락형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 N-670-EXP-S (DIC 사 제조) 등을 들 수 있다.Examples of the commercially available orthocresol novolak type epoxy resin include Epiclon N-670-EXP-S (manufactured by DIC Corporation) and the like.
상기 디시클로펜타디엔노볼락형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, 에피클론 HP7200 (DIC 사 제조) 등을 들 수 있다.Examples of commercially available dicyclopentadiene novolak type epoxy resins include Epiclon HP7200 (manufactured by DIC Corporation) and the like.
상기 비페닐노볼락형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, NC-3000P (닛폰 화약사 제조) 등을 들 수 있다.Commercially available examples of the biphenyl novolak type epoxy resin include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
상기 나프탈렌페놀노볼락형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, ESN-165S (신닛테츠 스미킨 화학사 제조) 등을 들 수 있다.Examples of commercially available naphthalene phenol novolak type epoxy resins include ESN-165S (manufactured by Shinnitetsu Sumikin Chemical Co., Ltd.).
상기 글리시딜아민형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, jER630 (미츠비시 화학사 제조), 에피클론 430 (DIC 사 제조), TETRAD-X (미츠비시 가스 화학사 제조) 등을 들 수 있다.Examples of commercially available glycidylamine type epoxy resins include jER 630 (manufactured by Mitsubishi Chemical Corporation), Epiclon 430 (manufactured by DIC Corporation), and TETRAD-X (manufactured by Mitsubishi Gas Chemical Company).
상기 알킬폴리올형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, ZX-1542 (신닛테츠 스미킨 화학사 제조), 에피클론 726 (DIC 사 제조), 에포라이트 80MFA (교에이샤 화학사 제조), 데나콜 EX-611 (나가세 켐텍스사 제조) 등을 들 수 있다.Examples of commercially available products of the alkyl polyol type epoxy resin include ZX-1542 (manufactured by Shinnitetsu Sumikin Chemical Co., Ltd.), Epiclon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) Cole EX-611 (manufactured by Nagase ChemteX Corporation), and the like.
상기 고무 변성형 에폭시 수지 중 시판되고 있는 것으로는, 예를 들어, YR-450, YR-207 (모두 신닛테츠 스미킨 화학사 제조), 에포리드 PB (다이셀사 제조) 등을 들 수 있다.Examples of the commercially available rubber-modified epoxy resin include YR-450 and YR-207 (all manufactured by Shinnitetsu Sumikin Chemical Industry Co., Ltd.) and Epolide PB (manufactured by Daicel Chemical Industries, Ltd.).
상기 글리시딜에스테르 화합물 중 시판되고 있는 것으로는, 예를 들어, 데나콜 EX-147 (나가세 켐텍스사 제조) 등을 들 수 있다.Examples of commercially available glycidyl ester compounds include, for example, Denacol EX-147 (manufactured by Nagase ChemteX).
상기 비스페놀 A 형 에피술파이드 수지 중 시판되고 있는 것으로는, 예를 들어, jER YL-7000 (미츠비시 화학사 제조) 등을 들 수 있다.Examples of commercially available bisphenol A episulfide resins include jER YL-7000 (manufactured by Mitsubishi Chemical Corporation).
상기 에폭시 수지 중 그 밖에 시판되고 있는 것으로는, 예를 들어, YDC-1312, YSLV-80XY, YSLV-90CR (모두 신닛테츠 스미킨 화학사 제조), XAC4151 (아사히 카세이사 제조), jER1031, jER1032 (모두 미츠비시 화학사 제조), EXA-7120 (DIC 사 제조), TEPIC (닛산 화학사 제조) 등을 들 수 있다.Examples of other commercially available epoxy resins include YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Shinnitetsu Sumikin Chemical Industry Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Corporation), jER1031 and jER1032 EXA-7120 (manufactured by DIC Corporation), and TEPIC (manufactured by Nissan Chemical Industries, Ltd.).
상기 에폭시(메트)아크릴레이트 중 시판되고 있는 것으로는, 예를 들어, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 (모두 다이셀·올넥스사 제조), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (모두 신나카무라 화학 공업사 제조), 에폭시에스테르 M-600A, 에폭시에스테르 40EM, 에폭시에스테르 70PA, 에폭시에스테르 200PA, 에폭시에스테르 80MFA, 에폭시에스테르 3002M, 에폭시에스테르 3002A, 에폭시에스테르 1600A, 에폭시에스테르 3000M, 에폭시에스테르 3000A, 에폭시에스테르 200EA, 에폭시에스테르 400EA (모두 교에이샤 화학사 제조), 데나콜아크릴레이트 DA-141, 데나콜아크릴레이트 DA-314, 데나콜아크릴레이트 DA-911 (모두 나가세 켐텍스사 제조) 등을 들 수 있다.Examples of commercially available epoxy (meth) acrylates include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 (All manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy resin (manufactured by Shin-Nakamura Chemical Co., Ltd.), EA-1010, EA-1020, EA-5323, EA-5520, EA- Epoxy ester 300A, Epoxy ester 300A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A, Epoxy ester 200EA, Epoxy ester 400EA (all from Kyoeisha Chemical Co., Ltd.), Denacol acrylate DA-141 , Denacol acrylate DA-314, Denacol acrylate DA-911 (all manufactured by Nagase Chemtech), and the like.
상기 우레탄(메트)아크릴레이트는, 예를 들어, 2 개의 이소시아네이트기를 갖는 화합물 1 당량에 대하여, 수산기를 갖는 (메트)아크릴산 유도체 2 당량을 촉매량의 주석계 화합물 존재하에서 반응시킴으로써 얻을 수 있다.The urethane (meth) acrylate can be 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 compound.
상기 우레탄(메트)아크릴레이트의 원료가 되는 이소시아네이트로는, 예를 들어, 이소포론디이소시아네이트, 2,4-톨릴렌디이소시아네이트, 2,6-톨릴렌디이소시아네이트, 헥사메틸렌디이소시아네이트, 트리메틸헥사메틸렌디이소시아네이트, 디페닐메탄-4,4'-디이소시아네이트 (MDI), 수소 첨가 MDI, 폴리메릭 MDI, 1,5-나프탈렌디이소시아네이트, 노르보르난디이소시아네이트, 톨리딘디이소시아네이트, 자일릴렌디이소시아네이트 (XDI), 수소 첨가 XDI, 리신디이소시아네이트, 트리페닐메탄트리이소시아네이트, 트리스(이소시아네이트페닐)티오포스페이트, 테트라메틸자일렌디이소시아네이트, 1,6,11-운데칸트리이소시아네이트 등을 들 수 있다.Examples of the isocyanate as a raw material of the urethane (meth) acrylate include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornadiisocyanate, tolylidine diisocyanate, xylylene diisocyanate (XDI), hydrogen (XDI), lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanate phenyl) thiophosphate, tetramethyl xylene diisocyanate, and 1,6,11-undecane triisocyanate.
또한, 상기 이소시아네이트로는, 예를 들어, 에틸렌글리콜, 글리세린, 소르비톨, 트리메틸올프로판, (폴리)프로필렌글리콜, 카보네이트디올, 폴리에테르디올, 폴리에스테르디올, 폴리카프로락톤디올 등의 폴리올과 과잉의 이소시아네이트와의 반응에 의해 얻어지는 사슬 연장된 이소시아네이트 화합물도 사용할 수 있다.Examples of the isocyanate include polyols such as ethylene glycol, glycerin, sorbitol, trimethylol propane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol and polycaprolactone diol, and excess isocyanate Chain extended isocyanate compound obtained by a reaction with an isocyanate group-containing compound.
상기 우레탄(메트)아크릴레이트의 원료가 되는, 수산기를 갖는 (메트)아크릴산 유도체로는, 예를 들어, 에틸렌글리콜, 프로필렌글리콜, 1,3-프로판디올, 1,3-부탄디올, 1,4-부탄디올, 폴리에틸렌글리콜 등의 2 가 알코올의 모노(메트)아크릴레이트나, 트리메틸올에탄, 트리메틸올프로판, 글리세린 등의 3 가 알코올의 모노(메트)아크릴레이트 또는 디(메트)아크릴레이트나, 비스페놀 A 형 에폭시(메트)아크릴레이트 등의 에폭시(메트)아크릴레이트 등을 들 수 있다.Examples of the (meth) acrylic acid derivative having a hydroxyl group which is a raw material of the urethane (meth) acrylate include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3- Mono (meth) acrylate of a dihydric alcohol such as butanediol and polyethylene glycol, mono (meth) acrylate or di (meth) acrylate of a trihydric alcohol such as trimethylolethane, trimethylolpropane or glycerin, And epoxy (meth) acrylates such as epoxy (meth) acrylate.
상기 우레탄(메트)아크릴레이트 중 시판되고 있는 것으로는, 예를 들어, M-1100, M-1200, M-1210, M-1600 (모두 토아 합성사 제조), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (모두 다이셀·올넥스사 제조), 아트레진 UN-9000H, 아트레진 UN-9000A, 아트레진 UN-7100, 아트레진 UN-1255, 아트레진 UN-330, 아트레진 UN-3320HB, 아트레진 UN-1200TPK, 아트레진 SH-500B (모두 네가미 공업사 제조), U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U-122P, U-108, U-108A, U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (모두 신나카무라 화학 공업사 제조), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (모두 교에이샤 화학사 제조) 등을 들 수 있다.Examples of commercially available urethane (meth) acrylate include M-1100, M-1200, M-1210 and M-1600 (all manufactured by TOAGOSEI Co.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (all manufactured by Daicel Alnex) Art Resin UN-7000, Art Resin UN-7000, Art Resin UN-7000, Art Resin UN-9000A, Art Resin UN-7100, Art Resin UN-1255, Art Resin UN-330, Art Resin UN-3320HB, U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U-122P, UA-3401, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-340A, U- AH-600, AT-600, UA-101I, UA-101T, UA-306H and UA-W2A (all manufactured by Shin-Nakamura Chemical Co., UA-306I, and UA-306T (all manufactured by Kyoeisha Chemical Co., Ltd.).
또한, 상기 서술한 것 이외의 그 밖의 라디칼 중합성 화합물도 적절히 사용할 수 있다.Other radically polymerizable compounds other than those described above may also be suitably used.
상기 그 밖의 라디칼 중합성 화합물로는, 예를 들어, N,N-디메틸(메트)아크릴아미드, N-(메트)아크릴로일모르폴린, N-하이드록시에틸(메트)아크릴아미드, N,N-디에틸(메트)아크릴아미드, N-이소프로필(메트)아크릴아미드, N,N-디메틸아미노프로필(메트)아크릴아미드 등의 (메트)아크릴아미드 화합물, 스티렌, α-메틸스티렌, N-피로피돈, N-비닐카프로락톤 등의 비닐 화합물 등을 들 수 있다.Examples of the other radically polymerizable compounds include N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (Meth) acrylamide compounds such as diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide and N, N-dimethylaminopropyl (meth) acrylamide, styrene, And vinyl compounds such as pyridine, N-vinylcaprolactone, and the like.
상기 라디칼 중합성 화합물은, 경화성을 조정하는 등의 관점에서 단관능 라디칼 중합성 화합물과 다관능 라디칼 중합성 화합물을 함유하는 것이 바람직하다. 단관능 라디칼 중합성 화합물만을 사용한 경우, 얻어지는 광 습기 경화형 수지 조성물이 경화성이 떨어지는 것으로 되는 경우가 있고, 다관능 라디칼 중합성 화합물만을 사용한 경우, 얻어지는 광 습기 경화형 수지 조성물이 택성이 떨어지는 것으로 되는 경우가 있다. 그 중에서도, 상기 단관능 라디칼 중합성 화합물로서 분자 중에 질소 원자를 갖는 화합물과, 상기 다관능 라디칼 중합성 화합물로서 우레탄(메트)아크릴레이트를 조합하여 사용하는 것이 보다 바람직하다. 또한, 상기 다관능 라디칼 중합성 화합물은 2 관능 또는 3 관능인 것이 바람직하고, 2 관능인 것이 보다 바람직하다.The radically polymerizable compound preferably contains a monofunctional radically polymerizable compound and a polyfunctional radically polymerizable compound from the viewpoint of adjusting the curability and the like. When only the monofunctional radically polymerizable compound is used, the obtained photo-moisture setting type resin composition may be poor in curability, and when the photo-moisture setting type resin composition is used only in the case of using a polyfunctional radically polymerizable compound, have. Among them, it is more preferable to use a compound having a nitrogen atom in the molecule as a monofunctional radically polymerizable compound and a urethane (meth) acrylate as a combination of the polyfunctional radically polymerizable compound. In addition, the polyfunctional radically polymerizable compound is preferably bifunctional or trifunctional, and more preferably bifunctional.
상기 라디칼 중합성 화합물이 상기 단관능 라디칼 중합성 화합물과 상기 다관능 라디칼 중합성 화합물을 함유하는 경우, 상기 다관능 라디칼 중합성 화합물의 함유량은, 상기 단관능 라디칼 중합성 화합물과 상기 다관능 라디칼 중합성 화합물의 합계 100 중량부에 대하여, 바람직한 하한이 2 중량부, 바람직한 상한이 30 중량부이다. 상기 다관능 라디칼 중합성 화합물의 함유량이 2 중량부 미만이면, 얻어지는 광 습기 경화형 수지 조성물이 경화성이 떨어지는 것으로 되는 경우가 있다. 상기 다관능 라디칼 중합성 화합물의 함유량이 30 중량부를 초과하면, 얻어지는 광 습기 경화형 수지 조성물이 택성이 떨어지는 것으로 되는 경우가 있다. 상기 다관능 라디칼 중합성 화합물의 함유량의 보다 바람직한 하한은 5 중량부, 보다 바람직한 상한은 20 중량부이다.When the radically polymerizable compound contains the monofunctional radically polymerizable compound and the polyfunctional radically polymerizable compound, the content of the polyfunctional radically polymerizable compound is such that the content of the monofunctional radically polymerizable compound and the polyfunctional radical polymerization The preferable lower limit is 2 parts by weight and the preferable upper limit is 30 parts by weight based on 100 parts by weight of the total amount of the compound. When the content of the polyfunctional radically polymerizable compound is less than 2 parts by weight, the resulting photo-moisture-setting type resin composition may be inferior in curability. When the content of the polyfunctional radically polymerizable compound is more than 30 parts by weight, the obtained moisture-curable resin composition may be poor in tackiness. A more preferable lower limit of the content of the polyfunctional radically polymerizable compound is 5 parts by weight, and a more preferable upper limit is 20 parts by weight.
본 발명의 광 습기 경화형 수지 조성물은, 습기 경화형 우레탄 수지를 함유한다. 상기 습기 경화형 우레탄 수지는, 분자 내의 이소시아네이트기가 공기 중 또는 피착체 중의 수분과 반응하여 경화된다. 또한, 습기 경화 성분으로서 가교성 실릴기를 갖는 화합물 등을 사용하는 경우와 비교하여, 얻어지는 광 습기 경화형 수지 조성물은 속경화성이 우수한 것이 된다.The moisture-curing resin composition of the present invention contains a moisture-curing urethane resin. In the moisture-curing urethane resin, an isocyanate group in the molecule is cured by reacting with moisture in the air or the adherend. Further, as compared with the case of using a compound having a crosslinkable silyl group or the like as a moisture-curing component, the resulting photo-moisture-setting type resin composition is excellent in fast curability.
상기 습기 경화형 우레탄 수지는, 1 분자 중에 이소시아네이트기를 1 개만 가지고 있어도 되고, 2 개 이상 가지고 있어도 된다. 그 중에서도, 양 말단에 이소시아네이트기를 갖는 우레탄 프레폴리머인 것이 바람직하다.The moisture-curing urethane resin may have only one isocyanate group in one molecule or two or more isocyanate groups in one molecule. Among them, urethane prepolymers having isocyanate groups at both terminals are preferable.
상기 우레탄 프레폴리머는, 1 분자 중에 2 개 이상의 수산기를 갖는 폴리올 화합물과, 1 분자 중에 2 개 이상의 이소시아네이트기를 갖는 폴리이소시아네이트 화합물을 반응시킴으로써 얻을 수 있다.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.
상기 폴리올 화합물과 폴리이소시아네이트 화합물의 반응은, 통상, 폴리올 화합물 중의 수산기 (OH) 와 폴리이소시아네이트 화합물 중의 이소시아네이트기 (NCO) 의 몰비로 [NCO]/[OH] = 2.0 ∼ 2.5 의 범위에서 행해진다.The reaction between the polyol compound and the polyisocyanate compound is usually carried out in a molar ratio of hydroxyl group (OH) in the polyol compound to isocyanate group (NCO) in the polyisocyanate compound in the range of [NCO] / [OH] = 2.0 to 2.5.
상기 폴리올 화합물로는, 폴리우레탄의 제조에 통상적으로 사용되고 있는 공지된 폴리올 화합물을 사용할 수 있고, 예를 들어, 폴리에스테르폴리올, 폴리에테르폴리올, 폴리알킬렌폴리올, 폴리카보네이트폴리올 등을 들 수 있다. 이들 폴리올 화합물은 단독으로 사용되어도 되고, 2 종 이상을 조합하여 사용되어도 된다.As the polyol compound, known polyol compounds conventionally used in the production of polyurethane can be used, and examples thereof include polyester polyols, polyether polyols, polyalkylene polyols, polycarbonate polyols and the like. These polyol compounds may be used alone or in combination of two or more.
상기 폴리에스테르폴리올로는, 예를 들어, 다가 카르복실산과 폴리올의 반응에 의해 얻어지는 폴리에스테르폴리올이나, ε-카프로락톤을 개환 중합하여 얻어지는 폴리-ε-카프로락톤폴리올 등을 들 수 있다.Examples of the polyester polyol include a polyester polyol obtained by a reaction between a polyvalent carboxylic acid and a polyol, and a poly-epsilon -caprolactone polyol obtained by ring-opening polymerization of? -Caprolactone.
상기 폴리에스테르폴리올의 원료가 되는 상기 다가 카르복실산으로는, 예를 들어, 테레프탈산, 이소프탈산, 1,5-나프탈산, 2,6-나프탈산, 호박산, 글루탈산, 아디프산, 피멜산, 수베르산, 아젤라인산, 세바스산, 데카메틸렌디카르복실산, 도데카메틸렌디카르복실산 등을 들 수 있다.Examples of the polyvalent carboxylic acid which is a raw material of the polyester polyol include terephthalic acid, isophthalic acid, 1,5-naphthalic acid, 2,6-naphthalic acid, succinic acid, glutaric acid, adipic acid, , Suberic acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, dodecamethylene dicarboxylic acid, and the like.
상기 폴리에스테르폴리올의 원료가 되는 상기 폴리올로는, 예를 들어, 에틸렌글리콜, 프로필렌글리콜, 1,3-프로판디올, 1,4-부탄디올, 네오펜틸글리콜, 1,5-펜탄디올, 1,6-헥산디올, 디에틸렌글리콜, 시클로헥산디올 등을 들 수 있다.Examples of the polyol as a raw material of the polyester polyol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6 -Hexanediol, diethylene glycol, cyclohexanediol, and the like.
상기 폴리에테르폴리올로는, 예를 들어, 에틸렌글리콜, 프로필렌글리콜, 테트라하이드로푸란, 3-메틸테트라하이드로푸란의 개환 중합물, 및 이들이나 그 유도체의 랜덤 공중합체 또는 블록 공중합체나, 비스페놀형의 폴리옥시알킬렌 변성체 등을 들 수 있다.Examples of the polyether polyol include random copolymers or block copolymers of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran ring-opening polymerizates and their derivatives, and bisphenol-type poly And oxyalkylene-modified products.
상기 비스페놀형의 폴리옥시알킬렌 변성체는, 비스페놀형 분자 골격의 활성 수소 부분에 알킬렌옥사이드 (예를 들어, 에틸렌옥사이드, 프로필렌옥사이드, 부틸렌옥사이드, 이소부틸렌옥사이드 등) 를 부가 반응시켜 얻어지는 폴리에테르폴리올로서, 랜덤 공중합체여도 되고, 블록 공중합체여도 된다.The bisphenol-type polyoxyalkylene modified product is obtained by subjecting an active hydrogen portion of a bisphenol-type molecular skeleton to an addition reaction with an alkylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) As the polyether polyol, a random copolymer or a block copolymer may be used.
상기 비스페놀형의 폴리옥시알킬렌 변성체는, 비스페놀형 분자 골격의 양 말단에 1 종 또는 2 종 이상의 알킬렌옥사이드가 부가되어 있는 것이 바람직하다. 비스페놀형으로는 특별히 한정되지 않고, A 형, F 형, S 형 등을 들 수 있고, 바람직하게는 비스페놀 A 형이다.In the bisphenol-type polyoxyalkylene modified product, it is preferable that one or more alkylene oxides are added to both ends of the bisphenol-type molecular skeleton. The bisphenol type is not particularly limited, and examples thereof include A type, F type, S type and the like, preferably bisphenol A type.
상기 폴리알킬렌폴리올로는, 예를 들어, 폴리부타디엔폴리올, 수소화 폴리 부타디엔폴리올, 수소화 폴리이소프렌폴리올 등을 들 수 있다.Examples of the polyalkylene polyol include a polybutadiene polyol, a hydrogenated polybutadiene polyol, and a hydrogenated polyisoprene polyol.
상기 폴리카보네이트폴리올로는, 예를 들어, 폴리헥사메틸렌카보네이트폴리올, 폴리시클로헥산디메틸렌카보네이트폴리올 등을 들 수 있다.As the polycarbonate polyol, for example, polyhexamethylene carbonate polyol, polycyclohexanedimethylene carbonate polyol and the like can be given.
상기 폴리이소시아네이트 화합물로는, 예를 들어, 디페닐메탄디이소시아네이트, 디페닐메탄디이소시아네이트의 액상 변성물, 폴리메릭 MDI (메탄 디이소시아네이트), 톨릴렌디이소시아네이트, 나프탈렌-1,5-디이소시아네이트 등을 들 수 있다. 그 중에서도, 증기압이나 독성이 낮은 점, 취급하기 쉬운 점에서 디페닐메탄디이소시아네이트 및 그 변성물이 바람직하다. 상기 폴리이소시아네이트 화합물은 단독으로 사용되어도 되고, 2 종 이상을 조합하여 사용되어도 된다.Examples of the polyisocyanate compound include diphenylmethane diisocyanate, liquid phase modified product of diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like. . Of these, diphenylmethane diisocyanate and its modified products are preferred because of their low vapor pressure and low toxicity and easy handling. These polyisocyanate compounds may be used alone or in combination of two or more.
또한, 상기 습기 경화형 우레탄 수지는, 하기 식 (1) 로 나타내는 구조를 갖는 폴리올 화합물을 사용하여 얻어진 것이 바람직하다. 하기 식 (1) 로 나타내는 구조를 갖는 폴리올 화합물을 사용함으로써, 접착성이 우수한 조성물이나, 유연하고 신장이 좋은 경화물을 얻을 수 있고, 상기 라디칼 중합성 화합물과의 상용성이 우수한 것이 된다.The moisture-curing urethane resin is preferably obtained by using a polyol compound having a structure represented by the following formula (1). By using a polyol compound having a structure represented by the following formula (1), it is possible to obtain a composition having excellent adhesiveness and a cured product having flexibility and elongation, and excellent compatibility with the radical polymerizing compound.
그 중에서도, 프로필렌글리콜이나, 테트라하이드로푸란 (THF) 화합물의 개환 중합 화합물이나, 메틸기 등의 치환기를 갖는 테트라하이드로푸란 화합물의 개환 중합 화합물로 이루어지는 폴리에테르폴리올을 사용하는 것이 바람직하다.Among them, it is preferable to use a polyether polyol comprising a ring-opening polymerization compound of propylene glycol or a tetrahydrofuran (THF) compound or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group.
[화학식 1][Chemical Formula 1]
식 (1) 중, R 은 수소, 메틸기, 또는 에틸기를 나타내고, n 은, 1 ∼ 10 의 정수, L 은 0 ∼ 5 의 정수, m 은 1 ∼ 500 의 정수이다. n 은 1 ∼ 5 인 것이 바람직하고, L 은 0 ∼ 4 인 것이 바람직하고, m 은 50 ∼ 200 인 것이 바람직하다.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. In the formula (1), R represents hydrogen, a methyl group or an ethyl group. n is preferably 1 to 5, L is preferably 0 to 4, and m is preferably 50 to 200.
또한, L 이 0 인 경우란, R 과 결합한 탄소가 직접 산소와 결합하고 있는 경우를 의미한다.When L is 0, it means that the carbon bonded to R is directly bonded to oxygen.
또한, 상기 습기 경화형 우레탄 수지는 라디칼 중합성 관능기를 가지고 있어도 된다.The moisture-curing urethane resin may have a radical polymerizable functional group.
상기 습기 경화형 우레탄 수지가 가지고 있어도 되는 라디칼 중합성 관능기로는, 불포화 2 중 결합을 갖는 기가 바람직하고, 특히 반응성의 면에서 (메트)아크릴로일기가 보다 바람직하다.As the radically polymerizable functional group that the moisture-curable urethane resin may have, a group having an unsaturated double bond is preferable, and a (meth) acryloyl group is more preferable in view of reactivity.
또한, 라디칼 중합성 관능기를 갖는 습기 경화형 우레탄 수지는 라디칼 중합성 화합물에는 포함시키지 않고, 습기 경화형 우레탄 수지로서 취급한다.The moisture-curing urethane resin having a radically polymerizable functional group is not included in the radical polymerizing compound but is treated as a moisture-curing urethane resin.
상기 습기 경화형 우레탄 수지의 중량 평균 분자량의 바람직한 하한은 800, 바람직한 상한은 1 만이다. 상기 습기 경화형 우레탄 수지의 중량 평균 분자량이 800 미만이면, 가교 밀도가 높아져, 유연성이 손상되는 경우가 있다. 상기 습기 경화형 우레탄 수지의 중량 평균 분자량이 1 만을 초과하면, 얻어지는 광 습기 경화형 수지 조성물이 도포성이 떨어지는 것으로 되는 경우가 있다. 상기 습기 경화형 우레탄 수지의 중량 평균 분자량의 보다 바람직한 하한은 2000, 보다 바람직한 상한은 8000, 더욱 바람직한 하한은 3000, 더욱 바람직한 상한은 6000 이다.The preferable lower limit of the weight average molecular weight of the moisture-curing urethane resin is 800, and the upper limit is preferably 10,000. If the weight average molecular weight of the moisture-curing urethane resin is less than 800, the crosslinking density becomes high and the flexibility may be impaired. If the moisture-curable urethane resin has a weight average molecular weight of more than 10,000, the resulting moisture-curable resin composition may have poor applicability. A more preferable lower limit of the weight average molecular weight of the moisture-curing urethane resin is 2000, a more preferable upper limit is 8000, a more preferable lower limit is 3000, and a more preferable upper limit is 6000.
또, 본 명세서에 있어서 상기 중량 평균 분자량은 겔 퍼미에이션 크로마토그래피 (GPC) 에 의해 측정을 실시하여, 폴리스티렌 환산에 의해 구해지는 값이다. GPC 에 의해 폴리스티렌 환산에 의한 중량 평균 분자량을 측정할 때의 칼럼으로는, 예를 들어, Shodex LF-804 (쇼와 전공사 제조) 등을 들 수 있다. 또, GPC 에서 사용하는 용매로는 테트라하이드로푸란 등을 들 수 있다.In the present specification, the weight average molecular weight is a value determined by gel permeation chromatography (GPC) and calculated by polystyrene conversion. As a column for measuring the weight average molecular weight by polystyrene conversion by GPC, for example, Shodex LF-804 (manufactured by Showa Denko K.K.) can be used. As a solvent used in GPC, tetrahydrofuran and the like can be mentioned.
상기 습기 경화형 우레탄 수지의 함유량은, 상기 라디칼 중합성 화합물과 상기 습기 경화형 우레탄 수지의 합계 100 중량부에 대하여, 바람직한 하한이 20 중량부, 바람직한 상한이 90 중량부이다. 상기 습기 경화형 우레탄 수지의 함유량이 20 중량부 미만이면, 얻어지는 광 습기 경화형 수지 조성물이 습기 경화성이 떨어지는 것으로 되는 경우가 있다. 상기 습기 경화형 우레탄 수지의 함유량이 90 중량부를 초과하면, 얻어지는 광 습기 경화형 수지 조성물이 광 경화성이 떨어지는 것으로 되는 경우가 있다. 상기 습기 경화형 우레탄 수지의 함유량의 보다 바람직한 하한은 30 중량부, 보다 바람직한 상한은 75 중량부, 더욱 바람직한 하한은 41 중량부, 더욱 바람직한 상한은 70 중량부이다.The content of the moisture-curing urethane resin is preferably 20 parts by weight, and more preferably 90 parts by weight, based on 100 parts by weight of the total amount of the radically polymerizable compound and the moisture-curing urethane resin. If the content of the moisture-curing urethane resin is less than 20 parts by weight, the resulting moisture-curing resin composition may have poor moisture curability. When the content of the moisture-curing urethane resin exceeds 90 parts by weight, the resulting photo-moisture-setting type resin composition may be inferior in photo-curability. A more preferable lower limit of the content of the moisture-curing 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.
본 발명의 광 습기 경화형 수지 조성물은 광 라디칼 중합 개시제를 함유한다.The photo-moisture-setting type resin composition of the present invention contains a photo radical polymerization initiator.
상기 광 라디칼 중합 개시제로는, 예를 들어, 벤조페논계 화합물, 아세토페논계 화합물, 아실포스핀옥사이드계 화합물, 티타노센계 화합물, 옥심에스테르계 화합물, 벤조인에테르계 화합물, 티오크산톤 등을 들 수 있고, 광 경화성 (심부 경화성) 이 특히 우수한 조성물이 얻어지는 점에서, 아실포스핀옥사이드계 화합물이 바람직하다. 또한, 상기 광 라디칼 중합 개시제는, 상기 서술한 바와 같이 370 ∼ 450 ㎚ 의 파장 영역의 광이 조사됨으로써 감광 가능한 것이 바람직하다.Examples of the photo radical polymerization initiator include a benzophenone based compound, an acetophenone based compound, an acylphosphine oxide based compound, a titanocene based compound, an oxime ester based compound, a benzoin ether based compound, And an acylphosphine oxide-based compound is preferable in that a composition particularly excellent in photo-curability (deep curability) can be obtained. The photo-radical polymerization initiator is preferably photosensitizable by irradiation with light in a wavelength range of 370 to 450 nm as described above.
상기 아실포스핀옥사이드계 화합물로는, 예를 들어, 비스(2,4,6-트리메틸벤조일)-페닐포스핀옥사이드, 2,4,6-트리메틸벤조일디페닐포스핀옥사이드 등을 들 수 있다.Examples of the acylphosphine oxide-based compound include bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
상기 광 라디칼 중합 개시제 중 시판되고 있는 것으로는, 예를 들어, IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE4265, IRGACUREOXE01, 루시린 TPO (모두 BASF Japan 사 제조), 벤조인메틸에테르, 벤조인에틸에테르, 벤조인이소프로필에테르 (모두 도쿄 화성 공업사 제조) 등을 들 수 있다.Examples of commercially available photo radical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE 4265, IRGACUREOXE01, lucylline TPO (all from BASF Japan) Ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.).
상기 광 라디칼 중합 개시제의 함유량은, 상기 라디칼 중합성 화합물 100 중량부에 대하여, 바람직한 하한이 0.01 중량부, 바람직한 상한이 10 중량부이다. 상기 광 라디칼 중합 개시제의 함유량이 0.01 중량부 미만이면, 얻어지는 광 습기 경화형 수지 조성물을 충분히 광 경화시킬 수 없는 경우가 있다. 상기 광 라디칼 중합 개시제의 함유량이 10 중량부를 초과하면, 얻어지는 광 습기 경화형 수지 조성물의 보존 안정성이 저하되는 경우가 있다. 상기 광 라디칼 중합 개시제의 함유량의 보다 바람직한 하한은 0.1 중량부, 보다 바람직한 상한은 5 중량부이다.The content of the photo radical polymerization initiator is preferably 0.01 part by weight, and more preferably 10 parts by weight, based on 100 parts by weight of the radical polymerizable compound. If the content of the photo-radical polymerization initiator is less than 0.01 part by weight, the obtained photo-moisture-setting type resin composition may not be sufficiently photo-cured. If the content of the photo radical polymerization initiator is more than 10 parts by weight, the storage stability of the resulting photo-moisture-setting type resin composition may be deteriorated. A more preferable lower limit of the content of the photo radical polymerization initiator is 0.1 part by weight, and a more preferable upper limit is 5 parts by weight.
본 발명의 광 습기 경화형 수지 조성물은 증감제를 함유해도 된다.The moisture-curing resin composition of the present invention may contain a sensitizer.
본 발명의 광 습기 경화형 수지 조성물은, 상기 증감제를 함유함으로써, 고감도이고 광 경화성이 우수한 광 습기 경화형 수지 조성물을 얻을 수 있다. 상기 증감제는, 상기 서술한 바와 같이 370 ∼ 450 ㎚ 의 파장 영역의 광이 조사됨으로써 증감 효과를 발휘하는 것이 바람직하다.The photo-moisture-setting curable resin composition of the present invention contains the above-mentioned sensitizer, whereby a photo-moisture-setting curable resin composition having high sensitivity and excellent photo-curability can be obtained. As described above, the sensitizer preferably exhibits a sensitizing effect by being irradiated with light in a wavelength range of 370 to 450 nm.
상기 증감제는, 자외·가시 영역에 충분한 광 흡수대를 갖는 것이 바람직한 점에서, 벤조페논 골격, 안트라센 골격, 안트라퀴논 골격, 쿠마린 골격, 티오크산톤 골격, 및 프탈로시아닌 골격으로 이루어지는 군에서 선택되는 적어도 1 종의 골격을 갖는 화합물을 함유하는 것이 바람직하고, 안트라센 골격, 및 안트라퀴논 골격, 티오크산톤 골격으로 이루어지는 군에서 선택되는 적어도 1 종의 골격을 갖는 화합물을 함유하는 것이 보다 바람직하다. 이들 화합물은, 상기 광 라디칼 중합 개시제로서 사용할 수도 있다.The sensitizer is preferably at least one selected from the group consisting of a benzophenone skeleton, an anthracene skeleton, an anthraquinone skeleton, a coumarin skeleton, a thioxanthone skeleton, and a phthalocyanine skeleton in that it is preferable to have a sufficient light absorption band in the ultraviolet / It is preferable to contain a compound having a skeleton of a species and more preferably a compound having at least one skeleton selected from the group consisting of an anthracene skeleton, an anthraquinone skeleton and a thioxanthone skeleton. These compounds may also be used as the photo radical polymerization initiator.
상기 벤조페논 골격을 갖는 화합물로는, 예를 들어, 벤조페논, 2,4-디클로로벤조페논, 4,4'-비스(디메틸아미노)벤조페논, 4,4'-비스(디에틸아미노)벤조페논 등을 들 수 있다.Examples of the compound having a benzophenone skeleton include benzophenone, 2,4-dichlorobenzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) Phenone, and the like.
상기 안트라센 골격을 갖는 화합물로는, 예를 들어, 9,10-디부톡시안트라센, 9,10-디프로폭시안트라퀴논, 9,10-에톡시안트라퀴논 등을 들 수 있다.Examples of the compound having an anthracene skeleton include 9,10-dibutoxyanthracene, 9,10-dipropoxyanthraquinone, and 9,10-ethoxyanthraquinone.
상기 안트라퀴논 골격을 갖는 화합물로는, 예를 들어, 2-에틸안트라퀴논, 1-메틸안트라퀴논, 1,4-디하이드록시안트라퀴논, 2-(2-하이드록시에톡시)-안트라퀴논 등을 들 수 있다.Examples of the compound having an anthraquinone skeleton include 2-ethyl anthraquinone, 1-methyl anthraquinone, 1,4-dihydroxy anthraquinone, 2- (2-hydroxyethoxy) .
상기 쿠마린 골격을 갖는 화합물로는, 예를 들어, 7-디에틸아미노-4-메틸쿠마린 등을 들 수 있다.Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin and the like.
상기 티오크산톤 골격을 갖는 화합물로는, 예를 들어, 2,4-디에틸티오크산톤, 2-클로로티오크산톤, 4-이소프로필티오크산톤, 1-클로로-4-프로필티오크산톤 등을 들 수 있다.Examples of the compound having a thioxanthone skeleton include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propylthioxanthone And the like.
상기 프탈로시아닌 골격을 갖는 화합물로는, 예를 들어, 프탈로시아닌 등을 들 수 있다.Examples of the compound having a phthalocyanine skeleton include phthalocyanine and the like.
이들 증감제 중에서도, 얻어지는 광 습기 경화형 수지 조성물이 차광부의 경화성이 특히 우수한 것이 되는 점에서, 4,4'-비스(디메틸아미노)벤조페논 및 4,4'-비스(디에틸아미노)벤조페논 중 적어도 어느 하나가 바람직하게 사용된다.Among these sensitizers, from the viewpoint that the obtained light moisture-setting type resin composition is particularly excellent in the curing property of the light-shielding portion, it is preferred to use 4,4'-bis (dimethylamino) benzophenone and 4,4'- Is preferably used.
상기 증감제의 함유량은, 상기 광 중합 개시제 100 중량부에 대하여, 바람직한 하한이 2 중량부, 바람직한 상한이 50 중량부이다. 상기 증감제의 함유량이 2 중량부 미만이면, 증감 효과가 충분히 발휘되지 않는 경우가 있다. 상기 증감제의 함유량이 50 중량부를 초과하면, 얻어지는 광 습기 경화형 수지 조성물의 보존 안정성이 저하되는 경우가 있다. 상기 증감제의 함유량의 보다 바람직한 하한은 5 중량부, 보다 바람직한 상한은 40 중량부이다.The content of the sensitizer is preferably 2 parts by weight, and more preferably 50 parts by weight, based on 100 parts by weight of the photopolymerization initiator. If the content of the sensitizer is less than 2 parts by weight, the effect of increasing or decreasing may not be sufficiently exhibited. When the content of the sensitizer exceeds 50 parts by weight, the storage stability of the obtained moisture-curable resin composition may be deteriorated. A more preferable lower limit of the content of the sensitizer is 5 parts by weight, and a more preferable upper limit is 40 parts by weight.
본 발명의 광 습기 경화형 수지 조성물은, 얻어지는 광 습기 경화형 수지 조성물의 도포성이나 형상 유지성을 조정하는 등의 관점에서 충전제를 함유해도 된다. 상기 충전제를 함유함으로써, 본 발명의 광 습기 경화형 수지 조성물은 바람직한 틱소성을 갖는 것으로 되어, 도포 후의 형상을 충분히 유지할 수 있다.The photo-moisture-setting type resin composition of the present invention may contain a filler in view of adjusting the coatability and shape-retaining property of the resultant photo-moisture-setting type resin composition. By containing the filler, the photo-moisture hardening type resin composition of the present invention has a favorable tack plasticity, and the shape after application can be sufficiently maintained.
상기 충전제는, 일차 입자 직경의 바람직한 하한이 1 ㎚, 바람직한 상한이 50 ㎚ 이다. 상기 충전제의 일차 입자 직경이 1 ㎚ 미만이면, 얻어지는 광 습기 경화형 수지 조성물이 도포성이 떨어지는 것으로 되는 경우가 있다. 상기 충전제의 일차 입자 직경이 50 ㎚ 를 초과하면, 얻어지는 광 습기 경화형 수지 조성물이 도포 후의 형상 유지성이 떨어지는 것으로 되는 경우가 있다. 상기 충전제의 일차 입자 직경의 보다 바람직한 하한은 5 ㎚, 보다 바람직한 상한은 30 ㎚, 더욱 바람직한 하한은 10 ㎚, 더욱 바람직한 상한은 20 ㎚ 이다.The filler preferably has a lower limit of the primary particle diameter of 1 nm and a preferable upper limit of 50 nm. If the primary particle diameter of the filler is less than 1 nm, the resulting photo-moisture-setting type resin composition may have poor applicability. When the primary particle diameter of the filler is more than 50 nm, the resulting moisture-setting and curing-type resin composition may be inferior in shape retention after application. A more preferable lower limit of the primary particle diameter of the filler is 5 nm, a more preferable upper limit is 30 nm, a still more preferable lower limit is 10 nm, and a still more preferable upper limit is 20 nm.
또, 상기 충전제의 일차 입자 직경은, NICOMP 380ZLS (PARTICLE SIZING SYSTEMS 사 제조) 를 사용하여, 상기 충전제를 용매 (물, 유기 용매 등) 에 분산시켜 측정할 수 있다.The primary particle diameter of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
또한, 상기 충전제는, 본 발명의 광 습기 경화형 수지 조성물 중에 있어서 이차 입자 (일차 입자가 복수 모인 것) 로서 존재하는 경우가 있고, 이러한 이차 입자의 입자 직경의 바람직한 하한은 5 ㎚, 바람직한 상한은 500 ㎚, 보다 바람직한 하한은 10 ㎚, 보다 바람직한 상한은 100 ㎚ 이다. 상기 충전제의 이차 입자의 입자 직경은, 본 발명의 광 습기 경화형 수지 조성물 또는 그 경화물을 투과형 전자현미경 (TEM) 을 사용하여 관찰함으로써 측정할 수 있다.The filler may exist as secondary particles (having a plurality of primary particles) in the moisture-curable resin composition of the present invention. The preferable lower limit of the particle diameter of such secondary particles is 5 nm, and the preferable upper limit is 500 Nm, a more preferred lower limit is 10 nm, and a more preferable upper limit is 100 nm. The particle diameter of the secondary particle of the filler can be measured by observing the photo-moisture-setting resin composition or the cured product of the present invention using a transmission electron microscope (TEM).
상기 충전제로는, 무기 충전제가 바람직하고, 예를 들어, 실리카, 탤크, 산화티탄, 산화아연, 탄산칼슘 등을 들 수 있다. 그 중에서도, 얻어지는 광 습기 경화형 수지 조성물이 UV 광 투과성이 우수한 것으로 되는 점에서 실리카가 바람직하다. 이들 충전제는 단독으로 사용되어도 되고, 2 종 이상을 조합하여 사용되어도 된다.As the filler, an inorganic filler is preferable, and examples thereof include silica, talc, titanium oxide, zinc oxide, calcium carbonate, and the like. Among them, silica is preferable in that the obtained moisture-curing resin composition is excellent in UV light transmittance. These fillers may be used alone or in combination of two or more.
상기 충전제는, 소수성 표면 처리가 이루어져 있는 것이 바람직하다. 상기 소수성 표면 처리에 의해, 얻어지는 광 습기 경화형 수지 조성물이 도포 후의 형상 유지성이 보다 우수한 것이 된다.The filler is preferably subjected to a hydrophobic surface treatment. By the hydrophobic surface treatment, the resulting moisture-curable resin composition obtained is more excellent in shape retention after application.
상기 소수성 표면 처리로는, 실릴화 처리, 알킬화 처리, 에폭시화 처리 등을 들 수 있다. 그 중에서도, 형상 유지성을 향상시키는 효과가 우수한 점에서 실릴화 처리가 바람직하고, 트리메틸실릴화 처리가 보다 바람직하다.Examples of the hydrophobic surface treatment include a silylation treatment, an alkylation treatment, and an epoxidation treatment. Of these, the silylation treatment is preferable, and the trimethylsilylation treatment is more preferable because of the excellent effect of improving the shape retentivity.
상기 충전제를 소수성 표면 처리하는 방법으로는, 예를 들어, 실란 커플링제 등의 표면 처리제를 사용하여 충전제의 표면을 처리하는 방법 등을 들 수 있다.The hydrophobic surface treatment of the filler includes, for example, a method of treating the surface of the filler using a surface treatment agent such as a silane coupling agent.
구체적으로는 예를 들어, 상기 트리메틸실릴화 처리 실리카는, 예를 들어, 실리카를 졸겔법 등의 방법으로 합성하고, 실리카를 유동시킨 상태에서 헥사메틸디실라잔을 분무하는 방법이나, 알코올, 톨루엔 등의 유기 용매 중에 실리카를 첨가하고, 헥사메틸디실라잔과 물을 첨가한 후, 물과 유기 용매를 이배퍼레이터에 의해 증발 건조시키는 방법 등에 의해 제조할 수 있다.Specifically, for example, the trimethylsilylation-treated silica can be produced by, for example, synthesizing silica by a method such as a sol-gel method, spraying hexamethyldisilazane in a state in which silica is flowing, Or the like, adding hexamethyldisilazane and water, and then evaporating the water and the organic solvent by evaporator to dryness.
상기 충전제의 함유량은, 본 발명의 광 습기 경화형 수지 조성물 전체 100 중량부 중에 있어서, 바람직한 하한이 0.1 중량부, 바람직한 상한이 20 중량부이다. 상기 충전제의 함유량이 0.1 중량부 미만이면, 얻어지는 광 습기 경화형 수지 조성물이 도포 후의 형상 유지성이 떨어지는 것으로 되는 경우가 있다. 상기 충전제의 함유량이 20 중량부를 초과하면, 얻어지는 광 습기 경화형 수지 조성물이 도포성이 떨어지는 것으로 되는 경우가 있다. 상기 충전제의 함유량의 보다 바람직한 하한은 0.5 중량부, 보다 바람직한 상한은 15 중량부이고, 더욱 바람직한 하한은 1 중량부, 더욱 바람직한 상한은 12 중량부, 특히 바람직한 하한은 2 중량부이다.The content of the filler is preferably 0.1 part by weight, and more preferably 20 parts by weight, in 100 parts by weight of the total amount of the moisture-curable resin composition of the present invention. If the content of the filler is less than 0.1 part by weight, the resulting photo-moisture-setting type resin composition may be inferior in shape retention after application. When the content of the filler is more than 20 parts by weight, the resulting photo-moisture-setting type resin composition may have poor applicability. More preferably, the lower limit of the content of the filler is 0.5 parts by weight, and the more preferred upper limit is 15 parts by weight, more preferably 1 part by weight, still more preferably 12 parts by weight, particularly preferably 2 parts by weight.
본 발명의 광 습기 경화형 수지 조성물은, 추가로 필요에 따라서, 이온 액체, 용제, 금속 함유 입자, 반응성 희석제 등의 첨가제를 함유해도 된다.The moisture-curing resin composition of the present invention may further contain an additive such as an ionic liquid, a solvent, a metal-containing particle, and a reactive diluent, if necessary.
본 발명의 광 습기 경화형 수지 조성물을 제조하는 방법으로는, 예를 들어, 호모디스퍼, 호모믹서, 만능 믹서, 플래니터리 믹서, 니더, 3 개 롤 등의 혼합기를 사용하여, 라디칼 중합성 화합물과, 습기 경화형 우레탄 수지와, 광 라디칼 중합 개시제와, 차광제와, 필요에 따라서 첨가하는 첨가제를 혼합하는 방법 등을 들 수 있다.As a method of producing the photo-moisture-setting type resin composition of the present invention, a radical polymerizing compound (for example, a homopolymer or a mixture thereof) is prepared by using a mixer such as homodisperse, homomixer, universal mixer, planetary mixer, kneader, , A method of mixing a moisture-curing urethane resin, a photo-radical polymerization initiator, a light-shielding agent, and an additive to be added as required.
본 발명의 광 습기 경화형 수지 조성물은, 광 조사에 의해 신속히 경화시키고, 추가로 습기 경화시킴으로써 충분히 경화시킬 수 있다.The photo-moisture-setting type resin composition of the present invention can be sufficiently cured by rapidly curing by light irradiation and further by moisture curing.
또한, 본 발명의 광 습기 경화형 수지 조성물을 광 경화시킬 때에 사용되는 광원으로는, 일반적으로 사용되는 고압 수은 램프나 메탈 할라이드 램프뿐만 아니라, LED 방식의 광원도 사용하는 것이 가능하다.As a light source used for photo-curing the photo-moisture-setting type resin composition of the present invention, not only a commonly used high-pressure mercury lamp or metal halide lamp but also an LED-based light source can be used.
본 발명의 광 습기 경화형 수지 조성물은, 경화 후의 1 ㎜ 두께의 경화물의 광학 농도 (OD 값) 가 1 이상인 것이 바람직하다. 상기 OD 값이 1 미만이면, 차광성이 불충분해져, 표시 소자에 사용한 경우에 광의 누설이 발생하여, 높은 콘트라스트를 얻을 수 없는 경우가 있다. 상기 OD 값은 1.5 이상인 것이 보다 바람직하다.The optically moisture-curable resin composition of the present invention preferably has an optical density (OD value) of 1 or more of a cured product having a thickness of 1 mm after curing. If the OD value is less than 1, the light shielding property becomes insufficient, light leakage occurs when used for a display element, and high contrast may not be obtained in some cases. The OD value is more preferably 1.5 or more.
상기 OD 값은 높을수록 좋지만, 상기 OD 값을 높게 하기 위해서 차광제를 지나치게 많이 배합하면, 증점에 의한 작업성의 저하 등이 발생하는 점에서, 차광제의 배합량과의 밸런스를 맞추기 위해, 상기 경화체의 OD 값의 바람직한 상한은 4 이다.The OD value is preferably as high as possible. However, in order to balance the amount of the light-shielding agent with the amount of the light-shielding agent in view of lowering of workability due to thickening when too much light-shielding agent is added in order to raise the OD value, The preferred upper limit of the OD value is 4.
또한, 상기 광 습기 경화형 수지 조성물의 경화 후의 OD 값은, 광학 농도계를 사용하여 측정할 수 있다. 상기 OD 값을 측정하는 경화물은, 고압 수은 램프 등을 사용하여 500 mJ/㎠ 의 자외선을 조사함으로써 얻을 수 있다.The OD value after curing of the above moisture-curing resin composition can be measured using an optical densitometer. The cured product for measuring the OD value can be obtained by irradiating ultraviolet rays at 500 mJ /
본 발명의 광 습기 경화형 수지 조성물에 있어서의, 콘플레이트형 점도계를 사용하여 25 ℃, 1 rpm 의 조건으로 측정한 점도의 바람직한 하한은 50 ㎩·s, 바람직한 상한은 500 ㎩·s 이다. 상기 점도가 50 ㎩·s 미만이거나, 500 ㎩·s 를 초과하거나 하면, 광 습기 경화형 수지 조성물을 전자 부품용 접착제나 표시 소자용 접착제에 사용하는 경우에 기판 등의 피착체에 도포할 때의 작업성이 나빠지는 경우가 있다. 상기 점도의 보다 바람직한 하한은 80 ㎩·s, 보다 바람직한 상한은 300 ㎩·s, 더욱 바람직한 상한은 200 ㎩·s 이다.The preferable lower limit of the viscosity measured at 25 캜 and 1 rpm using a cone plate type viscometer in the photo-moisture-setting type resin composition of the present invention is 50 Pa · s, and the preferred upper limit is 500 Pa · s. When the viscosity of the resin composition is less than 50 Pa · s or more than 500 Pa · s, when the optical moisture-curable resin composition is used for an adhesive for electronic parts or an adhesive for a display element, There is a case that the sex is bad. A more preferred lower limit of the viscosity is 80 Pa s, a more preferable upper limit is 300 Pa s, and a more preferable upper limit is 200 Pa s.
본 발명의 광 습기 경화형 수지 조성물의 틱소트로픽 인덱스의 바람직한 하한은 1.3, 바람직한 상한은 5.0 이다. 상기 틱소트로픽 인덱스가 1.3 미만이거나, 5.0 을 초과하거나 하면, 광 습기 경화형 수지 조성물을 전자 부품용 접착제나 표시 소자용 접착제에 사용하는 경우에 기판 등의 피착체에 도포할 때의 작업성이 나빠지는 경우가 있다. 상기 틱소트로픽 인덱스의 보다 바람직한 하한은 1.5, 보다 바람직한 상한은 4.0 이다.The preferred lower limit of the thixotropic index of the moisture-curable resin composition of the present invention is 1.3, and the upper limit is preferably 5.0. When the above-mentioned thixotropic index is less than 1.3 or more than 5.0, when the optical moisture-curable resin composition is used for an adhesive for electronic parts or an adhesive for a display element, the workability when applied to an adherend such as a substrate is poor There is a case. A more preferable lower limit of the thixotropic index is 1.5, and a more preferable upper limit is 4.0.
또한, 본 명세서에 있어서 상기 틱소트로픽 인덱스란, 콘플레이트형 점도계를 사용하여 25 ℃, 1 rpm 의 조건으로 측정한 점도를, 콘플레이트형 점도계를 사용하여 25 ℃, 10 rpm 의 조건으로 측정한 점도로 나눈 값을 의미한다.In the present specification, the thixotropic index refers to a viscosity measured at 25 캜 and 1 rpm using a cone plate viscometer under the conditions of 25 캜 and 10 rpm using a cone plate viscometer . ≪ / RTI >
본 발명의 광 습기 경화형 수지 조성물은, 전자 부품용 접착제나 표시 소자용 접착제로서 특히 바람직하게 사용할 수 있다. 본 발명의 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제, 및 본 발명의 광 습기 경화형 수지 조성물을 사용하여 이루어지는 표시 소자용 접착제도 또한, 각각 본 발명의 하나이다.The moisture-curable resin composition of the present invention can be particularly preferably used as an adhesive for electronic parts or an adhesive for display elements. The adhesive for electronic parts using the photo-moisture-curable resin composition of the present invention and the adhesive for a display element using the photo-moisture-curable resin composition of the present invention are also one of the present invention.
본 발명에 의하면, 차광성 및 접착성이 우수한 광 습기 경화형 수지 조성물을 제공할 수 있다.According to the present invention, it is possible to provide a light moisture curable resin composition excellent in light shielding property and adhesive property.
도 1(a) 는, 접착성 평가용 샘플을 위에서 본 경우를 나타내는 모식도이고, 1(b) 는, 접착성 평가용 샘플을 옆에서 본 경우를 나타내는 모식도이다.1 (a) is a schematic view showing a case where the adhesive property evaluation sample is viewed from above, and 1 (b) is a schematic view showing a case where the adhesive property evaluation sample is viewed from the side.
이하에 실시예를 들어 본 발명을 더욱 상세하게 설명하지만, 본 발명은 이들 실시예에만 한정되지 않는다. 또, 본 발명에 의하면, 그 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제 및 표시 소자용 접착제를 제공할 수 있다.Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. Further, according to the present invention, it is possible to provide an adhesive for an electronic part and an adhesive for a display element which are formed by using the moisture-curing resin composition.
(합성예 1 (우레탄 프레폴리머 A 의 제조))(Synthesis Example 1 (Production of urethane prepolymer A)
폴리올로서 100 중량부의 폴리테트라메틸렌에테르글리콜 (미츠비시 화학사 제조, 「PTMG-2000」) 과, 0.01 중량부의 디부틸주석디라우레이트를 500 ㎖ 용량의 세퍼러블 플라스크에 넣고, 진공하 (20 ㎜Hg 이하), 100 ℃ 에서 30 분간 교반하여 혼합하였다. 그 후 상압으로 하여, 디이소시아네이트로서 26.5 중량부의 Pure MDI (닛소 쇼지사 제조) 를 넣고, 80 ℃ 에서 3 시간 교반하여 반응시켜, 우레탄 프레폴리머 A (중량 평균 분자량 2700) 를 얻었다.100 parts by weight of polytetramethylene ether glycol ("PTMG-2000" manufactured by Mitsubishi Chemical Corporation) as a polyol and 0.01 parts by weight of dibutyltin dilaurate were placed in a separable flask having a capacity of 500 ml, ), And they were mixed by stirring at 100 DEG C for 30 minutes. Thereafter, 26.5 parts by weight of Pure MDI (manufactured by Nisso Shoji Co., Ltd.) as a diisocyanate was added and reacted at 80 ° C for 3 hours with stirring to obtain a urethane prepolymer A (weight average molecular weight: 2700).
(합성예 2 (우레탄 프레폴리머 B 의 제조))(Synthesis Example 2 (Production of urethane prepolymer B)
폴리올로서 100 중량부의 폴리프로필렌글리콜 (아사히 가라스사 제조, 「EXCENOL 2020」) 과, 0.01 중량부의 디부틸주석디라우레이트를 500 ㎖ 용량의 세퍼러블 플라스크에 넣고, 진공하 (20 ㎜Hg 이하), 100 ℃ 에서 30 분간 교반하여 혼합하였다. 그 후 상압으로 하여, 디이소시아네이트로서 26.5 중량부의 Pure MDI (닛소 쇼지사 제조) 를 넣고, 80 ℃ 에서 3 시간 교반하여 반응시켜, 우레탄 프레폴리머 B (중량 평균 분자량 2900) 를 얻었다.100 parts by weight of polypropylene glycol ("EXCENOL 2020" manufactured by Asahi Glass Co., Ltd.) and 0.01 part by weight of dibutyltin dilaurate were placed as a polyol into a 500 ml separable flask, Followed by stirring at 100 DEG C for 30 minutes. Thereafter, 26.5 parts by weight of Pure MDI (manufactured by Nisso Shoji Co., Ltd.) as a diisocyanate was added and reacted at 80 ° C for 3 hours with stirring to obtain a urethane prepolymer B (weight average molecular weight: 2900).
(합성예 3 (우레탄 프레폴리머 C 의 제조))(Synthesis Example 3 (Production of urethane prepolymer C))
합성예 1 과 동일하게 하여 얻은 우레탄 프레폴리머 A 가 들어 있는 반응 용기에, 하이드록시에틸메타크릴레이트 1.3 중량부와, 중합 금지제로서 N-니트로소페닐하이드록실아민알루미늄염 (와코 쥰야쿠 공업사 제조, 「Q-1301」) 0.14 중량부를 첨가하고, 질소 기류하, 80 ℃ 에서 1 시간 교반 혼합하여, 분자 말단에 이소시아네이트기와 메타크릴로일기를 갖는 우레탄 프레폴리머 C (중량 평균 분자량 3100) 를 얻었다.To a reaction vessel containing the urethane prepolymer A obtained in the same manner as in Synthesis Example 1, 1.3 parts by weight of hydroxyethyl methacrylate and 50 parts by weight of N-nitrosophenylhydroxylamine aluminum salt (manufactured by Wako Pure Chemical Industries, Ltd.) , "Q-1301") were added and mixed under agitation in a nitrogen stream at 80 ° C for 1 hour to obtain urethane prepolymer C (weight average molecular weight: 3100) having isocyanate group and methacryloyl group at the molecular end.
(실시예 1 ∼ 16, 비교예 1, 2)(Examples 1 to 16 and Comparative Examples 1 and 2)
표 1, 2 에 기재된 배합비에 따라서, 각 재료를 유성식 교반 장치 (씽키사 제조, 「아와토리 렌타로」) 로 교반한 후, 세라믹 3 개 롤에 의해 균일하게 혼합하여 실시예 1 ∼ 16, 비교예 1, 2 의 광 습기 경화형 수지 조성물을 얻었다.Each of the materials was stirred with a planetary-type stirring device ("Awatolian Taro" manufactured by Singkis) according to the blending ratios shown in Tables 1 and 2, and then uniformly mixed with three rolls of ceramic to obtain Examples 1 to 16, To obtain a light moisture-curing resin composition of Comparative Examples 1 and 2.
또한, 표 1 에 있어서의 「우레탄 프레폴리머 A」는 합성예 1 에 기재한 양 말단에 이소시아네이트기를 갖는 우레탄 프레폴리머이고, 「우레탄 프레폴리머 B」는 합성예 2 에 기재한 양 말단에 이소시아네이트기를 갖는 우레탄 프레폴리머이고, 「우레탄 프레폴리머 C」는 합성예 3 에 기재한 분자 말단에 이소시아네이트기와 메타크릴로일기를 갖는 우레탄 프레폴리머이다."Urethane prepolymer A" in Table 1 is a urethane prepolymer having isocyanate groups at both terminals described in Synthesis Example 1, and "urethane prepolymer B" is a urethane prepolymer having isocyanate groups at both terminals described in Synthesis Example 2 Urethane prepolymer C "is a urethane prepolymer having an isocyanate group and a methacryloyl group at the molecular terminals described in Synthesis Example 3.
<평가><Evaluation>
실시예 및 비교예에서 얻어진 각 광 습기 경화형 수지 조성물에 대해서 이하의 평가를 실시하였다. 결과를 표 1, 2 에 나타내었다.The following evaluations were carried out for each of the moisture-curing resin compositions obtained in Examples and Comparative Examples. The results are shown in Tables 1 and 2.
(차광성 (OD 값))(Light shielding property (OD value))
실시예 및 비교예에서 얻어진 각 광 습기 경화형 수지 조성물을, 1 ㎜ 두께의 테플론 (등록상표) 소편을 갭제로 하는 이형 (離型) 폴리에틸렌테레프탈레이트 (PET) 상에 도포하고, 그 위에 추가로 이형 PET 를 중첩하여, 유리로 눌러 균일한 두께로 한 후, 고압 수은 램프를 사용하여 500 mJ/㎠ 의 자외선을 조사함으로써, 광 습기 경화형 수지 조성물을 광 경화시켰다.Each of the light moisture and moisture curable resin compositions obtained in Examples and Comparative Examples was coated on a release polyethylene terephthalate (PET) having a 1-mm-thick Teflon (registered trademark) piece as a gap gap, The PET was superimposed, pressed with glass to a uniform thickness, and irradiated with ultraviolet light of 500 mJ / cm < 2 > using a high-pressure mercury lamp to photo-cure the light moisture curable resin composition.
그 후, 하룻밤 방치함으로써 습기 경화시켜, 1 ㎜ 두께의 차광성 평가용 샘플을 얻었다.Thereafter, the sample was allowed to stand overnight to be moisture-cured to obtain a sample for evaluation of light blocking property with a thickness of 1 mm.
얻어진 차광성 평가용 샘플에 대하여, 광학 농도계 (X-rite 사 제조, 「스펙트로미터」) 를 사용하여 광학 농도 (OD 값) 를 측정하였다.Optical density (OD value) of the obtained light-shielding property evaluation sample was measured using an optical densitometer (X-rite, "Spectrometer").
(접착성)(Adhesive property)
실시예 및 비교예에서 얻어진 각 광 습기 경화형 수지 조성물을, 디스펜스 장치를 사용하여 폴리카보네이트 기판에 약 2 ㎜ 의 폭으로 도포하였다. 그 후, 고압 수은 램프를 사용하여 500 mJ/㎠ 의 자외선을 조사함으로써, 광 습기 경화형 수지 조성물을 광 경화시켰다.Each of the light moisture and moisture curable resin compositions obtained in Examples and Comparative Examples was applied to a polycarbonate substrate with a width of about 2 mm using a dispensing apparatus. Thereafter, the photo-moisture-setting type resin composition was photo-cured by irradiating ultraviolet rays of 500 mJ /
그 후, 폴리카보네이트 기판에 유리판을 첩합 (貼合) 하고, 하룻밤 방치함으로써 습기 경화시켜, 접착성 평가용 샘플을 얻었다.Thereafter, a glass plate was bonded to the polycarbonate substrate, and left to stand overnight to be moisture-cured to obtain a sample for evaluation of adhesion.
도 1 에 접착성 평가용 샘플을 위에서 본 경우를 나타내는 모식도 (도 1(a)), 및 접착성 평가용 샘플을 옆에서 본 경우를 나타내는 모식도 (도 1(b)) 를 나타내었다.Fig. 1 shows a schematic view (Fig. 1 (a)) showing a case where the adhesive property evaluation sample was seen from above, and a schematic diagram showing a case where the adhesive property evaluation sample was viewed from the side (Fig. 1 (b)).
제조한 접착성 평가용 샘플을 인장 시험기를 사용하여 전단 방향으로 5 ㎜/sec 의 속도로 인장하여, 기재가 박리될 때의 강도를 측정하였다.The thus-prepared sample for adhesion evaluation was stretched at a rate of 5 mm / sec in the shearing direction using a tensile tester to measure the strength at the time of delamination of the substrate.
(심부 경화성)(Deep curing property)
실시예 및 비교예에서 얻어진 각 광 습기 경화형 수지 조성물을, 디스펜스 장치를 사용하여 폴리카보네이트 기판에 약 2 ㎜ 의 폭으로 도포하였다. 그 후, 고압 수은 램프를 사용하여 500 mJ/㎠ 의 자외선을 조사함으로써, 광 습기 경화형 수지 조성물을 광 경화시켜, 심부 경화성 평가용 샘플을 제조하였다. 얻어진 심부 경화성 평가용 샘플을, 아세톤을 깊이 스며들게 한 부직포 (아사히 카세이 섬유사 제조, 「벤코트」) 로 문질렀을 때에, 기판으로부터 경화물 전체가 간단히 떨어지는 (심부 경화되어 있지 않은) 것을 「×」, 기판에 경화물이 일부 남은 것 (심부 경화 일부 되어 있는) 을 「△」, 기판에 경화물이 대부분 남은 것 (거의 심부 경화되어 있는) 을 「○」, 기판으로부터 경화물이 전혀 떨어지지 않았던 것 (심부 경화되어 있는) 을 「◎」로 하여 심부 경화성을 평가하였다.Each of the light moisture and moisture curable resin compositions obtained in Examples and Comparative Examples was applied to a polycarbonate substrate with a width of about 2 mm using a dispensing apparatus. Thereafter, a light moisture curable resin composition was photo-cured by irradiating ultraviolet rays of 500 mJ / cm < 2 > using a high-pressure mercury lamp to prepare a sample for evaluating deep portion curability. When the obtained deep curing property evaluation sample was rubbed with a nonwoven fabric ("Ben Coat", manufactured by Asahi Kasei Fibers Ltd.) deeply impregnated with acetone, "x" indicating that the entire cured product was easily separated from the substrate , &Quot; DELTA ", " DELTA ", " DELTA ", " DELTA ", and " (Deep-cured) was evaluated as " ", and the deep-part curability was evaluated.
산업상 이용가능성Industrial availability
본 발명에 의하면, 차광성 및 접착성이 우수한 광 습기 경화형 수지 조성물을 제공할 수 있다. 또한, 본 발명에 의하면, 그 광 습기 경화형 수지 조성물을 사용하여 이루어지는 전자 부품용 접착제 및 표시 소자용 접착제를 제공할 수 있다.According to the present invention, it is possible to provide a light moisture curable resin composition excellent in light shielding property and adhesive property. Further, according to the present invention, it is possible to provide an adhesive for an electronic part and an adhesive for a display element, each of which is formed by using the moisture-curable resin composition.
1 : 폴리카보네이트 수지 기판
2 : 광 습기 경화형 수지 조성물
3 : 유리판1: Polycarbonate resin substrate
2: light moisture-curable resin composition
3: Glass plate
Claims (8)
경화 후의 1 ㎜ 두께의 경화물의 OD 값이 1 이상인 것을 특징으로 하는 광 습기 경화형 수지 조성물.The method according to claim 1,
Wherein the OD value of the cured product of 1 mm thickness after curing is 1 or more.
라디칼 중합성 화합물은, 단관능 라디칼 중합성 화합물과 다관능 라디칼 중합성 화합물을 함유하는 것을 특징으로 하는 광 습기 경화형 수지 조성물.3. The method according to claim 1 or 2,
Wherein the radically polymerizable compound contains a monofunctional radically polymerizable compound and a polyfunctional radically polymerizable compound.
증감제를 함유하는 것을 특징으로 하는 광 습기 경화형 수지 조성물.The method according to claim 1, 2, or 3,
And a photosensitizer, and a sensitizer.
광 라디칼 중합 개시제는, 아실포스핀옥사이드계 화합물인 것을 특징으로 하는 광 습기 경화형 수지 조성물.The method according to claim 1, 2, 3, or 4,
Wherein the photoradical polymerization initiator is an acylphosphine oxide-based compound.
일차 입자 직경이 1 ∼ 50 ㎚ 인 충전제를 함유하는 것을 특징으로 하는 광 습기 경화형 수지 조성물.The method of claim 1, 2, 3, 4, or 5,
And a filler having a primary particle diameter of 1 to 50 nm.
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