KR20090090866A - Prism sheet of high refractive index and elasticity, the composition for producing the same and the method for its production - Google Patents
Prism sheet of high refractive index and elasticity, the composition for producing the same and the method for its production Download PDFInfo
- Publication number
- KR20090090866A KR20090090866A KR1020080016390A KR20080016390A KR20090090866A KR 20090090866 A KR20090090866 A KR 20090090866A KR 1020080016390 A KR1020080016390 A KR 1020080016390A KR 20080016390 A KR20080016390 A KR 20080016390A KR 20090090866 A KR20090090866 A KR 20090090866A
- Authority
- KR
- South Korea
- Prior art keywords
- meth
- acrylate
- group
- composition
- prism sheet
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- -1 acrylate compound Chemical class 0.000 claims abstract description 57
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 148
- 125000000524 functional group Chemical group 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 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 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 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 claims description 2
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 claims description 2
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 claims description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 claims description 2
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 claims description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- FBZUHOHZJHFVIY-UHFFFAOYSA-N 2,5-dimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1.CC1=CC=C(C)C(O)=C1 FBZUHOHZJHFVIY-UHFFFAOYSA-N 0.000 claims description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 claims description 2
- YBEBOWPOGZFUTF-UHFFFAOYSA-N 2-cyclohexyl-4-[(3-cyclohexyl-4-hydroxyphenyl)-(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C=C(C(O)=CC=1)C1CCCCC1)C1=CC=C(O)C(C2CCCCC2)=C1 YBEBOWPOGZFUTF-UHFFFAOYSA-N 0.000 claims description 2
- TUBNHXBTFDDYPI-UHFFFAOYSA-N 2-cyclohexyl-4-[(5-cyclohexyl-4-hydroxy-2-methylphenyl)-(4-hydroxyphenyl)methyl]-5-methylphenol Chemical compound CC1=CC(O)=C(C2CCCCC2)C=C1C(C=1C(=CC(O)=C(C2CCCCC2)C=1)C)C1=CC=C(O)C=C1 TUBNHXBTFDDYPI-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 claims description 2
- LYKRIFJRHXXXDZ-UHFFFAOYSA-N 4-(4-hydroxybutoxy)butan-1-ol Chemical compound OCCCCOCCCCO LYKRIFJRHXXXDZ-UHFFFAOYSA-N 0.000 claims description 2
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 claims description 2
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 claims description 2
- UHKSGTFIMPKOIT-UHFFFAOYSA-N C1(=C(C=CC=C1)C(C1=CC(=C(C=C1)O)C1CCCCC1)C1=CC(=C(C=C1)O)C1CCCCC1)C1=CC=CC=C1 Chemical compound C1(=C(C=CC=C1)C(C1=CC(=C(C=C1)O)C1CCCCC1)C1=CC(=C(C=C1)O)C1CCCCC1)C1=CC=CC=C1 UHKSGTFIMPKOIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002704 decyl 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])* 0.000 claims description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 229940117969 neopentyl glycol Drugs 0.000 claims description 2
- 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 claims description 2
- 125000002347 octyl 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])[H] 0.000 claims description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002948 undecyl 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])[H] 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 239000004816 latex Substances 0.000 claims 2
- 229920000126 latex Polymers 0.000 claims 2
- SLHMVWILIIYRFK-UHFFFAOYSA-N C1CC(CCC1C2=CC=CC=C2OO)(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O Chemical compound C1CC(CCC1C2=CC=CC=C2OO)(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O SLHMVWILIIYRFK-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 12
- 235000019589 hardness Nutrition 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
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Classifications
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
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- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- 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
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
- C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/04—Prisms
Abstract
Description
본 발명은 액정 표시 장치의 프리즘 시트 형성용 조성물에 관한 것이다. 본 발명은 더욱 상세하게는 고굴절률, 고탄성을 가지며, 기재와의 접착성이 뛰어난 프리즘 시트 형성용 조성물에 관한 것이다.The present invention relates to a composition for forming a prism sheet of a liquid crystal display device. More specifically, the present invention relates to a composition for forming a prism sheet having high refractive index and high elasticity and excellent adhesion to a substrate.
액정 표시 장치(liquid crystal display device, LCD device)는 수동형 장치여서 자체적인 발광이 현재로서는 불가능하므로 화면의 뒤쪽에서 빛을 조사하여 주어야만 한다. 이것 때문에 액정 표시 장치 화면의 뒤쪽에서 빛을 비추어 주는 백라이트 유닛(backlight unit)이 중요하며, 이 백라이트 유닛의 핵심 구성 부품 중의 하나가 바로 프리즘 시트(Prism Sheet)이다. 일반적인 백라이트 유닛의 구조에서 프리즘 시트는 밑면의 광 도광판(Light Guide Plate)과 확산판(Diffuser)을 통해 - 90°에서 + 90°사이의 입사각으로 입사하는 빛을 중심 방향으로 모아주는 역할을 한다.Liquid crystal display devices (LCD devices) are passive devices, so their own light emission is not possible at this time, so they must be illuminated from the back of the screen. For this reason, a backlight unit that emits light from the back of the LCD screen is important, and one of the key components of the backlight unit is a prism sheet. In the structure of a general backlight unit, the prism sheet collects light incident at an angle of incidence between −90 ° and + 90 ° through a light guide plate and a diffuser plate at the bottom thereof in a center direction.
프리즘 시트는 백라이트 유닛의 휘도를 향상시키는 데 있어서 매우 중요한 데, 그동안 백라이트 유닛의 휘도를 높이기 위한 다양한 시도가 있어왔다. 백라이트 유닛의 휘도를 높이기 위한 방법 중 하나로 프리즘 시트 재료의 굴절율을 높이는 방법이 있다. 굴절율이 높을수록 프리즘 시트의 성능이 향상되는데, 높은 굴절율을 가진 프리즘 시트가 LCD 백라이트의 효율을 증가시키는 데 사용되는 예는 일본 특허 출원공개 공보 제平5-127159호 등이 있다.The prism sheet is very important for improving the brightness of the backlight unit, and various attempts have been made to increase the brightness of the backlight unit. One method for increasing the brightness of the backlight unit is to increase the refractive index of the prism sheet material. The higher the refractive index, the better the performance of the prism sheet. Examples of the use of a prism sheet having a high refractive index to increase the efficiency of the LCD backlight include Japanese Patent Application Laid-open No. Hei 5-127159.
일반적으로 프리즘 시트에는 광경화형(주로 자외선) 아크릴산 에스테르 계열 물질이 많이 쓰인다. 아크릴산 에스테르 계열 물질은 대표적으로 아크릴레이트(acrylate)와 메트아크릴레이트(methacrylate) 에스테르가 있다. 아크릴레이트와 메트아크릴레이트는 수소와 메틸기의 차이 외에는 공통적으로 아크릴로일(acryloyl) 작용기 CH2=CHCOO-를 갖추고 있는, 유사성이 높은 물질들이므로, 본 명세서에서는 이하 이들을 아울러서 (메트)아크릴레이트로 통칭하겠다. 구체적인 (메트)아크릴레이트의 예로는 우레탄 (메트)아크릴레이트, 에폭시 (메트)아크릴레이트, 폴리에스터 (메트)아크릴레이트 등 하나 이상의 (메트)아크릴로일 작용기를 가지는 화합물이 많이 쓰이고 있다.Generally, photocurable (mainly ultraviolet) acrylic ester-based materials are commonly used in prism sheets. Acrylic acid ester-based materials are typically acrylate and methacrylate esters. Since acrylates and methacrylates are materials having high similarity in common with the acryloyl functional group CH 2 = CHCOO- except for the difference between hydrogen and methyl groups, in the present specification, these are referred to as (meth) acrylates in the following. Collectively. Examples of specific (meth) acrylates include compounds having one or more (meth) acryloyl functional groups, such as urethane (meth) acrylate, epoxy (meth) acrylate, and polyester (meth) acrylate.
이 중에서 우레탄 (메트)아크릴레이트 올리고머는 경화 후 기계적 강도가 높고, 각종 기재에 대한 부착성 및 가공성이 좋아 빛에 의하여 경화되는(광경화형) 형태의 각종 잉크, 코팅제 또는 접착제로 널리 사용되고 있다. 우레탄 (메트)아크릴레이트는 기본적으로 폴리올과 디이소시아네이트를 반응시켜 우레탄을 얻은 후, (메트)아크릴레이트를 부가 반응시켜 제조하는데, 업계에서는 용도에 따라 원하는 물성을 얻기 위하여 작용기를 더 도입하는 등 여러 가지 시도가 이루어지고 있다. 그러나 기존의 우레탄 (메트)아크릴레이트는 굴절률이 낮아 고휘도 기능성 광학 필름인 프리즘 시트와 같이 고굴절률을 요하는 제품에 적용하기에는 적합하지 않다.Among them, urethane (meth) acrylate oligomers are widely used as various inks, coating agents or adhesives in the form of high mechanical strength after curing and good adhesion and workability to various substrates (photocurable). Urethane (meth) acrylates are basically prepared by reacting polyols with diisocyanates to obtain urethanes, followed by addition reactions with (meth) acrylates. There are several attempts being made. However, existing urethane (meth) acrylates are not suitable for application to products requiring high refractive index such as prism sheet, which is a high brightness functional optical film due to low refractive index.
이 때문에 고굴절률과 내용제성을 가지는 광학 필름을 만들기 위해 에폭시(메트)아크릴레이트가 사용되어 왔다. 에폭시(메트)아크릴레이트는 일반적으로 양호한 내용제성과 고굴절률을 얻을 수는 있지만, 현재 요구되는 고휘도 광학 필름에 사용하기는 굴절률에 한계가 있다.For this reason, epoxy (meth) acrylates have been used to make optical films having high refractive index and solvent resistance. Epoxy (meth) acrylates generally have good solvent resistance and high refractive index, but have a limited refractive index for use in currently required high brightness optical films.
이러한 문제를 해결하기 위해 최근 업계에서는 (메트)아크릴레이트 화합물로서 불소를 제외한 할로겐 원자를 가지는 할로겐 함유 (메트)아크릴레이트나 황 원자를 가지는 황 함유 (메트)아크릴레이트를 사용하여 굴절률이 1.56 이상인 고굴절 아크릴레이트 조성액을 만들고 있다. 그러나 고굴절 할로겐 함유 (메트)아크릴레이트나 황 함유 (메트)아크릴레이트를 사용하여 프리즘 시트와 같은 고기능 광학 필름을 제조할 때에는 여러 가지 문제가 생길 수 있다. 예를 들어 최근 유럽에서는 유럽 연합의 전기·전자 분야 유해물질 사용제한 지침인 RoHS에 따라, 할로겐 화합물에 대한 규제가 시작되고 있으며, 황 함유 (메트)아크릴레이트의 경우 자외선 경화 속도가 느리고 황 특유의 냄새로 인해 제조 작업이 용이하지 않다.In order to solve this problem, the industry recently used a halogen-containing (meth) acrylate having a halogen atom except fluorine or a sulfur-containing (meth) acrylate having a sulfur atom as a (meth) acrylate compound, and has a high refractive index of 1.56 or more. We are making acrylate composition liquid. However, various problems may arise when producing high-performance optical films such as prism sheets using high refractive halogen-containing (meth) acrylates or sulfur-containing (meth) acrylates. In Europe, for example, the European Union's RoHS Directive on the Restriction of Hazardous Substances in the Electrical and Electronic Industry is beginning to regulate halogen compounds. Sulfur-containing (meth) acrylates have a slow UV curing rate and sulfur-specific properties. Odor is not easy to manufacture.
또한 플루오렌 유도체를 이용한 고굴절 (메트)아크릴레이트를 이용하여 프리즘 시트를 제작하고 있지만 플루오렌 유도체 자체의 가격 문제 때문에 현장에서 사용하기가 쉽지 않은 실정이다.In addition, although a prism sheet is manufactured using high refractive index (meth) acrylate using a fluorene derivative, it is not easy to use in the field due to the cost of the fluorene derivative itself.
한편 LCD 화면이 대형화함에 따라 그에 사용되는 프리즘 시트의 면적도 넓어 지고 있다. 대면적 프리즘 시트는 생산 과정이나 이동 중에 조그마한 흠집이 생길 수 있는 여지가 높아 불량률이 높아지기 쉽다. 이러한 문제를 해결하기 위해 이 분야에서는 프리즘 시트에 탄성력과 복원력을 부여하여, 표면에 이물질에 의한 긁힘(scratch)이나 충격이 가해지더라도 표면 패턴이 영구적으로 손상되지 않도록 새로운 연구를 시도하고 있다. 하지만 아직까지 충분한 복원력을 가지는, 고굴절, 고탄성 광경화형 수지의 개발에는 이르지 못한 실정이다.On the other hand, as the LCD screen becomes larger, the area of the prism sheet used for it is also increasing. Large-area prism sheets tend to have small scratches during the production process or during transportation, which leads to high defect rates. In order to solve this problem, this field is applying new elasticity and restoring force to the prism sheet, and attempting a new study so that the surface pattern is not permanently damaged even if the surface is scratched or impacted by foreign matter. However, the development of high refractive index, high elastic photocurable resins with sufficient restoring power has not yet been achieved.
본 발명은 상기와 같은 종래 기술의 문제점을 해결하기 위한 것으로, 굴절률이 높은 프리즘 시트 형성용 조성물을 제공하는 것이 목적이다. 아울러 본 발명에서는 탄성 복원력과 경도가 우수하여, 긁힘(scratch)에 대한 내성을 가지는 프리즘 시트 형성용 조성물을 제공하는 것이 또 다른 목적이다.The present invention is to solve the problems of the prior art as described above, and an object of the present invention is to provide a composition for forming a prism sheet having a high refractive index. In addition, it is another object of the present invention to provide a composition for forming a prism sheet having excellent elastic restoring force and hardness, and having a resistance to scratches.
상기 목적을 달성하기 위하여, 본 발명의 프리즘 시트 형성용 조성물의 구성은 (A) 특정 화학 구조를 가지는 우레탄 (메트)아크릴레이트, (B) 다작용기 가교제, (C) 단일 작용기 모노머 및 (D) 광개시제를 포함한다. In order to achieve the above object, the composition of the composition for forming a prism sheet of the present invention comprises (A) a urethane (meth) acrylate having a specific chemical structure, (B) a polyfunctional crosslinking agent, (C) a single functional monomer and (D) Photoinitiators.
본 발명의 프리즘 시트 형성용 조성물에서, (A) 성분인 특정 구조를 가지는 우레탄 (메트)아크릴레이트는 우레탄 작용기와 복수의 (메트)아크릴로일기를 가지는 분자이다. 상기 (A) 성분은 예를 들어, 페놀 분자와 이소시아네이트의 축합 반응에 의하여 얻을 수 있다. 본 발명에서 (A) 성분의 우레탄 (메트)아크릴레이트는 (메트)아크릴기의 수가 2개인 화학식 1의 분자, (메트)아크릴기의 수가 3개인 화학식 2의 분자 및 (메트)아크릴기의 수가 4개인 화학식 3의 분자로 이루어지는 군에서 선택되는 어느 하나의 물질 또는 이종 이상의 혼합물이다. In the composition for forming a prism sheet of the present invention, the urethane (meth) acrylate having a specific structure as the component (A) is a molecule having a urethane functional group and a plurality of (meth) acryloyl groups. The said (A) component can be obtained by condensation reaction of a phenol molecule and an isocyanate, for example. In the present invention, the urethane (meth) acrylate of component (A) is a molecule of formula (1) having a number of (meth) acryl groups, a molecule of formula (2) having a number of (meth) acryl groups, and a number of (meth) acryl groups At least one substance or a mixture of two or more selected from the group consisting of four molecules of formula (3).
성분 (B)인 다작용기 가교제는 중합·가교 반응을 일으킬 수 있는 작용기를 둘 이상 가지는 분자이다. 본 발명의 바람직한 다작용기 가교제로는 (메트)아크릴레이트 계열 화합물을 들 수 있다. 본 발명에서 성분 (B)의 다작용기 가교제는 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 20 내지 60 중량부의 비율로 포함되는 것이 바람직하다. The polyfunctional crosslinking agent as the component (B) is a molecule having two or more functional groups capable of causing a polymerization / crosslinking reaction. Preferred multifunctional crosslinking agents of the present invention include (meth) acrylate-based compounds. In the present invention, when the multifunctional crosslinking agent of the component (B) is 100 parts by weight of the total weight of the component (A), it is preferably included in a proportion of 20 to 60 parts by weight.
성분 (C)인 단일 작용기 모노머는 중합 가능한 비닐기를 하나만 가지는 화합물이다. 본 발명에서 단일 작용기 모노머는 반응성 희석을 위한 성분으로 쓰이는데, 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 50 내지 100 중량부의 비율로 포함되는 것이 바람직하다, The single functional group monomer as component (C) is a compound having only one polymerizable vinyl group. In the present invention, the single functional monomer is used as a component for reactive dilution, and when the total weight of component (A) is 100 parts by weight, it is preferably included in a ratio of 50 to 100 parts by weight,
본 발명에서 성분 (D)인 광개시제는 중합 반응의 개시제로서 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 5 내지 15 중량부의 비율로 포함되는 것이 바람직하다. When the photoinitiator which is component (D) in this invention makes 100 weight part of total weights of a component (A) as an initiator of a polymerization reaction, it is preferable to be contained in the ratio of 5-15 weight part with respect to it.
아울러 본 발명에서는 상기 프리즘 시트 형성용 조성물을 이용하여 제조한 프리즘 시트와 그 제조 방법을 제공한다. 본 발명에 따른 프리즘 시트는 투명 기재와 상기 투명 기재 위에 적층되고 복수의 단위 렌즈를 갖춘 프리즘 형상부로 이루어지는데, 이때 상기 프리즘 형상부는 제1항의 프리즘 시트 형성용 수지를 상기 복수의 단위 렌즈의 형상으로 성형하여 경화한 것이 특징이다.In addition, the present invention provides a prism sheet manufactured using the composition for forming a prism sheet and a method of manufacturing the same. The prism sheet according to the present invention comprises a transparent substrate and a prism-shaped portion laminated on the transparent substrate and having a plurality of unit lenses, wherein the prism-shaped portion comprises the resin for forming the prism sheet of claim 1 in the shape of the plurality of unit lenses. It is characterized by molding and curing.
본 발명의 프리즘 시트 제조 방법은 The prism sheet manufacturing method of this invention is
(1) 투명 기재 위에 본 발명의 프리즘 시트 형성용 조성물을 도포하는 단계(1) applying the composition for forming a prism sheet of the present invention on a transparent substrate
(2) 상기 조성물이 도포된 투명 기재를 롤러에 통과시키거나 다른 적절한 몰딩 공정을 수행함으로써 단위 렌즈를 형성하여 원하는 모양의 프리즘 형상부를 형성하는 단계(2) forming a unit lens by passing the transparent substrate coated with the composition through a roller or performing another suitable molding process to form a prism shape having a desired shape;
(3) 상기 프리즘 형상부를 경화시킬 수 있는 빛(주로 자외선)을 조사하여 상 기 프리즘 형상부를 경화시키는 단계의 세 단계를 포함하여 이루어진다.(3) irradiating light (mainly ultraviolet rays) capable of curing the prismatic features, and three steps of curing the prismatic features.
본 발명에 따른 조성물은 굴절률이 높기 때문에 액정 표시 패널용 프리즘 시트에 사용하면 화면의 휘도를 향상시킬 수 있다. 한편 본 발명에 따른 조성물은 탄성 복원력과 경도가 우수하여 외력에 의하여 프리즘 시트 표면이 긁히는 것을 방지할 수 있어 프리즘 시트의 표면에 충격이 가해져도, 표면 패턴의 손상을 최소화할 수 있다. 따라서 본 발명의 프리즘 시트 형성용 조성물을 이용한 프리즘 시트는 대화면 디스플레이용으로 특히 적합하다.Since the composition according to the present invention has a high refractive index, when used in a prism sheet for a liquid crystal display panel, the brightness of a screen may be improved. On the other hand, the composition according to the present invention is excellent in elastic restoring force and hardness can be prevented from scratching the surface of the prism sheet by the external force, even if the impact on the surface of the prism sheet, it is possible to minimize the damage to the surface pattern. Therefore, the prism sheet using the composition for forming a prism sheet of the present invention is particularly suitable for a large screen display.
이하 본 발명을 상세하게 설명한다. 본 발명의 프리즘 시트 형성용 조성물에서 (A) 성분인 특정 화학 구조의 우레탄 (메트)아크릴레이트는 우레탄 작용기와 복수의 아크릴로일기 CH=CH2COO-, 또는 복수의 메트아크릴로일기 CH2=CH(CH3)COO-를 가지는 분자이다. 이하 본 발명에서는 이 양 작용기를 통틀어 (메트)아크릴로일기로 약칭한다. 본 발명에서 (메트)아크릴레이트란 이러한 (메트)아크릴로일기를 가지는 에스테르 화합물을 일컫는다.Hereinafter, the present invention will be described in detail. In the composition for forming a prism sheet of the present invention, the urethane (meth) acrylate having a specific chemical structure as the component (A) is a urethane functional group and a plurality of acryloyl groups CH = CH 2 COO-, or a plurality of methacryloyl groups CH 2 = It is a molecule having CH (CH 3 ) COO-. Hereinafter, in the present invention, both functional groups are abbreviated as (meth) acryloyl groups. In the present invention, (meth) acrylate refers to an ester compound having such a (meth) acryloyl group.
본 발명에서 (A)의 우레탄 (메트)아크릴레이트는 아래 화학식 1 내지 3의 일반 구조를 가지는 분자들로 이루어지는 군에서 선택되는 하나의 물질 또는 이종 이상의 혼합물이다. 이 분자들은 예를 들어 복수의 페놀기를 가지는 페놀 화합물과 (메트)아크릴로일기를 가지는 이소시안산 에스테르(이소시아네이트)의 축합 반응으 로부터 얻을 수 있다.In the present invention, the urethane (meth) acrylate of (A) is one substance or a mixture of two or more selected from the group consisting of molecules having the general structure of Formulas 1 to 3 below. These molecules can be obtained, for example, from the condensation reaction of a phenol compound having a plurality of phenol groups and an isocyanic acid ester (isocyanate) having a (meth) acryloyl group.
상기 화학식 1 내지 3에서 Rj(j는 1~20의 자연수)는 수소 원자, 탄소 수가 1~10인 알킬기, 고리형 알킬기, 히드록시 알킬기, 치환된 또는 무치환 페닐기 및 히드록시기로 이루어지는 군에서 선택되는 작용기이며, 각 Rj끼리는 서로 같을 수도 다를 수도 있다. R'은 수소 원자, 탄소 수가 1~5인 알킬기, 고리형 알킬기 및 페닐 알킬기로 이루어지는 군에서 선택되는 작용기이다. X는 탄소수가 1~10인 사슬형 알킬렌기, 지방족 고리 치환 알킬렌기, 벤젠 고리가 치환된 알킬렌기 중에서 선택되는 작용기이다. Y는 수소 원자 또는 메틸기이다. In Formulas 1 to 3, R j (j is a natural number of 1 to 20) is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group, a hydroxy alkyl group, a substituted or unsubstituted phenyl group, and a hydroxy group It is a functional group, and each R j may be the same or different. R 'is a functional group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a cyclic alkyl group and a phenyl alkyl group. X is a functional group selected from a chain alkylene group having 1 to 10 carbon atoms, an aliphatic ring substituted alkylene group and an alkylene group substituted with a benzene ring. Y is a hydrogen atom or a methyl group.
성분 (A)인 우레탄 (메트)아크릴레이트는 수 평균 분자량이 1000 내지 그 이 상인 것이 바람직하다. 이 물질은 바람직하게는 굴절률이 1.55 이상인 비할로겐 고굴절 올리고머이다. A) 성분 올리고머의 분자량이 1000 이상일 경우 경화 후 컬(curl) 발생을 줄일 수 있기 때문에 더욱 바람직하며, (A) 성분 올리고머의 굴절률이 1.55 이상인 경우는 경화 후 백라이트 유닛의 목적인 고휘도를 발휘하는데 우수한 효과가 있다. 상기 (A) 성분에서 올리고머의 분자량이나 굴절률의 상한값은 원하는 물성과 경제성을 감안하여 필요한 수준에서 적절하게 정하면 되며, 특별한 값으로 제한하지 않아도 된다.It is preferable that the urethane (meth) acrylate which is a component (A) has a number average molecular weight 1000- or more. This material is preferably a non-halogen high refractive oligomer having a refractive index of at least 1.55. If the molecular weight of the component oligomer is 1000 or more, it is more preferable because it can reduce the occurrence of curl after curing, and if the refractive index of the component (A) oligomer is 1.55 or more, it is an excellent effect to achieve high brightness, which is the purpose of the backlight unit after curing. There is. The upper limit of the molecular weight and refractive index of the oligomer in the component (A) may be appropriately determined at a necessary level in consideration of desired physical properties and economical efficiency, and may not be limited to a special value.
성분 (A)의 우레탄 (메트)아크릴레이트는 이 분야에 알려진 적절한 종래 기술의 방법을 이용하여 합성할 수 있다. 한 가지 바람직한 합성 방법은 일반식을 화학식 4 내지 6으로 나타낼 수 있는 디, 트리, 테트라페놀 화합물과 일반식을 화학식 7로 나타낼 수 있는, 라디칼 중합 가능한 작용기를 함유한 이소시아네이트 화합물을 축합 반응시켜 얻는 것이다.The urethane (meth) acrylates of component (A) can be synthesized using any suitable prior art method known in the art. One preferred method of synthesis is obtained by condensation reaction of di, tri, tetraphenol compounds, which can be represented by the general formulas (4) to (6), and isocyanate compounds containing radically polymerizable functional groups, which can be represented by the general formula (7). .
상기 화학식 4 내지 6에서 Rj(j는 1~20의 자연수)는 수소 원자, 탄소 수가 1~10인 알킬기, 고리형 알킬기, 히드록시 알킬기, 치환된 또는 무치환 페닐기 및 히드록시 기로 이루어지는 군에서 선택되는 작용기이며, 각 Rj끼리는 서로 같을 수도 다를 수도 있다. R'은 수소 원자, 탄소 수가 1~5인 알킬기, 고리형 알킬기 및 페닐 알킬기로 이루어지는 군에서 선택되는 작용기이다. In Formulas 4 to 6, R j (j is a natural number of 1 to 20) in the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group, a hydroxy alkyl group, a substituted or unsubstituted phenyl group and a hydroxy group It is a functional group to be selected, and each R j may be the same or different. R 'is a functional group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a cyclic alkyl group and a phenyl alkyl group.
상기 화학식 4 내지 6의 일반식으로 나타낼 수 있는 페놀로서 본 발명의 (A) 성분을 합성하는데 적절한 물질의 예를 일부 들자면 다음과 같다: 5,5'-(메틸에틸리덴)비스[1,1'-(바이페닐)-2-올], 5,5′-(1,1′-사이클로헥실리덴)[1,1′-(바이페닐)-2-올], 4,4′-(디페닐메틸렌)비스페놀, [1,1′-바이사이클로헥센-3,3′-일]-4,4′-비스[2,5-디메틸페놀], 5,5′-(1-페닐에틸리덴)비스[(1,1′-바이페닐)-2-올], 4,4′-[-(1,1-바이페닐일)메틸렌]비스[2-사이클로헥실페놀], 4,4′-[(4-하이드록시페닐)메틸렌]비스[2-사이클로헥실-5-메틸페놀], 4,4′-[4-(하이드록시페닐)사이클로헥실리덴]비스페놀, 4,4′-[(2-하이드록시페닐)메틸렌]비스[2-사이클로헥실페놀], 4,4′,4″,4′″-(1,4-페닐렌디메틸리덴)테트라키스페놀, 4, 4', 4″,4'''-테트라키스(1,1-바이사이클로헥실리덴)페놀 등.Some examples of materials suitable for synthesizing component (A) of the present invention as phenols represented by the general formulas of Chemical Formulas 4 to 6 are as follows: 5,5 '-(methylethylidene) bis [1, 1 '-(biphenyl) -2-ol], 5,5'-(1,1'-cyclohexylidene) [1,1 '-(biphenyl) -2-ol], 4,4'- (Diphenylmethylene) bisphenol, [1,1'-bicyclohexene-3,3'-yl] -4,4'-bis [2,5-dimethylphenol], 5,5 '-(1-phenyl Thilidene) bis [(1,1'-biphenyl) -2-ol], 4,4 '-[-(1,1-biphenylyl) methylene] bis [2-cyclohexylphenol], 4,4 ′-[(4-hydroxyphenyl) methylene] bis [2-cyclohexyl-5-methylphenol], 4,4 ′-[4- (hydroxyphenyl) cyclohexylidene] bisphenol, 4,4′- [(2-hydroxyphenyl) methylene] bis [2-cyclohexylphenol], 4,4 ′, 4 ″, 4 ′ ″-(1,4-phenylenedimethylidene) tetrakisphenol, 4, 4 ′, 4 ″, 4 ′ ″-tetrakis (1,1-bicyclohexylidene) phenol and the like.
이들 적절한 페놀 화합물로서 시판되는 제품의 예를 들면 다음과 같다: BisOPP-A, BisOPP-Z, BisP-DP, BisOPP-AP, BisOCHP-BP, BisP-2HBP, TrisP-3M6C, TrisOCHP-S, TekP-TPA, TekP-4HBP(일본 혼슈화학 제조).Examples of commercially available products as these suitable phenolic compounds are as follows: BisOPP-A, BisOPP-Z, BisP-DP, BisOPP-AP, BisOCHP-BP, BisP-2HBP, TrisP-3M6C, TrisOCHP-S, TekP- TPA, TekP-4HBP (manufactured by Honshu Chemical Japan).
한편 상기 페놀 화합물의 히드록시기와 축합하여 우레탄 결합을 형성할 수 있고, 라디칼 중합성 작용기를 함유하는 이소시아네이트 화합물은 특별히 한정되지 않는다. 적절한 예를 하나 들자면 일반식이 하기 화학식 7로 나타나는 (메트)아크 릴로일옥시알킬이소시아네이트가 바람직하다.On the other hand, a urethane bond can be formed by condensation with the hydroxyl group of the said phenol compound, and the isocyanate compound containing a radically polymerizable functional group is not specifically limited. One suitable example is preferably a (meth) acryloyloxyalkyl isocyanate represented by the general formula (7) below.
상기 화학식 7에서 X는 탄소수가 1~10인 사슬형 알킬렌기, 지방족 고리 치환 알킬렌기, 벤젠 고리가 치환된 알킬렌기 중에서 선택되는 작용기이고, Y 는 수소 또는 메틸을 나타낸다. 또한, 화학식 7의 (메트)아크릴로일옥시알킬이소시아네이트 중에서도, (메트)아크릴로일기가 탄소수 2∼6의 알킬렌기를 개재하여(즉 X가 탄소 수 2~6인 알킬렌기) 이소시안산기와 결합한 것이 바람직하다. 구체적으로는 2-아크릴로일옥시에틸이소시아네이트, 2-메트아크릴로일에틸이소시아네이트 등을 들 수 있다. 또한, 상기 2-메트아크릴로일에틸이소시아네이트의 시판품으로서는 예를 들어, 카렌즈 MOI (일본 쇼와덴코社 제조)등이 있다.In Formula 7, X is a functional group selected from a chain alkylene group having 1 to 10 carbon atoms, an aliphatic ring substituted alkylene group, and an alkylene group substituted with a benzene ring, and Y represents hydrogen or methyl. In addition, in the (meth) acryloyloxyalkyl isocyanate represented by the general formula (7), the (meth) acryloyl group is an isocyanate group via an alkylene group having 2 to 6 carbon atoms (that is, an alkylene group having X having 2 to 6 carbon atoms). It is preferable to combine. 2-acryloyloxyethyl isocyanate, 2-methacryloyl ethyl isocyanate, etc. are mentioned specifically ,. Moreover, as a commercial item of the said 2-methacryloyl ethyl isocyanate, Kalenz MOI (made by Showa Denko Japan) etc. is mentioned, for example.
본 발명의 프리즘 시트 형성용 조성물에서 성분(A)의 우레탄 (메트)아크릴레이트는 전체 조성물에서 30 중량% 내지 70 중량%를 차지하는 것이 바람직하다. (A) 성분의 함량이 상기 범위 내에 있는 경우에는 프리즘 시트의 굴절률, 탄성 회복율, 접착력을 우수하게 확보할 수 있으며, 점도를 적절한 수준으로 유지할 수 있어 공정성 개선 효과가 있다.In the composition for forming a prism sheet of the present invention, the urethane (meth) acrylate of component (A) preferably accounts for 30% to 70% by weight of the total composition. When the content of the component (A) is within the above range, the refractive index, elastic recovery rate, and adhesive strength of the prism sheet can be excellently secured, and the viscosity can be maintained at an appropriate level, thereby improving processability.
다음은 화학식 1 내지 3의 일반식으로 나타낸 우레탄 (메트)아크릴레이트를 화학식 7의 이소시아네이트 분자와 화학식 4 내지 6의 페놀 분자로부터 합성하는 반응을 예시한다.The following illustrates the reaction of synthesizing urethane (meth) acrylates represented by the general formulas of the formulas (1) to (3) from the isocyanate molecules of formula (7) and the phenol molecules of formulas (4) to (6).
<우레탄 (메트)아크릴레이트 분자의 제조><Production of Urethane (meth) acrylate Molecules>
2개의 하이드록시기를 가지는 상기의 화학식 4의 디페놀 분자 1 당량에 대하여 (메트)아크릴기와 이소시안산 작용기 -NCO를 동시에 가지는 화학식 7의 분자를 2 당량 반응시켜 화학식 1의 구조를 가지는 우레탄 (메트)아크릴레이트를 합성할 수 있다. 전형적인 반응 조건에서 반응 촉매는 디라우릴산디부틸주석(dibutyltin dilaurylate)을 사용하게 되며, 반응 시간은 50℃에서 5시간이다. 여기서 Rj(j는 1~8의 자연수)는 수소 원자, 탄소 수가 1~10인 알킬기, 고리형 알킬기, 히드록시 알킬기, 치환된 또는 무치환 페닐기 및 히드록시기로 이루어지는 군에서 선택되는 작용기이며, 각 Rj끼리는 서로 같을 수도 다를 수도 있다. R'은 수소 원자, 탄소 수가 1~5인 알킬기, 고리형 알킬기 및 페닐 알킬기로 이루어지는 군에서 선택되는 작용기이다. X는 탄소수가 1~10 인 알킬기, 고리형 알킬기, 벤젠기 및 페닐 알킬 기 중에서 선택되는 작용기이다. Y는 수소 원자 또는 메틸기이다.A urethane having a structure of Formula 1 by reacting 2 equivalents of a molecule of Formula 7 having a (meth) acryl group and an isocyanate functional group -NCO with respect to 1 equivalent of the diphenol molecule of Formula 4 having two hydroxyl groups ) Acrylate can be synthesized. Under typical reaction conditions, the reaction catalyst uses dibutyltin dilaurylate, and the reaction time is 5 hours at 50 ° C. R j (j is a natural number of 1 to 8) is a functional group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group, a hydroxy alkyl group, a substituted or unsubstituted phenyl group and a hydroxy group, each R j may be the same or different. R 'is a functional group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a cyclic alkyl group and a phenyl alkyl group. X is a functional group selected from an alkyl group having 1 to 10 carbon atoms, a cyclic alkyl group, a benzene group and a phenyl alkyl group. Y is a hydrogen atom or a methyl group.
3개의 히드록시기를 가지는 상기 화학식 4의 분자 1 당량에 (메트)아크릴기와 -NCO기를 동시에 가지는 화학식 7의 분자 3 당량을 반응시켜 화학식 2의 구조를 가지는 우레탄 (메트)아크릴레이트를 합성할 수 있다. 촉매 등의 반응 조건과 Rj(j는 1~12의 자연수), R', X, Y의 의미는 화학식 1 분자의 경우와 같다.A urethane (meth) acrylate having a structure of Formula 2 may be synthesized by reacting 3 equivalents of a molecule of Formula 7 having a (meth) acryl group and a -NCO group simultaneously with 1 equivalent of the molecule of Formula 4 having three hydroxyl groups. Reaction conditions such as a catalyst, and R j (j is a natural number of 1 to 12), the meaning of R ', X, Y are the same as in the case of the molecule of formula (1).
4개의 히드록시기를 가지는 상기 화학식 4의 테트라페놀 분자 1 당량에 대하여 (메트)아크릴기와 -NCO기를 동시에 가지는 화학식 7의 분자 4 당량을 반응시켜 화학식 3의 구조를 가지는 우레탄 (메트)아크릴레이트를 합성할 수 있다. 촉매 등의 반응 조건과 Rj(j는 1~20의 자연수), R', X, Y의 의미는 화학식 1 분자의 경우와 같다.A urethane (meth) acrylate having the structure of Formula 3 may be synthesized by reacting 4 equivalents of the tetraphenol molecule of Formula 4 with 4 hydroxyl groups with 4 equivalents of the molecule of Formula 7 having the (meth) acryl group and the -NCO group. Can be. Reaction conditions such as a catalyst, and R j (j is a natural number of 1 to 20), the meaning of R ', X, Y are the same as in the case of the formula (1) molecule.
본 발명에서 성분 (B)의 다작용기 가교제는 중합·가교 반응을 일으킬 수 있는 작용기가 하나 이상인 화합물을 일컫는다. 상기 성분 (B)로는 광학적 특성과 성분 (A)와의 상용성 측면에서 (메트)아크릴레이트가 바람직하다. 다작용기 가교제가 (메트)아크릴레이트인 경우, 상기 (A) 성분의 (메트)아크릴레이트는 제외된 다. 성분 (B)의 다작용기 가교제는 자외선 경화에 의하여 가교를 형성하기 때문에 경화된 조성물의 표면 경도를 증가시키며, 기재와의 접착력을 증가시키는 역할을 한다.In the present invention, the multifunctional crosslinking agent of component (B) refers to a compound having at least one functional group capable of causing a polymerization / crosslinking reaction. As said component (B), (meth) acrylate is preferable at the point of compatibility with an optical characteristic and a component (A). When the polyfunctional crosslinking agent is (meth) acrylate, the (meth) acrylate of the above-mentioned (A) component is excluded. The multifunctional crosslinking agent of component (B) increases the surface hardness of the cured composition because it forms crosslinks by ultraviolet curing, and serves to increase the adhesion to the substrate.
(B) 성분인 다작용기 가교제 화합물의 예를 일부 들면 다음과 같다: 트리메틸올프로판 트리(메트)아크릴레이트, 펜타에리트리톨 트리(메트)아크릴레이트, 에틸렌글리콜 디(메트)아크릴레이트, 테트라에틸렌글리콜 디(메트)아크릴레이트, 폴리에틸렌글리콜 디(메트)아크릴레이트, 1,4-부탄디올 디(메트)아크릴레이트, 1,6-헥산디올 디(메트)아크릴레이트, 네오펜틸글리콜 디(메트)아크릴레이트, 트리메틸올프로판트리옥시에틸 (메트)아크릴레이트, 트리스(2-히드록시에틸)이소시아누레이트 트리(메트)아크릴레이트, 트리스(2-히드록시에틸)이소시아누레이트 디(메트)아크릴레이트, 비스(히드록시메틸)트리시클로데칸디(메트)아크릴레이트, 디펜타에리트리톨 헥사(메트)아크릴레이트, 비스페놀 A에 대하여 폴리에틸렌 산화물 또는 폴리프로필렌 산화물을 첨가시켜 생성되는 디올의 디(메트)아크릴레이트, 수소화 비스페놀 A에 대하여 폴리에틸렌 산화물 또는 폴리프로필렌 산화물을 첨가시켜 생성되는 디올의 디(메트)아크릴레이트 및 디글리시딜 에테르와 비스페놀 A의 반응 생성물에 (메트)아크릴산을 첨가함으로써 제조된 에폭시(메트)아크릴레이트.Some examples of the multifunctional crosslinking compound (B) are as follows: trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethylene glycol Di (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentylglycol di (meth) acrylate , Trimethylolpropanetrioxyethyl (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate Polyethylene oxide or polypropylene oxide to bis (hydroxymethyl) tricyclodecanedi (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and bisphenol A To the reaction product of di (meth) acrylate and diglycidyl ether of diol and bisphenol A produced by adding polyethylene oxide or polypropylene oxide to di (meth) acrylate of hydrogen diol, hydrogenated bisphenol A Epoxy (meth) acrylates prepared by adding meth) acrylic acid.
시판되는 다작용기 가교제의 구체적인 예로는 Yupimer UV SA1002, SA2007(일본 미쓰비시 화학 제품), Viscoat #195, #230, #215, #260, #335HP, #295, #300, #360, #700, GPT, 3PA(일본 오사카 유기화학 제품), Light Acrylate 4EG-A, 9EG-A, NP-A, DCP-A, BP-4EA, BP-4PA, TMP-A,PE-3A, PE-4A, DPE-6A(일본 교에이화학 제조 ), KAYARAD PET-30, TMPTA, R-604, DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-120, HX-620, D-310, D-330(일본 니뽄가야꾸社 제조), AronixM-208, M-210, M-215, M-220, M-240, M-305, M-309, M-310, M-315, M-325, M-400(일본 토아고세이社 제조), Ripoxy VR-77, VR-60, VR-90(일본 쇼와하이폴리머社 제조)를 들 수 있다.Specific examples of commercially available multifunctional crosslinkers include Yupimer UV SA1002, SA2007 (Mitsubishi Chemical, Japan), Viscoat # 195, # 230, # 215, # 260, # 335HP, # 295, # 300, # 360, # 700, GPT , 3PA (Osaka Organic Chemicals, Japan), Light Acrylate 4EG-A, 9EG-A, NP-A, DCP-A, BP-4EA, BP-4PA, TMP-A, PE-3A, PE-4A, DPE- 6A (Japan Kyoi Chemical Co., Ltd.), KAYARAD PET-30, TMPTA, R-604, DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-120, HX-620, D-310, D-330 Japan Nippon Kayaku Co., Ltd.), AronixM-208, M-210, M-215, M-220, M-240, M-305, M-309, M-310, M-315, M-325, M- 400 (manufactured by Toagosei Co., Ltd.), Ripoxy VR-77, VR-60, and VR-90 (manufactured by Showa High Polymer Co., Ltd.).
성분 (B)의 다작용기 가교제는 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 20 내지 60 중량부의 비율로 포함되는 것이 바람직하다. (B) 성분 다작용기 가교제의 함량이 상기 범위 내에 있을 때는 조성물의 경도와 접착력이 우수한 범위 내에 있게 되며, 과잉 경화로 인한 컬(curl)이나 심지어 균열(crack) 현상이 일어나는 것을 방지할 수 있다.When the multifunctional crosslinking agent of component (B) makes 100 weight part of total weights of a component (A), it is preferable to be contained in the ratio of 20-60 weight part with respect to it. When the content of the component (B) multifunctional crosslinking agent is in the above range, the hardness and adhesion of the composition are in an excellent range, and curling or even cracking due to excessive curing can be prevented.
본 발명에서 성분 (C)로 나타내는 단일 작용기 모노머는 이중결합을 가지는 비닐기를 하나밖에 가지고 있지 않은 분자를 일컫는다. 단일 작용기 모노머는 비닐기가 하나밖에 없기 때문에 중합·가교시 반응성 희석제로 작용한다. 단일 작용기 모노머는 조성물의 점도를 감소시킴으로써 기타 모노머/올리고머를 용해하여 구조물로 가교하는데 도움이 된다. In the present invention, the single functional monomer represented by component (C) refers to a molecule having only one vinyl group having a double bond. Since a single functional monomer has only one vinyl group, it functions as a reactive diluent during polymerization and crosslinking. Single functional monomers help to dissolve other monomers / oligomers and crosslink into the structure by reducing the viscosity of the composition.
단일 작용기 모노머의 예로는 비닐 모노머를 들 수 있는데, 그 일부 예로는 N-비닐피롤리돈, N-비닐카프로락탐, 비닐이미다졸, 및 비닐피리딘, 이소보르닐 (메트)아크릴레이트, 보르닐 (메트)아크릴레이트, 트리사이클로데카닐 (메트)아크릴레이트, 디시클로펜타닐 (메트)아크릴레이트, 디사이클로펜테닐 (메트)아크릴레이트, 사이클로헥실 (메트)아크릴레이트, 벤질 (메트)아크릴레이트, 4-부틸시클로헥실 (메트)아크릴레이트, 아크릴로일모르폴린, 2-히드록시에틸 (메트)아크릴레이트, 2- 히드록시프로필 (메트)아크릴레이트, 2-히드록시부틸 (메트)아크릴레이트, 메틸 (메트)아크릴레이트, 에틸 (메트)아크릴레이트, 프로필 (메트)아크릴레이트, 이소프로필 (메트)아크릴레이트, 부틸 (메트)아크릴레이트, 아밀 (메트)아크릴레이트, 이소부틸 (메트)아크릴레이트, t-부틸 (메트)아크릴레이트, 펜틸 (메트)아크릴레이트, 이소아밀 (메트)아크릴레이트, 헥실(메트)아크릴레이트, 헵틸 (메트)아크릴레이트, 옥틸 (메트)아크릴레이트, 이소옥틸 (메트)아크릴레이트, 2-에틸헥실(메트)아크릴레이트, 노닐 (메트)아크릴레이트, 데실 (메트)아크릴레이트, 이소데실 (메트)아크릴레이트, 운데실 (메트)아크릴레이트, 도데실 (메트)아크릴레이트, 라우릴 (메트)아크릴레이트, 스테아릴 (메트)아크릴레이트, 이소스테아릴 (메트)아크릴레이트, 테트라히드로푸르푸릴 (메트)아크릴레이트, 부톡시에틸 (메트)아크릴레이트, 에톡시디에틸렌글리콜 (메트)아크릴레이트, 폴리에틸렌 글리콜 모노 (메트)아크릴레이트, 폴리프로필렌 글리콜 모노 (메트)아크릴레이트, 메톡시에틸렌 글리콜 (메트)아크릴레이트, 에톡시에틸 (메트)아크릴레이트, 메톡시폴리에틸렌 글리콜 (메트)아크릴레이트, 메톡시폴리프로필렌글리콜 (메트)아크릴레이트, 디아세톤 (메트)아크릴아미드, 이소부톡시메틸 (메트)아크릴아미드, N,N-디메틸(메트)아크릴아미드, t-옥틸 (메트)아크릴아미드, 디메틸아미노에틸 (메트)아크릴레이트,디에틸아미노에틸 (메트)아크릴레이트, 7-아미노-3,7-디메틸옥틸 (메트)아크릴레이트, N,N-디에틸(메트)아크릴아미드, N,N-디메틸아미노프로필 (메트)아크릴아미드, 히드록시부틸 에테르, 라우릴비닐 에테르, 세틸비닐 에테르, 2-에틸헥실비닐 에테르 등이 있다.Examples of single functional monomers include vinyl monomers, some examples of which are N -vinylpyrrolidone, N -vinylcaprolactam, vinylimidazole, and vinylpyridine, isobornyl (meth) acrylate, bornyl (Meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, 4-butylcyclohexyl (meth) acrylate, acryloyl morpholine, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, isobutyl (meth) acrylate Nitrate, t -butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl ( Meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) Acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxydiethylene Glycol (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, methoxyethylene glycol (meth) acrylate, ethoxyethyl (meth) acrylic Sites, methoxy polyethylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate, diacetone (meth) acrylamide, isobutoxy methyl (meth) acrylamide, N, N - dimethyl (meth) acrylamide , t -octyl (meth) acrylamide, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 7-amino-3,7-dimethyloctyl (meth) acrylate, N, N -di Ethyl (meth) acrylamide, N, N -dimethylaminopropyl (meth) acrylamide, hydroxybutyl ether, laurylvinyl ether, cetylvinyl ether, 2-ethylhexylvinyl ether and the like.
시판되는 단일 작용기 모노머의 구체적인 예로는 Aronix M111, M113, M117(일본 토아고세이社 제조), LA, IBXA, Viscoat #190, #2000(일본 오사카 유기화학 제조), Light Acrylate EC-A, POA, NP-4EA, NP-8EA, HOA-MPL(일본 교에이 화학 제조), KAYARAD TC110S, R629, R644(일본 니뽄가야꾸社 제조), FA-511A, 512A, 513A(일본 히타치화성 제조), VP(독일 바스프社 제조), ACMO, DMAA, DMAPAA(일본 코진社 제조)를 들 수 있다.Specific examples of commercially available single functional monomers include Aronix M111, M113, and M117 (manufactured by Toagosei Co., Japan), LA, IBXA, Viscoat # 190, # 2000 (manufactured by Osaka Organic Chemicals, Japan), Light Acrylate EC-A, POA, NP -4EA, NP-8EA, HOA-MPL (manufactured by Kyoi Chemical, Japan), KAYARAD TC110S, R629, R644 (manufactured by Nippon Kayaku Co., Ltd.), FA-511A, 512A, 513A (manufactured by Hitachi Kasei, Japan), VP (Germany BASF Co., Ltd.), ACMO, DMAA, DMAPAA (made by Kojin Co., Ltd., Japan).
성분(C)의 단일 작용기 모노머는 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 50 내지 100 중량부의 비율로 포함되는 것이 바람직하다. (C)의 단일 작용기 모노머의 함량이 상기 범위 내일 때는 조성물의 점도·접착력과 굴절률이 적절하게 절충될 수 있어, 작업성이 양호해지며 경화성도 양호한 범위 내에서 조절할 수 있다. 또한 제조된 프리즘 시트의 굴절률을 높은 수준으로 유지하는데 효과가 있다.The single functional monomer of component (C) is preferably included in a proportion of 50 to 100 parts by weight, based on 100 parts by weight of the total weight of component (A). When the content of the single functional monomer of (C) is within the above range, the viscosity, adhesive force and refractive index of the composition can be appropriately compromised, so that workability is good and the curability can be adjusted within a good range. It is also effective in maintaining the refractive index of the produced prism sheet at a high level.
본 발명에서 성분 (D)의 광개시제는 빛을 조사하여 조성물을 경화하기 위해 필요하며, 감광제가 선택적으로 포함할 수 있다. 광개시제로서, 조사시에 분해하고, 라디칼을 발생시켜 중합을 개시하는 화합물이 사용될 수 있다. In the present invention, the photoinitiator of component (D) is required to cure the composition by irradiating light, and a photosensitive agent may optionally be included. As the photoinitiator, a compound which decomposes upon irradiation and generates radicals to initiate polymerization can be used.
상기 (D) 성분의 일부 예로는 아세토페논, 아세토페논 벤질 케탈, 1-히드록시시클로헥실 페닐 케톤, 2,2-디메톡시-2-페닐아세토페논, 크산톤, 플루오레논, 벤즈알데히드, 플루오렌, 안트라퀴논, 트리페닐아민, 카르바졸, 3-메틸아세토페논, 4-클로로벤조페논, 4,4'-디메톡시벤조페논, 4,4'-디아미노벤조페논, 미클러 케톤, 벤조인 프로필 에테르, 벤조인 에틸 에테르, 벤질 디메틸 케탈, 1-(4-이소프로필페 닐)-2-히드록시-2-메틸프로판-1-온, 2-히드록시-2-메틸-1-페닐프로판-1-온, 티옥산톤, 디에틸티옥산톤, 2-이소프로필티옥산톤, 2-클로로티옥산톤, 2-메틸-1-[4-(메틸티오)페닐]-2-모르폴리노-프로판-1-온, 2,4,6-트리메틸벤조일 디페닐포스핀 산화물 및 비스-(2,6-디메톡시벤조일)-2,4,4-트리메틸펜틸포스핀 산화물이 있다.Some examples of the component (D) include acetophenone, acetophenone benzyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, xanthone, fluorenone, benzaldehyde, fluorene, Anthraquinone, triphenylamine, carbazole, 3-methylacetophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, mychler ketone, benzoin propyl ether , Benzoin ethyl ether, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 2-hydroxy-2-methyl-1-phenylpropane-1 -One, thioxanthone, diethyl thioxanthone, 2-isopropyl thioxanthone, 2-chlorothioxanthone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino- Propan-1-one, 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis- (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide.
시판되는 광개시제의 구체적인 예로는 Irgacure 184, 369, 651, 127, 819, 907, 784, 2959, 754, Darocur 1173(스위스 시바스페셜티케미칼 제조), Lucirin TPO, LR8893, LR8970(독일 바스프社 제조), Ubecryl P36(벨기에 유씨비社 제조)가 있다.Specific examples of commercially available photoinitiators include Irgacure 184, 369, 651, 127, 819, 907, 784, 2959, 754, Darocur 1173 (manufactured by Shiva Specialty Chemical, Switzerland), Lucirin TPO, LR8893, LR8970 (manufactured by BASF, Germany), Ubecryl P36 (manufactured by WBC) of Belgium.
성분 (D)의 광개시제는 성분 (A)의 총 중량을 100 중량부로 했을 때, 그에 대하여 5 내지 15 중량부의 비율로 포함되는 것이 바람직하다. 더욱 바람직하게는 … 내지 … 중량부 수준으로 존재한다. (D) 성분인 광개시제 함량이 상기 범위내에 있으면 충분한 광경화가 이루어질 수 있고, 경화 반응에 필요한 양만큼만 광개시제의 표면 석출 현상 등을 피할 수 있어서 프리즘 시트의 표면을 깨끗하게 유지할 수 있고, 경제적이다.The photoinitiator of component (D) is preferably included in the ratio of 5-15 weight part with respect to 100 weight part of total weight of component (A). More preferably. To… Present in parts by weight. When the content of the photoinitiator as the component (D) is within the above range, sufficient photocuring can be achieved, and the surface precipitation phenomenon of the photoinitiator can be avoided only by the amount necessary for the curing reaction, so that the surface of the prism sheet can be kept clean and economical.
상기 성분들에 더해, 경화가능한 조성물 및 경화된 조성물에 바람직한 특성을 제공하기 위해 상기 조성물을 개질하는 여러 가지 임의의 첨가제를 추가로 포함할 수 있다. 사용할 수 있는 첨가제의 예로는 이형제(離型劑), 커플링제, 충전제, 증량제, 대전 방지제, 현탁제, 윤활제, 습윤제, 계면활성제, 자외선 안정화제 등을 들 수 있다. 이들 물질의 양은 원하는 특성을 이루기 위하여 필요한 만큼 첨가할 수 있으나, 일반적으로 그 비율은 이들 첨가제를 제외한 전체 조성물 100 중량부에 대하여 0.1 내지 10 중량부로 포함하는 것이 바람직하다. 더욱 바람직하게는 0.5 내지 5 중량부 수준으로 존재한다.In addition to the above components, it may further include various optional additives that modify the composition to provide desirable properties for the curable composition and the cured composition. Examples of the additive that can be used include a release agent, a coupling agent, a filler, an extender, an antistatic agent, a suspending agent, a lubricant, a humectant, a surfactant, an ultraviolet stabilizer, and the like. The amount of these materials can be added as necessary to achieve the desired properties, but in general, the ratio is preferably included in 0.1 to 10 parts by weight based on 100 parts by weight of the total composition excluding these additives. More preferably present at a level of 0.5 to 5 parts by weight.
본 발명의 프리즘 시트 형성용 조성물은 특별한 제조 방법에 구애됨이 없이, 일반적인 광경화 방식의 몰딩에 의하여 프리즘 시트로 가공될 수 있다. 프리즘 시트의 구조와 프리즘 시트의 제조 방법에 대해서는 종래 기술, 예를 들어 일본 특허공개공보 평5-169015호 등에 개시된 방법을 적절히 채택하면 되므로 여기서 자세히 설명하지 않으나, 기본적인 사항은 다음과 같다. 프리즘 시트는 투명한 재질의 기재 위에 광경화성 수지로 이루어진 프리즘 형상부가 적층된 구조이다. 프리즘 형상부는 빛을 특정 방향으로 출광시키기 위한 다수의 단위 렌즈가 1차원 또는 2차원 방향으로 소정의 간격(pitch)로 배열된 형상을 하고 있는데, 단위 렌즈의 가장 흔한 형태는 삼각 기둥 모양이지만 특별한 제한은 없다. The composition for forming a prism sheet of the present invention can be processed into a prism sheet by molding of a general photocuring method, without being bound to a particular manufacturing method. Since the structure of a prism sheet and the manufacturing method of a prism sheet should just suitably employ | adopt the method disclosed by prior art, for example, Unexamined-Japanese-Patent No. 5-169015, it does not explain in detail here, but a basic matter is as follows. The prism sheet is a structure in which a prism shape portion made of a photocurable resin is laminated on a transparent substrate. The prism shape has a shape in which a plurality of unit lenses for emitting light in a specific direction are arranged at a predetermined pitch in one or two dimensional directions. The most common form of the unit lens is a triangular column shape, but with special limitations. Is not.
본 발명의 조성물과 같이 광경화성 수지를 이용하여 프리즘 시트를 제조하는 방법은 크게 The method of manufacturing a prism sheet using photocurable resin like the composition of this invention is large
(1) 투명 기재 위에 본 발명의 프리즘 시트 형성용 조성물을 도포하는 단계(1) applying the composition for forming a prism sheet of the present invention on a transparent substrate
(2) 상기 조성물이 도포된 투명 기재를 롤러에 통과시키거나 다른 적절한 몰딩 공정을 수행함으로써 단위 렌즈를 형성하여 원하는 모양의 프리즘 형상부를 형성하는 단계(2) forming a unit lens by passing the transparent substrate coated with the composition through a roller or performing another suitable molding process to form a prism shape having a desired shape;
(3) 상기 프리즘 형상부를 경화시킬 수 있는 빛(주로 자외선)을 조사하여 상기 프리즘 형상부를 경화시키는 단계(3) curing the prism shape by irradiating light (mainly ultraviolet rays) capable of curing the prism shape;
의 세 가지 단계로 이루어질 수 있다.It can be done in three steps.
[실시예]EXAMPLE
이하 실시예와 합성예를 들어 본 발명을 더 구체적으로 설명한다. 본 발명이 속하는 분야의 평균적 기술자는 아래 실시예와 합성예에 기재된 실시 태양 외에 여러 가지 다른 형태로 본 발명을 변경할 수 있으며, 이하 실시예와 합성예는 본 발명을 예시할 따름이지 본 발명의 기술적 사상의 범위를 아래 실시예 범위로 한정하기 위한 의도라고 해석해서는 아니된다.Hereinafter, the present invention will be described in more detail with reference to Examples and Synthesis Examples. The average person skilled in the art to which the present invention pertains may modify the present invention in various other forms in addition to the embodiments described in the following Examples and Synthesis Examples, and the following Examples and Synthesis Examples illustrate the present invention only. It should not be construed as intended to limit the scope of the idea to the scope of the following examples.
[합성예]Synthesis Example
본 발명 조성물의 (A) 성분인 우레탄 (메트)아크릴레이트 화합물의 합성예를 제공한다. 화학식 1에 따른 구체적인 우레탄 (메트)아크릴레이트 화합물로서 분자 1-1과 1-2, 화학식 2에 따른 화합물로서 분자 2-1과 2-2, 그리고 화학식 3에 따른 화합물로서 분자 3-1의 합성 반응을 아래에 나타내었다.The synthesis example of the urethane (meth) acrylate compound which is (A) component of the composition of this invention is provided. Synthesis of molecules 3-1 as specific urethane (meth) acrylate compounds according to formula 1, molecules 1-1 and 1-2, molecules 2-1 and 2-2 as compounds according to formula 2, and compounds according to formula 3 The reaction is shown below.
<분자 1-1의 합성><Synthesis of Molecule 1-1>
500 mL 둥근바닥 플라스크에 5,5′-(1-메틸에틸리덴)비스[1,1′-(바이페닐)-2-올] 50 g, 디라우릴산디부틸주석 0.2 g과 톨루엔 290 mL를 투입하고 2-메틸-아크릴산-2-이소시안산에틸에스테르 44.33 g을 50℃에서 30분 동안 천천히 적가하였다. 이후 50℃에서 5시간 추가 교반하였다. 상기 용액을 물로 2회 씻어준 다음 Na2SO4를 사용하여 건조 후 여과, 농축하여 화합물 1-1을 생성하였다. 생성된 화합물 1-1의 굴절율은 1.5701이다.In a 500 mL round bottom flask, 50 g of 5,5 '-(1-methylethylidene) bis [1,1'-(biphenyl) -2-ol], 0.2 g of dibutyltin dilauryl and 290 mL of toluene It was added, and 44.33 g of 2-methyl-acrylic acid-2-isocyanate ethyl ester was slowly added dropwise at 50 ° C for 30 minutes. Then further stirred for 5 hours at 50 ℃. The solution was washed twice with water, dried using Na 2 SO 4 , filtered and concentrated to give compound 1-1. The refractive index of the resulting compound 1-1 is 1.5701.
C41H42N2O8 C 41 H 42 N 2 O 8
예상 분자량: 690.29Estimated molecular weight: 690.29
측정 분자량: 690.78Measured molecular weight: 690.78
C: 71.29%, H: 6.13%, N: 4.06%, O: 18.53%C: 71.29%, H: 6.13%, N: 4.06%, O: 18.53%
<1-2의 합성><1-2 Synthesis>
500 mL 둥근바닥 플라스크에 4,4′-[4-(1,1′-바이페닐일)메틸렌]비스[2-시클로헥실페놀] 50 g, 디라우릴산디부틸주석 0.2 g과 톨루엔 240 mL를 투입하고 2-메틸-아크릴산-2-이소시안산에틸 에스테르 30.07 g을 50℃에서 30분 동안 천천히 적가하였다. 이후 50℃에서 5시간 추가 교반하였다. 상기 용액을 물로 2회 씻어준 다음 Na2SO4를 사용하여 건조 후 여과, 농축하여 화합물 1-2를 생성하였다. 생성된 화합물 1-2의 굴절율은 1.5746이다.Into a 500 mL round bottom flask, 50 g of 4,4 '-[4- (1,1'-biphenylyl) methylene] bis [2-cyclohexylphenol], 0.2 g of dibutyltin dilauryl and 240 mL of toluene were added. 30.07 g of 2-methyl-acrylic acid-2-isocyanoic acid ethyl ester was slowly added dropwise at 50 ° C for 30 minutes. Then further stirred for 5 hours at 50 ℃. The solution was washed twice with water, dried using Na 2 SO 4 , filtered and concentrated to give compound 1-2. The refractive index of the resulting compound 1-2 is 1.5746.
C52H60N2O8 C 52 H 60 N 2 O 8
예상 분자량: 840.43Estimated molecular weight: 840.43
측정 분자량: 841.04Measured molecular weight: 841.04
C: 74.26%, H: 7.19, N: 3.33%, O: 15.22%C: 74.26%, H: 7.19, N: 3.33%, O: 15.22%
<2-1의 합성>Synthesis of 2-1
500 mL 둥근바닥 플라스크에 4,4′-[(3-메톡시-4-히드록시페닐)메틸렌]비스[2-시클로헥실-5-메틸페놀] 50g, 디라우릴산디부틸주석 0.2 g과 톨루엔 390 mL를 투입하고 2-메틸-아크릴산-2-이소시안산에틸 에스테르 48.08 g을 50℃에서 30분 동안 천천히 적가하였다. 이후 50℃에서 5시간 추가 교반하였다. 상기 용액을 물로 2회 씻어준 다음 Na2SO4를 사용하여 건조 후 여과, 농축하여 화합물 2-1을 생성하였다. 생성된 화합물 2-1의 굴절율은 1.5812이다.50 g of 4,4 '-[(3-methoxy-4-hydroxyphenyl) methylene] bis [2-cyclohexyl-5-methylphenol] in a 500 mL round bottom flask, 0.2 g of dibutyltin dilauryl acid and 390 toluene mL was added and 48.08 g of 2-methyl-acrylic acid-2-isocyanate ethyl ester was slowly added dropwise at 50 ° C for 30 minutes. Then further stirred for 5 hours at 50 ℃. The solution was washed twice with water, dried using Na 2 SO 4 , filtered and concentrated to give Compound 2-1. The refractive index of the resulting compound 2-1 is 1.5812.
C54H67N3O12 C 54 H 67 N 3 O 12
예상 분자량: 949.47Estimated molecular weight: 949.47
측정 분자량: 950.12Measured molecular weight: 950.12
C: 68.26%, H: 7.11%, N: 4.42%, O: 20.21%C: 68.26%, H: 7.11%, N: 4.42%, O: 20.21%
<2-2의 합성><2-2 synthesis>
500 mL 둥근바닥 플라스크에 4,4′,4″-에틸리딘트리스페놀 50g, 디라우릴디부틸주석 0.2g과 톨루엔 390 mL를 투입하고 2-메틸-아크릴산-2-이소시안산에틸 에스테르 48.08g을 50℃에서 30분 동안 천천히 적가하였다. 이후 50℃에서 5시간 추가 교반하였다. 상기 용액을 물로 2회 씻어준 다음 Na2SO4를 사용하여 건조 후 여 과, 농축하여 화합물 2-2를 생성하였다. 생성된 화합물 2-2의 굴절율은 1.5840이다.50 g of 4,4 ′, 4 ″ -ethylidedinetrisphenol, 0.2 g of dilauryldibutyltin and 390 mL of toluene were added to a 500 mL round bottom flask, and 48.08 g of 2-methyl-acrylic acid-2-isocyanate ethyl ester was added. Slow dropwise addition at 50 ° C. for 30 minutes. Then further stirred for 5 hours at 50 ℃. The solution was washed twice with water, dried using Na 2 SO 4 , filtered, and concentrated to give compound 2-2. The refractive index of the resulting compound 2-2 is 1.5840.
C41H45N3O12 C 41 H 45 N 3 O 12
예상 분자량: 771.30Estimated molecular weight: 771.30
측정 분자량: 771.81Measured molecular weight: 771.81
C: 63.80%, H: 5.88%, N: 5.44%, O: 24.88%C: 63.80%, H: 5.88%, N: 5.44%, O: 24.88%
<3-1의 합성>Synthesis of 3-1
500 mL 둥근바닥 플라스크에 4,4′,4″,4′″-(1,4-페닐렌디메틸리딘)테트라키스페놀 50 g, 디라우릴산디부틸주석 0.2 g과 톨루엔 390 mL를 투입하고 2-메틸- 아크릴산-2-이소시안산에틸 에스테르 65.46 g을 50℃에서 30분 동안 천천히 적가하였다. 이후 50℃에서 5시간 추가 교반하였다. 상기 용액을 물로 2회 씻어준 다음 Na2SO4를 사용하여 건조 후 여과, 농축하여 화합물 3-1을 생성하였다. 생성된 화합물 3-1의 굴절율은 1.5882이다.50 g of 4,4 ', 4 ", 4'"-(1,4-phenylenedimethylidine) tetrakisphenol, 0.2 g of dibutyltin dilauryl and 390 mL of toluene were added to a 500 mL round bottom flask. 65.46 g of methyl-acrylic acid-2-isocyanate ethyl ester was slowly added dropwise at 50 ° C for 30 minutes. Then further stirred for 5 hours at 50 ℃. The solution was washed twice with water, dried using Na 2 SO 4 , filtered and concentrated to give compound 3-1. The refractive index of the resulting compound 3-1 is 1.5882.
C60H62N4O16 C 60 H 62 N 4 O 16
예상 분자량: 1094.42Estimated molecular weight: 1094.42
측정 분자량: 1095.15Measured molecular weight: 1095.15
C: 65.80%, H: 5.71%, N: 5.12%, O: 23.37%C: 65.80%, H: 5.71%, N: 5.12%, O: 23.37%
<실시예><Example>
본 발명에 따른 프리즘 시트 형성용 조성물의 성능을 평가하기 위하여 실시예와 비교예 조성물을 제조하였다. 비교예와 실시예 조성물의 조성비는 하기 표 1과 같다. 표 1의 수치는 (A) 군 물질 전체 중량을 100으로 하여 환산한 중량부 값이다.In order to evaluate the performance of the composition for forming a prism sheet according to the present invention, Examples and Comparative Example compositions were prepared. The composition ratio of the comparative example and the example composition is as Table 1 below. The numerical value of Table 1 is the weight part value converted into the total weight of (A) group substance as 100.
※표의 설명※ Explanation of table
BR-42M : 에톡시레이티드 테트라브로모비스페놀 A 디메트아크릴레이트(일본 제일공업제약)BR-42M: ethoxylated tetrabromobisphenol A dimethacrylate (Japan Daiichi Kogyo Pharmaceutical Co., Ltd.)
BP-4EA : 디아크릴산 폴리에톡실레이트(n = 약 4) 비스페놀 에이 (일본 쿄에이화학)BP-4EA: diacrylic acid polyethoxylate (n = about 4) bisphenol A (Kyoei Chemical, Japan)
DPHA : 디펜타에리스리톨 헥사아크릴레이트 (일본 신나까무라社)DPHA: dipentaerythritol hexaacrylate (Shin-Nakamura, Japan)
TPO : 2,4,6-트리에틸벤조일다이펜틸포스핀 옥사이드 (스위스 시바스페셜티케미칼社)TPO: 2,4,6-triethylbenzoyldipentylphosphine oxide (Swiss Ciba Specialty Chemical Co., Ltd.)
I-184 : 1-하이드록시-사이클로헥실-페닐케톤(스위스 시바스페셜티케미칼社의 Irgacure 184)I-184: 1-hydroxy-cyclohexyl-phenyl ketone (Irgacure 184 from Ciba Specialty Chemicals, Switzerland)
SR-339 : 2-페녹시에틸 아크릴레이트 (미국 사토머社)SR-339: 2-phenoxyethyl acrylate (Sartomer, USA)
A-L4 : o-페닐페녹시에틸 아크릴레이트 (일본 신나까무라社)A-L4: o-phenylphenoxyethyl acrylate (Shinakamura, Japan)
PT-011 : 페녹시티오에틸 아크릴레이트 (한농화성)PT-011: Phenoxythioethyl Acrylate (Hanogenic)
상기 표 1에 따라 제조한 실시예와 비교예 조성물을 대상으로 아래 평가 항목의 물성을 측정하고 평가하였다. 측정 결과는 하기 표 2에 정리하였다.The physical properties of the following evaluation items were measured and evaluated for the Examples and Comparative Example compositions prepared according to Table 1 above. The measurement results are summarized in Table 2 below.
조성물의 점도Viscosity of the composition
브룩필드 디지털 점도계(모델: D-II+ Pro)를 사용하여 25℃에서 측정하였다. 점도가 1000 cPs 이상이면 프리즘 시트 형성용 조성물로서 적합하지 않다.Measurements were taken at 25 ° C. using a Brookfield Digital Viscometer (Model: D-II + Pro). Viscosity 1000 cPs If it is above, it is not suitable as a composition for prism sheet formation.
조성물의 경화 전 굴절률Refractive index before curing of the composition
아베 굴절계를 이용하여 20℃에서 589.3 nm의 파장에 대한 굴절률을 수지의 경화 전에 측정하였다. 고휘도를 지원하기 위하여 굴절률은 1.55를 넘는 것이 바람직하다.The refractive index for the wavelength of 589.3 nm at 20 ° C. was measured using an Abbe refractometer before curing of the resin. In order to support high brightness, the refractive index is preferably greater than 1.55.
경화 후 굴절률Refractive index after curing
자체 제작한 마이크로코터를 이용하여 프리즘이 각인되지 않은 민자 롤을 이용하여, 500 mJ/㎠의 에너지를 조사함으로써 25 ㎛의 두께로 PET 위에 본 발명의 프리즘 시트 형성용 조성물을 경화시켰다. 경화 후 아베 굴절계를 이용하여 589.3 nm의 광원에서 측정하였다.The composition for forming the prism sheet of the present invention was cured on a PET with a thickness of 25 μm by irradiation with an energy of 500 mJ / cm 2 using a private roll made without a prism imprinted using a self-made microcoater. After curing, it was measured under a light source of 589.3 nm using an Abbe refractometer.
경화 후 부착력Adhesion after curing
자체 제작한 마이크로코터를 이용하여 프리즘이 각인된 롤을 이용하여 500 mJ/㎠의 에너지(금속할로겐화물 램프)의 빛을 조사하여 25 ㎛의 두께와 피치를 가지는 프리즘 시트를 제작하였다. 이후 PET 필름의 코팅한 면에 줄 간격 1.5 mm로 11줄씩 가로줄과 세로줄을 그어서 칸의 수가 100 칸이 되게 한 다음, 3M사의 셀로테이프 600번을 붙였다가 5분 후 떼어내서 100 칸중 남아 있는 칸의 수를 평가하였다. 남아 있는 칸의 수가 적을수록 프리즘 시트 형성용 조성물로서 바람직하다.A prism sheet having a thickness and a pitch of 25 μm was manufactured by irradiating light of 500 mJ / cm 2 of energy (metal halide lamp) using a roll on which a prism was imprinted using a self-made microcoater. After that, draw 11 rows of horizontal and vertical lines with a line spacing of 1.5 mm on the coated side of the PET film so that the number of cells becomes 100 spaces, and then attach 3M cello tape No. 600 and remove it after 5 minutes. The numbers were evaluated. The smaller the number of compartments remaining, the more preferable the composition for forming a prism sheet.
연필 경도Pencil hardness
경화된 프리즘시트에 각각의 경도가 다른 연필을 45도 각도로 접촉시킨 후 하중 1000 g을 가하여 분당 130 mm의 속도로 이동시켰을 때, 프리즘 세모 기둥의 형태가 무너지지 않는 연필의 경도 중 가장 높은 경도를 기록하였다(미국 재료 표준인 ASTM D-3363을 따름).When the hardened prism sheet was brought into contact with a pencil of different hardness at a 45 degree angle and moved at a speed of 130 mm per minute with a load of 1000 g, the highest hardness among pencil hardnesses in which the shape of the prism triangular column did not collapse Recorded (according to ASTM D-3363, US material standard).
탄성 복원력Elastic resilience
자체 제작한 마이크로코터와 프리즘이 각인되지 않은 민자 롤을 이용하여 500 mJ/㎠의 에너지를 조사하여 25 ㎛의 두께로 PET 위에 조성물을 경화시킨 다음, 나노인덴터(모델: DUH-W201S, 일본 시마츠) 장비를 이용하여 측정하였다. 하중은 50 mN으로 하였고, 30℃ 항온 플레이트에서 측정하였다. 탄성 복원력의 단위는 %로 측정하였다. 측정값이 80% 이상이면 적절한 탄성 복원력이 있는 것으로 평가하였다.Using a self-made microcoater and a prism-free stamped roll, the composition was cured on PET with a thickness of 25 μm by irradiation of 500 mJ / cm 2 energy, followed by a nanoindenter (model: DUH-W201S, Japan) Was measured using the equipment. The load was 50 mN and measured on a 30 ° C. constant temperature plate. The unit of elastic restoring force was measured in%. When the measured value was 80% or more, it was evaluated that there was an appropriate elastic restoring force.
경화성Curable
자체 제작한 마이크로코터를 이용하여 25 ㎛의 두께로 코팅한 후 120 W의 금속할로겐화물 램프를 갖춘 자외선 경화 장치를 경화시킬 때 필요한 에너지(mJ/㎠)를 계산한다. 소모된 에너지가 200 mJ/㎠ 이하이면 바람직한 것으로 평가하였다.After coating to a thickness of 25 μm using a self-made microcoater, the energy (mJ / cm 2) required to cure an ultraviolet curing device equipped with a 120 W metal halide lamp is calculated. If the energy consumed is 200 mJ / ㎠ or less was evaluated as preferred.
연속 제조 중 이형성(Release property during continuous manufacturing ( 離型性離 型 性 ))
자체 제작한 마이크로코터과 프리즘이 각인되지 않은 민자 롤을 이용하여 200 mJ/㎠의 에너지를 조사한 다음, 민자 롤과 PET에 코팅된 경화막을 분리하였다. 경화막이 롤에서 쉽게 분리되면 ○, 약간의 힘을 들여 분리되면 △로 평가하고, 몰드에 접착한 수지층의 일부와 함께 분리되지 않는 경우는 ×로 평가하였다.Using a self-made microcoater and a prism-free stamped roll, the energy of 200 mJ / cm 2 was irradiated, and then the rolled film and the cured film coated on PET were separated. When a cured film isolate | separated easily in a roll, it evaluated as (triangle | delta) and (triangle | delta) when it isolate | separated with some force and evaluated as x when it did not separate with a part of resin layer adhere | attached on the mold.
실시예의 조성물을 상기 평가 방법에 의하여 평가한 결과를 아래 표 2에 정리하였다. The result of evaluating the composition of the Example by the said evaluation method is put together in Table 2 below.
표 2의 결과에 나타난 바와 같이, 본 발명에 따른 실시예 조성물은 점도가 모두 1000 cPs 미만으로 적절한 수준이었고, 경화성도 150~160 mJ/㎠으로 적합하였으며 이형성도 양호하여 프리즘 시트 형성의 가공성이 우수하였다. 비교예 조성물은 점도가 1000 cPs를 크게 넘어 적합하지 못하며, 경화성이 200 mJ/㎠을 많이 넘어 불량하였다.As shown in the results of Table 2, all of the example compositions according to the present invention had a suitable viscosity of less than 1000 cPs, suitable for curing properties of 150 to 160 mJ / cm 2, and good releasability, thereby providing excellent processability of prism sheet formation. It was. The comparative composition was not suitable for the viscosity exceeding 1000 cPs significantly, and the curability was poor beyond much 200 mJ / cm 2.
특히 실시예 조성물은 굴절률 면에서 우수하였는데, 조성물의 경화 전 굴절률은 모두 1.56보다 높았고, 경화 후 굴절률은 1.58을 넘어, 고휘도 프리즘 시트용으로 적합하다는 것을 보여주었다. 그에 반하여 비교예 조성물은 유럽 연합 환경 기준 RoHS에서 규제하고 있는 브롬을 함유하고 있어서 문제가 된다. 또한 상기 표 1의 비교예 조성물은 경화 전후 굴절률이 1.5603으로서 우수하지만, 이것은 점도가 매우 높은 상태일 때 얻을 수 있는 굴절율로서, 성형 가능한 점도인 1000 cPs 이하로 조성물을 가공했을 때는 발명이 목적하는 굴절률인 1.55에 못 미치게 된다.In particular, the example compositions were excellent in terms of refractive index, all of which had a refractive index higher than 1.56 before curing, and a refractive index after curing exceeding 1.58, showing that they were suitable for high brightness prism sheets. In contrast, the comparative composition contains bromine, which is regulated by the European Union Environmental Standard RoHS, which is problematic. In addition, although the comparative example composition of Table 1 has excellent refractive index before and after curing as 1.5603, this is a refractive index that can be obtained when the viscosity is very high, and when the composition is processed to 1000 cPs or less, which is a moldable viscosity, the refractive index desired by the invention Falls below 1.55.
본 발명의 실시예 조성물은 탄성 복원력과 경도가 높아 긁힘(scratch)에 대한 내성도 갖추고 있다. 표 2의 결과로부터 실시예 조성물이 80% 후반의 높은 탄성 복원력을 가지고 있으며, 연필로 측정한 경도도 높아 외력에 대한 저항성이 뛰어남을 알 수 있었다. 이러한 긁힘 저항성은 대형 디스플레이 화면에 필요한 대면적 프리즘 시트에 매우 중요하다.Example compositions of the present invention have high elastic restoring force and hardness and also have resistance to scratches. From the results of Table 2, it was found that the example composition has a high elastic restoring force of the late 80%, and the hardness measured by the pencil is also high, which is excellent in resistance to external force. This scratch resistance is very important for large area prism sheets required for large display screens.
이상과 같이 본 발명의 바람직한 실시 태양의 예를 들어 본 발명의 기술적 사상을 설명하였다. 본 명세서의 상세한 설명과 실시예에 사용된 용어는 해당 분야에서 평균적인 기술자에게 본 발명을 상세히 설명하기 위한 목적으로 쓰인 것일 뿐, 어느 특정 의미로 한정하거나 청구범위에 기재된 발명의 범위를 제한하기 위한 의도가 아니었음을 밝혀 둔다.As mentioned above, the technical idea of this invention was demonstrated to the example of the preferable embodiment of this invention. The terminology used in the description and examples herein is for the purpose of describing the invention in detail to those skilled in the art, and is intended to limit the scope of the invention in any particular sense or in the claims. It was not intended.
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| WO2018016634A1 (en) * | 2016-07-21 | 2018-01-25 | 三菱瓦斯化学株式会社 | Compound, resin, and composition, as well as resist pattern formation method and circuit pattern formation method |
| JPWO2018016634A1 (en) * | 2016-07-21 | 2019-05-09 | 三菱瓦斯化学株式会社 | Compound, resin and composition, and resist pattern forming method and circuit pattern forming method |
| CN109803950A (en) * | 2016-07-21 | 2019-05-24 | 三菱瓦斯化学株式会社 | Compound, resin and composition and corrosion-resisting pattern forming method and circuit pattern forming method |
| WO2021085481A1 (en) * | 2019-10-28 | 2021-05-06 | 三井化学株式会社 | Photocurable composition and dental product |
| JPWO2021085481A1 (en) * | 2019-10-28 | 2021-05-06 |
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