KR102649723B1 - Heat curable resin composition - Google Patents
Heat curable resin composition Download PDFInfo
- Publication number
- KR102649723B1 KR102649723B1 KR1020180166133A KR20180166133A KR102649723B1 KR 102649723 B1 KR102649723 B1 KR 102649723B1 KR 1020180166133 A KR1020180166133 A KR 1020180166133A KR 20180166133 A KR20180166133 A KR 20180166133A KR 102649723 B1 KR102649723 B1 KR 102649723B1
- Authority
- KR
- South Korea
- Prior art keywords
- resin composition
- thermosetting resin
- group
- acrylate
- binder resin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 229920005989 resin Polymers 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 52
- 239000011230 binding agent Substances 0.000 claims abstract description 46
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 33
- 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 24
- 125000005647 linker group Chemical group 0.000 claims abstract description 14
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 4
- -1 methacryloyloxy groups Chemical group 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 18
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 238000005054 agglomeration Methods 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000002087 whitening effect Effects 0.000 abstract description 13
- 230000000052 comparative effect Effects 0.000 description 22
- 230000008901 benefit Effects 0.000 description 18
- 239000000758 substrate Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 239000003822 epoxy resin Substances 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000005655 1,3-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([*:2])C1([H])[H] 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 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 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000006841 cyclic skeleton Chemical group 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HOSJNFCDDCLEBM-UHFFFAOYSA-N (2-phenyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1C1=CC=CC=C1 HOSJNFCDDCLEBM-UHFFFAOYSA-N 0.000 description 2
- VCJWMECOBCXFOF-UHFFFAOYSA-N (3-ethyloxetan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)COC1 VCJWMECOBCXFOF-UHFFFAOYSA-N 0.000 description 2
- RSHKWPIEJYAPCL-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CC)COC1 RSHKWPIEJYAPCL-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 125000005658 1,2-cycloheptylene group Chemical group 0.000 description 2
- 125000005654 1,2-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([*:1])C1([H])[H] 0.000 description 2
- 125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 2
- 125000005659 1,3-cycloheptylene group Chemical group 0.000 description 2
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical compound COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- FARWYUGFTNOIPS-UHFFFAOYSA-N [2-(trifluoromethyl)oxetan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1C(F)(F)F FARWYUGFTNOIPS-UHFFFAOYSA-N 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- KRGGVEDZUSPSAC-UHFFFAOYSA-N oxetan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCO1 KRGGVEDZUSPSAC-UHFFFAOYSA-N 0.000 description 2
- AMUUFLNQHMIHRP-UHFFFAOYSA-N oxetan-3-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1 AMUUFLNQHMIHRP-UHFFFAOYSA-N 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 1
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- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
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- BLLFPKZTBLMEFG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(O)=CC=C1N1C(=O)C=CC1=O BLLFPKZTBLMEFG-UHFFFAOYSA-N 0.000 description 1
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- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 description 1
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
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- URBZEXMYYYABCQ-UHFFFAOYSA-N butyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCCC URBZEXMYYYABCQ-UHFFFAOYSA-N 0.000 description 1
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- VUEYQLJAKGLDNR-UHFFFAOYSA-N butyl 2-ethoxyacetate Chemical compound CCCCOC(=O)COCC VUEYQLJAKGLDNR-UHFFFAOYSA-N 0.000 description 1
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- MENWVOUYOZQBDM-UHFFFAOYSA-N butyl 3-hydroxypropanoate Chemical compound CCCCOC(=O)CCO MENWVOUYOZQBDM-UHFFFAOYSA-N 0.000 description 1
- RRIRSNXZGJWTQM-UHFFFAOYSA-N butyl 3-methoxypropanoate Chemical compound CCCCOC(=O)CCOC RRIRSNXZGJWTQM-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- FWOHNFOTPCHCMT-UHFFFAOYSA-N carbonic acid;oxetane Chemical compound C1COC1.C1COC1.OC(O)=O FWOHNFOTPCHCMT-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000006292 cyclic linker group Chemical group 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- AWGWNMYTZFCQKW-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylic acid oxetane Chemical compound C1COC1.C1COC1.OC(=O)C1(C(O)=O)CCCCC1 AWGWNMYTZFCQKW-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- 125000003700 epoxy group Chemical group 0.000 description 1
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- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 description 1
- VBCSBEIIIFLVQV-UHFFFAOYSA-N methyl 3-butoxypropanoate Chemical compound CCCCOCCC(=O)OC VBCSBEIIIFLVQV-UHFFFAOYSA-N 0.000 description 1
- DMHHINXESLPPMV-UHFFFAOYSA-N methyl 3-propoxypropanoate Chemical compound CCCOCCC(=O)OC DMHHINXESLPPMV-UHFFFAOYSA-N 0.000 description 1
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- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCAOBJJSISYNMN-UHFFFAOYSA-N oxetane;terephthalic acid Chemical compound C1COC1.C1COC1.OC(=O)C1=CC=C(C(O)=O)C=C1 WCAOBJJSISYNMN-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HNYIJJOTPSKGJM-UHFFFAOYSA-N propoxymethyl acetate Chemical compound CCCOCOC(C)=O HNYIJJOTPSKGJM-UHFFFAOYSA-N 0.000 description 1
- LVDAGIFABMFXSJ-UHFFFAOYSA-N propyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCC LVDAGIFABMFXSJ-UHFFFAOYSA-N 0.000 description 1
- ADOFEJQZDCWAIL-UHFFFAOYSA-N propyl 2-ethoxyacetate Chemical compound CCCOC(=O)COCC ADOFEJQZDCWAIL-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- FIABMSNMLZUWQH-UHFFFAOYSA-N propyl 2-methoxyacetate Chemical compound CCCOC(=O)COC FIABMSNMLZUWQH-UHFFFAOYSA-N 0.000 description 1
- BMVTVMIDGMNRRR-UHFFFAOYSA-N propyl 2-propoxyacetate Chemical compound CCCOCC(=O)OCCC BMVTVMIDGMNRRR-UHFFFAOYSA-N 0.000 description 1
- KNCDNPMGXGIVOM-UHFFFAOYSA-N propyl 3-hydroxypropanoate Chemical compound CCCOC(=O)CCO KNCDNPMGXGIVOM-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
본 발명에 따른 열경화성 수지 조성물은 하이드록시알킬(메트)아크릴레이트 유래의 반복단위, 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위 및 불포화 카르복실산 유래의 반복단위를 포함하는 바인더 수지; 및 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트;를 포함하는 것을 특징으로 한다.
본 발명에 따른 열경화성 수지 조성물은 밀착성, 경도, 신뢰성이 우수하고 백화 현상이 억제된 경화막의 제조가 가능하다.The thermosetting resin composition according to the present invention includes a repeating unit derived from hydroxyalkyl (meth)acrylate, a repeating unit derived from (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from unsaturated carboxylic acid. binder resin; and a polyfunctional urethane acrylate containing a cyclic linking group.
The thermosetting resin composition according to the present invention has excellent adhesion, hardness, and reliability and is capable of producing a cured film with suppressed whitening phenomenon.
Description
본 발명은 열경화성 조성물, 특히 오버코트층으로 활용이 가능한 열경화성 조성물에 관한 것이다.The present invention relates to a thermosetting composition, particularly a thermosetting composition that can be used as an overcoat layer.
최근 정보화 기술(IT)이 발전함에 따라 디스플레이 분야에 대한 요구도 다양한 형태로 제시되고 있다. 예를 들면, 박형화, 경량화, 저소비 전력화 등의 특징을 지닌 여러 평판 표시 장치(Flat Panel Display device), 예를 들어, 액정표시장치(Liquid Crystal Display device), 플라즈마 표시장치(Plasma Display Panel device), 전계발광 표시장치(Electro Luminescent Display device), 유기발광다이오드 표시장치(Organic Light-Emitting Diode Display device) 등이 연구되고 있다.As information technology (IT) has recently developed, demands for the display field are also being presented in various forms. For example, various flat panel display devices with features such as thinner, lighter, and lower power consumption, such as liquid crystal display devices and plasma display devices, Electro Luminescent Display devices and Organic Light-Emitting Diode Display devices are being researched.
이러한 평판 표시 장치는, 컬러필터, ITO, 금속 전극층과 같은 다양한 구성으로 이루어지며, 이를 보호하는 오버코트층과 같은 경화막을 갖는 것이 일반적이다.These flat panel display devices are made up of various components such as color filters, ITO, and metal electrode layers, and generally have a cured film such as an overcoat layer to protect them.
대한민국 공개특허 제2016-0128218호는 경화성 조성물, 경화막, 유기 EL 표시 장치, 액정 표시 장치, 터치 패널 및 터치 패널 표시 장치에 관한 것으로서, 성분A로서, 에틸렌성 불포화 화합물, 성분B로서, 중합개시제, 성분C로서, 알콕시실란 화합물, 성분D로서, 유기 용제, 및, 성분E로서, 무기 입자를 함유하고, 성분A가, 5관능 이상의 우레탄(메타)아크릴레이트를 포함하고, 상기 5관능 이상의 우레탄(메타)아크릴레이트의 함유량이, 성분A의 함유량 100질량부에 대해, 20∼100질량부이고, 상기 5관능 이상의 우레탄(메타)아크릴레이트가, 중량 평균 분자량 10,000 이상인 우레탄(메타)아크릴레이트, 및, 분자량 5,000 이하인 우레탄(메타)아크릴레이트를 포함하는 것을 특징으로 하는 경화성 조성물에 관한 내용을 개시하고 있다.Republic of Korea Patent Publication No. 2016-0128218 relates to a curable composition, a cured film, an organic EL display device, a liquid crystal display device, a touch panel, and a touch panel display device. As component A, an ethylenically unsaturated compound, and as component B, a polymerization initiator. , an alkoxysilane compound as component C, an organic solvent as component D, and an inorganic particle as component E, and component A contains urethane (meth)acrylate having 5 or more functions, and the urethane having 5 or more functions. The content of (meth)acrylate is 20 to 100 parts by mass based on 100 parts by mass of component A, and the urethane (meth)acrylate having the above five or more functional properties is a urethane (meth)acrylate having a weight average molecular weight of 10,000 or more, And, it discloses information about a curable composition comprising urethane (meth)acrylate having a molecular weight of 5,000 or less.
그러나, 종래 열경화성 수지 조성물을 이용하여 형성된 경화막의 경우 하부기판에 대한 도포성 및 밀착성이 우수하지 못해 경화막이 박리되고 또는 백화현상이 발생하는 문제가 있다.However, in the case of a cured film formed using a conventional thermosetting resin composition, the applicability and adhesion to the lower substrate are not excellent, so there is a problem in that the cured film peels off or whitening occurs.
그러므로 도포성 및 밀착성이 우수하여 신뢰성이 우수할 뿐만 아니라, 백화현상을 억제할 수 있는 경화성 조성물의 개발이 요구되고 있다.Therefore, there is a need for the development of a curable composition that not only has excellent applicability and adhesion and reliability, but can also suppress whitening.
본 발명은 백화현상을 억제하고 도포성 및 신뢰성이 우수한 경화막의 제조가 가능한 열경화성 수지 조성물을 제공하고자 한다.The present invention seeks to provide a thermosetting resin composition capable of suppressing whitening and producing a cured film with excellent applicability and reliability.
또한, 본 발명은 백화현상이 억제되고, 도포성 및 신뢰성이 우수한 경화막을 제공하고자 한다.In addition, the present invention seeks to provide a cured film that suppresses whitening and has excellent applicability and reliability.
본 발명은 하이드록시알킬(메트)아크릴레이트 유래의 반복단위, 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위 및 불포화 카르복실산 유래의 반복단위를 포함하는 바인더 수지; 및 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트;를 포함하는 열경화성 수지 조성물을 제공한다.The present invention relates to a binder resin comprising a repeating unit derived from a hydroxyalkyl (meth)acrylate, a repeating unit derived from a (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from an unsaturated carboxylic acid; and a polyfunctional urethane acrylate containing a cyclic linking group.
또한, 본 발명은 전술한 열경화성 수지 조성물의 경화물을 포함하는 경화막을 제공한다.Additionally, the present invention provides a cured film containing a cured product of the thermosetting resin composition described above.
본 발명에 따른 열경화성 수지 조성물은 백화현상이 억제되고, 도포성 및 신뢰성이 우수한 경화막의 제조가 가능한 이점이 있다.The thermosetting resin composition according to the present invention has the advantage of suppressing whitening and enabling the production of a cured film with excellent applicability and reliability.
또한, 본 발명에 따른 경화막은 백화현상이 억제되고, 도포성 및 신뢰성이 우수한 이점이 있으며, 특히 오버코트층으로서의 활용이 우수한 이점이 있다.In addition, the cured film according to the present invention has the advantage of suppressing whitening, excellent applicability and reliability, and especially excellent usability as an overcoat layer.
이하, 본 발명에 대하여 더욱 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 직접 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 개재되는 경우도 포함한다.In the present invention, when a member is said to be located “on” another member, this includes not only the case where a member is in direct contact with another member, but also the case where another member is interposed between the two members.
본 발명에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.In the present invention, when a part "includes" a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
<열경화성 수지 조성물><Thermosetting resin composition>
본 발명의 한 양태는, 하이드록시알킬(메트)아크릴레이트 유래의 반복단위, 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위 및 불포화 카르복실산 유래의 반복단위를 포함하는 바인더 수지; 및 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트;를 포함하는 열경화성 수지 조성물에 관한 것이다.One aspect of the present invention is a binder comprising a repeating unit derived from a hydroxyalkyl (meth)acrylate, a repeating unit derived from a (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from an unsaturated carboxylic acid. profit; and a polyfunctional urethane acrylate containing a cyclic linking group. It relates to a thermosetting resin composition comprising a.
본 발명에 따른 열경화성 수지 조성물은 우레탄 아크릴레이트가 가지는 우수한 경도를 유지하면서도, 우레탄 아크릴레이트의 단점인 도포성, 밀착성, 신뢰성이 개선된 경화막의 제조가 가능하다.The thermosetting resin composition according to the present invention can produce a cured film with improved applicability, adhesion, and reliability, which are the disadvantages of urethane acrylate, while maintaining the excellent hardness of urethane acrylate.
바인더 수지binder resin
본 발명에 따른 바인더 수지는 하이드록시알킬(메트)아크릴레이트 유래의 반복단위, 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위 및 불포화 카르복실산 유래의 반복단위를 포함한다.The binder resin according to the present invention includes a repeating unit derived from hydroxyalkyl (meth)acrylate, a repeating unit derived from (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from unsaturated carboxylic acid.
본 발명에 따른 바인더 수지는 하이드록시알킬(메트)아크릴레이트 유래의 반복단위를 포함한다.The binder resin according to the present invention contains repeating units derived from hydroxyalkyl (meth)acrylate.
본 발명에 있어서, "알킬"은 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 4인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, tert-부틸, sec-부틸등이 있으나, 이들에 한정되지 않는다.In the present invention, “alkyl” may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 4. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and sec-butyl.
상기 하이드록시알킬(메트)아크릴레이트는 상기 바인더 수지에 대하여 1 내지 60 mol%, 바람직하게는 5 내지 45 mol%, 더욱 바람직하게는 10 내지 30 mol%일 수 있으나 이에 한정되지는 않는다.The hydroxyalkyl (meth)acrylate may be 1 to 60 mol%, preferably 5 to 45 mol%, and more preferably 10 to 30 mol% relative to the binder resin, but is not limited thereto.
다만, 상기 범위 내인 경우 하부기판과의 접착력이 우수하고, 오래 지속될 수 있는 이점이 있어 바람직하다.However, if it is within the above range, it is preferable because it has excellent adhesion to the lower substrate and has the advantage of being long-lasting.
본 발명에 따른 바인더 수지는 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위를 포함한다.The binder resin according to the present invention contains a repeating unit derived from (meth)acrylate containing an alicyclic cyclic epoxy group.
상기 지환족 고리형 에폭시기기를 함유하는 (메트)아크릴레이트는 지환족 고리에 직접 연결되거나 다른 연결기를 통해 에폭시 구조가 존재하는 구조를 가진 것이면 제한 없이 사용할 수 있다.The (meth)acrylate containing the alicyclic cyclic epoxy group can be used without limitation as long as it is directly connected to the alicyclic ring or has an epoxy structure through another linking group.
상기 지환족 고리형 에폭시기는 상기 바인더 수지에 대하여 5 내지 80 mol%, 바람직하게는 10 내지 70 mol%, 더욱 바람직하게는 20 내지 60 mol%일 수 있으나 이에 한정되지는 않는다.The alicyclic cyclic epoxy group may be present in an amount of 5 to 80 mol%, preferably 10 to 70 mol%, and more preferably 20 to 60 mol%, based on the binder resin, but is not limited thereto.
다만, 상기 범위 내인 경우 하부기판과의 밀착력이 우수한 이점이 있어 바람직하다.However, if it is within the above range, it is preferable because it has the advantage of excellent adhesion to the lower substrate.
본 발명에 따른 바인더 수지는 불포화 카르복실산 유래의 반복단위를 포함한다.The binder resin according to the present invention contains repeating units derived from unsaturated carboxylic acids.
상기 불포화 카르복실산은 예컨대 아크릴산, 메타크릴산, 크로톤산, 이타콘산, 말레산, 푸마르산일 수 있으며, 구체적으로 아크릴산일 수 있다.The unsaturated carboxylic acid may be, for example, acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, and specifically may be acrylic acid.
상기 불포화 카르복실산 유래의 반복단위는 상기 바인더 수지에 대하여 1 내지 40 mol%, 바람직하게는 2 내지 30 mol%, 더욱 바람직하게는 5 내지 20 mol%일 수 있으나 이에 한정되지는 않는다.The repeating unit derived from the unsaturated carboxylic acid may be 1 to 40 mol%, preferably 2 to 30 mol%, and more preferably 5 to 20 mol% relative to the binder resin, but is not limited thereto.
다만, 상기 범위 내인 경우 적절한 경화 속도와 상용성을 보완하는 이점이 있어 바람직하다.However, if it is within the above range, it is preferable because it has the advantage of complementing appropriate curing speed and compatibility.
본 발명의 일 실시형태에 있어서, 상기 바인더 수지는 하기 화학식 1로 표시될 수 있다.In one embodiment of the present invention, the binder resin may be represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
A1 및 A2는 각각 독립적으로 C1 내지 C4 알킬렌기이고,A 1 and A 2 are each independently a C1 to C4 alkylene group,
R은 각각 독립적으로 수소 또는 메틸기이며,R is each independently a hydrogen or methyl group,
상기 바인더 수지 내,In the binder resin,
a는 10 내지 40 mol%이고,a is 10 to 40 mol%,
b는 20 내지 60 mol%이며,b is 20 to 60 mol%,
c는 5 내지 40 mol%이다.c is 5 to 40 mol%.
본 발명에 따른 바인더 수지가 하기 화학식 1로 표시되는 경우 적절한 경화 속도를 가지고, 경화 후 기판과의 밀착력이 충분하고 오래 지속되는 이점이 있어 바람직하다.The binder resin according to the present invention represented by the following formula (1) is preferred because it has an appropriate curing speed, has sufficient adhesion to the substrate after curing, and has the advantage of lasting a long time.
본 발명에 있어서, 상기 "알킬렌기"는 2가인 것을 제외하고는 전술한 알킬에 관한 설명을 적용할 수 있다.In the present invention, the description of alkyl described above can be applied, except that the “alkylene group” is divalent.
본 발명의 또 다른 실시형태에 있어서, 상기 바인더 수지는 옥세탄기를 함유하는 (메트)아크릴레이트 유래의 반복단위를 더 포함할 수 있다.In another embodiment of the present invention, the binder resin may further include a repeating unit derived from (meth)acrylate containing an oxetane group.
상기 옥세탄기를 함유하는 (메트)아크릴레이트는 분자 구조 내 적어도 하나의 옥세탄 고리(4원 고리 에테르)를 갖는 화합물일 수 있으며, 예컨대, (3-에틸옥세탄-3-일)메틸 메타크릴레이트, 3-(메타크릴로일옥시메틸)옥세탄, 3-(메타크릴로일옥시메틸)-3-에틸옥세탄, 3-(메타크릴로일옥시메틸)-2-트리플루오로메틸옥세탄, 3-(메타크릴로일옥시메틸)-2-페닐옥세탄, 2-(메타크릴로일옥시메틸)옥세탄, 2-(메타크릴로일옥시메틸)-4-트리플루오로메틸옥세탄 등을 들 수 있다.The (meth)acrylate containing the oxetane group may be a compound having at least one oxetane ring (4-membered ring ether) in the molecular structure, for example, (3-ethyloxetan-3-yl)methyl methacryl. Late, 3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane Cetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethylox Setan, etc. can be mentioned.
상기 옥세탄기를 함유하는 (메트)아크릴레이트 유래의 반복단위는 상기 바인더 수지에 대하여 10 내지 60 mol%, 바람직하게는 15 내지 50 mol%, 더욱 바람직하게는 20 내지 40mol%일 수 있으나 이에 한정되지는 않는다.The repeating unit derived from (meth)acrylate containing the oxetane group may be 10 to 60 mol%, preferably 15 to 50 mol%, and more preferably 20 to 40 mol% relative to the binder resin, but is not limited thereto. does not
다만, 상기 범위 내인 경우 밀착력과 상온보존성을 동시에 취할 수 있는 이점이 있어 바람직하다.However, if it is within the above range, it is preferable because it has the advantage of achieving both adhesion and room temperature preservation at the same time.
본 발명의 또 다른 실시형태에 있어서, 상기 바인더 수지는 하기 화학식 2로 표시될 수 있다.In another embodiment of the present invention, the binder resin may be represented by the following formula (2).
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
A1 내지 A3은 각각 독립적으로 C1 내지 C4 알킬렌기이고,A 1 to A 3 are each independently a C1 to C4 alkylene group,
R은 각각 독립적으로 수소 또는 메틸기이며,R is each independently a hydrogen or methyl group,
상기 바인더 수지 내,In the binder resin,
a는 10 내지 30 mol%이고,a is 10 to 30 mol%,
b는 20 내지 60 mol%이고,b is 20 to 60 mol%,
c는 5 내지 20 mol%이고,c is 5 to 20 mol%,
d는 20 내지 40 mol%이다.d is 20 to 40 mol%.
본 발명에 따른 바인더 수지가 상기 화학식 2로 표시되는 경우, 경화막이 하부 기판과의 밀착력이 좋고, 오래 지속되는 이점이 있으며, 바인더 수지의 상온보존이 가능하여 취급성이 우수한 이점이 있어 바람직하다.When the binder resin according to the present invention is represented by the above formula (2), the cured film has the advantage of good adhesion to the lower substrate, lasts a long time, and has the advantage of excellent handleability because the binder resin can be stored at room temperature.
구체적으로, 본 발명에 있어서, 상기 바인더 수지는 하기 화학식 3으로 표시될 수 있다. Specifically, in the present invention, the binder resin may be represented by the following formula (3).
[화학식 3][Formula 3]
상기 바인더 수지 내,In the binder resin,
a 내지 d는 상기 화학식 2에서 정의한 바와 같다.a to d are as defined in Formula 2 above.
본 발명에 따른 바인더 수지는 추가의 반복단위를 더 포함할 수 있다. 상기 반복단위를 형성하는 단량체로는 특별히 한정되지 않으나, 예를 들면, 크로톤산 등의 모노카르복실산류; 푸마르산, 메사콘산, 이타콘산 등의 디카르복실산류 및 이들의 무수물; ω-카르복시폴리카프로락톤모노(메타)아크릴레이트 등의 양 말단에 카르복시기와 수산기를 갖는 폴리머의 모노(메타)아크릴레이트류; 비닐톨루엔, p-클로로스티렌, o-메톡시스티렌, m-메톡시스티렌, p-메톡시스티렌, o-비닐벤질메틸에테르, m-비닐벤질메틸에테르, p-비닐벤질메틸에테르, o-비닐 벤질글리시딜에테르, m-비닐벤질글리시딜에테르, p-비닐벤질글리시딜에테르 등의 방향족 비닐 화합물; N-시클로헥실말레이미드, N-벤질말레이미드, N-페닐말레이미드, N-o-히드록시페닐말레이미드, N-m-히드록시페닐말레이미드, N-p-히드록시페닐말레이미드, N-o-메틸페닐말레이미드, N-m-메틸페닐말레이미드, N-p-메틸페닐말레이미드, N-o-메톡시페닐말레이미드, N-m-메톡시페 말레이미드, N-p-메톡시페닐말레이미드 등의 N-치환 말레이미드계 화합물; 시클로펜틸(메타)아크릴레이트, 2-메틸시클로헥실(메타)아크릴레이트, 2-디시클로펜타닐옥시에틸(메타)아크릴레이트 등의 지환족(메타)아크릴레이트류; 페닐(메타)아크릴레이트 등의 아릴(메타)아크릴레이트류; 3-(메타크릴로일옥시메틸)옥세탄, 3-(메타크릴로일옥시메틸)-3-에틸옥세탄, 3-(메타크릴로일옥시메틸)-2-트리플루오로메틸옥세탄, 3-(메타크릴로일옥시메틸)-2-페닐옥세탄, 2-(메타크릴로일옥시메틸)옥세탄, 2-(메타크릴로일옥시메틸)-4-트리플루오로메틸옥세탄 등의 불포화 옥세탄 화합물; 메틸글리시딜(메타)아크릴레이트 등의 불포화 옥시란 화합물; 탄소수 4 내지 16의 시클로알칸 또는 디시클로알칸고리로 치환된 (메타)아크릴레이트; 등을 들 수 있다. 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다.The binder resin according to the present invention may further include additional repeating units. The monomer forming the repeating unit is not particularly limited, but examples include monocarboxylic acids such as crotonic acid; dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid, and their anhydrides; Mono(meth)acrylates of polymers having carboxyl groups and hydroxyl groups at both ends, such as ω-carboxypolycaprolactone mono(meth)acrylate; Vinyl toluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinyl Aromatic vinyl compounds such as benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, and p-vinyl benzyl glycidyl ether; N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m -N-substituted maleimide compounds such as methylphenylmaleimide, N-p-methylphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, and N-p-methoxyphenylmaleimide; Alicyclic (meth)acrylates such as cyclopentyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, and 2-dicyclopentanyloxyethyl (meth)acrylate; Aryl (meth)acrylates such as phenyl (meth)acrylate; 3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane, etc. unsaturated oxetane compounds; Unsaturated oxirane compounds such as methylglycidyl (meth)acrylate; (meth)acrylate substituted with a cycloalkane or dicycloalkane ring having 4 to 16 carbon atoms; etc. can be mentioned. These can be used alone or in combination of two or more types.
본 발명의 또 다른 실시형태에 있어서, 상기 바인더 수지는 상기 열경화성 수지 조성물 전체 100 중량부에 대하여 5 내지 60 중량부, 바람직하게는 5 내지 50 중량부, 더욱 바람직하게는 7 내지 30 중량부로 포함될 수 있다.In another embodiment of the present invention, the binder resin may be included in an amount of 5 to 60 parts by weight, preferably 5 to 50 parts by weight, and more preferably 7 to 30 parts by weight, based on 100 parts by weight of the total thermosetting resin composition. there is.
상기 바인더 수지가 상기 범위 내로 포함되는 경우 도포성이 우수하여 경화막 제조가 용이하고, 우수한 밀착성 및 신뢰성의 부여가 가능하며, 동시에 경도와 같은 기계적 물성이 우수한 경화막의 형성이 가능한 이점이 있다. 또한, 상용성이 우수해짐에 따라 백화현상의 발생을 억제할 수 있는 이점이 있다.When the binder resin is contained within the above range, there is an advantage in that coating properties are excellent, making it easy to manufacture a cured film, providing excellent adhesion and reliability, and at the same time forming a cured film with excellent mechanical properties such as hardness. In addition, as compatibility improves, there is an advantage in suppressing the occurrence of whitening phenomenon.
상기 바인더 수지의 산가는 특별히 한정하지는 않으나 20 내지 100 KOHmg/g일 수 있으며, 바람직하게는 40 내지 90KOHmg/g, 더욱 바람직하게는 60 내지 90KOHmg/g일 수 있다. 상기 바인더 수지의 산가가 상기 범위 내인 경우, 본 발명에 따른 열경화성 수지 조성물에 포함되는 다른 구성 요소와의 상용성이 우수하고, 적절한 경화속도를 가지는 이점이 있으므로 바람직하다. 상기 바인더 수지의 중량평균 분자량은 5,000 내지 25,000, 바람직하게는 6,000 내지 20,000, 더욱 바람직하게는 7,000 내지 12,000일 수 있으며, 상기 범위 내에서 가장 우수한 물성을 나타낼 수 있으므로 상기 바인더 수지의 중량평균 분자량은 상기 범위를 만족하는 것이 바람직하다. The acid value of the binder resin is not particularly limited, but may be 20 to 100 KOH mg/g, preferably 40 to 90 KOH mg/g, and more preferably 60 to 90 KOH mg/g. When the acid value of the binder resin is within the above range, it is preferable because it has the advantage of excellent compatibility with other components included in the thermosetting resin composition according to the present invention and an appropriate curing speed. The weight average molecular weight of the binder resin may be 5,000 to 25,000, preferably 6,000 to 20,000, and more preferably 7,000 to 12,000. Since the best physical properties can be exhibited within the above range, the weight average molecular weight of the binder resin is as follows. It is desirable to satisfy the range.
고리형 ring shaped 연결기를connector 함유하는 containing 다관능multi-sensory 우레탄 urethane 아크릴레이트Acrylate
본 발명에 따른 열경화성 수지 조성물은 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트를 포함한다. The thermosetting resin composition according to the present invention includes a polyfunctional urethane acrylate containing a cyclic linking group.
본 발명에 있어서, 상기 고리형 연결기는 치환 또는 비치환된 지방족 고리형 연결기일 수 있다. 지방족 고리형 연결기는 탄소 원자로 이루어지는 고리형 골격을 포함하는 것으로, 고리형 골격을 구성하는 탄소 원자로 연결하는 기이다. 고리형 골격을 구성하는 탄소 원자수는 3 ∼ 8 인 것이 바람직하고, 4 ∼ 7 인 것이 보다 바람직하고, 5 또는 6 인 것이 더욱 바람직하고, 6 인 것이 더욱 바람직하다. In the present invention, the cyclic linking group may be a substituted or unsubstituted aliphatic cyclic linking group. An aliphatic cyclic linking group is a group that includes a cyclic skeleton made of carbon atoms and is connected to the carbon atoms constituting the cyclic skeleton. The number of carbon atoms constituting the cyclic skeleton is preferably 3 to 8, more preferably 4 to 7, more preferably 5 or 6, and still more preferably 6.
상기 지방족 고리형 연결기의 구체예로서, 1,1-시클로부틸렌기, 1,2-시클로부틸렌기, 1,1-시클로펜틸렌기, 1,2-시클로펜틸렌기, 1,3-시클로펜틸렌기, 1,1-시클로헥실렌기, 1,2-시클로헥실렌기, 1,3-시클로헥실렌기, 1,1-시클로헵틸렌기, 1,2-시클로헵틸렌기, 1,3-시클로헵틸렌기, 1,4-시클로헵틸렌기, 1,1-시클로옥틸렌기, 1,2-시클로옥틸렌기, 1,3-시클로옥틸렌기, 1,4-시클로옥틸렌기, 2,2-아다만틸렌기, 2,4-아다만틸렌기를 들 수 있다. 바람직한 지방족 고리형 연결기의 구체예로서, 1,1-시클로펜틸렌기, 1,2-시클로펜틸렌기, 1,3-시클로펜틸렌기, 1,1-시클로헥실렌기, 1,2-시클로헥실렌기, 1,3-시클로헥실렌기, 1,1-시클로헵틸렌기, 1,2-시클로헵틸렌기, 1,3-시클로헵틸렌기, 2,2-아다만틸렌기, 1,4-아다만틸렌기를 들 수 있고, 더욱 바람직한 지방족 고리형 연결기의 구체예로서, 1,1-시클로헥실렌기, 1,2-시클로헥실렌기, 1,3-시클로헥실렌기, 1,4-시클로헥실렌기, 2,2-아다만틸렌기, 1,4-아다만틸렌기를 들 수 있다.Specific examples of the aliphatic cyclic linking group include 1,1-cyclobutylene group, 1,2-cyclobutylene group, 1,1-cyclopentylene group, 1,2-cyclopentylene group, 1,3-cyclopentylene group, 1,1-cyclohexylene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,1-cycloheptylene group, 1,2-cycloheptylene group, 1,3-cycloheptylene group , 1,4-cycloheptylene group, 1,1-cyclooctylene group, 1,2-cyclooctylene group, 1,3-cyclooctylene group, 1,4-cyclooctylene group, 2,2-adamantylene group, A 2,4-adamantylene group may be mentioned. Specific examples of preferred aliphatic cyclic linking groups include 1,1-cyclopentylene group, 1,2-cyclopentylene group, 1,3-cyclopentylene group, 1,1-cyclohexylene group, and 1,2-cyclohexylene. group, 1,3-cyclohexylene group, 1,1-cycloheptylene group, 1,2-cycloheptylene group, 1,3-cycloheptylene group, 2,2-adamantylene group, 1,4-adamane A tylene group can be mentioned, and specific examples of more preferable aliphatic cyclic linking groups include 1,1-cyclohexylene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, and 1,4-cyclohexylene group. Silene group, 2,2-adamantylene group, and 1,4-adamantylene group can be mentioned.
상기 지방족 고리형 연결기는 치환되어 있어도 된다. 치환기로는, 예를 들어 알킬기 또는 알콕시기를 들 수 있고, 예컨대, 상기 고리형 연결기는 메틸기 또는 프로필기로 치환된 시클로헥실렌기일 수 있다.The aliphatic cyclic linking group may be substituted. Examples of the substituent include an alkyl group or an alkoxy group, and for example, the cyclic linking group may be a cyclohexylene group substituted with a methyl group or a propyl group.
본 발명에 있어서, 알킬기는 전술한 내용을 적용할 수 있다.In the present invention, the above description can be applied to the alkyl group.
본 발명에 있어서, 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 4인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 4 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, etc., but is not limited thereto.
본 발명의 또 다른 실시형태에 있어서, 상기 다관능 우레탄 아크릴레이트는 2 이상의 우레탄 결합을 함유하고, 1 이상의 메타아크릴로일옥시기를 함유하며, 상기 고리형 연결기는 상기 우레탄 결합간을 연결하는 것일 수 있다.In another embodiment of the present invention, the polyfunctional urethane acrylate contains two or more urethane bonds and one or more methacryloyloxy groups, and the cyclic linking group may connect the urethane bonds. there is.
본 발명에 따른 우레탄 아크릴레이트가 2 이상의 우레탄 결합을 함유하고, 1 이상의 메타아크릴로일옥시기를 함유하며, 상기 우레탄 결합이 상기 고리형 연결기로 연결되는 경우 경도가 우수하면서도 유연한 경도막을 제조할 수 있어 플렉서블 디스플레이에 적용이 용이한 이점이 있다. 또한, 백화현상을 억제하면서도 투과율이 우수한 경화막의 제조가 가능한 이점이 있다.When the urethane acrylate according to the present invention contains two or more urethane bonds and one or more methacryloyloxy groups, and the urethane bonds are connected to the cyclic linker, a hard film with excellent hardness and flexibility can be produced. It has the advantage of being easy to apply to flexible displays. In addition, there is an advantage in that it is possible to manufacture a cured film with excellent transmittance while suppressing whitening.
본 발명의 또 다른 실시형태에 있어서, 상기 다관능 우레탄 아크릴레이트는 관능기 수가 6 이상일 수 있다. 상기 다관능 우레탄 아크릴레이트의 관능기 수가 6 이상인 경우 우수한 경도를 가지고 표면스크래치에 대한 내성이 우수한 경화막의 제조가 가능한 이점이 있다.In another embodiment of the present invention, the multifunctional urethane acrylate may have 6 or more functional groups. When the number of functional groups of the multifunctional urethane acrylate is 6 or more, there is an advantage in that it is possible to manufacture a cured film with excellent hardness and excellent resistance to surface scratches.
본 발명의 또 다른 실시형태에 있어서, 상기 다관능 우레탄 아크릴레이트는 관능기 수가 10 이상일 수 있다. 바람직하게는, 상기 다관능 우레탄 아크릴레이트는 관능기 수가 10 이상 15 이하일 수 있으며, 이 경우 전술한 효과가 극대화되는 이점이 있다.In another embodiment of the present invention, the multifunctional urethane acrylate may have 10 or more functional groups. Preferably, the number of functional groups in the multifunctional urethane acrylate may be 10 or more and 15 or less, and in this case, there is an advantage in that the above-mentioned effects are maximized.
상기 다관능 우레탄 아크릴레이트는 하기 화학식 4 또는 화학식 5로 표시될 수 있으나 이에 한정되지는 않는다.The multifunctional urethane acrylate may be represented by the following Chemical Formula 4 or Chemical Formula 5, but is not limited thereto.
[화학식 4][Formula 4]
[화학식 5] [Formula 5]
본 발명의 또 다른 실시형태에 있어서, 상기 다관능 우레탄 아크릴레이트는 상기 열경화성 수지 조성물 전체 100 중량부에 대하여 35 내지 95 중량부, 바람직하게는 37 내지 93 중량부, 더욱 바람직하게는 39 내지 90 중량부일 수 있으며, 이 경우 경화된 도막의 경도가 우수하고, 표면스크래치에 대한 내성이 우수하기 때문에 바람직하다. In another embodiment of the present invention, the polyfunctional urethane acrylate is contained in an amount of 35 to 95 parts by weight, preferably 37 to 93 parts by weight, more preferably 39 to 90 parts by weight, based on 100 parts by weight of the total thermosetting resin composition. It may be negative, and in this case, it is preferable because the hardness of the cured film is excellent and the resistance to surface scratches is excellent.
본 발명에 따른 열경화성 수지 조성물은 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트를 포함하기 때문에 상기 바인더 수지와의 상용성이 우수하여 우수한 경도를 유지한 채, 하부 기재와의 밀착력, 신뢰성을 확보하고 나아가 백화 현상이 억제된 경화막의 제조가 가능한 이점이 있다.Since the thermosetting resin composition according to the present invention contains a multifunctional urethane acrylate containing a cyclic linking group, it has excellent compatibility with the binder resin, maintaining excellent hardness, securing adhesion to the lower substrate, and reliability. Furthermore, there is an advantage in that it is possible to manufacture a cured film with suppressed whitening phenomenon.
본 발명의 또 다른 실시형태에 있어서, 상기 열경화성 수지 조성물은 용제; 및 충진제, 다른 고분자 화합물, 경화제, 레벨링제, 밀착성 개선제, 산화 방지제, 라디컬 발생제, 슬립성 개선제, 자외선 흡수제, 응집 방지제 및 연쇄 이동제로 이루어진 군에서 선택되는 첨가제;로 이루어진 군에서 선택되는 1 이상을 더 포함할 수 있다.In another embodiment of the present invention, the thermosetting resin composition includes a solvent; and an additive selected from the group consisting of fillers, other polymer compounds, curing agents, leveling agents, adhesion improvers, antioxidants, radical generators, slip improvers, ultraviolet absorbers, agglomeration inhibitors, and chain transfer agents; 1 selected from the group consisting of It may include more than the above.
용제solvent
상기 용제는 당해 분야에서 통상적으로 사용하는 것이라면 어떠한 것이라도 제한 없이 사용할 수 있다.The solvent may be any solvent commonly used in the field without limitation.
상기 용제의 구체적인 예로는 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노프로필에테르 및 에틸렌글리콜모노부틸에테르와 같은 에틸렌글리콜모노알킬에테르류; 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜에틸메틸에테르, 디에틸렌글리콜디프로필에테르, 디에틸렌글리콜디부틸에테르 등의 디에틸렌글리콜디알킬에테르류; 메틸셀로솔브아세테이트, 에틸셀로솔브아세테이트, 에틸렌글리콜모노부틸에테르아세테이트, 에틸렌글리콜모노에틸에테르아세테이트 등의 에틸렌글리콜알킬에테르아세테이트류; 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트, 메톡시부틸아세테이트, 메톡시펜틸아세테이트 등의 알킬렌글리콜알킬에테르아세테이트류; 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르 등의 프로필렌글리콜모노알킬에테르류; 프로필렌글리콜디메틸에테르, 프로필렌글리콜디에틸에테르, 프로필렌글리콜에틸메틸에테르, 프로필렌글리콜디프로필에테르프로필렌글리콜프로필메틸에테르, 프로필렌글리콜에틸프로필에테르 등의 프로필렌글리콜디알킬에테르류; 프로필렌글리콜메틸에테르프로피오네이트, 프로필렌글리콜에틸에테르프로피오네이트, 프로필렌글리콜프로필에테르프로피오네이트, 프로필렌글리콜부틸에테르프로피오네이트 등의 프로필렌글리콜알킬에테르프로피오네이트류; 메톡시부틸알코올, 에톡시부틸알코올, 프로폭시부틸알코올, 부톡시부틸알코올 등의 부틸디올모노알킬에테르류; 메톡시부틸아세테이트, 에톡시부틸아세테이트, 프로폭시부틸아세테이트, 부톡시부틸아세테이트 등의 부탄디올모노알킬에테르아세테이트류; 메톡시부틸프로피오네이트, 에톡시부틸프로피오네이트, 프로폭시부틸프로피오네이트, 부톡시부틸프로피오네이트 등의 부탄디올모노알킬에테르프로피오네이트류; 디프로필렌글리콜디메틸에테르, 디프로필렌글리콜디에틸에테르, 디프로필렌글리콜메틸에틸에테르 등의 디프로필렌글리콜디알킬에테르류; 벤젠, 톨루엔, 자일렌, 메시틸렌 등의 방향족 탄화수소류; 메틸에틸케톤, 아세톤, 메틸아밀케톤, 메틸이소부틸케톤, 시클로헥사논 등의 케톤류; 에탄올, 프로판올, 부탄올, 헥산올, 시클로헥산올, 에틸렌글리콜, 글리세린 등의 알코올류; 아세트산메틸, 아세트산에틸, 아세트산프로필, 아세트산부틸, 2-히드록시프로피온산에틸, 2-히드록시-2-메틸프로피온산메틸, 2-히드록시-2-메틸프로피온산에틸, 히드록시아세트산메틸, 히드록시아세트산에틸, 히드록시아세트산부틸, 락트산메틸, 락트산에틸, 락트산프로필, 락트산부틸, 3-히드록시프로피온산메틸, 3-히드록시프로피온산에틸, 3-히드록시프로피온산프로필, 3-히드록시프로피온산부틸, 2-히드록시-3-메틸부탄산메틸, 메톡시아세트산메틸, 메톡시아세트산에틸, 메톡시아세트산프로필, 메톡시아세트산부틸, 에톡시아세트산메틸, 에톡시아세트산에틸, 에톡시아세트산프로필, 에톡시아세트산부틸, 프로폭시아세트산메틸, 프로폭시아세트산에틸, 프로폭시아세트산프로필, 프로폭시아세트산부틸, 부톡시아세트산메틸, 부톡시아세트산에틸, 부톡시아세트산프로필, 부톡시아세트산부틸, 2-메톡시프로피온산메틸, 2-메톡시프로피온산에틸, 2-메톡시프로피온산프로필, 2-메톡시프로피온산부틸, 2-에톡시프로피온산메틸, 2-에톡시프로피온산에틸, 2-에톡시프로피온산프로필, 2-에톡시프로피온산부틸, 2-부톡시프로피온산메틸, 2-부톡시프로피온산에틸, 2-부톡시프로피온산프로필, 2-부톡시프로피온산부틸, 3-메톡시프로피온산메틸, 3-메톡시프로피온산에틸, 3-메톡시프로피온산프로필, 3-메톡시프로피온산부틸, 3-에톡시프로피온산메틸, 3-에톡시프로피온산에틸, 3-에톡시프로피온산프로필, 3-에톡시프로피온산부틸, 3-프로폭시프로피온산메틸, 3-프로폭시프로피온산에틸, 3-프로폭시프로피온산프로필, 3-프로폭시프로피온산부틸, 3-부톡시프로피온산메틸, 3-부톡시프로피온산에틸, 3-부톡시프로피온산프로필, 3-부톡시프로피온산부틸 등의 에스테르류; 테트라히드로푸란, 피란 등의 고리형 에테르류; γ-부티로락톤 등의 고리형 에스테르류 등을 들 수 있다. 여기서 예시한 용제는, 각각 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. Specific examples of the solvent include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol monobutyl ether acetate, and ethylene glycol monoethyl ether acetate; Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether; propylene glycol dialkyl ethers such as propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol ethyl methyl ether, propylene glycol dipropyl ether, propylene glycol propyl methyl ether, and propylene glycol ethyl propyl ether; propylene glycol alkyl ether propionates such as propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate, and propylene glycol butyl ether propionate; Butyldiol monoalkyl ethers such as methoxybutyl alcohol, ethoxybutyl alcohol, propoxybutyl alcohol, and butoxybutyl alcohol; Butanediol monoalkyl ether acetates such as methoxybutyl acetate, ethoxybutyl acetate, propoxybutyl acetate, and butoxybutyl acetate; butanediol monoalkyl ether propionates such as methoxybutylpropionate, ethoxybutylpropionate, propoxybutylpropionate, and butoxybutylpropionate; Dipropylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, and dipropylene glycol methyl ethyl ether; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin; Methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl hydroxyacetate, ethyl hydroxyacetate. , Butyl hydroxyacetate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, propyl 3-hydroxypropionate, butyl 3-hydroxypropionate, 2-hydroxy -3-Methyl butanoate, methyl methoxyacetate, ethyl methoxyacetate, propyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, propyl ethoxyacetate, butyl ethoxyacetate, propoxy Methyl acetate, ethyl propoxyacetate, propyl propoxyacetate, butyl propoxyacetate, methyl butoxyacetate, ethyl butoxyacetate, propyl butoxyacetate, butyl butoxyacetate, methyl 2-methoxypropionate, 2-methoxypropionic acid. Ethyl, 2-methoxypropionate, butyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-ethoxypropionate, butyl 2-ethoxypropionate, methyl 2-butoxypropionate. , 2-butoxyethyl propionate, 2-butoxypropyl propionate, butyl 2-butoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-methoxypropyl propionate, butyl 3-methoxypropionate, 3-ethoxymethyl propionate, ethyl 3-ethoxypropionate, 3-ethoxypropyl propionate, 3-ethoxybutyl propionate, methyl 3-propoxypropionate, ethyl 3-propoxypropionate, 3-propoxypropionate, 3 -Esters such as butyl propoxypropionate, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, 3-butoxypropyl propionate, and butyl 3-butoxypropionate; Cyclic ethers such as tetrahydrofuran and pyran; Cyclic esters such as γ-butyrolactone, etc. can be mentioned. The solvents exemplified here can be used individually or in mixture of two or more types.
상기 용제는 도포성 및 건조성을 고려하였을 때 알킬렌글리콜알킬에테르아세테이트류, 케톤류, 부탄디올알킬에테르아세테이트류, 부탄디올모노알킬에테르류, 3-에톡시프로피온산에틸, 3-메톡시프로피온산메틸 등의 에스테르류가 바람직하게 사용될 수 있으며, 더욱 바람직하게는 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 시클로헥사논, 메톡시부틸아세테이트, 메톡시부탄올, 3-에톡시프로피온산에틸, 3-메톡시프로피온산메틸 등이 사용될 수 있다. When considering applicability and drying properties, the solvent is esters such as alkylene glycol alkyl ether acetates, ketones, butanediol alkyl ether acetates, butanediol monoalkyl ethers, ethyl 3-ethoxypropionate, and methyl 3-methoxypropionate. Can be preferably used, more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, methoxybutyl acetate, methoxybutanol, ethyl 3-ethoxypropionate, 3-methoxypropionic acid. Methyl, etc. may be used.
상기 용제의 함유량은 그것을 포함하는 열경화성 수지 조성물 전체 100 중량부에 대하여 40 내지 90 중량부, 바람직하게는 45 내지 85 중량부로 포함될 수 있다. 상기 용제의 함유량이 상기 범위에 있으면, 스핀 코터, 슬릿 & 스핀 코터, 슬릿 코터(다이 코터, 커튼플로우 코터라고도 불리는 경우가 있다), 잉크젯 등의 도포 장치로 도포했을 때 도포성이 양호해지기 때문에 바람직하다.The content of the solvent may be 40 to 90 parts by weight, preferably 45 to 85 parts by weight, based on 100 parts by weight of the thermosetting resin composition containing it. If the content of the solvent is in the above range, the applicability becomes good when applied with a coating device such as a spin coater, slit & spin coater, slit coater (sometimes called a die coater, curtain flow coater), or inkjet. desirable.
본 발명에 따른 경화성 수지 조성물은 본 발명의 목적을 저해하지 않는 범위에서 필요에 따라 충진제, 다른 고분자 화합물, 경화제, 레벨링제, 밀착성 개선제, 산화 방지제, 라디컬 발생제, 슬립성 개선제, 응집 방지제, 연쇄 이동제 등의 첨가제를 더 포함할 수 있다. The curable resin composition according to the present invention may contain fillers, other polymer compounds, curing agents, leveling agents, adhesion improvers, antioxidants, radical generators, slip improvers, anti-aggregation agents, It may further contain additives such as chain transfer agents.
상기 충진제의 구체적인 예로는, 유리, 실리카, 알루미나 등을 들 수 있다.Specific examples of the filler include glass, silica, alumina, etc.
상기 다른 고분자 화합물의 구체적인 예로는, 에폭시 수지, 말레이미드 수지 등의 경화성 수지; 폴리비닐알코올, 폴리아크릴산, 폴리에틸렌글리콜모노알킬에테르, 폴리플루오로알킬아크릴레이트, 폴리에스테르, 폴리우레탄 등의 열가소성 수지 등을 들 수 있다.Specific examples of the other polymer compounds include curable resins such as epoxy resins and maleimide resins; Thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane can be mentioned.
상기 경화제는 심부 경화 및 기계적 강도를 높이기 위해 사용되며, 경화제의 구체적인 예로서는 에폭시 화합물, 다관능 이소시아네이트 화합물, 멜라민 화합물, 옥세탄 화합물 등을 들 수 있다. The curing agent is used to improve deep hardening and mechanical strength, and specific examples of the curing agent include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.
상기 경화제에서 에폭시 화합물의 구체적인 예로서는 비스페놀 A계 에폭시 수지, 수소화 비스페놀 A계 에폭시 수지, 비스페놀 F계 에폭시 수지, 수소화 비스페놀 F계 에폭시 수지, 노블락형 에폭시 수지, 기타 방향족계 에폭시 수지, 지환족계 에폭시 수지, 글리시딜에스테르계 수지, 글리시딜아민계 수지, 또는 이러한 에폭시 수지의 브롬화 유도체, 에폭시 수지 및 그 브롬화 유도체 이외의 지방족, 지환족 또는 방향족 에폭시 화합물, 부타디엔 (공)중합체 에폭시화물, 이소프렌 (공)중합체 에폭시화물, 글리시딜(메타)아크릴레이트 (공)중합체, 트리글리시딜이소시아누레이트 등을 들 수 있다. Specific examples of the epoxy compound in the curing agent include bisphenol A-based epoxy resin, hydrogenated bisphenol A-based epoxy resin, bisphenol F-based epoxy resin, hydrogenated bisphenol F-based epoxy resin, noblock-type epoxy resin, other aromatic epoxy resins, cycloaliphatic epoxy resin, Glycidyl ester resin, glycidylamine resin, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof, butadiene (co)polymer epoxide, isoprene (co) ) Polymer epoxide, glycidyl (meth)acrylate (co)polymer, triglycidyl isocyanurate, etc.
상기 경화제에서 옥세탄 화합물의 구체적인 예로서는 카르보네이트비스옥세탄, 크실렌비스옥세탄, 아디페이트비스옥세탄, 테레프탈레이트비스옥세탄, 시클로헥산디카르복실산비스옥세탄 등을 들 수 있다. Specific examples of the oxetane compound in the curing agent include carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane.
상기 경화제는 경화제와 함께 에폭시 화합물의 에폭시기, 옥세탄 화합물의 옥세탄 골격을 개환 중합하게 할 수 있는 경화 보조 화합물을 병용할 수 있다. 상기 경화 보조 화합물로서는, 예를 들면 다가 카르본산류, 다가 카르본산 무수물류, 산 발생제 등을 들 수 있다. The curing agent may be used in combination with a curing auxiliary compound that can cause ring-opening polymerization of the epoxy group of an epoxy compound and the oxetane skeleton of an oxetane compound. Examples of the curing auxiliary compound include polyhydric carboxylic acids, polyhydric carboxylic anhydrides, and acid generators.
상기 카르본산 무수물류는 에폭시 수지 경화제로서 시판되는 것을 이용할 수 있다. 상기 에폭시 수지 경화제로서는, 예를 들면, 상품명(아데카하도나 EH-700)(아데카공업㈜ 제조), 상품명(리카싯도 HH)(신일본이화㈜ 제조), 상품명(MH-700)(신일본이화㈜ 제조) 등을 들 수 있다. 상기에서 예시한 경화제는 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. The carboxylic acid anhydride can be used as a commercially available epoxy resin curing agent. Examples of the epoxy resin curing agent include brand name (Adeka Hadona EH-700) (made by Adeka Kogyo Co., Ltd.), brand name (Rika Siddo HH) (made by Nippon Ewha Co., Ltd.), and brand name (MH-700) ( (manufactured by Nippon E-Hwa Co., Ltd.), etc. can be mentioned. The curing agents exemplified above can be used individually or in combination of two or more types.
상기 레벨링제로는, 시판되는 계면 활성제를 사용할 수 있고, 예를 들어 실리콘계, 불소계, 에스테르계, 양이온계, 음이온계, 비이온계, 양성 등의 계면 활성제 등을 들 수 있고, 이들은 각각 단독으로도 2 종 이상을 조합하여 사용해도 된다. As the leveling agent, commercially available surfactants can be used, for example, silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, etc. surfactants, and these can be used alone. Two or more types may be used in combination.
상기 계면 활성제로는, 예를 들어 폴리옥시에틸렌알킬에테르류, 폴리옥시에틸렌알킬페닐에테르류, 폴리에틸렌글리콜디에스테르류, 소르비탄지방산 에스테르류, 지방산 변성 폴리에스테르류, 3 급 아민 변성 폴리우레탄류, 폴리에틸렌이민류 등 외에, 상품명으로 KP (신에쯔 화학 공업 (주) 제조), 폴리플로우 (쿄에이 화학(주) 제조), 에프톱 (토켐프로덕츠사 제조), 메가팍 (다이닛폰 잉크 화학 공업 (주) 제조), 플로라드 (스미토모쓰리엠 (주) 제조), 아사히가드, 사프론 (이상, 아사히가라스 (주) 제조), 소르스파스 (제네카 (주) 제조), EFKA (EFKA CHEMICALS 사 제조), PB821 (아지노모토 (주) 제조), SH-8400 (DOW chemical 제조) 등을 들 수 있다.Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, In addition to polyethylene imines, etc., brand names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoei Chemical Co., Ltd.), F-Top (manufactured by Tochem Products Co., Ltd.), and Megapak (Dainippon Ink Chemical Co., Ltd.) (manufactured by Sumitomo 3M Co., Ltd.), Florad (manufactured by Sumitomo 3M Co., Ltd.), Asahi Guard, Saffron (above, manufactured by Asahi Glass Co., Ltd.), Solspas (manufactured by Zeneca Co., Ltd.), EFKA (EFKA CHEMICALS Co., Ltd.) manufactured by), PB821 (manufactured by Ajinomoto Co., Ltd.), SH-8400 (manufactured by DOW Chemical), etc.
상기 밀착성 개선제로는, 실란계 화합물이 바람직하고, 구체적으로는, 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리스(2-메톡시에톡시)실란, N-(2-아미노에틸)-3-아미노프로필메틸디메톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란, 3-아미노프로필트리에톡시실란, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필메틸디메톡시실란, 2-(3,4-에폭시시클로헥실)에틸트리메톡시실란, 3-클로로프로필메틸디메톡시실란, 3-클로로프로필트리메톡시실란, 3-메타크릴로일옥시프로필트리메톡시실란, 3-메르캅토프로필트리메톡시실란 등을 들 수 있으며, 시판품으로는 KBE-9007 (Shin-Etsu) 등을 사용할 수 있으나 이에 한정되지는 않는다.As the adhesion improving agent, silane-based compounds are preferable, and specifically, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)- 3-Aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-gly Sidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxy Propyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. can be used, and commercial products such as KBE-9007 (Shin-Etsu) can be used, but are not limited thereto.
상기 산화 방지제로는 구체적으로, 2-tert-부틸-6-(3-tert-부틸-2-히드록시-5-메틸벤질)-4-메틸페닐아크릴레이트, 2-[1-(2-히드록시-3,5-디-tert-펜틸페닐)에틸]-4,6-디-tert-펜틸페닐아크릴레이트, 6-[3-(3-tert-부틸-4-히드록시-5-메틸페닐)프로폭시]-2,4,8,10-테트라-tert-부틸디벤즈[d,f][1,3,2]디옥사포스페핀, 3,9-비스[2-{3-(3-tert-부틸-4-히드록시-5-메틸페닐)프로피오닐옥시}-1,1-디메틸에틸]-2,4,8,10-테트라옥사스피로[5.5]운데칸, 2,2'-메틸렌비스(6-tert-부틸-4-메틸페놀), 4,4'-부틸리덴비스(6-tert-부틸-3-메틸페놀), 4,4'-티오비스(2-tert-부틸-5-메틸페놀), 2,2'-티오비스(6-tert-부틸-4-메틸페놀), 디라우릴 3,3'-티오디프로피오네이트, 디미리스틸 3,3'-티오디프로피오네이트, 디스테아릴 3,3'-티오디프로피오네이트, 펜타에리트리틸테트라키스(3-라우릴티오프로피오네이트), 1,3,5-트리스(3,5-디-tert-부틸-4-히드록시벤질)-1,3,5-트리아진-2,4,6(1H,3H,5H)-트리온, 3,3',3'',5,5',5''-헥사-tert-부틸-a,a',a''-(메시틸렌-2,4,6-트리일)트리-p-크레졸, 펜타에리트리톨테트라키스[3-(3,5-디-tert-부틸-4-히드록시페닐)프로피오네이트], 2,6-디-tert-부틸-4-메틸페놀 등을 들 수 있다.Specifically, the antioxidant includes 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenylacrylate, 2-[1-(2-hydroxy -3,5-di-tert-pentylphenyl)ethyl]-4,6-di-tert-pentylphenylacrylate, 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)prop Poxy]-2,4,8,10-tetra-tert-butyldibenz[d,f][1,3,2]dioxaphosphepine, 3,9-bis[2-{3-(3-tert -Butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 2,2'-methylenebis( 6-tert-butyl-4-methylphenol), 4,4'-butylidenebis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(2-tert-butyl-5- methylphenol), 2,2'-thiobis(6-tert-butyl-4-methylphenol), dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate , distearyl 3,3'-thiodipropionate, pentaerythrityl tetrakis (3-lauryl thiopropionate), 1,3,5-tris (3,5-di-tert-butyl- 4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 3,3',3'',5,5',5''- Hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl)tri-p-cresol, pentaerythritol tetrakis[3-(3,5-di-tert -butyl-4-hydroxyphenyl)propionate], 2,6-di-tert-butyl-4-methylphenol, etc.
상기 라디컬 발생제로서는 예를 들면, 벤조인계 화합물, 벤조페논계 화합물, 티옥산톤계 화합물, 트리아진계 화합물등을 들 수 있다. 벤조인계 화합물로는, 예를 들면, 벤조인, 벤조인메틸에테르, 벤조인에틸에테르, 벤조인이소프로필에테르, 벤조이소부틸에테르 등을 들 수 있다. 벤조페논계 화합물로는, 예를 들면, 벤조페논, o-벤조일벤조산메틸, 4-페닐조페논, 4-벤조일-4'-메틸디페닐설파이드, 3,3',4,4'-테트라(t-부틸퍼옥시카보닐)벤조페논, 2,4,6-트리메틸벤조페논 등을 들 수 있다. 티옥산톤계 화합물로는, 예를 들면, 2-이소프로필티옥산톤, 4-이소프로필티옥산톤, 2,4-디에틸티옥산톤, 2,4-디클로로티옥산톤, 1-클로로-4-프로폭시티옥산톤 등을 들 수 있다. 트리아진계 화합물로는, 예를 들면, 2,4-비스(트리클로로메틸)-6-(4-메톡시페닐)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시나프틸)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시스티릴)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(5-메틸퓨란-2-일)에테닐]-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(퓨란-2-일)에테닐]-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-[2-(4-디에틸아미노-2-메틸페닐)에테닐]-1,3,5-트리아진,2,4-비스(트리클로로메틸)-6-[2-(3,4디메톡시페닐)에테닐]-1,3,5-트리아진 등을 들 수 있다. 옥심계 화합물로는 예을 들면, o-에톡시카르보닐-α-옥시이미노-1-페닐프로판-1-온 등을 들 수 있으며, 시판품으로 바스프사의 OXE01, OXE02가 대표적이다.Examples of the radical generator include benzoin-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and triazine-based compounds. Examples of benzoin-based compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoisobutyl ether. Examples of benzophenone-based compounds include benzophenone, o-benzoylmethyl benzoate, 4-phenylzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 3,3',4,4'-tetra ( t-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned. Thioxanthone-based compounds include, for example, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro- 4-propoxythioxanthone, etc. can be mentioned. Triazine-based compounds include, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) -6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-tri Azine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl )-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino- 2-methylphenyl)ethenyl]-1,3,5-triazine,2,4-bis(trichloromethyl)-6-[2-(3,4dimethoxyphenyl)ethenyl]-1,3,5 -Triazine, etc. can be mentioned. Oxime-based compounds include, for example, o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, and commercially available products include OXE01 and OXE02 from BASF.
상기 슬립성 개선제는 식물기반의 지방산 유도체, 시판품으로서 BYK-333(BYK) 등을 사용할 수 있으나, 이에 한정되지는 않는다.The slip improvement agent may be a plant-based fatty acid derivative or a commercially available product such as BYK-333 (BYK), but is not limited thereto.
상기 자외선 흡수제로서 구체적으로는, 2-(3-tert-부틸-2-히드록시-5-메틸페닐)-5-클로로벤조트리아졸, 알콕시벤조페논 등을 들 수 있다.Specific examples of the ultraviolet absorber include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, alkoxybenzophenone, and the like.
상기 응집 방지제로는, 구체적으로는, 폴리아크릴산 나트륨 등을 들 수 있다.Specific examples of the anti-agglomeration agent include sodium polyacrylate.
상기 연쇄 이동제로는, 구체적으로 도데실메르캅탄, 2,4-디페닐-4-메틸-1-펜텐 등을 들 수 있다.Specific examples of the chain transfer agent include dodecyl mercaptan, 2,4-diphenyl-4-methyl-1-pentene, and the like.
상기 첨가제는 본 발명의 목적을 저해하지 않는 범위에서 적절히 첨가하여 사용할 수 있으며, 예컨대 상기 열경화성 수지 조성물 전체 100 중량부에 대하여 0.05 내지 10 중량부, 바람직하게는 0.05 내지 5 중량부, 더욱 바람직하게는 0.1 내지 3 중량부로 사용할 수 있으나 이에 한정되지는 않는다.The additives may be appropriately added and used within the range that does not impair the purpose of the present invention, for example, 0.05 to 10 parts by weight, preferably 0.05 to 5 parts by weight, more preferably 0.05 to 5 parts by weight, based on 100 parts by weight of the total thermosetting resin composition. It can be used in an amount of 0.1 to 3 parts by weight, but is not limited thereto.
본 발명의 열경화성 수지 조성물은, 예를 들어 용제에 바인더 수지, 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트, 용제 및 필요에 따라 사용되는 그 밖의 기타 첨가제를 첨가 혼합하는 방법에 의해 제조될 수 있다. 그러나 본 발명이 이러한 방법을 한정하는 것은 아니다.The thermosetting resin composition of the present invention can be prepared, for example, by adding and mixing a binder resin, a polyfunctional urethane acrylate containing a cyclic linking group, a solvent, and other additives used as needed in a solvent. . However, the present invention is not limited to this method.
<< 경화막cured film >>
본 발명의 다른 양태는 전술한 열경화성 수지 조성물의 경화물을 포함하는 경화막에 관한 것이다.Another aspect of the present invention relates to a cured film comprising a cured product of the above-described thermosetting resin composition.
본 발명에 따르면 상기한 열경화성 수지 조성물을 기재 상에 도포한 후 열을 가해 도막을 제조 할 수 있다.According to the present invention, a coating film can be manufactured by applying heat to the substrate after applying the thermosetting resin composition described above.
제조 과정의 바람직한 예를 들자면, 열경화성 수지 조성물을 기판(통상은 유리) 또는 먼저 형성된 수지 조성물의 고형분으로 이루어지는 층 상에 도포한 후 가열건조함으로써 용제 등의 휘발 성분을 제거하여 평활한 도막을 얻을 수 있다. To give a preferred example of the manufacturing process, the thermosetting resin composition is applied on a substrate (usually glass) or a layer made of the solid content of the previously formed resin composition, and then heated and dried to remove volatile components such as solvents to obtain a smooth coating film. there is.
도포 방법으로는, 예를 들어 스핀 코트, 유연 도포법, 롤 도포법, 슬릿 앤드 스핀 코트 또는 슬릿 코트법 등에 의해 실시될 수 있다. The application method may be, for example, spin coating, flexible coating, roll coating, slit and spin coating, or slit coating.
도포 후 가열 건조 (프리베이크), 또는 감압 건조 후에 가열하여 용제 등의 휘발 성분을 휘발시킨다. 여기에서, 가열 온도는 통상 70∼200℃, 바람직하게는 80∼130℃이다. 가열 건조 후의 도막 두께는 통상 1∼8㎛ 정도이다. 이후 상온으로 냉각 시킨 후 경화 네트워크 형성을 위해 다시 가열 과정을 진행한다(포스트베이크). 여기에서, 가열 온도는 통상 150~230℃, 바람직하게는 170~200℃이다. 가열 방법으로는 핫플레이트나 클린오븐 적외선 히터 등을 사용할 수 있다. 하지만 본 발명이 가열 방법을 한정하는 것은 아니다.After application, it is heated and dried (prebake), or dried under reduced pressure and then heated to volatilize volatile components such as solvents. Here, the heating temperature is usually 70 to 200°C, preferably 80 to 130°C. The thickness of the coating film after heat drying is usually about 1 to 8 μm. Afterwards, it is cooled to room temperature and then heated again to form a hardened network (post-bake). Here, the heating temperature is usually 150 to 230°C, preferably 170 to 200°C. As a heating method, a hot plate or clean oven infrared heater can be used. However, the present invention does not limit the heating method.
본 발명의 열경화성 수지 조성물을 사용하고, 이상과 같은 각 공정을 거쳐 기판 상 혹은 하부 기재 상에 유기 보호막을 형성할 수 있다. Using the thermosetting resin composition of the present invention, an organic protective film can be formed on a substrate or a lower substrate through each of the above processes.
따라서, 이렇게 해서 얻어지는 경화막은 보호막으로서 액정 표시 장치 등의 표시 장치에 유용하게 사용될 수 있으며, 특히 도막의 높은 경도와 스크래치 방지로 특성으로 인해 오버코트층으로서 유용하게 사용할 수 있다.Therefore, the cured film obtained in this way can be usefully used as a protective film in display devices such as liquid crystal displays, and in particular, can be usefully used as an overcoat layer due to the high hardness and anti-scratch characteristics of the coating film.
본 발명의 또 다른 실시형태에 있어서, 상기 경화막은 오버코트층일 수 있다.In another embodiment of the present invention, the cured film may be an overcoat layer.
구체적으로, 본 발명에 따른 경화막은 하이드록시알킬(메트)아크릴레이트 유래의 반복단위, 지환족 고리형 에폭시기를 함유하는 (메트)아크릴레이트 유래의 반복단위 및 불포화 카르복실산 유래의 반복단위를 포함하는 바인더 수지; 및 고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트;를 포함하는 열경화성 수지 조성물을 이용하여 제조되었기 때문에 하부 기판 또는 하부 기재와의 밀착성 및 신뢰성 우수하고, 경도가 우수할 뿐 아니라, 백화 현상이 억제되는 이점이 있다.Specifically, the cured film according to the present invention includes a repeating unit derived from hydroxyalkyl (meth)acrylate, a repeating unit derived from (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from unsaturated carboxylic acid. binder resin; and polyfunctional urethane acrylate containing a cyclic linking group; thus, it has excellent adhesion and reliability to the lower substrate or lower substrate, excellent hardness, and suppresses whitening. There is an advantage.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세히 설명한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지는 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다. 또한, 이하에서 함유량을 나타내는 "%" 및 "부"는 특별히 언급하지 않는 한 중량 기준이다.Hereinafter, examples will be given in detail to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described in detail below. The embodiments of this specification are provided to more completely explain the present specification to those with average knowledge in the art. In addition, "%" and "part" indicating content below are based on weight, unless otherwise specified.
합성예Synthesis example 1: 바인더 수지(A-1) 1: Binder resin (A-1)
환류 냉각기, 적하 깔대기 및 교반기를 구비한 1L의 플라스크 내에 질소를 0.02L/분으로 흐르게 하여 질소 분위기로 하고, 디에틸렌글리콜 메틸에틸에테르 150g을 넣고 교반하면서 70℃까지 가열하였다. Nitrogen was flowed at 0.02 L/min into a 1 L flask equipped with a reflux condenser, dropping funnel, and stirrer to create a nitrogen atmosphere. 150 g of diethylene glycol methyl ethyl ether was added and heated to 70°C while stirring.
[화학식 6] [화학식 7][Formula 6] [Formula 7]
이어서, 화학식 6 및 화학식 7의 혼합물(몰비는 50:50) 132.2g(0.60mol), 3-에틸-3-옥세타닐 메타크릴레이트 55.3g(0.30mol) 및 메타크릴산 8.6g(0.10mol)을 첨가하여 합성을 진행하여, 고형분 41.6 질량% 산가 61mgKOH/g (고형분 환산)의 공중합체 수지 A-1의 용액을 얻었다. 얻어진 수지 A-1의 중량 평균 분자량 Mw는 7,850, 분자량 분포는 1.85였다. Then, 132.2 g (0.60 mol) of the mixture of Formula 6 and Formula 7 (molar ratio 50:50), 55.3 g (0.30 mol) of 3-ethyl-3-oxetanyl methacrylate, and 8.6 g (0.10 mol) of methacrylic acid. ) was added to proceed with the synthesis to obtain a solution of copolymer resin A-1 with a solid content of 41.6 mass% and an acid value of 61 mgKOH/g (converted to solid content). The weight average molecular weight Mw of the obtained resin A-1 was 7,850, and the molecular weight distribution was 1.85.
이때, 상기 분산수지의 중량평균 분자량(Mw) 및 수평균 분자량(Mn) )의 측정은 HLC-8120GPC(도소㈜ 제조) 장치를 사용하였으며, 칼럼은 TSK-GELG4000HXL와 TSK-GELG2000HXL를 직렬 접속하여 사용하였고, 칼럼 온도는 40℃, 이동상 용매는 테트라히드로퓨란, 유속은 1.0㎖/분, 주입량은 50㎕, 검출기 RI를 사용하였으며, 측정 시료 농도는 0.6질량%(용매 = 테트라히드로퓨란), 교정용 표준 물질은 TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500(도소㈜ 제조)을 사용하였다.At this time, the weight average molecular weight (Mw) and number average molecular weight (Mn) of the dispersion resin were measured using an HLC-8120GPC (manufactured by Tosoh Co., Ltd.) device, and the column was used by connecting TSK-GELG4000HXL and TSK-GELG2000HXL in series. The column temperature was 40°C, the mobile phase solvent was tetrahydrofuran, the flow rate was 1.0 ㎖/min, the injection volume was 50㎕, the detector RI was used, and the measured sample concentration was 0.6% by mass (solvent = tetrahydrofuran), for calibration. TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, and A-500 (manufactured by Tosoh Co., Ltd.) were used as standard materials.
상기에서 얻어진 중량평균분자량 및 수평균분자량의 비를 분자량 분포 (Mw/Mn)로 하였으며, 얻어진 바인더 수지(A-1)은 하기 화학식 8과 같은 구조이다.The ratio of the weight average molecular weight and the number average molecular weight obtained above was defined as the molecular weight distribution (Mw/Mn), and the obtained binder resin (A-1) had a structure shown in the following formula (8).
[화학식 8] [Formula 8]
합성예Synthesis example 2: 바인더 수지(A-2) 2: Binder resin (A-2)
상기 합성예 1의 바인더 수지(A-1)와 동일한 조건을 적용하여, 하이드록시(메트)아크릴레이트 13.0g(0.1mol), 화학식 6 및 화학식 7의 혼합물(몰비는 50:50) 110.2(0.50mol), 3-에틸-3-옥세타닐 메타크릴레이트 55.3g(0.30mol) 및 메타크릴산 8.6g(0.10mol)을 첨가하여 합성을 진행하여, 고형분 36.5 질량%, 산가 62㎎-KOH/g (고형분 환산)의 공중합체 (수지 A-2)의 용액을 얻었다. 얻어진 수지 A-2의 중량 평균 분자량 Mw는 7,720, 분자량 분포는 1.71이었으며, 얻어진 바인더 수지 A-2는 하기 화학식 9와 같은 구조이다.Applying the same conditions as the binder resin (A-1) of Synthesis Example 1, 13.0 g (0.1 mol) of hydroxy (meth)acrylate, a mixture of Formula 6 and Formula 7 (molar ratio 50:50) 110.2 (0.50) mol), 55.3 g (0.30 mol) of 3-ethyl-3-oxetanyl methacrylate, and 8.6 g (0.10 mol) of methacrylic acid were added to proceed with the synthesis, resulting in a solid content of 36.5% by mass and an acid value of 62 mg-KOH/ A solution of g (in terms of solid content) of the copolymer (Resin A-2) was obtained. The weight average molecular weight Mw of the obtained resin A-2 was 7,720 and the molecular weight distribution was 1.71, and the obtained binder resin A-2 had a structure shown in the following formula (9).
[화학식 9][Formula 9]
실시예Example 및 and 비교예Comparative example : 열경화성 수지 조성물의 제조: Preparation of thermosetting resin composition
하기 표 1에 따른 구성 및 조성으로 실시예 및 비교예에 따른 열경화성 수지 조성물(단위: 중량부)을 제조하였다.Thermosetting resin compositions (unit: parts by weight) according to Examples and Comparative Examples were prepared with the composition and composition according to Table 1 below.
(B-1) 관능기 수: 10개, 중량평균분자량: 500-1300 (Shin nakamura사, U-10PA)(B-1) Number of functional groups: 10, weight average molecular weight: 500-1300 (Shin nakamura, U-10PA)
(B-2) 관능기 수: 10개, 중량평균분자량: 500-1200 (Shin nakamura사, U-10HA)(B-2) Number of functional groups: 10, weight average molecular weight: 500-1200 (Shin nakamura, U-10HA)
(B-3) 관능기수: 15, 중량평균분자량: 2100-2500 (Shin nakamura사, U-15HA)(B-3) Number of functional groups: 15, weight average molecular weight: 2100-2500 (Shin nakamura, U-15HA)
(C-1): 프로필렌글리콜모노메틸에테르아세테이트 (KH Neo-chem, PGMEA)(C-1): Propylene glycol monomethyl ether acetate (KH Neo-chem, PGMEA)
(C-2): 다이에틸렌글리콜메틸에틸에테르 (한농화성, MEDG)(C-2): Diethylene glycol methyl ethyl ether (Hanong Chemical, MEDG)
(D-1): 레벨링제(SH-8400 (DOW chemical))(D-1): Leveling agent (SH-8400 (DOW chemical))
(D-2): 슬립성 개선제(BYK-333 (BYK))(D-2): Slip improvement agent (BYK-333 (BYK))
(D-3): 라디컬 발생제(Irgacure OXE01 (BASF))(D-3): Radical generator (Irgacure OXE01 (BASF))
(D-4): 밀착성 개선제(KBE-9007 (Shin-Etsu))(D-4): Adhesion improver (KBE-9007 (Shin-Etsu))
실험예Experiment example
가로, 세로 2인치의 유리 기판(이글 2000; 코닝사 제조)을 중성 세제, 물 및 알코올로 순차 세정한 후 건조하였다. 이 유리 기판 상에 상기 실시예 및 비교예에서 제조된 열경화성 수지 조성물을 각각 스핀 코팅한 다음 잔존용매를 휘발시키기 위해 진공건조기에서 66Pa로 건조하였다. 이후 클린오븐 중에서 100℃에서 3 분간 프리베이크하였다. 상기 프리베이크한 기판을 상온으로 냉각 후 다시 클린오븐 중에서 180℃에서 30 분간 포스트베이크 하였다. 이 때 얻어진 막두께는 3㎛이었다. 막두께는 막두께 측정장치(DEKTAK 6M; Veeco사 제조)를 사용하여 측정하였다. 이렇게 얻어진 패턴을 아래와 같이 물성 평가를 실시하고, 그 결과를 하기 표 2에 나타내었다. A glass substrate measuring 2 inches wide and 2 inches long (Eagle 2000; manufactured by Corning) was sequentially washed with neutral detergent, water, and alcohol and then dried. The thermosetting resin compositions prepared in Examples and Comparative Examples were spin-coated on this glass substrate and then dried in a vacuum dryer at 66 Pa to volatilize the remaining solvent. Afterwards, it was prebaked at 100°C for 3 minutes in a clean oven. The prebaked substrate was cooled to room temperature and then post-baked at 180°C for 30 minutes in a clean oven. The film thickness obtained at this time was 3㎛. The film thickness was measured using a film thickness measuring device (DEKTAK 6M; manufactured by Veeco). The pattern obtained in this way was evaluated for physical properties as follows, and the results are shown in Table 2 below.
연필 경도 평가Pencil hardness evaluation
상기에서 얻은 경화된 도막에 대해서, JIS K5600: 1999에 준거한 방법(하중 1kg)으로 연필 경도 시험을 행하고, 측정된 막의 경도가 6H 이상일 경우 '○', 4~5H일 경우 '△', 4H 미만 일 경우 '×'로 표기하였다.For the cured coating film obtained above, a pencil hardness test was performed using a method (load of 1 kg) based on JIS K5600: 1999. If the measured hardness of the film is 6H or more, '○', if it is 4~5H, '△', 4H If it is less than that, it is marked with '×'.
표면 surface 스크래치scratch 평가 evaluation
상기에서 얻은 경화된 도막에 대해서 표면 스크래치 평가는 스틸 울 평가로 진행하였다. 사용한 스틸 울은 #0000s 레벨이며, 1.5kg의 하중을 주었고 분당 60회의 속도로 10회 반복하였다. 평가 후 도막을 암실 조건에서 형광등 불빛에 비추어 긁힌 자국의 개수를 세었으며, 표면에 생긴 스크래치 개수가 20개 미만일 경우 '○', 20~40개 일 경우 '△', 40개 초과일 경우 '×'로 표기하였다.For the cured coating film obtained above, surface scratch evaluation was conducted using steel wool evaluation. The steel wool used was at the #0000s level, and a load of 1.5 kg was applied and repeated 10 times at a speed of 60 times per minute. After evaluation, the number of scratches was counted by illuminating the paint film under fluorescent light in a dark room. If the number of scratches on the surface was less than 20, it was coded as '○', if the number of scratches was between 20 and 40, it was coded as '△', and if it exceeded 40, it was coded as '×'. It is written as '.
밀착성 및 신뢰성 평가 Adhesion and reliability evaluation
상기에서 얻은 경화된 도막에 대한 밀착성 평가로는 크로스 컷 테스트를 진행하여 ASTM Class로 결과값을 표기하였다. 또한 크로스 컷 평가를 받은 도막을 항온항습기에 넣어 습도 85%, 온도 85℃의 조건에서 168 시간 동안 보관하였다. 이후 다시 밀착성 평가를 진행하여 도막의 신뢰성을 평가하였다. 신뢰성에 대한 평가 또한 ASTM Class로 표기하였다.To evaluate the adhesion of the cured coating film obtained above, a cross cut test was performed and the results were expressed in ASTM Class. In addition, the paint film that underwent cross-cut evaluation was placed in a constant temperature and humidity chamber and stored for 168 hours at a humidity of 85% and a temperature of 85°C. Afterwards, adhesion evaluation was performed again to evaluate the reliability of the coating film. Reliability evaluation was also expressed as ASTM Class.
투과율 및 백화 평가Transmittance and whitening evaluation
상기에서 얻은 경화된 도막에 대한 투과율 평가로는 UV-Vis spectrometer를 사용하였으며 450nm에서의 투과율이 99% 이상일 경우 '○', 98~95%일 경우 '△', 95% 미만일 경우 '×'로 표기하였다. 또한 백화평가에 대해서는 육안으로 관측 하였으며 백화가 발생할 경우 '○', 발생하지 않은 경우를 '×'로 표기하였다.A UV-Vis spectrometer was used to evaluate the transmittance of the cured film obtained above. If the transmittance at 450 nm was more than 99%, it was rated as '○', if it was 98-95%, it was coded as '△', and if it was less than 95%, it was coded as '×'. Notated. In addition, the bleaching evaluation was observed with the naked eye, and if bleaching occurred, it was marked as '○', and if it did not occur, it was marked as '×'.
상기 표 2에서 보는 바와 같이 실시예 1과 비교예 2를 비교할 경우 바인더 수지의 함량이 동량일 때 하이드록시에틸메타아크릴레이트를 도입한 바인더 수지가 도입하지 않은 바인더 수지보다 연필경도, 스크래치, 밀착성 및 신뢰성 부분에서 우수한 것을 볼 수 있다. 그리고 실시예 2와 바인더 수지 함량이 동량인 비교예 5 및 비교예 7을 비교해 볼 때 비교예 5, 비교예 7에선 우레탄 아크릴레이트와 바인더 수지간의 상용성이 좋지 않게 되어 포스트베이크 후 백화현상이 나타난 것을 볼 수 있다. 백화현상이 나타난 도막은 투과율이 크게 떨어지게 되어 더 이상 표시재료로서 사용 할 수 없다. 이를 극복하기 위해서는 실시예 1 혹은 실시예 2와 같이 연결기가 고리구조로 되어있는 B-2 우레탄올리고머를 사용해야만 한다. 즉, 본 발명의 경화성 수지 조성물을 사용하면 밀착성 및 신뢰성이 우수하고 동시에 우수한 경도를 가진 유기 보호막을 만들 수 있다.As shown in Table 2, when comparing Example 1 and Comparative Example 2, when the binder resin content is the same, the binder resin containing hydroxyethyl methacrylate has better pencil hardness, scratches, adhesion, and You can see that it is excellent in reliability. And when comparing Example 2 and Comparative Example 5 and Comparative Example 7, which had the same amount of binder resin, the compatibility between urethane acrylate and binder resin was poor in Comparative Example 5 and Comparative Example 7, and whitening occurred after post-baking. You can see that. A coating film that has whitened its transmittance significantly decreases and can no longer be used as a display material. In order to overcome this, B-2 urethane oligomer, which has a ring structure as a linking group as in Example 1 or Example 2, must be used. That is, by using the curable resin composition of the present invention, an organic protective film can be created that has excellent adhesion and reliability and at the same time has excellent hardness.
Claims (12)
고리형 연결기를 함유하는 다관능 우레탄 아크릴레이트;
를 포함하며,
상기 다관능 우레탄 아크릴레이트는 관능기 수가 6 이상인 열경화성 수지 조성물.A binder resin containing a repeating unit derived from a hydroxyalkyl (meth)acrylate, a repeating unit derived from a (meth)acrylate containing an alicyclic cyclic epoxy group, and a repeating unit derived from an unsaturated carboxylic acid; and
Multifunctional urethane acrylate containing a cyclic linking group;
Includes,
The multifunctional urethane acrylate is a thermosetting resin composition having a functional group of 6 or more.
상기 바인더 수지는 옥세탄기를 함유하는 (메트)아크릴레이트 유래의 반복단위를 더 포함하는 것인 열경화성 수지 조성물.According to paragraph 1,
The binder resin is a thermosetting resin composition that further includes a repeating unit derived from (meth)acrylate containing an oxetane group.
상기 바인더 수지는 하기 화학식 3으로 표시되는 것인 열경화성 수지 조성물:
[화학식 3]
(상기 화학식 3에서,
상기 바인더 수지 내,
a는 10 내지 30 mol%이고,
b는 20 내지 60 mol%이고,
c는 5 내지 20 mol%이고,
d는 10 내지 50 mol%이다).According to paragraph 1,
The binder resin is a thermosetting resin composition represented by the following formula (3):
[Formula 3]
(In Formula 3 above,
In the binder resin,
a is 10 to 30 mol%,
b is 20 to 60 mol%,
c is 5 to 20 mol%,
d is 10 to 50 mol%).
상기 다관능 우레탄 아크릴레이트는 2 이상의 우레탄 결합을 함유하고,
1 이상의 메타아크릴로일옥시기를 함유하며,
상기 고리형 연결기는 상기 우레탄 결합간을 연결하는 것인 열경화성 수지 조성물.According to paragraph 1,
The polyfunctional urethane acrylate contains two or more urethane bonds,
Contains one or more methacryloyloxy groups,
The thermosetting resin composition wherein the cyclic linking group connects the urethane bonds.
상기 다관능 우레탄 아크릴레이트는 관능기 수가 10 이상인 것인 열경화성 수지 조성물.According to paragraph 1,
The thermosetting resin composition wherein the multifunctional urethane acrylate has a functional group of 10 or more.
상기 바인더 수지는 상기 열경화성 수지 조성물 전체 100 중량부에 대하여 5 내지 60 중량부로 포함되는 것인 열경화성 수지 조성물.According to paragraph 1,
A thermosetting resin composition in which the binder resin is contained in an amount of 5 to 60 parts by weight based on 100 parts by weight of the total thermosetting resin composition.
상기 다관능 우레탄 아크릴레이트는 상기 열경화성 수지 조성물 전체 100 중량부에 대하여 35 내지 95 중량부로 포함되는 것인 열경화성 수지 조성물.According to paragraph 1,
A thermosetting resin composition in which the multifunctional urethane acrylate is contained in an amount of 35 to 95 parts by weight based on 100 parts by weight of the total thermosetting resin composition.
용제 및 첨가제로 이루어진 군에서 선택되는 1 이상을 더 포함하며,
상기 첨가제는, 충진제, 다른 고분자 화합물, 경화제, 레벨링제, 밀착성 개선제, 산화 방지제, 라디컬 발생제, 슬립성 개선제, 자외선 흡수제, 응집 방지제 및 연쇄 이동제로 이루어진 군에서 선택되는 것인 열경화성 수지 조성물.According to paragraph 1,
It further includes one or more selected from the group consisting of solvents and additives,
The additive is selected from the group consisting of fillers, other polymer compounds, curing agents, leveling agents, adhesion improvers, antioxidants, radical generators, slip improvers, ultraviolet absorbers, agglomeration inhibitors, and chain transfer agents. Thermosetting resin composition.
상기 경화막은 오버코트층인 것인 경화막.According to clause 11,
A cured film wherein the cured film is an overcoat layer.
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JP2008201910A (en) | 2007-02-20 | 2008-09-04 | Jsr Corp | Branched unsaturated polymer, radiosensitive resin composition and spacer for liquid crystal display element |
JP2016056369A (en) | 2014-09-11 | 2016-04-21 | 財團法人工業技術研究院Industrial Technology Research Institute | Hardcoat composition, polarizer, and display device using them |
JP2016204584A (en) | 2015-04-28 | 2016-12-08 | 富士フイルム株式会社 | Curable composition, production method of cured film, cured film, organic el display device, liquid crystal display device, touch panel and touch panel display device |
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JP5187492B2 (en) * | 2007-11-22 | 2013-04-24 | Jsr株式会社 | Curable resin composition, protective film and method for forming protective film |
JP6517077B2 (en) | 2015-04-28 | 2019-05-22 | 富士フイルム株式会社 | Curable composition, cured film, organic EL display device, liquid crystal display device, touch panel and touch panel display device |
KR20180031131A (en) * | 2016-09-19 | 2018-03-28 | 동우 화인켐 주식회사 | Photosensitive resin composition and photo-cured pattern prepared from the same |
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JP2008201910A (en) | 2007-02-20 | 2008-09-04 | Jsr Corp | Branched unsaturated polymer, radiosensitive resin composition and spacer for liquid crystal display element |
JP2016056369A (en) | 2014-09-11 | 2016-04-21 | 財團法人工業技術研究院Industrial Technology Research Institute | Hardcoat composition, polarizer, and display device using them |
JP2016204584A (en) | 2015-04-28 | 2016-12-08 | 富士フイルム株式会社 | Curable composition, production method of cured film, cured film, organic el display device, liquid crystal display device, touch panel and touch panel display device |
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