JPH01304453A - Photopolymerizable composition - Google Patents
Photopolymerizable compositionInfo
- Publication number
- JPH01304453A JPH01304453A JP13627288A JP13627288A JPH01304453A JP H01304453 A JPH01304453 A JP H01304453A JP 13627288 A JP13627288 A JP 13627288A JP 13627288 A JP13627288 A JP 13627288A JP H01304453 A JPH01304453 A JP H01304453A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- carbon atoms
- alkyl group
- compound
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- -1 iron allene Chemical class 0.000 claims abstract description 37
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052742 iron Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 150000002576 ketones Chemical class 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001442 methylidyne group Chemical group [H]C#[*] 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- ZKNDBSKUZOPJKN-UHFFFAOYSA-N 2,5-bis[3-[4-(dimethylamino)phenyl]prop-2-enylidene]cyclopentan-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=CC=C(CC1)C(=O)C1=CC=CC1=CC=C(N(C)C)C=C1 ZKNDBSKUZOPJKN-UHFFFAOYSA-N 0.000 description 1
- KKLBPVXKMBLCQX-UHFFFAOYSA-N 2,5-bis[[4-(diethylamino)phenyl]methylidene]cyclopentan-1-one Chemical compound C1=CC(N(CC)CC)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(N(CC)CC)C=C1 KKLBPVXKMBLCQX-UHFFFAOYSA-N 0.000 description 1
- GPXHIYXWGUYGHF-UHFFFAOYSA-N 2,5-bis[[4-(dimethylamino)phenyl]methylidene]cyclopentan-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(N(C)C)C=C1 GPXHIYXWGUYGHF-UHFFFAOYSA-N 0.000 description 1
- WDAFPEGNJYRORX-UHFFFAOYSA-N 2,6-bis[3-[4-(dimethylamino)phenyl]prop-2-enylidene]cyclohexan-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=CC=C(CCC1)C(=O)C1=CC=CC1=CC=C(N(C)C)C=C1 WDAFPEGNJYRORX-UHFFFAOYSA-N 0.000 description 1
- XRJCFZUOXQVWGF-UHFFFAOYSA-N 2,6-bis[[4-(dimethylamino)phenyl]methylidene]cyclohexan-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=C(CCC1)C(=O)C1=CC1=CC=C(N(C)C)C=C1 XRJCFZUOXQVWGF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- RUPYBKQBTCRLEJ-UHFFFAOYSA-N 2-[[4-(diethylamino)phenyl]methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1=CC(N(CC)CC)=CC=C1C=C1C(=O)C2=CC=CC=C2CC1 RUPYBKQBTCRLEJ-UHFFFAOYSA-N 0.000 description 1
- FOIDOYWYRJWCGQ-UHFFFAOYSA-N 2-[[4-(diethylamino)phenyl]methylidene]-3h-inden-1-one Chemical compound C1=CC(N(CC)CC)=CC=C1C=C1C(=O)C2=CC=CC=C2C1 FOIDOYWYRJWCGQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical class OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LKFAPHHHWRMPGC-UHFFFAOYSA-N butan-1-ol prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C LKFAPHHHWRMPGC-UHFFFAOYSA-N 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical group O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 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
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-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
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は可視光の領域にまで感度を有する新規な光重合
性組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel photopolymerizable composition that is sensitive to visible light.
（従来の技術）
光重合性組成物は多数の用途に広く利用されており、例
えば印刷、複写、レジスト形成その他に商業的に利用さ
れている。BACKGROUND OF THE INVENTION Photopolymerizable compositions are widely used in numerous applications, including commercial use in printing, copying, resist formation, and others.
これらの組成物は一般にエチレン性不飽和化合物または
その他のタイプの重合性化合物、光開始剤または光開始
剤系そして好ましくは溶媒可溶性または水性またはアル
カリ可溶性有機重合体結合剤化合物を含有している。と
ころが１．これらの多くの既知の有用な光重合性組成物
は、使用されている開始剤がスペクトルの紫外部領域以
外では活性化されないものが多いため、その応用範囲が
限定されているのが現状である。These compositions generally contain an ethylenically unsaturated compound or other type of polymerizable compound, a photoinitiator or photoinitiator system, and preferably a solvent-soluble or aqueous or alkali-soluble organic polymeric binder compound. However, 1. Many of these known useful photopolymerizable compositions currently have a limited range of application because the initiators used are often not activated outside the ultraviolet region of the spectrum. .
また光源として紫外線でな（可視光線を用いたり、アル
ゴンイオンレーザ−などの可視部領域に大きな発振強度
を有するレーザーで走査露光することが画像形成技術と
して要求されている。そのために可視光線に対して高い
感度を有する光重合性材料が要望され、可視光に対して
高感度な光開始剤が必要である。In addition, image forming technology requires the use of ultraviolet light (visible light) as a light source, or scanning exposure with a laser that has a large oscillation intensity in the visible region, such as an argon ion laser. There is a need for photopolymerizable materials with high sensitivity to visible light, and a photoinitiator that is highly sensitive to visible light is required.
特開昭５４−１５５２９２号公報にはへキサアリールビ
スイミダゾールを含む系、特開昭５８−１５５０３号公
報には活性ハロゲン化合物と３−ケト置換クマリン化合
物の系、特開昭５６−４６０４には３−ケト置換クマリ
ンとＮ−フェニルグリシンの系、特開昭６１−９７６５
０号公報には３−置換クマリンとキナゾリノン誘導体と
の組合せ、特開昭６１−１２３６０３号公報にはへキサ
アリールビイミダゾールと３−ケト置換クマリンとの組
合せの光開始剤系が開示されている。JP-A-54-155292 discloses a system containing hexaarylbisimidazole, JP-A-58-15503 discloses a system containing an active halogen compound and a 3-keto-substituted coumarin compound, and JP-A-56-4604 discloses a system containing a hexaarylbisimidazole. System of 3-keto-substituted coumarin and N-phenylglycine, JP-A-61-9765
No. 0 discloses a photoinitiator system of a combination of a 3-substituted coumarin and a quinazolinone derivative, and JP-A-61-123603 discloses a photoinitiator system of a combination of a hexaarylbiimidazole and a 3-keto-substituted coumarin. .
（発明が解決しようとする課題）
しかしながら前記の光開始剤系では感度が不十分であり
、より低出力のレーザーで高速度で走査露光するために
は、さらに高感度な光開始剤を見出すことが必要である
。(Problem to be Solved by the Invention) However, the sensitivity of the photoinitiator systems described above is insufficient, and in order to perform scanning exposure at high speed with a lower output laser, it is necessary to find a photoinitiator with even higher sensitivity. is necessary.
（課題を解決するための手段）
本発明者は以上の問題点を解決すべく、つまり、光重合
性組成物の可視光に対する感度を向上させる目的で、光
開始剤系について鋭意、研究、努力した結果、遂に本発
明を完成するに到った。すなわち本発明は
（ａ）少なくとも一種の常温で非ガス状のエチレン性不
飽和化合物、
（ｂ）下記一般式（Ｉ）で示される鉄アレン錯体および
（ｃ）ド記一般式（ｎ）で示されるｐ−アミノフェニル
不飽和ケトン化合物を含有する（式中Ｒは水素、アルキ
ル基、アリール基、アルコキシ基であり、ベンゼン環と
縮合多環化合物を形成していてもよい。ＸはＢＦ４．Ｐ
Ｆ６゜Ａｓ Ｆｏ 、５ｂＦＯを示す。）
本発明において使用されるエチレン性不飽和化合物は、
遊離ラジカルで開始される連鎖成長付加反応に適した単
量体であり、例えば、ペンタエリスリットトリアクリレ
ート、ポリエチレングリコールジアクリレート、トリエ
チレングリコールジアクリレート、ポリエチレングリコ
ールジメタクリレート、テトラエチレングリコールジメ
タクリレート、トリメチロールプロパントリアクリレー
ト、トリメチロールプロパントリメタクリレートなどが
Ｌげられる。(Means for Solving the Problems) In order to solve the above problems, that is, in order to improve the sensitivity of photopolymerizable compositions to visible light, the present inventors have devoted themselves to research and efforts regarding photoinitiator systems. As a result, we have finally completed the present invention. That is, the present invention provides (a) at least one ethylenically unsaturated compound that is non-gaseous at room temperature, (b) an iron allene complex represented by the following general formula (I), and (c) an iron allene complex represented by the following general formula (n). containing a p-aminophenyl unsaturated ketone compound (wherein R is hydrogen, an alkyl group, an aryl group, or an alkoxy group, and may form a fused polycyclic compound with a benzene ring.
F6°As Fo indicates 5bFO. ) The ethylenically unsaturated compound used in the present invention is
Monomers suitable for free radical initiated chain growth addition reactions, such as pentaerythritol triacrylate, polyethylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tri- Examples include methylolpropane triacrylate and trimethylolpropane trimethacrylate.
第２の成分（ｂ）は前記一般式（Ｉ）で表わされる鉄ア
レン錯体であり、Ｊ、Ｉｍａｇ、Ｓｃ１．．３０ （４
）１７４〜１７７ （１９８Ｂ）およびＪ 、Ｒａｄｉ
ａｔｉｏｎＣｕｒｉｎｇ ０ｃｔｏｂｅｒ （１９８Ｂ
） ２８〜３２にみられるような化合物があげられる。The second component (b) is an iron allene complex represented by the above general formula (I), and is an iron allene complex represented by J, Imag, Sc1. ．． 30 (4
) 174-177 (198B) and J, Radi
ationCuring 0ctober (198B
) Compounds such as those shown in Nos. 28 to 32 can be mentioned.
具体的には（η６−ベンゼン）（η５−シクロペンタジ
ェニル）鉄（ＩＩ）−へキサフルオロホスフェート、（
η６−トルエン）（η５−シクロペンタジニエル）鉄（
ｎ）へキサフルオロホスフェート、（η０−クメン）（
η−シクロペンタジェニル） 鉄（ＩＩ）へキサフルオ
ロホスフェート、（η０−ベンゼン）（η５−シクロペ
ンタジェニル） 鉄（Ｕ）へキサフルオロアルセネート
、（η６−ベンゼン）（η５−シクロペンタジェニル）
鉄（Ｉｆ）テトラフルオロボレート、（η０−ナフタレ
ン）（η５−シクロペンタジェニル） 鉄（ＩＩ）へキ
サフルオロホスフェート、（η６−アントラセン）（η
５−シクロペンタジエニル） 鉄（ＩＩ）へキサフルオ
ロホスフェート、（η６−ピレン）（η５−シクロペン
タジェニル’） 鉄（ｎ）へキサフルオロホスフェート
などがあげられる。これらの化合物はＤｏｋｌ、Ａｋｄ
、Ｎａｕｋ ５ＳＳＲＩ ４９ ６１５ （１９６３）
に法によりフェロセンより合成できる。Specifically, (η6-benzene)(η5-cyclopentadienyl)iron(II)-hexafluorophosphate, (
η6-toluene)(η5-cyclopentazinyl)iron(
n) Hexafluorophosphate, (η0-cumene) (
η-cyclopentagenyl) Iron(II) hexafluorophosphate, (η0-benzene) (η5-cyclopentagenyl) Iron(U) hexafluoroarsenate, (η6-benzene) (η5-cyclopentagenyl) )
Iron (If) tetrafluoroborate, (η0-naphthalene) (η5-cyclopentadienyl) Iron (II) hexafluorophosphate, (η6-anthracene) (η
(5-cyclopentadienyl) iron (II) hexafluorophosphate, (η6-pyrene) (η5-cyclopentadienyl') iron (n) hexafluorophosphate, and the like. These compounds are Dokl, Akd
, Nauk 5SSRI 49 615 (1963)
It can be synthesized from ferrocene by the following method.
第３の成分（ｃ）は前記一般式（ＩＩ）で表わされるｐ
−アミノフェニル不飽和ケトン化合物であり、具体的に
は２，５−ビス（４′−ジエチルアミノベンジリデン）
シクロペンタノン、２．５−ビス（４′−ジメチルアミ
ノベンジリデン）シクロペンタノン、２．８−ビス（４
’ −ジエチルアミノベンジリデン）シクロヘキサノン
、２．６−ビス（４′−ジメチルアミノベンジリデン）
シクロヘキサノン、２．５−ビス（４′−ジメチルアミ
ノシンナミリデン）シクロペンタノン、２，６−ビス（
４′−ジメチルアミノシンナミリデン）シクロヘキサノ
ン、■、３−ビス（４′−ジメチルアミノベンジリデン
）アセトン、２− （４’ −ジエチルアミノベンジリ
デン）−１−インダノン、２− （９’−ジュロリリデ
ン）−１−インダノン、２− （４’ −ジエチルアミ
ノベンジリデン）−１−テトラロン、４′−ジエチルア
ミン−２′−メチルベンジリデン−アセトフェノン、２
．５−ビス（４’ −Ｎ−エチル−Ｎ−カルボメトキシ
メチルアミノベンジリデン）シクロペンタノン、２−５
−ビス（４’ −Ｎ−エチル−Ｎ−力シボキシメチルア
ミ／ベンジリデン）ペンタノンおよびそのナトリウム塩
、２，５−ビス（４′−Ｎ−メチル−Ｎ−シアノエチル
アミノベンジリデン）シクロペンタノン、２，５−ビス
（４’ −Ｎ−エチル−Ｎ−クロルエチルアミノシンナ
リデン）シクロペンタノン、２，６−ビス（４’ −Ｎ
−シアノエチルアミノベンジリデン）シクロヘキサノン
、２− （４’ −Ｎ−エチル−Ｎ−カルポキジメチル
アミノベンジリデン）−１−インダノン、２−（４’
−Ｎ−エチル−Ｎ−カルボキシメチルアミノベンジリデ
ン）−１−テトラロンのナトリウム塩、２− （４’
−エチル−Ｎ−シアノエチルアミノベンジリデン）−１
−インダノンなどが挙げられる。The third component (c) is p represented by the general formula (II) above.
-Aminophenyl unsaturated ketone compound, specifically 2,5-bis(4'-diethylaminobenzylidene)
Cyclopentanone, 2,5-bis(4'-dimethylaminobenzylidene)cyclopentanone, 2,8-bis(4
'-diethylaminobenzylidene) cyclohexanone, 2,6-bis(4'-dimethylaminobenzylidene)
Cyclohexanone, 2,5-bis(4'-dimethylaminocinnamylidene)cyclopentanone, 2,6-bis(
4'-dimethylaminocinnamylidene)cyclohexanone, ■, 3-bis(4'-dimethylaminobenzylidene)acetone, 2-(4'-diethylaminobenzylidene)-1-indanone, 2-(9'-julolylidene)-1 -indanone, 2-(4'-diethylaminobenzylidene)-1-tetralone, 4'-diethylamine-2'-methylbenzylidene-acetophenone, 2
．． 5-bis(4'-N-ethyl-N-carbomethoxymethylaminobenzylidene)cyclopentanone, 2-5
-bis(4'-N-ethyl-N-cyboxymethylamino/benzylidene)pentanone and its sodium salt, 2,5-bis(4'-N-methyl-N-cyanoethylaminobenzylidene)cyclopentanone, 2 , 5-bis(4'-N-ethyl-N-chloroethylaminocinnaridene)cyclopentanone, 2,6-bis(4'-N
-cyanoethylaminobenzylidene)cyclohexanone, 2-(4'-N-ethyl-N-carpokydimethylaminobenzylidene)-1-indanone, 2-(4'
Sodium salt of -N-ethyl-N-carboxymethylaminobenzylidene)-1-tetralone, 2- (4'
-ethyl-N-cyanoethylaminobenzylidene)-1
- Examples include indanone.
特に感度的に好ましい化合物は、式（ｎ）においてＲ＋
＋ Ｒ２ｔ Ｒ７ｔ Ｒｓ Ｔ の少なくとも１つが
ＣＨ２Ｃ０ＯＲ，（但しＲ６は炭素数１〜５のアルキル
基を示す）またはＣＨ２Ｃ０ＯＨもしくはそのアルカリ
金属塩、アンモニウム塩、アミン塩、またはＣ２Ｈ４Ｃ
Ｆ、Ｉ 、Ｃ２Ｈ４Ｉ、Ｃ２Ｈ４ＣＱ１Ｃ２Ｈ４Ｆ、Ｃ
２Ｈ４ＣＮ。A particularly preferable compound in terms of sensitivity is R +
+ At least one of R2t R7t Rs T is CH2C0OR, (wherein R6 represents an alkyl group having 1 to 5 carbon atoms), or CH2C0OH or its alkali metal salt, ammonium salt, amine salt, or C2H4C
F, I, C2H4I, C2H4CQ1C2H4F, C
2H4CN.
Ｃ２Ｈ４Ｎ Ｏ２であるＰ−アミノフェニル不飽和ケト
ン化合物である。It is a P-aminophenyl unsaturated ketone compound which is C2H4N O2.
本発明組成物中には好ましくは熱可塑性高分子量有機重
合体結合剤を存在させてもよい。重合体結合剤タイプと
しては（１）テレフタル酸、イソフタル酸、セバシン酸
、アジピン酸およびヘキサヒドロテレフタル酸に基くコ
ポリエステル、（目）ポリアミド、（＋１１）ビニリデ
ンクロリド共重合体、（Ｉｖ）エチレン／ビニルアセテ
ート共重合体、（ｖ）セルロースエーテル、（ｖｌ）ポ
リエチレン、 （ｖｆｌ）舎外ゴム、（ｖｆｌ）セルロ
ースエステル、（ｌｘ）ホ’Ｊビニルアセテート／アク
リレートおよびポリビニルアセテート／メタクリレート
共重合体を含むポリビニルエステル、（Ｘ）ポリアクリ
レートおよびポリα−アルキルアクリレートエステル例
えばポリメチルメタクリレートおよびポリエチルメタク
リレート、（ｘｉ）４，０００〜４，０００，０００の
重量平均分子量を有する高分子量エチレンオキシド重合
体（ポリエチレングリコール） 、（ｘｌｉ）ポリ塩化
ビニルおよびその共重合体、（ｘｌｌｌ）ポリビニルア
セクール、（ｘｉｖ）ポリホルムアルデヒド、（ＸＶ）
ポリウレタン、（ｘｖｌ）ポリカーボネートおよび（Ｘ
Ｖ日）ポリスチレンがあげられる。A thermoplastic high molecular weight organic polymeric binder may preferably be present in the composition of the invention. Polymeric binder types include (1) copolyesters based on terephthalic acid, isophthalic acid, sebacic acid, adipic acid and hexahydroterephthalic acid, (I) polyamide, (+11) vinylidene chloride copolymer, (Iv) ethylene/ Contains vinyl acetate copolymer, (v) cellulose ether, (vl) polyethylene, (vfl) outside rubber, (vfl) cellulose ester, (lx) vinyl acetate/acrylate and polyvinyl acetate/methacrylate copolymer. polyvinyl esters, (X) polyacrylates and polyalkyl acrylate esters such as polymethyl methacrylate and polyethyl methacrylate, (xi) high molecular weight ethylene oxide polymers (polyethylene glycols) having a weight average molecular weight of 4,000 to 4,000,000; ), (xli) polyvinyl chloride and its copolymer, (xlll) polyvinyl acecool, (xiv) polyformaldehyde, (XV)
polyurethane, (xvl) polycarbonate and (X
Day V) Polystyrene can be mentioned.
本発明の特に好ましい態様においては、未露光光重合性
コーティングが例えばアルカリ性溶液である主として水
性の溶液には可溶性であるが、活性線放射に露光後は比
較的それに不溶性となるように、光重合性結合剤を選ぶ
。典型的にはこれらの要求を満足させる重合体はカルボ
キシル化重合体例えば遊離カルボン酸基含有ビニル付加
重合体である。好ましい結合剤としてはイソブタノール
混合物で部分エステル化された酸価約１９０、重量平均
分子量約１０．０００のスチレン／マレイン酸無水物（
１： １）の共重合体、およびスチレン／マレイン酸無
水物の共重合体とエチルアクリレート／メチルメタクリ
レート／アクリル酸のターポリマーとの組み合わせがあ
げられる。その他の好ましい結合剤群としては、ポリア
クリレートエステルおよびポリα−アルキルアクリレー
トエステル特にポリメチルメタクリレートがあげられる
。In a particularly preferred embodiment of the invention, the photopolymerizable coating is soluble in primarily aqueous solutions, such as alkaline solutions, but relatively insoluble therein after exposure to actinic radiation. Choose a sexual binder. Polymers that typically meet these requirements are carboxylated polymers, such as vinyl addition polymers containing free carboxylic acid groups. A preferred binder is styrene/maleic anhydride (partially esterified with an isobutanol mixture) having an acid value of about 190 and a weight average molecular weight of about 10,000.
1: copolymers of 1), and combinations of styrene/maleic anhydride copolymers and ethyl acrylate/methyl methacrylate/acrylic acid terpolymers. Other preferred groups of binders include polyacrylate esters and polyα-alkyl acrylate esters, especially polymethyl methacrylate.
その他の不活性添加剤例えば非重合性可塑剤、染料、顔
料および充填剤は当業者には既知であるこれら添加剤は
一般に少量で存在せしめられ、そしてこれは光重合性層
の露光を阻害させるものであるべきではない。Other inert additives such as non-polymerizable plasticizers, dyes, pigments and fillers are known to those skilled in the art.These additives are generally present in small amounts and this inhibits the exposure of the photopolymerizable layer. It shouldn't be a thing.
本発明の光重合性組成物の好ましい配合比率を成分（ａ
）であるエチレン性不飽和化合物１００重量部に対する
重量部で表わすと、成分（ｂ）である鉄アレン錯体は０
．０１〜５０重量部、特に好ましくは０．１〜３０重量
部、成分（ｃ）であるｐ−アミノフェニル不飽和ケトン
化合物は０．０１〜２０重量部、特に好ましくは０．１
〜２０重量部、結合剤は０〜１０００重量部、好ましく
は０〜５０重量部である。The preferred blending ratio of the photopolymerizable composition of the present invention is the component (a
), the iron allene complex as component (b) is expressed in parts by weight based on 100 parts by weight of the ethylenically unsaturated compound
．． 01 to 50 parts by weight, particularly preferably 0.1 to 30 parts by weight, and component (c), p-aminophenyl unsaturated ketone compound, 0.01 to 20 parts by weight, particularly preferably 0.1
-20 parts by weight, binder from 0 to 1000 parts by weight, preferably from 0 to 50 parts by weight.
本発明光重合性組成物は広範囲な種類の基材−りにコー
ティングすることができる。The photopolymerizable compositions of the present invention can be coated onto a wide variety of substrates.
「基材」とはすべての天然または合成支持体、好ましく
は可ｊＭ性または剛性のフィルムまたはシートの形で存
在しうるちのを意味している。例えば基材は金属シート
または箔、合成有機樹脂のシートまたはフィルム、セル
ロース紙、ファイバーボードその他またはこれらの物質
の２種またはそれ以上のものの複合体でありうる。特定
の基材としてはアルミナプラストアルミニウム、アノー
ド処理アルミニウム、アルミプラストポリエチレンテレ
フタレートフィルム、ポリエチレンテレフタレートフィ
ルム例えば樹脂下引きポリエチレンテレフタレートフィ
ルム、静電放電処理ポリエチレンテレフタレートフィル
ム、ポリビニルアルコールコーティングした紙、交叉結
合ポリエステルコーティング紙、ナイロン、ガラス、セ
ルロースアセテートフィルムその他があげられる。By "substrate" is meant any natural or synthetic support, preferably present in the form of a flexible or rigid film or sheet. For example, the substrate can be a metal sheet or foil, a sheet or film of synthetic organic resin, cellulose paper, fiberboard, etc. or a composite of two or more of these materials. Specific substrates include aluminated aluminum, anodized aluminum, aluminated polyethylene terephthalate film, polyethylene terephthalate film such as resin-subbed polyethylene terephthalate film, electrostatic discharge treated polyethylene terephthalate film, polyvinyl alcohol coated paper, cross-linked polyester coated paper. , nylon, glass, cellulose acetate film, and others.
特定の基材は一般に関連する適用目的により決定される
。例えば印刷回路が製造される場合には、基材はファイ
バーボード上に銅コーテイングしたプレートでありうる
。平版印刷プレートの製造においては、基材はアノード
処理アルミニウムである。The particular substrate will generally be determined by the application purpose involved. For example, if printed circuits are to be manufactured, the substrate may be a copper coated plate on fibreboard. In the manufacture of lithographic printing plates, the substrate is anodized aluminum.
好ましくは光重合性組成物の層はｏ、ｏｏｏｉインチ（
０，０００２５ｃ糟）〜約０．０１インチ（０，０２５
ｃｍ）の範囲の厚さを有しており、そして光重合性層に
活性な放射を通過しうる薄い可撓性の重合体フィルム支
持体に程度ないし中等度接着性をもって接着されている
。それに保護カバー層またはカバーシートを接着させる
ことができる。このシートはフィルム支持体と層との間
の接着力よりも小さい接着力を層に対して打している。Preferably the layer of photopolymerizable composition has a thickness of o, oooi inches (
0,00025 cm) to approximately 0.01 inch (0,025
cm) and is adhered with moderate to moderate adhesion to a thin flexible polymeric film support that is transparent to the radiation active in the photopolymerizable layer. A protective cover layer or cover sheet can be adhered thereto. The sheet provides an adhesive force to the layer that is less than the adhesive force between the film support and the layer.
特に好ましい支持体は約ｏ、ｏｏｔインチ（０，００２
５Ｃ箇）〜約０．４インチ（１，０ｃ市）の範囲の厚さ
を有する透明ポリエチレンテレフタレートフィルムであ
る。また、０．０００５インチ（０，０Ｏ１３ｃｍ）〜
０．０４インチ（０，ｌＯｃｍ）のポリエチレンは好ま
しいカッく一シートであり、ポリビニルアルコールコー
ティングは好ましいカバー層である。A particularly preferred support is about o, oot inch (0,002
The transparent polyethylene terephthalate film has a thickness ranging from 5C to about 0.4 inches (1.0C). Also, 0.0005 inch (0.0O13cm) ~
0.04 inch (0.1Ocm) polyethylene is the preferred base sheet and a polyvinyl alcohol coating is the preferred cover layer.
通常の光源としては４０５．４３Ｅ３および５４８ｎｍ
（Ｈｇ）波長に中心を有する狭いかまたは広い光バンド
を与える蛍光燈、水銀灯、金属添加ランプおよびアーク
ランプがあげられる。干渉光源はパルス式キセノン、ア
ルゴンイオン、ヘリウム−カドミウム、およびイオン化
ネオンレーザ−などである。プリントアウト系に広く使
用されている可視光発生陰極線管もまた本発明の組成物
に関して有用である。これらは一般に電気エネルギーを
光エネルギーに変換させるための手段として紫外または
可視光発生性燐光体内部コーティングをそして放射を光
感受性ターゲットに導くための手段として光学ファイバ
ーフェイスプレートを包含している。405.43E3 and 548nm as normal light sources
Fluorescent lamps, mercury vapor lamps, metal-doped lamps, and arc lamps that provide narrow or broad light bands centered at the (Hg) wavelength may be mentioned. Interference light sources include pulsed xenon, argon ion, helium-cadmium, and ionized neon lasers. Visible light producing cathode ray tubes, commonly used in printout systems, are also useful with the compositions of the present invention. These generally include an ultraviolet or visible light emitting phosphor internal coating as a means for converting electrical energy into optical energy and a fiber optic faceplate as a means for directing radiation to a light sensitive target.
（作用）
本発明の増感剤すなわち成分（ｃ）は本来、本発明に使
用される光開始剤すなわち成分（ｂ）が吸収し得ないか
または非常に小さな吸光度しか示さない可視光を効率よ
く吸収し、活性化される。(Function) The sensitizer or component (c) of the present invention originally efficiently absorbs visible light that the photoinitiator or component (b) used in the present invention cannot absorb or exhibits very low absorbance. absorbed and activated.
その杖態で本発明の増感剤は本発明で使用される光開始
剤に作用し、結果的に活性なラジカルを発生させ、その
ラジカルが組成物中のエチレン性不飽和化合物を攻゛撃
して、重合を起こすわけである。In its wand form, the sensitizer of the present invention acts on the photoinitiator used in the present invention, resulting in the generation of active radicals that attack ethylenically unsaturated compounds in the composition. This causes polymerization.
（実施例）
以下実施例により本発明を具体的に説明するがここに部
および％は重量基準ある。(Example) The present invention will be specifically explained below with reference to Examples, in which parts and percentages are based on weight.
実施例１〜１４、比較例１〜４
下引き層を有する１００μ厚さの透明なポリエチレンテ
レフタレートフィルム上に゛ド記組成の感光層塗工液を
塗布し、熱風乾燥機にて９０°Ｃ１分間乾燥し、厚さ３
μの塗膜を得た。次いでその上に７％ポリビニルアルコ
ール（完全ケン化、重合度５００）の水溶液を塗布し熱
風乾燥機で１００℃１分間乾燥して１μのオーバーコー
ト層を設けて、感度テスト片を得た。Examples 1 to 14, Comparative Examples 1 to 4 A photosensitive layer coating solution having the composition described above was applied onto a 100μ thick transparent polyethylene terephthalate film having an undercoat layer, and dried at 90°C for 1 minute in a hot air dryer. dry, thickness 3
A coating film of μ was obtained. Next, an aqueous solution of 7% polyvinyl alcohol (completely saponified, degree of polymerization: 500) was applied thereon and dried at 100° C. for 1 minute in a hot air dryer to form a 1 μm overcoat layer to obtain a sensitivity test piece.
（感光層塗工液組成）
ポリ（メタクリル酸メチル／
メタクリル酸） ５２部
７０／３０モル比
テトラエチレングリコール
ジアクリレート ４０
有機過酸化物（成分ｂ） ５ｐ−アミ
ノフェニル不飽和ケトン
（成分ｃ） ３
メタノール ２００部酢酸エチ
ル ８０クロロホルム
１２０−に記感度テスト片上にネガ
フィルムとして２１ｆ２ステツプタブレツト（人［１本
スクリーン社製グレーフィルムスケール）を重ねて、キ
セノンランプ（ウシオ電機社製ＵＸＬ−５００Ｄ−０）
に東芝社製干渉フィルターＫＬ−４９と同色ガラスフィ
ルターＹ−４５を組み合わせた光源（４９０ｎｒｎＡ）
で１５０１１の距離から５分間露光した後、３０°Ｃｏ
、７％炭酸ナトリウム水溶液に１０秒間浸漬し、水洗し
て未硬化部分を除去し乾燥した後、２１４２ステツプタ
ブレツトの完全硬化の段数（ステップ）を調べ、それを
表１と表２に示す。また比較例を表３に示す。表１ ２
．３より明らかなように本発明の実施例１〜１４は比較
例１〜４に比べ４９０ｎｍの光に対して高感度であるこ
とが判る。(Photosensitive layer coating liquid composition) Poly(methyl methacrylate/methacrylic acid) 52 parts 70/30 molar ratio Tetraethylene glycol diacrylate 40 Organic peroxide (component b) 5p-aminophenyl unsaturated ketone (component c) 3 Methanol 200 parts Ethyl acetate 80 Chloroform
A 21f2 step tablet (Gray Film Scale, manufactured by Ippon Screen Co., Ltd.) was placed as a negative film on the sensitivity test piece described in 120-, and a xenon lamp (UXL-500D-0, manufactured by Ushio Inc.) was placed.
A light source (490nrnA) that combines Toshiba's interference filter KL-49 and the same color glass filter Y-45.
After exposure for 5 minutes from a distance of 15011 at 30°Co
After immersion in a 7% sodium carbonate aqueous solution for 10 seconds, washing with water to remove uncured portions, and drying, the number of steps for complete curing of the 2142 step tablet was determined and is shown in Tables 1 and 2. Comparative examples are also shown in Table 3. Table 1 2
．． 3, it can be seen that Examples 1 to 14 of the present invention have higher sensitivity to light of 490 nm than Comparative Examples 1 to 4.
以 ド 余 白
表 １
表２
表３
（発明の効果）
本発明の光重合性組成物は、可視光に対して高感度を示
すため、低いエネルギーの露光光源を使用することがで
き、また、与えられた時間内に多数の原版を露光および
現像できる。Table 1 Table 2 Table 3 (Effects of the invention) Since the photopolymerizable composition of the present invention exhibits high sensitivity to visible light, a low energy exposure light source can be used, and Multiple masters can be exposed and developed in a given amount of time.
また、露光源を原版より遠ざけることができるため、そ
の光線が平行化され、例えば網点画像形成する場合、垂
直の側部を有するシャープな網点を形成することができ
るなど種々の利点を有する。In addition, since the exposure source can be moved away from the original, the light rays are collimated, which has various advantages such as the ability to form sharp halftone dots with vertical sides when forming halftone images, for example. .
Claims (1)
飽和化合物、 （ｂ）下記一般式（ I ）で示される鉄アレン錯体およ
び （ｃ）下記一般式（II）で示されるｐ−アミノフェニル
不飽和ケトン化合物を含有する ことを特徴とする光重合性組成物。 ▲数式、化学式、表等があります▼（ I ） （式中Ｒは水素、アルキル基、アリール基、アルコキシ
基であり、ベンゼン環と縮合多環化合物を形成していて
もよい。ＸはＢＦ＿４、ＰＦ＿６、ＡｓＦ＿６、ＳｂＦ
＿６を示す。） ▲数式、化学式、表等があります▼（II） ［式中ｍ、ｎはそれぞれ０または１であり、Ｒ＿１、Ｒ
＿２は水素原子または炭素原子数１〜５のアルキル基、
またはＣＨ＿２ＣＯＯＲ＿６（但しＲ＿６は水素原子ま
たは炭素数１〜５のアルキル基、アルカリ金属、アンモ
ニウム、アミン、またはＣ＿２Ｈ＿４ＣＦ＿３、Ｃ＿２
Ｈ＿４Ｉ、Ｃ＿２Ｈ＿４Ｂｒ、Ｃ＿２Ｈ＿４Ｃｌ、Ｃ＿
２Ｈ＿４Ｆ、Ｃ＿２Ｈ＿４ＣＮ、Ｃ＿２Ｈ＿４ＮＯ＿２
を示す）、Ｒ＾３はメチリジン基またはＲ＿４と結合し
てカルボニル基とともに環を形成することができる炭素
原子数１〜５のアルキレン−イリジン基、Ｒ＿４は炭素
原子、置換または非置換フェニル基、もしくはＲ＿３と
カルボニル基とともにインダノンまたはテトラロンを形
成する基、 Ｒ＿５は▲数式、化学式、表等があります▼ （但しＲ＿７、Ｒ＿８は水素原子または炭素原子数１〜
５のアルキル基、または ＣＨ＿２ＣＯＯＲ＿９（但しＲ＿９水素原子または炭素
数１〜５のアルキル基、アルカリ金属、アンモニウム、
アミンまたは Ｃ＿２Ｈ＿４ＣＦ＿３、Ｃ＿２Ｈ＿４Ｉ、Ｃ＿２Ｈ＿４
Ｂｒ、Ｃ＿２Ｈ＿４Ｃｌ、Ｃ＿２Ｈ＿４Ｆ、Ｃ＿２Ｈ＿
４ＣＮ、Ｃ＿２Ｈ＿４ＮＯ＿２を示す）である。[Scope of Claims] (a) at least one ethylenically unsaturated compound that is non-gaseous at room temperature; (b) an iron allene complex represented by the following general formula (I); and (c) an iron allene complex represented by the following general formula (II). A photopolymerizable composition comprising the following p-aminophenyl unsaturated ketone compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R is hydrogen, an alkyl group, an aryl group, an alkoxy group, and may form a fused polycyclic compound with a benzene ring.X is BF_4, PF_6, AsF_6, SbF
Shows _6. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, m and n are each 0 or 1, and R_1 and R
_2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms,
or CH_2COOR_6 (where R_6 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, an alkali metal, ammonium, an amine, or C_2H_4CF_3, C_2
H_4I, C_2H_4Br, C_2H_4Cl, C_
2H_4F, C_2H_4CN, C_2H_4NO_2
), R^3 is a methylidine group or an alkylene-iridine group having 1 to 5 carbon atoms that can be combined with R_4 to form a ring with a carbonyl group, R_4 is a carbon atom, a substituted or unsubstituted phenyl group, Or a group that forms indanone or tetralone with R_3 and a carbonyl group, R_5 has a ▲ mathematical formula, chemical formula, table, etc. ▼ (However, R_7 and R_8 are hydrogen atoms or a group with 1 to 1 carbon atoms)
5 alkyl group, or CH_2COOR_9 (however, R_9 hydrogen atom or alkyl group having 1 to 5 carbon atoms, alkali metal, ammonium,
Amine or C_2H_4CF_3, C_2H_4I, C_2H_4
Br, C_2H_4Cl, C_2H_4F, C_2H_
4CN, C_2H_4NO_2).
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63136272A JP2757375B2 (en) | 1988-06-02 | 1988-06-02 | Photopolymerizable composition |
| US07/360,831 US4987056A (en) | 1988-06-02 | 1989-06-02 | Photopolymerizable composition |
| DE3918105A DE3918105A1 (en) | 1988-06-02 | 1989-06-02 | PHOTOPOLYMERIZABLE COMPOSITION |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63136272A JP2757375B2 (en) | 1988-06-02 | 1988-06-02 | Photopolymerizable composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01304453A true JPH01304453A (en) | 1989-12-08 |
| JP2757375B2 JP2757375B2 (en) | 1998-05-25 |
Family
ID=15171316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63136272A Expired - Fee Related JP2757375B2 (en) | 1988-06-02 | 1988-06-02 | Photopolymerizable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2757375B2 (en) |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5365381A (en) * | 1976-11-22 | 1978-06-10 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
| JPS5390387A (en) * | 1977-01-20 | 1978-08-09 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
| JPS5710605A (en) * | 1980-06-24 | 1982-01-20 | Mitsubishi Chem Ind Ltd | Photopolymerizable composition |
| JPS60184518A (en) * | 1984-02-10 | 1985-09-20 | チバ‐ガイギー アーゲー | Curable composition and use |
| JPS6290648A (en) * | 1985-09-23 | 1987-04-25 | チバ−ガイギ− アクチエンゲゼル シヤフト | Photopolymerizing composition, photopolymerization method and formation of photographic relief image |
| JPS63309502A (en) * | 1987-06-10 | 1988-12-16 | Hitachi Chem Co Ltd | Photoinitiator and photopolymerizable composition prepared therefrom |
-
1988
- 1988-06-02 JP JP63136272A patent/JP2757375B2/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5365381A (en) * | 1976-11-22 | 1978-06-10 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
| JPS5390387A (en) * | 1977-01-20 | 1978-08-09 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
| JPS5710605A (en) * | 1980-06-24 | 1982-01-20 | Mitsubishi Chem Ind Ltd | Photopolymerizable composition |
| JPS60184518A (en) * | 1984-02-10 | 1985-09-20 | チバ‐ガイギー アーゲー | Curable composition and use |
| JPS6290648A (en) * | 1985-09-23 | 1987-04-25 | チバ−ガイギ− アクチエンゲゼル シヤフト | Photopolymerizing composition, photopolymerization method and formation of photographic relief image |
| JPS63309502A (en) * | 1987-06-10 | 1988-12-16 | Hitachi Chem Co Ltd | Photoinitiator and photopolymerizable composition prepared therefrom |
Cited By (156)
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| JP2000109509A (en) * | 1998-10-02 | 2000-04-18 | Toppan Printing Co Ltd | Visible light polymerizable composition |
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