KR20230067334A - UV Curable Adhesive and Heterogeneous Bonding Sheet Containing Same - Google Patents
UV Curable Adhesive and Heterogeneous Bonding Sheet Containing Same Download PDFInfo
- Publication number
- KR20230067334A KR20230067334A KR1020210153332A KR20210153332A KR20230067334A KR 20230067334 A KR20230067334 A KR 20230067334A KR 1020210153332 A KR1020210153332 A KR 1020210153332A KR 20210153332 A KR20210153332 A KR 20210153332A KR 20230067334 A KR20230067334 A KR 20230067334A
- Authority
- KR
- South Korea
- Prior art keywords
- curable adhesive
- acrylate
- photoinitiator
- adhesive
- heterojunction
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 64
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 72
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 239000000654 additive Substances 0.000 claims abstract description 14
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000000996 additive effect Effects 0.000 claims abstract description 10
- 230000000903 blocking effect Effects 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 27
- -1 Acryl Chemical group 0.000 claims description 26
- 239000012790 adhesive layer Substances 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 239000005341 toughened glass Substances 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 239000011242 organic-inorganic particle Substances 0.000 claims description 2
- 238000004383 yellowing Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000003287 optical effect Effects 0.000 abstract description 5
- 238000005187 foaming Methods 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 238000001723 curing Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 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 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 2
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 239000011358 absorbing material Substances 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 125000006226 butoxyethyl group Chemical group 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- YQUQWHNMBPIWGK-UHFFFAOYSA-N p-isopropyl-phenol Natural products CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/20—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself
- C09J2301/208—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive itself the adhesive layer being constituted by at least two or more adjacent or superposed adhesive layers, e.g. multilayer adhesive
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
개시된 내용은 UV 경화형 접착제 및 이를 포함하는 이종 접합시트에 관한 것이다.The disclosed content relates to a UV curable adhesive and a heterojunction sheet including the same.
본 명세서에서 달리 표시되지 않는 한, 이 식별항목에 설명되는 내용들은 이 출원의 청구항들에 대한 종래 기술이 아니며, 이 식별항목에 기재된다고 하여 종래 기술이라고 인정되는 것은 아니다. Unless otherwise indicated herein, material described in this section is not prior art to the claims in this application, and it is not admitted that the material described in this section is prior art.
이종 접합시트는 수지와 수지, 수지와 유리, 유리와 유리 사이에 접착력이 강한 접착층을 삽입하여 수지층의 황변성 등이나 유리의 쉽게 깨지기 쉬운 물성 및 높은 비중 등을 보완하기 위한 목적으로 만든 시트로써 충격흡수력이 매우 우수하여 쉽게 파손되지 않으며, 외부에서 가해지는 충격으로 인해 시트가 파손되더라도 필름이 유리 파편을 붙잡아 유리 파편이 비산되지 않도록 하여 추가적인 피해를 방지할 수 있는 특징을 가지고 있다. Heterogeneous bonding sheet is a sheet made for the purpose of supplementing the yellowing of the resin layer or the easily breakable physical properties and high specific gravity of glass by inserting an adhesive layer with strong adhesive strength between resin and resin, resin and glass, and glass. It has excellent shock absorption, so it is not easily damaged, and even if the sheet is damaged due to an external impact, the film catches the glass fragments and prevents them from scattering, thereby preventing further damage.
이러한 이종 접합시트는 자동차의 전면 유리, 방범 성능을 요구하는 금융 시설, 유동 인구가 많으며 유리의 파손으로 피해를 줄이기 위해 고층 건물 외부 창유리, 발코니, 천창, 샤워 부스 등에 사용되고 있으며 유럽이나 미국, 호주, 중국 등의 나라에서 안전유리에 대한 사용 기준을 점차적으로 높여 이종 접합시트를 보다 많은 곳에 적용 확대하고 있다.These heterojunction sheets are used for windshields of automobiles, financial facilities that require crime prevention performance, and high-rise building exterior windows, balconies, skylights, and shower booths to reduce damage due to glass breakage with a large floating population. Countries such as China are gradually raising standards for safety glass and expanding the application of heterojunction sheets to more places.
일반적으로 이종 접합시트의 제조는 유리 사이의 중간 막으로 PVB(polyvinyl butyral) 필름 혹은 EVA(ethylene vinyl acetate) 필름을 넣고 예열 후 롤프레스(roll-press) 공정으로 필름과 유리를 밀착시킨 뒤 오토클레이브(autoclave)를 사용하여 장시간 동안 고온고압의 제조공정을 거친 후 공정에서 생기는 내부 기포를 제거하여 생산된다. 그러나 PVB 필름의 경우 건축용 접합 유리 소재의 대부분을 차지하지만 내수성이 떨어지기 때문에 백화현상과 유리층과의 박리 현상이 일어날 수 있다는 단점을 가지고 있다. EVA 필름은 가격이 저렴하고 내수성이 우수하지만 강도와 내광성이 떨어지는 단점이 있다. In general, in the manufacture of a heterojunction sheet, a polyvinyl butyral (PVB) film or an ethylene vinyl acetate (EVA) film is inserted as an intermediate film between glasses, and after preheating, the film and glass are brought into close contact with each other through a roll-press process, followed by autoclaving. It is produced by removing internal bubbles generated in the process after going through a manufacturing process of high temperature and high pressure for a long time using an autoclave. However, in the case of PVB film, although it occupies most of the laminated glass material for construction, it has a disadvantage that whitening and peeling from the glass layer may occur because of its low water resistance. EVA film is inexpensive and has excellent water resistance, but has poor strength and light resistance.
최근에는 이를 개선하기 위해 수지나 유리 사이를 광경화형 수지로 접착하는 이종 접합시트가 개발되고 있으며 광경화형 수지가 사용될 경우 최종 제품의 특성에 따라 이종 접합시트의 물성을 조절할 수 있으며 단시간 내 경화되는 특성으로 기존 필름접합공정 대비 제조기간을 단축할 수 있는 장점을 지니고 있다. 광경화형 수지는 열경화 수지에 비해 경화 시간이 매우 빠르기 때문에 공정 시간을 단축시킬 수 있고 저온에서 빠르게 경화되어 경화 과정에 들어가는 에너지 소모가 적으며 또한 수지 자체에 용제를 포함하고 있지 않아 공정 과정에서 휘발성 유기 화합물(VOCs)을 배출하지 않는 장점을 가지고 있어 최근 많은 산업분야에서 관심을 받고 있다.Recently, in order to improve this, a heterojunction sheet that bonds between resins or glass with a photocurable resin is being developed. When a photocurable resin is used, the physical properties of the heterojunction sheet can be adjusted according to the characteristics of the final product and cured in a short time. It has the advantage of shortening the manufacturing period compared to the existing film bonding process. Photocurable resins have a very fast curing time compared to thermosetting resins, so the process time can be shortened, and as they are rapidly cured at low temperatures, energy consumption for the curing process is reduced. Also, since the resin itself does not contain a solvent, it is volatile during the process. It has the advantage of not emitting organic compounds (VOCs) and has recently attracted attention in many industrial fields.
그러나 이 경우, 접합 과정에서 기포가 발생하기 쉽고, 이렇게 발생한 기포는 이종 접합시트의 투광성을 방해하여, 그 성능을 저하시키는 문제가 있었다. 또한, 일반적인 UV 경화형 수지는 장시간 동안 UV에 노출되는 경우, 색이 누렇게 변하는 황변현상을 일으키는데, 이러한 황변현상도 이종 접합시트의 투광성을 방해할 뿐만 아니라, 그 외관을 해치는 문제가 있었다.However, in this case, bubbles are easily generated during the bonding process, and the bubbles generated in this way hinder the light transmittance of the heterojunction sheet, thereby reducing its performance. In addition, when a general UV-curable resin is exposed to UV for a long time, it causes a yellowing phenomenon in which the color changes to yellow, and this yellowing phenomenon not only interferes with the light transmittance of the heterojunction sheet, but also has a problem of impairing its appearance.
개시된 발명은 기포 발생 억제 및 황변 현상 개선을 통해, 투명성이 개선되며 접착제 내부와 표면의 경화율을 높일 수 있는 UV 경화형 접착제를 제공하고자 한다.The disclosed invention is to provide a UV curable adhesive capable of improving transparency and increasing the curing rate of the inside and surface of the adhesive through suppression of blistering and improvement of yellowing.
또한 개시된 발명은 내구성이 향상되고 수축률과 기포 발생이 낮아지게 되며, 이로 인해 투명도, 헤이즈 등의 광학적 특성과 접착강도 및 충격강도를 향상시킬 수 있는 UV 경화형 접착제를 포함하는 이종 접합시트를 제공하고자 한다.In addition, the disclosed invention is to provide a heterojunction sheet containing a UV curable adhesive capable of improving durability, shrinkage rate and bubble generation, thereby improving optical properties such as transparency and haze, adhesive strength and impact strength. .
또한 상술한 바와 같은 기술적 과제들로 한정되지 않으며, 이하의 설명으로부터 또 다른 기술적 과제가 도출될 수도 있음은 자명하다.In addition, it is not limited to the technical problems as described above, and it is obvious that other technical problems may be derived from the following description.
개시된 내용은 우레탄 아크릴레이트 올리고머; 아크릴레이트 모노머; 광개시제; 및 첨가제를 포함하며, 상기 광개시제는 단파장 광개시제와 장파장 광개시제를 배합하여 사용하며, 상기 첨가제는 자외선 반응성 화합물, 적외선 차단 성분 및 자외선 흡수 성분으로 이루어진 군에서 선택된 어느 하나 이상인 UV 경화형 접착제를 일 실시예로 개시한다.Disclosed are urethane acrylate oligomers; acrylate monomer; photoinitiators; And an additive, wherein the photoinitiator is a combination of a short-wavelength photoinitiator and a long-wavelength photoinitiator, and the additive is a UV curable adhesive that is at least one selected from the group consisting of a UV-reactive compound, an infrared ray blocking component, and a UV absorbing component. Initiate.
개시된 내용의 특징에 따르면, 상기 UV 경화형 접착제 전체 100 중량부에 대하여, 상기 우레탄 아크릴레이트 올리고머 10 내지 50 중량부, 상기 아크릴레이트 모노머 50 내지 80 중량부 및 상기 광개시제 0.1 내지 5 중량부로 포함되는 것일 수 있다.According to the characteristics of the disclosure, based on the total 100 parts by weight of the UV curable adhesive, 10 to 50 parts by weight of the urethane acrylate oligomer, 50 to 80 parts by weight of the acrylate monomer, and 0.1 to 5 parts by weight of the photoinitiator It may be included there is.
또한, 상기 우레탄 아크릴레이트 올리고머의 평균 분자량은 1000 내지 3000g/mol 일 수 있다.In addition, the average molecular weight of the urethane acrylate oligomer may be 1000 to 3000 g / mol.
또한, 상기 자외선 반응성 유무기입자는 하기의 구조식(1)인 것일 수 있다.In addition, the UV-reactive organic-inorganic particles may have the following Structural Formula (1).
(상기의 [구조식 1]에서 실리카입자는 와 같은 망상구조를 나타내며, 상기 R은 C2 ~ C20의 지방족 또는 지환족 알킬기, 방향족 구조의 화합물을 나타내며, Acryl은 아크릴 화합물이다. )(In [Structural Formula 1] above, the silica particles are Represents a network structure such as, wherein R represents a C2 ~ C20 aliphatic or alicyclic alkyl group, an aromatic compound, and Acryl is an acrylic compound. )
또한 개시된 내용은 상기 UV 경화형 접착제를 포함하는 접착층; 및 상기 접착층의 양면에 형성되는 기재층을 포함하는 UV 경화형 접착제를 포함하는 이종 접합시트를 또다른 일 실시예로 개시한다.Also disclosed is an adhesive layer comprising the UV curable adhesive; And a heterojunction sheet comprising a UV curable adhesive including a substrate layer formed on both sides of the adhesive layer is disclosed as another embodiment.
개시된 내용의 특징에 따르면, 상기 기재층은 폴리메틸메타아크릴레이트, 폴리카보네이트, 아크릴로니트릴부타디엔스티렌 공중합체 또는 강화유리로 이루어진 그룹에서 선택되는 어느 하나인 것을 특징으로 한다.According to the characteristics of the disclosed contents, the base layer is characterized in that any one selected from the group consisting of polymethyl methacrylate, polycarbonate, acrylonitrile butadiene styrene copolymer or tempered glass.
또한 상기 기재층은 2층 내지 4층으로 형성되며, 복수의 상기 기재층 사이에는 상기의 접착층이 각각 형성되는 것을 특징으로 할 수 있다.In addition, the base layer may be formed of two to four layers, and the adhesive layer may be formed between the plurality of base layers, respectively.
또한 상기 UV 경화형 접착제를 포함하는 이종 접합시트는 방범이나 방탄시트 용도로 사용되는 것을 특징으로 할 수 있다.In addition, the heterojunction sheet containing the UV curable adhesive may be characterized in that it is used for crime prevention or bulletproof sheet purposes.
개시된 내용의 일 실시예에 따른 UV 경화형 접착제에 의하면, 기포 발생 억제 및 황변 현상 개선을 통해, 투명성이 개선된다는 장점이 있다. According to the UV curable adhesive according to an embodiment of the disclosed subject matter, there is an advantage in that transparency is improved through suppression of bubble generation and improvement of yellowing phenomenon.
또한 개시된 내용의 일 실시예에 따른 UV 경화형 접착제를 포함하는 이종 접합시트에 의하면, 내구성이 향상되고 수축률과 기포 발생이 낮아지게 되며, 이로 인해 투명도, 헤이즈 등의 광학적 특성과 접착강도 및 충격강도를 향상시킬 수 있다는 장점이 있다.In addition, according to the heterojunction sheet containing a UV curable adhesive according to an embodiment of the present disclosure, durability is improved and shrinkage rate and bubble generation are lowered, thereby improving optical properties such as transparency and haze, adhesive strength, and impact strength. It has the potential to improve.
본 발명의 효과들은 이상에서 언급한 효과들로 제한되지 않으며, 언급되지 않은 또 다른 효과들은 청구범위의 기재로부터 당업자에게 명확하게 이해될 수 있을 것이다.The effects of the present invention are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description of the claims.
1. UV 경화형 접착제1. UV curable adhesive
본 명세서에 개시된 UV 경화형 접착제는 우레탄 아크릴레이트 올리고머; 아크릴레이트 모노머; 광개시제; 및 첨가제를 포함하며, 상기 광개시제는 단파장 광개시제와 장파장 광개시제를 배합하여 사용하며, 상기 첨가제는 자외선 반응성 화합물, 적외선 차단 성분 및 자외선 흡수 성분으로 이루어진 군에서 선택된 어느 하나 이상인 UV 경화형 접착제에 해당한다. 상기 UV 경화형 접착제는 기포 발생 억제 및 황변 현상 개선을 통해, 투명성이 개선되며 접착제 내부와 표면의 경화율을 높일 수 있다는 특징을 가진다. 이하, 상기 UV 경화형 접착제에 포함되는 구성을 보다 상세하게 설명한다.UV curable adhesives disclosed herein include urethane acrylate oligomers; acrylate monomer; photoinitiators; And an additive, wherein the photoinitiator is a combination of a short-wavelength photoinitiator and a long-wavelength photoinitiator, and the additive is at least one selected from the group consisting of a UV-reactive compound, an infrared blocking component, and a UV-absorbing component. Corresponds to a UV curable adhesive. The UV-curable adhesive has the characteristics of improving transparency and increasing the curing rate of the inside and surface of the adhesive by inhibiting blistering and improving yellowing. Hereinafter, configurations included in the UV curable adhesive will be described in more detail.
(1) 우레탄 아크릴레이트 올리고머(1) Urethane Acrylate Oligomer
아크릴레이트 올리고머의 종류 중 우레탄 아크릴레이트 올리고머는 경화성, 내마모성 및 유연성 등이 우수한 아크릴레이트에 해당하여 UV 경화형 접착제에 사용하기에 적합한 올리고머에 해당한다.Among the types of acrylate oligomers, urethane acrylate oligomers correspond to acrylates having excellent curability, abrasion resistance and flexibility, and thus correspond to oligomers suitable for use in UV curable adhesives.
상기 우레탄 아크릴레이트 올리고머의 평균 분자량은 특별히 제한되는 것은 아니나, 1,000 내지 3,000g/mol인 것이 바람직하다. 평균 분자량이 1,000g/mol 미만인 경우에는 접합에 의한 경도 향상효과가 낮아지는 문제가 발생할 수 있으며, 평균 분자량이 3,000g/mol을 초과하는 경우에는 지나치게 높은 점도에 의해 작업성 저하가 발생할 수 있다. The average molecular weight of the urethane acrylate oligomer is not particularly limited, but is preferably 1,000 to 3,000 g/mol. When the average molecular weight is less than 1,000 g / mol, a problem of lowering the hardness improvement effect by bonding may occur, and when the average molecular weight exceeds 3,000 g / mol, workability may be deteriorated due to excessively high viscosity.
상기 우레탄 아크릴레이트 올리고머는 이소시아네이트, 폴리올을 중합하여 합성한 폴리우레탄과 아크릴 단량체를 중합하여 생성할 수 있으나, 이에 제한되는 것은 아니다. The urethane acrylate oligomer may be produced by polymerizing polyurethane and acrylic monomers synthesized by polymerizing isocyanate and polyol, but is not limited thereto.
상기 이소시아네이트는 지방족 이소시아네이트, 방향족 이소시아네이트 등 그 종류에 제한이 없이 사용 가능하다. 상기 지방족 이소시아네이트로는 이소포론디이소시아네이트(Isophoronediisocyanate;IPDI) 1,6-헥사메틸렌 디이소시아네이트(1,6-hexamethylenediisocyanate;HDI), 4,4-디시클로헥실메탄 디이소시아네이트 (4,4-dicyclohexylmethanediisocyanate;H12MDI), 3-이소시아네이토메틸-3,5,5- 트리시클로헥실 이소시아네이트 (3-isocyanatomethyl- 3,5,5-trimethylcyclohexylisocyanate ; IPDI), 1,4-시클로헥실 디이소시아네이트 (1,4-cyclohexyl diisocyanate;CHDI) 및 2,2,4-트리메틸헥사메틸렌 디이소시아네이트 (2,2,4-trimethylhexamethylene diisocyanate ; TMDI) 등을 사용할 수 있으며, 상기 방향족 이소시아네이트로는 톨릴렌 디이소시아네이트, 크실릴렌 디이소시아네이트, 메틸렌디페닐 디이소시아네이트, 페닐렌 디이소시아네이트 및 나프탈렌 디이소시아네이트 등을 사용할 수 있다.The isocyanate can be used without limitation in its kind, such as aliphatic isocyanate and aromatic isocyanate. The aliphatic isocyanates include isophorone diisocyanate (IPDI), 1,6-hexamethylene diisocyanate (HDI), 4,4-dicyclohexylmethane diisocyanate (4,4-dicyclohexylmethanediisocyanate; H12MDI ), 3-isocyanatomethyl-3,5,5-tricyclohexyl isocyanate (IPDI), 1,4-cyclohexyl diisocyanate (1,4-cyclohexyl diisocyanate; CHDI) and 2,2,4-trimethylhexamethylene diisocyanate (2,2,4-trimethylhexamethylene diisocyanate; TMDI) may be used. As the aromatic isocyanate, tolylene diisocyanate, xylylene diisocyanate, Methylenediphenyl diisocyanate, phenylene diisocyanate, naphthalene diisocyanate and the like can be used.
상기 폴리올은 본 발명의 기술분야에서 일반적으로 사용되는 것이라면 그 종류가 특별히 제한되지는 않으나, 폴리올은 단분자 디올류를 보다 바람직하게 사용할 수 있다. 예를 들면, 에틸렌글리콜, 프로필렌글리콜, 1,3-부탄디올, 1,4-부탄디올, 1,5-펜탄디올, 1,6-헥산디올, 네오펜틸글리콜, 1,4-사이클로헥산 디메타놀, 비스페놀A, 비스페놀F, 환원비스페놀A, 환원비스페놀F, 디사이클로펜타 디올, 트리사이클로데칸디올 및 이들의 혼합물로 이루어진 군에서 선택되는 1종 이상의 단분자 디올류의 폴리올을 사용할 수 있다. 또한, 이러한 단분자 디올류의 폴리올은 폴리에스테르글리콜, 폴리에테르글리콜, 폴리카보네이트글리콜, 폴리에틸렌글리콜, 폴리프로필렌글리콜, 아민 말단화된 폴리에테르, 폴리트리메틸렌 에테르글리콜, 폴리트리메틸렌 에테르에스테르 글리콜, 폴리트리메틸렌-co-에틸렌 에테르글리콜, 폴리테트라메틸렌 에테르글리콜 및 이들의 혼합물로 이루어진 군에서 선택되는 1종 이상의 폴리올과 함께 혼합하여 사용될 수 있다.The type of the polyol is not particularly limited as long as it is generally used in the technical field of the present invention, but monomolecular diols may be more preferably used as the polyol. For example, ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexane dimethanol, bisphenol A, bisphenol F, reduced bisphenol A, reduced bisphenol F, dicyclopentadiol, tricyclodecanediol, and one or more monomolecular diols selected from the group consisting of mixtures thereof may be used. In addition, polyols of these monomolecular diols include polyester glycol, polyether glycol, polycarbonate glycol, polyethylene glycol, polypropylene glycol, amine-terminated polyether, polytrimethylene ether glycol, polytrimethylene ether ester glycol, poly It may be used in combination with at least one polyol selected from the group consisting of trimethylene-co-ethylene ether glycol, polytetramethylene ether glycol, and mixtures thereof.
상기 아크릴 단량체는 그 종류에 제한이 없으나, 구체적으로는 2-히드록시에틸 메타크릴레이트(2-Hydroxyethyl methacrylate, HEMA), 2-(2-히드록시에톡시)에틸 메타크릴레이트(2-(2-hydroxyethoxy)ethyl methacrylate), 도데실 메타크릴레이트(Dodecyl methacrylate), 2-에틸헥실 아크릴레이트(2-Ethylhexyl acrylate, 2-EHA), 테트라데실 메타크릴레이트(Tetradecyl methacrylate), 히드록시에틸 아크릴레이트(Hydroxyethyl acrylate, HEA), 글리시딜 메타크릴레이트(Glycidyl methacrylate, GMA), 이소보르네올 아크릴레이트(Isoborneol acrylate, IBOA), 아크릴산(Acrylic acid, AA), 메틸 메타크릴레이트(Methyl methacrylate, MMA), 사이클로헥실 메타크릴레이트(Cyclohexyl methacrylate, CHMA) 로 이루어진 군에서 선택되는 하나 이상을 사용할 수 있다.The acrylic monomer is not limited in its kind, but specifically, 2-hydroxyethyl methacrylate (HEMA), 2- (2-hydroxyethoxy) ethyl methacrylate (2- (2 -hydroxyethoxyethyl methacrylate), Dodecyl methacrylate, 2-Ethylhexyl acrylate, 2-EHA, Tetradecyl methacrylate, Hydroxyethyl acrylate ( Hydroxyethyl acrylate (HEA), Glycidyl methacrylate (GMA), Isoborneol acrylate (IBOA), Acrylic acid (AA), Methyl methacrylate (MMA), At least one selected from the group consisting of cyclohexyl methacrylate (CHMA) may be used.
상기 우레탄 아크릴레이트 올리고머는 UV 경화형 접착제 전체 100 중량부에 대하여 10 내지 50 중량부로 포함되는 것이 바람직하다. 10 중량부 미만으로 포함되는 경우에는 점도가 낮아서 코팅두께 조절이 어려우며, 50 중량부를 초과하여 포함되는 경우에는 점도가 너무 높아지고 초기 접착력이 낮아지는 단점이 있다.The urethane acrylate oligomer is preferably included in an amount of 10 to 50 parts by weight based on 100 parts by weight of the total UV curable adhesive. When included in less than 10 parts by weight, it is difficult to control the coating thickness due to low viscosity, and when included in more than 50 parts by weight, the viscosity is too high and the initial adhesive strength is low.
(2) 아크릴레이트 모노머(2) Acrylate monomer
아크릴레이트 모노머는 유리 또는 폴리카보네이트 시트와의 접착력을 높이기 위해 추가되거나, 올리고머를 저점도화하여 작업성을 향상시키는 목적을 가지는 반응성 희석제로써 추가되는 조성물이다. 또한 가교에 의해 UV 경화형 접착제 조성물의 일부가 되기도 하는 물질이다. The acrylate monomer is a composition added as a reactive diluent for the purpose of improving workability by reducing the viscosity of an oligomer or increasing adhesion to a glass or polycarbonate sheet. It is also a material that also becomes part of the UV curable adhesive composition by crosslinking.
치환기의 종류에 따라 알킬 아크릴레이트 모노머, 하이드록시기를 함유한 아크릴레이트 모노머, 글리시딜기를 함유한 아크릴레이트 모노머 또는 질소성분을 함유한 아크릴레이트 모노머를 선택할 수 있다. 알킬 아크릴레이트 모노머로는 그 종류에 제한은 없으나 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 부틸아크릴레이트, 헥실(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 라우릴아크릴레이트, 이소데실아크릴레이트 등이 있으며, 하이드록시기를 함유한 아크릴레이트 모노머로는 그 종류에 제한은 없으나 하이드록시(메타)아크릴레이트, 하이드록시(메타)메틸아크릴레이트, 테트라하이드로푸르푸릴 아크릴레이트 , 하이드록시에틸 아크릴레이트, 하이드록시에틸 메타아크릴레이트, 하이드록시프로필 아크릴레이트, 하이드록시부틸 아크릴레이트, 2-하이드록시-3-페녹시프로필 아크릴레이트 등이 있으며, 글리시딜기를 함유한 아크릴레이트 모노머로는 그 종류에 제한은 없으나 글리시딜(메타)아크릴레이트 등이 있으며, 질소성분을 함유한 아크릴레이트 모노머로는 그 종류에 제한은 없으나 아크릴 아미드 또는 아크릴로니트릴 등이 있다. Depending on the type of substituent, an alkyl acrylate monomer, a hydroxy group-containing acrylate monomer, a glycidyl group-containing acrylate monomer, or a nitrogen-containing acrylate monomer may be selected. The type of alkyl acrylate monomer is not limited, but methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth ) Acrylate, lauryl acrylate, isodecyl acrylate, etc., and the type of acrylate monomer containing a hydroxyl group is not limited, but hydroxy (meth) acrylate, hydroxy (meth) methyl acrylate, Tetrahydrofurfuryl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, etc. Acrylate monomers containing a dil group include, but are not limited to, glycidyl (meth)acrylate, etc., and acrylate monomers containing a nitrogen component include, but are not limited to, acrylamide or acrylonitrile, etc. there is
또한 단관능성 아크릴레이트 모노머는 유연성이 높고 황변현상을 억제하여 투명성을 개선할 수 있으며, 다관능성 아크릴레이트 모노머는 가교밀도의 증진으로 인하여 높은 탄성율을 나타내므로, 목적에 맞는 아크릴레이트 모노머를 적절히 선택할 수 있다. 단관능성 아크릴레이트 모노머로는 그 종류에 제한이 없으나 2-에틸헥실(메타)아크릴레이트, N,N-디메틸(메타)아크릴레이트, N-비닐카프로락탐, N-비닐피롤리돈, t-부틸(메타)아크릴레이트, t-옥틸(메타)아크릴레이트, 노닐(메타)아크릴레이트, 도데실(메타)아크릴레이트, 디메틸아미노에틸(메타)아크릴레이트, 디사이클로펜타닐(메타)아크릴레이트, 디사이클로펜타디엔(메타)아크릴레이트, 디아세톤(메타)아크릴아마이드, 디에틸아미노에틸(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 메톡시에틸렌글리콜(메타)아크릴레이트, 메톡시폴리에틸렌글리콜(메타)아크릴In addition, monofunctional acrylate monomers have high flexibility and can suppress yellowing to improve transparency, and multifunctional acrylate monomers exhibit high modulus of elasticity due to enhancement of crosslinking density, so it is possible to appropriately select an acrylate monomer suitable for the purpose. there is. The monofunctional acrylate monomer is not limited in its kind, but 2-ethylhexyl (meth)acrylate, N,N-dimethyl (meth)acrylate, N-vinylcaprolactam, N-vinylpyrrolidone, t-butyl (meth)acrylate, t-octyl (meth)acrylate, nonyl (meth)acrylate, dodecyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclo Pentadiene (meth) acrylate, diacetone (meth) acrylamide, diethylaminoethyl (meth) acrylate, lauryl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) )acryl
레이트, 메톡시폴리프로필렌글리콜(메타)아크릴레이트, 메틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 보닐(메타)아크릴레이트, 부톡시에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 사이크로헥실(메타)아크릴레이트, 스티어릴(메타)아크릴레이트, 에톡시에톡시에틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 에폭시디에틸렌글리콜(메타)아크릴레이트, 옥타데실(메타)아크릴레이트, 이소데실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 이소부톡시(메타)아크릴아마이드, 이소부틸(메타)아크릴레이트, 이소아밀(메타)아크릴레이트, 이소프로필(메타)아크릴레이트, 테트라하이드로퍼퓨릴(메타)아크릴레이트, 트리사이클로데카닐(메타)아크릴레이트, 페녹시에틸(메타)아크릴레이트, 폴리에틸렌글리콜모노(메타)아크릴레이트, 폴리프로필렌글리콜모노(메타)아크릴레이트, 프로필(메타)아크릴레이트, 하이드록시 에틸(메타)아크릴레이트로 이루어진 그룹에서 선택되는 어느 하나 이상이 바람직하고, 다관능성 모노머는 그 종류에 제한이 없으나 1,6-헥산디올디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 트리메틸올프로판트리옥시에틸(메타)아크릴레이트, 트리사이크로데칸디메탄올디아크릴레이트, 트리프로필렌글리콜디아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트로 이루어진 그룹에서 선택되는 어느 하나 이상이 바람직하다.rate, methoxypolypropylene glycol (meth)acrylate, methyl (meth)acrylate, benzyl (meth)acrylate, bornyl (meth)acrylate, butoxyethyl (meth)acrylate, butyl (meth)acrylate, Cyclohexyl (meth)acrylate, steeryl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, ethyl (meth)acrylate, epoxydiethylene glycol (meth)acrylate, octadecyl (meth)acrylate Acrylate, isodecyl (meth)acrylate, isobornyl (meth)acrylate, isobutoxy (meth)acrylamide, isobutyl (meth)acrylate, isoamyl (meth)acrylate, isopropyl (meth)acrylate , tetrahydrofurfuryl (meth)acrylate, tricyclodecanyl (meth)acrylate, phenoxyethyl (meth)acrylate, polyethylene glycol mono (meth)acrylate, polypropylene glycol mono (meth)acrylate, propyl At least one selected from the group consisting of (meth)acrylate and hydroxyethyl (meth)acrylate is preferred, and the multifunctional monomer is not limited in its kind, but 1,6-hexanediol di(meth)acrylate, Ethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane trioxyethyl(meth)acrylate, tricyclodecane dimethanol diacrylate, tripropylene glycol diacrylate, pentaeryth Any one or more selected from the group consisting of ritol tri (meth) acrylate is preferred.
상기 아크릴레이트 모노머는 UV 경화형 접착제 전체 100 중량부에 대하여 50 내지 80 중량부로 포함되는 것이 바람직하다. 50 중량부 미만으로 포함되는 경우에는 흐름성 저하로 인해서 접착제의 도포 및 코팅이 어려워지고, 80 중량부를 초과하여 포함되는 경우에는 점착제의 점도가 낮아서 코팅두께가 불균일해지고 경화시간이 길어지는 문제점이 발생된다.The acrylate monomer is preferably included in an amount of 50 to 80 parts by weight based on 100 parts by weight of the total UV curable adhesive. If it is included in less than 50 parts by weight, it becomes difficult to apply and coat the adhesive due to reduced flowability, and if it is included in more than 80 parts by weight, the viscosity of the adhesive is low, resulting in uneven coating thickness and long curing time. do.
(3) 광개시제(3) Photoinitiator
광개시제란 UV 경화형 접착제에 첨가되어 UV 램프로부터 에너지를 흡수하여 중합 반응을 시작하게 하는 물질을 의미한다. A photoinitiator means a material added to a UV curable adhesive to absorb energy from a UV lamp to start a polymerization reaction.
상기 광개시제는 광조사에 의해 라디칼을 발생시켜 중합 반응을 개시시킬 수 있는 것이라면 크게 제한되지 않고 사용될 수 있다. 바람직하게는 벤조인계, 하이드록시케톤계, 아미노케톤계 및 포스핀옥사이드계 화합물 중에서 선택되는 어느 하나 이상을 사용할 수 있으며, 반드시 이에 제한되는 것은 아니다. 구체적으로는 2,2-디메톡시-2-페닐-아세토페논, 잔톤, 1-히드록시사이클로헥실페닐As the photoinitiator, any photoinitiator capable of initiating a polymerization reaction by generating radicals by light irradiation may be used without any particular limitation. Preferably, any one or more selected from benzoin-based, hydroxyketone-based, amino-ketone-based, and phosphine oxide-based compounds may be used, but is not necessarily limited thereto. Specifically, 2,2-dimethoxy-2-phenyl-acetophenone, xanthone, 1-hydroxycyclohexylphenyl
케톤, 벤즈알데하이드, 안트라퀴논, 3-메틸아세토페논, 1-(4-이소프로필-페놀)-2-히드록시-2-메틸 프로판-1-온, 티오잔톤, 4-클로로벤조페논, 4,4'-디메톡시벤조페논, 4,4'-디아미노벤조페논, 벤조인 프로필 에테르, 벤조인에틸에테르 및 이들의 혼합물로 이루어진 군에서 선택되는 1 종 이상을 사용할 수 있으며, 상업용 광개시제로는 Ciba Geigy사(Klybecstrasse 141, Basle, Baslestadt, 4002, Switzerland)의 Irgacure 127, 184, 250, 369, 379, 651, 500, 754, 784, 819, 819DW, 907, 1300, 1700, 1800, 2022, 2100, 2959 등이 있다. 이들 중 하나를 단독으로 사용할 수도 있으나 둘 이상을 혼합하여 사용할 수 있다.Ketone, benzaldehyde, anthraquinone, 3-methylacetophenone, 1-(4-isopropyl-phenol)-2-hydroxy-2-methyl propan-1-one, thioxanthone, 4-chlorobenzophenone, 4, At least one selected from the group consisting of 4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, benzoin propyl ether, benzoin ethyl ether, and mixtures thereof may be used, and commercial photoinitiators include Ciba Irgacure 127, 184, 250, 369, 379, 651, 500, 754, 784, 819, 819DW, 907, 1300, 1700, 1800, 20 from Geigy (Klybecstrasse 141, Basle, Baslestadt, 4002, Switzerland) 22, 2100; 2959, etc. One of these may be used alone, but two or more may be mixed and used.
UV 광 파장에 따른 흡수율에 따라 단파장 흡수 광개시제(표면 경화용)와 장파장 흡수 광개시제(심부 경화용)로 각각 사용하는 것도 가능하나, 파장대가 다양한 광개시제를 복합적으로 사용하는 경우에는 UV 경화 시에 접착제의 내부와 표면의 경화율을 높일 수 있으므로, 양 광개시제를 배합하여 사용하는 것이 바람직하다. 표면 경화용 광개시제는 IC-184(1-Hydroxy-cyclohexyl phenyl ketone), DC-1173(2-Hydroxy-2-methyl-1-phenyl-1-propanone) 및 IC-2959 등이 있고, 심부 경화용 광개시제는 DC-TPO(Diphenyl(2,46-trimethylbenzoyl)-phosphine oxide), IC- 819(phosphine oxide, pheny bis(2,4,6-trimethyl benzoyl)), IC2100(phosphine oxide) 및 IC-2022(IC-819+DC1173) 등을 사용하는 것이 가능하다. Depending on the absorption rate according to the UV light wavelength, it is possible to use a short wavelength absorption photoinitiator (for surface curing) and a long wavelength absorption photoinitiator (for deep curing), respectively. Since the curing rate of the inside and the surface can be increased, it is preferable to use both photoinitiators in combination. Photoinitiators for surface curing include IC-184 (1-Hydroxy-cyclohexyl phenyl ketone), DC-1173 (2-Hydroxy-2-methyl-1-phenyl-1-propanone) and IC-2959, and photoinitiators for deep curing DC-TPO (Diphenyl(2,46-trimethylbenzoyl)-phosphine oxide), IC-819 (phosphine oxide, pheny bis(2,4,6-trimethyl benzoyl)), IC2100 (phosphine oxide) and IC-2022 (IC -819+DC1173) and so on.
상기 광개시제는 UV 경화형 접착제 전체 100 중량부에 대하여 0.1 내지 5 중량부로 포함되는 것이 바람직하다. 0.1 중량부 미만으로 포함되는 경우에는 중합 속도가 느리고 전환률이 낮으며, 5 중량부를 초과하여 포함되는 경우에는 반응속도는 빠르지만 저분자량의 올리고머가 많이 존재하여 점착제의 물성이 저하된다.The photoinitiator is preferably included in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the total UV curable adhesive. When it is included in less than 0.1 parts by weight, the polymerization rate is slow and the conversion rate is low, and when it is included in more than 5 parts by weight, the reaction rate is fast, but there are many low molecular weight oligomers, and the physical properties of the adhesive are deteriorated.
(4) 첨가제 (4) Additives
본 발명에 의한 UV 경화형 접착제에는 추가적인 목적 부여를 위해 달성하고자 하는 효과가 저하되지 않는 범위 내에서 첨가제를 더 포함할 수 있다. The UV curable adhesive according to the present invention may further include an additive within a range in which the effect to be achieved is not deteriorated in order to provide an additional purpose.
본 발명에 의한 UV 경화형 접착제 상기 자외선 반응성 유무기 화합물은 아래 [구조식 1]로 표시되는 화합물이며, 나노크기의 실리카 입자에 자외선 경화가 가능하도록 아크릴기가 결합되어 있는 화합물이다. The UV-curable adhesive according to the present invention is a compound represented by [Structural Formula 1] below, and is a compound in which an acrylic group is bonded to nano-sized silica particles to enable UV curing.
[구조식 1] [Structural Formula 1]
상기의 [구조식 1]에서 실리카입자는 와 같은 망상구조를 나타내며, 상기 R은 합성에 사용되는 화합물의 구조에 따라 달라질 수 있으나, 바람직하게는 C2 ~ C20의 지방족 또는 지환족 알킬기, 방향족 구조의 화합물을 나타내며, Acryl은 아크릴 화합물을 나타낸다. In [Structural Formula 1] above, the silica particles are Represents a network structure such as, The R may vary depending on the structure of the compound used in the synthesis, but preferably represents a C2 ~ C20 aliphatic or alicyclic alkyl group, an aromatic compound, and Acryl represents an acrylic compound.
나노 크기의 상기 자외선 반응성 유무기 화합물을 도입하며 자외선 조사 시, 반응성 무기입자가 우레탄 아크릴레이트 올리고머 및 아크릴레이트 모노머와 함께 경화되어, 경화된 폴리머 접착층 구조 내에 일정하게 분포하게 됨에 따라, 구조적 특징으로 내구성이 향상되고 수축률과 기포 발생이 낮아지게 되며, 이로 인해 투명The nano-sized UV-reactive organic/inorganic compound is introduced, and upon UV irradiation, the reactive inorganic particles are cured together with the urethane acrylate oligomer and the acrylate monomer, and are uniformly distributed in the cured polymer adhesive layer structure, resulting in durability as a structural feature. is improved and shrinkage and blistering are lowered, resulting in transparent
도, 헤이즈 등의 광학적 특성과 접착강도 및 충격강도를 향상시킬 수 있는 효과가 있다. It has an effect of improving optical properties such as degree, haze, adhesive strength, and impact strength.
본 발명에 의한 UV 경화형 접착제에는 이를 포함하여 접착되는 이종 접합시트에 적외선 차단 기능을 부여하기 위하여 적외선 차단 물질을 더 포함할 수 있다. 상기 적외선 차단 물질로는 통상의 적외선 차단을 위한 물질인 경우 제한없이 이용이 가능하며, 구체적으로는 티타늄, 아연, 인듐, 주석, 안티몬, 몰리브덴, 탄탈륨, 텅스텐, 바나듐 및 니오븀 등에서 선택되는 단일 금속을 포함하는 금속 산화물 또는 복수의 금속을 포함하는 금속 복합산화물일 수 있다.The UV curable adhesive according to the present invention may further include an infrared ray blocking material in order to impart an infrared ray blocking function to the heterojunction sheet bonded thereto. As the infrared blocking material, any material for blocking infrared rays can be used without limitation, and specifically, a single metal selected from titanium, zinc, indium, tin, antimony, molybdenum, tantalum, tungsten, vanadium, niobium, etc. It may be a metal oxide containing or a metal composite oxide containing a plurality of metals.
본 발명에 의한 UV 경화형 접착제에는 이를 포함하여 접착되는 이종 접합시트에 자외선 차단 기능을 부여하기 위하여 자외선 흡수 물질을 더 포함할 수 있다. 상기 자외선 흡수 물질로는 2-(3-tert-부틸-2-히드록시-5-메틸페닐)-5-클로로벤조티리아졸, 알콕시벤조페논 등을 사용할 수 있다. The UV curable adhesive according to the present invention may further include an ultraviolet ray absorbing material in order to impart an ultraviolet ray blocking function to the heterojunction sheet bonded thereto. As the UV absorbing material, 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotyriazole, alkoxybenzophenone, and the like may be used.
오일겔화제는 UV 경화형 접착제 조성물의 점도를 조절할 수 있으며 곡면이 있는 기재층에도 도포하기 쉽다는 효과가 있다. 상기 오일겔화제로는 하이드록시지방산, 하이드록시지방산 아미드 등의 지방족 아미드를 사용하는 것이 투명성 측면에서 바람직하다. The oil gelling agent can adjust the viscosity of the UV curable adhesive composition and has an effect of being easy to apply even to a substrate layer having a curved surface. As the oil gelling agent, it is preferable to use an aliphatic amide such as hydroxy fatty acid or hydroxy fatty acid amide in terms of transparency.
열중합 금지제 열에 의한 라디칼의 생성으로 보관 중에 반응이 진행되어 겔화되는 것을 방지하기 위한 것으로, 메톡시에틸하이드록시퀴논, 하이드로퀴논 등을 사용할 수 있으나, 당업자가 이용할 수 있는 것이라면 그 종류에 제한이 없다.Thermal polymerization inhibitor This is to prevent gelation due to the reaction proceeding during storage due to the generation of radicals by heat. does not exist.
습윤제는 피착면에 표면 장력이 낮을 때 접착제의 표면 장력을 저하시켜 퍼짐성을 향상시키기 위해 첨가되는 물질로, 당업자가 이용할 수 있는 것이라면 그 종류에 제한이 없다.A wetting agent is a material added to improve the spreadability by reducing the surface tension of the adhesive when the surface tension is low on the adhered surface, and there is no limitation in the type as long as it can be used by those skilled in the art.
소포제는 접착제를 도포하는 과정 중 발생할 수 있는 와류에 의해 발생되는 기포의 제거를 위해 첨가되는 것으로, 변성 실리콘 아크릴레이트 등을 사용할 수 있으나 당업자가 이용할 수 있는 것이라면 그 종류에 제한이 없다.The antifoaming agent is added to remove air bubbles generated by vortexes that may occur during the process of applying the adhesive, and modified silicone acrylate or the like may be used, but the type is not limited as long as it is available to those skilled in the art.
가소제는 점착제 조성물의 소성 가공성을 향상시키고, UV 경화형 접착제 조성물에 의하여 형성되는 접착층에 유연성을 부여한다. 가소제로, 프탈레이트계 가소제, 트리멜리트산 에스테르계 가소제, 인산 에스테르계 가소제, 에폭시계 가소제, 폴리에스터계 가소제, 지방족 에스트레스계 가소제, 염소화 파라핀계 가소제 등이 있으며, 이에 제한되는 것은 아니다.The plasticizer improves the plastic processability of the pressure-sensitive adhesive composition and imparts flexibility to the adhesive layer formed by the UV curable adhesive composition. Plasticizers include, but are not limited to, phthalate-based plasticizers, trimellitic acid ester-based plasticizers, phosphate-based plasticizers, epoxy-based plasticizers, polyester-based plasticizers, aliphatic stress-based plasticizers, and chlorinated paraffinic plasticizers.
산화 방지제로는 (Tris(2,4-di-tert-butylphenyl) phosphite, Irgafos 168) 등을 이용할 수 있으나 이에 제한되는 것은 아니다.As an antioxidant, (Tris(2,4-di-tert-butylphenyl) phosphite, Irgafos 168) may be used, but is not limited thereto.
추가적으로 ε-카프로락톤(ε-caprolactone)을 첨가할 수 있으며, 이는 제조, 혼합, 배합이 쉬워 수지 첨가제로서 일반적으로 사용되고 있는 것으로, 가공 특성과 내구성, 유연성, 압축영구변형, 인열강도 등의 특성을 강화할 수 있다. Additionally, ε-caprolactone can be added, which is commonly used as a resin additive because it is easy to manufacture, mix, and mix, and has properties such as processing characteristics, durability, flexibility, compression set, and tear strength can strengthen
그 외에도 첨가제로 충진제, 충격보강제, 고분자 화합물, 분산제, 밀착 촉진제, 대전방지제, 난연제, 활제, 난연제, 활제, 충격보강제로 이루어지는 군에서 선택되는 하나 이상의 첨가제를 포함할 수 있으나 이에 한정되는 것은 아니다. In addition, additives may include one or more additives selected from the group consisting of fillers, impact modifiers, polymer compounds, dispersants, adhesion promoters, antistatic agents, flame retardants, lubricants, flame retardants, lubricants, and impact modifiers, but are not limited thereto.
상기 첨가제의 함량은 부여하고자 하는 기능과 목적에 따라 상이할 수 있다.The content of the additive may vary depending on the function and purpose to be imparted.
2. UV 경화형 접착제를 포함하는 이종 접합시트2. Heterogeneous bonding sheet containing UV curable adhesive
본 명세서에 개시된 UV 경화형 접착제를 포함하는 이종 접합시트는 상기에서 상세하게 설명한 UV 경화형 접착제를 포함하는 접착층; 및 상기 접착층의 양면에 형성되는 기재층을 포함하는 UV 경화형 접착제를 포함한다. 상기 UV 경화형 접착제를 포함하는 이종 접합시트(이하, 이종 접합시트)는 내구성이 향상되고 수축률과 기포 발생이 낮아지게 되며, 이로 인해 투명도, 헤이즈 등의 광학적 특성과 접착강도 및 충격강도를 향상시킬 수 있다는 특징이 있다.A heterojunction sheet comprising a UV curable adhesive disclosed herein includes an adhesive layer comprising the UV curable adhesive described in detail above; And a UV curable adhesive comprising a base layer formed on both sides of the adhesive layer. The heterojunction sheet (hereinafter referred to as heterojunction sheet) containing the UV-curable adhesive has improved durability, reduced shrinkage and reduced bubble generation, and thereby improved optical properties such as transparency and haze, as well as adhesive strength and impact strength. There is a feature that
상기 이종 접합시트의 용도에는 제한이 없으나, 방범이나 방탄시트 용도로 사용되는 것이 바람직하다. 이하에서는 상기 이종 접합시트의 구성에 대해 보다 상세하게 설명한다. There is no limitation on the use of the heterojunction sheet, but it is preferably used for crime prevention or bulletproof sheets. Hereinafter, the configuration of the heterojunction sheet will be described in more detail.
(1) 접착층(1) adhesive layer
접착층은 기재층 사이를 접착하는 역할을 하는 층으로, 0.5 내지 6 밀리미터의 두께로 형성된다. 또한 상기에서 설명한 UV 경화형 접착제 조성물을 포함하므로 기포 발생 억제 및 황변 현상 개선을 통해, 투명성이 개선되며 접착제 내부와 표면의 경화율이 높다. 액상 형태의 UV 경화형 접착제를 기재층 사이에 주입하고 UV 경화기로 경화하면 고체 형태로 경화되어 기재층을 접착시키는 역할을 한다.The adhesive layer serves to adhere between substrate layers and is formed to a thickness of 0.5 to 6 millimeters. In addition, since it contains the above-described UV curable adhesive composition, transparency is improved through suppression of blistering and improvement of yellowing, and the curing rate of the inside and surface of the adhesive is high. When a UV curable adhesive in liquid form is injected between the substrate layers and cured with a UV curing machine, it is cured into a solid form and serves to adhere the substrate layers.
(2) 기재층 (2) base layer
기재층은 상기 이종 접합시트의 기재를 이루는 층으로, 기재층의 종류에는 제한이 없으나, 폴리메틸메타아크릴레이트(PMMA), 폴리카보네이트(PC), 아크릴로니트릴부타디엔스티렌 공중합체 또는 강화유리에서 선택되는 것이 바람직하다. The substrate layer is a layer constituting the substrate of the heterojunction sheet, and the type of the substrate layer is not limited, but is selected from polymethyl methacrylate (PMMA), polycarbonate (PC), acrylonitrile butadiene styrene copolymer, or tempered glass. it is desirable to be
상기 기재층은 2층 내지 5층으로 적층되는 것이 바람직하며, 복수의 기재층들 사이에는 상기의 접착층이 각각 형성될 수 있다.The substrate layer is preferably laminated in two to five layers, and the adhesive layer may be formed between the plurality of substrate layers, respectively.
상기 기재층의 두께는 적층되는 기재층의 수에 따라 달라질 수 있으며, 1 내지 20 밀리미터인 것이 바람직하다. 1 밀리미터 미만인 경우에는 이종 접합시트의 내구성이 저하되며, 20 밀리미터를 초과하는 경우에는 지나치게 두꺼워져 외력을 받은 경우에 기재층에 파편이 쉽게 형성될 수 있다.The thickness of the base layer may vary depending on the number of laminated base layers, and is preferably 1 to 20 millimeters. If the thickness is less than 1 millimeter, the durability of the heterojunction sheet is reduced, and if it exceeds 20 millimeters, it becomes too thick and fragments may be easily formed in the substrate layer when an external force is applied.
이상 본 발명의 바람직한 실시예를 설명하였지만, 본 명세서에 기재된 구성은 본 발명의 가장 바람직한 일 실시예에 불과할 뿐이고 본 발명의 기술적 사상을 모두 대변하는 것은 아니므로, 본 출원시점에 있어서 이들을 대체할 수 있는 다양한 균등물과 변형예들이 있을 수 있음을 이해하여야 한다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적인 것이 아닌 것으로서 이해되어야 하고, 본 발명의 범위는 상세한 설명보다는 후술하는 특허청구범위에 의하여 나타내어지며, 특허청구범위의 의미 및 범위 그리고 그 등가 개념으로부터 도출되는 모든 변경 또는 변형된 형태가 본 발명의 범위에 포함되는 것으로 해석되어야 한다.Although the preferred embodiments of the present invention have been described above, the configuration described in this specification is only one of the most preferred embodiments of the present invention and does not represent all of the technical ideas of the present invention, so they can be substituted at the time of this application. It should be understood that there may be many equivalents and variations. Therefore, the embodiments described above should be understood as illustrative and not restrictive in all respects, and the scope of the present invention is indicated by the claims to be described later rather than the detailed description, and the meaning and scope of the claims and their All changes or modified forms derived from equivalent concepts should be construed as being included in the scope of the present invention.
Claims (8)
아크릴레이트 모노머;
광개시제; 및
첨가제를 포함하며,
상기 광개시제는 단파장 광개시제와 장파장 광개시제를 배합하여 사용하며,
상기 첨가제는 자외선 반응성 유무기 화합물, 적외선 차단 성분 및 자외선 흡수 성분으로 이루어진 군에서 선택된 어느 하나 이상인 UV 경화형 접착제.
urethane acrylate oligomers;
acrylate monomer;
photoinitiators; and
contains additives,
The photoinitiator is used by combining a short-wavelength photoinitiator and a long-wavelength photoinitiator,
The additive is at least one UV curable adhesive selected from the group consisting of a UV-reactive organic-inorganic compound, an infrared ray blocking component, and a UV absorbing component.
상기 UV 경화형 접착제 전체 100 중량부에 대하여, 상기 우레탄 아크릴레이트 올리고머 10 내지 50 중량부, 상기 아크릴레이트 모노머 50 내지 80 중량부 및 상기 광개시제 0.1 내지 5 중량부로 포함되는 것을 특징으로 하는 UV 경화형 접착제.
According to claim 1,
Based on the total 100 parts by weight of the UV curable adhesive, 10 to 50 parts by weight of the urethane acrylate oligomer, 50 to 80 parts by weight of the acrylate monomer and 0.1 to 5 parts by weight of the photoinitiator UV curable adhesive.
상기 우레탄 아크릴레이트 올리고머의 평균 분자량은 1000 내지 3000g/mol 인 UV 경화형 접착제.
According to claim 1,
The average molecular weight of the urethane acrylate oligomer is 1000 to 3000g / mol UV curable adhesive.
상기 자외선 반응성 유무기입자는 하기의 구조식(1)인 UV 경화형 접착제.
[구조식(1)]
(상기의 [구조식 1]에서 실리카입자는 와 같은 망상구조를 나타내며, 상기 R은 C2 ~ C20의 지방족 또는 지환족 알킬기, 방향족 구조의 화합물을 나타내며, Acryl은 아크릴 화합물이다. )
According to claim 1,
The ultraviolet-reactive organic-inorganic particles are UV curable adhesives of the following structural formula (1).
[Structural formula (1)]
(In [Structural Formula 1] above, the silica particles are Represents a network structure such as, wherein R represents a C2 ~ C20 aliphatic or alicyclic alkyl group, an aromatic compound, and Acryl is an acrylic compound. )
상기 접착층의 양면에 형성되는 기재층을 포함하는 UV 경화형 접착제를 포함하는 이종 접합시트.
An adhesive layer comprising the UV curable adhesive of any one of claims 1 to 4; and
A heterojunction sheet comprising a UV curable adhesive comprising a substrate layer formed on both sides of the adhesive layer.
상기 기재층은 폴리메틸메타아크릴레이트, 폴리카보네이트, 아크릴로니트릴부타디엔스티렌 공중합체 또는 강화유리로 이루어진 그룹에서 선택되는 어느 하나인 것을 특징으로 하는 UV 경화형 접착제를 포함하는 이종 접합시트.
According to claim 5,
The base layer is a heterojunction sheet comprising a UV curable adhesive, characterized in that any one selected from the group consisting of polymethyl methacrylate, polycarbonate, acrylonitrile butadiene styrene copolymer or tempered glass.
상기 기재층은 2층 내지 5층으로 형성되며, 복수의 상기 기재층 사이에는 상기의 접착층이 각각 형성되는 것을 특징으로 하는 UV 경화형 접착제를 포함하는 이종 접합시트.
According to claim 5,
The heterojunction sheet comprising a UV curable adhesive, characterized in that the base layer is formed of 2 to 5 layers, and the adhesive layer is formed between the plurality of base layers, respectively.
상기 UV 경화형 접착제를 포함하는 이종 접합시트는 방범이나 방탄시트 용도로 사용되는 것을 특징으로 하는 UV 경화형 접착제를 포함하는 이종 접합시트.According to claim 5,
The heterojunction sheet containing the UV curable adhesive is a heterojunction sheet containing a UV curable adhesive, characterized in that used for crime prevention or bulletproof sheet.
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KR101000131B1 (en) | 2008-12-18 | 2010-12-10 | 박주순 | acrylic union method |
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KR101956661B1 (en) * | 2016-01-19 | 2019-03-11 | 고오 가가쿠고교 가부시키가이샤 | Photosensitive resin composition, dry film and printed wiring board |
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KR100545629B1 (en) | 2004-03-18 | 2006-01-24 | 박재웅 | Process of manufacturing acrylate samples |
KR101000131B1 (en) | 2008-12-18 | 2010-12-10 | 박주순 | acrylic union method |
KR20130096389A (en) * | 2012-02-22 | 2013-08-30 | 계명대학교 산학협력단 | Uv coating resin for protecting electrode |
KR20140103856A (en) * | 2013-02-18 | 2014-08-27 | 아사히 가라스 가부시키가이샤 | Curable resin composition, adhesive layer-equipped transparent surface material, and laminate |
KR20170059800A (en) * | 2015-11-23 | 2017-05-31 | 한국신발피혁연구원 | Ultraviolet curable acrylic hybrid adhesive composition for acrylic panel lamination |
KR101956661B1 (en) * | 2016-01-19 | 2019-03-11 | 고오 가가쿠고교 가부시키가이샤 | Photosensitive resin composition, dry film and printed wiring board |
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