JPH0426687A - Thioxanthone-based compound and photosensitive composition - Google Patents
Thioxanthone-based compound and photosensitive compositionInfo
- Publication number
- JPH0426687A JPH0426687A JP13278890A JP13278890A JPH0426687A JP H0426687 A JPH0426687 A JP H0426687A JP 13278890 A JP13278890 A JP 13278890A JP 13278890 A JP13278890 A JP 13278890A JP H0426687 A JPH0426687 A JP H0426687A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- compound
- groups
- photosensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 title abstract description 22
- -1 nitro, amino Chemical group 0.000 claims abstract description 35
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 239000012948 isocyanate Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- ANHLDZMOXDYFMQ-UHFFFAOYSA-N 2-hydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC=C3SC2=C1 ANHLDZMOXDYFMQ-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002513 isocyanates Chemical class 0.000 abstract description 5
- 239000000853 adhesive Substances 0.000 abstract description 4
- 230000001070 adhesive effect Effects 0.000 abstract description 4
- 238000007639 printing Methods 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 238000003848 UV Light-Curing Methods 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
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- 229910052742 iron Inorganic materials 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 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
- 239000012965 benzophenone Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KASSAJQZMXAYQT-UHFFFAOYSA-N 1,2-dihydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3SC2=C1 KASSAJQZMXAYQT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ROPLCNKLLVUPHM-UHFFFAOYSA-N 1,4-dihydroxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O ROPLCNKLLVUPHM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- UIQYTEPBXAMKEO-UHFFFAOYSA-N 2,4-dihydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC(O)=C3SC2=C1 UIQYTEPBXAMKEO-UHFFFAOYSA-N 0.000 description 1
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- URCLHZFMMKQMDR-UHFFFAOYSA-N 2-hydroxy-3,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(O)=C(C)C(C)=C3SC2=C1 URCLHZFMMKQMDR-UHFFFAOYSA-N 0.000 description 1
- IPSXHZSTGGEFGR-UHFFFAOYSA-N 2-hydroxy-3-methylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(O)=C2 IPSXHZSTGGEFGR-UHFFFAOYSA-N 0.000 description 1
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 1
- NXTOCVYXABBSGX-UHFFFAOYSA-N 3-methyloctan-4-one Chemical compound CCCCC(=O)C(C)CC NXTOCVYXABBSGX-UHFFFAOYSA-N 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000005907 alkyl ester group Chemical group 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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- 210000003298 dental enamel Anatomy 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ACYQDCZIQOLHRX-UHFFFAOYSA-M dodecanoate;trimethylstannanylium Chemical compound CCCCCCCCCCCC(=O)O[Sn](C)(C)C ACYQDCZIQOLHRX-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 239000004210 ether based solvent Substances 0.000 description 1
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- WKRKXDRSJVDMGO-UHFFFAOYSA-N ethyl 2-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(CC)CC WKRKXDRSJVDMGO-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride 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
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 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
- 239000005028 tinplate Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、感光性平版印刷版、感光性塗料、Ｕｖ硬化型
接着剤等の感光性組成物として有用なチオキサントン系
化合物、及び感光性組成物に関する。Detailed Description of the Invention "Field of Industrial Application" The present invention relates to thioxanthone compounds useful as photosensitive compositions such as photosensitive lithographic printing plates, photosensitive paints, and UV-curable adhesives, and photosensitive compositions. relating to things.
従来、感光性組成物としては、不飽和（メタ）アクリレ
ート系樹脂と光重合開始剤を組み合わせたものが一般的
である。Conventionally, photosensitive compositions that are a combination of an unsaturated (meth)acrylate resin and a photopolymerization initiator have generally been used.
［発明が解決しようとする課題］
しかしながら、従来の不飽和（メタ）アクリレート系樹
脂と光重合開始剤を組み合わせた感光性組成物は、感度
が十分でない、相溶性が悪いため経時変化を起こし易く
保存安定性が悪い、光重合開始剤により、感光性組成物
中に不要な着色が生じる、樹脂の劣化を引き起こす等の
問題点かあった。[Problems to be Solved by the Invention] However, conventional photosensitive compositions that combine unsaturated (meth)acrylate resins and photopolymerization initiators tend to change over time due to insufficient sensitivity and poor compatibility. There were problems such as poor storage stability, unnecessary coloring in the photosensitive composition due to the photopolymerization initiator, and deterioration of the resin.
［課題を解決するための手段］
本発明者らは、上記の問題点を解決すべく鋭意検討した
結果、感光性組成物に有用な化合物を見いだし、本発明
に到達した。[Means for Solving the Problems] As a result of intensive studies to solve the above-mentioned problems, the present inventors found a compound useful for photosensitive compositions and arrived at the present invention.
すなわち、
本発明は
一般式（１）
（式中Ｒは、水素原子またはメチル基；Ａは炭素数１〜
７のアルキレン基；Ｙ、Ｙ’は炭素数ｌ〜Ｂのアルキル
基、炭素数１〜Ｂのアルコキシ基、炭素数１〜Ｂのアル
キルチオ基、ハロゲノ基、ニトロ基、アミノ基、炭素数
１〜６のアルキル−アミノ基、炭素数１〜Ｂのヒドロキ
シアルキル−アミノ基、炭素数１〜Ｇのアルカノイルア
ミノ基、スルホンアミド基またはアセチル基；ｎは１〜
４の整数；１Ｉｈｑは０〜３の整数である。）で示され
るチオキサントン系化合物；及び一般式（１）で示され
るチオキサントン系化合物を含有してなる事を特徴とす
る感光性組成物である。That is, the present invention relates to the general formula (1) (wherein R is a hydrogen atom or a methyl group; A has 1 to 1 carbon atoms)
7 alkylene group; Y and Y' are an alkyl group having 1 to B carbon atoms, an alkoxy group having 1 to B carbon atoms, an alkylthio group having 1 to B carbon atoms, a halogeno group, a nitro group, an amino group, and an alkyl group having 1 to B carbon atoms; 6 alkyl-amino group, hydroxyalkyl-amino group having 1 to B carbon atoms, alkanoylamino group having 1 to G carbon atoms, sulfonamide group or acetyl group; n is 1 to
An integer of 4; 1Ihq is an integer of 0 to 3. ); and a thioxanthone compound represented by general formula (1).
一般式（１）において、Ａの炭素数１〜７のアルキレン
基としては、例えばメチレン基、エチレン基、プロピレ
ン基、ブチレン基、ペンタメチレン基、ヘキサノ、チレ
ン基、ヘプタメチレン基などが挙げられるが、好ましく
はエチレン基、プロピレン基、及びブチレン基である。In general formula (1), examples of the alkylene group having 1 to 7 carbon atoms in A include methylene group, ethylene group, propylene group, butylene group, pentamethylene group, hexano, tylene group, heptamethylene group, etc. , preferably ethylene group, propylene group, and butylene group.
ＹおよびＹ′としては、炭素数１〜６のアルキル基、炭
素数１〜６のアルコキシ基、炭素数１〜６のアルキルチ
オ基、ハロゲノ基、ニトロ基、アミ７基、炭素数１〜６
のアルキル−アミノ基、炭素数ｌ〜６のヒドロキシアル
キル−アミノ基、炭素数１〜６のアルカノイルアミノ基
、スルホンアミド基、またはアセチル基が挙げられる。Y and Y' include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, a halogeno group, a nitro group, an amine 7 group, and 1 to 6 carbon atoms.
Examples include an alkyl-amino group having 1 to 6 carbon atoms, a hydroxyalkyl-amino group having 1 to 6 carbon atoms, an alkanoylamino group having 1 to 6 carbon atoms, a sulfonamide group, or an acetyl group.
これらの具体例としては炭素数１〜６のアルキル基とし
て、例えばメチル基、エチル基、プロピル基、ブチル基
、イソプロピル基、ヘキシル基など；炭素数１〜Ｂのア
ルコキシ基として、例えばメトキシ基、エトキシ基、ペ
ンタオキシ基、ヘキサオキシ基など；炭素数１〜６のア
ルキルチオ基として、例えばメチルチオ基、プロピルチ
オ基、ｔ−ブチルチオ基、ヘキシルチオ基など；ハロゲ
ン基として、例えば塩素、臭素、ヨウ素など；炭素数１
〜６のアルキル−アミノ基として、例えばＮ−エチル−
アミノ基、トプロピルーアミノ基、Ｎ−ヘキシル−アミ
ノ基、Ｎ、Ｎ−ジエチル−アミノ基、Ｎ、Ｎ−ジペンチ
ルーアミノ基など；炭素数１−８のヒドロキシアルキル
−アミノ基として、例えばヒドロキシプロピル−アミノ
基、ヒドロキシペンチル−アミノ基など；炭素数１−８
のアルカノイルアミノ基として、例えばアセチルアミノ
基、ヘキサノイルアミノ基など； スルホンアミド基と
して、例えばメチルスルホンアミド基、ヘキサスルホン
アミド基などが挙げられる。Specific examples of these include alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, isopropyl, and hexyl; alkoxy groups having 1 to B, such as methoxy, Ethoxy group, pentaoxy group, hexaoxy group, etc.; Alkylthio group with 1 to 6 carbon atoms, such as methylthio group, propylthio group, t-butylthio group, hexylthio group, etc.; Halogen group, such as chlorine, bromine, iodine, etc.; number of carbon atoms 1
~6 alkyl-amino groups, for example N-ethyl-
Amino group, topropylamino group, N-hexyl-amino group, N,N-diethyl-amino group, N,N-dipentylamino group, etc.; as a hydroxyalkyl-amino group having 1-8 carbon atoms, for example Hydroxypropyl-amino group, hydroxypentyl-amino group, etc.; carbon number 1-8
Examples of the alkanoylamino group include an acetylamino group and a hexanoylamino group; examples of the sulfonamide group include a methylsulfonamide group and a hexasulfonamide group.
一般式（１）で示されるチオキサン
トン系化合物は、
一般式（２）０
％式％（２）
（式中Ｒ及びＡは一般式（１）で示したものと同一であ
る。）で示されるイソシアネート化合物と、形式（３）
（式中Ｙ、Ｙ″及びｎ、ｌＩｌ、ｑは一般式（１）で示
したものと同一である。）で示されるヒドロキシチオキ
サントン化合物とを、従来公知のウレタン化反応させる
ことによって製造することができる。The thioxanthone compound represented by the general formula (1) is represented by the general formula (2) (in the formula, R and A are the same as those shown in the general formula (1)). The isocyanate compound and the hydroxythioxanthone compound represented by the formula (3) (wherein Y, Y″, n, lIl, and q are the same as those shown in the general formula (1)) are combined into a conventionally known urethane compound. It can be produced by chemical reaction.
一般式（２）で示される化合物としては、 （メタ）ア
クリロイルオキシメチルイソシアネート、 （メタ）ア
クリロイルオキシエチルイソシアネート、（メタ）アク
リロイルオキシプロピルイソシアネート、 （メタ）ア
クリロイルオキシブチルイソシアネート等が挙げられる
。Examples of the compound represented by the general formula (2) include (meth)acryloyloxymethyl isocyanate, (meth)acryloyloxyethyl isocyanate, (meth)acryloyloxypropyl isocyanate, (meth)acryloyloxybutyl isocyanate, and the like.
一般式（３）で示されるヒドロキシチオキサントン化合
物としては、２−ヒドロキシチオキサントン。The hydroxythioxanthone compound represented by the general formula (3) is 2-hydroxythioxanthone.
２−ヒドロキシ−３−メチルチオキサントン、２−ヒド
ロキシ−３−メトキシチオキサントン、２−ヒドロキシ
−３−クロロ−チオキサントン、２−ヒドロキシ−３，
４−ジクロロ−チオキサントン、２−ヒドロキシ−３，
４−ジメチルチオキサントン、ｌ、４ジヒドロキシチオ
キサントン、２，４−ジヒドロキシチオキサントン、２
．４−ジヒドロキシ−３−アセチルチオキサントン、２
，４−ジヒドロキシ−７−シメチルアミノーチオキサン
トン、２゜３．４−トリヒドロキシチオキサントン、
２，３．４− ）リヒドロキシー７−メチルチオキサ
ントン等が挙げられる。これらは、例えばＥＰ−Ａ （
欧州特許）第８１２８０号、ＤＥ−Ａ （西ドイツ国特
許）第２５０４１ｉ４２号、チェコスロバキア国特許第
１４５０１１１ｉ号等に記載の合成法により合成する事
ができる。2-hydroxy-3-methylthioxanthone, 2-hydroxy-3-methoxythioxanthone, 2-hydroxy-3-chloro-thioxanthone, 2-hydroxy-3,
4-dichloro-thioxanthone, 2-hydroxy-3,
4-dimethylthioxanthone, l, 4 dihydroxythioxanthone, 2,4-dihydroxythioxanthone, 2
．． 4-dihydroxy-3-acetylthioxanthone, 2
, 4-dihydroxy-7-dimethylaminothioxanthone, 2°3.4-trihydroxythioxanthone,
2,3.4-)rihydroxy-7-methylthioxanthone and the like. These are, for example, EP-A (
It can be synthesized by the synthesis method described in European Patent No. 81280, DE-A (West German Patent) No. 25041i42, Czechoslovakia Patent No. 1450111i, etc.
一般式（２）で示されるイソシアネート化合物と一般式
（３）で示されるヒドロキシチオキサントン化合物との
ウレタン化反応において、イソシアネート基（Ｎｅｏ基
）とヒドロキシル基（Ｏｌ（基）の割合は、ＮＣＯ基：
ＯＨ基＝１：Ｉ〜１：１０ （モル比）好ましくは！：
ｌ〜１：５である。In the urethanation reaction between the isocyanate compound represented by general formula (2) and the hydroxythioxanthone compound represented by general formula (3), the ratio of isocyanate groups (Neo groups) to hydroxyl groups (Ol (groups) is NCO groups:
OH group = 1:I to 1:10 (mole ratio) preferably! :
l~1:5.
ウレタン化反応は、イソシアネート基に対して不活性な
溶媒の存在下、または非存在下で行うことができる。溶
媒の存在下で行う場合の適当な溶媒としては、アミド系
溶媒（ジメチルホルムアミド、ジメチルアセトアミド等
）、スルホキシド系溶媒（ジメチルスルホキシド等）、
エーテル系溶媒（ジオキサン、テトラヒドロフラン等）
、ケトン系溶媒（シクロヘキサノン、メチルエチルケト
ン等）、エステル系溶媒（酢酸エチル等）、芳香族炭化
水素溶媒（トルエン等）及びこれらの二種以上の混合溶
媒が挙げられる。The urethanization reaction can be carried out in the presence or absence of a solvent inert to isocyanate groups. Suitable solvents when carrying out in the presence of a solvent include amide solvents (dimethylformamide, dimethylacetamide, etc.), sulfoxide solvents (dimethylsulfoxide, etc.),
Ether solvents (dioxane, tetrahydrofuran, etc.)
, ketone solvents (cyclohexanone, methyl ethyl ketone, etc.), ester solvents (ethyl acetate, etc.), aromatic hydrocarbon solvents (toluene, etc.), and mixed solvents of two or more of these solvents.
反応を促進させるため、必要に応じてウレタン化反応に
於て従来公知のアミン系触媒（トリエチルアミン、Ｎ−
エチルモルホリン、 トリエチレンジアミン等）、錫系
触媒（トリメチルチンラウレート、ジブチルチンジラウ
レート等）を使用してもよい。更に重合禁止剤として、
例えばハイドロキノン、ハイドロキノンモノエチルエー
テル、 ｔ−ブチルカテコール、ピロガロールまたはフ
ェノチアジン等）を使用することができる。In order to accelerate the reaction, conventionally known amine catalysts (triethylamine, N-
Ethylmorpholine, triethylenediamine, etc.), tin-based catalysts (trimethyltin laurate, dibutyltin dilaurate, etc.) may also be used. Furthermore, as a polymerization inhibitor,
For example, hydroquinone, hydroquinone monoethyl ether, t-butylcatechol, pyrogallol or phenothiazine) can be used.
反応温度は、通常０〜２００℃であり、好ましくは２０
−１５０°Ｃである。反応温度が０℃未満では反応収率
が低くなり、２００℃を越えるとビニル基の熱重合が起
こり易くなる。また、反応時間は通常１〜４０時間、好
ましくは２〜２０時間である。The reaction temperature is usually 0 to 200°C, preferably 20°C.
-150°C. If the reaction temperature is less than 0°C, the reaction yield will be low, and if it exceeds 200°C, thermal polymerization of vinyl groups will easily occur. Further, the reaction time is usually 1 to 40 hours, preferably 2 to 20 hours.
反応の追跡は、系内に残存するフリーのイソシアネート
を定量する事により行うことができる。The reaction can be monitored by quantifying the amount of free isocyanate remaining in the system.
イソシアネート基の定量は従来公知の方法、すなわちＩ
Ｒ等の機器分析または滴定等の化学分析により行うこと
ができる。The isocyanate groups can be quantified using a conventionally known method, namely I
This can be carried out by instrumental analysis such as R or chemical analysis such as titration.
反応が終了すれば、目的化合物を溶媒抽出法、蒸留法、
再結晶法等の分離手段によって得ることができる。Once the reaction is complete, the target compound can be extracted by solvent extraction, distillation,
It can be obtained by separation means such as recrystallization.
尚、本発明の感光性組成物には、必要に応じて、感度を
更に向上させる目的や、可視光領域への光感度をもたせ
る目的で、光開始剤や増感剤を併用することもできる。In addition, a photoinitiator or a sensitizer may be used in the photosensitive composition of the present invention, if necessary, for the purpose of further improving the sensitivity or imparting photosensitivity to the visible light region. .
併用する光開始剤、増感剤としては、この分野で従来公
知のものは制限なく使用することが可能であり、例えば
、フォトポリマーハンドブック（工業調査会編）、感光
性高分子（講談社）、光機能性高分子の合成と応用（Ｃ
ＭＣ）、Ｊ、Ｐｈｏｔｏｐｏｌｙｍ、Ｓｃ１．Ｔｅｃｈ
、Ｖｏｌ 、２．Ｐ、２７９（１９８９）に記載のもの
が挙げら、れ、光開始剤としては、例えばベンゾフェノ
ン、ベンゾインエチルエーテル剤としては、例えば、チ
オキサンチン系色素、クマリン色素、メロシアニン色素
が挙げられる。As the photoinitiator and sensitizer used in combination, those conventionally known in this field can be used without restriction, such as Photopolymer Handbook (edited by Industrial Research Association), Photosensitive Polymer (Kodansha), Synthesis and application of photofunctional polymers (C
MC), J. Photopolym, Sc1. Tech
, Vol. 2. Examples of the photoinitiator include benzophenone, and examples of the benzoin ethyl ether agent include thioxanthin dyes, coumarin dyes, and merocyanine dyes.
また、本発明の感光性組成物には、使用目的に併せて、
更に公知のバインダー 着色剤、Ｕｖ吸収剤、熱重合防
止剤等を必要に応じて含有させることができる。In addition, the photosensitive composition of the present invention includes, in accordance with the purpose of use,
Furthermore, known binders, colorants, UV absorbers, thermal polymerization inhibitors, etc. can be included as necessary.
バインダーとしては、有機高分子重合体であれば、特に
限定されないが、この様な有機高分子重合体としては、
ポリ（メタ）アクリル酸アルキルエステル（ポリメチル
アクリレート、ポリエチルアクリレート、ポリメチルメ
タクリレート、ポリエチルメタクリエート等）、不飽和
カルボン酸共重合体（アクリル酸共重合体、メタクリル
酸共重合体、マレイン酸共重合体等）、ポリハロゲン含
有ビニル炭化水素（共）重合体（塩素化ポリエチレン、
塩素化ポリプロピレン、ポリ塩化ビニル等）、ニトリル
含をビニル炭化水素（共）重合体（ポリアクリロニトリ
ル等）、脂肪族または芳香族炭化水素（共）重合体（ポ
リエチレン、ポリプロピレンポリスチレン等）、ポリア
ルキルエーテルポリビニルアルコール、ポリアミド、ポ
リウレタン、塩素化ゴム、セルロース誘導体、ポリビニ
ルピロリドン等が挙げられる。また、バインダーとして
はワックス類を用いても構わない。これらは−ｌ〇−
二種以上の混合物としても使用できる。The binder is not particularly limited as long as it is an organic polymer, but such organic polymers include:
Poly(meth)acrylic acid alkyl esters (polymethyl acrylate, polyethyl acrylate, polymethyl methacrylate, polyethyl methacrylate, etc.), unsaturated carboxylic acid copolymers (acrylic acid copolymers, methacrylic acid copolymers, maleic acid) copolymers, etc.), polyhalogen-containing vinyl hydrocarbon (co)polymers (chlorinated polyethylene,
chlorinated polypropylene, polyvinyl chloride, etc.), nitrile-containing vinyl hydrocarbon (co)polymers (polyacrylonitrile, etc.), aliphatic or aromatic hydrocarbon (co)polymers (polyethylene, polypropylene polystyrene, etc.), polyalkyl ethers Examples include polyvinyl alcohol, polyamide, polyurethane, chlorinated rubber, cellulose derivatives, polyvinylpyrrolidone, and the like. Further, waxes may be used as the binder. -10- These can also be used as a mixture of two or more types.
着色剤としては、光学的に認識できる画像等を形成する
のに含有させる成分であり、各種顔料、染料が適時用い
られる。この様な顔料、染料の例としては、無機顔料（
カーボンブラック、黄鉛、モリブデンレッド、ベンガラ
等）、有機顔料（ハンザイイエロー ベンジンイエロー
ブリリアントカーミン８Ｂ、 レークレッドＦ ５
Ｒ，フタロシアニンブルー ビクトリアブルーレーク、
ファストスカイブルー等）アゾ染料、アントラキノン染
料、ロイコ染料、フタロシアニン染料等の着色剤等が挙
げられる。The coloring agent is a component to be included to form an optically recognizable image, and various pigments and dyes are used as appropriate. Examples of such pigments and dyes include inorganic pigments (
carbon black, yellow lead, molybdenum red, red iron, etc.), organic pigments (Hanzai Yellow, Benzine Yellow, Brilliant Carmine 8B, Lake Red F 5)
R, Phthalocyanine Blue Victoria Blue Lake,
Examples include coloring agents such as azo dyes, anthraquinone dyes, leuco dyes, and phthalocyanine dyes (fast sky blue, etc.).
■ｖ吸収剤としては、ベンゾフェノン系、サリシレート
系、ベンゾトリアゾール系、蓚酸アニリド系の化合物等
が挙げられる。(2) Examples of the v-absorbent include benzophenone-based, salicylate-based, benzotriazole-based, and oxalic acid anilide-based compounds.
可塑剤としては、フタル酸エステル類（ジエチルフタレ
ート、ジメチルフタレート等）、グリコールエステル類
（エチルフタルエチレングリコール等）、燐酸エステル
類（トリフェニルフォスフェート等）、脂肪酸二塩基酸
エステル類（ジオクチルアジペート、ジオクチルアゼレ
ート、ジブチルマレエート等）等が挙げられる。Examples of plasticizers include phthalate esters (diethyl phthalate, dimethyl phthalate, etc.), glycol esters (ethylphthalethylene glycol, etc.), phosphoric esters (triphenyl phosphate, etc.), and fatty acid dibasic acid esters (dioctyl adipate, etc.). dioctyl azelate, dibutyl maleate, etc.).
熱重合防止剤としては、ｐ−メトキシフェノールヒドロ
キノン、ｔ−ブチルカテコール、２，６−ジーｔ−ブチ
ル−ｐ−クレゾール、塩化第一銅、宵機酸銅等が挙げら
れる。Examples of the thermal polymerization inhibitor include p-methoxyphenolhydroquinone, t-butylcatechol, 2,6-di-t-butyl-p-cresol, cuprous chloride, and copper chloride.
本発明の感光性組成物は、これら各種構成成分を均一に
混合させて使用するのが一般的であり、この方法として
は特に限定されないが、有機溶剤等に溶解もしくは分散
させて使用するのが好ましい。これらの有機溶剤として
は、各成分と相溶するものなら特に限定されないが、例
えば、塩素化炭化水素類（塩化メチレン、クロロホルム
、エチレンジクロライド等）、ケトン類（アセトン、メ
チルエチルケトン、メチルエチルヘキサノン等）、アミ
ド類（ジメチルホルムアミド、ジメチルアセトアミド等
）、アルコール類（メタノール、エタノール、プロパツ
ール等）、ケトンアルコール類（ジアセトンアルコール
等）エステル類（酢酸エチル等）等及びこれらの二種以
上の混合物が挙げられる。The photosensitive composition of the present invention is generally used by uniformly mixing these various components, and although this method is not particularly limited, it is preferable to use it by dissolving or dispersing it in an organic solvent etc. preferable. These organic solvents are not particularly limited as long as they are compatible with each component, but examples include chlorinated hydrocarbons (methylene chloride, chloroform, ethylene dichloride, etc.), ketones (acetone, methyl ethyl ketone, methyl ethyl hexanone, etc.) , amides (dimethylformamide, dimethylacetamide, etc.), alcohols (methanol, ethanol, propatool, etc.), ketone alcohols (diacetone alcohol, etc.), esters (ethyl acetate, etc.), and mixtures of two or more of these. Can be mentioned.
本発明の感光性組成物の使用法としては、種々の無機物
（鉄、アルミニウム、銅、合金、ブリキ、トタン等の金
属類；瓦、スレート、タイル、ホウロウ、セメント、レ
ンガ、ガラス等の窯業製品等）及び、有機物（プラスチ
ック、繊維製品、木材、皮革等）等の成形部材の様な基
体上に適用して使用するのが一般的である。The photosensitive composition of the present invention can be used in various inorganic materials (metals such as iron, aluminum, copper, alloys, tinplate, and galvanized iron; ceramic products such as roof tiles, slate, tiles, enamel, cement, bricks, and glass). etc.) and organic materials (plastics, textile products, wood, leather, etc.) and molded parts.
適用方法としては、スプレー スピンコーターヘラ等で
塗布する方法、及び浸漬する方法が挙げられる。Application methods include a method of applying with a spray, spin coater spatula, etc., and a method of dipping.
上述の方法により得られた本発明の感光性組成物を硬化
させる方法としては、当分野で一般的に使用されている
光照射装置による方法が一般的である。これらの照射光
源としては、例えば、低圧水銀灯、中圧水銀灯、高圧水
銀灯、超高圧水銀灯、キセノンランプ、メタルハロゲン
ランプ、電子線照射装置、Ｘ線照射装置、レーザー（ア
ルゴンレーザ、色素レーザー 窒素レーザー ヘリウム
カドミウムレーザー等）等がある。As a method for curing the photosensitive composition of the present invention obtained by the above-mentioned method, a method using a light irradiation device commonly used in this field is generally used. These irradiation light sources include, for example, low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, metal halogen lamps, electron beam irradiation equipment, X-ray irradiation equipment, lasers (argon laser, dye laser, nitrogen laser, helium cadmium laser, etc.).
［実施例コ
以下、実施例により本発明を更に説明するが、本発明は
これに限定されるものではない。以下において、部及び
％はそれぞれ重量部、重量％を示す。[Example] Hereinafter, the present invention will be further explained with reference to Examples, but the present invention is not limited thereto. In the following, parts and % indicate parts by weight and % by weight, respectively.
合成例１
温度計、冷却管、攪拌装置を備えた１００ｍ１の三ロフ
ラスコに、２−ヒドロキシチオキサントン２．５ｇ（１
１，５＋ｍｍｏｌ）とジメチルホルムアミド］Ｏｍｌを
加え、攪拌しながらジブチルチンシラウリレート２，３
滴、２−インシアネートエチルメタクリレ−） １．８
ｇ（１１，５ｍｍｏ ＋ ）を加えた。反応溶液は、６
５℃で加熱し４時間攪拌した。反応後、２００ＩＩ＋の
ヘキサンに反応物を添加し、析出した固体を濾過した。Synthesis Example 1 2.5 g of 2-hydroxythioxanthone (1
1,5+mmol) and dimethylformamide] and dibutyltinsilaurylate 2,3 while stirring.
drops, 2-incyanate ethyl methacrylate) 1.8
g (11,5 mmo + ) was added. The reaction solution was 6
The mixture was heated at 5°C and stirred for 4 hours. After the reaction, the reactant was added to 200II+ hexane, and the precipitated solid was filtered.
乾燥後、 トルエンより再結晶して上記の本発明の化合
物２．８ｇ（収率６７％）を得た。この化合物は、下記
物性を有する。After drying, it was recrystallized from toluene to obtain 2.8 g (yield: 67%) of the above compound of the present invention. This compound has the following physical properties.
融点：１３２〜１３４℃
’ Ｈ−ＮＭＲ（ＤＭＳＯ−ｄｓ） ： δ（ｐｐｍ
）＝１．８９（３Ｈ，ｓ、ＣＨ３）、３．４０（２Ｈ＋
ｍ ｒ ＮＣＨ２） ＋ ４−１９ （２Ｈｒ Ｉｌ
ｌ ＋ ＯＣＨａ ） ＋ ５．７０ （Ｉ Ｈ＋ Ｓ
＋ ”ＣＨ２）。Melting point: 132-134°C' H-NMR (DMSO-ds): δ (ppm
) = 1.89 (3H, s, CH3), 3.40 (2H+
m r NCH2) + 4-19 (2Hr Il
l + OCHa ) + 5.70 (I H + S
+”CH2).
８．１０（Ｉｎ、ｓ、＝Ｃ［１２）、８．０５（７■ｌ
ｆｆ１ＩＡｒ１（）１８．１５（Ｉｌｌｌｍ、ＮＨ）Ｉ
Ｒ（ａｍ−’ ）：２４５０．＋７３０．１８３０．＋
５９０．１５２０．１４７０゜＋３０９．１２５０．１
２２０．１＋２０，９５０，８３０，７８０，１ｌｉ４
０合成例２
合成例１の２−ヒドロキシチオキサントン２．５ｇのか
わりに２−ヒドロキシ−７−メチルチオキサントンを用
い、他は合成例１と同様の方法により、以下に示す本発
明の化合物を合成した。この化合物は下記物性を有する
。8.10 (In, s, = C[12), 8.05 (7■l
ff1IAr1()18.15(Illm,NH)I
R(am-'): 2450. +730.1830. +
590.1520.1470°+309.1250.1
220.1+20,950,830,780,1li4
0 Synthesis Example 2 The following compound of the present invention was synthesized in the same manner as in Synthesis Example 1 except that 2-hydroxy-7-methylthioxanthone was used in place of 2.5 g of 2-hydroxythioxanthone in Synthesis Example 1. . This compound has the following physical properties.
融点： １［１１−１［ｉ９℃
’ Ｈ４ＭＲ（ＤＭＳＯ−ｄｏ） ： δ（ｐｐｍ）
＝１．８［１（３１１１８，ＣＨ３）、３．３７（２＋
？ 、ｉｔ、Ｎ（１！Ｉ？ｆ ）１２．４０（３Ｈ、ｓ
、ＣＨａ ） １ｃ１５（２１、ｌ ＋０ＣＨａ ）
、５．７２（Ｉｎ ＋８ ＋”ＣＨａ ） １８．１２
（Ｉｎ ＋Ｓ ｌ”ｃＨ２） ＋８．０９（ＧＷ Ｈ
ｍ 、Ａｒ ［１＞、８．１８（ＩＪｍ、Ｎｕ）
ＩＲ（ｃｍ−’）：２４４５，１７４０．１Ｂ４０，１
５８５，１５２５，１４７０゜１３０５．１２［ｉｏ、
１２２０，１１１５，９５４，８３５，７１１ｉ０．８
４３合成例３
合成例１の２−ヒドロキシチオキサントン２．５ｇのか
わりに１．４−ジヒドロキシチオキサントン２．５ｇを
用い、他は合成例１と同様の方法により、以下に示す本
発明の化合物を合成した。この化合物は下記物性を有す
る。Melting point: 1[11-1[i9℃' H4MR (DMSO-do): δ (ppm)
=1.8[1(31118,CH3), 3.37(2+
? ,it,N(1!I?f)12.40(3H,s
, CHa ) 1c15 (21, l +0CHa )
, 5.72 (In +8 +”CHa ) 18.12
(In +S l”cH2) +8.09(GW H
m, Ar [1>, 8.18 (IJm, Nu) IR (cm-'): 2445,1740.1B40,1
585,1525,1470°1305.12[io,
1220,1115,954,835,711i0.8
43 Synthesis Example 3 The following compound of the present invention was synthesized in the same manner as in Synthesis Example 1 except that 2.5 g of 1,4-dihydroxythioxanthone was used in place of 2.5 g of 2-hydroxythioxanthone in Synthesis Example 1. did. This compound has the following physical properties.
融点二１２２〜１２５℃
’ Ｈ−ＮＭＲ（ＤＭＳＯ−ｄｏ） ： δ（＋）ｐ
ｍ）”１．８１（３１１４，ＣＨ３）、１．９０（３Ｈ
、ｓ、ＣＨａ ）、３．４３（２Ｈ，ｍ 、ＮＣＴｌ２
）、 ３．４８（２Ｈ、ｍ 、ＮＣＢａ ）１４．１
０（２■、ｍ 、０ＣＦ１ｐ ）、４．１７ （２Ｈ、
ｍ 、０ＣＨ２） 、５．８７（Ｉｎ 、ｓ 、＝ＣＨ
２）、ｅ 、１５（ＩＭ 、Ｓ ＋”ＣＨ２Ｌ５．７２
（ＩＨ、Ｓ １＝ｃＨａ ） 、Ｅｉ、２５（ＩＩＴ
、Ｓ、：ＣＨ２）、８．１２（６１，ｍ、ＡｒＨ） 、
８．ＩＥｉ（１Ｂ、＋ｎＪＨ）、８．１９（１■。Melting point 2122-125℃' H-NMR (DMSO-do): δ(+)p
m)”1.81 (3114, CH3), 1.90 (3H
, s, CHa ), 3.43 (2H, m , NCTl2
), 3.48 (2H, m, NCBa) 14.1
0 (2■, m, 0CF1p), 4.17 (2H,
m ,0CH2) ,5.87(In ,s ,=CH
2), e, 15 (IM, S +”CH2L5.72
(IH, S 1=cHa ), Ei, 25 (IIT
,S,:CH2),8.12(61,m,ArH),
8. IEi (1B, +nJH), 8.19 (1■.
ＩＢ−
ｍ、ＮＨ）
ＩＲ（ｃｍ−’ ）：２４８θ、１７２０．ＩＧ、＋５
．１５８５．１５１Ｇ、１４８５゜１３１５．１２４０
，１２３５．１１１５，９８５，８４０，７５５，６４
０実施例！
エチレン性不飽和二重結合を有する化合物として、合成
例１の方法により合成した本発明の化合物ｔｌ−１５部
、バインダーとしてポリメチルメタクリレートを１０部
、アミンとしてエチルジエチルアミノベンゾエートを０
．８部、着色剤として日本化薬社製カヤセットブルー１
３［ｉを０．１部、以上のものをジクｏ Ｏ、）’ ｌ
：／ ＦＪ２００ｍＩに溶解し、スピナーを用いテア
ルミニウム板上に塗布、これを［ｉｏ”Ｃ１Ｉｎ分間乾
燥させて、厚さ約５μｍの感光層とした。IB-m, NH) IR (cm-'): 248θ, 1720. IG, +5
．． 1585.151G, 1485°1315.1240
,1235.1115,985,840,755,64
0 examples! As a compound having an ethylenically unsaturated double bond, 15 parts of the compound of the present invention synthesized by the method of Synthesis Example 1, 10 parts of polymethyl methacrylate as a binder, and 0 parts of ethyl diethylaminobenzoate as an amine.
．． 8 parts, Kayaset Blue 1 manufactured by Nippon Kayaku Co., Ltd. as a coloring agent
3 [0.1 part of i, more than 0.0 parts, )' l
:/ The solution was dissolved in 200 mI of FJ and applied onto a aluminum plate using a spinner, and this was dried for [io''C1In] to form a photosensitive layer with a thickness of about 5 μm.
次に、前記感光層の上に酸素防止層としてＰＶＡ （ポ
リビニルアルコール）を３μｍの厚さで塗布し試料とし
た。この試料について下記の評価を行った。Next, PVA (polyvinyl alcohol) was applied as an oxygen prevention layer to a thickness of 3 μm on the photosensitive layer to prepare a sample. This sample was evaluated as follows.
（１）感度
試料上に光学楔（光学濃度０〜１０段）を置き、ｌ００
Ｗ高圧水銀灯で３０秒間露光した後、ＰＶＡを水洗除去
し、さらに感光層を１．１．１−トリクロロエタンで３
０秒間処理して現出した画像の対応する光学楔の最高段
数を試料の感度として表した。即ち、段数の高いものほ
ど高感度であることを示す。(1) Place an optical wedge (optical density 0 to 10 steps) on the sensitive sample and
After exposure for 30 seconds with a W high-pressure mercury lamp, the PVA was removed by washing with water, and the photosensitive layer was further diluted with 1.1.1-trichloroethane for 30 seconds.
The highest number of optical wedges corresponding to the image that appeared after processing for 0 seconds was expressed as the sensitivity of the sample. That is, the higher the number of stages, the higher the sensitivity.
（２）感光層保存テスト
試料を温度４０℃の条件下１２０時間保存し、感光層皮
膜の着色の有無、開始剤のブリードアウトの有無、安定
性（ゲル化物がないか）を目視で観察した。結果を表１
に示す。(2) Photosensitive layer storage test Samples were stored at a temperature of 40°C for 120 hours, and the presence or absence of coloring of the photosensitive layer film, presence or absence of initiator bleed-out, and stability (no gelling) were visually observed. . Table 1 shows the results.
Shown below.
実施例２，３
エチレン性不飽和二重結合を有する化合物として、合成
例２及び３で合成した化合物に替える以外は、実施例１
と同様の方法により評価を行った。結果を表１に示す。Examples 2 and 3 Example 1 except that the compounds synthesized in Synthesis Examples 2 and 3 were used as the compounds having ethylenically unsaturated double bonds.
Evaluation was performed using the same method as above. The results are shown in Table 1.
比較例１．２
エチレン性不飽和二重結合を存する化合物をして、合成
例１で示した化合物を、■、６−ヘキサンシオールジメ
タクリレート及びトリメチロールプロパントリメタクリ
レートにかえ、かつ光開始剤として２−クロロチオキサ
ン
トン１部を用いる以外は、
実施例Ｉと同様の方法により評価を行った。Comparative Example 1.2 Using a compound containing an ethylenically unsaturated double bond, the compound shown in Synthesis Example 1 was replaced with ■,6-hexanesiol dimethacrylate and trimethylolpropane trimethacrylate, and as a photoinitiator Evaluation was performed in the same manner as in Example I, except that 1 part of 2-chlorothioxanthone was used.
結果を 表１に併せて示す。results It is also shown in Table 1.
［発明の効果コ
上述のごとく、本発明の化合物は、分子内に光開始能を
存する骨格と、不飽和二重結合を有するため、基本的に
光開始剤がなくとも十分高感度で光硬化させることが可
能となり、この化合物単独でも感光性組成物を構成させ
ることができる。この為、こうして得られた感光性組成
物は、保存中に光開始剤のブリードアウトや経時変化が
生じず、保存安定性が飛躍的に向上する。更に、従来の
感光性組成物のように、樹脂中の光重合開始剤により、
感光性組成物の着色、樹脂の劣化を引き起こすこともな
い。[Effects of the Invention] As mentioned above, the compound of the present invention has a skeleton capable of photoinitiation and an unsaturated double bond in its molecule, so it can basically be photocured with sufficiently high sensitivity even without a photoinitiator. This makes it possible to form a photosensitive composition using this compound alone. Therefore, in the photosensitive composition thus obtained, the photoinitiator does not bleed out or change over time during storage, and its storage stability is dramatically improved. Furthermore, like conventional photosensitive compositions, due to the photopolymerization initiator in the resin,
It does not cause coloring of the photosensitive composition or deterioration of the resin.
このため、本発明の化合物を使用した感光性組成物は感
光性平板印刷版、感光性塗料、光硬化型接着剤、印刷イ
ンキ、タイルコーティング、光フアイバーコーティング
、積層接着剤、プラスチックフィルムコーチインク、電
線コーチインク、金属塗料、自動車部品及びエレクトロ
ニクス関連塗料、磁気テープバインダー 歯科用バイン
ダー等に好適に使用することが可能となる。Therefore, photosensitive compositions using the compounds of the present invention can be used for photosensitive lithographic printing plates, photosensitive paints, photocurable adhesives, printing inks, tile coatings, optical fiber coatings, lamination adhesives, plastic film coach inks, It can be suitably used for wire coach inks, metal paints, paints related to automobile parts and electronics, magnetic tape binders, dental binders, etc.
Claims (1)
） （式中Ｒは、水素原子またはメチル基；Ａは炭素数１〜
７のアルキレン基；Ｙ、Ｙ′は炭素数１〜６のアルキル
基、炭素数１〜６のアルコキシ基、炭素数１〜６のアル
キルチオ基、ハロゲノ基、ニトロ基、アミノ基、炭素数
１〜８のアルキル−アミノ基、炭素数１〜６のヒドロキ
シアルキル−アミノ基、炭素数１〜６のアルカノイルア
ミノ基、スルホンアミド基またはアセチル基；ｎは１〜
４の整数；ｍ、ｑは０〜３の整数である。）で示される
チオキサントン系化合物。 ２、請求項１記載のチオキサントン系化合物を含有して
なることを特徴とする感光性組成物。[Claims] 1. General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・(1
) (In the formula, R is a hydrogen atom or a methyl group; A has 1 to 1 carbon atoms.
7 alkylene group; Y and Y' are alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, alkylthio groups having 1 to 6 carbon atoms, halogeno groups, nitro groups, amino groups, and 1 to 6 carbon atoms; 8 alkyl-amino group, hydroxyalkyl-amino group having 1 to 6 carbon atoms, alkanoylamino group having 1 to 6 carbon atoms, sulfonamide group or acetyl group; n is 1 to
An integer of 4; m and q are integers of 0 to 3. ) Thioxanthone compounds. 2. A photosensitive composition comprising the thioxanthone compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13278890A JPH0426687A (en) | 1990-05-23 | 1990-05-23 | Thioxanthone-based compound and photosensitive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13278890A JPH0426687A (en) | 1990-05-23 | 1990-05-23 | Thioxanthone-based compound and photosensitive composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0426687A true JPH0426687A (en) | 1992-01-29 |
Family
ID=15089561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13278890A Pending JPH0426687A (en) | 1990-05-23 | 1990-05-23 | Thioxanthone-based compound and photosensitive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0426687A (en) |
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| JP2009184989A (en) * | 2008-02-08 | 2009-08-20 | Toyo Ink Mfg Co Ltd | Photopolymerization initiator, polymerizable composition and method for producing polymer |
| US8320424B2 (en) | 2005-12-01 | 2012-11-27 | Electro Scientific Industries, Inc. | Optical component cleanliness and debris management in laser micromachining applications |
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-
1990
- 1990-05-23 JP JP13278890A patent/JPH0426687A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6803168B1 (en) * | 1997-05-27 | 2004-10-12 | Clariant Finance (Bvi) Limited | Composition for anti-reflective coating or radiation absorbing coating and compounds used in the composition |
| US8320424B2 (en) | 2005-12-01 | 2012-11-27 | Electro Scientific Industries, Inc. | Optical component cleanliness and debris management in laser micromachining applications |
| JP2007316652A (en) * | 2007-06-08 | 2007-12-06 | Fujifilm Corp | Photopolymerizable composition |
| JP4531078B2 (en) * | 2007-06-08 | 2010-08-25 | 富士フイルム株式会社 | Photopolymerizable composition |
| JP2009184989A (en) * | 2008-02-08 | 2009-08-20 | Toyo Ink Mfg Co Ltd | Photopolymerization initiator, polymerizable composition and method for producing polymer |
| US10400066B2 (en) | 2015-01-27 | 2019-09-03 | Hewlett-Packard Development Company, L.P. | Polymeric photoactive agents |
| US20170369720A1 (en) * | 2015-01-27 | 2017-12-28 | Hewlett-Packard Development Company, L.P. | Polymeric photo active agents |
| US10400067B2 (en) | 2015-01-27 | 2019-09-03 | Hewlett-Packard Development Company, L.P. | Polymeric photoactive agent compositions |
| US10414927B2 (en) * | 2015-01-27 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric photo active agents |
| US10619007B2 (en) | 2015-01-27 | 2020-04-14 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergists |
| JP6127223B1 (en) * | 2015-06-30 | 2017-05-10 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealant, liquid crystal display panel, and method for producing liquid crystal display panel |
| CN107735410A (en) * | 2015-06-30 | 2018-02-23 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealing agent, the manufacture method of liquid crystal display panel and liquid crystal display panel |
| WO2017002362A1 (en) * | 2015-06-30 | 2017-01-05 | 三井化学株式会社 | Photocurable resin composition, display element sealing agent, liquid crystal sealing agent, liquid crystal display panel and method for producing liquid crystal display panel |
| TWI682960B (en) * | 2015-06-30 | 2020-01-21 | 日商三井化學股份有限公司 | Photocurable resin composition, display element sealant, liquid crystal sealant, liquid crystal display panel, and method of manufacturing liquid crystal display panel |
| US11629233B2 (en) * | 2017-06-22 | 2023-04-18 | Elkem Silicones France Sas | Free-radical photoinitiators and uses of same in silicone compositions |
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