KR102572867B1 - Optically transparent and high modulus adhesive sheet - Google Patents
Optically transparent and high modulus adhesive sheet Download PDFInfo
- Publication number
- KR102572867B1 KR102572867B1 KR1020210170961A KR20210170961A KR102572867B1 KR 102572867 B1 KR102572867 B1 KR 102572867B1 KR 1020210170961 A KR1020210170961 A KR 1020210170961A KR 20210170961 A KR20210170961 A KR 20210170961A KR 102572867 B1 KR102572867 B1 KR 102572867B1
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- parts
- acrylate
- urethane acrylate
- semi
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 22
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 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 27
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000012790 adhesive layer Substances 0.000 claims abstract description 15
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 13
- 238000010030 laminating Methods 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 71
- -1 2-ethylhexyl Chemical group 0.000 claims description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- 229920001451 polypropylene glycol Polymers 0.000 claims description 9
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 7
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical group C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 6
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical group C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 230000003287 optical effect Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 5
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 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
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 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 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 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
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- 230000008901 benefit Effects 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003085 diluting agent Substances 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
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012855 volatile organic compound Substances 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
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-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
- 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
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 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
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-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
- 239000004971 Cross linker Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
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- 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
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- 238000003475 lamination Methods 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
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester 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
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002040 relaxant effect Effects 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
- 239000012780 transparent material Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Abstract
개시된 내용은 높은 모듈러스를 가지며, 우수한 광학특성 및 시트재와의 우수한 점착력을 가지는 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트에 관한 것이다.
개시된 내용은 우레탄 아크릴레이트 올리고머, 아크릴 모노머 혼합물, 광개시제 및 가교제를 포함하는 조성물에 1차 경화를 진행하여 제조된 반경화 접착층을 포함하며, 상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트를 일 실시예로 제시한다.The disclosed content relates to an optically transparent and high modulus adhesive sheet having high modulus, excellent optical properties, and excellent adhesion to a sheet material.
The disclosed content includes a semi-cured adhesive layer prepared by performing primary curing on a composition containing a urethane acrylate oligomer, an acrylic monomer mixture, a photoinitiator, and a crosslinking agent, and laminating the semi-cured adhesive layer to a sheet material and performing secondary curing An optically transparent adhesive sheet having a high modulus manufactured by the above method is presented as an embodiment.
Description
개시된 내용은 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트에 관한 것이다.The disclosed content relates to an adhesive sheet that is optically transparent and has a high modulus.
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.
종래의 일반적인 UV시럽(부분중합물, UV 조사 중합) 기반의 광학적으로 투명한 접착제(OCA)는 매우 낮은 모듈러스 수준(100,000Pa 이하)을 보이기 때문에, 높은 모듈러스를 요하는 분야에서는 그 적용에 한계가 있었다. Conventional general UV syrup (partial polymer, UV irradiation polymerization)-based optically clear adhesives (OCA) show a very low modulus level (less than 100,000 Pa), so their application is limited in fields requiring high modulus.
또한 다양한 분야에서 응용이 가능한 범용 용제형 아크릴 접착제의 모듈러스가 100,000Pa 이하의 수준에 불과할 뿐만 아니라, 코팅 두께의 한계성 및 휘발성유기화합물(VOC)이 발생하는 문제가 있었다. In addition, the modulus of the general-purpose solvent-type acrylic adhesive that can be applied in various fields is only 100,000Pa or less, and there are problems in that the coating thickness is limited and volatile organic compounds (VOCs) are generated.
개시된 발명은 높은 모듈러스를 가지며, 우수한 광학특성 및 시트재와의 우수한 점착력을 가지는 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트를 제공하고자 한다.The disclosed invention is intended to provide an optically transparent, high modulus adhesive sheet having high modulus, excellent optical properties and excellent adhesion to sheet materials.
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, 아크릴 모노머 혼합물, 광개시제 및 가교제를 포함하는 조성물에 1차 경화를 진행하여 제조된 반경화 접착층을 포함하며, 상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트를 일 실시예로 제시한다.The disclosed content includes a semi-cured adhesive layer prepared by performing primary curing on a composition containing a urethane acrylate oligomer, an acrylic monomer mixture, a photoinitiator, and a crosslinking agent, and laminating the semi-cured adhesive layer to a sheet material and performing secondary curing An optically transparent adhesive sheet having a high modulus manufactured by the above method is presented as an embodiment.
개시된 내용의 특징에 따르면, 상기 접착시트의 상기 2차 경화 후의 모듈러스가 106~1010 Pa인 것을 특징으로 하는 것일 수 있다.According to the disclosed features, the modulus of the adhesive sheet after the secondary curing may be 10 6 to 10 10 Pa.
또한 상기 우레탄 아크릴레이트 올리고머의 중량평균분자량이 4,000 g/mol 내지 200,000 g/mol인 것일 수 있다.In addition, the urethane acrylate oligomer may have a weight average molecular weight of 4,000 g/mol to 200,000 g/mol.
또한 상기 우레탄 아크릴레이트 올리고머 50 중량부에 대하여, 상기 아크릴 모노머 혼합물 10~90 중량부, 광개시제 0.01~5 중량부 및 가교제 0.1~15 중량부를 포함하는 것일 수 있다.In addition, based on 50 parts by weight of the urethane acrylate oligomer, 10 to 90 parts by weight of the acrylic monomer mixture, 0.01 to 5 parts by weight of a photoinitiator, and 0.1 to 15 parts by weight of a crosslinking agent may be included.
개시된 내용의 일 실시예에 따른 광학적으로 투명하고 높은 모듈러스를 갖는접착시트에 의하면, 높은 모듈러스를 가지며, 우수한 광학특성 및 시트재와의 우수한 점착력을 가진다는 장점이 있다.According to the optically transparent and high modulus adhesive sheet according to one embodiment of the disclosed subject matter, it has a high modulus, excellent optical properties and excellent adhesive strength with the sheet material. There are advantages.
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.
도 1은 모듈러스 향상 메커니즘에 대한 그래프를 나타낸다.
도 2는 반경화 접착층을 시트재에 합지한 후 2차 경화(완경화)를 진행하는 공정을 나타낸다.1 shows a graph for the modulus enhancement mechanism.
2 shows a process of laminating a semi-cured adhesive layer to a sheet material and then performing secondary curing (relaxing curing).
이하, 첨부된 도면을 참조하여 개시된 내용의 바람직한 실시예의 구성 및 작용효과에 대하여 살펴본다. 참고로, 이하 도면에서, 각 구성요소는 편의 및 명확성을 위하여 생략되거나 개략적으로 도시되었으며, 각 구성요소의 크기는 실제 크기를 반영하는 것은 아니다. 또한 명세서 전체에 걸쳐 동일 참조 부호는 동일 구성요소를 지칭하며 개별 도면에서 동일 구성에 대한 도면 부호는 생략하기로 한다.Hereinafter, with reference to the accompanying drawings, look at the configuration and operation effects of preferred embodiments of the disclosed contents. For reference, in the drawings below, each component is omitted or schematically illustrated for convenience and clarity, and the size of each component does not reflect the actual size. In addition, like reference numerals refer to like components throughout the specification, and reference numerals for like components in individual drawings will be omitted.
본 명세서에서 '점착'과 '접착'은 혼용해서 사용될 수 있다.In this specification, 'adhesion' and 'adhesion' may be used interchangeably.
또한 본 명세서에서 광학적으로 투명한 접착제는 OCA(Optically Clear Adhesive)로 호칭하는 경우가 있다. Also, in the present specification, an optically clear adhesive may be referred to as optically clear adhesive (OCA).
본 명세서에 개시된 광학적으로 투명하고 높은 모듈러스를 갖는 접착시트는 우레탄 아크릴레이트 올리고머, 아크릴 모노머 혼합물, 광개시제 및 가교제를 포함하는 조성물에 1차 경화를 진행하여 제조된 반경화 접착층을 포함하며, 상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 것을 특징으로 한다.The optically transparent adhesive sheet having a high modulus disclosed herein includes a semi-cured adhesive layer prepared by performing primary curing on a composition containing a urethane acrylate oligomer, an acrylic monomer mixture, a photoinitiator, and a crosslinking agent, wherein the semi-cured It is characterized in that it is manufactured by laminating the adhesive layer to the sheet material and proceeding with secondary curing.
상기 시트재는 상기 반경화 필름이 부착되는 기재로, 그 종류에는 제한이 없으며 예를 들면 유리(glass), 스테인레스 강(SUS), 폴리에틸렌테레프탈레이트(Polyethylene terephthalate, PET), 폴리카보네이트(Polycarbonate, PC) 등을 사용할 수 있으며, 점착력 측면에서 유리(glass) 및 스테인레스 강(SUS)을 사용하는 것이 바람직하다.The sheet material is a substrate to which the semi-cured film is attached, and the type is not limited. For example, glass, stainless steel (SUS), polyethylene terephthalate (PET), polycarbonate (PC) etc. can be used, and it is preferable to use glass and stainless steel (SUS) in terms of adhesive strength.
상기 1차 경화 및 상기 2차 경화는 에너지선을 조사하는 것일 수 있으며, 자외선(UV) 조사가 바람직하다.The primary curing and the secondary curing may be irradiation with energy rays, preferably ultraviolet (UV) irradiation.
상기 광학적으로 투명한 접착시트의 상기 2차 경화 후의 모듈러스는 106~1010 Pa인 것을 특징으로 하여, 종래보다 100배 이상 높은 모듈러스를 가진다. 구체적으로, 상기 1차 경화를 통해 제조된 반경화 필름의 상태에서는 모듈러스가 낮아 시트재와의 합지가 용이해 필름의 들뜸을 방지할 수 있고, 합지 후 2차 경화를 통해 완경화되는 경우에는 모듈러스가 증가하여 내충격성을 증가시킬 수 있다. 높은 모듈러스와 광학특성을 갖기 때문에 내충격성 및 폴딩 특성을 요하는 디스플레이 분야에서의 적용이 가능하다는 장점이 있다. (도 1 및 도 2)The modulus of the optically transparent adhesive sheet after the secondary curing is 10 6 to 10 10 Pa, and has a modulus 100 times higher than that of the prior art. Specifically, in the state of the semi-cured film manufactured through the primary curing, the modulus is low, and lamination with the sheet material is easy to prevent the film from lifting. can be increased to increase the impact resistance. Since it has high modulus and optical characteristics, it has the advantage that it can be applied in the display field requiring impact resistance and folding characteristics. (FIGS. 1 and 2)
이하, 상기 반경화 접착층에 포함되는 구성을 보다 상세하게 설명한다.Hereinafter, configurations included in the semi-cured adhesive layer will be described in more detail.
1. 우레탄 아크릴레이트(polyurethane acrylate, PUA) 올리고머1. Polyurethane acrylate (PUA) oligomer
본 발명에서 개시하는 우레탄 아크릴레이트 올리고머는 자외선(UV) 경화형 아크릴레이트 중에서도 물리적 특성, 저온에서의 유연성, 내마모성, 투명도 및 경도조절의 용이성으로 인하여 가장 많이 이용되는 올리고머에 해당한다. The urethane acrylate oligomer disclosed in the present invention corresponds to the most widely used oligomer among ultraviolet (UV) curable acrylates due to its physical properties, flexibility at low temperatures, abrasion resistance, transparency, and ease of hardness control.
상기 우레탄 아크릴레이트 올리고머는 중량평균분자량(Mw)이 4,000 g/mol 내지 200,000 g/mol인 것일 수 있다. 중량평균분자량이 4,000g/mol 미만인 경우에는 접착에 의한 경도 향상효과가 낮아지는 문제가 발생할 수 있으며, 중량평균분자량이 200,000g/mol을 초과하는 경우에는 지나치게 높은 점도에 의해 작업성 저하가 발생할 수 있다.remind Urethane acrylate oligomers It may have a weight average molecular weight (Mw) of 4,000 g/mol to 200,000 g/mol. If the weight average molecular weight is less than 4,000 g / mol, there may be a problem that the hardness improvement effect due to adhesion is lowered, and if the weight average molecular weight exceeds 200,000 g / mol, workability may be deteriorated due to excessively high viscosity. there is.
상기 우레탄 아크릴레이트 올리고머는 폴리올과 이소시아네이트를 중합시켜 폴리우레탄 예비중합체를 합성한 후, 아크릴레이트 모노머와 캡핑(capping) 반응을 통해 제조된 것일 수 있다. The urethane acrylate oligomer may be prepared by synthesizing a polyurethane prepolymer by polymerizing a polyol and isocyanate, and then performing a capping reaction with an acrylate monomer.
상기 폴리올은 본 발명의 기술분야에서 일반적으로 사용되는 것이라면 그 종류에는 제한이 없으나, 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, 폴리에스테르글리콜, 폴리에테르글리콜, 폴리카보네이트글리콜, 폴리에틸렌글리콜, 폴리프로필렌글리콜, 아민 말단화된 폴리에테르, 폴리트리메틸렌 에테르글리콜, 폴리트리메틸렌 에테르에스테르 글리콜, 폴리트리메틸렌-co-에틸렌 에테르글리콜 및 폴리테트라메틸렌 에테르글리콜로 이루어진 군에서 선택된 어느 하나 이상을 사용하는 것이 가능하며, 바람직하게는 폴리프로필렌글리콜(Polypropyleneglycol)을 사용할 수 있다. 또한 상기 폴리올의 중량평균 분자량은 300g/mol 내지 8,000 g/mol 일 수 있으나, 이에 한정되는 것은 아니다. The type of the polyol is not limited as long as it is generally used in the technical field of the present invention, but 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, polyester glycol, polyether glycol, polycarbonate Any one selected from the group consisting of glycol, polyethylene glycol, polypropylene glycol, amine-terminated polyether, polytrimethylene ether glycol, polytrimethylene ether ester glycol, polytrimethylene-co-ethylene ether glycol and polytetramethylene ether glycol It is possible to use one or more, and preferably polypropylene glycol can be used. In addition, the polyol may have a weight average molecular weight of 300 g/mol to 8,000 g/mol, but is not limited thereto.
상기 이소시아네이트는 지방족 이소시아네이트, 방향족 이소시아네이트 등을 그 종류에 제한이 없이 사용 가능하다. 상기 지방족 이소시아네이트로는 이소포론 디이소시아네이트(Isophorone Diisocyanate, IPDI), 헥사메틸렌 디이소시아네이트(hexamethylene Diisocyanate, 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, 바람직하게는 이소포론 디이소시아네이트(Isophorone Diisocyanate, IPDI) 또는 헥사메틸렌 디이소시아네이트(hexamethylene Diisocyanate, HDI)를 사용할 수 있다. 또 상기 치환족 이소시아네이트로는 톨릴렌 디이소시아네이트, 크실릴렌 디이소시아네이트, 메틸렌디페닐 디이소시아네이트, 페닐렌 디이소시아네이트, 나프탈렌 디이소시아네이트, 자일릴렌 디이소시아네이트(Xylylene Diisocyanate, XDI) 등을 사용할 수 있으며, 바람직하게는 자일릴렌 디이소시아네이트(Xylylene Diisocyanate, XDI)를 사용할 수 있다.As the isocyanate, an aliphatic isocyanate, an aromatic isocyanate, and the like may be used without limitation. The aliphatic isocyanate includes isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), 4,4-dicyclohexylmethanediisocyanate (H12MDI), 3-iso Cyanatomethyl-3,5,5-tricyclohexyl isocyanate (3-isocyanatomethyl- 3,5,5-trimethylcyclohexylisocyanate (IPDI), 1,4-cyclohexyl diisocyanate (CHDI) and 2,2,4-trimethylhexamethylene diisocyanate (2,2,4-trimethylhexamethylene diisocyanate, TMDI) and the like can be used, preferably isophorone diisocyanate (IPDI) or hexamethylene diisocyanate , HDI) can be used. In addition, tolylene diisocyanate, xylylene diisocyanate, methylene diphenyl diisocyanate, phenylene diisocyanate, naphthalene diisocyanate, xylylene diisocyanate (XDI), etc. may be used as the substituted isocyanate, preferably Preferably, xylylene diisocyanate (XDI) may be used.
상기 아크릴레이트 모노머는 치환기의 종류에 따라 알킬 아크릴레이트 모노머, 히드록시기를 함유한 아크릴레이트 모노머, 글리시딜기를 함유한 아크릴레이트 모노머, 카르복시기를 함유한 아크릴레이트 모노머 또는 질소성분을 함유한 아크릴레이트 모노머를 선택할 수 있으나 이에 한정되는 것은 아니며, 바람직하게는 히드록시기(-OH)를 함유한 아크릴레이트 모노머를 선택할 수 있다.The acrylate monomer is an alkyl acrylate monomer, a hydroxyl group-containing acrylate monomer, a glycidyl group-containing acrylate monomer, a carboxyl group-containing acrylate monomer, or a nitrogen-containing acrylate monomer, depending on the type of substituent. It may be selected, but is not limited thereto, and preferably, an acrylate monomer containing a hydroxyl group (-OH) may be selected.
상기 히드록시기를 함유한 아크릴레이트 모노머란 아크릴산, 2-히드록시에틸 메타아크릴레이트, 히드록시에틸 메타아크릴레이트 2-히드록시에틸 아크릴레이트, 4-히드록시부틸 아크릴레이트, 2-히드록시 프로필아크릴레이트, 히드록시프로필 아크릴레이트, 히드록시(메타)아크릴레이트, 히드록시(메타)메틸아크릴레이트, 테트라하이드로푸르푸릴 아크릴레이트, 히드록시부틸 아크릴레이트 및 2-히드록시-3-페녹시프로필 아크릴레이트로 이루어지는 군에서 선택되는 어느 하나 이상을 선택할 수 있다. 바람직하게는 2-히드록시에틸 메타아크릴레이트, 2-히드록시에틸 아크릴레이트, 4-히드록시부틸 아크릴레이트 또는 2-하이드록시 프로필아크릴레이트를 사용할 수 있다.The hydroxy group-containing acrylate monomer includes acrylic acid, 2-hydroxyethyl methacrylate, hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxypropyl acrylate, Consisting of hydroxypropyl acrylate, hydroxy (meth) acrylate, hydroxy (meth) methyl acrylate, tetrahydrofurfuryl acrylate, hydroxybutyl acrylate and 2-hydroxy-3-phenoxypropyl acrylate Any one or more selected from the group may be selected. Preferably, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate or 2-hydroxypropyl acrylate may be used.
2. 아크릴 모노머 혼합물2. Acrylic monomer mixture
아크릴 모노머 혼합물은 상기 우레탄 아크릴레이트 올리고머를 저점도화하여 작업성을 향상시키는 반응성 희석제의 역할을 한다. 상기 아크릴 모노머 혼합물에는 단관능성 및 다관능성 아크릴레이트 모노머가 포함될 수 있으며, 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. The acrylic monomer mixture is a reactive diluent that improves workability by lowering the viscosity of the urethane acrylate oligomer. play a role The acrylic monomer mixture may include monofunctional and multifunctional acrylate monomers, and monofunctional Acrylate monomers have high flexibility and can improve transparency by suppressing yellowing, and since multifunctional acrylate monomers exhibit high modulus of elasticity due to enhancement of crosslinking density, acrylate monomers suitable for the purpose can be appropriately selected.
단관능성 아크릴레이트 모노머로는 그 종류에 제한이 없으나 아크릴산, 아크릴로일 모폴린, 2-히드록시에틸 (메타)아크릴레이트, 히드록시에틸 (메타)아크릴레이트, 4-히드록시부틸 아크릴레이트, 2-히드록시 프로필아크릴레이트, 히드록시프로필 아크릴레이트, 히드록시(메타)아크릴레이트, 히드록시(메타)메틸아크릴레이트, 테트라하이드로푸르푸릴 아크릴레이트, 히드록시부틸 아크릴레이트, 2-히드록시-3-페녹시프로필 아크릴레이트, 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)아크릴레이트, 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 이상을 사용할 수 있다. The monofunctional acrylate monomer is not limited in its kind, but acrylic acid, acryloyl morpholine, 2-hydroxyethyl (meth)acrylate, hydroxyethyl (meth)acrylate, 4-hydroxybutyl acrylate, 2 -hydroxy propyl acrylate, hydroxypropyl acrylate, hydroxy (meth) acrylate, hydroxy (meth) methyl acrylate, tetrahydrofurfuryl acrylate, hydroxybutyl acrylate, 2-hydroxy-3- Phenoxypropyl acrylate, 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, dicyclopentadiene (meth)acrylate , diacetone (meth)acrylamide, diethylaminoethyl (meth)acrylate, lauryl (meth)acrylate, methoxyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxy poly Propylene glycol (meth)acrylate, methyl (meth)acrylate, benzyl (meth)acrylate, bornyl (meth)acrylate, butoxyethyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (metha)acrylate )Acrylate, steeryl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, ethyl (meth)acrylate, epoxydiethylene glycol (meth)acrylate, octadecyl (meth)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 (meth)acrylate , At least one selected from the group consisting of hydroxyethyl (meth)acrylate may be used.
다관능성 아크릴레이트 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 이상을 사용할 수 있다. The multifunctional acrylate monomer is not limited in its kind, but 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropanetrioxyethyl At least one selected from the group consisting of (meth)acrylate, tricyclodecane dimethanol diacrylate, tripropylene glycol diacrylate, and pentaerythritol tri(meth)acrylate may be used.
상기 우레탄 아크릴레이트 올리고머 50 중량부에 대하여, 상기 아크릴 모노머 혼합물은 10~90 중량부로 포함되는 것일 수 있다. 10 중량부 미만으로 포함되는 경우에는 반응성 희석제로서의 역할을 수행하기에 충분하지 않으며, 90 중량부를 초과하여 포함되는 경우에는 접착제의 점도가 낮아져 경화시간이 길어지는 문제점이 있다.Based on 50 parts by weight of the urethane acrylate oligomer, the acrylic monomer mixture may be included in 10 to 90 parts by weight. If it is included in less than 10 parts by weight, it is not sufficient to serve as a reactive diluent, and if it is included in more than 90 parts by weight, the viscosity of the adhesive is lowered and the curing time is prolonged.
3. 광개시제3. Photoinitiator
광개시제는 빛을 흡수하여 라디칼을 생성한 후 개시하며, UV 조사에 의해 우레탄 아크릴레이트 올리고머 혹은 아크릴레이트 모노머가 중합될 수 있도록 하는 역할을 하는 것으로, 광조사에 의해 라디칼을 발생시켜 중합 반응을 개시시킬 수 있는 것이라면 그 종류에 제한되지 않고 사용될 수 있다. 예를 들어 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-히드록시사이클로헥실페닐 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.The photoinitiator initiates after generating radicals by absorbing light, and serves to polymerize urethane acrylate oligomers or acrylate monomers by UV irradiation, generating radicals by light irradiation to initiate polymerization. Anything that can be used can be used without being limited to its type. For example, one or more selected from among 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 ketone, benzaldehyde, anthraquinone, 3-methylacetophenone, 1-(4-isopropyl-phenol) -2-hydroxy-2-methyl propan-1-one, thioxanthone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, benzoin propyl ether, benzo At least one selected from the group consisting of ethyl ether and mixtures thereof may be used, and commercial photoinitiators include Ciba Geigy (Klybecstrasse 141, Basle, Baslestadt, 4002, Switzerland) Irgacure 127, 184, 250, 369, 379, 651, 500, 754, 784, 819, 819DW, 907, 1300, 1700, 1800, 2022, 2100, 2959, etc. One of these may be used alone, but two or more may be mixed and used.
상기 우레탄 아크릴레이트 올리고머 50 중량부에 대하여, 상기 광개시제는 0.01~5 중량부로 포함되는 것일 수 있다. 0.01 중량부 미만으로 포함되는 경우에는 중합 속도가 느리고 전환율이 낮으며, 5 중량부를 초과하여 포함되는 경우에는 점착제의 물성이 저하된다.With respect to 50 parts by weight of the urethane acrylate oligomer, the photoinitiator may be included in 0.01 to 5 parts by weight. When included in less than 0.01 parts by weight, the polymerization rate is slow and the conversion rate is low, and when included in more than 5 parts by weight, the physical properties of the pressure-sensitive adhesive are deteriorated.
4. 가교제4. Crosslinker
가교제는 아크릴 혼합물의 가교반응을 유도하여 점착제 조성물의 경화시간을 단축시키는 역할을 하는 것이다.The crosslinking agent serves to shorten the curing time of the pressure-sensitive adhesive composition by inducing a crosslinking reaction of the acrylic mixture.
상기 가교제로는 1,6-헥산디올 디아크릴레이트(1,6-Hexanediol diacrylate), 펜타에리트리톨 테트라아크릴레이트 (Pentaerythritol tetraacrylate), 트리메틸올프로판 트리아크릴레이트(Trimethylolpropane triacrylate), 트리스(2-히드록시에틸) 이소시아누레이트 트리아크릴레이트(Tris(2-hydroxy ethyl) isocyanurate triacrylate) 로 이루어진 그룹에서 선택되는 하나 이상을 사용하는 것이 바람직하나, 이에 한정되는 것은 아니다.The crosslinking agent includes 1,6-hexanediol diacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, tris (2-hydroxy It is preferable to use at least one selected from the group consisting of ethyl) isocyanurate triacrylate (Tris(2-hydroxy ethyl) isocyanurate triacrylate), but is not limited thereto.
상기 우레탄 아크릴레이트 올리고머 50 중량부에 대하여, 상기 가교제는 0.1~15 중량부로 포함되는 것이 바람직하다. With respect to 50 parts by weight of the urethane acrylate oligomer, the crosslinking agent is preferably included in an amount of 0.1 to 15 parts by weight.
[우레탄 아크릴레이트 올리고머의 제조][Preparation of Urethane Acrylate Oligomer]
폴리프로필렌 글리콜(Polypropylene glycol; PPG, 분자량 2,000 g/mol) 81.8 중량부와 이소포론 디이소시아네이트(Isophorone diisocyanate; IPDI) 18.2 중량부로 질소 분위기 하에서 60℃에서 2시간 반응을 통해, 이소시아네이트를 말단으로 갖는 우레탄 예비중합체를 제조한 후, 2-히드록시에틸 아크릴레이트로 캡핑(capping) 하는 반응을 45℃ 조건에서 4시간 진행하였다. 상기의 방법으로 아크릴레이트 관능기가 2인 (functionality = 2) 우레탄 아크릴레이트 올리고머를 제조한다.Polypropylene glycol (PPG, molecular weight 2,000 g / mol) 81.8 parts by weight and isophorone diisocyanate (IPDI) 18.2 parts by weight at 60 ° C. for 2 hours in a nitrogen atmosphere through a reaction, urethane having an isocyanate as a terminal After preparing the prepolymer, a capping reaction with 2-hydroxyethyl acrylate was performed at 45° C. for 4 hours. By the above method, a urethane acrylate oligomer having 2 acrylate functional groups (functionality = 2) is prepared.
[실시예 1][Example 1]
상기에서 제조한 우레탄 아크릴레이트 올리고머 30 중량부, 아크릴 모노머 혼합물 70 중량부 (아크릴 모노머 혼합비= 이소보닐 메타아크릴레이트 70 중량부 / 벤질 메타아크릴레이트 20 중량부 / 아크릴산 10 중량부), 광개시제로 Irgacure 651 0.1 중량부 및 가교제로 1,6-헥산디올 디아크릴레이트 1 중량부를 혼합한다. 상기 혼합물을 50㎛ 두께로 코팅한 후에, UV를 조사하여 반경화 OCA를 제조한다. 상기 반경화 OCA를 피착재에 합지한 후, UV 조사를 통해서 완경화 OCA를 제조한다.30 parts by weight of the urethane acrylate oligomer prepared above, 70 parts by weight of the acrylic monomer mixture (acrylic monomer mixing ratio = 70 parts by weight of isobornyl methacrylate / 20 parts by weight of benzyl methacrylate / 10 parts by weight of acrylic acid), Irgacure 651 as a photoinitiator 0.1 part by weight and 1 part by weight of 1,6-hexanediol diacrylate as a crosslinking agent are mixed. After coating the mixture to a thickness of 50 μm, UV irradiation was performed to prepare a semi-cured OCA. After laminating the semi-cured OCA to an adherend, a slightly cured OCA is prepared through UV irradiation.
[실시예 2][Example 2]
우레탄 아크릴레이트 올리고머 30 중량부, 아크릴 모노머 혼합물 70 중량부 (아크릴 모노머 혼합비= 2-에틸헥실 (메타)아크릴레이트 5 중량부 / 이소보닐 메타아크릴레이트 59 중량부 / 벤질 메타아크릴레이트 9 중량부/ 테트라하이드로푸르푸릴 아크릴레이트 9 중량부 / 아크릴로일 모폴린 9 중량부 / 아크릴산 9 중량부), 광개시제로 Irgacure 651 0.1 중량부 및 가교제로 1,6-헥산디올 디아크릴레이트 1.5 중량부를 혼합한다. 상기 혼합물을 50㎛ 두께로 코팅한 후에, UV를 조사하여 반경화 OCA를 제조한다. 상기 반경화 OCA를 피착재에 합지한 후, UV 조사를 통해서 완경화 OCA를 제조한다.30 parts by weight of urethane acrylate oligomer, 70 parts by weight of acrylic monomer mixture (mixing ratio of acrylic monomer = 5 parts by weight of 2-ethylhexyl (meth)acrylate / 59 parts by weight of isobornyl methacrylate / 9 parts by weight of benzyl methacrylate / tetra 9 parts by weight of hydrofurfuryl acrylate / 9 parts by weight of acryloyl morpholine / 9 parts by weight of acrylic acid), 0.1 part by weight of Irgacure 651 as a photoinitiator and 1.5 parts by weight of 1,6-hexanediol diacrylate as a crosslinking agent are mixed. After coating the mixture to a thickness of 50 μm, UV irradiation was performed to prepare a semi-cured OCA. After laminating the semi-cured OCA to an adherend, a slightly cured OCA is prepared through UV irradiation.
[실시예 3][Example 3]
우레탄 아크릴레이트 올리고머 50 중량부, 아크릴 모노머 혼합물 50 중량부 (아크릴 모노머 혼합비= 2-에틸헥실 아크릴레이트 20 중량부 / 이소보닐 메타아크릴레이트 55 중량부 / 벤질 메타아크릴레이트 15 중량부 / 아크릴산 10 중량부), 광개시제로 Irgacure 651 0.1 중량부를 혼합한다. 상기 혼합물을 50㎛ 두께로 코팅한 후에, UV를 조사하여 반경화 OCA를 제조한다. 상기 반경화 OCA를 피착재에 합지한 후, UV 조사를 통해서 완경화 OCA를 제조한다.Urethane acrylate oligomer 50 parts by weight, acrylic monomer mixture 50 parts by weight (acrylic monomer mixing ratio = 20 parts by weight of 2-ethylhexyl acrylate / 55 parts by weight of isobornyl methacrylate / 15 parts by weight of benzyl methacrylate / 10 parts by weight of acrylic acid ), and 0.1 part by weight of Irgacure 651 as a photoinitiator. After coating the mixture to a thickness of 50 μm, UV irradiation was performed to prepare a semi-cured OCA. After laminating the semi-cured OCA to an adherend, a slightly cured OCA is prepared through UV irradiation.
[비교예 1][Comparative Example 1]
에틸헥실 아크릴레이트(EHA) 60 중량부, 이소보닐 메타아크릴레이트(IBOA) 20 중량부 및 아크릴산(AA) 20 중량부의 혼합물에 광개시제인 Irgacure 184 0.05 중량부를 혼합 후, 질소 분위기에서 UV조사하여 부분중합물(UV 시럽)을 제조하였다. 상기 부분중합물 100 중량부에 1,6-헥산디올 디아크릴레이트 0.1 중량부 및 광개시제로 Irgacure 651 0.1 중량부를 혼합한 후, UV Coater를 적용하여 50㎛ 으로 코팅한다.After mixing 60 parts by weight of ethylhexyl acrylate (EHA), 0.05 parts by weight of Irgacure 184 as a photoinitiator in a mixture of 20 parts by weight of isobornyl methacrylate (IBOA) and 20 parts by weight of acrylic acid (AA), UV irradiation in a nitrogen atmosphere to obtain a partial polymer (UV syrup) was prepared. After mixing 0.1 parts by weight of 1,6-hexanediol diacrylate with 100 parts by weight of the partial polymer and 0.1 parts by weight of Irgacure 651 as a photoinitiator, a UV coater was applied to coat the mixture to a thickness of 50 μm.
[비교예 2][Comparative Example 2]
에틸헥실 아크릴레이트(EHA) 90 중량부 및 아크릴산(AA) 10 중량부로 부분중합물(UV 시럽)을 제조한 것 외에는 비교예 1과 동일하게 제조한다. It was prepared in the same manner as in Comparative Example 1 except that a partial polymer (UV syrup) was prepared with 90 parts by weight of ethylhexyl acrylate (EHA) and 10 parts by weight of acrylic acid (AA).
[비교예 3][Comparative Example 3]
2-에틸헥실아크릴레이트 47 중량부, 부틸아크릴레이트 47 중량부 및 아크릴산 6 중량부로 구성되는 단량체 혼합물에, 중합개시제로서 아조비스부틸니트릴(AIBN) 0.1 중량부를 투입 후, 질소 분위기 하, 67℃에서 7시간동안 반응하여 아크릴레이트 고분자량 중합체를 중합하였다.After adding 0.1 part by weight of azobisbutylnitrile (AIBN) as a polymerization initiator to a monomer mixture composed of 47 parts by weight of 2-ethylhexyl acrylate, 47 parts by weight of butyl acrylate and 6 parts by weight of acrylic acid, under a nitrogen atmosphere, at 67 ° C. Reacted for 7 hours to polymerize the acrylate high molecular weight polymer.
사이크로헥실아크릴레이트 94 중량부 및 아크릴산 6 중량부로 구성된 단량체 혼합물에 중합개시제로서 아조비스부틸니트릴(AIBN) 5 중량부를 투입 후, 질소 분위기에서 85℃에서 3시간 반응하여 아크릴레이트 올리고머를 중합하였다.After adding 5 parts by weight of azobisbutylnitrile (AIBN) as a polymerization initiator to a monomer mixture composed of 94 parts by weight of cyclohexyl acrylate and 6 parts by weight of acrylic acid, it was reacted at 85 ° C. for 3 hours in a nitrogen atmosphere to polymerize acrylate oligomers.
상기 아크릴레이트 고분자량 중합체 100 질량부, 상기 아크릴레이트 올리고머 30 중량부, TDI계 경화제 (상품명: NA-1045L, 코스모텍) 1.5 중량부, 에폭시 경화제 (상품명: NA-30, 코스모텍) 0.3 중량부를 혼합한다. 상기 혼합물에 solvent Coater를 적용하여 50㎛으로 건조 및 코팅한다.100 parts by weight of the acrylate high molecular weight polymer, 30 parts by weight of the acrylate oligomer, 1.5 parts by weight of a TDI curing agent (trade name: NA-1045L, Cosmotech), 0.3 part by weight of an epoxy curing agent (trade name: NA-30, Cosmotech) Mix. A solvent coater is applied to the mixture, and dried and coated with a thickness of 50 μm.
[실험예][Experimental Example]
1. 모듈러스 측정방법1. Modulus measurement method
너비 10mm, 두께 100μm, 길이 80mm의 모양으로 시편이 지그에 물려질 수 있도록 Dog bone모양의 시편을 제작하여 만들고, UTM을 사용하여 Young's modulus 를 측정하였다.A dog bone-shaped specimen with a width of 10 mm, a thickness of 100 μm, and a length of 80 mm was made so that the specimen could be bitten into a jig, and Young's modulus was measured using UTM.
Test speed : 300mm/minTest speed : 300mm/min
2. Haze 평가 2. Haze evaluation
빛이 투명한 재료 안을 통과할 때 재료의 종류에 따라서는 반사나 흡수 외에 그 재료의 고유 성질에 따라 광선이 확산되어 불투명한 흐림상 외관을 나타내는 것이 존재하는데, 이 현상을 헤이즈(Haze)라고 부르며, 이같이 투명한 것에 입사한 광선이 확산하는 정도를 헤이즈라 한다. 헤이즈가 작을 수록 광학적 성질이 우수한 물질에 해당한다.When light passes through a transparent material, depending on the type of material, in addition to reflection or absorption, the light is diffused according to the material's inherent properties, resulting in an opaque, cloudy appearance. This phenomenon is called haze. The degree to which light rays incident on such a transparent object are diffused is called haze. The smaller the haze, the better the optical properties.
헤이즈(Haze) = 확산투과율(Td) / 전광선투과율(Tt)Haze = diffuse transmittance (Td) / total light transmittance (Tt)
3. Yellow Index 평가3. Yellow Index Evaluation
Yellow Index 평가는 ASTM D1003 기준으로 Yellow Index 측정한다.Yellow Index is evaluated based on ASTM D1003.
4. 점착력 평가4. Adhesion evaluation
ASTM D3330 규격으로 평가를 진행하였다.Evaluation was conducted according to the ASTM D3330 standard.
5. 투과도 평가5. Permeability evaluation
ASTM D1003 23±2℃, 상대습도 50±5%의 표준 상태에서 측정하며 λ를 380nm~780nm의 범위 안에서 시험편을 5회 측정한 결과값을 기록하였다.ASTM D1003 Measured under the standard conditions of 23±2℃ and 50±5% relative humidity, and measured λ within the range of 380nm to 780nm 5 times and recorded the result.
투과도를 비롯한 Haze, Yellow Indexs는 색차계를 이용하여 측정하였다. Haze and yellow indexes including transmittance were measured using a color difference meter.
(Pa)modulus
(Pa)
7.00.E+07
7.00.E+07
(gf/inch)adhesiveness
(gf/inch)
상기 표 1의 실험결과를 살펴보면 반경화 접착층에 2차 경화를 진행하여 완경화 시킨 실시예 1 내지 3의 UV 조사 후의 모듈러스가, 비교예 1 내지 3의 모듈러스보다 100배 이상 높은 것으로 확인되었다. 또한 헤이즈(HAZE)도 실시예 1 내지 3이 비교예 1 내지 3에 비해 낮으며, 유리(Glass)와 스테인레스 강(SUS)에 대한 점착력도 실시예 1 내지 3이 비교예 1 내지 3에 비해 높은 것으로 확인되었다.Looking at the experimental results of Table 1, it was confirmed that the modulus after UV irradiation of Examples 1 to 3, in which the semi-cured adhesive layer was cured by secondary curing, was more than 100 times higher than the modulus of Comparative Examples 1 to 3. In addition, the haze (HAZE) of Examples 1 to 3 is lower than that of Comparative Examples 1 to 3, and the adhesion to glass and stainless steel (SUS) is also higher than that of Comparative Examples 1 to 3 in Examples 1 to 3. confirmed to be
이상 첨부된 도면을 참조하여 본 발명의 바람직한 실시예를 설명하였지만, 본 명세서에 기재된 실시예와 도면에 도시된 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 with reference to the accompanying drawings, the embodiments described in this specification and the configurations shown in the drawings are only the most preferred embodiments of the present invention and represent all the technical ideas of the present invention. Since it is not, it should be understood that there may be various equivalents and modifications that can replace them at the time of this application. 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 (5)
상기 우레탄 아크릴레이트 올리고머는 폴리프로필렌 글리콜((Polypropylene glycol) 75 내지 85 중량부와 이소포론 디이소시아네이트(Isophorone diisocyanate) 15 내지 25중량부를 중합시켜 폴리우레탄 예비중합체를 합성한 후, 2-히드록시에틸 아크릴레이트로와 캡핑(capping) 반응을 통해 제조된 것이고,
상기 우레탄 아크릴레이트 올리고머의 중량평균분자량이 4,000 g/mol 내지 200,000 g/mol이고,
상기 아크릴 모노머 혼합물의 모노머 혼합비는 이소보닐 메타아크릴레이트 65 내지 75 중량부, 벤질 메타아크릴레이트 15 내지 25 중량부 및 아크릴산 5 내지 15 중량부이고,
상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 광학적으로 투명한 접착시트.
A semi-cured adhesive layer prepared by performing primary curing on a composition containing 20 to 40 parts by weight of a urethane acrylate oligomer, 60 to 80 parts by weight of an acrylic monomer mixture, 0.05 to 0.2 parts by weight of a photoinitiator, and 0.5 to 2 parts by weight of a crosslinking agent, and ,
The urethane acrylate oligomer is synthesized by polymerizing 75 to 85 parts by weight of polypropylene glycol and 15 to 25 parts by weight of isophorone diisocyanate to synthesize a polyurethane prepolymer, and then 2-hydroxyethyl acrylic It is prepared through a rate and capping reaction,
The weight average molecular weight of the urethane acrylate oligomer is 4,000 g / mol to 200,000 g / mol,
The monomer mixing ratio of the acrylic monomer mixture is 65 to 75 parts by weight of isobornyl methacrylate, 15 to 25 parts by weight of benzyl methacrylate, and 5 to 15 parts by weight of acrylic acid,
An optically transparent adhesive sheet prepared by laminating the semi-cured adhesive layer to a sheet material and performing secondary curing.
상기 우레탄 아크릴레이트 올리고머는 폴리프로필렌 글리콜((Polypropylene glycol) 75 내지 85 중량부와 이소포론 디이소시아네이트(Isophorone diisocyanate) 15 내지 25중량부를 중합시켜 폴리우레탄 예비중합체를 합성한 후, 2-히드록시에틸 아크릴레이트로와 캡핑(capping) 반응을 통해 제조된 것이고,
상기 우레탄 아크릴레이트 올리고머의 중량평균분자량이 4,000 g/mol 내지 200,000 g/mol이고,
상기 아크릴 모노머 혼합물의 모노머 혼합비는 2-에틸헥실 (메타)아크릴레이트 3 내지 7 중량부, 이소보닐 메타아크릴레이트 55 내지 65 중량부, 벤질 메타아크릴레이트 7 내지 11 중량부, 테트라하이드로푸르푸릴 아크릴레이트 7 내지 11 중량부, 아크릴로일 모폴린 7 내지 11 중량부 및 아크릴산 7 내지 11 중량부이고,
상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 광학적으로 투명한 접착시트.
A semi-cured adhesive layer prepared by performing primary curing on a composition containing 20 to 40 parts by weight of a urethane acrylate oligomer, 60 to 80 parts by weight of an acrylic monomer mixture, 0.05 to 0.2 parts by weight of a photoinitiator, and 0.5 to 2 parts by weight of a crosslinking agent, and ,
The urethane acrylate oligomer is synthesized by polymerizing 75 to 85 parts by weight of polypropylene glycol and 15 to 25 parts by weight of isophorone diisocyanate to synthesize a polyurethane prepolymer, and then 2-hydroxyethyl acrylic It is prepared through a rate and capping reaction,
The weight average molecular weight of the urethane acrylate oligomer is 4,000 g / mol to 200,000 g / mol,
The monomer mixing ratio of the acrylic monomer mixture is 3 to 7 parts by weight of 2-ethylhexyl (meth)acrylate, 55 to 65 parts by weight of isobornyl methacrylate, 7 to 11 parts by weight of benzyl methacrylate, and tetrahydrofurfuryl acrylate. 7 to 11 parts by weight, 7 to 11 parts by weight of acryloyl morpholine and 7 to 11 parts by weight of acrylic acid,
An optically transparent adhesive sheet prepared by laminating the semi-cured adhesive layer to a sheet material and performing secondary curing.
상기 우레탄 아크릴레이트 올리고머는 폴리프로필렌 글리콜((Polypropylene glycol) 75 내지 85 중량부와 이소포론 디이소시아네이트(Isophorone diisocyanate) 15 내지 25중량부를 중합시켜 폴리우레탄 예비중합체를 합성한 후, 2-히드록시에틸 아크릴레이트로와 캡핑(capping) 반응을 통해 제조된 것이고,
상기 우레탄 아크릴레이트 올리고머의 중량평균분자량이 4,000 g/mol 내지 200,000 g/mol이고,
상기 아크릴 모노머 혼합물의 모노머 혼합비는 2-에틸헥실 아크릴레이트 15 내지 25 중량부, 이소보닐 메타아크릴레이트 50 내지 60 중량부, 벤질 메타아크릴레이트 10 내지 20 중량부 및 아크릴산 7 내지 11 중량부이고,
상기 반경화 접착층을 시트재에 합지하고 2차 경화를 진행하여 제조되는 광학적으로 투명한 접착시트.
40 to 60 parts by weight of a urethane acrylate oligomer, 40 to 60 parts by weight of an acrylic monomer mixture, 0.05 to 0.2 parts by weight of a photoinitiator, and 0.5 to 2 parts by weight of a crosslinking agent. A semi-cured adhesive layer prepared by performing primary curing, and ,
The urethane acrylate oligomer is synthesized by polymerizing 75 to 85 parts by weight of polypropylene glycol and 15 to 25 parts by weight of isophorone diisocyanate to synthesize a polyurethane prepolymer, and then 2-hydroxyethyl acrylic It is prepared through a rate and capping reaction,
The weight average molecular weight of the urethane acrylate oligomer is 4,000 g / mol to 200,000 g / mol,
The monomer mixing ratio of the acrylic monomer mixture is 15 to 25 parts by weight of 2-ethylhexyl acrylate, 50 to 60 parts by weight of isobornyl methacrylate, 10 to 20 parts by weight of benzyl methacrylate, and 7 to 11 parts by weight of acrylic acid,
An optically transparent adhesive sheet prepared by laminating the semi-cured adhesive layer to a sheet material and performing secondary curing.
상기 접착시트의 상기 2차 경화 후의 모듈러스가 106~1010 Pa인 것을 특징으로 하는 광학적으로 투명한 접착시트.
According to any one of claims 1 to 3,
The optically transparent adhesive sheet, characterized in that the modulus of the adhesive sheet after the secondary curing is 10 6 ~ 10 10 Pa.
상기 광개시제는 Irgacure 651이고,
상기 가교제는 1,6-헥산디올 디아크릴레이트인 것을 특징으로 하는 광학적으로 투명한 접착시트.
According to any one of claims 1 to 3,
The photoinitiator is Irgacure 651,
The optically transparent adhesive sheet, characterized in that the crosslinking agent is 1,6-hexanediol diacrylate.
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