JP4896886B2 - 放射線硬化可能な被覆組成物 - Google Patents
放射線硬化可能な被覆組成物 Download PDFInfo
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- JP4896886B2 JP4896886B2 JP2007543769A JP2007543769A JP4896886B2 JP 4896886 B2 JP4896886 B2 JP 4896886B2 JP 2007543769 A JP2007543769 A JP 2007543769A JP 2007543769 A JP2007543769 A JP 2007543769A JP 4896886 B2 JP4896886 B2 JP 4896886B2
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- 239000008199 coating composition Substances 0.000 title claims description 43
- 230000005855 radiation Effects 0.000 title claims description 28
- -1 1-propyl- Chemical group 0.000 claims description 257
- 239000000203 mixture Substances 0.000 claims description 45
- 150000001450 anions Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000003973 paint Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000004566 building material Substances 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- UASQKKHYUPBQJR-UHFFFAOYSA-M 4-decylbenzenesulfonate Chemical compound CCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 UASQKKHYUPBQJR-UHFFFAOYSA-M 0.000 claims description 2
- KWXICGTUELOLSQ-UHFFFAOYSA-M 4-dodecylbenzenesulfonate Chemical compound CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-M 0.000 claims description 2
- AUHUWFIYJDRPJX-UHFFFAOYSA-N 4-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=C(S(O)(=O)=O)C=C1 AUHUWFIYJDRPJX-UHFFFAOYSA-N 0.000 claims description 2
- MSOTUIWEAQEETA-UHFFFAOYSA-M 4-octylbenzenesulfonate Chemical compound CCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 MSOTUIWEAQEETA-UHFFFAOYSA-M 0.000 claims description 2
- 239000002969 artificial stone Substances 0.000 claims description 2
- 239000011449 brick Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011505 plaster Substances 0.000 claims description 2
- 238000010079 rubber tapping Methods 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 28
- 239000000975 dye Substances 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 16
- 230000001235 sensitizing effect Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 9
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000002250 absorbent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229910017008 AsF 6 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910020366 ClO 4 Inorganic materials 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910018286 SbF 6 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 3
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- 150000003457 sulfones Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-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
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- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NKIFVPLJBNCZFN-UHFFFAOYSA-N phenacyl(diphenyl)sulfanium Chemical compound C=1C=CC=CC=1C(=O)C[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NKIFVPLJBNCZFN-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- CKFPWZPBRHQASN-UHFFFAOYSA-N phenyl-(4-propan-2-ylphenyl)methanone Chemical compound C1=CC(C(C)C)=CC=C1C(=O)C1=CC=CC=C1 CKFPWZPBRHQASN-UHFFFAOYSA-N 0.000 description 1
- HUCRPDCCPSDJHT-UHFFFAOYSA-N phenyl-(4-propoxyphenyl)methanone Chemical compound C1=CC(OCCC)=CC=C1C(=O)C1=CC=CC=C1 HUCRPDCCPSDJHT-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002186 photoactivation Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- GFVKHYGXCQWRON-UHFFFAOYSA-N tributyl(ethyl)azanium Chemical compound CCCC[N+](CC)(CCCC)CCCC GFVKHYGXCQWRON-UHFFFAOYSA-N 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- VZUBRRXYUOJBRS-UHFFFAOYSA-N trichloromethylsulfonylbenzene Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=CC=C1 VZUBRRXYUOJBRS-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
Description
(A)シアニン−カチオンCya+1個及び相応するアニオン1/m Anm−1個からイオン構成されている吸収剤
{この際、シアニン−カチオンは、一般式(I)、(II)、(III)又は(IV):
− R1及びR2は相互に無関係に、C−原子数1〜20を有する線状の又は分枝した、
置換又は非置換のアルキル−又はアラルキル基、
− R3及びR4は相互に無関係に、H、CF3又はCN、
− R5及R6は相互に無関係に、群 −H、−F、−Cl、−Br、−I、−NO2、
−CN、−CF3、−SO2CF3、−R1、−OR1、アリール−又は−O−ア
リールから選択される同種又は異種の置換基1個以上、
− R7は、−H、−Cl、−Br、−I、−フェニル、−O−フェニル、−S−フェニ
ル、−N(フェニル)2、−ピリジル、バルビツール酸−又はジメドン基、ここで、
フェニル基は、なお更に置換されていてもよい、
− R8及びR9は相互に無関係に、>C(CH3)2、−O−、−S−、>NR1又は
−CH=C− ]を有し、
かつ、この際、アニオンAnm−は、極性のイオン性ヘッド基A 1個並びに非極性基
R10 k個を有する、一般式 [AR10 k]m−
[kは、1、2又は3の数であり、mは1又は2であり、かつ
非極性基R10は相互に無関係に、次の群:
− C−原子数6〜30を有する、線状の、分枝した又は環状のアルキル基並びに
− 一般式 −アリール−R11のアルキルアリール基
から選択され、ここで、R11はC−原子数3〜30を有する、線状の又は分枝したアルキル基である]を有するか、
又はアニオンAnm−は、一般式(V)又は(VI):
この際、基R10、R11及びR12中で隣接していないC−原子は、場合によりO−原子で置換されていてもよく、かつ/又は基R10、R11及びR12は全て又は部分的に、基の非極性が実質的に影響されないことを条件として、弗素化されていてよい]のボレート−アニオンである}少なくとも1種及び
(B)1個の会合した対イオン1/x Katx+を有する、式(VII):
z1、z2、z3及びz4は相互に無関係に、それぞれ0又は1であり、
この際、z1+z2+z3+z4の合計は0、1、2又は3、好ましくは0、1又は2、特に好ましくは0又は1、全く特別好ましくは0であり、
Y1、Y2、Y3及びY4は相互に無関係に、それぞれ、O、S又はNR17であり、
R13、R14、R15及びR16はそれぞれ相互に無関係に、C1〜C18−アルキル、場合により1個以上の酸素−及び/又は硫黄原子によって及び/又は1個以上の置換又は非置換のイミノ基によって中断されたC2〜C18−アルキル、C6〜C12−アリール、C5〜C12−シクロアルキル基であるか又は酸素−、窒素−及び/又は硫黄原子を有する5〜6員のヘテロ環であり、ここで、記載の基はそれぞれ、アリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環で置換されていてよく、かつ
R17は、水素、C1〜C18−アルキル又はC6〜C12−アリールを表す、
但し、基R13〜R16の少なくとも1つはC1〜C18−アルキル基であり、基R13〜R16の少なくとも1つはC6〜C12−アリール基であり、この際、記載の基は、それぞれアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環で置換されていてよいことを条件とする]の共−開始剤少なくとも1種
を含有する混合物によって解決された。
場合により1個以上の酸素−及び/又は硫黄原子によって及び/又は1個以上の置換又は非置換のイミノ基によって中断されたC2〜C18−アルキルは、例えば5−ヒドロキシ−3−オキサ−ペンチル、8−ヒドロキシ−3,6−ジオキサ−オクチル、11−ヒドロキシ−3,6,9−トリオキサ−ウンデシル、7−ヒドロキシ−4−オキサ−ヘプチル、11−ヒドロキシ−4,8−ジオキサ−ウンデシル、15−ヒドロキシ−4,8,12−トリオキサ−ペンタデシル、9−ヒドロキシ−5−オキサ−ノニル、14−ヒドロキシ−5,10−オキサ−テトラデシル、5−メトキシ−3−オキサ−ペンチル、8−メトキシ−3,6−ジオキサ−オクチル、11−メトキシ−3,6,9−トリオキサ−ウンデシル、7−メトキシ−4−オキサ−ヘプチル、11−メトキシ−4,8−ジオキサ−ウンデシル、15−メトキシ−4,8,12−トリオキサ−ペンタデシル、9−メトキシ−5−オキサ−ノニル、14−メトキシ−5,10−オキサ−テトラデシル、5−エトキシ−3−オキサ−ペンチル、8−エトキシ−3,6−ジオキサ−オクチル、11−エトキシ−3,6,9−トリオキサ−ウンデシル、7−エトキシ−4−オキサ−ヘプチル、11−エトキシ−4,8−ジオキサ−ウンデシル、15−エトキシ−4,8,12−トリオキサ−ペンタデシル、9−エトキシ−5−オキサ−ノニル又は14−エトキシ−5,10−ジオキサ−テトラデシルを表す。
場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環で置換されたC6〜C12−アリールは、例えばフェニル、トリル、キシリル、α−ナフチル、β−ナフチル、4−ジフェニリル、クロロフェニル、ジクロロフェニル、トリクロロフェニル、ジフルオロフェニル、メチルフェニル、ジメチルフェニル、トリメチルフェニル、エチルフェニル、ジエチルフェニル、イソ−プロピルフェニル、t−ブチルフェニル、ドデシルフェニル、メトキシフェニル、ジメトキシフェニル、エトキシフェニル、ヘキシルオキシフェニル、メチルナフチル、イソプロピルナフチル、クロロナフチル、エトキシナフチル、2,6−ジメチルフェニル、2,4,6−トリメチルフェニル、2,6−ジメトキシフェニル、2,6−ジクロロフェニル、4−ブロモフェニル、2−又は4−ニトロフェニル、2,4−又は2,6−ジニトロフェニル、4−ジメチルアミノフェニル、4−アセチルフェニル、メトキシエチルフェニル又はエトキシメチルフェニルを表し、
場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環で置換されたC5〜C12−シクロアルキルは、例えばシクロペンチル、シクロヘキシル、シクロオクチル、シクロドデシル、メチルシクロペンチル、ジメチルシクロペンチル、メチルシクロヘキシル、ジメチルシクロヘキシル、ジエチルシクロヘキシル、ブチルシクロヘキシル、メトキシシクロヘキシル、ジメトキシシクロヘキシル、ジエトキシシクロヘキシル、ブチルチオシクロヘキシル、クロロシクロヘキシル、ジクロロシクロヘキシル、ジクロロシクロペンチル並びに飽和又は不飽和の二環系並びに例えばノルボルニル又はノルボルネニルを表し、かつ
酸素−、窒素−及び/又は硫黄原子を有する5〜6員のヘテロ環は、例えばフリル、チオフェニル、ピリル、ピリジル、インドリル、ベンズオキサゾリル、ジオキソリル、ジオキシル、ベンズイミダゾリル、ベンズチアゾリル、ジメチルピリジル、メチルキノリル、ジメチルピリル、メトキシフリル、ジメトキシピリジル、ジフロオロピリジル、メチルチオフェニル、イソプロピルチオフェニル又はt−ブチルチオフェニルを表す。
R1及びR2は相互に無関係に、C−原子数1〜20を有する線状の又は分枝したアルキル−又はアラルキル基を表す。例には、メチル−、エチル−、1−プロピル−、2−プロピル−、1−ブチル−、2−ブチル−、t−ブチル−、1−ペンチル−、1−ヘキシル−、2−エチル−1−ヘキシル−、1−オクチル−、1−デシル−又は1−ドデシル基が包含される。殊に線状のアルキル基がこれに該当する。基としてはメチル−、エチル−、1−ブチル−又は1−ドデシル基が好ましい。原則的に公知のように、アラルキル基は、アリール基で置換されたアルキル基である。例には、ベンジル−又はフェニルエチル基が包含される。R1及びR2は、同様な又は相互に異なるものであってよい。R1及びR2は同種の基であるのが好ましい。
− 前記のような式1/m Anm−Cya+の成分(A)少なくとも1種及び
− 好ましくは式(VII)(対イオン1/x Katx+を有する)の成分(B)少なくとも1種
を含有している。
R21−I+−R22 AnB−
[式中、R21及びR22は置換又は非置換のアリール基を表し、AnB−はアニオンを表す]のものが有利である。
R26は置換又は非置換のアルキル基、置換又は非置換のアリール基又は置換又は非置換のベンゾイル基、好ましくは式−R25−(CO)−を表す]のものが好ましい。
− 前記のような式 1/m Anm−Cya+の成分(A)少なくとも1種、
− 好ましくは式(VII)の成分(B)(対イオン1/x Katx+を有する)少なく
とも1種 及び
− 場合により溶剤(C)少なくとも1種
から成っている。
〜1:5、特に好ましくは1:1〜1:4、全く特別に好ましくは1:2〜1:4である。
− 前記のような式1/m Anm−Cya+の成分(A)少なくとも1種及び
− 好ましく対イオン1/x Katx+を有する、式(VII)の成分(B)少なく
とも1種、
− 場合により溶剤(C)少なくとも1種、
− バインダー(D)少なくとも1種、
− 場合により反応性希釈剤(E)少なくとも1種、
− 場合によりUV−光開始剤(F)少なくとも1種、
− 場合により着色剤(G)少なくとも1種及び
− 場合により他の典型的な塗料添加剤(H)。
ベンゾフェノンは、例えばベンゾフェノン、4−アミノベンゾフェノン、4,4’−ビス(ジ−メチルアミノ)ベンゾフェノン、4−フェニルベンゾフェノン、4−クロロベンゾフェノン、ミヒラーケトン、o−メトキシベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4−メチルベンゾフェノン、2,4−ジメチルベンゾフェノン、4−イソプロピルベンゾフェノン、2−クロロベンゾフェノン、2,2’−ジクロロベンゾフェノン、4−メトキシベンゾフェノン、4−プロポキシベンゾフェノン又は4−ブトキシベンゾフェノンであり、
α−ヒドロキシ−アルキル−アリール−ケトンは、例えば1−ベンゾイルシクロヘキサン−1−オール(1−ヒドロキシ−シクロヘキシル−フェニルケトン)、2−ヒドロキシ−2,2’−ジメチルアセトフェノン(2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン)、1−ヒドロキシアセトフェノン、1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン又は2−ヒドロキシ−2−メチル−1−(4−イソプロペン−2−イル−フェニル)−プロパン−1−オンを重合導入含有しているポリマーであり、
キサントン及びチオキサントンは、例えば10−チオキサンテンオン、チオキサンテン−9−オン、キサンテン−9−オン、2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジ−イソプロピルチオキサントン、2,4−ジクロロチオキサントン又はクロロキサンテノンであり、
アントラキノンは、例えばβ−メチルアントラキノン、t−ブチルアントラキノン、アントラキノンカルボン酸エステル、ベンズ[de]アントラセン−7−オン、ベンズ[a]アントラセン−7,12−ジオン、2−メチルアントラキノン、2−エチルアントラキノン、2−t−ブチルアントラキノン、1−クロロアントラキノン又は2−アミルアントラキノンであり、
アセトフェノンは、例えばアセトフェノン、アセトナフトキノン、バレロフェノン、ヘキサノフェノン、α−フェニルブチロフェノン、p−モルホリノプロピオフェノン、ジベンゾスベロン、4−モルホリノベンゾフェノン、p−ジアセチルベンゼン、4’−メトキシアセトフェノン、α−テトラロン、9−アセチルフェナンスレン、2−アセチルフェナンスレン、3−アセチルフェナンスレン、3−アセチルインドール、9−フルオレノン、1−インダノン、1,3,4−トリアセチルベンゼン、1−アセトナフトン、2−アセトナフトン、2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン、1−ヒドロキシアセトフェノン、2,2−ジエトキシアセトフェノン、2−メチル−1−[4−(メチルチオ)−フェニル]−2−モルホリノプロパン−1−オン、2,2−ジメトキシ−1,2−ジフェニルエタン−2−オン又は2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタン−1−オンであり、
ベンゾイン又はベンゾインエーテルは、例えば4−モルホリノデオキシベンゾイン、ベンゾイン、ベンゾイン−イソブチルエーテル、ベンゾイン−テトラヒドロピラニルエーテル、ベンゾイン−メチルエーテル、ベンゾイン−エチルエーテル、ベンゾイン−ブチルエーテル、ベンゾイン−イソプロピルエーテル又は7−H−ベンゾイン−メチルエーテルであるか又は
ケタールは、例えばアセトフェノンジメチルケタール、2,2−ジエトキシアセトフェノン又はベンジルケタール、例えばベンジルジメチルケタールである。
改良された溶解度を有する本発明による一連のNIR−増感剤を合成した。
下記に、吸収剤2−[2−[2−[2−(1,3−ジヒドロ−1−エチル−3,3−ジメチル−2H−インドール−2−イリデン)−エチリデン]−1−シクロヘキセン−1−イル]エテニル]−1−エチル−3,3−ジメチル−3H−インドリウム ヨーダイド(B1)の合成を例示する。
2−[2−[2−[2−(1,3−ジヒドロ−1−エチル−3,3−ジメチル−2H−インドール−2−イリデン)−エチリデン]−1−シクロヘキセン−1−イル]エテニル]−1−エチル−3,3−ジメチル−3H−インドリウム ドデシルスルホネート(A1)
次のようにして化合物を製造した:NIR−増感剤A1 0.003モル(1.6g)を、Na−ドデシルスルホネート0.009モル(2.3g)と一緒にジクロロメタン50ml中に予め装入した。水50mlを加え、室温で30分間撹拌し、最後に相を分離させた。洗浄水中に硝酸銀溶液でヨウ素がもはや検出できなくなるまで、有機相を、水50mlで3回洗浄した。有機相を硫酸ナトリウムで乾燥の後に、溶剤を留去し、残分を真空中、50℃で乾燥させた。
この試験のために、アクリレートタイプの通常のラジカル重合可能な塗料原料2種(Laromer(R)LR8863及びLaromer(R)LRPO84F、双方ともBASF AG)を使用した。
前記の双方の塗料原料に、それぞれNIR−増感剤0.5質量%及びボラネート塩X−1.5質量%を加え、この混合物を激しく撹拌した。スぺーサーシートを有する2枚のガラス板の間で、得られた混合物を用いてそれぞれ薄い層(層厚 約50μm)を製造した。これらの層に、250W−ハロゲンランプ(間隔 約15cm)で1分間露光させた。
本発明によらないNIR−増感剤B7、B11、B12は、塗料原料中に、それぞれ完全には溶けなかった。露光の後に完全には硬化されていない塗膜が得られた。更に、塗料中に着色斑点(偏光顕微鏡下で、溶けていない結晶)が存在した。
本発明によるNIR−増感剤A7、A11、A12は、塗料原料中にそれぞれ完全に溶けた。4秒の露光時間の後に既に、硬くて澄明な塗膜が斑点不含で得られた。
Claims (12)
- 以下の成分(A)及び(B):
(A) シアニン−カチオンCya+少なくとも1個及び相応するアニオン1/m Anm−少なくとも1個からイオン構成されている増感剤
{この際、シアニン−カチオンは、一般式(I)、(II)、(III)又は(IV):
− R1及びR2は相互に無関係に、C−原子数1〜20を有する、線状の又は分枝した、アルキル−又はアラルキル基、
− R3及びR4は、H、
− R5及びR6は相互に無関係に、−H、−F、−Cl、−Br、−I、−NO2、
−CN、−CF3、−SO2CF3、−R1、−OR1、アリール−又は−O−ア
リールの群から選択される同種又は異種の置換基1個以上、
− R7は、−H、−Cl、−Br、−I、−フェニル、−O−フェニル、−S−フェニ
ル、−N(フェニル)2、−ピリジル、
− R8及びR9は相互に無関係に、>C(CH3)2、−O−、−S−、>NR1又は
−CH=CH−
を表す]を有し、
かつ、この際、アニオンAnm−は、式:
[AR10 k]m−
[式中、k=1であり、R10= −アリール−R11であり、この際、R11は、C−原子数3〜30を有する、線状の又は分枝したアルキル基であり、
Aは、−SO3 −、−OSO3 −、−COO−、−PO3 2−、−OPO3 2−又は
(−O)PO2 −から成る群から選択されており、
この際、基R10及びR11中で、隣接していないC−原子はO−原子で置換されていてもよい]を有する}少なくとも1種及び
(B)共−開始剤としてのアルキル置換されたボラネート塩少なくとも1種、
を含有している混合物。 - 以下の成分:
− 請求項1に定義されているような、式1/m Anm−Cya+の成分(A)少なくとも1種、
− 共−開始剤(B)としてのアルキル置換されたボラネート塩少なくとも1種及び
− 溶剤(C)少なくとも1種
から成っている混合物。 - 以下の成分:
− 請求項1に定義されているような、式1/m Anm−Cya+の成分(A)少なくとも1種、
− 共−開始剤(B)としてのアルキル置換されたボラネート塩少なくとも1種、
− 溶剤(C)少なくとも1種、
− バインダー(D)少なくとも1種、
− 反応性希釈剤(E)少なくとも1種、
− UV−光開始剤(F)少なくとも1種、
− 着色剤(G)少なくとも1種及び
− 他の典型的な塗料添加剤(H)
を含有している被覆組成物。 - 共−開始剤(B)は、会合した対イオン1/x Katx+を1個有する、
式(VII):
z1、z2、z3及びz4は相互に無関係に、それぞれ0又は1であり、
ここで、z1+z2+z3+z4の合計は、0、1、2又は3であり、
Y1、Y2、Y3及びY4は相互に無関係に、それぞれO、S又はNR17であり、
R13、R14、R15及びR16はそれぞれ相互に無関係に、C1〜C18−アルキル、1個以上の酸素−及び/又は硫黄原子によって及び/又は1個以上のイミノ基によって中断されたC2〜C18−アルキル、C6〜C12−アリール、C5〜C12−シクロアルキルを表すか又は酸素−、窒素−及び/又は硫黄原子を有する5〜6員のヘテロ環であり、この際、記載の基はそれぞれ、アリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環により置換されていてよく、かつR17は、水素、C1〜C18−アルキル又はC6〜C12−アリールを表す、
但し、基R13〜R16の少なくとも1つは、C1〜C18−アルキル基であり、
基R13〜R16の少なくとも1つは、C6〜C12−アリール基であり、この際、記載の基は、それぞれ、アリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又はヘテロ環により置換されていてよい]の化合物であることを特徴とする、請求項1又は2に記載の混合物又は請求項3に記載の被覆組成物。 - 請求項1中のR11は、1−プロピル−、2−プロピル−、1−ブチル−、2−ブチル−、t−ブチル−、1−ペンチル−、1−ヘキシル−、シクロヘキシル−、2−エチル−1−ヘキシル−、1−オクチル−、1−ノニル、1−デシル−、1−ウンデシル−、1−ドデシル−及び1−テトラデシル基から成る群から選択されていることを特徴とする、請求項1又は2に記載の混合物又は請求項3に記載の被覆組成物。
- アニオンAnm−は、C−原子数6〜12を有するアルキル基を有する4−アルキルベンゼンスルホネートであることを特徴とする、請求項1又は2に記載の混合物又は請求項3に記載の被覆組成物。
- アニオンAnm−は、4−ヘキシルベンゼンスルホネート、4−オクチルベンゼンスルホネート、4−デシルベンゼンスルホネート及び4−ドデシルベンゼンスルホネートから成る群から選択されていることを特徴とする、請求項1又は2に記載の混合物又は請求項3に記載の被覆組成物。
- 放射線硬化可能な被覆組成物中での、並びに建築材料、煉瓦、クリンカー、人造石材、たたき床又は漆喰、又はそれらの被覆用の被覆組成物を硬化させるための、請求項1、2、4から7までのいずれか1項に記載の混合物の使用。
- バインダー(D)少なくとも1種及び/又は反応性希釈剤(E)少なくとも1種を含有する放射線硬化可能な被覆組成物を製造する方法において、バインダー(D)及び/又は反応性希釈剤(E)を、請求項1、2、4から7までのいずれか1項に記載の混合物と混合することを特徴とする、放射線硬化可能な被覆組成物を製造する方法。
- バインダー(D)少なくとも1種及び/又は反応性希釈剤(E)少なくとも1種を含有する放射線硬化可能な被覆組成物を製造する方法において、バインダー(D)及び/又は反応性希釈剤(E)を、請求項1に記載のように定義されている式1/m Anm−Cya+の成分(A)少なくとも1種と混合し、及びそれとは別に、成分(B)としてのアルキル置換されたボラネート塩少なくとも1種と混合することを特徴とする、放射線硬化可能な被覆組成物を製造する方法。
- NIR−線の照射によって、NIR−光開始剤として請求項1に記載の混合物少なくとも1種及びラジカル重合可能な化合物少なくとも1種を含有する被覆組成物を硬化させる方法において、この照射を、18kPaより低い酸素分圧下で実施することを特徴とする、NIR−線の照射によって被覆組成物を硬化させる方法。
- 少なくとも1種の不活性ガスを含有する雰囲気中で硬化を実施することを特徴とする、請求項11に記載の方法。
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KR20100099048A (ko) * | 2009-03-02 | 2010-09-10 | 주식회사 동진쎄미켐 | 감광성 수지 조성물 |
WO2011052604A1 (ja) * | 2009-10-26 | 2011-05-05 | 独立行政法人産業技術総合研究所 | 光応答性イオン性有機化合物及びその製法、並びに該イオン性有機化合物からなる光応答性カーボンナノチューブ分散剤 |
EP2450893A1 (de) * | 2010-11-08 | 2012-05-09 | Bayer MaterialScience AG | Photopolymer-Formulierung zur Herstellung holographischer Medien mit hoch vernetzten Matrixpolymeren |
TW201710405A (zh) * | 2015-06-23 | 2017-03-16 | 科思創德意志股份有限公司 | 含有經鏈取代之花青染料的全像媒體 |
CN107300830B (zh) * | 2016-04-15 | 2021-03-30 | 常州强力电子新材料股份有限公司 | 一种新型光固化组合物及其应用 |
WO2019039136A1 (ja) * | 2017-08-21 | 2019-02-28 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
EP3501837A1 (en) * | 2017-12-21 | 2019-06-26 | Université de Haute Alsace | Thermal amplification of free radical polymerization induced by red to near-infrared irradiation |
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- 2005-12-01 WO PCT/EP2005/012795 patent/WO2006058731A2/de active Application Filing
- 2005-12-01 US US11/720,788 patent/US20100126386A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
CN101069129B (zh) | 2010-12-08 |
US20100126386A1 (en) | 2010-05-27 |
WO2006058731A3 (de) | 2006-10-05 |
JP2011149029A (ja) | 2011-08-04 |
JP2008521982A (ja) | 2008-06-26 |
CN101069129A (zh) | 2007-11-07 |
DE102004058584A1 (de) | 2006-06-08 |
EP1820064A2 (de) | 2007-08-22 |
WO2006058731A2 (de) | 2006-06-08 |
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