KR19990072925A - Pigmented photocurable composition - Google Patents
Pigmented photocurable composition Download PDFInfo
- Publication number
- KR19990072925A KR19990072925A KR1019990006255A KR19990006255A KR19990072925A KR 19990072925 A KR19990072925 A KR 19990072925A KR 1019990006255 A KR1019990006255 A KR 1019990006255A KR 19990006255 A KR19990006255 A KR 19990006255A KR 19990072925 A KR19990072925 A KR 19990072925A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- phenyl
- formula
- alkoxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 126
- -1 benzoin derivative compounds Chemical class 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000000049 pigment Substances 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 28
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
- 238000007650 screen-printing Methods 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 8
- 239000004408 titanium dioxide Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
- 235000021286 stilbenes Nutrition 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000012463 white pigment Substances 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 229960000956 coumarin Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000008199 coating composition Substances 0.000 abstract description 21
- 238000001723 curing Methods 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- 229920005862 polyol Polymers 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 230000005855 radiation Effects 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000000976 ink Substances 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000000600 sorbitol Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 6
- 239000006081 fluorescent whitening agent Substances 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012778 molding material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
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- 229920006337 unsaturated polyester resin Polymers 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 125000003277 amino group Chemical group 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
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- 229910001507 metal halide Inorganic materials 0.000 description 3
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- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- 230000003678 scratch resistant effect Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 150000003577 thiophenes Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 238000005809 transesterification reaction Methods 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Architecture (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
하나 이상의 에틸렌성 불포화 광 중합 가능한 화합물(a),At least one ethylenically unsaturated photopolymerizable compound (a),
광 개시제로서의 하나 이상의 모노아실포스핀 옥사이드 화합물, 비스아실포스핀 옥사이드 화합물 또는 트리스아실포스핀 옥사이드 화합물, 또는 이러한 화합물(들)과 α-하이드록시케톤, α-아미노케톤 및/또는 벤조인 유도체 화합물과의 혼합물(b),One or more monoacylphosphine oxide compounds, bisacylphosphine oxide compounds or trisacylphosphine oxide compounds as photoinitiators, or such compound (s) with α-hydroxyketones, α-aminoketones and / or benzoin derivative compounds Mixture with (b),
하나 이상의 형광증백제(c) 및One or more fluorescent brighteners (c) and
하나 이상의 안료(d)를 포함하는 광 중합 가능한 조성물은 놀랍게도 완전 경화 특성이 우수하므로, 피복 조성물, 예를 들면, 백색 표면 피복 조성물로서 특히 적합하다.Photopolymerizable compositions comprising at least one pigment (d) are particularly suitable as coating compositions, for example white surface coating compositions, because they are surprisingly good in full cure properties.
Description
본 발명은 아실포스핀 옥사이드 광 개시제와 형광증백제를 포함하며, 특히 백색 표면 피복 조성물로서 사용되는 착색된 광 경화성 조성물에 관한 것이다.The present invention relates to colored photocurable compositions comprising acylphosphine oxide photoinitiators and fluorescent brighteners, in particular used as white surface coating compositions.
모노아실포스핀 옥사이드, 비스아실포스핀 옥사이드 및 트리스아실포스핀 옥사이드는, 특히 짙게 착색된 피복물을 경화시키기 위한 광 개시제로서 문헌에 공지되어 있다. 예를 들면, 미국 특허 제4,298,738호에는, 모노아실포스핀 옥사이드가 기재되어 있으며, 미국 특허 제4,737,593호, 미국 특허 제4,792,632호 및 미국 특허 제5,399,770호에는, 비스아실포스핀 옥사이드가 기재되어 있다. 또한, 후자의 공보에는, 모노아실포스핀 옥사이드 및 비스아실포스핀 옥사이드와 α-하이드록시케톤 및 벤조페논과의 광 개시제 혼합물이 기재되어 있다. 트리스아실포스핀 옥사이드 화합물에 대한 설명은 WO 제96/07662호에서 찾아볼 수 있다. 유럽 특허 제741 333호에는, 특히 영상 시스템에서 사용되는 조성물의 반응성이 증가된 착색되지 않은 광 중합 가능한 조성물에 있어서의 아실포스핀 옥사이드 화합물과 형광증백제 화합물과의 배합물이 기재되어 있다.Monoacylphosphine oxides, bisacylphosphine oxides and trisacylphosphine oxides are known in the literature as photoinitiators, particularly for curing darkly colored coatings. For example, US Pat. No. 4,298,738 describes monoacylphosphine oxide and US Pat. No. 4,737,593, US Pat. No. 4,792,632 and US Pat. No. 5,399,770 describe bisacylphosphine oxide. The latter publication also describes photoinitiator mixtures of monoacylphosphine oxides and bisacylphosphine oxides with α-hydroxyketones and benzophenones. A description of the trisacylphosphine oxide compounds can be found in WO 96/07662. EP 741 333 describes combinations of acylphosphine oxide compounds with fluorescent brightener compounds, especially in uncolored photopolymerizable compositions with increased reactivity of the compositions used in imaging systems.
당해 분야에서는, 특히 착색된 표면 피복물의 제조에 있어서, 안료 함량이 높음에도 불구하고, 신속하고 완전 경화를 나타내는 광 경화성 조성물이 요구되어 왔다.In the art, in particular in the production of colored surface coatings, despite the high pigment content, there has been a demand for photocurable compositions which exhibit rapid and complete curing.
본 발명자들은, 아실포스핀 옥사이드 광 개시제를 포함하는 착색된 광 경화성 조성물에 형광증백제 화합물을 첨가하는 경우, 형광증백제 화합물이 일종의 증감제로서 작용하며, 뜻밖에도 이러한 조성물의 완전 경화가 개선된다는 사실을 밝혀내었다.The inventors have found that when adding a fluorescent brightener compound to a colored photocurable composition comprising an acylphosphine oxide photoinitiator, the fluorescent brightener compound acts as a kind of sensitizer, and unexpectedly the complete cure of such a composition is improved. Revealed.
따라서, 본 발명은Therefore, the present invention
하나 이상의 에틸렌성 불포화 광 중합 가능한 화합물(a),At least one ethylenically unsaturated photopolymerizable compound (a),
광 개시제로서의 하나 이상의 모노아실포스핀 옥사이드 화합물, 비스아실포스핀 옥사이드 화합물 또는 트리스아실포스핀 옥사이드 화합물, 또는 이들 화합물(들)과 α-하이드록시케톤, α-아미노케톤 및/또는 벤조인 유도체 화합물과의 혼합물(b),One or more monoacylphosphine oxide compounds, bisacylphosphine oxide compounds or trisacylphosphine oxide compounds as photoinitiators, or these compound (s) with α-hydroxyketones, α-aminoketones and / or benzoin derivative compounds Mixture with (b),
하나 이상의 형광증백제(c) 및One or more fluorescent brighteners (c) and
하나 이상의 안료(d)를 포함하는 광 중합 가능한 조성물에 관한 것이다.A photopolymerizable composition comprising at least one pigment (d).
모노아실포스핀 옥사이드 화합물, 비스아실포스핀 옥사이드 화합물 또는 트리스아실포스핀 옥사이드 화합물은, 예를 들면, 화학식 1의 화합물이다.The monoacylphosphine oxide compound, the bisacylphosphine oxide compound or the trisacylphosphine oxide compound is, for example, a compound of formula (1).
위의 화학식 1에서,In Formula 1 above,
R1및 R2는 각각 독립적으로 C1-C18알킬, 하나 이상의 연속하지 않은 산소원자에 의해 차단된 C2-C18알킬, 페닐 치환된 C1-C4알킬, C2-C8알케닐, 페닐, 나프틸, 비페닐 또는 C5-C12사이클로알킬, 치환되지 않거나 할로겐, C1-C8알킬, C1-C8알킬티오 및/또는 C1-C8알콕시에 의해 일치환 내지 오치환된 라디칼 페닐, 나프틸, 비페닐 및 C5-C12사이클로알킬이거나,R 1 and R 2 are each independently C 1 -C 18 alkyl, C 2 -C 18 alkyl interrupted by one or more non-contiguous oxygen atoms, phenyl substituted C 1 -C 4 alkyl, C 2 -C 8 eggs Mono-substituted by kenyl, phenyl, naphthyl, biphenyl or C 5 -C 12 cycloalkyl, unsubstituted or halogen, C 1 -C 8 alkyl, C 1 -C 8 alkylthio and / or C 1 -C 8 alkoxy To missubstituted radicals phenyl, naphthyl, biphenyl and C 5 -C 12 cycloalkyl, or
R1및 R2는 -COR3이고,R 1 and R 2 are -COR 3 ,
R3은 치환되지 않거나 C1-C12알킬, C1-C12알콕시, C1-C12알킬티오 및/또는 할로겐에 의해 일치환 내지 오치환된 페닐이다.R 3 is an unsubstituted or substituted C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio and / or monosubstituted to ohchihwan phenyl by halogen.
α-하이드록시케톤, α-아미노케톤 및 벤조인 유도체 화합물은 화학식 2의 화합물이다.α-hydroxyketone, α-aminoketone and benzoin derivative compounds are compounds of formula (2).
위의 화학식 2에서,In Formula 2 above,
R4는 수소, C1-C18알킬, C1-C18알콕시, -OCH2CH2-OR8, 모르폴리노, SCH3,그룹 또는그룹이고,R 4 is hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, —OCH 2 CH 2 —OR 8 , morpholino, SCH 3 , Group or Group,
n은 2 내지 10의 값을 가지며,n has a value from 2 to 10,
G는 라디칼이고,G is a radical ego,
R5는 하이드록시, C1-C16알콕시, 모르폴리노, 디메틸아미노 또는 -O(CH2CH2O)m-C1-C16알킬이며,R 5 is hydroxy, C 1 -C 16 alkoxy, morpholino, dimethylamino or —O (CH 2 CH 2 O) m- C 1 -C 16 alkyl,
R6및 R7은 각각 독립적으로 수소, C1-C6알킬, 페닐, 벤질, C1-C6알콕시 또는 -O(CH2CH2O)m-C1-C16알킬이거나,R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl, phenyl, benzyl, C 1 -C 6 alkoxy or —O (CH 2 CH 2 O) m —C 1 -C 16 alkyl, or
R6및 R7은 이들이 결합되어 있는 탄소원자와 함께 사이클로헥실 환을 형성하고,R 6 and R 7 together with the carbon atoms to which they are attached form a cyclohexyl ring,
m은 1 내지 20의 수이며,m is a number from 1 to 20,
단 R5, R6및 R7은 모두 동시에 C1-C16알콕시 또는 -O(CH2CH2O)m-C1-C16알킬은 아니고,Provided that R 5 , R 6 and R 7 are not all C 1 -C 16 alkoxy or —O (CH 2 CH 2 O) m- C 1 -C 16 alkyl at the same time,
R8은 수소,또는이다.R 8 is hydrogen, or to be.
C1-C18알킬은 직쇄 또는 측쇄이며, 예를 들면, C1-C12-알킬, C1-C8-알킬, C1-C6-알킬 또는 C1-C4-알킬이다. 예는 메틸, 에틸, 프로필, 이소프로필, n-부틸, 2급 부틸, 이소부틸, 3급 부틸, 펜틸, 헥실, 헵틸, 2,4,4-트리메틸펜틸, 2-에틸헥실, 옥틸, 노닐, 데실, 운데실, 도데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실 및 옥타데실이다.C 1 -C 18 alkyl is straight or branched, for example C 1 -C 12 -alkyl, C 1 -C 8 -alkyl, C 1 -C 6 -alkyl or C 1 -C 4 -alkyl. Examples are methyl, ethyl, propyl, isopropyl, n-butyl, secondary butyl, isobutyl, tertiary butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl, octyl, nonyl, Decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.
마찬가지로, C1-C12알킬, C1-C8알킬 및 C1-C6알킬은 직쇄 또는 측쇄이며, 예를 들면, 위에서 언급한 바와 같은 것으로서, 상응하는 탄소수를 갖는 것이다.Likewise, C 1 -C 12 alkyl, C 1 -C 8 alkyl and C 1 -C 6 alkyl are straight or branched chains, for example as mentioned above, having the corresponding carbon number.
연속하지 않은 산소원자에 의해 1회 이상 차단된 C2-C18알킬은, 예를 들면, -O-에 의해 1회 내지 7회 차단되거나 1회 또는 2회 차단된다. 산소원자들은 각각 하나 이상의 메틸렌 그룹에 의해 서로로부터 분리되어, 예를 들면, 다음과 같은 구조 단위를 생성한다: -CH2-O-CH3, -CH2CH2-O-CH2CH3, -[CH2CH2O]y-CH3(여기서, y는 1 내지 8이다), -(CH2CH2O)7CH2CH3, -CH2-CH(CH3)-O-CH2-CH2CH3또는 -CH2-CH(CH3)-O-CH2-CH3.C 2 -C 18 alkyl blocked one or more times by non-contiguous oxygen atoms is blocked once or seven times or once or twice by, for example, -O-. The oxygen atoms are each separated from each other by one or more methylene groups, resulting in the following structural units: -CH 2 -O-CH 3 , -CH 2 CH 2 -O-CH 2 CH 3 , -[CH 2 CH 2 O] y -CH 3 , where y is 1 to 8,-(CH 2 CH 2 O) 7 CH 2 CH 3 , -CH 2 -CH (CH 3 ) -O-CH 2 -CH 2 CH 3 or -CH 2 -CH (CH 3 ) -O-CH 2 -CH 3 .
C1-C18알콕시는 직쇄 라디칼 또는 측쇄 라디칼이며, 예를 들면, C1-C12-알콕시, C1-C8-알콕시, C1-C6-알콕시 또는 C1-C4-알콕시이다. 예는 메톡시, 에톡시, 프로폭시, 이소프로폭시, n-부틸옥시, 2급 부틸옥시, 이소부틸옥시, 3급 부틸옥시, 펜틸옥시, 헥실옥시, 헵틸옥시, 2,4,4-트리메틸펜틸옥시, 2-에틸-헥실옥시, 옥틸옥시, 노닐옥시, 데실옥시, 도데실옥시, 헥사데실옥시 및 옥타데실옥시, 특히 메톡시, 에톡시, 프로폭시, 이소프로폭시, n-부틸옥시, 2급 부틸옥시, 이소부틸옥시 및 3급 부틸옥시, 바람직하게는 메톡시이다.C 1 -C 18 alkoxy is a straight or branched radical, for example C 1 -C 12 -alkoxy, C 1 -C 8 -alkoxy, C 1 -C 6 -alkoxy or C 1 -C 4 -alkoxy . Examples are methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, secondary butyloxy, isobutyloxy, tertiary butyloxy, pentyloxy, hexyloxy, heptyloxy, 2,4,4- Trimethylpentyloxy, 2-ethyl-hexyloxy, octyloxy, nonyloxy, decyloxy, dodecyloxy, hexadecyloxy and octadecyloxy, in particular methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, secondary butyloxy, isobutyloxy and tertiary butyloxy, preferably methoxy.
마찬가지로, C1-C12알콕시, C1-C8알콕시, C1-C6알콕시 및 C1-C4알콕시는 직쇄 또는 측쇄이며, 예를 들면, 위에서 언급한 바와 같은 것으로서, 상응하는 탄소수를 갖는 것이다.Likewise, C 1 -C 12 alkoxy, C 1 -C 8 alkoxy, C 1 -C 6 alkoxy and C 1 -C 4 alkoxy are straight or branched chains, for example as mentioned above, To have.
C1-C12알킬티오는 직쇄 라디칼 또는 측쇄 라디칼이며, 예를 들면, C1-C8-알킬티오, C1-C6-알킬티오 또는 C1-C4-알킬티오, 예를 들면, 메틸티오, 에틸티오, 프로필티오, 이소프로필티오, n-부틸티오, 2급 부틸티오, 이소부틸티오, 3급 부틸티오, 펜틸티오, 헥실티오, 헵틸티오, 2,4,4-트리메틸펜틸티오, 2-에틸헥실티오, 옥틸티오, 노닐티오, 데실티오 또는 도데실티오, 특히 메틸티오, 에틸티오, 프로필티오, 이소프로필티오, n-부틸티오, 2급 부틸티오, 이소부틸티오 또는 3급 부틸티오, 바람직하게는 메틸티오이다. 마찬가지로, C1-C8알킬티오는 직쇄 또는 측쇄이며, 예를 들면, 위에서 언급한 바와 같은 것으로서, 상응하는 탄소수를 갖는 것이다.C 1 -C 12 alkylthio is a straight or branched radical, for example C 1 -C 8 -alkylthio, C 1 -C 6 -alkylthio or C 1 -C 4 -alkylthio, for example Methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, secondary butylthio, isobutylthio, tertiary butylthio, pentylthio, hexylthio, heptylthio, 2,4,4-trimethylpentylthio , 2-ethylhexylthio, octylthio, nonylthio, decylthio or dodecylthio, especially methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, secondary butylthio, isobutylthio or tertiary Butylthio, preferably methylthio. Likewise, C 1 -C 8 alkylthio is straight or branched, for example as mentioned above, having a corresponding carbon number.
C5-C12사이클로알킬은, 예를 들면, 사이클로펜틸, 사이클로헥실, 사이클로옥틸 또는 사이클로도데실, 특히 사이클로펜틸 또는 사이클로헥실, 바람직하게는 사이클로헥실이다.C 5 -C 12 cycloalkyl is, for example, cyclopentyl, cyclohexyl, cyclooctyl or cyclododecyl, in particular cyclopentyl or cyclohexyl, preferably cyclohexyl.
C2-C8알케닐 라디칼은 일치환 또는 다치환될 수 있고, 직쇄 또는 측쇄일 수 있으며, 예를 들면, C2-C6-알케닐 또는 C2-C4-알케닐일 수 있다. 예는 알릴, 메트알릴, 1,1-디메틸알릴, 1-부테닐, 2-부테닐, 1,3-펜타디에닐, 1-헥세닐 및 1-옥테닐, 특히 알릴이다.The C 2 -C 8 alkenyl radical may be mono- or polysubstituted and may be straight or branched chain, for example C 2 -C 6 -alkenyl or C 2 -C 4 -alkenyl. Examples are allyl, metallyl, 1,1-dimethylallyl, 1-butenyl, 2-butenyl, 1,3-pentadienyl, 1-hexenyl and 1-octenyl, especially allyl.
페닐 치환된 C1-C4알킬은 특히 벤질이다.Phenyl substituted C 1 -C 4 alkyl is especially benzyl.
치환된 페닐, 나프틸 또는 비페닐은 페닐 환이 일치환 내지 오치환, 예를 들면, 일치환, 이치환 또는 삼치환되며, 특히 일치환 또는 이치환된다. 특히, 치환된 페닐로서의 R3은 이치환 또는 삼치환된다.Substituted phenyl, naphthyl or biphenyl has a phenyl ring mono- to 5-substituted, for example mono-, di- or tri-substituted, in particular mono- or di-substituted. In particular, R 3 as substituted phenyl is di- or tri-substituted.
페닐, 나프틸 및 비페닐로서의 바람직한 치환체인 R1, R2및 R3은 C1-C4알킬, 특히 메틸, C1-C4알콕시, 특히 메톡시 및 염소이다. R3의 특히 바람직한 의미는, 예를 들면, 2,4,6-트리메틸페닐, 2,6-디메틸페닐 또는 2,6-디메톡시페닐이다.Preferred substituents as phenyl, naphthyl and biphenyl are R 1 , R 2 and R 3 which are C 1 -C 4 alkyl, in particular methyl, C 1 -C 4 alkoxy, in particular methoxy and chlorine. Particularly preferred meaning of R 3 is 2,4,6-trimethylphenyl, 2,6-dimethylphenyl or 2,6-dimethoxyphenyl, for example.
할로겐은 불소, 염소, 브롬 또는 요오드, 특히 염소 또는 브롬, 바람직하게는 염소이다.Halogen is fluorine, chlorine, bromine or iodine, in particular chlorine or bromine, preferably chlorine.
화학식 1의 화합물의 제조방법은 당해 분야의 숙련가에게 공지되어 있으며, 예를 들면, 미국 특허 제4,298,738호, 미국 특허 제4,737,593호 및 미국 특허 제4,792,632호, 영국 특허 제2,259,704호 및 WO 제96/07662호에 기재되어 있다. 이들 화합물 중의 일부는 시판되고 있다.Methods of preparing compounds of Formula 1 are known to those skilled in the art and include, for example, US Pat. No. 4,298,738, US Pat. No. 4,737,593 and US Pat. No. 4,792,632, UK Pat. No. 2,259,704 and WO 96/07662. It is described in the issue. Some of these compounds are commercially available.
또한, 화학식 2의 화합물 중의 일부도 시판되고 있다. 이들의 제조방법은 공지된 방법에 따라 수행하며, 예를 들면, 유럽 특허 제3002호, 유럽 특허 제284 561호 및 유럽 특허 제805 152호에 기재되어 있다. 화학식 2의 올리고머성 화합물의 제조방법은, 예를 들면, 유럽 특허 제161 463호에 기재되어 있다.In addition, some of the compounds of the formula (2) are also commercially available. Their preparation is carried out according to known methods and is described, for example, in European Patent No. 3002, European Patent No. 284 561 and European Patent No. 805 152. Processes for preparing oligomeric compounds of formula (2) are described, for example, in European Patent No. 161 463.
화학식 1의 화합물에서 R1및 R2가 각각 독립적으로 C1-C18알킬, 하나 이상의 연속하지 않은 산소원자에 의해 차단된 C2-C18알킬, 페닐 치환된 C1-C4알킬, C2-C8알케닐, 페닐, 나프틸, 비페닐 또는 C5-C12사이클로알킬(여기서, 페닐, 나프틸, 비페닐 및 C5-C12사이클로알킬 라디칼은 치환되지 않거나 할로겐, C1-C8알킬, C1-C8알킬티오 및/또는 C1-C8알콕시에 의해 일치환 내지 오치환된다)이고, R3이 치환되지 않거나 C1-C12알킬, C1-C12알콕시, C1-C12알킬티오 및/또는 할로겐에 의해 일치환 내지 오치환된 페닐인 조성물이 바람직하다.R 1 and R 2 in the compound of Formula 1 are each independently C 1 -C 18 alkyl, C 2 -C 18 alkyl blocked by one or more non-contiguous oxygen atoms, phenyl substituted C 1 -C 4 alkyl, C 2 -C 8 alkenyl, phenyl, naphthyl, biphenyl or C 5 -C 12 cycloalkyl, wherein the phenyl, naphthyl, biphenyl and C 5 -C 12 cycloalkyl radicals are unsubstituted or halogen, C 1- Mono- or substituted by C 8 alkyl, C 1 -C 8 alkylthio and / or C 1 -C 8 alkoxy), R 3 is unsubstituted or C 1 -C 12 alkyl, C 1 -C 12 alkoxy, Preference is given to compositions which are mono- or missubstituted phenyl with C 1 -C 12 alkylthio and / or halogen.
본 발명에 따르는 또 다른 바람직한 조성물에 있어서, 화학식 1의 화합물은 모노아실포스핀 옥사이드이다.In another preferred composition according to the invention, the compound of formula 1 is monoacylphosphine oxide.
기타 바람직한 조성물에 있어서, 화학식 1의 화합물에서의 R1및 R2는 각각 독립적으로 C1-C18알킬이거나, 치환되지 않거나 할로겐, C1-C8알킬, C1-C8알킬티오 및/또는 C1-C8알콕시에 의해 일치환 내지 오치환된 페닐이다.In other preferred compositions, R 1 and R 2 in the compound of formula 1 are each independently C 1 -C 18 alkyl, unsubstituted or halogen, C 1 -C 8 alkyl, C 1 -C 8 alkylthio and // Or phenyl mono- or missubstituted with C 1 -C 8 alkoxy.
또한, 화학식 1의 화합물에서 R3이 C1-C12알킬 또는 C1-C12알콕시에 의해 이치환 또는 삼치환된 페닐인 조성물이 유용하다.Also useful in the compounds of Formula 1 are those wherein R 3 is phenyl di- or tri-substituted by C 1 -C 12 alkyl or C 1 -C 12 alkoxy.
또 다른 바람직한 조성물은, 화학식 2의 화합물에서 R4가 수소, -OCH2CH2-OR8, 모르폴리노 또는 SCH3이고 R5가 하이드록시, C1-C16알콕시, 모르폴리노 또는 디메틸아미노이며 R6및 R7이 각각 독립적으로 C1-C6알킬, 벤질 또는 C1-C16알콕시이거나, R6및 R7이 이들이 결합되어 있는 탄소원자와 함께 사이클로헥실 환을 형성하고, 단 R5, R6및 R7이 모두 동시에 C1-C16알콕시가 아니고 R8이 수소인 조성물이다.Another preferred composition is a compound of Formula 2 wherein R 4 is hydrogen, —OCH 2 CH 2 —OR 8 , morpholino or SCH 3 and R 5 is hydroxy, C 1 -C 16 alkoxy, morpholino or dimethyl Is amino and R 6 and R 7 are each independently C 1 -C 6 alkyl, benzyl or C 1 -C 16 alkoxy, or R 6 and R 7 together with the carbon atom to which they are attached form a cyclohexyl ring, R 5 , R 6 and R 7 are not all C 1 -C 16 alkoxy at the same time and R 8 is hydrogen.
또한, 화학식 2의 화합물이 α-하이드록시케톤인 조성물이 특히 바람직하다.Also particularly preferred are compositions wherein the compound of formula 2 is α-hydroxyketone.
화학식 2의 바람직한 화합물은 α-하이드록시사이클로헥실페닐-케톤과 2-하이드록시-2-메틸-1-페닐-프로파논, (4-메틸티오벤조일)-1-메틸-1-모르폴리노-에탄, (4-모르폴리노-벤조일)-1-벤질-1-디메틸아미노-프로판 및 벤질 디메틸케탈이다.Preferred compounds of formula (2) are α-hydroxycyclohexylphenyl-ketone and 2-hydroxy-2-methyl-1-phenyl-propane, (4-methylthiobenzoyl) -1-methyl-1-morpholino- Ethane, (4-morpholino-benzoyl) -1-benzyl-1-dimethylamino-propane and benzyl dimethylketal.
화학식 1의 바람직한 화합물은 (2,4,6-트리메틸벤조일)-디페닐-포스핀 옥사이드, 비스(2,6-디메톡시벤조일)-(2,4,4-트리메틸펜트-1-일)포스핀 옥사이드, 비스(2,4,6-트리메틸벤조일)-페닐-포스핀 옥사이드 및 비스(2,4,6-트리메틸벤조일)-(2,4-디펜틸옥시페닐)포스핀 옥사이드이다.Preferred compounds of formula 1 are (2,4,6-trimethylbenzoyl) -diphenyl-phosphine oxide, bis (2,6-dimethoxybenzoyl)-(2,4,4-trimethylpent-1-yl) force Fin oxide, bis (2,4,6-trimethylbenzoyl) -phenyl-phosphine oxide and bis (2,4,6-trimethylbenzoyl)-(2,4-dipentyloxyphenyl) phosphine oxide.
화학식 2의 화합물에서 R6및 R7이 각각 독립적으로 C1-C6알킬이거나, 이들이 결합되어 있는 탄소원자와 함께 사이클로헥실 환을 형성하며 R5가 하이드록시인 조성물이 더욱 바람직하다.More preferred are compositions wherein R 6 and R 7 in the compound of formula 2 are each independently C 1 -C 6 alkyl, or together with the carbon atoms to which they are attached form a cyclohexyl ring and R 5 is hydroxy.
또한, 화학식 2의 화합물에서 R6및 R7이 동일하며, 메틸이고 R5가 하이드록시 또는 이소프로폭시인 조성물이 중요하다.Also of note are compositions in which the compounds of formula (2) are identical in which R 6 and R 7 are methyl and R 5 is hydroxy or isopropoxy.
화학식 2의 화합물과의 혼합물에서의 화학식 1의 화합물의 비율은 5 내지 99%, 예를 들면, 20 내지 80%, 바람직하게는 25 내지 75%이다.The proportion of the compound of formula 1 in the mixture with the compound of formula 2 is 5 to 99%, for example 20 to 80%, preferably 25 to 75%.
또한, 실온에서 액체인 화학식 1의 화합물과 화학식 2의 화합물과의 광 개시제 혼합물을 포함하는, 위에서 언급한 바와 같은 조성물이 유용하다.Also useful are compositions as mentioned above comprising a photoinitiator mixture of a compound of formula 1 with a compound of formula 2 that is liquid at room temperature.
본 발명에 따르는 조성물은 형광증백제를 하나 이상 포함한다. 즉, 이들은 이러한 화합물을 1개 이상, 예를 들면, 1개 또는 2개 포함한다.The composition according to the invention comprises at least one fluorescent brightener. That is, they include one or more such compounds, for example one or two.
본 발명에 따르는 조성물에 있어서, 성분(c)로서 사용하는 형광증백제는 당해 분야에서 공지된 광범위한 종류로부터 발생할 수 있다.In the compositions according to the invention, the optical brighteners used as component (c) can arise from a wide variety of types known in the art.
예를 들면, 피라졸린, 스틸벤[예: 4,4'-비스(디페닐트리아지닐)스틸벤], 트리아진, 티아졸, 벤즈옥사졸, 크산톤, 트리아졸(예: 스틸베닐-나프토트리아졸), 옥사졸[예: 비스(벤즈옥사졸-2-일) 유도체], 티오펜(예: 비스벤즈옥사졸릴-티오펜) 및 쿠마린의 그룹으로부터 발생한 형광증백제가 적합하다.For example, pyrazoline, stilbene [eg 4,4'-bis (diphenyltriazinyl) stilbene], triazine, thiazole, benzoxazole, xanthone, triazole (eg stilbenyl-naph Totriazole), oxazoles (such as bis (benzoxazol-2-yl) derivatives), thiophenes (such as bisbenzoxazolyl-thiophene) and fluorescent brighteners derived from the group of coumarins are suitable.
또 다른 예는 미국 특허 제2,784,183호와 미국 특허 제3,644,394호에서 발견할 수 있다. 또한, 예는 문헌[참조: R. L. Allen, Colour Chemistry, pages 278-286, Nelson, 1971]에 기재되어 있다. 2,2'-(티오펜디일)-비스(3급 부틸-벤즈옥사졸), 2-(스틸빌-4")-(나프토-1',2',4,5)-1,2,3-트리아졸-2"-설폰산 페닐 에스테르, 7-(4'-클로로-6"-디에틸아미노-1',3',5'-트리아진-4'-일)-아미노-3-페닐-쿠마린 및 2,5-비스(6,6'-비스(3급 부틸)-벤즈옥사졸-2-일)-티오펜이 바람직하다.Another example can be found in US Pat. No. 2,784,183 and US Pat. No. 3,644,394. Examples are also described in R. L. Allen, Color Chemistry, pages 278-286, Nelson, 1971. 2,2 '-(thiophendiyl) -bis (tert-butyl-benzoxazole), 2- (steelville-4 ")-(naphtho-1', 2 ', 4,5) -1,2 , 3-triazole-2 "-sulfonic acid phenyl ester, 7- (4'-chloro-6" -diethylamino-1 ', 3', 5'-triazin-4'-yl) -amino-3 Preferred are -phenyl-coumarin and 2,5-bis (6,6'-bis (tert butyl) -benzoxazol-2-yl) -thiophene.
형광증백제는 특히 화학식 3의 화합물이다.Fluorescent whitening agents are especially compounds of formula (3).
위의 화학식 3에서,In Formula 3 above,
X는,,,또는그룹이고,X is , , , or Group,
R9, R10, R11및 R12는 각각 독립적으로 수소, C1-C8알킬, -COO-C1-C8알킬, 특히 -COOCH3또는 -COOCH2CH(C2H5)C4H9에 의해 치환된 C1-C8알킬, -COO-C1-C20알킬 또는 α,α-디메틸벤질이다.R 9 , R 10 , R 11 and R 12 are each independently hydrogen, C 1 -C 8 alkyl, -COO-C 1 -C 8 alkyl, in particular -COOCH 3 or -COOCH 2 CH (C 2 H 5 ) C C 1 -C 8 alkyl, —COO-C 1 -C 20 alkyl or α, α-dimethylbenzyl substituted by 4 H 9 .
X가,,,또는그룹이고, R9, R10, R11및 R12가 각각 독립적으로 수소, 메틸, 3급 부틸, -COO-C1-C20알킬 또는 α,α-디메틸벤질인 화학식 3의 화합물이 바람직하다.X , , , or Preference is given to compounds of the formula (3) wherein R 9 , R 10 , R 11 and R 12 are each independently hydrogen, methyl, tertiary butyl, -COO-C 1 -C 20 alkyl or α, α-dimethylbenzyl .
와(여기서, R15는 CH3또는 CH2CH(CH3)CH2CH3이다)가 특히 바람직하다. Wow Particularly preferred is wherein R 15 is CH 3 or CH 2 CH (CH 3 ) CH 2 CH 3 .
또 다른 바람직한 형광증백제 화합물은,,및이다.Another preferred fluorescent brightener compound is , , And to be.
형광증백제 화합물은 당해 분야의 숙련가에게 공지되어 있으며, 예를 들면, 스위스의 시바 스페치알리테텐케미사의 "UVITEX" 상표로 널리 시판되고 있다.RUVITEX OB(스위스, 시바 스페치알리테텐케미사 제조)가 특히 바람직하다.Fluorescent brightener compounds are known to those skilled in the art and are widely marketed, for example, under the "UVITEX" trademark of Ciba Spepeliteitetenchemis, Switzerland. Particularly preferred is R UVITEX OB (Switzerland, manufactured by Ciba Sp.
형광증백제(c)는, 유리하게는 0.05 내지 2.0%, 바람직하게는 0.2 내지 1.0%의 양으로 본 발명에 따르는 조성물에 첨가된다.Fluorescent whitening agent (c) is advantageously added to the composition according to the invention in an amount of 0.05 to 2.0%, preferably 0.2 to 1.0%.
성분(b)로서 R1및 R2가 페닐이고, R3이 C1-C4알킬 치환된 페닐인 화학식 1의 화합물을 포함하거나, 성분(b)로서 R1및 R2가 페닐이고, R3이 C1-C4알킬 치환된 페닐인 화학식 1의 화합물과 R4가 수소이고, R5가 하이드록시이며, R6및 R7이 각각 C1-C4알킬이거나, 함께 사이클로헥실 환을 형성하는 화학식 2의 화합물과의 혼합물을 포함하고, 성분(c)로서 X가라디칼이고, R10및 R12가 수소이며, R9및 R11이 각각 3급 부틸인 화학식 3의 화합물을 포함하며, 성분(d)로서 이산화티탄 안료를 포함하는 조성물이 바람직하다.Component (b) comprises R 1 and R 2 is phenyl, R 3 is C 1 -C 4 alkyl substituted phenyl, or component (b) R 1 and R 2 are phenyl, R A compound of Formula 1 wherein 3 is C 1 -C 4 alkyl substituted phenyl and R 4 is hydrogen, R 5 is hydroxy, R 6 and R 7 are each C 1 -C 4 alkyl, or together form a cyclohexyl ring Admixture with a compound of formula (2) to form wherein component (c) Preferred are compositions comprising a compound of formula (3) wherein the radical is R 10 and R 12 are hydrogen and R 9 and R 11 are tertiary butyl, respectively, and comprise titanium dioxide pigment as component (d).
RUVITEX OB및 2,4,6-트리메틸벤조일-디페닐-포스핀 옥사이드와 2-하이드록시-2-메틸-1-페닐-프로파논과의 1:1 혼합물을 포함하는 조성물,RUVITEX OB와 2,4,6-트리메틸벤조일-디페닐-포스핀 옥사이드를 포함하는 조성물,RUVITEX OB 및 (2,4,6-트리메틸벤조일)-디페닐-포스핀 옥사이드와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물을 포함하는 조성물,RUVITEX OB 및 (2,4,6-트리메틸벤조일)-에톡시-페닐-포스핀 옥사이드와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물을 포함하는 조성물, 및RUVITEX OB 및와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물을 포함하는 조성물이 특히 바람직하다. R UVITEX OB And a 1: 1 mixture of 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propanone, 2,4 with R UVITEX OB A composition comprising, 6-trimethylbenzoyl-diphenyl-phosphine oxide, R UVITEX OB and (2,4,6-trimethylbenzoyl) -diphenyl-phosphine oxide and (1-hydroxy-cyclohexyl) -phenyl Composition comprising a 1: 1 mixture with ketones, R UVITEX OB and (2,4,6-trimethylbenzoyl) -ethoxy-phenyl-phosphine oxide and (1-hydroxycyclohexyl) -phenyl-ketone A composition comprising a 1: 1 mixture with R UVITEX OB and Particular preference is given to compositions comprising a 1: 1 mixture of with (1-hydroxy-cyclohexyl) -phenyl-ketone.
불포화 화합물(a)는 올레핀성 이중결합을 1개 이상 함유할 수 있으며 저분자량(단량체성) 또는 고분자량(올리고머성)일 수 있다. 이중결합을 1개 갖는 단량체의 예는 알킬 아크릴레이트, 알킬 메타크릴레이트, 하이드록시알킬 아크릴레이트 및 하이드록시알킬 메타크릴레이트, 예를 들면, 메틸 아크릴레이트, 에틸 아크릴레이트, 부틸 아크릴레이트, 2-에틸헥실 아크릴레이트 및 2-하이드록시에틸 아크릴레이트, 이소보닐 아크릴레이트, 메틸 메타크릴레이트 및 에틸 메타크릴레이트이다. 또한, 실리콘 아크릴레이트가 유용하다. 또 다른 예는 아크릴로니트릴, 아크릴아미드, 메타크릴아미드, N-치환된 (메트)아크릴아미드, 비닐 에스테르(예: 비닐 아세테이트), 비닐 에테르(예: 이소부틸 비닐 에테르), 스티렌, 알킬-스티렌 및 할로-스티렌, N-비닐피롤리돈, 비닐 클로라이드 및 비닐리덴 클로라이드이다.The unsaturated compound (a) may contain one or more olefinic double bonds and may be of low molecular weight (monomeric) or high molecular weight (oligomeric). Examples of monomers having one double bond include alkyl acrylates, alkyl methacrylates, hydroxyalkyl acrylates and hydroxyalkyl methacrylates such as methyl acrylate, ethyl acrylate, butyl acrylate, 2- Ethylhexyl acrylate and 2-hydroxyethyl acrylate, isobornyl acrylate, methyl methacrylate and ethyl methacrylate. Silicone acrylates are also useful. Another example is acrylonitrile, acrylamide, methacrylamide, N-substituted (meth) acrylamide, vinyl esters (e.g. vinyl acetate), vinyl ethers (e.g. isobutyl vinyl ether), styrene, alkyl-styrene And halo-styrene, N-vinylpyrrolidone, vinyl chloride and vinylidene chloride.
이중결합을 여러 개 갖는 단량체의 예는 에틸렌 글리콜 디아크릴레이트, 프로필렌 글리콜 디아크릴레이트, 네오펜틸 글리콜 디아크릴레이트, 헥사메틸렌 글리콜 디아크릴레이트, 비스페놀-A 디아크릴레이트, 4,4'-비스(2-아크릴로일옥시에톡시)-디페닐프로판, 트리메틸롤프로판 트리아크릴레이트, 트리프로필렌 글리콜 디아크릴레이트, 펜타에리트리톨 트리아크릴레이트 및 테트라아크릴레이트, 비닐 아크릴레이트, 디비닐벤젠, 디비닐 석시네이트, 디알릴 프탈레이트, 트리알릴 포스페이트, 트리알릴 이소시아네이트 및 트리스(2-아크릴로일에틸)이소시아누레이트이다.Examples of monomers having multiple double bonds include ethylene glycol diacrylate, propylene glycol diacrylate, neopentyl glycol diacrylate, hexamethylene glycol diacrylate, bisphenol-A diacrylate, 4,4'-bis ( 2-acryloyloxyethoxy) -diphenylpropane, trimethylolpropane triacrylate, tripropylene glycol diacrylate, pentaerythritol triacrylate and tetraacrylate, vinyl acrylate, divinylbenzene, divinyl succinate Nate, diallyl phthalate, triallyl phosphate, triallyl isocyanate and tris (2-acryloylethyl) isocyanurate.
고분자량(올리고머성) 다불포화 화합물의 예는 아크릴화 에폭시 수지, 아크릴화 폴리에스테르, 비닐 에테르 그룹 함유 폴리에스테르, 에폭시 그룹 함유 폴리에스테르, 폴리우레탄 및 폴리에테르이다. 불포화 올리고머의 또 다른 예는 통상적으로 말레산, 프탈산 및 하나 이상의 디올로부터 제조되며 분자량이 약 500 내지 3,000인 불포화 폴리에스테르 수지이다. 또한, 비닐 에테르 단량체와 올리고머를 사용할 수 있으며, 폴리에스테르, 폴리우레탄, 폴리에테르, 폴리비닐 에테르 및 에폭사이드 주쇄를 갖는 말레에이트 말단화 올리고머도 사용할 수 있다. WO 제90/01512호에 기재되어 있는 바와 같이, 비닐 에테르 그룹 함유 올리고머와 중합체와의 배합물이 특히 적합하다. 그러나, 비닐 에테르 또는 말레산으로 관능화된 단량체의 공중합체도 적합하다. 이러한 불포화 올리고머는 예비중합체라고 할 수도 있다.Examples of high molecular weight (oligomeric) polyunsaturated compounds are acrylated epoxy resins, acrylated polyesters, vinyl ether group-containing polyesters, epoxy group-containing polyesters, polyurethanes and polyethers. Another example of an unsaturated oligomer is an unsaturated polyester resin, typically prepared from maleic acid, phthalic acid and one or more diols, having a molecular weight of about 500 to 3,000. It is also possible to use vinyl ether monomers and oligomers, as well as maleate terminated oligomers having polyester, polyurethane, polyether, polyvinyl ether and epoxide backbones. As described in WO 90/01512, combinations of vinyl ether group containing oligomers with polymers are particularly suitable. However, copolymers of monomers functionalized with vinyl ether or maleic acid are also suitable. Such unsaturated oligomers may also be referred to as prepolymers.
이들은, 예를 들면, 에틸렌성 불포화 카복실산과 폴리올 또는 폴리에폭사이드의 에스테르, 및 에틸렌성 불포화 그룹을 주쇄 그룹 또는 측쇄 그룹에 갖는 중합체(예: 불포화 폴리에스테르, 불포화 폴리아미드 및 불포화 폴리우레탄 및 이들의 공중합체, 알키드 수지, 폴리부타디엔과 부타디엔 공중합체, 폴리이소프렌과 이소프렌 공중합체), (메트)아크릴산 그룹을 측쇄에 갖는 중합체와 공중합체, 및 하나 이상의 이들 중합체의 혼합물이 특히 적합하다.These include, for example, esters of ethylenically unsaturated carboxylic acids and polyols or polyepoxides, and polymers having ethylenically unsaturated groups in the main or side chain groups (e.g. unsaturated polyesters, unsaturated polyamides and unsaturated polyurethanes and Copolymers, alkyd resins, polybutadiene and butadiene copolymers, polyisoprene and isoprene copolymers), polymers and copolymers having (meth) acrylic acid groups in the side chain, and mixtures of one or more of these polymers are particularly suitable.
불포화 카복실산의 예는 아크릴산, 메타크릴산, 크로톤산, 이타콘산, 신남산 및 불포화 지방산(예: 리놀렌산 또는 올레산)이다. 아크릴산과 메타크릴산이 바람직하다.Examples of unsaturated carboxylic acids are acrylic acid, methacrylic acid, crotonic acid, itaconic acid, cinnamic acid and unsaturated fatty acids such as linolenic acid or oleic acid. Acrylic acid and methacrylic acid are preferred.
적합한 폴리올은 방향족 폴리올, 특히 지방족 폴리올 및 지환족 폴리올이다. 방향족 폴리올의 예는 하이드로퀴논, 4,4'-디하이드록시디페닐 및 2,2-디(4-하이드록시페닐)-프로판을 포함하며, 노볼락과 레졸도 포함한다. 폴리에폭사이드의 예는 위에서 언급한 폴리올계 에폭사이드, 특히 방향족 폴리올계 에폭사이드와 에피클로로히드린계 에폭사이드이다. 또한, 폴리올로서 적합한 것은 하이드록시 그룹을 중합체 쇄 그룹 또는 측쇄 그룹에 함유하는 중합체 및 공중합체(예: 폴리비닐 알콜 및 이들의 공중합체와 폴리메타크릴산 하이드록시알킬 에스테르 및 이들의 공중합체)가 적합하다. 또 다른 적합한 폴리올은 말단 하이드록시 그룹을 갖는 올리고에스테르이다.Suitable polyols are aromatic polyols, in particular aliphatic polyols and cycloaliphatic polyols. Examples of aromatic polyols include hydroquinone, 4,4'-dihydroxydiphenyl and 2,2-di (4-hydroxyphenyl) -propane, as well as novolacs and resols. Examples of polyepoxides are the polyol epoxides mentioned above, in particular aromatic polyol epoxides and epichlorohydrin epoxides. Also suitable as polyols are polymers and copolymers containing hydroxy groups in the polymer chain group or the side chain group, such as polyvinyl alcohol and copolymers thereof and polymethacrylic acid hydroxyalkyl esters and copolymers thereof. Suitable. Another suitable polyol is an oligoester having terminal hydroxy groups.
지방족 폴리올과 지환족 폴리올의 예는, 바람직하게는 탄소수 2 내지 12의 알킬렌디올, 예를 들면, 에틸렌 글리콜, 1,2-프로판디올, 1,3-프로판디올, 1,2-부탄디올, 1,3-부탄디올, 1,4-부탄디올, 펜탄디올, 헥산디올, 옥탄디올, 도데칸디올, 디에틸렌 글리콜, 트리에틸렌 글리콜, 분자량이 바람직하게는 200 내지 1,500인 폴리에틸렌 글리콜, 1,3-사이클로펜탄디올, 1,2-사이클로헥산디올, 1,3-사이클로헥산디올, 1,4-사이클로헥산디올, 1,4-디하이드록시메틸사이클로헥산, 글리세롤, 트리스(β-하이드록시에틸)아민, 트리메틸롤에탄, 트리메틸롤프로판, 펜타에리트리톨, 디펜타에리트리톨 및 소르비톨을 포함한다.Examples of aliphatic polyols and alicyclic polyols are preferably alkylenediols having 2 to 12 carbon atoms, for example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1 , 3-butanediol, 1,4-butanediol, pentanediol, hexanediol, octanediol, dodecanediol, diethylene glycol, triethylene glycol, polyethylene glycol having a molecular weight of preferably 200 to 1,500, 1,3-cyclopentane Diol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,4-dihydroxymethylcyclohexane, glycerol, tris (β-hydroxyethyl) amine, trimethyl Rollethane, trimethylolpropane, pentaerythritol, dipentaerythritol and sorbitol.
폴리올은 한 가지 또는 여러 가지 불포화 카복실산에 의해 부분적으로 또는 완전히 에스테르화될 수 있으며, 부분 에스테르 중의 유리 하이드록시 그룹은 개질시킬 수 있으며, 예를 들면, 에테르화되거나, 기타 카복실산에 의해 에스테르화될 수 있다.The polyols can be partially or fully esterified with one or several unsaturated carboxylic acids and the free hydroxy groups in the partial esters can be modified, for example etherified or esterified with other carboxylic acids. have.
에스테르의 예는 다음과 같다:Examples of esters are as follows:
트리메틸롤프로판 트리아크릴레이트, 트리메틸롤에탄 트리아크릴레이트, 트리메틸롤프로판 트리메타크릴레이트, 트리프로필렌 글리콜 디아크릴레이트, 트리메틸롤에탄 트리메타크릴레이트, 테트라메틸렌 글리콜 디메타크릴레이트, 트리에틸렌 글리콜 디메타크릴레이트, 테트라에틸렌 글리콜 디아크릴레이트, 펜타에리트리톨 디아크릴레이트, 펜타에리트리톨 트리아크릴레이트, 펜타에리트리톨 테트라아크릴레이트, 디펜타에리트리톨 디아크릴레이트, 디펜타에리트리톨 트리아크릴레이트, 디펜타에리트리톨 테트라아크릴레이트, 디펜타에리트리톨 펜타아크릴레이트, 디펜타에리트리톨 헥사아크릴레이트, 트리펜타에리트리톨 옥타아크릴레이트, 펜타에리트리톨 디메타크릴레이트, 펜타에리트리톨 트리메타크릴레이트, 디펜타에리트리톨 디메타크릴레이트, 디펜타에리트리톨 테트라메타크릴레이트, 트리펜타에리트리톨 옥타메타크릴레이트, 펜타에리트리톨 디이타코네이트, 디펜타에리트리톨 트리스이타코네이트, 디펜타에리트리톨 펜타이타코네이트, 디펜타에리트리톨 헥사이타코네이트, 에틸렌 글리콜 디아크릴레이트, 1,3-부탄디올 디아크릴레이트, 1,3-부탄디올 디메타크릴레이트, 1,4-부탄디올 디이타코네이트, 소르비톨 트리아크릴레이트, 소르비톨 테트라아크릴레이트, 펜타에리트리톨-개질된 트리아크릴레이트, 소르비톨 테트라메타크릴레이트, 소르비톨 펜타아크릴레이트, 소르비톨 헥사아크릴레이트, 올리고에스테르 아크릴레이트, 올리고에스테르 메타크릴레이트, 글리세롤 디아크릴레이트, 글리세롤 트리아크릴레이트, 1,4-사이클로헥산 디아크릴레이트, 비스아크릴레이트 및 분자량이 200 내지 1,500인 폴리에틸렌 글리콜의 비스메타크릴레이트, 및 이들의 혼합물.Trimethylolpropane triacrylate, trimethylolethane triacrylate, trimethylolpropane trimethacrylate, tripropylene glycol diacrylate, trimethylolethane trimethacrylate, tetramethylene glycol dimethacrylate, triethylene glycol dimethacrylate Acrylate, tetraethylene glycol diacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythrate Lithol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, tripentaerythritol octaacrylate, pentaerythritol dimethacrylate, pentaerythritol trimethacrylate, dipentaerythritol dimethacrylate Methacrylate, dipentaerythritol tetramethacrylate, tripentaerythritol octamethacrylate, pentaerythritol diitaconate, dipentaerythritol trisitaconate, dipentaerythritol pentaitaconate, dipentaerythritol hextacoate Nate, ethylene glycol diacrylate, 1,3-butanediol diacrylate, 1,3-butanediol dimethacrylate, 1,4-butanediol diitaconate, sorbitol triacrylate, sorbitol tetraacrylate, pentaerythritol- Modified triacrylate, sorbitol tetramethacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, oligoester acrylate, oligoester methacrylate, glycerol diacrylate, glycerol triacrylate, 1,4-cyclohexane di Acrylates, bisacrylates and Jaryang bis methacrylate, and mixtures of the polyethylene glycol is 200 to 1,500.
또한, 성분(a)로서, 바람직하게는 2 내지 6개, 특히 2 내지 4개의 아미노 그룹을 갖는 방향족, 지환족 및 지방족 폴리아민의 동일하거나 상이한 불포화 카복실산 아미드가 적합하다. 이러한 폴리아민의 예는 에틸렌디아민, 1,2-프로필렌디아민, 1,3-프로필렌디아민, 1,2-부틸렌디아민, 1,3-부틸렌디아민, 1,4-부틸렌디아민, 1,5-펜틸렌디아민, 1,6-헥실렌디아민, 옥틸렌디아민, 도데실렌디아민, 1,4-디아미노-사이클로헥산, 이소포론디아민, 페닐렌디아민, 비스페닐렌디아민, 디-β-아미노에틸 에테르, 디에틸렌트리아민, 트리에틸렌테트라아민, 디(β-아미노에톡시)-에탄 및 디(β-아미노프로폭시)-에탄이다. 또 다른 적합한 폴리아민은 측쇄에 아미노 그룹을 추가로 가질 수 있는 중합체 및 공중합체와 말단 아미노 그룹을 갖는 올리고아미드이다. 이러한 불포화 아미드의 예는 메틸렌 비스아크릴아미드, 1,6-헥사메틸렌 비스아크릴아미드, 디에틸렌트리아민 트리스메타크릴아미드, 비스(메타크릴아미도프로폭시)에탄, β-메타크릴-아미도에틸메타크릴레이트 및 N-[(β-하이드록시에톡시)에틸]아크릴아미드이다.Also suitable as component (a) are the same or different unsaturated carboxylic acid amides of aromatic, cycloaliphatic and aliphatic polyamines which preferably have 2 to 6, especially 2 to 4 amino groups. Examples of such polyamines are ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,2-butylenediamine, 1,3-butylenediamine, 1,4-butylenediamine, 1,5- Pentylenediamine, 1,6-hexylenediamine, octylenediamine, dodecylenediamine, 1,4-diamino-cyclohexane, isophoronediamine, phenylenediamine, bisphenylenediamine, di-β-aminoethyl ether , Diethylenetriamine, triethylenetetraamine, di (β-aminoethoxy) -ethane and di (β-aminopropoxy) -ethane. Still other suitable polyamines are oligoamides having terminal amino groups and polymers and copolymers which may further have amino groups in the side chain. Examples of such unsaturated amides are methylene bisacrylamide, 1,6-hexamethylene bisacrylamide, diethylenetriamine trismethacrylamide, bis (methacrylamidopropoxy) ethane, β-methacryl-amidoethylmetha Acrylate and N-[(β-hydroxyethoxy) ethyl] acrylamide.
적합한 불포화 폴리에스테르와 폴리아미드는, 예를 들면, 말레산과 디올 또는 디아민으로부터 유도된다. 말레산은 부분적으로 다른 디카복실산으로 대체될 수 있다. 이들은 에틸렌성 불포화 공단량체, 예를 들면, 스티렌과 함께 사용할 수 있다. 또한, 폴리에스테르와 폴리아미드는, 디카복실산과 에틸렌성 불포화 디올 또는 에틸렌성 불포화 디아민, 특히, 예를 들면, 탄소수 6 내지 20의 장쇄를 갖는 화합물로부터 유도할 수 있다. 폴리우레탄의 예는 포화 디이소시아네이트 또는 불포화 디이소시아네이트와 불포화 디올 또는 포화 디올로 구성된 화합물이다.Suitable unsaturated polyesters and polyamides are derived, for example, from maleic acid and diols or diamines. Maleic acid may be partially replaced by other dicarboxylic acids. These can be used together with ethylenically unsaturated comonomers, for example styrene. Polyesters and polyamides can also be derived from dicarboxylic acids and ethylenically unsaturated diols or ethylenically unsaturated diamines, in particular compounds having, for example, long chains of 6 to 20 carbon atoms. Examples of polyurethanes are compounds composed of saturated diisocyanates or unsaturated diisocyanates and unsaturated diols or saturated diols.
폴리부타디엔과 폴리이소프렌 및 이들의 공중합체는 공지되어 있다. 적합한 공단량체는, 예를 들면, 올레핀[예: 에틸렌, 프로펜, 부텐, 헥센, (메트)아크릴레이트, 아크릴로니트릴, 스티렌 및 비닐 클로라이드]을 포함한다. 마찬가지로, 측쇄에 (메트)아크릴레이트 그룹을 갖는 중합체는 공지되어 있다. 예는 노볼락계 에폭시 수지와 (메트)아크릴산과의 반응 생성물, (메트)아크릴산으로 에스테르화된 비닐 알콜 또는 이의 하이드록시알킬 유도체의 단독중합체 또는 공중합체 및 하이드록시알킬(메트)아크릴레이트로 에스테르화된 (메트)아크릴레이트의 단독중합체 또는 공중합체이다.Polybutadiene and polyisoprene and copolymers thereof are known. Suitable comonomers include, for example, olefins such as ethylene, propene, butene, hexene, (meth) acrylate, acrylonitrile, styrene and vinyl chloride. Likewise, polymers having (meth) acrylate groups in the side chain are known. Examples are reaction products of novolac epoxy resins with (meth) acrylic acid, homopolymers or copolymers of vinyl alcohols or hydroxyalkyl derivatives thereof esterified with (meth) acrylic acid and esters with hydroxyalkyl (meth) acrylates Homopolymers or copolymers of ized (meth) acrylates.
광 중합 가능한 화합물은 그 자체로 또는 임의의 목적하는 혼합물의 형태로 사용할 수 있다. 바람직하게는, 폴리올(메트)아크릴레이트의 혼합물을 사용한다.The photopolymerizable compounds can be used on their own or in the form of any desired mixtures. Preferably a mixture of polyol (meth) acrylates is used.
또한, 결합제는 본 발명에 따르는 조성물에 첨가할 수 있으며, 광 중합 가능한 화합물이 액체 또는 점성 물질인 경우, 특히 편리하다. 결합제의 양은, 고체의 전체 중량을 기준으로 하여, 예를 들면, 5 내지 95중량%, 바람직하게는 10 내지 90중량%, 특히 40 내지 90중량%일 수 있다. 결합제는 기판에 대한 접착력과 산소에 대한 감도와 같은, 사용 분야와 이에 대해 요구되는 특성에 따라 선택된다.In addition, the binder may be added to the composition according to the invention, which is particularly convenient when the photopolymerizable compound is a liquid or viscous material. The amount of binder may be, for example, from 5 to 95% by weight, preferably from 10 to 90% by weight, in particular from 40 to 90% by weight, based on the total weight of the solid. The binder is selected according to the field of use and the properties required for it, such as adhesion to the substrate and sensitivity to oxygen.
적합한 결합제는, 예를 들면, 분자량이 약 5,000 내지 2,000,000, 바람직하게는 10,000 내지 1,000,000인 중합체이다. 예는 다음과 같다: 아크릴레이트와 메타크릴레이트의 단독중합체와 공중합체[예: 메틸 메타크릴레이트/에틸 아크릴레이트/메타크릴산의 공중합체, 폴리(메타크릴산 알킬 에스테르), 폴리(아크릴산 알킬 에스테르)], 셀룰로즈 에스테르와 에테르(예: 셀룰로즈 아세테이트, 셀룰로즈 아세테이트 부티레이트, 메틸셀룰로즈, 에틸셀룰로즈), 폴리비닐부티랄, 폴리비닐포르말, 폐환 고무, 폴리에테르(예: 폴리에틸렌 옥사이드, 폴리프로필렌 옥사이드, 폴리테트라하이드로푸란), 폴리스티렌, 폴리카보네이트, 폴리우레탄, 염소화 폴리올레핀, 폴리비닐 클로라이드, 비닐 클로라이드/비닐리덴 클로라이드의 공중합체, 비닐리덴 클로라이드와 아크릴로니트릴, 메틸 메타크릴레이트 및 비닐 아세테이트와의 공중합체, 폴리비닐 아세테이트, 코폴리(에틸렌/비닐 아세테이트), 중합체[예: 폴리카프롤락탐과 폴리(헥사메틸렌 아디프아미드)], 폴리에스테르[예: 폴리(에틸렌 글리콜 테레프탈레이트)와 폴리(헥사메틸렌 글리콜 석시네이트)].Suitable binders are, for example, polymers having a molecular weight of about 5,000 to 2,000,000, preferably 10,000 to 1,000,000. Examples are: homopolymers and copolymers of acrylates and methacrylates [e.g. copolymers of methyl methacrylate / ethyl acrylate / methacrylic acid, poly (methacrylic acid alkyl esters), poly (alkyl acrylates) Esters), cellulose esters and ethers (e.g. cellulose acetate, cellulose acetate butyrate, methylcellulose, ethylcellulose), polyvinylbutyral, polyvinylformal, ring closure rubber, polyethers (e.g. polyethylene oxide, polypropylene oxide, Polytetrahydrofuran), polystyrene, polycarbonate, polyurethane, chlorinated polyolefin, polyvinyl chloride, copolymer of vinyl chloride / vinylidene chloride, vinylidene chloride and copolymer of acrylonitrile, methyl methacrylate and vinyl acetate , Polyvinyl acetate, copoly (ethylene / vinyl Three Tate), polymers [e.g., poly-caprolactam and poly (hexamethylene adipamide), polyester [e.g., poly (ethylene glycol terephthalate) and poly (hexamethylene glycol succinate).
또한, 불포화 화합물은 광 중합되지 않은 막 형성 성분과의 혼합물에서 사용할 수 있다. 이들은, 예를 들면, 물리적으로 건조될 수 있는 중합체 또는 유기 용매 중의 이들의 용액(예: 니트로셀룰로즈 또는 셀룰로즈 아세토부티레이트)일 수 있다. 그러나, 달리, 이들은 화학 또는 열 경화성 수지(예: 폴리이소시아네이트, 폴리에폭사이드 또는 멜라민 수지)일 수 있다. 열 경화성 수지의 수반되는 용도는 소위 혼성 시스템에서 사용하는 데 중요하며, 이는 제1 단계에서 광 중합되고 제2 단계에서 열적 후처리에 의해 가교결합된다.Unsaturated compounds can also be used in mixtures with film forming components that are not photopolymerized. These can be, for example, polymers that can be physically dried or their solutions in organic solvents such as nitrocellulose or cellulose acetobutyrate. Alternatively, however, they may be chemical or thermosetting resins such as polyisocyanates, polyepoxides or melamine resins. The concomitant use of thermosetting resins is important for use in so-called hybrid systems, which are photopolymerized in the first stage and crosslinked by thermal workup in the second stage.
어떤 결합제도 포함하지 않는 조성물이 바람직하다.Preference is given to compositions which do not contain any binder.
또한, 본 발명에 따르는 조성물은, 예를 들면, 문헌[참조: Lehrbuch der Lacke und Beschichtungen, Volume Ⅲ, 296-328, W.A. Colomb of Heenemann GmbH, Berlin-Oberschwandorf (1976)]에 기재되어 있는 바와 같이, 산화시켜 건조시키는 시스템에서 적합하다.In addition, compositions according to the invention are described, for example, in Lehrbuch der Lacke und Beschichtungen, Volume III, 296-328, W.A. Colomb of Heenemann GmbH, Berlin-Oberschwandorf (1976), suitable for oxidizing and drying systems.
본 발명에 따르는 조성물은 1개 이상의 안료(d)를 포함한다. 즉, 이들은 1개의 안료 또는 2개 이상의 상이한 안료, 예를 들면, 1 내지 3개 또는 1 또는 2개의 안료를 포함한다. 본 발명에 따르는 조성물에 있어서, 안료는 무기 안료 또는 유기 안료일 수 있다. 흑색, 백색 또는 착색된 안료를 사용할 수 있다. 안료의 예는 루틸형(rutile type) 백색 안료(예:RRTC-2, 티옥사이드 제조), 카본 블랙(예: 스페셜 블랙 250, 데구사 제조), 디케토피롤로-피롤(예:RIRGAZIN DPP Red Bo, 시바 스페셜티 케미칼즈 제조), 이소인돌리논(예:RIRGAZIN Yellow 3RLTN, 시바 스페셜티 케미칼즈 제조), 아릴아미드(예:RIRGALITE Yellow Gu, 시바 스페셜티 케미칼즈 제조), 구리 프탈로시아닌(예:RIRGALITE Blue GLNF, 시바 스페셜티 케미칼즈 제조) 및 구리 프탈로시아닌(할로겐화)(예:RIRGALITE Green GLNnew, 시바 스페셜티 케미칼즈 제조)를 포함한다.The composition according to the invention comprises at least one pigment (d). That is, they comprise one pigment or two or more different pigments, for example one to three or one or two pigments. In the composition according to the invention, the pigment may be an inorganic pigment or an organic pigment. Black, white or colored pigments can be used. Examples of pigments include rutile type white pigments (e.g. R RTC-2, manufactured by Tioxide), carbon black (e.g. Special Black 250, manufactured by Degussa), diketopyrrolo-pyrrole (e.g. R IRGAZIN DPP Red Bo, manufactured by Ciba Specialty Chemicals), isoindolinone (e.g. R IRGAZIN Yellow 3RLTN, manufactured by Ciba Specialty Chemicals), arylamides (e.g. R IRGALITE Yellow Gu, manufactured by Ciba Specialty Chemicals), copper phthalocyanine (e.g. : R IRGALITE Blue GLNF, manufactured by Ciba Specialty Chemicals) and copper phthalocyanine (halogenated) such as R IRGALITE Green GLNnew, manufactured by Ciba Specialty Chemicals.
본 발명에 따르는 조성물에 있어서, 성분(d)로서, 예를 들면, 이산화티탄형 백색 안료를 사용하는 것이 바람직하다.In the composition according to the invention, it is preferable to use, for example, titanium dioxide type white pigment as component (d).
본 발명에 따르는 광 중합 가능한 조성물은 통상적으로 안료 또는 안료들을 5 내지 50%, 예를 들면, 10 내지 50%의 양으로 함유한다.Photopolymerizable compositions according to the invention typically contain a pigment or pigments in an amount of from 5 to 50%, for example from 10 to 50%.
광 중합 가능한 혼합물은 광 개시제 이외에 각종 첨가제를 포함할 수 있다. 첨가제의 예는 미성숙 중합을 방지하는 데 사용되는 열 억제제, 예를 들면, 하이드로퀴논, 하이드로퀴논 유도체, p-메톡시페놀, β-나프톨 또는 입체 장애 페놀[예: 2,6-디(3급 부틸)-p-크레졸]이다. 암실 속에서 저장 안정성을 증가시키기 위해, 예를 들면, 구리 화합물(예: 구리 나프테네이트, 스테아레이트 또는 옥토에이트), 인 화합물(예: 트리페닐포스핀, 트리부틸포스핀, 트리에틸 포스파이트, 트리페닐 포스파이트 또는 트리벤질 포스파이트), 4급 암모늄 화합물(예: 테트라메틸암모늄 클로라이드 또는 트리메틸벤질암모늄 클로라이드) 또는 하이드록실아민 유도체(예: N-디에틸하이드록실아민)를 사용할 수 있다. 중합 도중에 대기 산소를 차단할 목적으로, 중합체에 불용성이며 중합을 개시할 때 표면으로 이동하여 공기 유입을 방지하는 투명한 표면 층을 형성하는 파라핀 또는 유사한 왁스형 물질을 첨가할 수 있다. 이와 동시에, 산소에 대해 투과성이 없는 층을 적용하는 것이 가능하다. UV 흡수제(예: 하이드록시페닐벤조트리아졸, 하이드록시페닐벤조페논, 옥살산 아미드 또는 하이드록시페닐-s-트리아진형 흡수제를 광 안정화제로서 첨가할 수 있다. 이들 화합물은 그 자체로 또는 혼합물의 형태로 입체 장애 아민(HALS)의 존재 또는 부재하에 사용할 수 있다.The photopolymerizable mixture may include various additives in addition to the photoinitiator. Examples of additives are heat inhibitors used to prevent immature polymerization, for example hydroquinone, hydroquinone derivatives, p-methoxyphenol, β-naphthol or sterically hindered phenols [eg 2,6-di (tertiary) Butyl) -p-cresol]. To increase storage stability in the dark, for example, copper compounds (eg copper naphthenate, stearate or octoate), phosphorus compounds (eg triphenylphosphine, tributylphosphine, triethyl phosphite , Triphenyl phosphite or tribenzyl phosphite), quaternary ammonium compounds (eg tetramethylammonium chloride or trimethylbenzylammonium chloride) or hydroxylamine derivatives (eg N-diethylhydroxylamine) can be used. For the purpose of blocking atmospheric oxygen during the polymerization, paraffin or similar waxy materials may be added that are insoluble in the polymer and form a transparent surface layer that migrates to the surface at the start of the polymerization and prevents air ingress. At the same time, it is possible to apply a layer which is not permeable to oxygen. UV absorbers such as hydroxyphenylbenzotriazole, hydroxyphenylbenzophenone, oxalic acid amide or hydroxyphenyl-s-triazine type absorbers may be added as light stabilizers, these compounds by themselves or in the form of mixtures. And sterically hindered amines (HALS).
이러한 UV 흡수재와 광 안정화제의 예는 다음과 같다:Examples of such UV absorbers and light stabilizers are as follows:
1.2-(2'하이드록시페닐)-벤조트리아졸, 예를 들면, 2-(2'-하이드록시-5'-메틸페닐)-벤조트리아졸, 2-(3',5'-디-3급 부틸-2'-하이드록시페닐)-벤조트리아졸, 2-(5'-3급 부틸-2'-하이드록시페닐)-벤조트리아졸, 2-(2'-하이드록시-5'-(1,1,3,3-테트라메틸부틸)페닐)-벤조트리아졸, 2-(3',5'-디-3급 부틸-2'-하이드록시페닐)-5-클로로벤조트리아졸, 2-(3'-3급 부틸-2'-하이디드록시-5'-메틸페닐)-5-클로로벤조트리아졸, 2-(3'-2급 부틸-5'-3급 부틸-2'-하이드록시페닐)-벤조트리아졸, 2-(2'-하이드록시-4'-옥틸옥시페닐)-벤조트리아졸, 2-(3',5'-디-3급 아밀-2'-하이드록시페닐)-벤조트리아졸, 2-(3',5'-비스(α,α-디메틸벤질)-2'-하이드록시페닐)-벤조트리아졸, 2-(3'-3급 부틸-2'-하이드록시-5'-(2-옥틸옥시카보닐에틸)페닐)-5-클로로벤조트리아졸, 2-(3'-3급 부틸-5'-[2-(2-에틸헥실옥시)-카보닐에틸]-2'-하이드록시페닐)-5-클로로-벤조트리아졸, 2-(3'-3급 부틸-2'-하이드록시-5'-(2-메톡시카보닐에틸)페닐)-5-클로로벤조트리아졸, 2-(3'-3급 부틸-2'-하이드록시-5'-(2-메톡시카보닐에틸)페닐)-벤조트리아졸, 2-(3'-3급 부틸-2'-하이드록시-5'-(2-옥틸옥시카보닐에틸)페닐)-벤조트리아졸, 2-(3'-3급 부틸-5'-[2-(2-에틸헥실옥시)카보닐에틸]-2'-하이드록시페닐)-벤조트리아졸, 2-(3'-도데실-2'-하이드록시-5'-메틸페닐)-벤조트리아졸 및 2-(3'-3급 부틸-2'-하이드록시-5'-(2-이소옥틸옥시카보닐에틸)페닐)-벤조트리아졸과의 혼합물, 2,2'-메틸렌-비스[4-(1,1,3,3-테트라메틸부틸)-6-벤조트리아졸-2-일-페놀], 2-[3'-3급 부틸-5'-(2-메톡시카보닐에틸)-2'-하이드록시페닐]-벤조트리아졸과 폴리에틸렌 글리콜 300과의 트랜스에스테르화 생성물, [R-CH2CH2-COO(CH2)3]2(여기서, R은 3'-3급 부틸-4'-하이드록시-5'-2H-벤조트리아졸-2-일-페닐이다).1.2- (2'hydroxyphenyl) -benzotriazole, for example 2- (2'-hydroxy-5'-methylphenyl) -benzotriazole, 2- (3 ', 5'-di-tertiary Butyl-2'-hydroxyphenyl) -benzotriazole, 2- (5'-tertiary butyl-2'-hydroxyphenyl) -benzotriazole, 2- (2'-hydroxy-5 '-(1 , 1,3,3-tetramethylbutyl) phenyl) -benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-tert-Butyl-2'-hydrodioxy-5'-methylphenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-5'-tert-butyl-2'-hydroxy Phenyl) -benzotriazole, 2- (2'-hydroxy-4'-octyloxyphenyl) -benzotriazole, 2- (3 ', 5'-di-tert amyl-2'-hydroxyphenyl) -Benzotriazole, 2- (3 ', 5'-bis (α, α-dimethylbenzyl) -2'-hydroxyphenyl) -benzotriazole, 2- (3'-tert-butyl-2'-hydride Oxy-5 '-(2-octyloxycarbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3'-tert butyl-5'-[2- (2-ethylhexyloxy) -carbo Nylethyl] -2'-Hyde Cyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '-(2-methoxycarbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '-(2-methoxycarbonylethyl) phenyl) -benzotriazole, 2- (3'-tert-butyl-2'-hydroxy -5 '-(2-octyloxycarbonylethyl) phenyl) -benzotriazole, 2- (3'-tert-butyl-5'-[2- (2-ethylhexyloxy) carbonylethyl] -2 '-Hydroxyphenyl) -benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5'-methylphenyl) -benzotriazole and 2- (3'-tert-butyl-2'-hydroxy Mixture with oxy-5 '-(2-isooctyloxycarbonylethyl) phenyl) -benzotriazole, 2,2'-methylene-bis [4- (1,1,3,3-tetramethylbutyl)- 6-benzotriazol-2-yl-phenol], 2- [3'-tert-butyl-5 '-(2-methoxycarbonylethyl) -2'-hydroxyphenyl] -benzotriazole and polyethylene glycol Transesterification product with 300, [R—CH 2 CH 2 —COO (CH 2 ) 3 ] 2 , wherein R is 3′-tert-butyl-4′-hydroxy-5′-2 H-benzotriazol-2-yl-phenyl).
2. 2-하이드록시벤조페논, 예를 들면, 4-하이드록시, 4-메톡시, 4-옥틸옥시, 4-데실옥시, 4-도데실옥시, 4-벤질옥시, 4,2',4'-트리하이드록시 또는 2'-하이드록시-4,4'-디메톡시 유도체.2. 2-hydroxybenzophenones such as 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy or 2'-hydroxy-4,4'-dimethoxy derivative.
3. 치환되지 않거나 치환된 벤조산의 에스테르, 예를 들면, 4-3급 부틸-페닐 살리실레이트, 페닐 살리실레이트, 옥틸페닐 살리실레이트, 디벤조일레조시놀, 비스(4-3급 부틸벤조일)레조시놀, 벤조일레조시놀, 3,5-디-3급 부틸-4-하이드록시벤조산 2,4-디-3급 부틸페닐 에스테르, 3,5-디-3급 부틸-4-하이드록시벤조산 헥사데실 에스테르, 3,5-디-3급 부틸-4-하이드록시벤조산 옥타데실 에스테르 및 3,5-디-3급 부틸-4-하이드록시벤조산 2-메틸-4,6-디-3급 부틸페닐 에스테르.3. Esters of unsubstituted or substituted benzoic acid, for example, 4-tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylesinosinol, bis (4-tert-butyl) Benzoyl) resorcinol, benzoyl resorcinol, 3,5-di-tert-butyl-4-hydroxybenzoic acid 2,4-di-tert-butylbutyl ester, 3,5-di-tert-butyl-4- Hydroxybenzoic acid hexadecyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid octadecyl ester and 3,5-di-tert-butyl-4-hydroxybenzoic acid 2-methyl-4,6-di Tertiary butylphenyl ester.
4. 아크릴레이트, 예를 들면, α-시아노-β,β-디페닐아크릴산 에틸 에스테르 또는 이소옥틸 에스테르, α-메톡시카보닐신남산 메틸 에스테르, α-시아노-β-메틸-p-메톡시-신남산 메틸 에스테르 또는 부틸 에스테르, α-메톡시카보닐-p-메톡시-신남산 메틸 에스테르 및 N-(β-메톡시카보닐-β-시아노비닐)-2-메틸-인돌린.4. acrylates such as α-cyano-β, β-diphenylacrylic acid ethyl ester or isooctyl ester, α-methoxycarbonylcinnamic acid methyl ester, α-cyano-β-methyl-p-meth Oxy-cinnamic acid methyl ester or butyl ester, α-methoxycarbonyl-p-methoxy-cinnamic acid methyl ester and N- (β-methoxycarbonyl-β-cyanovinyl) -2-methyl-indolin .
5. 입체 장애 아민, 예를 들면, 비스(2,2,6,6-테트라메틸피페리딜)세바케이트, 비스-(2,2,6,6-테트라메틸피페리딜)석시네이트, 비스(1,2,2,6,6-펜타메틸피페리딜)세바케이트, n-부틸-3,5-디-3급 부틸-4-하이드록시벤질말론산 비스(1,2,2,6,6-펜타메틸피페리딜)에스테르, 1-하이드록시에틸-2,2,6,6-테트라메틸-4-하이드록시피페리딘과 석신산과의 축합 생성물, N,N'-비스(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌디아민과 4-3급 옥틸아미노-2,6-디클로로-1,3,5-s-트리아진과의 축합 생성물, 트리스(2,2,6,6-테트라메틸-4-피페리딜)니트릴로트리아세테이트, 테트라키스(2,2,6,6-테트라메틸-4-피페리딜)-1,2,3,4-부탄 테트라오에이트, 1,1'-(1,2-에탄디일)-비스(3,3,5,5-테트라메틸피페라지논), 4-벤조일-2,2,6,6-테트라메틸피페리딘, 4-스테아릴옥시-2,2,6,6-테트라메틸피페리딘, 비스(1,2,2,6,6-펜타메틸피페리딜)-2-n-부틸-2-(2-하이드록시-3,5-디-3급 부틸벤질)-말로네이트, 3-n-옥틸-7,7,9,9-테트라메틸-1,3,8-트리아자스피로[4.5]데칸-2,4-디온, 비스(1-옥틸옥시-2,2,6,6-테트라메틸피페리딜)세바케이트, 비스(1-옥틸옥시-2,2,6,6-테트라메틸피페리딜)석시네이트, N,N'-비스(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌디아민과 4-모르폴리노-2,6-디클로로-1,3,5-트리아진과의 축합 생성물, 2-클로로-4,6-디(4-n-부틸아미노-2,2,6,6-테트라메틸피페리딜)-1,3,5-트리아진과 1,2-비스(3-아미노프로필아미노)에탄과의 축합 생성물, 2-클로로-4,6-디(4-n-부틸아미노-1,2,2,6,6-펜타메틸피페리딜)-1,3,5-트리아진과 1,2-비스(3-아미노프로필아미노)에탄과의 축합 생성물, 8-아세틸-3-도데실-7,7,9,9-테트라메틸-1,3,5-트리아자스피로[4.5]데칸-2,4-디온, 3-도데실-1-(2,2,6,6-테트라메틸-4-피페리딜)-피롤리딘-2,5-디온, 3-도데실-1-(1,2,2,6,6-펜타메틸-4-피페리딜)-피롤리딘-2,5-디온.5. sterically hindered amines such as bis (2,2,6,6-tetramethylpiperidyl) sebacate, bis- (2,2,6,6-tetramethylpiperidyl) succinate, bis (1,2,2,6,6-pentamethylpiperidyl) sebacate, n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonic acid bis (1,2,2,6 , 6-pentamethylpiperidyl) ester, condensation product of 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine with succinic acid, N, N'-bis (2 Condensation product of 2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine with 4-tert-octylamino-2,6-dichloro-1,3,5-s-triazine, tris (2 , 2,6,6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane Tetraoate, 1,1 '-(1,2-ethanediyl) -bis (3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpy Ferridine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis (1,2,2,6,6-penta Tilpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) -malonate, 3-n-octyl-7,7,9,9-tetramethyl -1,3,8-triazaspiro [4.5] decane-2,4-dione, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyl Oxy-2,2,6,6-tetramethylpiperidyl) succinate, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-mor Condensation products with polyno-2,6-dichloro-1,3,5-triazine, 2-chloro-4,6-di (4-n-butylamino-2,2,6,6-tetramethylpiperi Condensation products of dill) -1,3,5-triazine with 1,2-bis (3-aminopropylamino) ethane, 2-chloro-4,6-di (4-n-butylamino-1,2, Condensation product of 2,6,6-pentamethylpiperidyl) -1,3,5-triazine with 1,2-bis (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7, 7,9,9-tetramethyl-1,3,5-triazaspiro [4.5] decane-2,4-dione, 3-dodecyl-1- (2,2,6,6-tetramethyl-4- Piperidyl) -pyrrolidine-2,5- One, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) -pyrrolidine-2,5-dione.
6. 옥살산 디아미드, 예를 들면, 4,4'-디옥틸옥시-옥스아닐리드, 2,2'-디에톡시-옥스아닐리드, 2,2'-디옥틸옥시-5,5'-디-3급 부틸 옥스아닐리드, 2,2'-디도데실옥시-5,5'-디-3급 부틸 옥스아닐리드, 2-에톡시-2'-에틸 옥스아닐리드, N,N'-비스(3-디메틸아미노프로필)-옥살아미드, 2-에톡시-5-3급 부틸-2'-에틸 옥스아닐리드 및 2-에톡시-2'-에틸-5,4-디-3급 부틸 옥스아닐리드와 이들의 혼합물, o-메톡시-이치환된 옥스아닐리드와 p-메톡시-이치환된 옥스아닐리드와의 혼합물 및 o-에톡시-이치환된 옥스아닐리드와 p-에톡시-이치환된 옥스아닐리드와의 혼합물.6. Oxalic acid diamides such as 4,4'-dioctyloxy-oxanilide, 2,2'-diethoxy-oxanilide, 2,2'-dioctyloxy-5,5'-di-3 Tertiary butyl oxanilide, 2,2'-didodecyloxy-5,5'-di-tertiary butyl oxanilide, 2-ethoxy-2'-ethyl oxanilide, N, N'-bis (3-dimethyl Aminopropyl) -oxalamide, 2-ethoxy-5-tert-butyl-2'-ethyl oxanilide and 2-ethoxy-2'-ethyl-5,4-di-tert-butyl oxanilide and their Mixtures, mixtures of o-methoxy-disubstituted oxanilides with p-methoxy-disubstituted oxanilides and mixtures of o-ethoxy-disubstituted oxanilides and p-ethoxy-disubstituted oxanilides.
7. 2-(2-하이드록시페닐)-1,3,5-트리아진, 예를 들면, 2,4,6-트리스(2-하이드록시-4-옥틸옥시페닐)-1,3,5-트리아진, 2-(2-하이드록시-4-옥틸옥시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2,4-디하이드록시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2,4-비스(2-하이드록시-4-프로필옥시페닐)-6-(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2-하이드록시-4-옥틸옥시페닐)-4,6-비스(4-메틸페닐)-1,3,5-트리아진, 2-(2-하이드록시-4-도데실옥시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-[2-하이드록시-4-(2-하이드록시-3-부틸옥시-프로필옥시)페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-[2-하이드록시-4-(2-하이드록시-3-옥틸옥시-프로필옥시)페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진 및 2-[4-도데실옥시/트리데실옥시-(2-하이드록시프로필)옥시-2-하이드록시페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진.7. 2- (2-hydroxyphenyl) -1,3,5-triazine, for example 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5 -Triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-di Hydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2 , 4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine , 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxy-propyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyloxy-propyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine and 2- [4-dodecyloxy / tri Decyloxy- (2-hydroxypropyl) oxy-2-hydroxyphenyl] -4,6-bis (2,4-dime Phenyl) -1,3,5-triazine.
8. 포스파이트와 포스포나이트, 예를 들면, 트리페닐 포스포나이트, 디페닐알킬 포스파이트, 페닐디알킬 포스파이트, 트리스(노닐페닐)포스파이트, 트리라우릴 포스파이트, 트리옥타데실 포스파이트, 디스테아릴 펜타에리트리톨 디포스파이트, 트리스(2,4-디-3급 부틸페닐)포스파이트, 디이소데실펜타에리트리톨 디포스파이트, 비스(2,4-디-3급 부틸페닐)펜타에리트리톨 디포스파이트, 비스(2,6-디-3급 부틸-4-메틸페닐)펜타에리트리톨 디포스파이트, 비스이소데실옥시펜타에리트리톨 디포스파이트, 비스(2,4-디-3급 부틸-6-메틸페닐)펜타에리트리톨 디포스파이트, 비스(2,4,6-트리-3급 부틸-페닐)펜타에리트리톨 디포스파이트, 트리스테아릴 소르비톨 트리포스파이트, 테트라키스(2,4-디-3급 부틸페닐)-4,4'-비페닐렌 디포스포나이트, 6-이소옥틸옥시-2,4,8,10-테트라-3급 부틸-12H-디벤조[d,g]-1,3,2-디옥사포스포신, 6-플루오로-2,4,8,10-테트라-3급 부틸-12-메틸-디벤조[d,g]-1,3,2-디옥사포스포신, 비스(2,4-디-3급 부틸-6-메틸페닐)메틸 포스파이트 및 비스(2,4-디-3급 부틸-6-메틸페닐)에틸 포스파이트.8. Phosphites and phosphonites such as triphenyl phosphonite, diphenylalkyl phosphite, phenyldialkyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite , Distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaeryte Lithol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, bisisodecyloxypentaerythritol diphosphite, bis (2,4-di-tert-butyl-6-6- Methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tri-tert-butyl) phenyl pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butyl Phenyl) -4,4'-biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10-tet Tert-butyl-12H-dibenzo [d, g] -1,3,2-dioxaphosphosine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-di Benzo [d, g] -1,3,2-dioxaphosphosine, bis (2,4-di-tert-butyl-6-methylphenyl) methyl phosphite and bis (2,4-di-tert-butyl) 6-methylphenyl) ethyl phosphite.
또한, 당해 분야에서 통상적인 첨가제(예: 유동 조절제 및 접착 증진제)를 사용할 수 있다.It is also possible to use additives customary in the art, such as flow regulators and adhesion promoters.
광 중합을 촉진시키기 위하여, 또 다른 첨가제로서 아민[예: 트리에탄올아민, N-메틸-디에탄올아민, p-디메틸아미노벤조산 에틸 에스테르 또는 미흘러 케톤(Michler's ketone)]을 첨가할 수 있다. 벤조페논형 방향족 케톤을 첨가하여 아민의 작용을 강화시킬 수 있다. 산소 포획제로서 사용할 수 있는 아민은, 예를 들면, 유럽 특허 제339 841호에 기재되어 있는 바와 같은 치환된 N,N-디알킬아닐린이다. 또 다른 촉진제, 공개시제 및 자가산화제는, 예를 들면, 유럽 특허 제438 123호와 영국 특허 제2 180 358호에 기재되어 있는 바와 같은 티올, 티오에테르, 디설파이드 및 포스핀이다.To promote photopolymerization, as an additive, amines such as triethanolamine, N-methyl-diethanolamine, p-dimethylaminobenzoic acid ethyl ester or Michler's ketone can be added. Benzophenone type aromatic ketones can be added to enhance the action of amines. Amines that can be used as oxygen trapping agents are, for example, substituted N, N-dialkylanilines as described in EP 339 841. Still other promoters, publications and autooxidants are, for example, thiols, thioethers, disulfides and phosphines as described in European Patent No. 438 123 and British Patent No. 2 180 358.
또한, 본 발명에 따르는 조성물에 당해 분야에서 통상적인 연쇄이동제를 첨가할 수 있다. 예는 머캅탄, 아민 및 벤조티아졸을 포함한다.It is also possible to add chain transfer agents customary in the art to the compositions according to the invention. Examples include mercaptans, amines and benzothiazoles.
또한, 광 중합의 촉진은 또 다른 첨가제로서 스펙트럼 감도를 이동시키거나 넓히는 감광제를 첨가함으로써 달성할 수 있다. 이들은 특히 방향족 카보닐 화합물, 예를 들면, 벤조페논과 티오크산톤 유도체, 특히 이소프로필티오크산톤, 안트라퀴논 및 3-아실쿠마린 유도체, 터페닐, 스티릴케톤과 3-(아로일메틸렌)-티아졸린, 캄포퀴논을 포함하며 에오신, 로다민 및 에리트로신 염료도 포함한다. 예를 들면, 위에서 언급한 아민은 감광제로서 간주될 수도 있다.In addition, acceleration of photopolymerization can be achieved by adding a photosensitizer that shifts or broadens the spectral sensitivity as another additive. These are especially aromatic carbonyl compounds, for example benzophenone and thioxanthone derivatives, in particular isopropyl thioxanthone, anthraquinone and 3-acylcoumarin derivatives, terphenyl, styrylketone and 3- (aroylmethylene)- Thiazolin, camphorquinone and eosin, rhodamine and erythrosin dyes. For example, the amines mentioned above may be considered as photosensitizers.
예를 들면, 유럽 특허 제245 639호에 기재되어 있는 바와 같이, 특히 착색된 조성물(예를 들면, 이산화티탄을 사용하여 착색된 조성물)의 경우, 경화 과정은 추가의 첨가제로서 열 조건하에 유리 라디칼을 형성하는 성분, 예를 들면, 아조 화합물[예: 2,2'-아조비스(4-메톡시-2,4-디메틸발레로니트릴), 트리아젠, 디아조설파이드 또는 펜타아자디엔] 또는 퍼옥시 화합물[예: 하이드로퍼옥사이드 또는 퍼옥시카보네이트(예: 3급 부틸 하이드로퍼옥사이드)]을 첨가함으로써 보조할 수도 있다.For example, as described in EP 245 639, in particular in the case of colored compositions (e.g. compositions colored using titanium dioxide), the curing process is a free additive under thermal conditions as additional additives. To form a constituent, for example, an azo compound [eg, 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), triazene, diazosulfide or pentaazadiene] or fur It may also be assisted by adding oxy compounds such as hydroperoxides or peroxycarbonates such as tertiary butyl hydroperoxides.
또한, 본 발명에 따르는 조성물은 또 다른 첨가제로서 광 환원성 염료, 예를 들면, 크산텐, 벤조크산텐, 벤조티오크산텐, 티아진, 피로닌, 포르피린 또는 아크리딘 염료 및/또는 방사선 분할성 트리할로메틸 화합물을 포함할 수 있다. 유사한 물질은, 예를 들면, 유럽 특허 제445 624호에 기재되어 있다.In addition, the compositions according to the invention can be used as further additives for light reducing dyes, such as xanthene, benzoxanthene, benzothioxanthene, thiazine, pyronin, porphyrin or acridine dyes and / or radiation splitting. Trihalomethyl compounds. Similar materials are described, for example, in EP 445 624.
조성물의 목적하는 용도에 따라, 또 다른 통상적인 첨가제는 충전제, 착색제, 습윤제 및 유동 조절제이다.Depending on the intended use of the composition, another common additive is fillers, colorants, wetting agents and flow control agents.
예를 들면, 미국 특허 제5,013,768호에 기재되어 있는 바와 같이, 유리 마이크로비드 또는 미분된 유리 섬유를 첨가하면 착색된 두꺼운 피복 조성물을 경화시키는 데 적합하다.For example, the addition of glass microbeads or finely divided glass fibers, as described in US Pat. No. 5,013,768, is suitable for curing colored thick coating compositions.
첨가제의 종류는 당해 물질의 사용 분야와 이에 대해 요구되는 특성에 따라 결정된다. 위에서 설명한 첨가제는 당해 분야의 숙련가에게 잘 알려져 있으며, 당해 분야에서 통상적인 양으로 본 발명에 따르는 조성물에 사용한다.The type of additive is determined by the field of use of the material and the properties required for it. The additives described above are well known to those skilled in the art and are used in the compositions according to the invention in amounts customary in the art.
본 발명은 성분(a)로서 물에 용해되거나 유화된 하나 이상의 에틸렌성 불포화 광 중합 가능한 화합물을 포함하는 조성물에 관한 것이다.The present invention relates to a composition comprising as component (a) at least one ethylenically unsaturated photopolymerizable compound dissolved or emulsified in water.
이러한 수성 방사선 경화성 예비중합체 분산액은 수 많은 형태로 시판되고 있으며 물과 이에 분산된 하나 이상의 예비중합체로 이루어진 분산액으로서 간주된다. 이러한 시스템에서의 물의 농도는, 예를 들면, 5 내지 80중량%, 특히 30 내지 60중량%이다. 방사선 경화성 예비중합체 또는 이의 혼합물은, 예를 들면, 20 내지 95중량%, 특히 40 내지 70중량%의 농도로 존재한다. 이러한 조성물에 있어서, 물과 예비중합체에 대해 위에서 언급한 비율의 합은, 각각의 경우, 100이며, 첨가되는 보조제와 첨가제는 목적하는 용도에 따라 다양한 양으로 존재한다.Such aqueous radiation curable prepolymer dispersions are commercially available in many forms and are considered as a dispersion of water and one or more prepolymers dispersed therein. The concentration of water in such a system is, for example, 5 to 80% by weight, in particular 30 to 60% by weight. The radiation curable prepolymer or mixture thereof is, for example, present in a concentration of 20 to 95% by weight, in particular 40 to 70% by weight. In such compositions, the sum of the abovementioned ratios for water and prepolymer is in each case 100, and the adjuvant and additive added are present in varying amounts depending on the intended use.
물에 분산되거나 종종 용해되는 방사선 경화성 막 형성 예비중합체는 유리 라디칼에 의해 개시될 수 있는 일관능성 에틸렌성 불포화 예비중합체 또는 다관능성 에틸렌성 불포화 예비중합체이며, 예비중합체는 수성 예비중합체 분산액에 대해 그 자체로 공지되어 있으며, 예를 들면, 중합 가능한 이중결합을 예비중합체 100g당 0.01 내지 1.0mol 함유하며, 평균 분자량은, 예를 들면, 400 이상, 특히 500 내지 10,000이다. 그러나, 분자량이 높은 예비중합체는 목적하는 용도에 좌우되는 것으로도 간주될 수 있다.Radiation curable film-forming prepolymers that are dispersed or often dissolved in water are monofunctional ethylenically unsaturated prepolymers or polyfunctional ethylenically unsaturated prepolymers that can be initiated by free radicals, and the prepolymer itself is an aqueous prepolymer dispersion. For example, the polymerizable double bond contains 0.01 to 1.0 mol per 100 g of the prepolymer, and the average molecular weight is, for example, 400 or more, especially 500 to 10,000. However, high molecular weight prepolymers can also be considered to depend on the intended use.
유럽 특허 제12339호에 기재되어 있는 바와 같이, 예를 들면, 최대 산가가 10인 중합 가능한 C-C-이중결합 함유 폴리에스테르, 중합 가능한 C-C-이중결합 함유 폴리에테르, 1분자당 2개 이상의 에폭시 그룹을 함유하는 폴리에폭사이드와 하나 이상의 α,β-에틸렌성 불포화 카복실산과의 하이드록시 그룹 함유 반응 생성물, 폴리우레탄 (메트)아크릴레이트 및 α,β-에틸렌성 불포화 아크릴 라디칼을 함유하는 아크릴 공중합체를 사용할 수 있다. 이들 예비중합체의 혼합물도 사용할 수 있다. 또한, 유럽 특허 제 33896호에 기재되어 있는, 중합 가능한 예비중합체의 평균 분자량이 600 이상이고, 카복시 그룹 함량이 0.2 내지 15%이며, 중합 가능한 C-C 이중결합을 예비중합체 100g당 0.01 내지 0.8mol 함유하는 중합 가능한 예비중합체의 티오에테르 부가물이 적합하다. 유럽 특허 제41125호에는, 기타 적합한 특별한 (메트)아크릴산 알킬 에스테르 중합물계 수성 분산액이 기재되어 있으며, 독일 특허 제2,936,039호에는, 우레탄 아크릴레이트의 적합한 수 분산성, 방사선 경화성 예비중합체가 기재되어 있다.As described in EP 123939, for example, a polymerizable CC-double bond-containing polyester having a maximum acid value of 10, a polymerizable CC-double bond-containing polyether, at least two epoxy groups per molecule Acrylic copolymers containing a hydroxy group-containing reaction product of a polyepoxide containing and at least one α, β-ethylenically unsaturated carboxylic acid, a polyurethane (meth) acrylate and an α, β-ethylenically unsaturated acrylic radical Can be used. Mixtures of these prepolymers can also be used. In addition, the average molecular weight of the polymerizable prepolymer described in European Patent No. 33896 is 600 or more, the carboxy group content is 0.2 to 15%, and the polymerizable CC double bond contains 0.01 to 0.8 mol per 100 g of the prepolymer. Thioether adducts of polymerizable prepolymers are suitable. EP 41125 describes other suitable particular (meth) acrylic acid alkyl ester polymer-based aqueous dispersions, and DE 2,936,039 describes suitable water dispersible, radiation curable prepolymers of urethane acrylates.
이러한 방사선 경화성 수성 예비중합체 분산액은 또 다른 첨가제로서 분산제, 유화제, 산화방지제, 광 안정화제, 착색제, 충전제, 예를 들면, 활석, 석고, 실릭산, 루틸, 카본 블랙, 산화아연, 산화철, 반응 촉진제, 유동제, 활택제, 습윤제, 증점제, 염소제(dulling agent), 소포제 및 표면 피복 기술에서 통상적인 기타 보조제를 포함할 수 있다. 적합한 분산제는 극성 그룹을 갖는 수용성 고분자량 유기 화합물, 예를 들면, 폴리비닐 알콜, 폴리비닐피롤리돈 및 셀룰로즈 에테르를 포함한다. 이들은 유화제로서 비이온성 유화제를 사용할 수 있으나, 경우에 따라, 이온성 유화제도 사용할 수 있다.Such radiation curable aqueous prepolymer dispersions are further additives as dispersants, emulsifiers, antioxidants, light stabilizers, colorants, fillers such as talc, gypsum, silicic acid, rutile, carbon black, zinc oxide, iron oxides, reaction promoters. , Flow agents, glidants, wetting agents, thickeners, dulling agents, antifoams, and other auxiliaries customary in surface coating techniques. Suitable dispersants include water soluble high molecular weight organic compounds having polar groups such as polyvinyl alcohol, polyvinylpyrrolidone and cellulose ethers. These may use nonionic emulsifiers as emulsifiers, but in some cases, ionic emulsifiers may also be used.
특정한 경우, 화학식 1과 화학식 2의 2개 이상의 광 개시제의 혼합물을 사용하는 것이 유리할 수 있다. 물론, 또 다른 공지된 광 개시제와의 혼합물은, 예를 들면, 또 다른 벤조페논 유도체와의 혼합물, 아세토페논 유도체, 디알콕시아세토페논, α-하이드록시아세토페논, α-아미노아세토페논, 4-아로일-1,3-디옥솔란, 벤조인 알킬 에테르 및 벤질 케탈(예: 벤질 디메틸 케탈, 페닐 글리옥살레이트 및 이들의 유도체), 이량체성 페닐 글리옥살레이트, 페로세늄 화합물 또는 티타노센[예: 디사이클로펜타디에닐-비스(2,6-디플루오로-3-피롤로-페닐)-티탄], 벤조일 퍼옥사이드(적합한 퍼옥사이드는 미국 특허 제4,950,581호, column 19, lines 17-25에 기재되어 있다) 또는 사이클로펜타디에닐아렌-철(Ⅱ) 착염[예: (η6-이소-프로필벤젠)(η5-사이클로펜타디에닐)철(Ⅱ)헥사플루오로포스페이트]도 사용할 수 있다.In certain cases, it may be advantageous to use mixtures of two or more photoinitiators of Formula 1 and Formula 2. Of course, a mixture with another known photoinitiator is, for example, a mixture with another benzophenone derivative, acetophenone derivative, dialkoxyacetophenone, α-hydroxyacetophenone, α-aminoacetophenone, 4- Aroyl-1,3-dioxolane, benzoin alkyl ether and benzyl ketal (e.g. benzyl dimethyl ketal, phenyl glyoxalate and derivatives thereof), dimeric phenyl glyoxalate, ferrocenium compound or titanocene [e.g. Dicyclopentadienyl-bis (2,6-difluoro-3-pyrrolo-phenyl) -titanium], benzoyl peroxide (suitable peroxides are described in US Pat. No. 4,950,581, column 19, lines 17-25. Or cyclopentadienylarene-iron (II) complex salts such as (η 6 -iso-propylbenzene) (η 5 -cyclopentadienyl) iron (II) hexafluorophosphate].
예를 들면, 문헌[참조: 미국 특허 제4,950,581호, column 18, line 60 to column 19, line 10]에 기재되어 있는 바와 같이, 혼성 시스템에서 광 개시제를 사용하는 경우, 유리 라디칼 경화제 이외에 양이온성 광 개시제(예: 방향족 설포늄염, 방향족 포스포늄염 또는 방향족 요오도늄염)가 사용된다.For example, as described in US Pat. No. 4,950,581, column 18, line 60 to column 19, line 10, cationic light in addition to free radical curing agents when using photoinitiators in hybrid systems Initiators such as aromatic sulfonium salts, aromatic phosphonium salts or aromatic iodonium salts are used.
광 중합 가능한 조성물은, 조성물의 중량을 기준으로 하여, 광 개시제 또는 광 개시제 혼합물(b)을 유리하게는 0.05 내지 15중량%, 바람직하게는 0.1 내지 5중량%의 양으로 함유한다. 기재한 광 개시제의 양은 이들의 혼합물을 사용할 때 첨가한 모든 광 개시제의 합이다.The photopolymerizable composition, based on the weight of the composition, advantageously contains the photoinitiator or photoinitiator mixture (b) in an amount of 0.05 to 15% by weight, preferably 0.1 to 5% by weight. The amount of photoinitiator described is the sum of all photoinitiators added when using these mixtures.
광 중합 가능한 조성물은, 벌크 경화법(투명 성형에 있어서의 UV 경화)에 의해 3차원 제품을 제조하거나, 예를 들면, 미국 특허 제4,575,330호에 기재되어 있는 바와 같은 석판 인쇄 공정에 따라 복합 물질(예를 들면, 스티렌 폴리에스테르는, 경우에 따라, 유리 섬유 및/또는 기타 섬유와 기타 보조제를 포함할 수 있다)과 전자 성분의 도막 또는 밀봉물에서의 기타 적층 증점 조성물을 제조하는 경우, 예를 들면, 인쇄 잉크, 투명 락카(clear lacquers), 백색 표면 피복 조성물(예: 목재 또는 금속용)로서, 분말 피복 조성물로서, 그 중에서도 특히 종이, 목재, 금속 또는 플라스틱용 피복 물질로서, 건물과 도로 표시용 일광 경화성 페인트로서, 치아 충전 화합물로서, 접착제로서, 감압성 접착제로서, 적층용 수지로서 또는 광섬유용 피복물로서의 다양한 목적을 위해 사용할 수 있다.The photopolymerizable composition may be prepared by producing a three-dimensional product by a bulk curing method (UV curing in transparent molding) or by using a composite material according to a lithography process as described in, for example, US Patent No. 4,575,330. For example, styrene polyester may optionally include glass fibers and / or other fibers and other auxiliaries) and other laminated thickening compositions in coatings or seals of electronic components, e.g. For example, printing inks, clear lacquers, white surface coating compositions (e.g. for wood or metal), as powder coating compositions, in particular as coating materials for paper, wood, metal or plastics, for building and road markings. For sun-curable paints, as tooth filling compounds, as adhesives, as pressure sensitive adhesives, as laminating resins or as coatings for optical fibers It can be used.
또한, 본 발명에 따르는 조성물은, 독일 특허 제19,700,064호와 유럽 특허 제678 534호에 기재되어 있는 바와 같이, 열호변 특성(thermotropic property)을 갖는 겔을 제조하는 데 사용할 수 있다. 광 개시제는 유화 중합, 비드 중합 또는 현탁 중합용 개시제로서, 액정성 단량체와 올리고머의 배향 상태를 고정시키기 위한 중합 단계의 개시제로서 또는 유기 물질에 염료를 고정시키기 위한 개시제로서 사용할 수 있다.The compositions according to the invention can also be used to prepare gels with thermotropic properties, as described in German Patent No. 19,700,064 and European Patent 678 534. The photoinitiator can be used as an initiator for emulsion polymerization, bead polymerization or suspension polymerization, as an initiator for the polymerization step for fixing the alignment state of the liquid crystalline monomer and the oligomer or as an initiator for fixing the dye to the organic material.
바람직하게는, 본 발명에 따르는 조성물은 표면 피복물을 제조하는 데 사용한다.Preferably, the composition according to the invention is used to prepare a surface coating.
따라서, 본 발명은 위에서 언급한 바와 같은 조성물, 특히 백색 착색된 조성물을 포함하는 착색된 표면 피복물에 관한 것이며, 피복물 또는 표면 피복물, 특히 백색 표면 피복물로서의 위에서 언급한 바와 같은 조성물의 용도에 관한 것이다.The present invention therefore relates to colored surface coatings comprising the compositions as mentioned above, in particular white colored compositions, and to the use of the compositions as mentioned above as coatings or surface coatings, in particular white surface coatings.
예비중합체와 일불포화 단량체를 추가로 포함하는 다불포화 단량체와의 혼합물은 종종 표면 피복물에서 사용된다. 예비중합체의 종류에 따라, 특히 표면 피복물의 특성이 결정되므로, 당해 분야의 숙련가는 예비중합체를 변화시킴으로써 경화 막의 특성에 영향을 미칠 수 있다. 다불포화 단량체는 불용성 표면 피복막을 제공하는 가교 결합제로서 작용한다. 일불포화 단량체는 용매의 부재하에 점도를 감소시킴으로써, 반응성 희석액으로서 작용한다.Mixtures of prepolymers with polyunsaturated monomers further comprising monounsaturated monomers are often used in surface coatings. Depending on the type of prepolymer, in particular the properties of the surface coating are determined, so a person skilled in the art can influence the properties of the cured film by changing the prepolymer. The polyunsaturated monomer acts as a crosslinker to provide an insoluble surface coating. Monounsaturated monomers act as reactive diluents by decreasing viscosity in the absence of solvent.
불포화 폴리에스테르 수지는 통상적으로 일불포화 단량체, 바람직하게는 스티렌과 함께 2성분계에서 사용한다.Unsaturated polyester resins are usually used in bicomponent systems with monounsaturated monomers, preferably styrene.
또한, 본 발명에 따르는 조성물은 방사선 경화성 분말 피복 조성물에 대해 사용할 수 있다. 분말 피복 조성물은 고체 수지계일 수 있으며, 반응성 이중결합을 함유하는 단량체(예: 말레에이트, 비닐 에테르, 아크릴레이트, 아크릴아미드 및 이들의 혼합물)일 수 있다. 유리 라디칼성 UV 경화성 분말 피복 조성물은, 예를 들면, 문헌[참조: "Radiation Curing of Power Coating", Conference Proceedings, Radtech Europe 1993, M. Wittig and Th. Gohmann]에 기재되어 있는 바와 같이, 불포화 폴리에스테르 수지(예: 메틸아크릴아미도글리콜레이트 메틸 에스테르)를 고체 아크릴아미드 및 유리 라디칼 광 개시제와 혼합함으로써 제형화할 수 있다. 마찬가지로, 유리 라디칼성 UV 경화성 분말 피복 조성물은 불포화 폴리에스테르 수지를 고체 아크릴레이트, 메타크릴레이트 또는 비닐 에테르 및 광 개시제(또는 광 개시제 혼합물)와 혼합함으로써 제형화할 수 있다. 예를 들면, 독일 특허 제4,228,514호와 유럽 특허 제636 669호에 기재되어 있는 바와 같이, 분말 피복 조성물은 결합제도 포함할 수 있다. UV 경화성 분말 피복 조성물은 백색 안료 또는 착색된 안료도 포함할 수 있다. 예를 들면, 특히 루틸/이산화티탄을 50중량% 이하의 농도로 사용하여 피복력이 우수한 경화 분말 피복 조성물을 수득할 수 있다. 이 공정은 통상적으로 분말을 기판(예: 금속 또는 목재) 위에 정전적으로 또는 마찰역학적으로 분사하고, 가열하여 분말을 용융시키고, 매끈한 막을 형성시킨 다음, 예를 들면, 중압 수은 램프 , 금속 할라이드 램프 또는 크세논 램프를 사용하여 방사선 경화성 도막에 자외선 및/또는 가시광선을 조사함을 포함한다. 상응하는 열 경화성 도막에 대하여 방사선 경화성 분말 피복 조성물의 특별한 이점은, 분말 입자를 용융시킨 후에 유동 시간을 목적하는 바와 같이 연장시킴으로써, 매끈한 고광택성 피복 조성물의 형성을 보증할 수 있다는 점이다. 열 경화성 시스템과는 달리, 방사선 경화성 분말 피복 조성물을 제형화함으로써, 유효 수명이 단축되는 부작용이 없이, 비교적 저온에서 이들을 용융시킬 수 있다. 이로 인해, 예를 들면, 목재 또는 플라스틱과 같은 감열성 기판용 피복물로서도 적합하다.In addition, the compositions according to the invention can be used for radiation curable powder coating compositions. The powder coating composition may be solid resin based and may be a monomer containing a reactive double bond (eg maleate, vinyl ether, acrylate, acrylamide and mixtures thereof). Free radical UV curable powder coating compositions are described, for example, in "Radiation Curing of Power Coating", Conference Proceedings, Radtech Europe 1993, M. Wittig and Th. As described in Gohmann, unsaturated polyester resins such as methylacrylamidoglycolate methyl esters can be formulated by mixing with solid acrylamide and free radical photoinitiators. Likewise, free radical UV curable powder coating compositions can be formulated by mixing unsaturated polyester resins with solid acrylates, methacrylates or vinyl ethers and photoinitiators (or photoinitiator mixtures). For example, as described in German Patent No. 4,228,514 and European Patent No. 636 669, the powder coating composition may also include a binder. The UV curable powder coating composition may also comprise white pigments or colored pigments. For example, in particular, the use of rutile / titanium dioxide in a concentration of 50% by weight or less can give a cured powder coating composition having excellent coating power. This process typically involves spraying the powder electrostatically or tribologically onto a substrate (e.g. metal or wood), heating to melt the powder, forming a smooth film, and for example, a medium pressure mercury lamp, a metal halide lamp or Irradiating ultraviolet and / or visible light to the radiation curable coating film using a xenon lamp. A particular advantage of the radiation curable powder coating composition for the corresponding heat curable coating film is that it can ensure the formation of a smooth high gloss coating composition by melting the powder particles and extending the flow time as desired. Unlike thermally curable systems, by formulating a radiation curable powder coating composition, they can be melted at relatively low temperatures without the side effects of shortening their useful life. For this reason, it is suitable also as a coating for thermosensitive board | substrates, such as wood or plastics.
광 개시제 이외에도, 분말 피복 조성물은 UV 흡수제도 포함할 수 있다. 적절한 예는 위에서 항목 1 내지 항목 8에 기재하였다.In addition to the photoinitiator, the powder coating composition may also include a UV absorber. Suitable examples are described above in items 1-8.
본 발명에 따르는 광 경화성 조성물은, 예를 들면, 보호막을 적용하는 모든 종류의 기판, 예를 들면, 목재, 섬유, 종이, 세라믹, 유리, 플라스틱(예: 폴리에스테르, 폴리에틸렌, 테레프탈레이트, 폴리올레핀 또는 특히 막 형태의 셀룰로즈 아세테이트) 및 금속(예: Al, Cu, Ni, Fe, Zn, Mg 또는 Co)과 GaAs, Si 또는 SiO2용 피복 조성물로서 적합하다.The photocurable compositions according to the invention can be used, for example, for all kinds of substrates to which protective films are applied, for example wood, fibers, paper, ceramics, glass, plastics (e.g. polyester, polyethylene, terephthalate, polyolefins or Particularly suitable are coating compositions for film cellulose acetate) and metals (eg Al, Cu, Ni, Fe, Zn, Mg or Co) and GaAs, Si or SiO 2 .
액체 조성물, 용액 또는 현탁액을 기판에 적용시킴으로써, 기판을 피복시킬 수 있다. 용매의 종류와 이의 농도는 주로 조성물의 특성과 피복 방법에 의해 결정된다. 용매는 불활성이어야 한다. 즉, 임의의 화학 반응에 성분을 혼입하지 않아야 하며, 피복 작업에 이어서 건조 작업 도중에 이를 다시 제거할 수 있어야 한다. 적합한 용매는, 예를 들면, 케톤, 에테르 및 에스테르(예: 메틸 에틸 케톤, 이소부틸 메틸 케톤, 사이클로펜타논, 사이클로헥사논, N-메틸피롤리돈, 디옥산, 테트라하이드로푸란, 2-메톡시에탄올, 2-에톡시에탄올, 1-메톡시-2-프로판올, 1,2-디메톡시에탄, 에틸 아세테이트, n-부틸 아세테이트 및 에틸 3-에톡시프로피오네이트)를 포함한다.The substrate can be coated by applying a liquid composition, solution or suspension to the substrate. The type of solvent and its concentration are mainly determined by the properties of the composition and the coating method. The solvent should be inert. In other words, the components should not be incorporated into any chemical reaction, and should be able to be removed again during the coating operation followed by the drying operation. Suitable solvents are, for example, ketones, ethers and esters such as methyl ethyl ketone, isobutyl methyl ketone, cyclopentanone, cyclohexanone, N-methylpyrrolidone, dioxane, tetrahydrofuran, 2-meth Methoxyethanol, 2-ethoxyethanol, 1-methoxy-2-propanol, 1,2-dimethoxyethane, ethyl acetate, n-butyl acetate and ethyl 3-ethoxypropionate).
조성물은 공지된 피복 방법, 예를 들면, 스핀 피복법(spin-coating), 침지법(immersion), 나이프 피복법(knife coating), 커튼 주입법(curtain pouring), 브러쉬 도포법(brush application) 또는 분무법(spraying), 특히 정전 분무법과 리버어스-롤 피복법(reverse-roll coating) 또는 전기영동 도장법(electrophoretic deposition)으로 기판에 균일하게 적용시킨다. 또한, 감광막을 임시 가요성 기판에 적용시키고, 이어서 적층법에 의해 막을 이동시킴으로써 최종 기판을 피복시킬 수 있다.The composition may be a known coating method such as spin-coating, immersion, knife coating, curtain pouring, brush application or spraying. It is evenly applied to the substrate by spraying, in particular electrostatic spraying and reverse-roll coating or electrophoretic deposition. In addition, the photosensitive film can be applied to a temporary flexible substrate, and then the final substrate can be coated by moving the film by a lamination method.
적용하는 양(막 두께)과 기판의 특성(막 기판)은 바람직한 사용 분야에 따라 좌우된다. 막의 두께 범위는 통상적으로 약 0.1 내지 100μm 이상, 예를 들면, 20mm 또는 0.02 내지 10cm, 바람직하게는 0.02 내지 2cm이다.The amount to be applied (film thickness) and the characteristics of the substrate (film substrate) depend on the desired field of use. The thickness range of the film is usually about 0.1 to 100 μm or more, for example 20 mm or 0.02 to 10 cm, preferably 0.02 to 2 cm.
광 경화는 인쇄 잉크(또한, 본 발명에 따르는 조성물은 이러한 잉크를 제조하는 데 사용할 수 있다)용으로 매우 중요한데, 이는 결합제의 건조 시간이 그래픽 생성물의 제조 비율에 있어서의 측정인자이며 대개 1초의 몇 분의 몇 정도이어야 하기 때문이다. UV 경화성 잉크는 특히 스크린 인쇄에 대해 중요하다.Photocuring is very important for printing inks (also the compositions according to the invention can be used to prepare such inks), where the drying time of the binder is a measure of the rate of production of the graphic product and is usually a few seconds Because it should be a few minutes. UV curable inks are particularly important for screen printing.
광 경화에 대한 용도의 다른 분야는, 예를 들면, PVC계 바닥 또는 벽면 피복물의 플라스틱 피복물에 대한 광 경화 뿐만 아니라, 예를 들면, 쉬트와 튜브에 대한 마감제, 캔 밀봉 또는 병 밀봉의 적용에 있어서 또는 자동차에 대한 마감제의 적용에 있어서의 금속 피복물이다.Another field of use for light curing is, for example, in the application of finishes, can seals or bottle seals to sheets and tubes, as well as light curing to plastic coatings of PVC-based floor or wall coatings, for example. Or metal coatings in the application of finishes to automobiles.
종이 피복물의 광 경화의 예는 라벨, 레코드 슬리브 또는 서적 표지에 대한 마감제의 적용을 포함한다.Examples of light curing of paper coatings include the application of finishes to labels, record sleeves or book labels.
본 발명에 따르는 조성물의 용도는 복합 물질로부터 성형물을 제조하는 데 있어서도 유용하다. 복합 물질은 자가 지지 매트릭스 물질, 예를 들면, 제직용 유리 섬유, 또는 달리, 예를 들면, 식물 섬유[참조: K.-P. Mieck, T. Reussmann, Kunststoffe 85 (1995), 366-370 또는 V. Narayanan, A. B. Scranton, Trends, Polymer Science 1997 (5), 12, 415]로 이루어져 있으며, 이는 광 경화성 조성물로 함침된다. 본 발명에 따르는 조성물을 사용하여 제조되는 복합 물질의 성형품은 고도의 역학적 안정성과 저항을 갖는다. 또한, 본 발명에 따르는 조성물은, 예를 들면, 유럽 특허 제7086호에 기재되어 있는 바와 같이, 성형, 함침 및 피복 물질에 사용할 수 있다. 이러한 물질은, 예를 들면, 경화 활성도와 황색화에 대한 저항에 있어서의 요구가 증가되고 있는 박막 수지와 섬유 강화 성형 물질(예: 평면 광 패널이나 종방향 또는 횡방향 파형 광 패널)이다. 성형 물질의 제조공정[예: 수동 레이-업 공정(manual lay-up processes), 섬유 분무 공정, 스핀 공정 또는 권취 공정]은, 예를 들면, 문헌[참조: P. H. Selden, "Glasfaserverstarkte Kunststoffe", page 610, Springer Verlag Berlin-Heidelberg-New York 1967]에 기재되어 있다. 이 공정에 따라 제조할 수 있는 제품은, 예를 들면, 양면이 유리 섬유 강화 플라스틱으로 도포된 보트, 마분지 또는 합판, 파이프, 스포츠 용구, 지붕 피복물, 콘테이너 등이다. 성형 물질, 함침 물질 및 피복 물질의 또 다른 예는 유리 섬유 함유 성형 물질(GRP)용 UP 수지 박막(예: 파형 패널과 종이 적층물)이다. 종이 적층물은 우레아 수지계 또는 멜라민 수지계이다. 적층물을 제조하기 전에, 박막을 기판(예를 들면, 박막) 위에 제조한다. 또한, 본 발명에 따르는 광 경화성 조성물은 캐스팅 수지 또는 제품의 폿팅(potting), 예를 들면, 전자 성분 등에 대해 사용할 수 있다. 또한, 이들은 캐비티와 파이프를 라이닝하는 데 사용할 수 있다. 경화 과정에 있어서, 통상적으로 UV 경화에서 중압 수은 램프를 사용하지만, 보다 덜 강력한 램프(예: TL 40W/03형 또는 TL 40W/05형)도 특히 유용하다. 이들 램프의 강도는 일광의 강도와 대략 상응하다. 직사광선도 경화시키는 데 사용할 수 있다. 또 다른 이점은, 광원으로부터 부분 경화성 플라스틱 상태에서 복합 물질을 제거하고, 빛에 다시 노출시켜 완전 경화를 달성한 후에 셩형시킬 수 있다는 점이다.The use of the composition according to the invention is also useful for producing moldings from composite materials. The composite material may be a self-supporting matrix material, for example woven glass fibers, or alternatively, for example, plant fibers [K.-P. Mieck, T. Reussmann, Kunststoffe 85 (1995), 366-370 or V. Narayanan, A. B. Scranton, Trends, Polymer Science 1997 (5), 12, 415], impregnated with a photocurable composition. Molded articles of composite materials produced using the compositions according to the invention have a high degree of mechanical stability and resistance. The compositions according to the invention can also be used for molding, impregnation and coating materials, as described, for example, in EP 7086. Such materials are, for example, thin film resins and fiber-reinforced molding materials (e.g., planar light panels or longitudinal or transverse corrugated light panels) which have increased demands on curing activity and resistance to yellowing. Processes for the production of molding materials (eg manual lay-up processes, fiber spray processes, spin processes or winding processes) are described, for example, in PH Selden, "Glasfaserverstarkte Kunststoffe", page 610, Springer Verlag Berlin-Heidelberg-New York 1967. The products which can be produced according to this process are, for example, boats, cardboard or plywood, pipes, sports equipment, roof coatings, containers, etc., coated on both sides with glass fiber reinforced plastic. Another example of molding material, impregnation material and coating material is a UP resin thin film (eg corrugated panel and paper laminate) for glass fiber containing molding material (GRP). Paper laminates are urea resins or melamine resins. Prior to making the laminate, a thin film is prepared on a substrate (eg, a thin film). In addition, the photocurable compositions according to the invention can be used for potting of casting resins or articles, for example electronic components and the like. They can also be used for lining cavities and pipes. In the curing process, a medium pressure mercury lamp is usually used in UV curing, but less powerful lamps (e.g., type TL 40W / 03 or type TL 40W / 05) are also particularly useful. The intensity of these lamps approximately corresponds to the intensity of sunlight. Direct sunlight can also be used to cure. Another advantage is that the composite material can be removed from the light source in a partially curable plastic state and then re-exposed to light to achieve full curing after achieving full curing.
본 발명에 따르는 조성물의 감광도는 통상적으로 약 200 내지 약 600nm(UV장)의 범위이다. 적합한 방사선은, 예를 들면, 일광 또는 인조 광원의 광에 존재한다. 따라서, 다수의 가장 다양한 종류의 광원을 사용할 수 있다. 양자의 공급원과 편평한 라디에이터(램프 카펫)가 적합하다. 예는 다음과 같다: 카본 아아크 램프, 크세논 아아크 램프, 중압 수은 아아크 라디에이터, 고압 수은 아아크 라디에이터, 저압 수은 아아크 라디에이터, 경우에 따라, 금속 할라이드를 사용한 도핑(금속 할라이드 램프), 마이크로파 여기성 금속 증기 램프, 엑시머 램프(excimer lamps), 초활성 형광 튜브, 형광 램프, 아르곤 백열 램프, 섬광 램프, 사진 투광 조명 램프, 광 방사 다이오드(LED), 전자빔 및 X선. 노출시에 본 발명에 따르는 램프와 기판과의 거리는 목적하는 용도와 램프의 형태 및 강도에 따라 다양할 수 있으며, 예를 들면, 2 내지 150cm일 수 있다. 248nm에서의 노출에 있어서, 레이저 광원, 예를 들면, 엑시머 레이저(예: Krypton-F 레이저)가 특히 적합하다. 또한, 레이저는 가시 영역에서도 사용할 수 있다. 예를 들면, 석판 인쇄 오프셋 인쇄판 또는 릴리프 인쇄판은 이 방법에 따라 제조할 수 있다.The photosensitivity of the compositions according to the invention is typically in the range of about 200 to about 600 nm (UV field). Suitable radiation is, for example, present in the light of daylight or artificial light sources. Thus, many of the most diverse kinds of light sources can be used. Both sources and flat radiators (lamp carpets) are suitable. Examples include: carbon arc lamps, xenon arc lamps, medium pressure mercury arc radiators, high pressure mercury arc radiators, low pressure mercury arc radiators, optionally doping with metal halides (metal halide lamps), microwave excited metal vapor lamps , Excimer lamps, superactive fluorescent tubes, fluorescent lamps, argon incandescent lamps, flash lamps, photo floodlight lamps, light emitting diodes (LEDs), electron beams and X-rays. The distance between the lamp and the substrate according to the invention upon exposure may vary depending on the intended use and the shape and intensity of the lamp, for example 2 to 150 cm. For exposure at 248 nm, laser light sources such as excimer lasers (eg Krypton-F lasers) are particularly suitable. The laser can also be used in the visible region. For example, lithographic offset printing plates or relief printing plates can be produced according to this method.
본 발명에 따르는 광 경화성 조성물은 놀랍게도 완전 경화 특성이 우수하다.The photocurable compositions according to the invention surprisingly are excellent in full cure properties.
또한, 본 발명은 위에서 언급한 바와 같은 조성물에 200 내지 600nm 범위의 광을 조사함을 포함하여, 하나 이상의 에틸렌성 불포화 이중결합을 갖는 비휘발성 단량체성, 올리고머성 또는 중합체성 화합물을 광중합시키는 방법에 관한 것이다.The present invention also provides a method for photopolymerizing a nonvolatile monomeric, oligomeric or polymeric compound having at least one ethylenically unsaturated double bond, comprising irradiating a composition as mentioned above with light in the range of 200 to 600 nm. It is about.
또한, 본 발명은 입체 석판 인쇄에 의해 3차원 제품을 제조하는 데 있어서, 착색 및 비착색 표면 피복물, 인쇄 잉크, 분말 피복물, 인쇄판, 접착제, 치과 재료, 복합 물질, 유리 섬유 케이블 피복물 및 스크린 인쇄 스텐실의 제조에 있어서의 위에서 언급한 조성물의 용도에 관한 것이며, 입체 석판 인쇄에 의해 3차원 제품을 제조하는 데 있어서, 착색 및 비착색 표면 피복 조성물, 인쇄 잉크, 분말 피복 조성물, 인쇄판, 접착제, 치과 재료, 복합 물질, 유리 섬유 케이블 피복 조성물 및 스크린 인쇄 스텐실의 제조공정에 관한 것이다.In addition, the present invention relates to the production of three-dimensional products by stereolithography, wherein colored and uncolored surface coatings, printing inks, powder coatings, printing plates, adhesives, dental materials, composite materials, glass fiber cable coatings and screen printing stencils To the use of the above-mentioned compositions in the preparation of a product, in the manufacture of three-dimensional articles by stereolithography, colored and non-pigmented surface coating compositions, printing inks, powder coating compositions, printing plates, adhesives, dental materials , Composite materials, fiberglass cable coating compositions, and screen printing stencils.
또한, 본 발명은 피복물 또는 표면 피복물, 특히 백색 표면 피복물로서의, 그리고 스크린 인쇄 잉크, 특히 백색 스크린 인쇄 잉크로서의 청구범위 제1항에 따르는 조성물의 용도에 관한 것이다.The invention also relates to the use of the composition according to claim 1 as a coating or surface coating, in particular a white surface coating, and as a screen printing ink, in particular a white screen printing ink.
또한, 본 발명은 피복물 또는 표면 피복물, 특히 백색 표면 피복물로서의, 그리고 스크린 인쇄 잉크, 특히 백색 스크린 인쇄 잉크로서의 청구범위 제1항에 따르는 조성물의 용도에 관한 것이다.The invention also relates to the use of the composition according to claim 1 as a coating or surface coating, in particular a white surface coating, and as a screen printing ink, in particular a white screen printing ink.
마찬가지로, 본 발명은 위에서 언급한 바와 같은 조성물이 하나 이상의 표면에 피복되어 있는 피복 기판에 관한 것이며, 이러한 경화 조성물에 관한 것이다.Likewise, the present invention relates to coated substrates wherein the composition as mentioned above is coated on at least one surface, and relates to such cured compositions.
다음 실시예는 본 발명을 추가로 예시한다. 달리 언급되지 않는 한, 명세서의 다음 부분과 청구범위에서의 부와 비율은 중량을 기준으로 한다. 탄소수 3 이상의 알킬 라디칼 또는 알콕시 라디칼이 이들의 이성체 형태를 참고않고 언급되어 있는 경우, 각각은 n-이성체이다.The following examples further illustrate the invention. Unless stated otherwise, parts and ratios in the following parts of the specification and claims are based on weight. Where alkyl or alkoxy radicals having 3 or more carbon atoms are mentioned without reference to their isomeric forms, each is an n-isomer.
실시예에서 다음의 광 개시제를 사용한다.In the examples, the following photoinitiators are used.
P1은 2,4,6-트리메틸벤조일-디페닐-포스핀 옥사이드와 2-하이드록시-2-메틸-1-페닐-프로판과의 1:1 혼합물.P1 is a 1: 1 mixture of 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propane.
P2는 2,4,6-트리메틸벤조일-디페닐-포스핀 옥사이드.P2 is 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.
P3은 (2,4,6-트리메틸벤조일)-디페닐-포스핀 옥사이드와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물.P3 is a 1: 1 mixture of (2,4,6-trimethylbenzoyl) -diphenyl-phosphine oxide with (1-hydroxy-cyclohexyl) -phenyl-ketone.
P4는 (2,4,6-트리메틸벤조일)-에톡시-페닐-포스핀 옥사이드와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물.P4 is a 1: 1 mixture of (2,4,6-trimethylbenzoyl) -ethoxy-phenyl-phosphine oxide with (1-hydroxy-cyclohexyl) -phenyl-ketone.
P5는와 (1-하이드록시-사이클로헥실)-페닐-케톤과의 1:1 혼합물.P5 is 1: 1 mixture with (1-hydroxy-cyclohexyl) -phenyl-ketone.
실시예에서 다음의 형광증백제를 사용한다.In the examples, the following optical brighteners are used.
RUVITEX OB시바 스페치알리테텐케미사 제조 R UVITEX OB SHIBA SPECALIITETENKEMY Corporation
A1(여기서, R15는 CH3이다)A1 Where R 15 is CH 3
A2(여기서, R15는 CH2CH(CH3)CH2CH3이다)A2 Wherein R 15 is CH 2 CH (CH 3 ) CH 2 CH 3
실시예 1: 에폭시 아크릴레이트 백색 표면 피복물의 경화Example 1 Curing of Epoxy Acrylate White Surface Coatings
조성이 다음과 같은 백색 표면 피복물을 제조한다:A white surface coating having the following composition is prepared:
65% 에폭시 아크릴레이트(REBECRYL 604, UCB, 벨기에)65% epoxy acrylate ( R EBECRYL 604, UCB, Belgium)
10% 헥산디올 디아크릴레이트10% hexanediol diacrylate
25% 이산화티탄(루틸형,RRTC-2, 티옥사이드, 프랑스)25% titanium dioxide (rutile type, R RTC-2, titanium oxide, France)
3% 광 개시제와 0.5% 형광증백제(RUVITEX OB, 스위스, 시바 스페치알리테텐케미사 제조)를 위에서 언급한 조성물에 혼입시킨다. 150μm 슬롯형 나이프를 사용하여, 층을 밝은 색으로 하도처리된 칩보드(chipboard)에 도포시킨다. 2개의 80W/cm 중압 수은 램프(UV-프로세서, 미국, 에어테크 제조)를 사용하여 10m/min 내지 20m/min의 벨트 속도로 노출시킨다. 노출시킨 후, 쾨니히(DIN 53157)에 따라 스크래치 저항성 완전 경화 층의 경도(PH)를 측정하고 황색도를 확인한다(ASTM D1925-88). 조사한 후에 기판으로부터 분리시킨 층의 밑면이 건조한 경우, 층이 완전 경화된 것으로 간주한다. 진자 경도 값이 높을수록 방사성 피복물의 경화가 우수하다. 황색도(YI) 값이 낮을수록 경화 층은 덜 황화(黃化)된다. 결과는 다음 표 1에 기재되어 있다.3% photoinitiator and 0.5% fluorescence brightener ( R UVITEX OB, manufactured by Ciba Specilite Tetenchemis, Switzerland) are incorporated into the above-mentioned composition. Using a 150 μm slotted knife, the layers are applied to a brightly colored chipboard. Two 80 W / cm medium pressure mercury lamps (UV-processor, manufactured by Airtech, USA) are used to expose at belt speeds of 10 m / min to 20 m / min. After exposure, the hardness (PH) of the scratch resistant fully cured layer is measured according to the König (DIN 53157) and the yellowness is checked (ASTM D1925-88). If the underside of the layer separated from the substrate after irradiation is dry, the layer is considered to be fully cured. The higher the pendulum hardness value, the better the curing of the radioactive coating. The lower the yellowness (YI) value, the less yellow the hardened layer. The results are shown in Table 1 below.
RUVITEX OB, 시바 스페치알리테텐케미사 제조 R UVITEX OB, manufactured by Ciba Sp.
실시예 2: 폴리에스테르 아크릴레이트 백색 표면 피복물의 경화Example 2: Curing of Polyester Acrylate White Surface Coatings
조성이 다음과 같은 백색 표면 피복물을 제조한다:A white surface coating having the following composition is prepared:
67.5% 폴리에스테르 아크릴레이트(REBECRYL 830, UCB, 벨기에)67.5% polyester acrylate ( R EBECRYL 830, UCB, Belgium)
5.0% 헥산디올 디아크릴레이트5.0% hexanediol diacrylate
2.5% 트리메틸롤프로판 트리아크릴레이트2.5% trimethylolpropane triacrylate
25.0% 이산화티탄(루틸형,RRTC-2, 티옥사이드, 프랑스)25.0% titanium dioxide (rutile type, R RTC-2, titanium oxide, France)
실시예 1에서 기재한 바와 같이, 도포, 경화 및 측정을 수행한다. 사용한 광 개시제와 형광증백제 및 측정 결과는 표 2에 기재되어 있다.As described in Example 1, application, curing and measurement are performed. The photoinitiator used, the optical brightener and the measurement results are shown in Table 2.
실시예 3: 폴리에스테르 아크릴레이트 백색 표면 피복물의 경화Example 3: Curing of Polyester Acrylate White Surface Coatings
조성이 실시예 2에서 언급한 바와 같은 백색 표면 피복물을 제조한다. 실시예 1에서 언급한 바와 같이 도포와 경화를 수행한다. 각각의 경우, 경화 후에 5m/min의 벨트 속도로 황색도와 진자 경도를 측정한다. 그러나, 황색도와 진자 경도 이외에, 최대 경화성 유리 층 깊이(FL)를 확인한다. 이를 위해, 기판에 경화되는 조성물을 적량 적용시키고, 3m/min의 벨트 속도로 조사한다. 이어서, 경화 층을 기판으로부터 분리시키고, 경화 층의 두께(μm)를 확인한다. 층이 두꺼울수록 시험 조성물의 완전 경화가 우수하다. 또한, 부점착성 경화 층을 제조하는 데 필요한 10m/min에서의 수행 횟수를 확인한다[수행 횟수(n) x 10m/min라고 함]. 사용한 광 개시제와 형광증백제 및 측정 결과는 표 3에 기재되어 있다.Prepare a white surface coating whose composition is as mentioned in Example 2. Application and curing are carried out as mentioned in Example 1. In each case, yellowness and pendulum hardness are measured at a belt speed of 5 m / min after curing. However, in addition to yellowness and pendulum hardness, the maximum curable glass layer depth (FL) is ascertained. To this end, a suitable amount of the composition cured on the substrate is applied and irradiated at a belt speed of 3 m / min. Then, the cured layer is separated from the substrate and the thickness (μm) of the cured layer is checked. The thicker the layer, the better the complete curing of the test composition. In addition, the number of runs at 10 m / min necessary to prepare the non-tacky cured layer is checked (the number of runs (n) x 10 m / min). The photoinitiator used, the optical brightener and the measurement results are shown in Table 3.
* 비측정 값* Unmeasured value
RUVITEX OB, 시바 스페치알리테텐케미사 제조 R UVITEX OB, manufactured by Ciba Sp.
실시예 4: 폴리에스테르 아크릴레이트 백색 표면 피복물의 경화Example 4: Curing of Polyester Acrylate White Surface Coatings
조성이 실시예 2에서 언급한 바와 같은 백색 표면 피복물을 제조한다. 개시제 P3을 광 개시제로서 사용한다.Prepare a white surface coating whose composition is as mentioned in Example 2. Initiator P3 is used as the photoinitiator.
실시예 1에서 언급한 바와 같이, 도포와 경화를 수행한다. 각각의 경우, 경화 후에 3m/min의 벨트 속도로 진자 경도를 측정한다. 진자 경도 이외에, 실시예 3에서 언급한 바와 같은 최대 경화성 유리 층 깊이(FL)를 확인한다. 사용한 형광증백제와 측정 결과는 표 4에 기재되어 있다.As mentioned in Example 1, application and curing are carried out. In each case, pendulum hardness is measured at a belt speed of 3 m / min after curing. In addition to the pendulum hardness, the maximum curable glass layer depth (FL) as mentioned in Example 3 is determined. The fluorescence brighteners used and the measurement results are listed in Table 4.
본 발명에 의해, 신속하고 완전 경화 특성이 우수한 착색된 광 경화성 조성물이 제조된다.According to the present invention, colored photocurable compositions having fast and complete curing properties are produced.
Claims (16)
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KR (1) | KR19990072925A (en) |
DE (1) | DE19907957A1 (en) |
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KR100778199B1 (en) * | 2000-07-07 | 2007-11-27 | 린텍 가부시키가이샤 | Ultraviolet-curable pressure sensitive adhesive composition and ultraviolet-curable pressure sensitive adhesive sheet |
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WO2001018130A1 (en) * | 1999-09-02 | 2001-03-15 | Gmbh Clariant | Method for brightening workpieces by powder coating |
DE60006210T2 (en) | 1999-12-08 | 2004-07-15 | Ciba Specialty Chemicals Holding Inc. | New photoinitiator system made of phosphine oxide compounds and less colored curable compositions |
GB2365430B (en) | 2000-06-08 | 2002-08-28 | Ciba Sc Holding Ag | Acylphosphine photoinitiators and intermediates |
JP4993053B2 (en) * | 2001-02-27 | 2012-08-08 | 株式会社トクヤマ | Dental curable composition |
WO2002048202A1 (en) * | 2000-12-13 | 2002-06-20 | Ciba Specialty Chemicals Holding Inc. | Surface-active photoinitiators |
JP4812963B2 (en) * | 2001-05-18 | 2011-11-09 | リンテック株式会社 | Adhesive sheet for processing semiconductor wafer and method for processing semiconductor wafer |
DE10154420A1 (en) * | 2001-11-06 | 2003-05-28 | Carl V Ossietzky Uni Oldenburg | Light-curing plastic material with indicator to show the degree of curing |
CN1310707C (en) | 2002-01-29 | 2007-04-18 | 西巴特殊化学品控股有限公司 | Process for the production of strongly adherent coatings |
EP1349006B1 (en) * | 2002-03-28 | 2013-09-25 | Agfa Graphics N.V. | Photopolymerizable composition sensitized for the wavelength range from 300 to 450 nm. |
JP2003313208A (en) * | 2002-04-19 | 2003-11-06 | Meiko:Kk | Photocurable resin composition |
DE10307451A1 (en) * | 2003-02-21 | 2004-09-16 | Kodak Polychrome Graphics Gmbh | Radiation sensitive compositions and imageable elements based thereon |
EP1668417B1 (en) * | 2003-09-22 | 2009-05-13 | Agfa Graphics N.V. | Photopolymerizable composition. |
JP4813900B2 (en) * | 2005-03-31 | 2011-11-09 | 株式会社イーテック | UV-curable adhesive / adhesive composition having UV shielding properties |
JP5255369B2 (en) * | 2007-09-25 | 2013-08-07 | 富士フイルム株式会社 | Photocurable coating composition, overprint and method for producing the same |
WO2010089242A1 (en) * | 2009-02-09 | 2010-08-12 | Huntsman Advanced Materials (Switzerland) Gmbh | Powder coating composition |
DE102012212429A1 (en) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dental handset unit i.e. polymerization lamp, for invasive curing of light-curable material in e.g. dental cavity in mouth of human patient, has removable body separable together with control unit from non-destructive autoclavable handgrip |
WO2015104972A1 (en) * | 2014-01-08 | 2015-07-16 | Dic株式会社 | Activating energy beam-curable composition for flooring material |
WO2017115755A1 (en) * | 2015-12-28 | 2017-07-06 | 積水化学工業株式会社 | Photocurable composition and method for producing electronic component |
JP6950257B2 (en) * | 2017-04-18 | 2021-10-13 | コニカミノルタ株式会社 | Active light curable inkjet ink |
WO2019048963A1 (en) * | 2017-09-11 | 2019-03-14 | 3M Innovative Properties Company | Radiation curable compositions and composite articles made using an additive manufacturing process |
CN107987209B (en) * | 2018-01-08 | 2023-05-02 | 无锡佶达德光电子技术有限公司 | Coumarin polymer semiconductor laser material and application thereof |
EP3669853B1 (en) | 2018-12-21 | 2022-03-30 | Ivoclar Vivadent AG | Compositions for the preparation of fracture-resistant dental workpieces by means of stereolithography |
EP3669856A1 (en) | 2018-12-21 | 2020-06-24 | Ivoclar Vivadent AG | Compositions for the production of transparent dental workpieces by means of stereolithography |
CN110105166A (en) * | 2019-04-30 | 2019-08-09 | 同济大学 | Alpha-hydroxy ketones and its preparation method and application containing talan |
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RU2091385C1 (en) * | 1991-09-23 | 1997-09-27 | Циба-Гейги АГ | Bisacylphosphine oxides, composition and method of application of coatings |
US5707781A (en) * | 1995-05-05 | 1998-01-13 | Bayer Corporation | Photopolymerizable compositions having acyl or diacyl phosphine oxide and a fluorescent optical brightner |
US5660968A (en) * | 1995-05-05 | 1997-08-26 | Bayer Corporation | Negative working, peel developeable, single sheet color proofing system with improved background color |
GB9605712D0 (en) * | 1996-03-19 | 1996-05-22 | Minnesota Mining & Mfg | Novel uv-curable compositions |
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1999
- 1999-02-24 IT IT1999MI000376A patent/IT1309578B1/en active
- 1999-02-24 DE DE19907957A patent/DE19907957A1/en not_active Withdrawn
- 1999-02-25 KR KR1019990006255A patent/KR19990072925A/en not_active Application Discontinuation
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KR100778199B1 (en) * | 2000-07-07 | 2007-11-27 | 린텍 가부시키가이샤 | Ultraviolet-curable pressure sensitive adhesive composition and ultraviolet-curable pressure sensitive adhesive sheet |
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DE19907957A1 (en) | 1999-09-02 |
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ITMI990376A1 (en) | 2000-08-24 |
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ES2153315A1 (en) | 2001-02-16 |
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