JP2017533288A - 多環式光開始剤 - Google Patents
多環式光開始剤 Download PDFInfo
- Publication number
- JP2017533288A JP2017533288A JP2017512391A JP2017512391A JP2017533288A JP 2017533288 A JP2017533288 A JP 2017533288A JP 2017512391 A JP2017512391 A JP 2017512391A JP 2017512391 A JP2017512391 A JP 2017512391A JP 2017533288 A JP2017533288 A JP 2017533288A
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- Prior art keywords
- alkyl
- formula
- compound
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- iii
- Prior art date
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- 125000003367 polycyclic group Chemical group 0.000 title description 6
- -1 2-tetrahydropyranyl Chemical group 0.000 claims abstract description 130
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 133
- 238000000576 coating method Methods 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 30
- 239000000976 ink Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 27
- 238000007639 printing Methods 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 15
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 238000007650 screen-printing Methods 0.000 claims description 11
- 229920002120 photoresistant polymer Polymers 0.000 claims description 10
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 9
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 239000003365 glass fiber Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 238000007641 inkjet printing Methods 0.000 claims description 4
- 239000003094 microcapsule Substances 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 3
- 238000001459 lithography Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 239000002966 varnish Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 239000011152 fibreglass Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 26
- 238000004519 manufacturing process Methods 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 238000009472 formulation Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- 238000001723 curing Methods 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000000049 pigment Substances 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000000123 paper Substances 0.000 description 10
- 238000000016 photochemical curing Methods 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 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 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 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
- 239000008199 coating composition Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 125000001841 imino group Chemical group [H]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
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000007645 offset printing Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
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- 239000000499 gel Substances 0.000 description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 239000004642 Polyimide Substances 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
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- 125000005409 triarylsulfonium group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- 235000014692 zinc oxide Nutrition 0.000 description 3
- 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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000021317 phosphate Nutrition 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001603 poly (alkyl acrylates) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 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
- 238000004382 potting Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- SOGFHWHHBILCSX-UHFFFAOYSA-J prop-2-enoate silicon(4+) Chemical compound [Si+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C SOGFHWHHBILCSX-UHFFFAOYSA-J 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 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
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010125 resin casting Methods 0.000 description 1
- 229920003987 resole Polymers 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
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 239000011734 sodium Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009788 spray lay-up Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-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
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 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
- 239000008096 xylene Substances 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
Classifications
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
Abstract
Description
光重合性組成物であって、
(A) 少なくとも1種のエチレン性不飽和光重合性化合物と、
(B) 少なくとも1種の式(I)の光開始剤、
Xは、O、S、直接結合又はCR16R17であり、
Yは、O又はSであり、
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立に、水素、ハロゲン、C1−C4アルキル、C5−C7シクロアルキル、フェニル、C1−C4アルコキシ、C5−C7シクロアルコキシ、フェノキシ、C1−C4アルキルチオ、C5−C7シクロアルキルチオ、フェニルチオ、ジ(C1−C4アルキル)アミノ、ジ(C5−C7シクロアルキル)アミノ、N−モルフォリニル、N−ピペリジニル又は式(II)若しくは(III)の基であるが、
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(II)又は(III)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が、式(II)又は(III)の基であり、且つR5、R6、R7又はR8うち1個が、式(II)又は(III)の基であり;
R9及びR10は、互いに独立に、C1−C4アルキルであるか、又は、それらが結合するC原子と一緒に5員、6員又は7員の炭素環を形成し;
R11は、水素、C1−C4アルキル、C5−C7シクロアルキル、2−テトラヒドロピラニル又はSi(C1−C4アルキル)3であり;
R12及びR13は、互いに独立に、C1−C4アルキル、C2−C12アルケニル、フェニル−C1−C4アルキル、C1−C4アルキルで置換されたフェニル−C1−C4アルキルであるか、又は、R12及びR13は、それらが結合するC原子と一緒に5員、6員又は7員の炭素環を形成し;
R14及びR15は、互いに独立に、C1−C4アルキル、C5−C7シクロアルキルであるか、又は、それらが結合するN原子と一緒に5員、6員又は7員環を形成し、当該環は、更にヘテロ原子O、S又はNを含んでいてもよく;
R16及びR17は、互いに独立に、水素、C1−C8アルキル、C5−C7シクロアルキル、フェニル−C1−C4アルキル、フェニルであるか、又は、それらが結合するC原子と一緒に5員、6員又は7員環を形成し;
但し、
(1) R2が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、且つXが、直接結合であり、且つYがOである化合物;
(2) R2が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、且つX及びYがSである化合物;及び
(3) R7が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、且つX及びYがSである化合物;
は除かれる。)
とを有する上記光重合性組成物である。
Xは、O、S、直接結合又はCR16R17であり;
Yは、O又はSであり;
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立に、水素、ハロゲン、C1−C4アルキル、C5−C7シクロアルキル、フェニル、C1−C4アルコキシ、C5−C7シクロアルコキシ、フェノキシ、C1−C4アルキルチオ、C5−C7シクロアルキルチオ、フェニルチオ、ジ(C1−C4アルキル)アミノ、ジ(C5−C7シクロアルキル)アミノ、N−モルフォリニル、N−ピペリジニル又は式(II)の基であり;
R11は、水素、C1−C4アルキル、C5−C7シクロアルキル、2−テトラヒドロピラニル又はSi(C1−C4アルキル)3である。)。
C1−C4アルキルチオは、直鎖状又は分岐状であり、メチルチオ、エチルチオ、プロピルチオ、イソプロピルチオ、n−ブチルチオ、sec−ブチルチオ、iso−ブチルチオ又はtert−ブチルチオ、好ましくはメチルチオである。
但し、R1、R2、R3、R4、R5、R6、R7及びR8の少なくとも1個が水素であり;
X及びYは、請求項14に定義する通りである。)の、
ハロゲン化物(IIa)又は酸無水物(IVa)
Halは、ハロゲン化物、好ましくは塩化物である。)によるFriedel−Craftsアシル化;
2. 続いて、得られたFriedel−Crafts付加物のハロゲン化、特にブロム化;
3. ハロゲン化中間体の加水分解により、請求項14に定義する式(I”)の対応するα−ヒドロキシケトン化合物を得る。
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(II)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が式(II)の基であり、且つR5、R6、R7又はR8のうち1個が式(II)の基である。
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(II)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が式(II)の基であり、且つR5、R6、R7又はR8のうち1個が式(II)の基であり;
R9及びR10が、メチルであるか、又はそれらが結合するC原子と一緒に6員の炭素環を形成し;
R11が、水素である。
R1からR4及びR5からR8の残りの基が、独立に、水素、ハロゲン、C1−C4アルキル、C1−C4アルコキシ、C1−C4アルキルチオ、N−モルフォリニル又はN−ピペリジニルである。
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(III)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が式(III)の基であり、且つR5、R6、R7又はR8のうち1個が式(III)の基である。
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(III)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が式(III)の基であり、且つR5、R6、R7又はR8のうち1個が式(III)の基であり;
R12及びR13が、C1−C2アルキル又はベンジルであり;
R14及びR15が、C1−C4アルキルであるか、又は、それらが結合するN原子と一緒に6員環を形成し、当該環は、さらなるヘテロ原子O又はNを含みうる。
R1からR4及びR5からR8の残りの基が、独立に、水素、ハロゲン、C1−C4アルキル、C1−C4アルコキシ、C1−C4アルキルチオ、N−モルフォリニル又はN−ピペリジニルである。
特に、R1からR4及びR5からR8の残りの基が、水素である。
R1、R2、R3又はR4のうち1個、且つR5、R6、R7又はR8のうち1個が、式(II)の基であるか;又は
R1、R2、R3又はR4のうち1個、且つR5、R6、R7又はR8のうち1個が、式(III)の基である。
Xが、S、直接結合又はCR16R17であり;
Yが、O又はSであり;
R1、R3、R4、R5、R6及びR8が水素であり;
R2及びR7が、式(II)又は(III)の基であり;
R9及びR10が、C1−C4アルキル、特にメチルであり;
R11が、水素であり;
R12及びR13が、C1−C4アルキル、特にメチルであり;
R14及びR15が、C1−C4アルキル、特にメチルであり;
R16及びR17が、水素又はC1−C8アルキル、特にメチルである。
Xが、S、直接結合又はCR16R17であり;
Yが、O又はSであり;
R1、R3、R4、R5、R6及びR8が水素であり;
R2及びR7が、式(II)の基であり;
R9及びR10が、C1−C4アルキル、特にメチルであり;
R11が、水素であり;
R12及びR13が、C1−C4アルキル、特にメチルであり;
R14及びR15が、C1−C4アルキル、特にメチルであり;
R16及びR17が、水素又はC1−C8アルキル、特にメチルである。
あるいは、Xは、例えば、S、直接結合又はCR16R17である。
あるいは、R11は、水素、C1−C4アルキル、C5−C7シクロアルキル又は2−テトラヒドロピラニルである。
あるいは、R11は、水素、C1−C4アルキル又はC5−C7シクロアルキル、特に水素又はC1−C4アルキルである。好ましくは、R11は、水素である。
したがって、本発明は、下記を有する光重合性組成物にも関する:
(A) 少なくとも1種のエチレン性不飽和光重合性化合物と、
(B) 少なくとも1種の上記に定義する式(I”)の光開始剤。
トリメチロールプロパン トリアクリレート、トリメチロールエタン トリアクリレート、トリメチロールプロパン トリメタクリレート、トリメチロールエタン トリメタクリレート、テトラメチレングリコール ジメタクリレート、トリエチレングリコール ジメタクリレート、テトラエチレングリコール ジアクリレート、ペンタエリスリトール ジアクリレート、ペンタエリスリトール トリアクリレート、ペンタエリスリトール テトラアクリレート、ジペンタエリスリトール ジアクリレート、ジペンタエリスリトール トリアクリレート、ジペンタエリスリトール テトラアクリレート、ジペンタエリスリトール ペンタアクリレート、ジペンタエリスリトール ヘキサアクリレート、トリペンタエリスリトール オクタアクリレート、ペンタエリスリトール ジメタクリレート、ペンタエリスリトール トリメタクリレート、ジペンタエリスリトール ジメタクリレート、ジペンタエリスリトール テトラメタクリレート、トリペンタエリスリトール オクタメタクリレート、ペンタエリスリトール ジイタコネート、ジペンタエリスリトール トリスイタコネート、ジペンタエリスリトール ペンタイタコネート、ジペンタエリスリトール ヘキサイタコネート、エチレングリコール ジアクリレート、1,3−ブタンジオール ジアクリレート、1,3−ブタンジオール ジメタクリレート、1,4−ブタンジオール ジイタコネート、ソルビトール トリアクリレート、ソルビトール テトラアクリレート、ペンタエリスリトール変性トリアクリレート、ソルビトール テトラメタクリレート、ソルビトール ペンタアクリレート、ソルビトール ヘキサアクリレート、オリゴエステル アクリレート及びメタクリレート、グリセロール ジアクリレート及びトリアクリレート、1,4−シクロヘキサンジアクリレート、分子量200から1500のポリエチレングリコールのビスアクリレート及びビスメタクリレート、又はこれらの混合物。
公知のさらなる添加剤を添加してもよく、例としては、帯電防止剤、流動性改良剤及び接着促進剤がある。
本組成物は、染料及び/又は白色や有色の顔料を有していてもよい。用途によって、有機や無機の顔料が用いられる。そのような添加剤は、当業者に知られており、例としては、二酸化チタン顔料、例えばルチル型又はアナタース型のもの、カーボンブラックRuss、酸化亜鉛、例えばジンクホワイト、酸化鉄、例えば酸化鉄イエロー、酸化鉄レッド等、クロムイエロー、クロムグリーン、ニッケルチタンイエロー、ウルトラマリンブルー、コバルトブルー、バナジン酸ビスマス、カドミウムイエロー又はカドミウムレッドである。有機顔料の例は、モノ又はビスアゾ顔料、また、その金属錯体、フタロシアニン顔料、多環式顔料、例えばペリレン、アンスラキノン、チオインディゴ、キナクリドン又はトリフェニルメタン顔料等、また、ジケト−ピロロ−ピロール、イソインドリノン、例えばテトラクロロイソインドリノン、イソインドリン、ジオキサジン、ベンゾイミダゾロン及びキノフタロン(chinophthalone)顔料がある。
本発明に係る組成物は、例えばPaint&Coatings Industry,April 1997,72又はPlastics World,vol.54,no.7,p48(5)に記載されるような乾燥塗膜に用いることもできる。
塩化イソブチロイル(26.64g、0.25mol)及びキサンテン(18.22g、0.1mol)を、100mlの1,2−ジクロロエタンに溶解し、溶液を−15℃に冷却する。次いで、撹拌溶液に、三塩化アルミニウム(33.3g、0.25mol)を、30分以内に−10℃から−15℃の間の温度にて添加する。次いで、得られる橙色の混合物を、室温で18時間撹拌し、その後、600gの氷、50mlの32%塩酸及び150mlのジクロロメタンからなる撹拌混合物中にゆっくりと注ぐ。有機層を分離し、50mlの5%塩酸、1M Na2CO3及び水で洗浄し、MgSO4上で乾燥し、蒸発させる。残渣をジクロロメタン−エタノールから再結晶させて、29.2gの標題化合物を融点125℃〜131℃の白色の固体として得る。1H−NMR(CDCl3,400MHz,δppm):7.83−7.81(m,4ArH),7.10−7.07(m,2ArH),4.13(s,2H,CH2),3.55−3.49(m,2H),1.21(d,12H)。
中間体I−1a(24.18g、0.075mol)を100mlのジクロロメタンに溶解し、溶液を3℃に冷却する。次いで、撹拌溶液に、臭素(24.0g、0.15mol)を75mlのジクロロメタンに溶解した溶液を、3℃から5℃の温度で1時間以内に添加する。次いで、混合物を室温で3時間撹拌し、200mlの冷水で希釈する。有機層を分離し、100mlの1M NaHCO3及び水で洗浄し、MgSO4上で乾燥し、蒸発させる。残渣をジクロロメタン−アセトニトリルから再結晶させて、26.5gの標題化合物を融点129℃〜138℃の白色の固体として得る。1H−NMR(CDCl3,400MHz,δppm):8.15−8.10(m,4ArH),7.10−7.08(m,2ArH),4.16(s,2H,CH2),2.08(s,12H)。
中間体I−1b(8.64g、0.018mol)を、35mlのテトラヒドロフランに溶解する。次いで、この溶液に、NaOH(2.88g、0.072mol)を14mlの水に溶解した溶液を添加する。得られる乳液を、室温で26時間激しく撹拌する。その後、ジクロロメタン(60ml)、水(100ml)及び1M HCl(40ml)を添加する。有機層を分離し、水で洗浄し、MgSO4上で乾燥し、蒸発させる。残渣を酢酸エチルから再結晶させて、5.1gの標題化合物を融点159℃〜162℃の白色の固体として得る。1H−NMR(CDCl3,400MHz,δppm):7.98−7.94(m,4ArH),7.11−7.08(m,2ArH),4.14(s,2H,CH2),4.04(s,2OH),1.63(s,12H)。
中間体I−2aを、中間体I−1aと同様にして、9,9−ジメチルキサンテンから収率85%で製造する。白色の固体、融点105℃〜109℃。1H−NMR(CDCl3,400MHz,δppm):8.15−8.14(d,2ArH),7.88−7.85(dd,2ArH),7.15−7.13(d,2ArH),3.61−3.54(m,2H),1.72(s,2xCH3)1.26−1.24(d,12H)。
中間体I−2bを、中間体I−1bと同様にして、中間体I−2aから収率89.3%で製造する。白色の固体、融点118℃〜130℃。1H−NMR(CDCl3,400MHz,δppm):8.38−8.37(d,2ArH),8.19−8.16(dd,2ArH),7.14−7.11(d,2ArH),2.08(s,12H),1.73(s,2xCH3)。
化合物2を、化合物1と同様にして、中間体I−2bから93.2%の収率で製造する。白色の固体、融点107℃〜119℃。1H−NMR(CDCl3,400MHz,δppm):8.27−8.26(d,2ArH),8.01−7.99(dd,2ArH),7.14−7.12(d,2ArH),4.09(bs,2xOH),1.72(s,2xCH3),1.66(s,12H)。
中間体I−3aを、中間体I−1aと同様にして、フェノキサチインから77%の収率(メタノールからの2度の結晶化後)で製造した。淡黄色の固体、融点82℃〜92℃。NMRによれば、これは約1:1の比で2種の位置異性体からなる。これらの位置異性体のイソブチロイル基は、おそらくフェノキサチイン環系のそれぞれ2,7位及び2,8位である。1H−NMR(CDCl3,400MHz、δppm):7.74−6.98(m,6ArH),3.48−3.41(m,2H),1.27−1.17(m,12H)。
中間体I−3bを、中間体I−1bと同様にして、中間体I−3aから収率91.5%で製造する。黄色の固体、融点104℃〜131℃。NMRによれば、これは約1:1の比で2種の位置異性体からなる。これらの位置異性体のイソブチロイル基は、おそらくフェノキサチイン環系のそれぞれ2,7位及び2,8位である。1H−NMR(CDCl3,400MHz,δppm):8.06−7.0(m,6ArH),2.04(s,6H),2.03(s,6H)。
化合物3を、化合物1、表1と同様にして、中間体I−3bから収率78%で製造する。黄色の固体、融点119℃〜125℃。NMRによれば、これは約1:1の比で2種の位置異性体からなる。これらの位置異性体のイソブチロイル基は、おそらくフェノキサチイン環系のそれぞれ2,7位及び2,8位である。1H−NMR(CDCl3,400MHz,δppm):7.89−7.0(m,6ArH),3.81(s,0H),3.79(s,OH),1.61(s,6H),1.60(s,6H)。
中間体I−4aを、中間体I−1aと同様にして、チアントレンから収率24.5%(アセトニトリルからの2回の結晶化後)で製造する。薄黄色の固体、融点98℃〜110℃。1H−NMR(CDCl3,400MHz,δppm):8.01−8.00(d,2ArH),7.83−7.80(dd,2ArH),7.54−7.52(d,2ArH),3.53−3.44(m,2CH),1.21−1.19(d,12H)。
中間体I−4bを、中間体I−1bと同様にして、中間体I−4aから95%の収率で製造する。黄色の固体、融点114℃〜118℃。1H−NMR(CDCl3,400MHz,δppm):8.22−8.21(d,2ArH),8.10−8.07(dd,2ArH),7.55−7.53(d,2ArH),2.03(s,12H)。
化合物4を、化合物1と同様にして、中間体I−4bから収率79%で製造する。黄色の固体、融点143℃〜147℃。1H−NMR(CDCl3,400MHz,δppm):7.76−7.75(d,2ArH),7.59−7.56(dd,2ArH),7.06−7.04(d,2ArH),3.31(s,0H),1.10(s,12H)。
中間体I−5aを、中間体I−1aと同様にして、ジベンゾフランから製造する。粗生成物は、粘性のある薄黄色のオイルとして収率99%で得られた。1H−NMR(CDCl3,400MHz,δppm):8.65−8.64(d,2ArH),8.17−8.14(dd,2ArH),7.66−7.64(d,2ArH),3.71−3.63(m,2CH),1.29−1.27(d,12H)。
中間体I−5bを、中間体I−1bと同様にして、中間体I−5aから収率69%(メタノールからの結晶化後)で製造する。生成色の固体、融点127℃〜160℃、1H−NMRによる純度約95%。1H−NMR(CDCl3,400MHz,δppm):8.89−8.88(d,2ArH),8.47−8.44(dd,2ArH),7.67−7.64(d,2ArH),2.14(s,12H)。
化合物5を、化合物1と同様にして、中間体I−5bから収率69.5%で製造する。白色の固体、融点121℃〜148℃、1H−NMRによる純度約95%。
1H−NMR(CDCl3,400MHz,δppm):8.81−8.80(d,2ArH),8.30−8.28(dd,2ArH),7.68−7.66(d,2ArH),3.89(bs,2OH),1.74(s,12H)。
2−ブロモ−1−[8−(2−ブロモ−2−メチル−プロパノイル)フェノキサチイン−2−イル]−2−メチル−プロパ−1−オン(中間体I−3b、24.91g、0.05mol)を150mlのメタノールに懸濁させた撹拌懸濁液に、ナトリウムメトキシド(5.94g、0.11mol)を45mlのメタノールに溶解した溶液を、30分以内に0℃にて添加する。次いで、混合物を室温で96時間撹拌し、減圧下でメタノールを蒸発させる。残渣を40mlの水及び150mlのジクロロメタンに溶解し、有機層を分離し、50mlの水で洗浄し、MgSO4上で乾燥し、蒸発させて、20.8gの粗製の表題化合物を濃黄色のオイルとして得る。1H−NMR(CDCl3,400MHz,δppm):7.28−7.01(m,6ArH),3.23−3.19(bs,2OCH3),1.50(bs,2xCH3),1.04(bs,2xCH3)。
350ml容のスチール製オートクレーブに、中間体I−6a(20.35g、約0.05mol)、40mlのキシレン及びジメチルアミン(14.25gの33%エタノール溶液、0.104mol)を仕込む。その後、オートクレーブを130℃で20時間加熱し、次いで室温まで冷却する。反応混合物を蒸発させ、油状の残渣について、酢酸エチル−ヘプタン1:6を用いてシリカゲル上でクロマトグラフを行う。純粋な画分をメタノールから2回再結晶させて、9.22gの表題化合物を融点138℃〜147℃の薄黄色の固体として得る。NMRによれば、これは約1:1の比率で2種の位置異性体からなる。これらの位置異性体のジメチルアミノ−イソブチロイル基は、おそらくフェノキサチイン環系のそれぞれ2,7位及び2,8位である。1H−NMR(CDCl3,400MHz,δppm):8.34−8.16(m,4ArH),7.10−6.97(m,2ArH),2.26(s,6H,CH3),2.25(s,6H,CH3),1.28(s,6H,CH3),1.27(s,6H,CH3)。
中間体I−7aを、中間体I−6aと同様にして、中間体I−2aから収率約99%(粗製)で濃黄色のオイルとして製造する。1H−NMR(CDCl3,400MHz,δppm):7.51−7.49(bs,2ArH),7.31−7.28(dd,2ArH),7.08−7.06(d,2ArH),3.21(s,2xOCH3),1.67(bs,2xCH3),1.56(s,2xCH3),1.03(s,2xCH3)。
化合物7を、化合物6、表1と同様にして、中間体I−7aから8%の収率で製造する。白色の固体、融点152℃から173℃、1H−NMRによる純度約95%。1H−NMR(CDCl3,400MHz,δppm):8.72(bs,2ArH),7.52−7.50(d,2ArH),7.02−7.0(d,2ArH),2.28(s4xCH3),1.68(s,2xCH3),1.28(s,4xCH3)。
実施例A1:ラジカル重合性透明コーティング配合物の光硬化
本発明の化合物を、下記の混合物からなる透明コート配合物において評価する:
20重量%のポリエステル−アクリレート Laromer(登録商標)PE9079(BASF)と、
80重量%のアミン修飾ポリエーテル−アクリレート Laromer(登録商標)PO94F(BASF)。
化合物2の光開始剤が、透明コーティング配合物及び青色フレキソインクの両方において高効率であることを考慮し、表4に詳細を示す黄色フレキソインク配合物についても評価を行う。
Claims (15)
- 下記を有する光重合性組成物:
(A) 少なくとも1種のエチレン性不飽和光重合性化合物と、
(B) 少なくとも1種の式(I)の光開始剤、
Xは、O、S、直接結合又はCR16R17であり、
Yは、O又はSであり、
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立に、水素、ハロゲン、C1−C4アルキル、C5−C7シクロアルキル、フェニル、C1−C4アルコキシ、C5−C7シクロアルコキシ、フェノキシ、C1−C4アルキルチオ、C5−C7シクロアルキルチオ、フェニルチオ、ジ(C1−C4アルキル)アミノ、ジ(C5−C7シクロアルキル)アミノ、N−モルフォリニル、N−ピペリジニル又は式(II)又は(III)の基であるが、
(i) R1、R2、R3、R4、R5、R6、R7又はR8のうち1個が、式(II)又は(III)の基であるか;
又は
(ii) R1、R2、R3又はR4のうち1個が、式(II)又は(III)の基であり、且つR5、R6、R7又はR8うち1個が、式(II)又は(III)の基であるか;
のいずれかであり;
R9及びR10は、互いに独立に、C1−C4アルキルであるか、又は、それらが結合するC原子と一緒に5員、6員又は7員の炭素環を形成し;
R11は、水素、C1−C4アルキル、C5−C7シクロアルキル、2−テトラヒドロピラニル又はSi(C1−C4アルキル)3であり;
R12及びR13は、互いに独立に、C1−C4アルキル、C2−C12アルケニル、フェニル−C1−C4アルキル、C1−C4アルキルで置換されたフェニル−C1−C4アルキルであるか、又は、R12及びR13は、それらが結合するC原子と一緒に5員、6員又は7員の炭素環を形成し;
R14及びR15は、互いに独立に、C1−C4アルキル、C5−C7シクロアルキルであるか、又は、それらが結合するN原子と一緒に5員、6員又は7員環を形成し、当該環は、さらにヘテロ原子O、S又はNを含んでいてもよく;
R16及びR17は、互いに独立に、水素、C1−C8アルキル、C5−C7シクロアルキル、フェニル−C1−C4アルキル、フェニルであるか、又は、それらが結合するC原子と一緒に5員、6員又は7員環を形成し;
但し、:
(1) R2が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、Xが、直接結合であり、且つYがOである化合物;
(2) R2が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、且つX及びYがSである化合物;及び
(3) R7が、式(III)の基であり、且つR14及びR15が、それらが結合するN原子と一緒に6員環を形成し、当該環が更にヘテロ原子Oを含み、且つX及びYがSである化合物;
は除かれる。)。 - 式(I)の光開始剤化合物において、
R1、R2、R3又はR4のうち1個、又はR5、R6;R7又はR8のうち1個が、式(II)又は(III)の基である、
請求項1に記載の光重合性組成物。 - 式(I)の光開始剤化合物において、
R1、R2、R3又はR4のうち1個、且つR5、R6;R7又はR8のうち1個が、式(II)又は(III)の基である、
請求項1に記載の光重合性組成物。 - 式(I)の光開始剤化合物において、
R1、R2、R3又はR4のうち1個、且つR5、R6、R7又はR8のうち1個が、式(II)の基であるか;又は
R1、R2、R3又はR4のうち1個、且つR5、R6、R7又はR8のうち1個が、式(III)の基である、
請求項1に記載の光重合性組成物。 - 式(I)の光開始剤化合物において、
Xが、S、直接結合又はCR16R17であり;
Yが、O又はSであり;
R1、R3、R4、R5、R6及びR8が、水素であり;
R2及びR7が、式(II)又は(III)の基であり;
R9及びR10が、C1−C4アルキル、特にメチルであり;
R11が、水素であり;
R12及びR13が、C1−C4アルキル、特にメチルであり;
R14及びR15が、C1−C4アルキル、特にメチルであり;
R16及びR17が、水素又はC1−C8アルキル、特にメチルである、
請求項1に記載の光重合性組成物。 - 成分(B)に加えて、下記を有する、請求項1に記載の光重合性組成物:
(x) 少なくとも1種のさらなる光開始剤(C);
(xi) 少なくとも1種のさらなる共開始剤(D);
(xii) 少なくとも1種の他の添加剤(D);又は
(xii) (x)及び(xi)の組み合わせ、若しくは(x)及び(xii)の組み合わせ、若しくは(x)、(xi)及び(xii)の組み合わせ。 - 全組成物に対して、式(I)の前記光開始剤化合物を0.05重量%から15重量%、好ましくは0.1重量%から10重量%有する、請求項1に記載の光重合性組成物。
- 少なくとも1個のエチレン性不飽和二重結合を含むモノマー、オリゴマー又はポリマー化合物の光重合方法であって、前記モノマー、オリゴマー又はポリマー化合物に、少なくとも1種の請求項1に定義する式(I)の光開始剤化合物又は少なくとも1種の請求項14に定義する式(I”)の光開始剤化合物を添加することと、得られる組成物に電磁波又は粒子線放射を照射することとを有する、方法。
- 着色及び無着色塗料及びワニス、パウダーコーティング、印刷用インク、例えばスクリーン印刷用インク、オフセット、フレキソ又はインクジェット印刷用のインク、印刷版、接着剤、シーリング、注型材、歯科用組成物、フォーム、成形用化合物、複合材組成物、グラスファイバーケーブルコーティング、スクリーン印刷ステンシルを製造するための、ステレオリソグラフィーにより三次元物体を製造するための、そして、画像記録材、フォトレジスト組成物、脱色材、画像記録材及びマイクロカプセルを用いた画像記録材の脱色材としての、請求項8に記載の方法。
- 請求項1に定義する式(I)の光開始剤化合物又は請求項14に定義する式(I”)の光開始剤化合物の、少なくとも1個のエチレン性不飽和二重結合を含むモノマー、オリゴマー又はポリマー化合物の光重合のための使用。
- 請求項1から請求項7のいずれか1項に記載の光重合性重合性組成物の、着色及び無着色塗料及びワニス、パウダーコーティング、印刷用インク、例えばスクリーン印刷用インク、オフセット、フレキソ又はインクジェット印刷用のインク、印刷版、接着剤、シーリング、注型材、歯科用組成物、フォーム、成形用化合物、複合材組成物、グラスファイバーケーブルコーティング、スクリーン印刷ステンシルを製造するための、ステレオリソグラフィーにより三次元物体を製造するための、そして、画像記録材、フォトレジスト組成物、脱色材、画像記録材及びマイクロカプセルを用いた画像記録材の脱色材としての、使用。
- 少なくとも1面が、請求項1から請求項7のいずれか1項に記載の組成物でコーティングされた、コーティングされた基材。
- 請求項1から請求項7のいずれか1項に記載の重合性組成物を硬化させることによって得られる、重合又は架橋組成物。
- 式(I”)の化合物:
Xは、O、S、直接結合又はCR16R17であり;
Yは、O又はSであり;
R1、R2、R3、R4、R5、R6、R7及びR8は、互いに独立に、水素、ハロゲン、C1−C4アルキル、C5−C7シクロアルキル、フェニル、C1−C4アルコキシ、C5−C7シクロアルコキシ、フェノキシ、C1−C4アルキルチオ、C5−C7シクロアルキルチオ、フェニルチオ、ジ(C1−C4アルキル)アミノ、ジ(C5−C7シクロアルキル)アミノ、N−モルフォリニル、N−ピペリジニル又は式(II)の基であり;
R11は、水素、C1−C4アルキル、C5−C7シクロアルキル、2−テトラヒドロピラニル又はSi(C1−C4アルキル)3である。 - 下記による式(I”)の化合物の製造方法:
1. 多環式アリール化合物
但し、R1、R2、R3、R4、R5、R6、R7及びR8の少なくとも1個が水素であり;
X及びYは、請求項14に定義する通りである。)の、
ハロゲン化物(IIa)又は酸無水物(IVa)
Halは、ハロゲン化物、好ましくは塩化物である。)によるFriedel−Craftsアシル化;
2. 続いて、得られるFriedel−Crafts付加物のハロゲン化、特にブロム化;
3. ハロゲン化中間体の加水分解により、請求項14に定義する式(I”)の対応するα−ヒドロキシケトン化合物を得る。
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JP2020507664A (ja) * | 2017-02-17 | 2020-03-12 | 常州強力先端電子材料有限公司Changzhou Tronly Advanced Electronic Materials Co.,Ltd. | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
JP7032416B2 (ja) | 2017-02-17 | 2022-03-08 | 常州強力先端電子材料有限公司 | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
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EP3189083B2 (en) | 2023-07-05 |
ES2798135T3 (es) | 2020-12-09 |
CN107075000B (zh) | 2020-01-31 |
US20170240755A1 (en) | 2017-08-24 |
EP3189083A4 (en) | 2018-04-18 |
JP6449445B2 (ja) | 2019-01-09 |
ES2798135T5 (es) | 2023-11-16 |
EP3189083A1 (en) | 2017-07-12 |
CN107075000A (zh) | 2017-08-18 |
EP3189083B1 (en) | 2020-04-08 |
WO2016034963A1 (en) | 2016-03-10 |
US10113075B2 (en) | 2018-10-30 |
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