JPH0141649B2 - - Google Patents
Info
- Publication number
- JPH0141649B2 JPH0141649B2 JP11963380A JP11963380A JPH0141649B2 JP H0141649 B2 JPH0141649 B2 JP H0141649B2 JP 11963380 A JP11963380 A JP 11963380A JP 11963380 A JP11963380 A JP 11963380A JP H0141649 B2 JPH0141649 B2 JP H0141649B2
- Authority
- JP
- Japan
- Prior art keywords
- coating composition
- formula
- group
- weight
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000008199 coating composition Substances 0.000 claims description 52
- -1 cyano, acetyl Chemical group 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 238000012644 addition polymerization Methods 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 4
- 238000005299 abrasion Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- ZJQFXMRCCPCFEP-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCCOC(=O)C=C)C1=CC=CC=C1 ZJQFXMRCCPCFEP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000003678 scratch resistant effect Effects 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 239000002313 adhesive film Substances 0.000 claims 2
- PPZVFZKFTOQPMJ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(COC(=O)C=C)O)C1=CC=CC=C1 PPZVFZKFTOQPMJ-UHFFFAOYSA-N 0.000 claims 1
- RYKLYVSCHKVVCC-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCCOC(=O)C(=C)C)C1=CC=CC=C1 RYKLYVSCHKVVCC-UHFFFAOYSA-N 0.000 claims 1
- LTVGPGYKZWUOJS-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCCCOC(=O)C=C)C1=CC=CC=C1 LTVGPGYKZWUOJS-UHFFFAOYSA-N 0.000 claims 1
- OMJPVTWBJMWZGF-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCCCCOC(=O)C=C)C1=CC=CC=C1 OMJPVTWBJMWZGF-UHFFFAOYSA-N 0.000 claims 1
- XBCOQVFCVSGXPG-UHFFFAOYSA-N [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(O)COC(=O)C(=C)C)C1=CC=CC=C1 XBCOQVFCVSGXPG-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 description 14
- 238000000576 coating method Methods 0.000 description 13
- 238000001723 curing Methods 0.000 description 12
- 239000006096 absorbing agent Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 10
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 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
- 239000004305 biphenyl Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical class C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000003915 air pollution Methods 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- CFENKJQKDBNQRS-UHFFFAOYSA-N 1,18-diisocyanatooctadecane Chemical compound O=C=NCCCCCCCCCCCCCCCCCCN=C=O CFENKJQKDBNQRS-UHFFFAOYSA-N 0.000 description 1
- RXVBJUZEFSAYPW-UHFFFAOYSA-N 1,3-diphenylpropane-1,2,3-trione Chemical compound C=1C=CC=CC=1C(=O)C(=O)C(=O)C1=CC=CC=C1 RXVBJUZEFSAYPW-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- PIRWSGXNBGFLEA-UHFFFAOYSA-N 1-phenylbutane-1,2-dione Chemical compound CCC(=O)C(=O)C1=CC=CC=C1 PIRWSGXNBGFLEA-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- DIVXVZXROTWKIH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(O)(C)C(=O)C1=CC=CC=C1 DIVXVZXROTWKIH-UHFFFAOYSA-N 0.000 description 1
- OLVMPQNPFWQNTC-UHFFFAOYSA-N 2-hydroxy-2-phenyl-1-(2-phenylphenyl)ethanone Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1C1=CC=CC=C1 OLVMPQNPFWQNTC-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
- OSNJBWPTGQHCQC-UHFFFAOYSA-N 3,3-dimethyl-1-phenylbutane-1,2-dione Chemical compound CC(C)(C)C(=O)C(=O)C1=CC=CC=C1 OSNJBWPTGQHCQC-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- YGTVWCBFJAVSMS-UHFFFAOYSA-N 5-hydroxypentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCO YGTVWCBFJAVSMS-UHFFFAOYSA-N 0.000 description 1
- INRQKLGGIVSJRR-UHFFFAOYSA-N 5-hydroxypentyl prop-2-enoate Chemical compound OCCCCCOC(=O)C=C INRQKLGGIVSJRR-UHFFFAOYSA-N 0.000 description 1
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- WANLJGSQMHAZLK-UHFFFAOYSA-N cyano 3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=CC(OC#N)=O)C1=CC=CC=C1 WANLJGSQMHAZLK-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 description 1
- 150000008427 organic disulfides Chemical class 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
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The present invention relates to radiation-curable coating compositions containing copolymerizable ultraviolet absorber compounds capable of providing polymeric materials with improved photodegradability. Coating compositions which can be cured under the influence of radiation in general, particularly ultraviolet radiation as well as electron beams, are well known.
Typical examples of conventional paints include U.S. Patent No.
No. 3782961, No. 3829531, No. 3850770, No.
No. 3874906, No. 3864133, No. 3891523, No.
No. 3895171, No. 3899611, No. 3907574, No.
Includes paints disclosed in Nos. 3912516, 3932356 and 3989609. Unfortunately, these coating compositions have a number of drawbacks and do not include UV absorbers in the composition. Many of these coating compositions are not flexible enough to cause cracks in the coating when applied to flexible supports such as polyvinyl chloride. Other compositions have the undesirable result of not adhering well to the substrate and becoming susceptible to migration or delamination. Still other coating compositions require the use of solvents, which must be evaporated during the curing process. Evaporation of such solvents consumes energy and causes air pollution problems. Other compositions produce coatings that are yellow, have poor weather resistance, and have insufficient scratch, stain, abrasion, and/or solvent resistance. It is known to use UV absorbers in plastics or paints. The absorber absorbs the radiation and dissipates the energy, thus protecting the coating from structural deterioration. Significant economic savings are achieved by incorporating the UV absorber into the surface of the plastic article rather than incorporating it throughout, as is conventionally done. Additionally, conventional surface applications such as using solvents or paint vehicles are undesirable due to pollution risks and large volume processing requirements. Although radiation curing can produce paint films that are easier to handle, until now UV absorbers have consumed energy from the radiation source, resulting in either too high energy requirements for curing or a slow curing rate. It was too late. If a small amount of UV photoinitiator is used to facilitate curing, the addition of most UV stabilizers will interfere with curing. SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide a superior coating composition that is substantially free of one or more of the disadvantages of conventional radiation-curable coating compositions. Another object of the present invention is to provide a coating composition that produces a coating that is weather resistant, scratch resistant, stain resistant, abrasion resistant, solvent resistant and non-yellowing. Another object of the present invention is to obtain a coating composition that does not contain volatile solvents. Another object of the invention is to provide an improved method for coating substrates such as natural leather, synthetic leather, polyvinyl chloride, polyurethane and polycarbonate. Another object of the present invention is to obtain a coating composition containing a copolymerizable ultraviolet absorber that can be cured by radiation. The above and other objects are achieved in the present invention by the following formula: (In the formula, R 1 is a hydrogen atom or a methyl group, and Y is a divalent urethane residue); and B (where (Ar) 1 and (Ar) 2 are benzene-based and naphthalene-based aromatic carbocyclic nuclei, independently of the others, phenyl groups, or alkyl, halo,
alkoxy, carboxy, carbalkoxy,
selected from phenyl and naphthyl groups substituted with cyano, acetyl, benzoyl, phenyl, alkylphenyl, phenoxyphenyl, alkyl-substituted phenoxy or alkoxyphenyl-substituted phenyl groups, X is unsubstituted or halo, cyano, C1 ïœ C6
alkyl, C1 - C6 alkoxy, C2 - C17 alkylene group substituted with C1-C6 alkoxyalkyl or C1 - C6 alkoxyalkyleneoxy , Y is C3 - C12 selected from the group consisting of acryloyl, C3 - C12 alkyl acryloyl, C3 - C12 acryloxyalkyl, C3 - C12 acryloxyhydroxyalkyl, C3- C12 alkylacryloxyhydroxyalkyl A copolymerizable group or -RCR'-CHR'', where R is unsubstituted or substituted with a hydroxyl group
C1 - C10 phenylene, C1 - C10 alkylene,
C 1 -C 10 oxyalkylene or C 1 -C 10 alkyleneoxyalkylene group, Râ² and Râ³ are independently hydrogen atoms or
This is achieved by providing a coating composition containing a copolymerizable (2-cyano-3,3-diphenylacryloxy)alkylene acrylic ester ultraviolet absorber represented by (representing a C1 to C6 alkyl group) be done. In the most preferred compositions of the invention, (Ar) 1 and (Ar) 2 are phenyl groups, X is -C 2 H 4 ,
R is alkylene--CH 2 --, and R' and R'' both represent hydrogen atoms. The one or more vinyl monomers that can be copolymerized with the oligomer in the composition are N-vinyl-2-pyrrolidone and acrylic ester. Formula oligomers having acrylic or methacrylic components are well known in the industry. Oligomers of this type are described in U.S. Pat.
No. 3989609 and No. 3895171.
A preferred form of oligomer has both an acrylic component and a urethane moiety in the Y group. Examples of these compounds are U.S. Pat.
It is published in No. 3864133 and No. 3850770. A preferred new form of acrylic urethane is represented by the following formula and formula: However, in the above formula, R 1 is a hydrogen atom or a methyl group, R 2 is a lower alkylene group, R 3 is an aliphatic group or an alicyclic group, X is -O- or -NH-, and n is an integer from 2 to 50. show. These oligomers are made by reacting polytetrahydrofuran, polycaprolactone polyols, and other polyols with diisocyanates to form isocyanate-terminated prepolymers. The isocyanate-terminated prepolymer is then capped with a capping agent to produce oligomers of formula and formula. Preferred oligomers of the formula are of the formula; preferred oligomers of the formula are of the formula: However, in the above formula, n represents an integer of 5 to 20. Polytetrahydrofuran is available from DuPont under the trade names ``Telecor-650'', ``Telecor-1000'' and ``Telecor-2000'', and from Quaker Coats Company under the trade names ``Polymegu-650'' and ``Polymegu-650''.
It is available on the market under the trade names "Polymegu-1000" and "Polymegu-2000". The numerical value in the above trade name indicates the approximate molecular weight of polytetrafuran. The most preferred polytetrahydrofuran is
Consistent with the definition of "n" in the formula and formula
It has a molecular weight of 650. At higher molecular weights, where "n" exceeds about 50, the resulting oligomers are too viscous. Caprolactone polyol is "NIAX Caprolactone Polyols" from Union Carbide Corporation.
PCP-200, PCP-0210, PCP-0230, PCP-
0240, PCPâ0300, PCPâ0301 and PCPâ
It is available on the market under the trade name 0310. The 0200 series are diols with molecular weights of 530, 830, 1250 and 2000, respectively. The 0300 series are triols with molecular weights of 540, 300 and 900, respectively. , , and the oligomers of formula U.S. Patent No.
It can be manufactured according to No. 4129709. Capping agents useful in the present invention are those that react with the isocyanate-terminated prepolymer to form oligomers of the formula. Generally, any capping agent having a terminal amine or hydroxyl group and having an acrylic or methacrylic acid moiety is suitable. Suitable capping agents include, among others, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl, methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, hydroxypentyl acrylate, hydroxypentyl methacrylate, hydroxyhexyl acrylate, hydroxyhexyl methacrylate. , aminoethyl acrylate and aminoethyl methacrylate. Diisocyanates useful in preparing oligomers of formula are aliphatic and cycloaliphatic diisocyanates that react with the terminal hydroxyl groups present in polytetrahydrofuran. Aromatic diisocyanates, of course, perform the same reaction, but do not produce products as satisfactory as those obtained by the use of aliphatic diisocyanates. Examples of suitable diisocyanates include, among others, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, sold under the trade name "Hexylene W" by Dubon, and trimethyl-hexamethylene diisocyanate, 1,6-hexamethylene diisocyanate. ,2,4,4-triethyl-
These include 1,6-hexylene diisocyanate, octadecylene diisocyanate and 1,4-cyclohexylene diisocyanate. A preferred diisocyanate is isophorone diisocyanate (3-
isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate) and 4,4'-dicyclohexylmethane-diisocyanate. The vinyl monomer copolymerizable with the oligomer can be one or more monomers that are compatible with the selected oligomer. Acrylic acid esters and N-vinyl-2-pyrrolidone having a boiling point of at least 200° C. at 760 mm Hg are preferred. These monomers make it possible to adjust the viscosity and facilitate the coating operation, and N-vinyl-2-pyrrolidone increases the curing rate. The weight ratio of oligomer to N-vinyl-2-pyrrolidone can vary within a range without adversely affecting the properties of the resulting cured coating composition, but generally the oligomer and N-vinyl-2-pyrrolidone are 1:9. Weight ratio of ~9:1, preferably ~1:3
Present in a weight ratio of 3:1. The ratio is even greater.
For example, when enriched in oligomers, uncured coating compositions tend to become too viscous. Such high viscosity makes it difficult to apply the uncured coating composition to a support. As the ratio becomes smaller, the resulting uncured coating composition tends to become too hard and undeformable. Acrylic ester is 760mmHg and at least 200
It should have a boiling point of °C. Low boiling acrylic esters tend to evaporate during curing. When such evaporation occurs, undesirable changes occur in the coating composition. Furthermore, vaporized acrylic esters tend to polymerize at radiation sources, such as ultraviolet lamps or electron beam windows. This evaporation also causes unwanted air pollution. Acrylic esters useful in this invention include monoesters, diesters, and higher esters of both acrylic and methacrylic acids, among others. Examples of suitable acrylic acids include, among others, 1,4-butanediol diacrylate;
These include 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, pentaerythritol-tetramethacrylate, trimethylolpropane triacrylate, ethylhexyl-acrylate, ethylhexyl-methacrylate, pentyl-acrylate, hexyl-acrylate and cyclohexyl-methacrylate. 1,4-butanediol diacrylate and 1,6-hexanediol diacrylate are the preferred acrylic esters. The acrylic ester can be present in the coating composition in a wide range of amounts, but in a weight ratio of 1:9 to 9:1, preferably 1:3 to 3:1, compared to the formula or oligomer of the formula. Make it exist. The copolymerizable (2-cyano-3,3-diphenylacryloxy) alkylene acrylate ultraviolet absorber has the following formula. In the above formula, (Ar) 1 and (Ar) 2 are benzene-based and naphthalene-based aromatic carbocyclic nuclei, and are phenyl groups or alkyl, halo, alkoxy, carboxy, carboalkoxy, cyano, acetyl, selected from phenyl and naphthyl groups substituted with benzoyl, phenyl, alkylphenyl, phenoxyphenyl, alkyl-substituted phenoxy, or alkoxyphenoxy-substituted phenyl, and X is unsubstituted or halo, cyano, C 1 - C6 alkyl, C1 -C6 alkoxy, C1 - C6 alkoxyalkyl or C1 - C6 alkoxyalkyleneoxy -substituted alkylene group, Y is C3 - C12 acryloyl, C3 -C6 a copolymerizable group selected from the group consisting of C12 alkyl acryloyl, C3 to C12 alkyloxyalkyl, C3 to C12 acryloxyhydroxyalkyl, C3 to C12 alkylacryloxyhydroxyalkyl; or -RCRâ²=CHRâ³, where R is unsubstituted or hydroxyl-substituted C 1 to C 10 phenylene;
C1 - C10 alkylene, C1 - C10 oxyalkylene or C1 - C10 alkyleneoxyalkylene, Râ² and Râ³ are independently hydrogen atoms or C1
~ C6 alkyl group. Suitable (Ar) 1 and (Ar) 2 groups are described in U.S. Pat.
No. 3,644,466, which includes representative starting benzophenone compounds. In the most preferred embodiment of the invention, (Ar) 1 and (Ar) 2 are both phenyl groups. The X group is a C2 - C17 unsubstituted or substituted alkylene group. Preferred groups are C2 - C6 unsubstituted lower alkylene groups synthetically derived from ethylene glycol, propylene glycol, butanediol, and the like. Representative X groups are -CH 2 CH 2 -,, -
CH 2 CH 2 CH 2 â, âCH 2 CH 2 CH 2 CH 2 â, etc. Most preferred is --CH 2 CH 2 --. The Y group can be copolymerized with the vinyl monomer so that the UV absorber becomes an essential part of the polymer.
Suitable Y groups are derived from acryloyl, alkylacryloyl, acryloxyalkyl, acryloxyhydroxyalkyl and alkylacryloxyhydroxyalkyl having from C3 to C12 carbon atoms. Preferred groups are acryloyl, methacryloyl, glycidyl acryloyl and glycidyl methacryloyl. A typical Y group is
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å°ãªãã€ãã[Formula] CH 2 (3-methacryloxy-2-hydroxypropyl). The most preferred group is acryloyl or methacryloyl. The compounds of the formula contain a group copolymerizable with a UV absorber moiety in the same molecule. These groups are effectively separated by the X group so that each can perform its own function without interference from the others. Therefore, the absorbent part does not interfere with the copolymerization and Y
The groups do not affect the light absorption properties of the molecule. -RCR'=CHR'' groups can be copolymerized with vinyl monomers and the UV absorber becomes an essential part of the polymer.Suitable groups are allyl, crotyl, methylpropenyl, vinylbenzyl, vinyloxyether, allyloxy-2- Hydroxypropyl and 2-hydroxy-3-butenyl. Most preferred is allyl. The absorbent compound is 2-hydroxyalkyl (2
It can be produced by esterifying -cyano-3,3-diphenyl)acrylate with acryloyl halide or acrylic acid. In this synthesis, it is preferable to first protect the hydroxyl group of the hydroxyalkylcyanoacetate by acylation with a group convertible to a hydroxyl group by hydrolysis, for example, by acylation using acetyl chloride to obtain the corresponding acetoxyalkylcyanoacetate. The protected compound is then condensed with benzophenone by Knoeffenagel reaction to obtain acetoxyalkyl (2-cyano-3,3-diphenyl) acrylate in high yield. Acid hydrolysis of the protected acetyl group then yields the corresponding hydroxy intermediate, which is then directly esterified with the appropriate acryloyl halide or acrylic acid to yield the desired compound. The absorbent compound is 2-hydroxyalkyl-2-
It can be produced by alkylating cyano-3,3-diphenyl acrylate with an ethylene halide. In this synthesis, it is preferred to first protect the hydroxyl group of the hydroxyalkylcyanoacetate by acylation with a group convertible to a hydroxyl group by hydrolysis, for example, by acylation using acetyl chloride to obtain the corresponding acetoxyalkylcyanoacetate. The protected compound is then condensed with benzophenone by Knoeffenagel reaction to obtain acetoxyalkyl (2-cyano-3,3-diphenyl) acrylate in high yield. Acid hydrolysis of the protected acetyl group then yields the corresponding hydroquine intermediate, which is then directly alkylated with a suitable ethylene halide to yield the desired compound. The amount of UV absorber of the above formula in the coating composition for radiation curing is 0.5% to 5%, preferably 0.75% to 2%, most preferably about 1.5% by weight of the composition.
It is. If the amount is less than this, a coating that maintains light transmission or low yellowing cannot be obtained. Above the above amounts, curing will be unacceptably slow. If curing is carried out with ultraviolet light, a photoinitiator is used. Suitable photoinitiators include vicinal keto aldonyl compounds (i.e. compounds having ketone and aldehyde groups) such as diacetyl, benzyl;
3-pentanedione, 2,3-octanedione,
1-phenyl-1,2-butanedione, 2,2-
Dimethyl-4-phenyl-3,4-butanedione, phenyl-glyoxal, diphenyl-triketone; aromatic diketones, such as anthraquinone; acryloin, such as benzoin; pivaloin-acryloin ether, such as benzoin-methyl-ether, benzoin-ethyl- Ethers, benzoin-butyl-ether, benzoin-isobutyl-ether, benzoin-phenyl-ether; including alpha-methyl-benzoin, alpha-alkylbenzoin, and even phenylbenzoin as described in U.S. Pat. No. 2,722,512. Included are alpha hydrocarbon substituted aromatic acryloins; diaryl ketones such as benzophenone and dinaphthyl ketone; and organic disulfides such as diphenyl disulfide. The photoinitiator may also contain a synergist, such as a tertiary amine, to facilitate the conversion of light absorption energy to polymerization initiating free radicals. Dimethoxyphenylacetophenones such as diethoxyacetophenone available from Union Carbide Corporation, IRGACURE 651 available from Ciba Geigy or Vicure available from Stauffer Chemical Company. Benzoin ethers such as No. 10 are preferred. The photoinitiator is present in the coating composition in an amount sufficient to initiate the desired polymerization under the influence of the amount of actinic energy absorbed. Generally, the coating composition contains from 0.01 to 5% by weight of photoinitiator, based on the weight of the coating composition. Additionally, addition polymerization initiators can be included in the coating composition to prevent undesirable autopolymerization of the coating composition during storage prior to use. Examples of suitable addition polymerization initiators include, among others, di(1,4-sec butylamino)benzene, available from DuPont under the tradename "Anti-Oxidant 22" and phenothiazine, available from Tefuenco Chemical Company. . The addition polymerization initiator is present in an amount sufficient to avoid autopolymerization and is generally present in an amount of 100 to 300 ppm based on the weight of the coating composition. The coating composition can also contain surfactants. Preferred surfactants are silicone surfactants such as those available from Dow Corning Corporation under the trade name "DC-193." The surfactant is present in an amount necessary to reduce the surface tension of the coating composition. Generally, the surfactant is present in an amount of 0.1 to 5% by weight based on the weight of the coating composition. The coating compositions of the present invention may contain, for example, flow control agents, leveling agents, organic and inorganic dyes and pigments, fillers, plasticizers, lubricants and reinforcing agents, such as alumina, silica, clay, talc, glass powder, carbon. May contain black and glass fibers. The coating compositions of this invention can be applied and cured as a 0.5 mil thick film onto a substrate. Curing is preferably carried out under an inert atmosphere of nitrogen. The coating composition can be applied as a thin film by any conventional method, such as by brush spraying, brushing, dipping, roll coating, and the like. Typically, the film on the support is conveyed on a conveyor and passed under a source of free radical generators in a radial manner. The coated side of the support is exposed to radiation for a sufficient time to polymerize, converting the film into a tough, flexible adhesive coating. Reference herein to radiation shall mean a radiation source that generates free radicals and induces addition polymerization of vinyl bonds. Actinic radiation is 2000-7500A, preferably
A wavelength of 2000-4000A is suitable. One of the actinic radiations useful in the present invention is ultraviolet radiation; other forms of actinic radiation include solar and artificial sources such as RS solar lamps, carbon arc lamps, xenon arc lamps, mercury vapor lamps, tungsten halide lamps, lasers, and ultraviolet radiation. It comes from a fluorescent lamp that uses phosphorescent substances. For commercial acceptance it is necessary to obtain UV curing rates of 6 m (20 ft)/min/lamp or higher. Coating compositions employing UV absorbers of the formula present in amounts of 0.5 to 3% by weight of the composition, if fairly thick (10 mils or less),
Can be cured at 25-50 ft/min/ramp speed. A preferred electron beam system produces a wide beam of electrons (electron curtain) directly from a linear cathode. Broad electrons accelerated to high speed by a 200 KV potential from the cathode of the electron gun are emitted from the chamber through a foil window onto the coated support (Electron Curtain TM, by Energy Sciences, Inc.). As mentioned above, electron beam curing of the coating composition is less than 5 megarads, and curing is usually carried out at 2 megarads. Curing above 8 megarads is expensive and appears to be unacceptable. A laminate consisting of a thin film of a coating based on acrylic urethane with the UV absorber (2-cyano-3,3-diphenyl acryloyloxy)alkylene ethylene ether on transparent polyvinyl chloride has shown surprising results. In particular, it is not leached and does not yellow. The invention will be illustrated with reference to the following examples. Unless otherwise specified, "parts" and "%" mean "parts by weight" and "% by weight." Example 1 Production of radiation-cured coatings 1 dry resin kettle 300.8 with air inlet tube, stirrer, thermometer and dropping funnel.
g (1.3 mol) of isophorone diisocyanate and 10% (W/
V) 4.8 ml of ethylhexyl acrylate solution was fed. Dry air was bubbled through the solution while stirring, and 322.1 g (0.61 mol) of polyol caprolactone (PCP-200) was added dropwise over 45 minutes. The solution was then heated to 80°C and the reactants were maintained at this temperature for 30 minutes. After cooling to 55â,
160ml of phenothiazine was mixed. 151.9 g (1.3 moles) of hydroxyethyl acrylate were then rapidly added. The temperature was raised to 80°C and maintained for 2 hours. The resulting oligomer (58.1 g) was mixed with 25.4 g ethylhexyl acrylate, 16.8 g vinylpyrrolidone, 14.2 g hexanediol diacrylate, 1.8 g DC-193 silicone surfactant, 2.4 g
g of Bikiure 10 photoinitiator and 2.5 g of 2-
A paint was made by mixing with (2-cyano-3,3-diphenylacryloxy)ethyl acrylate. The resulting syrup was coated onto polyvinyl chloride to form a film having a thickness of 1.5 mils. This film was then cured with ultraviolet light in an inert atmosphere to obtain a tough transparent coating containing a copolymerized ultraviolet absorber compound. The polyvinyl chloride plate thus protected showed only a slight tendency to yellowing even after being tested in a weatherometer for 734 hours. Example 2 The produced oligomer (58.1 g) was mixed with 25.4 g ethylhexyl acrylate, 16.8 g vinylpyrrolidone, 14.2 g hexanediol diacrylate, 1.8 g DC-193 silicone surfactant, 2.4 g
g of Bikiure 10 photoinitiator and 2.5 g of 2-
(2-cyano-3,3-diphenylacryloxy)ethyl was mixed with allyl ether to make a paint. The resulting syrup was coated onto a polyvinyl chloride plate to form a film having a thickness of 1.5 mils. The film was then cured with ultraviolet light under an inert atmosphere to yield a tough transparent coating containing the copolymerized ultraviolet absorber compound of the present invention. The protected polyvinyl chloride film had less tendency to yellow than the unprotected film in the Weatherometer test.
Claims (1)
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ç©ã[Claims] 1 A The following formula (In the formula, R 1 is a hydrogen atom or a methyl group, and Y is a divalent urethane residue); and B (where (Ar) 1 and (Ar) 2 are benzene-based and naphthalene-based aromatic carbocyclic nuclei, independently of the others, phenyl groups, or alkyl, halo,
alkoxy, carboxy, carbalkoxy,
selected from phenyl and naphthyl groups substituted with cyano, acetyl, benzoyl, phenyl, alkylphenyl, phenoxyphenyl, alkyl-substituted phenoxy, or alkoxyphenyl-substituted phenyl, and X is unsubstituted or halo, cyano, C1 ïœ C6
a C2- C17 alkylene group substituted with C1 - C6 alkyl, C1 - C6 alkoxy, C1 - C6 alkoxyalkyl, or C1 - C6 alkoxyalkyleneoxy, Y is C3 - C12 acryloyl, C3 to C12 alkyl acryloyl, C3 to C12 acryloxyalkyl, C3 to C12 acryloxyhydroxyalkyl , and C3 to C12 alkylacryloxyhydroxyalkyl. a copolymerizable group or -RCRâ²=CHRâ³,
However, R is unsubstituted or substituted with a hydroxyl group
C1 - C10 phenylene group, C1 - C10 alkylene group, C1 - C10 oxyalkylene group or C1- C10 oxyalkylene group
C 10 alkyleneoxyalkylene group, Râ² and Râ³ are hydrogen atoms or
1. A radiation-curable coating composition comprising a copolymerizable ultraviolet absorber compound represented by (representing a C1 to C6 alkyl group). 2. The coating composition according to claim 1, which contains a vinyl monomer copolymerizable with the oligomer. 3. The coating composition of claim 1, comprising an addition polymerization initiator present in an amount sufficient to prevent autopolymerization of the composition during storage. 4 Addition polymerization initiator is 100 to 100% by weight of the composition
A coating composition according to claim 3, present in an amount of 300 ppm. 5 The weight ratio of oligomer to vinyl monomer is 1:9 ~
The coating composition according to claim 3, wherein the ratio is 9:1. 6. The coating composition of claim 1 further comprising a photoinitiator present in an amount sufficient to initiate the desired polymerization under the influence of the amount of actinic energy absorbed. 7 Ultraviolet absorber is 0.5 to 0.5 to the weight of the composition
Coating composition according to claim 1, present in an amount of 5% by weight. 8. The coating composition according to claim 1, wherein (Ar) 1 and (Ar) 2 in the formula are phenyl groups. 9. The coating composition according to claim 1, wherein in the formula, X is a C2 to C6 alkylene group. 10 In the formula, Y is C 3 to C 12 acryloyl,
C3 to C12 methacryloyl, C3 to C12 3-acryloxy-2-hydroxypropyl, or C3
The coating composition according to claim 1, which is a 3-methacryloxy-2-hydroxypropyl group of ~ C12 . In formula 11, (Ar) 1 and (Ar) 2 are phenyl groups, X is a C 2 to C 6 alkylene group, and Y is a C 3 to C 6 alkylene group.
C12 acryloyl, C3 ~ C12 methacryloyl,
The coating composition according to claim 1, which is a C3 to C12 3-acryloxy-2-hydroxypropyl group or a C3 to C12 3-methacryloxy-2 - hydroxypropyl group. 12. The coating composition according to claim 1, wherein the formula is 2-(2-cyano-3,3-diphenylacryloxy)ethyl acrylate. 13. The coating composition according to claim 1, wherein the formula is 2-(2-cyano-3,3-diphenylacryloxy)ethyl methacrylate. 14. The coating composition according to claim 1, wherein the formula is 3-(2-cyano-3,3-diphenylacryloxy)propyl acrylate. 15. The coating composition according to claim 1, wherein the formula is 4-(2-cyano-3,3-diphenylacryloxy)butyl acrylate. 16. The coating composition according to claim 1, wherein the formula is 3-(2-cyano-3,3-diphenylacryloxy)-2-hydroxypropyl acrylate. 17. The coating composition according to claim 1, wherein the formula is 3-(2-cyano-3,3-diphenylacryloxy)-2-hydroxypropyl methacrylate. 18 A The following formula (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is a lower alkylene group, R 3 is an aliphatic or alicyclic group, X is -O- or -NH-, and n is an integer from 2 to 50. ), B N-vinyl-2-pyrrolidone, C hexanediol diacrylate, D 2-(2-cyano-3,3) present in an amount of 0.5 to 5 weight percent relative to the weight of the composition.
- diphenyl acryloxyethyl acrylate, E a photoinitiator present in an amount of 0.01 to 5 percent by weight relative to the weight of the composition, F an addition polymerization initiator present in an amount of 100 to 300 ppm relative to the weight of the composition , G based on a silicone surfactant present in an amount of 0.1 to 5 percent by weight relative to the weight of the composition, with the proviso that A:B is 1:3 to 3:1;
A:C is 1:3 to 3:1, photopolymerized in the presence of ultraviolet light to produce weather-resistant, scratch-resistant, stain-resistant, abrasion-resistant, solvent-resistant, flexible A paint coating composition according to claim 1, which is capable of producing an adhesive film. 19 A The following formula (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is a lower alkyl group, R 3 is an aliphatic or alicyclic group,
X is -O- or -NH-, n is an integer of 2 to 50), B N-vinyl-2-pyrrolidone, C hexanediol diacrylate D 0.5 to 3 based on the weight of the composition 2-(2-cyano-3,3
-diphenylacryloxy)ethyl acrylate, E. a photoinitiator present in an amount of 0.01 to 5 percent by weight relative to the weight of the composition, F. an addition polymerization initiator present in an amount of 100 to 300 ppm relative to the weight of the composition. G is based on a silicone surfactant present in an amount of 0.1 to 5 percent by weight relative to the weight of the composition, with the proviso that A:B is 1:3 to 3:1;
A:C is 1:3 to 3:1, photopolymerized in the presence of ultraviolet light to produce weather-resistant, scratch-resistant, stain-resistant, abrasion-resistant, solvent-resistant, flexible A coating composition according to claim 1, which is capable of producing an adhesive film. 20. The coating composition according to claim 1, wherein RCR'=CHR'' in the formula is allyl, crotyl, methylpropenyl, vinylbenzyl, vinyloxyether, allyloxy-2-hydroxypropyl or 2-hydroxy-3-butenyl. thing.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/071,356 US4276136A (en) | 1979-01-26 | 1979-08-30 | Radiation curable coating composition comprising an ethylenically unsaturated oligomer and an ethylenically unsaturated copolymerizable ultra-violet absorber |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5634769A JPS5634769A (en) | 1981-04-07 |
JPH0141649B2 true JPH0141649B2 (en) | 1989-09-06 |
Family
ID=22100797
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11963380A Granted JPS5634769A (en) | 1979-08-30 | 1980-08-29 | Irradiation curable paint composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5634769A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5776063A (en) * | 1980-10-29 | 1982-05-12 | Toyobo Co Ltd | Curable coating composition |
JPS59103793A (en) * | 1982-08-18 | 1984-06-15 | Toa Paint Kk | Ultraviolet-curing undercoating composition and production of multilayer coated film by utilizing the same |
JPH04328273A (en) * | 1991-04-25 | 1992-11-17 | Japan Storage Battery Co Ltd | Sealed type lead-acid battery |
JP5610200B2 (en) * | 2010-06-10 | 2014-10-22 | äžè±ã¬ã€ãšã³æ ªåŒäŒç€Ÿ | Active energy ray-curable resin composition for casting and optical component |
-
1980
- 1980-08-29 JP JP11963380A patent/JPS5634769A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5634769A (en) | 1981-04-07 |
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