JP2000089455A - Photopolymerizable image forming material - Google Patents
Photopolymerizable image forming materialInfo
- Publication number
- JP2000089455A JP2000089455A JP25789398A JP25789398A JP2000089455A JP 2000089455 A JP2000089455 A JP 2000089455A JP 25789398 A JP25789398 A JP 25789398A JP 25789398 A JP25789398 A JP 25789398A JP 2000089455 A JP2000089455 A JP 2000089455A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituent
- photopolymerizable
- forming material
- image forming
- 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.)
- Withdrawn
Links
- 239000000463 material Substances 0.000 title claims abstract description 38
- 150000001768 cations Chemical class 0.000 claims abstract description 42
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical compound [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims abstract 5
- -1 urethane compound Chemical class 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
- 150000001450 anions Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000007639 printing Methods 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000004970 halomethyl group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 18
- 238000012360 testing method Methods 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
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- 239000004065 semiconductor Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920005596 polymer binder Polymers 0.000 description 6
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 238000005498 polishing Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- MPSZITJFIKCNBV-UHFFFAOYSA-N cyclohexa-2,4-dien-1-imine Chemical compound N=C1CC=CC=C1 MPSZITJFIKCNBV-UHFFFAOYSA-N 0.000 description 4
- 238000007598 dipping method Methods 0.000 description 4
- 238000000866 electrolytic etching Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- LETDRANQSOEVCX-UHFFFAOYSA-N 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 LETDRANQSOEVCX-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CBQWGVMZIJNAEY-UHFFFAOYSA-N (3-butyl-2,6-difluorophenyl)-bis(2,6-difluorophenyl)borane Chemical compound CCCCC1=CC=C(F)C(B(C=2C(=CC=CC=2F)F)C=2C(=CC=CC=2F)F)=C1F CBQWGVMZIJNAEY-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 2
- XLQIRWWNVOTDQS-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]hepta-1(6),2,4-trien-4-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OC3=CC=2)=N1 XLQIRWWNVOTDQS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NXBXJOWBDCQIHF-UHFFFAOYSA-N 2-[hydroxy-[2-(2-methylprop-2-enoyloxy)ethoxy]phosphoryl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(=O)OCCOC(=O)C(C)=C NXBXJOWBDCQIHF-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QAGHEHQMRFEQMB-UHFFFAOYSA-N 2-ethylidenepropanedioic acid Chemical compound CC=C(C(O)=O)C(O)=O QAGHEHQMRFEQMB-UHFFFAOYSA-N 0.000 description 2
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VRBUPQGTJAXZAE-UHFFFAOYSA-N 2-propylidenebutanedioic acid Chemical compound CCC=C(C(O)=O)CC(O)=O VRBUPQGTJAXZAE-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- DPTGFYXXFXSRIR-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl prop-2-enoate Chemical compound C1C(COC(=O)C=C)CCC2OC21 DPTGFYXXFXSRIR-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 230000001443 photoexcitation Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052913 potassium silicate Inorganic materials 0.000 description 2
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- 238000012545 processing Methods 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
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- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 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
- PIPBVABVQJZSAB-UHFFFAOYSA-N bis(ethenyl) benzene-1,2-dicarboxylate Chemical compound C=COC(=O)C1=CC=CC=C1C(=O)OC=C PIPBVABVQJZSAB-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 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
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- PUFGCEQWYLJYNJ-UHFFFAOYSA-N didodecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCC PUFGCEQWYLJYNJ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical group CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- IYNRVIKPUTZSOR-HWKANZROSA-N ethenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC=C IYNRVIKPUTZSOR-HWKANZROSA-N 0.000 description 1
- KWWOQRSLYPHAMK-UHFFFAOYSA-N ethyl 2-hydroxybutanoate Chemical compound CCOC(=O)C(O)CC KWWOQRSLYPHAMK-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical class CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- YMFHUROFCFBBGV-UHFFFAOYSA-N heptan-1-ol;hexan-1-ol Chemical compound CCCCCCO.CCCCCCCO YMFHUROFCFBBGV-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001389 inorganic alkali salt Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PAZHGORSDKKUPI-UHFFFAOYSA-N lithium metasilicate Chemical compound [Li+].[Li+].[O-][Si]([O-])=O PAZHGORSDKKUPI-UHFFFAOYSA-N 0.000 description 1
- 229910052912 lithium silicate Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 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
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000013020 steam cleaning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical group [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SMHZUQHUCQAJLS-UHFFFAOYSA-N trifluoromethylboron Chemical compound [B]C(F)(F)F SMHZUQHUCQAJLS-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical group [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical group [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003673 urethanes Chemical class 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C1/00—Forme preparation
- B41C1/10—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme
- B41C1/1008—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme by removal or destruction of lithographic material on the lithographic support, e.g. by laser or spark ablation; by the use of materials rendered soluble or insoluble by heat exposure, e.g. by heat produced from a light to heat transforming system; by on-the-press exposure or on-the-press development, e.g. by the fountain of photolithographic materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/04—Negative working, i.e. the non-exposed (non-imaged) areas are removed
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/06—Developable by an alkaline solution
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/22—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by organic non-macromolecular additives, e.g. dyes, UV-absorbers, plasticisers
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、光重合性画像形成
材に関し、特に、近赤外レーザー光に対して高感度を示
し、平版印刷版、印刷校正用カラープルーフ、液晶ディ
スプレイやプラズマディスプレイ用カラーフィルターレ
ジスト、半導体素子の集積回路用フォトレジスト、配線
板やグラビア製版用銅エッチングレジスト等の各種感光
材として好適に用いられる光重合性画像形成材に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photopolymerizable image forming material, and more particularly to a lithographic printing plate, a color proof for print proofing, a liquid crystal display and a plasma display, which exhibit high sensitivity to near infrared laser light. The present invention relates to a photopolymerizable image forming material suitably used as various photosensitive materials such as a color filter resist, a photoresist for an integrated circuit of a semiconductor element, a copper etching resist for a wiring board and a gravure plate.
【0002】[0002]
【従来の技術】従来より、光重合性組成物の露光による
画像形成方法として、例えば、エチレン性不飽和化合物
と光重合開始剤系、或いは更に有機高分子結合材等から
なる光重合性組成物の層を支持体表面に形成し、画像露
光して露光部のエチレン性不飽和化合物を重合、硬化さ
せた後、非露光部を溶解除去することにより硬化レリー
フ画像を形成する方法、露光により光重合性組成物層の
支持体への接着強度に変化を起こさせた後、支持体を剥
離することにより画像を形成する方法、及び、光重合性
組成物層の光によるトナー付着性の変化を利用した画像
形成方法等の各種の方法が知られており、その光重合開
始剤としては、いずれも、ベンゾイン、ベンゾインアル
キルエーテル、ベンジルケタール、ベンゾフェノン、ア
ントラキノン、ベンジルケトン、或いはミヒラーケトン
等の、400nm以下の紫外線領域を中心とした短波長
の光に対して感応し得るものが用いられていた。2. Description of the Related Art Conventionally, as a method of forming an image by exposing a photopolymerizable composition, for example, a photopolymerizable composition comprising an ethylenically unsaturated compound and a photopolymerization initiator, or further comprising an organic polymer binder, etc. A method of forming a cured relief image by dissolving and removing non-exposed portions after imagewise exposing to polymerize and cure the ethylenically unsaturated compound in exposed portions, forming a layer of After causing a change in the adhesive strength of the polymerizable composition layer to the support, a method of forming an image by peeling the support, and a change in toner adhesion of the photopolymerizable composition layer due to light. Various methods such as an image forming method used are known, and all of the photopolymerization initiators include benzoin, benzoin alkyl ether, benzyl ketal, benzophenone, anthraquinone, and benzoin. Jiruketon, or the like Michler's ketone, which can be sensitive has been used for the following ultraviolet region of the short wavelength center of the light 400 nm.
【0003】一方、近年、画像形成技術の発展に伴い、
可視領域の光に対して高感度を示す感光性材料が強く要
請され、例えば、アルゴンイオンレーザーの488nm
の発振ビームを用いたレーザー製版方式に対応して50
0nm前後迄感度域を拡げた光重合性組成物が多数提案
され、更に、He−Neレーザーや半導体レーザーを用
いたレーザー製版方式や、フルカラー画像の複製技法に
対応して600nmを越える長波長領域の光に対する光
重合性組成物の研究も活発化している。On the other hand, in recent years, with the development of image forming technology,
There is a strong demand for a photosensitive material exhibiting high sensitivity to light in the visible region, for example, 488 nm of an argon ion laser.
50 corresponding to the laser plate making method using the oscillation beam of
A number of photopolymerizable compositions having a sensitivity range extended to about 0 nm have been proposed, and further, a long wavelength region exceeding 600 nm corresponding to a laser plate making method using a He-Ne laser or a semiconductor laser or a full-color image duplication technique. Research on a photopolymerizable composition for light of the same has been active.
【0004】しかしながら、従来の光重合開始剤の活性
ラジカル発生能力は、500nm以上、とりわけ600
nmを越えた波長の光に対しては、光励起エネルギーの
低下に伴って急激に感応性が減少することが知られてお
り、このような長波長領域の光に対して従来より提案さ
れている光重合性組成物は、いずれも感度的に満足でき
るものではなかった。However, the conventional photopolymerization initiator has an active radical generating ability of 500 nm or more, especially 600 nm.
It is known that the sensitivity of light having a wavelength exceeding nm rapidly decreases with a decrease in photoexcitation energy, and such light in the long wavelength region has been conventionally proposed. None of the photopolymerizable compositions was satisfactory in sensitivity.
【0005】これに対して、半導体レーザーの著しい進
歩によって700〜1300nmの長波長領域の近赤外
レーザー光源を容易に利用できるようになったことに伴
い、該レーザー光を用いた画像形成方法が注目され、例
えば、光重合開始剤系として、硼素アニオン含有塩色素
を含有する光重合性組成物(例えば、特開昭62−14
3044号、特開昭62−150242号、特開平5−
5988号、特開平5−197069号、各公報参
照。)、特定のシアニン系色素とs−トリアジン系化合
物とを含有する光重合性組成物(例えば、特開平4−3
1863号公報参照。)、特定のスクアリリウム系色素
とs−トリアジン系化合物とを含有する光重合性組成物
(例えば、特開平6−43633号公報参照。)等の層
を支持体上に形成した光重合性画像形成材が提案されて
いる。On the other hand, with the remarkable progress of semiconductor lasers, a near-infrared laser light source in a long wavelength region of 700 to 1300 nm has been easily used, and an image forming method using the laser light has been developed. Attention has been paid to, for example, a photopolymerizable composition containing a boron anion-containing salt dye as a photopolymerization initiator system (for example, see JP-A-62-14).
No. 3044, JP-A-62-150242, JP-A-5-205
No. 5988, JP-A-5-19769, and the respective publications. ), A photopolymerizable composition containing a specific cyanine dye and an s-triazine compound (see, for example,
See No. 1863. ), A photopolymerizable composition containing a specific squarylium-based dye and an s-triazine-based compound (see, for example, JP-A-6-43633), etc., formed on a support. Materials have been proposed.
【0006】しかしながら、近赤外レーザー光に感応す
る従来のこれら光重合性画像形成材は、光重合性組成物
層の支持体に対する接着性が経時によって促進され、そ
れにより、画像露光後の現像処理時に未露光部の除去が
不十分となってその残渣が生じるという問題があり、加
えて、白色蛍光灯下における取扱時に光重合反応が進行
し、安定した品質のものが得られ難いという問題もあっ
た。However, in these conventional photopolymerizable image-forming materials sensitive to near-infrared laser light, the adhesion of the photopolymerizable composition layer to the support is promoted with time, whereby the development after image exposure There is a problem that the unexposed portion is insufficiently removed during processing, resulting in the generation of residues, and in addition, a photopolymerization reaction proceeds during handling under a white fluorescent lamp, and it is difficult to obtain a product of stable quality. There was also.
【0007】[0007]
【発明が解決しようとする課題】本発明は、前述の従来
技術に鑑みてなされたものであって、従って、本発明
は、近赤外線領域の光に対して高感度を示し、経時安定
性に優れると共に、紫外線領域の光に対しては感応せ
ず、白色蛍光灯下における取扱性にも優れた光重合性画
像形成材を提供することを目的とする。SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned prior art, and therefore, the present invention has high sensitivity to light in the near-infrared region, and has a long-term stability. It is an object of the present invention to provide a photopolymerizable image forming material which is excellent, is insensitive to light in the ultraviolet region, and is excellent in handleability under a white fluorescent lamp.
【0008】[0008]
【課題を解決するための手段】本発明者等は、前記課題
を解決すべく鋭意検討した結果、特定の表面物性を有す
る支持体上に特定の光重合開始剤系を含有する光重合性
組成物の層を形成させた光重合性画像形成材が前記目的
を達成できることを見い出し本発明を完成したものであ
って、即ち、本発明は、圧着したガムテープの剥離強度
が500g/cm以下の表面を有する支持体の該表面
に、下記の(A)成分、及び、(B−1)成分、(B−
2)成分を含有する光重合性組成物の層が形成されてな
る光重合性画像形成材、を要旨とする。 (A)エチレン性不飽和化合物 (B−1)ポリメチン鎖を介して複素環が結合された構
造のシアニン系色素カチオン (B−2)有機硼素アニオンThe present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a photopolymerizable composition containing a specific photopolymerization initiator system on a support having specific surface physical properties. The present invention has been completed by finding that a photopolymerizable image-forming material having a layer of a material formed thereon can achieve the above-mentioned object. That is, the present invention relates to a surface having a peel strength of a compressed gum tape of 500 g / cm or less. The following component (A), component (B-1) and component (B-
2) A photopolymerizable image forming material formed by forming a layer of a photopolymerizable composition containing a component. (A) Ethylenically unsaturated compound (B-1) Cyanine dye cation having a heterocyclic ring bonded via a polymethine chain (B-2) Organic boron anion
【0009】又、本発明は、圧着したガムテープの剥離
強度が500g/cm以下の表面を有する支持体の該表
面に、下記の(A)成分、(B)成分、及び、(C)成
分を含有する光重合性組成物の層が形成されてなる光重
合性画像形成材、を要旨とする。 (A)エチレン性不飽和化合物 (B)ポリメチン鎖を介して複素環が結合された構造の
シアニン系色素カチオンと、有機硼素アニオン以外の対
アニオンとの塩 (C)ハロメチル基含有化合物Further, the present invention provides a support having a surface having a peel strength of a compressed gum tape of 500 g / cm or less, the following components (A), (B) and (C): A photopolymerizable image forming material formed by forming a layer of a photopolymerizable composition containing the photopolymerizable composition. (A) Ethylenically unsaturated compound (B) Salt of a cyanine dye cation having a heterocyclic ring structure via a polymethine chain and a counter anion other than organic boron anion (C) Halomethyl group-containing compound
【0010】[0010]
【発明の実施の形態】本発明において、光重合性画像形
成材を構成する支持体は、圧着したガムテープの剥離強
度が500g/cm以下の表面を有することが必須であ
る。ここで、ガムテープの剥離強度とは、支持体の表面
にガムテープ(SLIONTEC社製「SLION T
APE」)を25℃、5kg/cm2 、50cm/分で
圧着した後、該支持体を固定台上に固定し、支持体より
ガムテープを180度方向に30cm/分の速度で引っ
張って剥離する180度剥離試験における最大応力をガ
ムテープの幅で除して得られる線張力(g/cm)を言
い、本発明においては、その剥離強度が500g/cm
以下であることが必須であり、50〜350g/cmで
あるのが好ましい。ガムテープの剥離強度が前記範囲超
過では、光重合性画像形成材として、経時により現像時
の未露光部の除去が不十分となってその残渣が生じて経
時安定性が劣ることとなり、一方、前記範囲未満では、
光重合性組成物層の支持体への密着性に問題が生じ易い
傾向となる。DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, it is essential that the support constituting the photopolymerizable image forming material has a surface having a peel strength of the compressed gum tape of 500 g / cm or less. Here, the peel strength of the gum tape means that the surface of the support has a gum tape ("SLION T" manufactured by SLIONTEC).
APE ”) is pressed at 25 ° C., 5 kg / cm 2 , 50 cm / min, the support is fixed on a fixing table, and the gum tape is pulled from the support at a speed of 30 cm / min in a 180 ° direction and peeled off. It refers to the linear tension (g / cm) obtained by dividing the maximum stress in the 180-degree peel test by the width of the gum tape. In the present invention, the peel strength is 500 g / cm.
The following is essential, and it is preferably 50 to 350 g / cm. If the peel strength of the gum tape exceeds the above range, as a photopolymerizable image-forming material, the removal of unexposed portions during development becomes insufficient over time, resulting in the generation of residues and poor stability over time. Below the range,
Problems tend to occur in the adhesion of the photopolymerizable composition layer to the support.
【0011】尚、その支持体の材質としては、例えば、
アルミニウム、マグネシウム、銅、亜鉛、クロム、ニッ
ケル、鉄等の金属又はそれらを主成分とした合金の板、
それらの金属又は合金をメッキ又は蒸着した金属板、そ
れらの金属箔を貼着した紙、上質紙、アート紙、剥離紙
等の紙、ガラス、セラミックス等の無機物板、ポリエチ
レンテレフタレート、ポリメチルメタクリレート、ポリ
アミド、ポリスチレン、ポリエチレン、ポリ塩化ビニ
ル、セルローストリアセテート、セルロースアセテート
ブチレート等のプラスチックシート、それらのプラスチ
ックを塗布した紙等が挙げられ、中で、アルミニウム板
が特に好ましく、その厚さは、通常、0.01〜10m
m、好ましくは0.05〜1mm程度である。The material of the support is, for example,
Plates of metals such as aluminum, magnesium, copper, zinc, chromium, nickel, iron or alloys containing them as a main component,
Metal plates plated or vapor-deposited with these metals or alloys, paper with these metal foils attached, paper such as fine paper, art paper, release paper, glass, inorganic plates such as ceramics, polyethylene terephthalate, polymethyl methacrylate, Polyamide, polystyrene, polyethylene, polyvinyl chloride, cellulose triacetate, plastic sheets such as cellulose acetate butyrate, paper coated with such plastics and the like, among which aluminum plate is particularly preferred, the thickness of which is usually 0.01-10m
m, preferably about 0.05 to 1 mm.
【0012】アルミニウム板支持体は、その表面への光
重合性組成物層の形成に先立ち、通常、脱脂処理、粗面
化処理(砂目立て処理)、陽極酸化処理、及び水洗浄処
理等の表面処理が施される。Prior to the formation of the photopolymerizable composition layer on the surface of the aluminum plate support, the surface of the aluminum plate support is usually subjected to a degreasing treatment, a roughening treatment (graining treatment), an anodizing treatment, a water washing treatment and the like. Processing is performed.
【0013】脱脂処理は、溶剤を用いて拭き取り、浸
漬、蒸気洗浄する方法、アルカリ水溶液を用いて浸漬、
噴霧した後、酸水溶液で中和する方法、界面活性剤を用
いて洗浄、噴霧する方法等の常法に従い、通常、室温〜
80℃程度の温度で、1秒〜1分程度の時間でなされ
る。The degreasing treatment is carried out by wiping using a solvent, dipping, and steam cleaning, dipping using an alkaline aqueous solution,
After spraying, according to a conventional method such as a method of neutralizing with an aqueous acid solution, a method of washing with a surfactant, and a method of spraying, usually from room temperature to
This is performed at a temperature of about 80 ° C. for a time of about 1 second to 1 minute.
【0014】次いで施される粗面化処理(砂目立て処
理)は、ボール研磨法、ブラシ研磨法、ブラスト研磨
法、ホーニング研磨法、パフ研磨法等の機械的処理方
法、電解エッチング法、化学エッチング法等の常法に従
ってなされる。中で、塩酸又は硝酸電解液中で交流又は
直流により電解を行う電解エッチング法が好適であり、
その際、酸濃度0.1〜5重量%で、印加電圧1〜50
V、電流密度10〜200A/dm2 、電気量100〜
2000c/dm2 、温度10〜50℃程度の範囲内の
条件でなされるのが好ましい。The subsequent surface roughening treatment (graining treatment) includes mechanical treatment methods such as a ball polishing method, a brush polishing method, a blast polishing method, a honing polishing method, a puff polishing method, an electrolytic etching method, and a chemical etching method. It is done according to the usual law such as the law. Among them, an electrolytic etching method of performing electrolysis by alternating current or direct current in a hydrochloric acid or nitric acid electrolytic solution is preferable,
At this time, when the acid concentration is 0.1 to 5% by weight, the applied voltage is 1 to 50%.
V, current density 10-200 A / dm 2 , electric quantity 100-
It is preferable that the heat treatment be performed under the conditions of 2000 c / dm 2 and a temperature in the range of about 10 to 50 ° C.
【0015】次いで、電解エッチング法により粗面化さ
れた支持体は、表面のスマットの除去やピット形状のコ
ントロール等のために、硫酸、過硫酸、燐酸、硝酸、塩
酸、弗酸等の酸、又は、水酸化ナトリウム、水酸化カリ
ウム等のアルカリの水溶液に浸漬してデスマット処理が
施されるのが好ましい。Next, the support roughened by the electrolytic etching method is used to remove the surface smut and control the pit shape, etc., by using an acid such as sulfuric acid, persulfuric acid, phosphoric acid, nitric acid, hydrochloric acid, or hydrofluoric acid. Alternatively, desmutting treatment is preferably performed by dipping in an aqueous solution of an alkali such as sodium hydroxide or potassium hydroxide.
【0016】次いで施される陽極酸化処理は、硫酸、修
酸、燐酸、クロム酸、マロン酸等の1種又は2種以上を
含む水溶液を電解液とし、アルミニウム板を陽極として
電解を行うことによりなされ、これにより形成される酸
化皮膜量は、通常、1〜50mg/dm2 である。中
で、硫酸又は/及び燐酸の水溶液を電解液とする方法が
好適であり、具体的には、例えば、酸濃度10〜50重
量%で、電流密度1〜60A/dm2 、温度5〜50℃
で5〜60秒間程度行われる。The subsequent anodic oxidation treatment is performed by using an aqueous solution containing one or more of sulfuric acid, oxalic acid, phosphoric acid, chromic acid, and malonic acid as an electrolytic solution and performing electrolysis using an aluminum plate as an anode. The amount of the oxide film thus formed is usually 1 to 50 mg / dm 2 . Among them, a method in which an aqueous solution of sulfuric acid or / and phosphoric acid is used as an electrolytic solution is preferable. Specifically, for example, an acid concentration of 10 to 50% by weight, a current density of 1 to 60 A / dm 2 , and a temperature of 5 to 50 ° C
For about 5 to 60 seconds.
【0017】その後施される水洗浄処理は、水道水、地
下水等をそのまま、又は軟化して用い、通常、室温〜4
0℃程度の温度で、1秒〜5分程度の時間、シャワー、
スプレー、浸漬、塗布等することによりなされる。支持
体表面の粗さとしては、JIS B0601に規定され
る平均粗さRa で、通常、0.3〜1.0μm、好まし
くは0.4〜0.8μm程度とされる。In the subsequent water washing treatment, tap water, ground water or the like is used as it is or after softening.
Shower at a temperature of about 0 ° C. for a time of about 1 second to 5 minutes,
It is performed by spraying, dipping, coating, or the like. The roughness of the support surface, average roughness R a as defined in JIS B0601, usually, 0.3 to 1.0 [mu] m, and preferably from about 0.4~0.8Myuemu.
【0018】本発明の光重合性画像形成材において、前
記支持体表面に形成される光重合性組成物層の該光重合
性組成物を構成する(A)成分としてのエチレン性不飽
和化合物は、光重合性組成物が活性光線の照射を受けた
ときに、後述する(B−1)、(B−2)成分、或い
は、(B)、(C)成分の光重合開始剤系の作用により
付加重合し、場合により架橋、硬化するようなエチレン
性不飽和二重結合を有する単量体、及び、主鎖又は側鎖
にこのような二重結合を有する重合体を言う。尚、ここ
で言う単量体の意味するところは、いわゆる重合体に相
対する概念であって、狭義の単量体以外にも、二量体、
三量体、その他オリゴマーをも包含するものである。In the photopolymerizable image forming material of the present invention, the ethylenically unsaturated compound as the component (A) constituting the photopolymerizable composition in the photopolymerizable composition layer formed on the surface of the support is preferably When the photopolymerizable composition is irradiated with actinic rays, the action of the photopolymerization initiator system of the components (B-1) and (B-2) described later or the components (B) and (C) And a polymer having such an ethylenically unsaturated double bond which can be crosslinked and cured in some cases, and a polymer having such a double bond in a main chain or a side chain. The meaning of the monomer here is a concept corresponding to a so-called polymer, and in addition to the monomer in a narrow sense, a dimer,
It also includes trimers and other oligomers.
【0019】本発明におけるこのエチレン性不飽和化合
物としては、ヘキサメチレンジイソシアネート、トリメ
チルヘキサメチレンジイソシアネート等の脂肪族イソシ
アネート、シクロヘキサンジイソシアネート、イソホロ
ンジイソシアネート等の脂環式イソシアネート、トリレ
ンジイソシアネート、ジフェニルメタンジイソシアネー
ト等の芳香族イソシアネート等の有機イソシアネート化
合物と、グリセロールジ(メタ)アクリレート、ペンタ
エリスリトールトリ(メタ)アクリレート、テトラメチ
ロールエタントリ(メタ)アクリレート等の(メタ)ア
クリロイルオキシアルキル基含有ヒドロキシ化合物との
反応によって得られる(メタ)アクリロイルオキシアル
キル基含有ウレタン化合物が好ましく、特に、下記一般
式(I) で表されるものが好ましい。尚、本発明におい
て、「(メタ)アクリル」とは、アクリル及びメタクリ
ルを意味するものとする。Examples of the ethylenically unsaturated compound in the present invention include aliphatic isocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic isocyanates such as cyclohexane diisocyanate and isophorone diisocyanate; aromatics such as tolylene diisocyanate and diphenylmethane diisocyanate. Obtained by reacting an organic isocyanate compound such as an aromatic isocyanate with a hydroxy compound containing a (meth) acryloyloxyalkyl group such as glycerol di (meth) acrylate, pentaerythritol tri (meth) acrylate, or tetramethylolethane tri (meth) acrylate. (Meth) acryloyloxyalkyl group-containing urethane compounds are preferred, and particularly those represented by the following general formula (I) Is preferred. In the present invention, “(meth) acryl” means acryl and methacryl.
【0020】[0020]
【化5】 Embedded image
【0021】〔式(I) 中、R0 は水素原子又はメチル基
を示し、Uはイソシアネート残基を示し、aは0〜3の
整数、bは1〜3の整数、cは1〜3の整数である。〕 ここで、式(I) のUとしては、具体的には、例えば、炭
素数1〜10、好ましくは5〜7のアルキレン基、トリ
レン基、又はイソシアヌル酸残基等が挙げられる。これ
ら化合物の具体例を以下に示す。[In the formula (I), R 0 represents a hydrogen atom or a methyl group, U represents an isocyanate residue, a is an integer of 0 to 3, b is an integer of 1 to 3, c is 1 to 3 Is an integer. Here, specific examples of U in the formula (I) include an alkylene group having 1 to 10 carbon atoms, preferably 5 to 7 carbon atoms, a tolylene group, or an isocyanuric acid residue. Specific examples of these compounds are shown below.
【0022】[0022]
【化6】 Embedded image
【0023】[0023]
【化7】 Embedded image
【0024】[0024]
【化8】 Embedded image
【0025】[0025]
【化9】 Embedded image
【0026】[0026]
【化10】 Embedded image
【0027】[0027]
【化11】 Embedded image
【0028】本発明における光重合性組成物に占める
(A)成分としての前記(メタ)アクリロイルオキシア
ルキル基含有ウレタン化合物の割合は、10〜60重量
%であるのが好ましく、20〜50重量%であるのが更
に好ましい。前記範囲未満では光重合性画像形成材とし
て耐刷性が低下する傾向となり、前記範囲超過では経時
安定性が劣る傾向となる。The proportion of the (meth) acryloyloxyalkyl group-containing urethane compound as the component (A) in the photopolymerizable composition of the present invention is preferably from 10 to 60% by weight, and preferably from 20 to 50% by weight. Is more preferable. When the amount is less than the above range, the printing durability tends to decrease as a photopolymerizable image forming material, and when the amount exceeds the above range, the stability with time tends to be inferior.
【0029】又、本発明において好適なエチレン性不飽
和化合物として、(メタ)アクリロイルオキシアルキル
基含有ホスフェート化合物が挙げられ、特に、下記一般
式(II)で表されるものが好ましい。Further, as the ethylenically unsaturated compound suitable in the present invention, a phosphate compound containing a (meth) acryloyloxyalkyl group can be mentioned, and a compound represented by the following formula (II) is particularly preferable.
【0030】[0030]
【化12】 Embedded image
【0031】〔式(II)中、R0 は水素原子又はメチル基
を示し、dは1〜25の整数、eは1又は2である。〕 ここで、式(II)のdは1〜10であるのが耐刷性及び非
画像部の抜け性の面で好ましく、これら化合物の具体例
としては、メタアクリロイルオキシエチルホスフェー
ト、ビス(メタアクリロイルオキシエチル)ホスフェー
ト等が挙げられる。[In the formula (II), R 0 represents a hydrogen atom or a methyl group, d is an integer of 1 to 25, and e is 1 or 2. Here, d in the formula (II) is preferably 1 to 10 in terms of printing durability and removability of a non-image portion. Specific examples of these compounds include methacryloyloxyethyl phosphate and bis (meth Acryloyloxyethyl) phosphate and the like.
【0032】本発明における光重合性組成物に占める
(A)成分としての前記(メタ)アクリロイルオキシア
ルキル基含有ホスフェート化合物の割合は、0.1〜3
0重量%であるのが好ましく、0.5〜20重量%であ
るのが更に好ましい。前記範囲未満では光重合性画像形
成材として組成物層の支持体に対する密着性が劣る傾向
となり、前記範囲超過では感度が低下する傾向となる。The proportion of the (meth) acryloyloxyalkyl group-containing phosphate compound as the component (A) in the photopolymerizable composition of the present invention is from 0.1 to 3%.
It is preferably 0% by weight, more preferably 0.5 to 20% by weight. Below the above range, the adhesion of the composition layer to the support as a photopolymerizable image forming material tends to be poor, and above the above range, the sensitivity tends to decrease.
【0033】更に、本発明において好適なエチレン性不
飽和化合物として、(メタ)アクリロイルオキシアルキ
ル基含有ヒドロキシ化合物が挙げられ、特に、下記一般
式(III) で表されるものが好ましい。Further, as the ethylenically unsaturated compound suitable in the present invention, a hydroxy compound having a (meth) acryloyloxyalkyl group can be mentioned, and a compound represented by the following formula (III) is particularly preferable.
【0034】[0034]
【化13】 Embedded image
【0035】〔式(III) 中、R0 は水素原子又はメチル
基を示し、Vは多価アルコール又は多価フェノール残基
を示し、fは1〜6の整数、gは2〜6の整数、hは1
〜6の整数である。〕 ここで、式(III) のVとしては、具体的には、例えば、
アルキレン基、4,4’−ジヒドロキシビフェニル残
基、2,2−ビス(4−ヒドロキシフェニル)プロパン
残基等が挙げられ、これら化合物の具体例としては、エ
チレングリコールのアクリロイルエチレンオキシド付加
物、2,2−ビス(4−ヒドロキシフェニル)プロパン
のアクリロイルジエチレンオキシド付加物等が挙げられ
る。[In the formula (III), R 0 represents a hydrogen atom or a methyl group, V represents a polyhydric alcohol or a polyhydric phenol residue, f is an integer of 1 to 6, g is an integer of 2 to 6 , H is 1
6 to an integer. Here, as V in the formula (III), specifically, for example,
Examples thereof include an alkylene group, a 4,4′-dihydroxybiphenyl residue, and a 2,2-bis (4-hydroxyphenyl) propane residue. Specific examples of these compounds include acryloylethylene oxide adduct of ethylene glycol, Acryloyldiethylene oxide adduct of 2-bis (4-hydroxyphenyl) propane and the like can be mentioned.
【0036】本発明における光重合性組成物に占める
(A)成分としての前記(メタ)アクリロイルオキシア
ルキル基含有ヒドロキシ化合物の割合は、10〜60重
量%であるのが好ましく、20〜50重量%であるのが
更に好ましい。前記範囲未満では光重合性画像形成材と
して組成物層の支持体に対する密着性が劣る傾向とな
り、前記範囲超過では感度が低下する傾向となる。The proportion of the (meth) acryloyloxyalkyl group-containing hydroxy compound as the component (A) in the photopolymerizable composition of the present invention is preferably from 10 to 60% by weight, and more preferably from 20 to 50% by weight. Is more preferable. Below the above range, the adhesion of the composition layer to the support as a photopolymerizable image forming material tends to be poor, and above the above range, the sensitivity tends to decrease.
【0037】更に又、本発明において好適なエチレン性
不飽和化合物として、特許第2700168号公報等に
記載される(メタ)アクリロイルオキシアルキル基含有
アミン化合物が挙げられ、特に、下記一般式(IV)で表さ
れるものが好ましい。Further, as the ethylenically unsaturated compound suitable in the present invention, there may be mentioned a (meth) acryloyloxyalkyl group-containing amine compound described in Japanese Patent No. 2700168 and the like. Particularly, the following general formula (IV) Is preferably represented by
【0038】[0038]
【化14】 Embedded image
【0039】〔式(IV)中、R0 は水素原子又はメチル基
を示し、Qは水素原子、又は置換基を有していてもよい
アルキル基を示し、該アルキル基は互いに連結して環状
構造を形成していてもよく、iは1〜12の整数、jは
0〜5の整数、kは2〜12の整数、mは0又は1、n
は0又は1、oは1〜5の整数、pは1〜3の整数であ
り、Qが水素原子のときはpは2又は3である。〕[In the formula (IV), R 0 represents a hydrogen atom or a methyl group, Q represents a hydrogen atom or an alkyl group which may have a substituent, and the alkyl groups are linked to each other to form a ring. May form a structure, i is an integer of 1 to 12, j is an integer of 0 to 5, k is an integer of 2 to 12, m is 0 or 1, n
Is 0 or 1, o is an integer of 1 to 5, p is an integer of 1 to 3, and when Q is a hydrogen atom, p is 2 or 3. ]
【0040】ここで、式(IV)において、アルキル基であ
るときのQは、炭素数が通常1〜15、好ましくは1〜
5であって、鎖状、又は、ピペリジル基、ピペラジニル
基等の環状であり、iは1〜3、jは0又は1、oは1
〜3、kは2〜6であるのが好ましく、これら化合物の
具体例としては、トリス((メタ)アクリロイルオキシ
エチル)アミン、N−(メタ)アクリロイルオキシエチ
ルアミノカルボニル−2−(メタ)アクリロイルオキシ
エチルアミノカルボキシメチル−ピペリジン、N−(メ
タ)アクリロイルオキシエチルアミノカルボニル−N’
−(メタ)アクリロイルオキシエチルアミノカルボキシ
メチル−ピペラジン等が挙げられる。Here, in the formula (IV), Q when it is an alkyl group usually has 1 to 15 carbon atoms, preferably 1 to 15 carbon atoms.
5, a chain or cyclic such as a piperidyl group or a piperazinyl group, i is 1 to 3, j is 0 or 1, and o is 1
And k are preferably 2 to 6. Specific examples of these compounds include tris ((meth) acryloyloxyethyl) amine, N- (meth) acryloyloxyethylaminocarbonyl-2- (meth) acryloyl Oxyethylaminocarboxymethyl-piperidine, N- (meth) acryloyloxyethylaminocarbonyl-N ′
-(Meth) acryloyloxyethylaminocarboxymethyl-piperazine and the like.
【0041】本発明における光重合性組成物に占める
(A)成分としての前記(メタ)アクリロイルオキシア
ルキル基含有アミン化合物の割合は、0.1〜50重量
%であるのが好ましく、0.5〜30重量%であるのが
更に好ましい。前記範囲未満では光重合性画像形成材と
して耐刷性、経時安定性が低下する傾向となり、前記範
囲超過では感度が低下する傾向となる。The proportion of the (meth) acryloyloxyalkyl group-containing amine compound as the component (A) in the photopolymerizable composition of the present invention is preferably from 0.1 to 50% by weight, and more preferably from 0.5 to 50% by weight. More preferably, it is from about 30% by weight to about 30% by weight. If the amount is less than the above range, the printing durability and the stability over time tend to decrease as the photopolymerizable image forming material, and if the amount exceeds the above range, the sensitivity tends to decrease.
【0042】尚、本発明においては、(A)成分のエチ
レン性不飽和化合物として、前記の(メタ)アクリロイ
ルオキシアルキル基含有ウレタン化合物、(メタ)アク
リロイルオキシアルキル基含有ホスフェート化合物、
(メタ)アクリロイルオキシアルキル基含有ヒドロキシ
化合物、及び、(メタ)アクリロイルオキシアルキル基
含有アミン化合物の外に、単量体としては、例えば、
(1) (メタ)アクリル酸等の不飽和カルボン酸類、(2)
これらのアルキルエステル類、(3) エチレングリコール
ジ(メタ)アクリレート、ジエチレングリコールジ(メ
タ)アクリレート、トリエチレングリコールジ(メタ)
アクリレート、トリメチロールエタントリ(メタ)アク
リレート、トリメチロールプロパントリ(メタ)アクリ
レート、ペンタエリスリトールジ(メタ)アクリレー
ト、ペンタエリスリトールトリ(メタ)アクリレート、
ペンタエリスリトールテトラ(メタ)アクリレート、ジ
ペンタエリスリトールテトラ(メタ)アクリレート、ジ
ペンタエリスリトールペンタ(メタ)アクリレート、ジ
ペンタエリスリトールヘキサ(メタ)アクリレート、グ
リセロールジ(メタ)アクリレート、グリセロールトリ
(メタ)アクリレート、及び同様のイタコネート、クロ
トネート、マレエート等の脂肪族ポリヒドロキシ化合物
と不飽和カルボン酸とのエステル類、(4) ヒドロキノン
ジ(メタ)アクリレート、レゾルシンジ(メタ)アクリ
レート、ピロガロールトリ(メタ)アクリレート等の芳
香族ポリヒドロキシ化合物と不飽和カルボン酸とのエス
テル類、(5)エチレングリコールと(メタ)アクリル酸
とフタル酸との縮合物、ジエチレングリコールと(メ
タ)アクリル酸とマレイン酸との縮合物、ペンタエリス
リトールと(メタ)アクリル酸とテレフタル酸との縮合
物、ブタンジオールとグリセリンと(メタ)アクリル酸
とアジピン酸との縮合物等のポリヒドロキシ化合物と不
飽和カルボン酸と多価カルボン酸との縮合物類、(6) ポ
リイソシアネート化合物と水酸基含有ビニル化合物との
付加反応物等のビニルウレタン類、(7) 多価エポキシ化
合物とヒドロキシエチル(メタ)アクリレート等の水酸
基含有(メタ)アクリレートとの付加反応物等のエポキ
シ(メタ)アクリレート類、(8) エチレンビス(メタ)
アクリルアミド等のアクリルアミド類、(9) フタル酸ジ
アリル等のアリルエステル類、(10)ジビニルフタレート
等のビニル基含有化合物、等が用いられてもよい。In the present invention, the (meth) acryloyloxyalkyl group-containing urethane compound, the (meth) acryloyloxyalkyl group-containing phosphate compound,
In addition to the (meth) acryloyloxyalkyl group-containing hydroxy compound and the (meth) acryloyloxyalkyl group-containing amine compound, as the monomer, for example,
(1) unsaturated carboxylic acids such as (meth) acrylic acid, (2)
These alkyl esters, (3) ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate
Acrylate, trimethylolethane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate,
Pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, glycerol di (meth) acrylate, glycerol tri (meth) acrylate, and Similar esters of aliphatic polyhydroxy compounds such as itaconate, crotonate and maleate with unsaturated carboxylic acids, and (4) aromatics such as hydroquinone di (meth) acrylate, resorcin di (meth) acrylate and pyrogallol tri (meth) acrylate Esters of polyhydroxy compound and unsaturated carboxylic acid, (5) Condensate of ethylene glycol, (meth) acrylic acid and phthalic acid, diethylene glycol, (meth) acrylic acid and male Polyhydroxy compounds such as condensates with carboxylic acids, pentaerythritol with (meth) acrylic acid and terephthalic acid, and condensates with butanediol, glycerin, (meth) acrylic acid and adipic acid, and unsaturated carboxylic acids (6) Vinyl urethanes such as addition products of polyisocyanate compounds and hydroxyl-containing vinyl compounds, (7) Hydroxyl groups such as polyethyl epoxy compounds and hydroxyethyl (meth) acrylate Epoxy (meth) acrylates such as addition reaction products with contained (meth) acrylate, (8) ethylenebis (meth)
Acrylamides such as acrylamide, (9) allyl esters such as diallyl phthalate, and (10) vinyl group-containing compounds such as divinyl phthalate may be used.
【0043】又、重合体としては、例えば、主鎖に二重
結合を有するものとして、(11)不飽和ジカルボン酸とジ
ヒドロキシ化合物との重縮合反応により得られるポリエ
ステル類、(12)不飽和ジカルボン酸とジアミン化合物と
の重縮合反応により得られるポリアミド類等、側鎖に二
重結合を有するものとして、(13)イタコン酸、エチリデ
ンマロン酸、プロピリデンコハク酸等とジヒドロキシ化
合物との重縮合反応により得られるポリエステル類、(1
4)イタコン酸、エチリデンマロン酸、プロピリデンコハ
ク酸等とジアミン化合物との重縮合反応により得られる
ポリアミド類、(15)ポリビニルアルコール、ポリ(2−
ヒドロキシエチルメタクリレート)、ポリエピクロルヒ
ドリン等の側鎖にヒドロキシル基やハロゲン化メチル基
等の如き反応活性な官能基を有する重合体と不飽和カル
ボン酸との反応により得られる重合体、等が用いられて
もよい。As the polymer, for example, those having a double bond in the main chain include (11) polyesters obtained by a polycondensation reaction between an unsaturated dicarboxylic acid and a dihydroxy compound, and (12) an unsaturated dicarboxylic acid. Polyamides obtained by the polycondensation reaction of an acid and a diamine compound, such as polyamides having a double bond in the side chain, (13) polycondensation reaction of a dihydroxy compound with itaconic acid, ethylidene malonic acid, propylidene succinic acid, etc. Polyesters obtained by
4) Polyamides obtained by the polycondensation reaction of itaconic acid, ethylidene malonic acid, propylidene succinic acid and the like with a diamine compound, (15) polyvinyl alcohol, poly (2-
(Hydroxyethyl methacrylate), a polymer obtained by reacting a polymer having a reactive group such as a hydroxyl group or a methyl halide group in a side chain thereof with an unsaturated carboxylic acid, such as polyepichlorohydrin, etc. Is also good.
【0044】本発明における光重合性組成物を構成する
(B−1)成分のシアニン系色素カチオン、及び、
(B)成分のシアニン系色素カチオンと対アニオンとの
塩におけるシアニン系色素カチオンは、ポリメチン鎖を
介して複素環が結合された構造のものであり、波長域7
00〜1300nmの近赤外線領域の一部又は全部に吸
収帯を有する近赤外線吸収色素カチオンが特に有効であ
る。これらの近赤外線吸収色素カチオンは、前記波長域
の光を効率よく吸収し、その光励起エネルギーを後述す
る(B−2)成分の有機硼素アニオン又は(C)成分の
ハロメチル基含有化合物に伝え、該(B−2)成分又は
(C)成分を分解し、(A)成分の前記エチレン性不飽
和化合物の重合を誘起する活性ラジカルを発生させる増
感機能を有する一方、紫外線領域の光は殆ど吸収しない
か、吸収しても実質的に感応せず、白色蛍光灯に含まれ
るような弱い紫外線によっては組成物を変成させる作用
のない化合物である。The cyanine dye cation (B-1) constituting the photopolymerizable composition of the present invention, and
The cyanine dye cation in the salt of the cyanine dye cation and the counter anion of the component (B) has a structure in which a heterocyclic ring is bonded via a polymethine chain, and has a wavelength range of 7.
A near-infrared absorbing dye cation having an absorption band in a part or the whole of the near infrared region of 00 to 1300 nm is particularly effective. These near-infrared absorbing dye cations efficiently absorb light in the above-mentioned wavelength range, and transmit the photoexcitation energy to an organic boron anion of the component (B-2) or a halomethyl group-containing compound of the component (C) described below. While it has a sensitizing function of decomposing the component (B-2) or the component (C) to generate an active radical that induces the polymerization of the ethylenically unsaturated compound of the component (A), it absorbs almost all light in the ultraviolet region. It is a compound that does not act or does not substantially respond to absorption, and has no function of denaturing the composition due to weak ultraviolet rays contained in white fluorescent lamps.
【0045】本発明において、これらのシアニン系色素
カチオンとしては、窒素原子、酸素原子、又は硫黄原子
等を含む複素環がポリメチン(−CH=)n 鎖で結合さ
れた、広義の所謂シアニン系色素カチオンであって、具
体的には、例えば、キノリン系(所謂、シアニン系)、
インドール系(所謂、インドシアニン系)、ベンゾチア
ゾール系(所謂、チオシアニン系)、イミノシクロヘキ
サジエン系(所謂、ポリメチン系)、ピリリウム系、チ
アピリリウム系、スクアリリウム系、クロコニウム系、
アズレニウム系等の色素カチオンが挙げられ、中で、キ
ノリン系、インドール系、ベンゾチアゾール系、イミノ
シクロヘキサジエン系、ピリリウム系、又はチアピリリ
ウム系の色素カチオンが好ましい。In the present invention, these cyanine dye cations include, in a broad sense, a so-called cyanine dye in which a heterocyclic ring containing a nitrogen atom, an oxygen atom, a sulfur atom or the like is bonded by a polymethine (—CH =) n chain. A cation, specifically, for example, a quinoline-based (so-called cyanine-based)
Indole (so-called indocyanine), benzothiazole (so-called thiocyanine), iminocyclohexadiene (so-called polymethine), pyrylium, thiapyrylium, squarylium, croconium,
Azurenium-based dye cations are exemplified, and among them, quinoline-based, indole-based, benzothiazole-based, iminocyclohexadiene-based, pyrylium-based, and thiapyrylium-based dye cations are preferable.
【0046】本発明においては、前記シアニン系色素カ
チオンの中で、キノリン系色素カチオンとしては、特
に、下記一般式(Va) 、(Vb)、又は(Vc)で表されるもの
が好ましい。In the present invention, among the cyanine dye cations, the quinoline dye cation is particularly preferably one represented by the following formula (Va), (Vb) or (Vc).
【0047】[0047]
【化15】 Embedded image
【0048】〔式(Va)、(Vb)、及び(Vc)中、R1 及びR
2 は各々独立して、置換基を有していてもよいアルキル
基、置換基を有していてもよいアルケニル基、置換基を
有していてもよいアルキニル基、又は置換基を有してい
てもよいフェニル基を示し、L1 は置換基を有していて
もよいトリ、ペンタ、ヘプタ、ノナ、又はウンデカメチ
ン基を示し、該ペンタ、ヘプタ、ノナ、又はウンデカメ
チン基上の2つの置換基が互いに連結して炭素数4〜7
のシクロアルケン環、シクロアルケノン環、シクロアル
ケンジオン環、又はシクロアルケンチオン環を形成して
いてもよく、キノリン環は置換基を有していてもよく、
その場合、隣接する2つの置換基が互いに連結して縮合
ベンゼン環を形成していてもよい。〕In the formulas (Va), (Vb) and (Vc), R 1 and R
2 each independently has an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, or a group which has a substituent. L 1 represents a tri, penta, hepta, nona, or undecamethine group which may have a substituent, and two substituents on the penta, hepta, nona, or undecamethine group Are connected to each other to have 4 to 7 carbon atoms.
May form a cycloalkene ring, a cycloalkeneone ring, a cycloalkenedione ring, or a cycloalkenethione ring, and the quinoline ring may have a substituent,
In that case, two adjacent substituents may be connected to each other to form a fused benzene ring. ]
【0049】ここで、式(Va)、(Vb)、及び(Vc)中のR1
及びR2 がアルキル基であるときの炭素数は通常1〜1
5、好ましくは1〜5、アルケニル基、アルキニル基で
あるときの炭素数は通常2〜15、好ましくは2〜5で
あり、それらにおける置換基としては、アルコキシ基、
フェノキシ基、ヒドロキシ基、又はフェニル基等が挙げ
られ、L1 における置換基としては、アルキル基、アミ
ノ基、又はハロゲン原子等が挙げられ、キノリン環にお
ける置換基としては、アルキル基、アルコキシ基、ニト
ロ基、又はハロゲン原子等が挙げられる。Here, R 1 in the formulas (Va), (Vb) and (Vc)
And when R 2 is an alkyl group, the number of carbon atoms is usually 1 to 1
5, preferably 1 to 5, and when it is an alkenyl group or an alkynyl group, the number of carbon atoms is usually 2 to 15, preferably 2 to 5, and as a substituent therefor, an alkoxy group,
A phenoxy group, a hydroxy group, or a phenyl group; a substituent in L 1 includes an alkyl group, an amino group, or a halogen atom; and a substituent in the quinoline ring includes an alkyl group, an alkoxy group, Examples thereof include a nitro group and a halogen atom.
【0050】又、インドール系、及びベンゾチアゾール
系色素カチオンとしては、特に、下記一般式(VI)で表さ
れるものが好ましい。As the indole-based and benzothiazole-based dye cations, those represented by the following general formula (VI) are particularly preferred.
【0051】[0051]
【化16】 Embedded image
【0052】〔式(VI)中、Y1 及びY2 は各々独立し
て、ジアルキルメチレン基又は硫黄原子を示し、R3 及
びR4 は各々独立して、置換基を有していてもよいアル
キル基、置換基を有していてもよいアルケニル基、置換
基を有していてもよいアルキニル基、又は置換基を有し
ていてもよいフェニル基を示し、L2 は置換基を有して
いてもよいトリ、ペンタ、ヘプタ、ノナ、又はウンデカ
メチン基を示し、該ペンタ、ヘプタ、ノナ、又はウンデ
カメチン基上の2つの置換基が互いに連結して炭素数4
〜7のシクロアルケン環、シクロアルケノン環、シクロ
アルケンジオン環、又はシクロアルケンチオン環を形成
していてもよく、縮合ベンゼン環は置換基を有していて
もよく、その場合、隣接する2つの置換基が互いに連結
して縮合ベンゼン環を形成していてもよい。〕[In the formula (VI), Y 1 and Y 2 each independently represent a dialkylmethylene group or a sulfur atom, and R 3 and R 4 each independently may have a substituent. An alkyl group, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, or a phenyl group which may have a substituent, and L 2 has a substituent Represents a tri, penta, hepta, nona, or undecamethine group which may be substituted, and two substituents on the penta, hepta, nona, or undecamethine group are connected to each other to have 4 carbon atoms.
To 7 may form a cycloalkene ring, a cycloalkeneone ring, a cycloalkenedione ring, or a cycloalkenethione ring, and the fused benzene ring may have a substituent. The substituents may be linked to each other to form a fused benzene ring. ]
【0053】ここで、式(VI)中のR3 及びR4 がアルキ
ル基であるときの炭素数は通常1〜15、好ましくは1
〜5、アルケニル基、アルキニル基であるときの炭素数
は通常2〜15、好ましくは2〜5であり、それらにお
ける置換基としては、アルコキシ基、フェノキシ基、ヒ
ドロキシ基、又はフェニル基等が挙げられ、L2 におけ
る置換基としては、アルキル基、アミノ基、又はハロゲ
ン原子等が挙げられ、ベンゼン環における置換基として
は、アルキル基、アルコキシ基、ニトロ基、又はハロゲ
ン原子等が挙げられる。Here, when R 3 and R 4 in the formula (VI) are an alkyl group, the number of carbon atoms is usually 1 to 15, preferably 1 to 15.
When it is an alkenyl group or an alkynyl group, the number of carbon atoms is usually 2 to 15, preferably 2 to 5, and examples of the substituent include an alkoxy group, a phenoxy group, a hydroxy group, and a phenyl group. It is, as the substituent in L 2, an alkyl group, an amino group, or a halogen atom, and examples of the substituent in the benzene ring, an alkyl group, an alkoxy group, and a nitro group, or a halogen atom and the like.
【0054】又、イミノシクロヘキサジエン系色素カチ
オンとしては、特に、下記一般式(VII) で表されるもの
が好ましい。As the iminocyclohexadiene dye cation, those represented by the following formula (VII) are particularly preferable.
【0055】[0055]
【化17】 Embedded image
【0056】〔式(VII) 中、R5 、R6 、R7 、及びR
8 は各々独立して、アルキル基を示し、R9 及びR10は
各々独立して、置換基を有していてもよいアリール基、
フリル基、又はチエニル基を示し、L3 は置換基を有し
ていてもよいモノ、トリ、ペンタ、又はヘプタメチン基
を示し、該トリ、ペンタ、又はヘプタメチン基上の2つ
の置換基が互いに連結して炭素数4〜7のシクロアルケ
ン環、シクロアルケノン環、シクロアルケンジオン環、
又はシクロアルケンチオン環を形成していてもよく、キ
ノン環及びベンゼン環は置換基を有していてもよい。〕[In the formula (VII), R 5 , R 6 , R 7 and R
8 each independently represents an alkyl group; R 9 and R 10 each independently represent an aryl group which may have a substituent;
L 3 represents a furyl group or a thienyl group, L 3 represents a mono, tri, penta or heptamethine group which may have a substituent, and two substituents on the tri, penta or heptamethine group are linked to each other A cycloalkene ring having 4 to 7 carbon atoms, a cycloalkeneone ring, a cycloalkenedione ring,
Alternatively, a cycloalkenethione ring may be formed, and the quinone ring and the benzene ring may have a substituent. ]
【0057】ここで、式(VII) 中のR5 、R6 、R7 、
及びR8 がアルキル基であるときの炭素数は通常1〜1
5、好ましくは1〜5であり、R9 及びR10がアリール
基であるときの炭素数は通常6〜20、好ましくは6〜
15であり、R9 及びR10として具体的には、フェニル
基、1−ナフチル基、2−ナフチル基、2−フリル基、
3−フリル基、2−チエニル基、3−チエニル基等が挙
げられ、それらの置換基としては、アルキル基、アルコ
キシ基、ジアルキルアミノ基、ヒドロキシ基、又はハロ
ゲン原子等が挙げられ、L3 における置換基としては、
アルキル基、アミノ基、又はハロゲン原子等が挙げられ
る。Here, R 5 , R 6 , R 7 in the formula (VII)
And when R 8 is an alkyl group, the number of carbon atoms is usually 1 to 1
5, preferably 1 to 5, and the carbon number when R 9 and R 10 are an aryl group is usually 6 to 20, preferably 6 to
15, specifically as R 9 and R 10 , a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-furyl group,
3-furyl, 2-thienyl, 3-thienyl group and the like, as those of the substituent groups include an alkyl group, an alkoxy group, a dialkylamino group, hydroxy group, or a halogen atom and the like, in the L 3 As the substituent,
Examples thereof include an alkyl group, an amino group, and a halogen atom.
【0058】又、ピリリウム系、及びチアピリリウム系
色素カチオンとしては、特に、下記一般式(VIIIa) 、(V
IIIb) 、又は(VIIIc) で表されるものが好ましい。The pyrylium-based and thiapyrylium-based dye cations include, particularly, the following general formulas (VIIIa) and (V).
Those represented by IIIb) or (VIIIc) are preferred.
【0059】[0059]
【化18】 Embedded image
【0060】〔式(VIIIa) 、(VIIIb) 、及び(VIIIc)
中、Z1 及びZ2 は各々独立して、酸素原子又は硫黄原
子を示し、R11、R12、R13、及びR14は各々独立し
て、水素原子又はアルキル基、又は、R11とR13、及び
R12とR14が互いに連結して炭素数5又は6のシクロア
ルケン環を形成していてもよく、L4 は置換基を有して
いてもよいモノ、トリ、ペンタ、又はヘプタメチン基を
示し、該トリ、ペンタ、又はヘプタメチン基上の2つの
置換基が互いに連結して炭素数4〜7のシクロアルケン
環、シクロアルケノン環、シクロアルケンジオン環、又
はシクロアルケンチオン環を形成していてもよく、ピリ
リウム環及びチアピリリウム環は置換基を有していても
よく、その場合、隣接する2つの置換基が互いに連結し
て縮合ベンゼン環を形成していてもよい。〕[Formulas (VIIIa), (VIIIb) and (VIIIc)
Wherein Z 1 and Z 2 each independently represent an oxygen atom or a sulfur atom, and R 11 , R 12 , R 13 , and R 14 each independently represent a hydrogen atom or an alkyl group, or R 11 R 13 , and R 12 and R 14 may be linked to each other to form a cycloalkene ring having 5 or 6 carbon atoms, and L 4 may be mono, tri, penta, or A heptamethine group, wherein two substituents on the tri, penta, or heptamethine group are linked to each other to form a cycloalkene ring, cycloalkenone ring, cycloalkenedione ring, or cycloalkenethione ring having 4 to 7 carbon atoms And the pyrylium ring and the thiapyrylium ring may have a substituent. In this case, two adjacent substituents may be connected to each other to form a fused benzene ring. ]
【0061】ここで、式(VIIIa) 、(VIIIb) 、及び(VII
Ic) 中のR11、R12、R13、及びR 14がアルキル基であ
るときの炭素数は通常1〜15、好ましくは1〜5であ
り、L4 における置換基としては、アルキル基、アミノ
基、又はハロゲン原子等が挙げられ、ピリリウム環及び
チアピリリウム環における置換基としては、フェニル
基、ナフチル基等のアリール基等が挙げられる。Here, the formulas (VIIIa), (VIIIb) and (VII
R in Ic)11, R12, R13, And R 14Is an alkyl group
The number of carbon atoms is usually 1 to 15, preferably 1 to 5.
LFourExamples of the substituent for are an alkyl group and an amino
Group, or a halogen atom, and the like, and a pyrylium ring and
As a substituent on the thiapyrylium ring, phenyl
And aryl groups such as a naphthyl group.
【0062】以上、前記一般式(Va 〜c)で表されるキノ
リン系色素カチオン、前記一般式(VI)で表されるインド
ール系又はベンゾチアゾール系色素カチオン、前記一般
式(VII) で表されるイミノシクロヘキサジエン系色素カ
チオン、及び前記一般式(VIIIa〜c)で表されるピリリウ
ム系又はチアピリリウム系色素カチオンの中で、本発明
においては、前記一般式(VI)で表されるインドール系又
はベンゾチアゾール系色素カチオンが特に好ましい。こ
れら各シアニン系色素カチオンの具体例を以下に示す。As described above, the quinoline-based dye cation represented by the general formula (Va to c), the indole-based or benzothiazole-based dye cation represented by the general formula (VI), and the general formula (VII) Among the iminocyclohexadiene-based dye cations, and the pyrylium-based or thiapyrylium-based dye cations represented by the general formulas (VIIIa to c), in the present invention, the indole-based dye represented by the general formula (VI) or Benzothiazole dye cations are particularly preferred. Specific examples of each of these cyanine dye cations are shown below.
【0063】[0063]
【化19】 Embedded image
【0064】[0064]
【化20】 Embedded image
【0065】[0065]
【化21】 Embedded image
【0066】[0066]
【化22】 Embedded image
【0067】[0067]
【化23】 Embedded image
【0068】[0068]
【化24】 Embedded image
【0069】[0069]
【化25】 Embedded image
【0070】[0070]
【化26】 Embedded image
【0071】[0071]
【化27】 Embedded image
【0072】本発明における光重合性組成物を構成する
(B−2)成分の有機硼素アニオンとしては、例えば、
特開昭62−143044号、特開昭62−15024
2号、特開平9−188685号、特開平9−1886
86号、特開平9−188710号、特許第27647
69号等の各公報、及び、Kunz,Martin “Rad Tech'98.
Proceeding April 19-22,1998,Chicago ”等に記載のも
のが挙げられるが、特に、下記一般式(IX)で表されるも
のが好ましい。Examples of the organic boron anion of the component (B-2) constituting the photopolymerizable composition according to the present invention include, for example,
JP-A-62-143044, JP-A-62-15024
No. 2, JP-A-9-188865, JP-A-9-1886
No. 86, JP-A-9-188710, and Japanese Patent No. 27647
No. 69 etc., and Kunz, Martin “Rad Tech'98.
Proceeding April 19-22, 1998, Chicago "and the like, and particularly preferably those represented by the following general formula (IX).
【0073】[0073]
【化28】 Embedded image
【0074】〔式(IX)中、R15、R16、R17、及びR18
は各々独立して、置換基を有していてもよいアルキル
基、置換基を有していてもよいアルケニル基、置換基を
有していてもよいアルキニル基、置換基を有していても
よいアリール基、又は複素環基を示し、これらは互いに
連結して環状構造を形成していてもよく、これらのうち
少なくとも一つは置換基を有していてもよいアルキル基
である。〕[In the formula (IX), R 15 , R 16 , R 17 and R 18
Are each independently an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, A good aryl group or a heterocyclic group is shown, which may be linked to each other to form a cyclic structure, and at least one of them is an alkyl group which may have a substituent. ]
【0075】ここで、式(IX)中のR15、R16、R17、及
びR18がアルキル基であるときの炭素数は通常1〜1
5、好ましくは1〜5、アルケニル基、アルキニル基で
あるときの炭素数は通常2〜15、好ましくは2〜5、
アリール基であるときの炭素数は通常6〜20、好まし
くは6〜15、複素環基であるときの炭素数は通常4〜
20、好ましくは4〜15であり、それらにおける置換
基としては、ハロゲン原子、アルキル基、アルコキシ
基、トリフルオロメチル基、トリメチルシリル基等が挙
げられる。Here, when R 15 , R 16 , R 17 and R 18 in the formula (IX) are alkyl groups, the number of carbon atoms is usually from 1 to 1.
5, preferably 1 to 5, the number of carbon atoms when it is an alkenyl group or an alkynyl group is usually 2 to 15, preferably 2 to 5,
When it is an aryl group, it usually has 6 to 20, preferably 6 to 15, and when it is a heterocyclic group, it usually has 4 to 4 carbon atoms.
20, preferably 4 to 15, and examples of the substituent therefor include a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, and a trimethylsilyl group.
【0076】これらの有機硼素アニオンとしては、具体
的には、例えば、n−ブチル−メチル−ジフェニル硼素
アニオン、n−ブチル−トリフェニル硼素アニオン、n
−ブチル−トリス(2,4,6−トリメチルフェニル)
硼素アニオン、n−ブチル−トリス(p−メトキシフェ
ニル)硼素アニオン、n−ブチル−トリス(p−フルオ
ロフェニル)硼素アニオン、n−ブチル−トリス(m−
フルオロフェニル)硼素アニオン、n−ブチル−トリス
(2,6−ジフルオロフェニル)硼素アニオン、n−ブ
チル−トリス(2,4,6−トリフルオロフェニル)硼
素アニオン、n−ブチル−トリス(2,3,4,5,6
−ペンタフルオロフェニル)硼素アニオン、n−ブチル
−トリス(p−クロロフェニル)硼素アニオン、n−ブ
チル−トリス(トリフルオロメチル)硼素アニオン、n
−ブチル−トリス(2,6−ジフルオロ−3−ピロリル
フェニル)−硼素アニオン等が挙げられる。Specific examples of these organic boron anions include, for example, n-butyl-methyl-diphenylboron, n-butyl-triphenylboron,
-Butyl-tris (2,4,6-trimethylphenyl)
Boron anion, n-butyl-tris (p-methoxyphenyl) boron anion, n-butyl-tris (p-fluorophenyl) boron anion, n-butyl-tris (m-
Fluorophenyl) boron anion, n-butyl-tris (2,6-difluorophenyl) boron anion, n-butyl-tris (2,4,6-trifluorophenyl) boron anion, n-butyl-tris (2,3 , 4,5,6
-Pentafluorophenyl) boron anion, n-butyl-tris (p-chlorophenyl) boron anion, n-butyl-tris (trifluoromethyl) boron anion, n
-Butyl-tris (2,6-difluoro-3-pyrrolylphenyl) -boron anion;
【0077】本発明において、前記(B−1)成分のシ
アニン系色素カチオンと前記(B−2)成分の有機硼素
アニオンを光重合性組成物中に存在させるには、前記シ
アニン系色素カチオンと前記有機硼素アニオンとの塩を
配合する方法、又は、前記シアニン系色素カチオンと適
宜選択した対アニオンとの塩と、前記有機硼素アニオン
と適宜選択した対カチオンとの塩とを配合する方法等に
よる。In the present invention, in order for the cyanine dye cation of the component (B-1) and the organic boron anion of the component (B-2) to be present in the photopolymerizable composition, the cyanine dye cation must be A method of compounding a salt with the organic boron anion, or a method of compounding a salt of the cyanine dye cation with an appropriately selected counter anion and a salt of the organic boron anion and a salt of an appropriately selected counter cation, etc. .
【0078】ここで、対アニオンとしては、例えば、C
l- 、Br- 、I- 、ClO4 - 、PF6 - 、及び、B
F4 - 、BCl4 - 等の無機硼素アニオン等の無機酸ア
ニオン、ベンゼンスルホン酸、p−トルエンスルホン
酸、ナフタレンスルホン酸、酢酸等の有機酸アニオンを
挙げることができる。Here, as the counter anion, for example, C
l -, Br -, I - , ClO 4 -, PF 6 -, and, B
Examples thereof include inorganic acid anions such as inorganic boron anions such as F 4 − and BCl 4 − and organic acid anions such as benzenesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid, and acetic acid.
【0079】又、対カチオンとしては、例えば、アルカ
リ金属カチオン、アンモニウムカチオン、ホスホニウム
カチオン、スルホニウムカチオン、ヨードニウムカチオ
ン等のオニウム化合物、及び、ピリリウムカチオン、チ
アピリリウムカチオン、インドリウムカチオン等を挙げ
ることができるが、テトラアルキルアンモニウム等の有
機アンモニウムカチオンが好ましい。Examples of counter cations include onium compounds such as alkali metal cations, ammonium cations, phosphonium cations, sulfonium cations, iodonium cations, and pyrylium cations, thiapyrylium cations, and indolium cations. However, organic ammonium cations such as tetraalkylammonium are preferred.
【0080】又、(B)成分における、有機硼素アニオ
ン以外の対アニオンとしては、(B−1)成分の対アニ
オンとして挙げたものでもよいが、前記一般式(Va 〜
c)、(VI)、(VII) 、及び(VIIIa〜c)におけるL1 、
L2 、L3 、及びL4 のポリメチン鎖の置換基として、
下記一般式(X) で表されるバルビツル酸アニオン基又は
チオバルビツル酸アニオン基を有して分子内塩を形成し
ているものが好ましい。The counter anion other than the organoboron anion in the component (B) may be the same as the counter anion of the component (B-1).
c), (VI), (VII), and L 1 in (VIIIa-c),
As a substituent of the polymethine chain of L 2 , L 3 and L 4 ,
Those having a barbiturate anion group or a thiobarbiturate anion group represented by the following general formula (X) and forming an inner salt are preferable.
【0081】[0081]
【化29】 Embedded image
【0082】〔式(X) 中、Z3 は酸素原子又は硫黄原子
を示し、R19及びR20は各々独立して、水素原子、置換
基を有していてもよいアルキル基、置換基を有していて
もよいアルケニル基、置換基を有していてもよいアルコ
キシ基、又は置換基を有していてもよいフェニル基を示
す。〕[In the formula (X), Z 3 represents an oxygen atom or a sulfur atom, and R 19 and R 20 each independently represent a hydrogen atom, an alkyl group which may have a substituent, It represents an alkenyl group which may have, an alkoxy group which may have a substituent, or a phenyl group which may have a substituent. ]
【0083】ここで、式(X) 中のR19及びR20がアルキ
ル基、アルコキシ基であるときの炭素数は通常1〜1
5、好ましくは1〜5、アルケニル基であるときの炭素
数は通常2〜15、好ましくは2〜5であるが、アルキ
ル基であるのが好ましく、そのアルキル基として具体的
には、メチル基、エチル基、プロピル基、又はブチル基
等が挙げられる。Here, when R 19 and R 20 in the formula (X) are an alkyl group or an alkoxy group, the number of carbon atoms is usually 1 to 1
5, preferably 1 to 5, the number of carbon atoms when it is an alkenyl group is usually 2 to 15, preferably 2 to 5, and is preferably an alkyl group, and as the alkyl group, specifically, a methyl group , An ethyl group, a propyl group, or a butyl group.
【0084】又、(B)成分における、有機硼素アニオ
ン以外の対アニオンとして、前記一般式(Va 〜c)、(V
I)、(VII) 、及び(VIIIa〜c)におけるL1 、L2 、
L3 、及びL4 のポリメチン鎖中に、下記一般式(XI)で
表されるスクアリリックアシドアニオン基又はチオスク
アリリックアシドアニオン基、クロコニックアシドアニ
オン基又はチオクロコニックアシドアニオン基を形成し
て分子内塩を形成しているものも好ましい。As the counter anion other than the organic boron anion in the component (B), the above-mentioned general formulas (Va to c) and (V
L 1 , L 2 in (I), (VII) and (VIIIa-c)
In the polymethine chains of L 3 and L 4, a squarylic acid anion group or a thiosquaric acid anion group, a croconic acid anion group or a thiocroconic acid anion group represented by the following general formula (XI) is formed. What forms an intramolecular salt is also preferable.
【0085】[0085]
【化30】 Embedded image
【0086】〔式(XI)中、Z4 、Z5 、Z6 、Z7 、及
びZ8 は各々独立して、酸素原子又は硫黄原子を示
す。〕[In the formula (XI), Z 4 , Z 5 , Z 6 , Z 7 and Z 8 each independently represent an oxygen atom or a sulfur atom. ]
【0087】本発明において、(C)成分のハロメチル
基含有化合物は、(B)成分の前記シアニン系色素との
共存下で光照射されたときに、活性ラジカルを発生する
ラジカル発生剤であって、少なくとも一つのモノ、ジ、
又はトリハロゲン置換メチル基がs−トリアジン環に結
合したs−トリアジン化合物が好ましく、下記一般式(X
II) で表されるものが特に好ましい。In the present invention, the halomethyl group-containing compound as the component (C) is a radical generator which generates an active radical when irradiated with light in the presence of the component (B) and the cyanine dye. , At least one thing, di,
Alternatively, an s-triazine compound in which a trihalogen-substituted methyl group is bonded to an s-triazine ring is preferable, and is represented by the following general formula (X
Those represented by II) are particularly preferred.
【0088】[0088]
【化31】 Embedded image
【0089】〔式(XII) 中、Xはハロゲン原子を示し、
Wは置換基を有していてもよいアリール基又は複素環基
を示し、R21は水素原子、ハロゲン原子、アルキル基、
又はアリール基を示し、rは0〜2の整数である。〕[In the formula (XII), X represents a halogen atom,
W represents an aryl group or a heterocyclic group which may have a substituent, and R 21 represents a hydrogen atom, a halogen atom, an alkyl group,
Or an aryl group, and r is an integer of 0-2. ]
【0090】これらのs−トリアジン化合物としては、
具体的には、例えば、2−メチル−4,6−ビス(トリ
クロロメチル)−s−トリアジン、2−n−プロピル−
4,6−ビス(トリクロロメチル)−s−トリアジン、
2−(α,α,β−トリクロロエチル)−4,6−ビス
(トリクロロメチル)−s−トリアジン、2−フェニル
−4,6−ビス(トリクロロメチル)−s−トリアジ
ン、2−(p−メトキシフェニル)−4,6−ビス(ト
リクロロメチル)−s−トリアジン、2−(3,4−エ
ポキシフェニル)−4,6−ビス(トリクロロメチル)
−s−トリアジン、2−(p−クロロフェニル)−4,
6−ビス(トリクロロメチル)−s−トリアジン、2−
〔1−(p−メトキシフェニル)−2,4−ブタジエニ
ル〕−4,6−ビス(トリクロロメチル)−s−トリア
ジン、2−スチリル−4,6−ビス(トリクロロメチ
ル)−s−トリアジン、2−(p−メトキシスチリル)
−4,6−ビス(トリクロロメチル)−s−トリアジ
ン、2−(p−i−プロピルオキシスチリル)−4,6
−ビス(トリクロロメチル)−s−トリアジン、2−
(p−トリル)−4,6−ビス(トリクロロメチル)−
s−トリアジン、2−(4−メトキシナフチル)−4,
6−ビス(トリクロロメチル)−s−トリアジン、2−
フェニルチオ−4,6−ビス(トリクロロメチル)−s
−トリアジン、2−ベンジルチオ−4,6−ビス(トリ
クロロメチル)−s−トリアジン、2−メチル−4,6
−ビス(トリブロモメチル)−s−トリアジン、2−メ
トキシ−4,6−ビス(トリブロモメチル)−s−トリ
アジン等が挙げられ、中でも、2−メチル−4,6−ビ
ス(トリクロロメチル)−s−トリアジン、2−フェニ
ル−4,6−ビス(トリクロロメチル)−s−トリアジ
ン、2−(p−メトキシフェニル)−4,6−ビス(ト
リクロロメチル)−s−トリアジン、2−(3,4−エ
ポキシフェニル)−4,6−ビス(トリクロロメチル)
−s−トリアジン、2−〔1−(p−メトキシフェニ
ル)−2,4−ブタジエニル〕−4,6−ビス(トリク
ロロメチル)−s−トリアジン、2−(p−メトキシス
チリル)−4,6−ビス(トリクロロメチル)−s−ト
リアジン、2−(p−i−プロピルオキシスチリル)−
4,6−ビス(トリクロロメチル)−s−トリアジン等
が経時安定性に優れ好ましい。These s-triazine compounds include:
Specifically, for example, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2-n-propyl-
4,6-bis (trichloromethyl) -s-triazine,
2- (α, α, β-trichloroethyl) -4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p- Methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (3,4-epoxyphenyl) -4,6-bis (trichloromethyl)
-S-triazine, 2- (p-chlorophenyl) -4,
6-bis (trichloromethyl) -s-triazine, 2-
[1- (p-methoxyphenyl) -2,4-butadienyl] -4,6-bis (trichloromethyl) -s-triazine, 2-styryl-4,6-bis (trichloromethyl) -s-triazine, -(P-methoxystyryl)
-4,6-bis (trichloromethyl) -s-triazine, 2- (pi-propyloxystyryl) -4,6
-Bis (trichloromethyl) -s-triazine, 2-
(P-tolyl) -4,6-bis (trichloromethyl)-
s-triazine, 2- (4-methoxynaphthyl) -4,
6-bis (trichloromethyl) -s-triazine, 2-
Phenylthio-4,6-bis (trichloromethyl) -s
-Triazine, 2-benzylthio-4,6-bis (trichloromethyl) -s-triazine, 2-methyl-4,6
-Bis (tribromomethyl) -s-triazine, 2-methoxy-4,6-bis (tribromomethyl) -s-triazine and the like, among which 2-methyl-4,6-bis (trichloromethyl) -S-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (3 , 4-Epoxyphenyl) -4,6-bis (trichloromethyl)
-S-triazine, 2- [1- (p-methoxyphenyl) -2,4-butadienyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxystyryl) -4,6 -Bis (trichloromethyl) -s-triazine, 2- (pi-propyloxystyryl)-
4,6-bis (trichloromethyl) -s-triazine and the like are preferable because of excellent stability over time.
【0091】本発明における光重合性組成物は、前記
(A)成分のエチレン性不飽和化合物と前記(B−1)
成分のシアニン系色素カチオンと前記(B−2)成分の
有機硼素アニオンとを含有するか、又は、前記(A)成
分のエチレン系不飽和化合物と前記(B)成分のシアニ
ン系色素と前記(C)成分のハロメチル基含有化合物と
を含有するが、前記(A)成分の光重合性組成物全体に
占める割合は、後述する他の成分の含有もあって、20
〜80重量%であるのが好ましく、30〜70重量%で
あるのが特に好ましい。The photopolymerizable composition of the present invention comprises the component (A) of the ethylenically unsaturated compound and the component (B-1).
It contains the cyanine dye cation of the component and the organic boron anion of the component (B-2), or the ethylenically unsaturated compound of the component (A), the cyanine dye of the component (B), and the ( Component (C) and the compound containing a halomethyl group, the proportion of the component (A) in the entire photopolymerizable composition is 20% due to the inclusion of other components described later.
It is preferably from 80 to 80% by weight, particularly preferably from 30 to 70% by weight.
【0092】又、前記(B−1)成分と(B−2)成分
との合計量の光重合性組成物全体に占める割合は、0.
05〜20重量%であるのが好ましく、0.2〜10重
量%であるのが更に好ましい。これらの成分が前記範囲
未満では、光重合性画像形成材として感度の低下を生じ
る傾向となり、前記範囲超過では、現像時に未露光部の
残渣が生じ易い傾向となる。The ratio of the total amount of the components (B-1) and (B-2) to the whole photopolymerizable composition is 0.1%.
It is preferably from 0.5 to 20% by weight, more preferably from 0.2 to 10% by weight. When these components are less than the above ranges, the sensitivity tends to decrease as a photopolymerizable image-forming material, and when the components exceed the above ranges, residues in unexposed areas tend to be easily generated during development.
【0093】又、前記(B)成分の光重合性組成物全体
に占める割合、及び、前記(C)成分の光重合性組成物
全体に占める割合は、各々、0.05〜20重量%であ
るのが好ましく、0.2〜10重量%であるのが更に好
ましい。これらの成分が前記範囲未満では、光重合性画
像形成材として感度の低下を生じる傾向となり、前記範
囲超過では、現像時に未露光部の残渣が生じ易い傾向と
なる。The ratio of the component (B) to the whole photopolymerizable composition and the ratio of the component (C) to the whole photopolymerizable composition are each 0.05 to 20% by weight. Preferably, it is 0.2 to 10% by weight. When these components are less than the above ranges, the sensitivity tends to decrease as a photopolymerizable image-forming material, and when the components exceed the above ranges, residues in unexposed areas tend to be easily generated during development.
【0094】尚、本発明における光重合性組成物には、
前記成分以外に、例えば、(メタ)アクリル酸、(メ
タ)アクリル酸エステル、(メタ)アクリロニトリル、
(メタ)アクリルアミド、マレイン酸、スチレン、酢酸
ビニル、塩化ビニリデン、マレイミド等の単独又は共重
合体、並びに、ポリアミド、ポリエステル、ポリエーテ
ル、ポリウレタン、ポリビニルブチラール、ポリビニル
ピロリドン、ポリエチレンオキシド、アセチルセルロー
ス等の有機高分子が結合材(D)成分として、光重合性
組成物全体に占める割合として20〜80重量%、特に
は30〜70重量%の範囲で含有されているのが好まし
い。Incidentally, the photopolymerizable composition of the present invention includes:
In addition to the above components, for example, (meth) acrylic acid, (meth) acrylate, (meth) acrylonitrile,
Homo- or copolymers such as (meth) acrylamide, maleic acid, styrene, vinyl acetate, vinylidene chloride, and maleimide; and organic materials such as polyamide, polyester, polyether, polyurethane, polyvinyl butyral, polyvinyl pyrrolidone, polyethylene oxide, and acetyl cellulose. It is preferable that the polymer is contained as the binder (D) component in the range of 20 to 80% by weight, particularly 30 to 70% by weight, based on the entire photopolymerizable composition.
【0095】本発明において、(D)成分の前記有機高
分子結合材としては、カルボキシル基含有重合体が好適
であり、具体的には、(メタ)アクリル酸と(メタ)ア
クリル酸エステルとの共重合体が好ましく、このカルボ
キシル基含有重合体の酸価は10〜250、重量平均分
子量は0.5〜50万であるのが好ましい。In the present invention, as the organic polymer binder of the component (D), a carboxyl group-containing polymer is preferable. Specifically, a polymer of (meth) acrylic acid and (meth) acrylic acid ester is used. A copolymer is preferable, and the acid value of the carboxyl group-containing polymer is preferably 10 to 250, and the weight average molecular weight is preferably 0.5 to 500,000.
【0096】更に、本発明における高分子結合材は、側
鎖にエチレン性不飽和結合を有するものであるのが好適
であり、そのエチレン性不飽和結合として、特に、下記
一般式(XIIIa) 、(XIIIb) 、及び(XIIIc) で表されるも
のが好ましい。Further, the polymer binder in the present invention is preferably one having an ethylenically unsaturated bond in a side chain. As the ethylenically unsaturated bond, the following general formula (XIIIa): Those represented by (XIIIb) and (XIIIc) are preferred.
【0097】[0097]
【化32】 Embedded image
【0098】〔式(XIIIa) 、(XIIIb) 、及び(XIIIc)
中、R0 は水素原子又はメチル基を示し、R22〜R26は
各々独立して、水素原子、ハロゲン原子、アミノ基、ジ
アルキルアミノ基、カルボキシル基、アルコキシカルボ
ニル基、スルホ基、ニトロ基、シアノ基、置換基を有し
ていてもよいアルキル基、置換基を有していてもよいア
リール基、置換基を有していてもよいアルコキシ基、置
換基を有していてもよいアリールオキシ基、置換基を有
していてもよいアルキルアミノ基、置換基を有していて
もよいアリールアミノ基、置換基を有していてもよいア
ルキルスルホニル基、又は置換基を有していてもよいア
リールスルホニル基を示し、Aは酸素原子、硫黄原子、
イミノ基、又はアルキルイミノ基を示す。〕[Formulas (XIIIa), (XIIIb) and (XIIIc)
Wherein R 0 represents a hydrogen atom or a methyl group, and R 22 to R 26 each independently represent a hydrogen atom, a halogen atom, an amino group, a dialkylamino group, a carboxyl group, an alkoxycarbonyl group, a sulfo group, a nitro group, A cyano group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, and an aryloxy which may have a substituent Group, an alkylamino group which may have a substituent, an arylamino group which may have a substituent, an alkylsulfonyl group which may have a substituent, or a group which has a substituent A good arylsulfonyl group, wherein A is an oxygen atom, a sulfur atom,
It represents an imino group or an alkylimino group. ]
【0099】前記一般式(XIIIa) で表されるエチレン性
不飽和結合を側鎖に有する高分子結合材は、カルボキシ
ル基含有重合体に、アリルグリシジルエーテル、グリシ
ジル(メタ)アクリレート、α−エチルグリシジル(メ
タ)アクリレート、グリシジルクロトネート、グリシジ
ルイソクロトネート、クロトニルグリシジルエーテル、
イタコン酸モノアルキルモノグリシジルエステル、フマ
ール酸モノアルキルモノグリシジルエステル、マレイン
酸モノアルキルモノグリシジルエステル等の脂肪族エポ
キシ基含有不飽和化合物、及び、特開平1−28982
0号公報に開示されるような、例えば、3,4−エポキ
シシクロヘキシルメチル(メタ)アクリレート等の脂環
式エポキシ基含有不飽和化合物等を、80〜120℃程
度の温度、1〜50時間程度の時間で、カルボキシル基
含有重合体の有するカルボキシル基の5〜90モル%、
好ましくは30〜70モル%程度を反応させることによ
り製造される。The polymer binder having an ethylenically unsaturated bond in the side chain represented by the general formula (XIIIa) is obtained by adding carboxyl group-containing polymer to allyl glycidyl ether, glycidyl (meth) acrylate, α-ethyl glycidyl. (Meth) acrylate, glycidyl crotonate, glycidyl isocrotonate, crotonyl glycidyl ether,
Aliphatic epoxy group-containing unsaturated compounds such as monoalkyl monoglycidyl itaconate, monoalkyl monoglycidyl fumarate and monoalkyl monoglycidyl maleate; and JP-A-1-28982
No. 0, for example, an alicyclic epoxy group-containing unsaturated compound such as 3,4-epoxycyclohexylmethyl (meth) acrylate or the like, at a temperature of about 80 to 120 ° C. for about 1 to 50 hours. In the time of 5 to 90 mol% of the carboxyl group of the carboxyl group-containing polymer,
It is preferably produced by reacting about 30 to 70 mol%.
【0100】又、前記一般式(XIIIb) で表されるエチレ
ン性不飽和結合を側鎖に有する高分子結合材は、アリル
(メタ)アクリレート、3−アリルオキシ−2−ヒドロ
キシプロピル(メタ)アクリレート、シンナミル(メ
タ)アクリレート、クロトニル(メタ)アクリレート、
メタリル(メタ)アクリレート、N,N−ジアリル(メ
タ)アクリルアミド等の2種以上の不飽和基を有する化
合物と、又、前記一般式(XIIIc) で表されるエチレン性
不飽和結合を側鎖に有する高分子結合材は、ビニル(メ
タ)アクリレート、1−クロロビニル(メタ)アクリレ
ート、2−フェニルビニル(メタ)アクリレート、1−
プロペニル(メタ)アクリレート、ビニルクロトネー
ト、ビニル(メタ)アクリルアミド等の2種以上の不飽
和基を有する化合物と、それぞれ、(メタ)アクリル酸
等の不飽和カルボン酸、又は更に不飽和カルボン酸エス
テルとを、前者の不飽和基を有する化合物の全体に占め
る割合を10〜90モル%、好ましくは30〜80モル
%程度となるように共重合させることにより製造され
る。The polymer binder having an ethylenically unsaturated bond represented by the general formula (XIIIb) in the side chain includes allyl (meth) acrylate, 3-allyloxy-2-hydroxypropyl (meth) acrylate, Cinnamyl (meth) acrylate, crotonyl (meth) acrylate,
A compound having two or more kinds of unsaturated groups such as methallyl (meth) acrylate and N, N-diallyl (meth) acrylamide; and an ethylenically unsaturated bond represented by the above general formula (XIIIc) in a side chain. The polymer binder has vinyl (meth) acrylate, 1-chlorovinyl (meth) acrylate, 2-phenylvinyl (meth) acrylate, 1-
Compounds having two or more types of unsaturated groups such as propenyl (meth) acrylate, vinyl crotonate, vinyl (meth) acrylamide, and unsaturated carboxylic acids such as (meth) acrylic acid or further unsaturated carboxylic acid esters, respectively Is copolymerized so that the ratio of the former compound having an unsaturated group to the whole is 10 to 90 mol%, preferably about 30 to 80 mol%.
【0101】又、本発明における光重合性組成物には、
必要に応じて、その他(E)成分として、(1) 前記(B
−1)成分と(B−2)成分、或いは、前記(B)成分
と(C)成分とからなる光重合開始剤系以外の重合開始
剤として、例えば、特開昭58−29803号公報等に
記載されるチオール化合物、及び、ジアルキルアミノ安
息香酸アルキルエステル、ビスアミノベンゾフェノン、
ビスアミノベンジル等のアミン化合物、並びに、本願出
願人による特願平10−157177号明細書に記載さ
れる脂肪族アミノ酸エステル及びその誘導体、(2) 有機
又は無機の染顔料からなる着色剤、(3) トリアリールメ
タン、ビスアリールメタン、キサンテン化合物、フルオ
ラン化合物、チアジン化合物、並びに、その部分骨格と
してラクトン、ラクタム、スルトン、スピロピラン構造
を形成させた化合物等の色素ロイコ体等の色素前駆体、
(4) ジオクチルフタレート、ジドデシルフタレート、ト
リクレジルホスフェート、ジオクチルアジペート、トリ
エチレングリコールジカプリレート等の可塑剤、(5) 三
級アミン、チオール等の感度改善剤、(6) ヒドロキノ
ン、レゾルシノール、ピロガロール、p−メトキシフェ
ノール、2,6−ジ−t−ブチル−p−クレゾール、β
−ナフトール等の熱重合防止剤、等が添加されていても
よい。The photopolymerizable composition of the present invention includes:
If necessary, as the other component (E), (1) the above (B)
Examples of the polymerization initiator other than the photopolymerization initiator system comprising the component -1) and the component (B-2) or the component (B) and the component (C) include, for example, JP-A-58-29803. A thiol compound, and a dialkylaminobenzoic acid alkyl ester, bisaminobenzophenone,
Amine compounds such as bisaminobenzyl, and aliphatic amino acid esters and their derivatives described in Japanese Patent Application No. 10-157177 filed by the present applicant; (2) a colorant comprising an organic or inorganic dye / pigment; 3) triarylmethane, bisarylmethane, xanthene compound, fluoran compound, thiazine compound, and a dye precursor such as dye leuco such as lactone, lactam, sultone, and a compound having a spiropyran structure as a partial skeleton thereof,
(4) plasticizers such as dioctyl phthalate, didodecyl phthalate, tricresyl phosphate, dioctyl adipate, triethylene glycol dicaprylate, (5) sensitivity improvers such as tertiary amines and thiols, (6) hydroquinone, resorcinol, Pyrogallol, p-methoxyphenol, 2,6-di-t-butyl-p-cresol, β
-A thermal polymerization inhibitor such as naphthol may be added.
【0102】本発明の光重合性画像形成材は、好ましく
は、前記光重合性組成物の各成分を適当な溶媒に溶解し
た溶液として前記支持体表面に塗布した後、加熱、乾燥
させて、前記支持体表面に前記光重合性組成物の層を形
成させることにより製造される。The photopolymerizable image-forming material of the present invention is preferably applied to the surface of the support as a solution in which each component of the photopolymerizable composition is dissolved in an appropriate solvent, and then heated and dried. It is manufactured by forming a layer of the photopolymerizable composition on the surface of the support.
【0103】ここで、その溶媒としては、使用成分に対
して十分な溶解度を持ち、良好な塗膜性を与えるもので
あれば特に制限はないが、例えば、メチルセロソルブ、
エチルセロソルブ、メチルセロソルブアセテート、エチ
ルセロソルブアセテート等のセロソルブ系溶媒、プロピ
レングリコールモノメチルエーテル、プロピレングリコ
ールモノエチルエーテル、プロピレングリコールモノブ
チルエーテル、プロピレングリコールモノメチルエーテ
ルアセテート、プロピレングリコールモノエチルエーテ
ルアセテート、プロピレングリコールモノブチルエーテ
ルアセテート、ジプロピレングリコールジメチルエーテ
ル等のプロピレングリコール系溶媒、酢酸ブチル、酢酸
アミル、酪酸エチル、酪酸ブチル、ジエチルオキサレー
ト、ピルビン酸エチル、エチル−2−ヒドロキシブチレ
ート、エチルアセトアセテート、乳酸メチル、乳酸エチ
ル、3−メトキシプロピオン酸メチル等のエステル系溶
媒、ヘプタノール、ヘキサノール、ジアセトンアルコー
ル、フルフリルアルコール等のアルコール系溶媒、シク
ロヘキサノン、メチルアミルケトン等のケトン系溶媒、
ジメチルホルムアミド、ジメチルアセトアミド、N−メ
チルピロリドン等の高極性溶媒、或いはこれらの混合溶
媒、更にはこれらに芳香族炭化水素を添加したもの等が
挙げられる。溶媒の使用割合は、光重合性組成物の総量
に対して、通常、重量比で1〜20倍程度の範囲であ
る。Here, the solvent is not particularly limited as long as it has a sufficient solubility for the components used and gives good coating properties. Examples of the solvent include methyl cellosolve,
Cellosolve solvents such as ethyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate , Propylene glycol solvents such as dipropylene glycol dimethyl ether, butyl acetate, amyl acetate, ethyl butyrate, butyl butyrate, diethyl oxalate, ethyl pyruvate, ethyl-2-hydroxybutyrate, ethyl acetoacetate, methyl lactate, ethyl lactate, Ester solvents such as methyl 3-methoxypropionate, heptanol Hexanol, diacetone alcohol, alcohol solvents such as furfuryl alcohol, cyclohexanone, ketone solvents such as methyl amyl ketone,
Highly polar solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like, or a mixed solvent thereof, and further a mixture thereof with an aromatic hydrocarbon may be used. The usage ratio of the solvent is usually in the range of about 1 to 20 times by weight based on the total amount of the photopolymerizable composition.
【0104】又、その塗布方法としては、従来公知の方
法、例えば、回転塗布、ワイヤーバー塗布、ディップ塗
布、エアーナイフ塗布、ロール塗布、ブレード塗布、及
びカーテン塗布等を用いることができる。塗布量は用途
により異なるが、乾燥膜厚として、通常、0.3〜7μ
m、好ましくは0.5〜5μm、特に好ましくは1〜3
μmの範囲とする。尚、その際の乾燥温度としては、例
えば、60〜170℃程度、好ましくは70〜150℃
程度、乾燥時間としては、例えば、5秒〜10分間程
度、好ましくは10秒〜5分間程度が採られる。The coating method may be a conventionally known method, for example, spin coating, wire bar coating, dip coating, air knife coating, roll coating, blade coating, curtain coating, or the like. The coating amount varies depending on the application, but is usually 0.3 to 7 μm
m, preferably 0.5-5 μm, particularly preferably 1-3
μm range. The drying temperature at that time is, for example, about 60 to 170 ° C, preferably 70 to 150 ° C.
The drying time is about 5 seconds to 10 minutes, preferably about 10 seconds to 5 minutes.
【0105】尚、通常、前記光重合性組成物層の上に
は、酸素による重合禁止作用を防止するために、ポリビ
ニルアルコール、ポリビニルピロリドン、ポリエチレン
オキシド、セルロース等の酸素遮断層が設けられる。Incidentally, an oxygen-blocking layer of polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene oxide, cellulose or the like is usually provided on the photopolymerizable composition layer in order to prevent a polymerization inhibition effect by oxygen.
【0106】本発明の光重合性画像形成材の光重合性組
成物層を画像露光する光源としては、カーボンアーク、
高圧水銀灯、キセノンランプ、メタルハライドランプ、
蛍光ランプ、タングステンランプ、ハロゲンランプ、H
eNeレーザー、アルゴンイオンレーザー、YAGレー
ザー、HeCdレーザー、半導体レーザー、ルビーレー
ザー等のレーザー光源が挙げられるが、特に、700n
m以上の近赤外線レーザー光線を発生する光源が好まし
く、例えば、ルビーレーザー、YAGレーザー、半導体
レーザー等の固体レーザーを挙げることができ、特に、
小型で長寿命な半導体レーザーやYAGレーザーが好ま
しい。これらの光源により、通常、走査露光した後、現
像液にて現像し画像が形成される。The light source for imagewise exposing the photopolymerizable composition layer of the photopolymerizable image forming material of the present invention includes carbon arc,
High-pressure mercury lamp, xenon lamp, metal halide lamp,
Fluorescent lamp, tungsten lamp, halogen lamp, H
A laser light source such as an eNe laser, an argon ion laser, a YAG laser, a HeCd laser, a semiconductor laser, and a ruby laser may be used.
m or more of a light source that generates a near infrared laser beam, for example, a ruby laser, a YAG laser, a solid-state laser such as a semiconductor laser, and in particular,
A small and long-life semiconductor laser or YAG laser is preferable. Usually, after scanning and exposure with these light sources, an image is formed by developing with a developer.
【0107】本発明の光重合性画像形成材における光重
合性組成物は、700〜1300nmの近赤外線領域の
範囲で、例えば、半導体レーザーを用いて108 W/m
2 以上の高密度光強度で露光した場合、102 W/m2
以下の低密度光強度で露光した場合に比して5倍以上、
好ましくは10倍以上の感度を示し、そして、この感度
の差により、通常の白色蛍光灯下におけるセーフライト
性(作業適性)を発現させることができる。The photopolymerizable composition in the photopolymerizable image-forming material of the present invention can be used in a near infrared region of 700 to 1300 nm, for example, by using a semiconductor laser at 10 8 W / m 2.
When exposed at a high light intensity of 2 or more, 10 2 W / m 2
5 times or more compared to the case of exposure at the following low density light intensity,
Preferably, the sensitivity is 10 times or more, and the difference in the sensitivity enables the expression of safelight property (workability) under a normal white fluorescent lamp.
【0108】本発明の前記光重合性画像形成材を画像露
光した感光体の現像に用いる現像液としては、例えば、
珪酸ナトリウム、珪酸カリウム、珪酸リチウム、珪酸ア
ンモニウム、メタ珪酸ナトリウム、メタ珪酸カリウム、
水酸化ナトリウム、水酸化カリウム、水酸化リチウム、
炭酸ナトリウム、重炭酸ナトリウム、炭酸カリウム、第
二燐酸ナトリウム、第三燐酸ナトリウム、第二燐酸アン
モニウム、第三燐酸アンモニウム、硼酸ナトリウム、硼
酸カリウム、硼酸アンモニウム等の無機アルカリ塩、モ
ノメチルアミン、ジメチルアミン、トリメチルアミン、
モノエチルアミン、ジエチルアミン、トリエチルアミ
ン、モノイソプロピルアミン、ジイソプロピルアミン、
モノブチルアミン、モノエタノールアミン、ジエタノー
ルアミン、トリエタノールアミン、モノイソプロパノー
ルアミン、ジイソプロパノールアミン等の有機アミン化
合物の0.1〜5重量%程度の水溶液からなるアルカリ
現像液を用いる。Examples of the developer used for developing the photoreceptor obtained by subjecting the photopolymerizable image forming material of the present invention to image exposure include, for example,
Sodium silicate, potassium silicate, lithium silicate, ammonium silicate, sodium metasilicate, potassium metasilicate,
Sodium hydroxide, potassium hydroxide, lithium hydroxide,
Inorganic alkali salts such as sodium carbonate, sodium bicarbonate, potassium carbonate, dibasic sodium phosphate, tertiary sodium phosphate, dibasic ammonium phosphate, tertiary ammonium phosphate, sodium borate, potassium borate and ammonium borate, monomethylamine, dimethylamine, Trimethylamine,
Monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine,
Use is made of an alkali developer consisting of an aqueous solution of an organic amine compound such as monobutylamine, monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine and the like in a concentration of about 0.1 to 5% by weight.
【0109】[0109]
【実施例】以下、本発明を実施例によりさらに具体的に
説明するが、本発明はその要旨を越えない限り、以下の
実施例に限定されるものではない。尚、以下の実施例及
び比較例において光重合性組成物の各成分には以下のも
のを用いた。EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention. In the following Examples and Comparative Examples, the following components were used for each component of the photopolymerizable composition.
【0110】(A)成分;エチレン性不飽和化合物 一般式(I) における具体例(I-1) で示した(メタ)ア
クリロイルオキシアルキル基含有ウレタン化合物 一般式(I) における具体例(I-2) で示した(メタ)ア
クリロイルオキシアルキル基含有ウレタン化合物 一般式(I) における具体例(I-3) で示した(メタ)ア
クリロイルオキシアルキル基含有ウレタン化合物 一般式(I) における具体例(I-4) で示した(メタ)ア
クリロイルオキシアルキル基含有ウレタン化合物 一般式(I) における具体例(I-8) で示した(メタ)ア
クリロイルオキシアルキル基含有ウレタン化合物 一般式(II)におけるメタアクリロイルオキシエチルホ
スフェートとビス(メタアクリロイルオキシエチル)ホ
スフェートとの1:1の混合物 一般式(III) における2,2−ビス(4−ヒドロキシ
フェニル)プロパンのアクリロイルジエチレンオキシド
付加物 一般式(IV)におけるトリス(アクリロイルオキシエチ
ル)アミン トリメチロールプロパントリアクリレートComponent (A): Ethylenically unsaturated compound (meth) acryloyloxyalkyl group-containing urethane compound represented by the specific example (I-1) in the general formula (I) Specific example (I- (Meth) acryloyloxyalkyl group-containing urethane compound shown in 2) Specific example in general formula (I) (I-3) (meth) acryloyloxyalkyl group-containing urethane compound specific example in general formula (I) ( (Meth) acryloyloxyalkyl group-containing urethane compound represented by the formula (I-4) Specific examples of the general formula (I) (I-8) (meth) acryloyloxyalkyl group-containing urethane compound represented by the general formula (II) A mixture of acryloyloxyethyl phosphate and bis (methacryloyloxyethyl) phosphate at a ratio of 1: 1 2,2-bis (4-hydroxyphenyl) in the general formula (III) Acryloyldiethylene oxide adduct of (enyl) propane tris (acryloyloxyethyl) amine in general formula (IV) trimethylolpropane triacrylate
【0111】(B−1)成分;シアニン系色素カチオン 一般式(VI)における具体例(VI-7)で示したインドール
系色素カチオン 一般式(VI)における具体例(VI-7)で示したインドール
系色素カチオンと、4フッ化硼素アニオンとの塩 (B−2)成分;有機硼素アニオン 一般式(IX)におけるn−ブチル−トリフェニル硼素ア
ニオン テトラメチルアンモニウムカチオンと一般式(IX)にお
けるn−ブチル−トリフェニル硼素アニオンとの塩 テトラメチルアンモニウムカチオンと一般式(IX)にお
けるn−ブチル−トリス(2,6−ジフルオロフェニ
ル)硼素アニオンとの塩Component (B-1): Cyanine-based dye cation Indole-based dye cation represented by specific example (VI-7) in general formula (VI) Specific example (VI-7) shown in general formula (VI) Salt of indole dye cation and boron tetrafluoride anion (B-2) component; organic boron anion n-butyl-triphenylboron anion in general formula (IX) Tetramethylammonium cation and n in general formula (IX) Salt with -butyl-triphenylboron anion Salt of tetramethylammonium cation with n-butyl-tris (2,6-difluorophenyl) boron anion in formula (IX)
【0112】(B)成分;シアニン系色素カチオンと有
機硼素アニオン以外の対アニオンとの塩 一般式(VI)における具体例(VI-5)で示したインドール
系色素カチオンと、そのシクロペンテン環に置換基とし
て、塩素原子に換えて、一般式(X) におけるZ 3 が酸素
原子、R19及びR20がメチル基であるバルビツル酸アニ
オン基を有する分子内塩のインドール系色素 一般式(VI)における具体例(VI-5)で示したインドール
系色素カチオンと、そのシクロペンテン環に置換基とし
て、塩素原子に換えて、一般式(X) におけるZ 3 が硫黄
原子、R19及びR20がメチル基であるチオバルビツル酸
アニオン基を有する分子内塩のインドール系色素 一般式(VI)における具体例(VI-7)で示したインドール
系色素カチオンと、4フッ化硼素アニオンとの塩Component (B): Cyanine dye cation and
Salts with a counter anion other than the mechanical boron anion.
And the substituent on the cyclopentene ring
In place of the chlorine atom, Z in the general formula (X) ThreeIs oxygen
Atom, R19And R20Is a methyl group
Indole dye of an inner salt having an on group.
And the substituent on the cyclopentene ring
In place of the chlorine atom, Z in the general formula (X) ThreeIs sulfur
Atom, R19And R20Is a methyl group
Indole dyes of inner salts having an anionic group.
Salt of fluorinated dye cation and boron tetrafluoride anion
【0113】(C)成分;ハロメチル基含有化合物 一般式(XII) における2−メチル−4,6−ビス(ト
リクロロメチル)−s−トリアジン 一般式(XII) における2−(p−メトキシフェニル)
−4,6−ビス(トリクロロメチル)−s−トリアジン 一般式(XII) における2−(p−メトキシスチリル)
−4,6−ビス(トリクロロメチル)−s−トリアジン 一般式(XII) における2−(4−メトキシナフチル)
−4,6−ビス(トリクロロメチル)−s−トリアジンComponent (C): Halomethyl group-containing compound 2-methyl-4,6-bis (trichloromethyl) -s-triazine in general formula (XII) 2- (p-methoxyphenyl) in general formula (XII)
-4,6-bis (trichloromethyl) -s-triazine 2- (p-methoxystyryl) in the general formula (XII)
-4,6-bis (trichloromethyl) -s-triazine 2- (4-methoxynaphthyl) in the formula (XII)
-4,6-bis (trichloromethyl) -s-triazine
【0114】(D)成分;高分子結合材 メチルメタクリレート(35モル%)/イソブチルメ
タクリレート(20モル%)/イソブチルアクリレート
(10モル%)/メタクリル酸(35モル%)共重合体
(重量平均分子量7万)に、3,4−エポキシシクロヘ
キシルメチルアクリレートを反応させて得られた反応生
成物(酸化60、メタクリル酸成分のカルボキシル基の
60モル%が反応)。 α−メチルスチレン/アクリル酸共重合体(重量平均
分子量1.5万、酸価240、Jhonson社製「S
CX−690」)に3,4−エポキシシクロヘキシルメ
チルアクリレートを反応させて得られた反応生成物(酸
化約170、アクリル酸成分のカルボキシル基の50モ
ル%が反応)。Component (D): Polymeric binder Methyl methacrylate (35 mol%) / isobutyl methacrylate (20 mol%) / isobutyl acrylate (10 mol%) / methacrylic acid (35 mol%) copolymer (weight average molecular weight) 70,000) with 3,4-epoxycyclohexylmethyl acrylate (oxidation 60, 60 mol% of the carboxyl groups of the methacrylic acid component react). α-methylstyrene / acrylic acid copolymer (weight average molecular weight 15,000, acid value 240, manufactured by Johnson “S”
A reaction product obtained by reacting 3,4-epoxycyclohexylmethyl acrylate with "CX-690") (oxidation: about 170, 50 mol% of the carboxyl groups of the acrylic acid component react).
【0115】(E)成分;その他成分(重合開始剤) N−フェニル−β−アミノプロピオン酸メチル 2,2’−ビス(o−クロロフェニル)−4,4’,
5,5’−テトラフェニルビイミダゾール ビス(ジ−t−ブチルジパーオキシフタロイル)ケト
ン ジシクロペンタジエニルチタニウムビス(2,6−ジ
フルオロ−3−(1−ピロリル)フェニル)Component (E); Other components (polymerization initiator) Methyl N-phenyl-β-aminopropionate 2,2′-bis (o-chlorophenyl) -4,4 ′,
5,5'-tetraphenylbiimidazole bis (di-t-butyldiperoxyphthaloyl) ketone dicyclopentadienyltitanium bis (2,6-difluoro-3- (1-pyrrolyl) phenyl)
【0116】実施例1〜16、比較例1〜10 厚さ0.24mmのアルミニウム板を用い、その表面
を、5重量%水酸化ナトリウム水溶液中で60℃で1分
間脱脂処理した後、0.5モル/リットルの塩酸水溶液
中で、28℃、60A/dm2 の電流密度で40秒間電
解エッチング処理し、次いで、4重量%水酸化ナトリウ
ム水溶液中で60℃で12秒間デスマット処理した後、
20重量%硫酸水溶液中で、20℃、3.5A/dm2
の電流密度で1分間陽極酸化処理し、更に、80℃の熱
水で20秒間封孔処理し、水洗、乾燥して光重合性平版
印刷版用の支持体を作製した。尚、比較例9用として、
硫酸に換えて燐酸を用いて陽極酸化処理した点のみ異な
らしめた支持体を作製した。得られた支持体につき、そ
の表面のガムテープの剥離強度を測定し、以下の基準で
評価し、結果を表1に示した。Examples 1 to 16 and Comparative Examples 1 to 10 A 0.24 mm thick aluminum plate was degreased at 60 ° C. for 1 minute in a 5% by weight aqueous sodium hydroxide solution. In a 5 mol / L hydrochloric acid aqueous solution, an electrolytic etching treatment was performed at 28 ° C. and a current density of 60 A / dm 2 for 40 seconds, and then a desmut treatment was performed in a 4% by weight aqueous sodium hydroxide solution at 60 ° C. for 12 seconds.
In a 20% by weight aqueous sulfuric acid solution, 20 ° C., 3.5 A / dm 2
At a current density of 1 minute, sealed with hot water at 80 ° C. for 20 seconds, washed with water and dried to prepare a support for a photopolymerizable lithographic printing plate. In addition, for Comparative Example 9,
A support was prepared which differed only in that it was anodized using phosphoric acid instead of sulfuric acid. The peel strength of the gum tape on the surface of the obtained support was measured and evaluated according to the following criteria. The results are shown in Table 1.
【0117】A;剥離強度が50g/cm以上、350
g/cm未満。 B;剥離強度が350g/cm以上、450g/cm未
満。 C;剥離強度が450〜500g/cm。 D;剥離強度が500g/cm超過。A: peel strength of 50 g / cm or more, 350
less than g / cm. B: Peel strength is 350 g / cm or more and less than 450 g / cm. C: Peel strength is 450 to 500 g / cm. D: Peel strength exceeds 500 g / cm.
【0118】次いで、得られたアルミニウム板支持体表
面に、表1に示す、(A)成分と、(B−1)成分と
(B−2)成分、又は、(B)成分と(C)成分の表1
に示す量と、更に、(D)成分として前記高分子結合材
35重量部と前記高分子結合材10重量部と、
(E)成分として銅フタロシアニン顔料6重量部とを、
シクロヘキサン500重量部とメチルセロソルブ500
重量部との混合溶媒に室温で10分間攪拌して調液した
塗布液をワイヤーバーを用いて塗布し、80℃で2分間
乾燥させて膜厚2μmの光重合性組成物層を形成し、更
にその上に、ポリビニルアルコール水溶液を塗布し、8
0℃で2分間乾燥させて膜厚3μmのオーバーコート層
を形成して光重合性平版印刷版を作製した。Then, the components (A), (B-1) and (B-2), or (B) and (C) shown in Table 1 were applied to the surface of the obtained aluminum plate support. Table 1 of ingredients
And 35 parts by weight of the polymer binder and 10 parts by weight of the polymer binder as component (D).
(E) 6 parts by weight of a copper phthalocyanine pigment as a component,
500 parts by weight of cyclohexane and methyl cellosolve 500
A coating solution prepared by stirring for 10 minutes at room temperature in a mixed solvent with a weight part was applied using a wire bar, and dried at 80 ° C. for 2 minutes to form a photopolymerizable composition layer having a thickness of 2 μm. Further, a polyvinyl alcohol aqueous solution is applied thereon, and 8
The resultant was dried at 0 ° C. for 2 minutes to form an overcoat layer having a thickness of 3 μm to prepare a photopolymerizable lithographic printing plate.
【0119】得られた光重合性平版印刷版を、直径7c
mのアルミニウム製回転ドラムに、光重合性組成物層が
外側になるように固定した後、830nm、30mWの
半導体レーザー(日立製作所製「HL8325C」)の
ビームを20μmに集光した光強度密度100W/m2
のビームスポットを用いて、300〜1000rpmの
各種回転数にて走査露光し、次いで、0.7重量%の炭
酸ナトリウムと0.5重量%のアニオン性界面活性剤
(花王社製「ペレックスNBL」)とを含有する水溶液
を用いて現像することにより走査線画像を形成させ、線
画像が形成される露光ドラムの最高回転数により感度を
評価し、その各回転数から換算された露光量(mJ/c
m2 )と共に、結果を表1に示した。The resulting photopolymerizable lithographic printing plate was coated with a diameter of 7c.
After fixing the photopolymerizable composition layer on an aluminum rotating drum having an outer diameter of 30 m, a beam of a semiconductor laser ("HL8325C" manufactured by Hitachi, Ltd., "HL8325C") of 830 nm and 30 mW was condensed to 20 μm, and the light intensity density was 100 W. / M 2
Scan exposure at various rotation speeds of 300 to 1000 rpm using a beam spot of 0.7% by weight, and then 0.7% by weight of sodium carbonate and 0.5% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation) ) To form a scanning line image, and evaluate the sensitivity by the maximum number of rotations of the exposure drum on which the line image is formed, and calculate the exposure amount (mJ) converted from each rotation number. / C
The results are shown in Table 1 together with m 2 ).
【0120】又、その各露光量で、175線網点画像露
光を行い、前記と同様の現像処理を施して画像を形成さ
せて平版印刷版を作製した。得られた平版印刷版を平版
印刷機(三菱重工業社製、「DAIYA 1F−2」)
を用いてアート紙(三菱製紙社製)上に印刷し、10万
枚印刷した際の印刷物の網点画像を目視観察し、1〜5
%の面積の網点画像部分の再現性から、以下の基準で印
刷画像再現性を評価した。A lithographic printing plate was prepared by performing 175-line halftone image exposure at each exposure amount and performing the same developing treatment as described above to form an image. The obtained lithographic printing plate was converted to a lithographic printing machine ("DAIYA 1F-2" manufactured by Mitsubishi Heavy Industries, Ltd.).
And printed on art paper (manufactured by Mitsubishi Paper Mills), and visually observed a halftone dot image of the printed matter after printing 100,000 sheets.
From the reproducibility of the halftone dot image portion of% area, the reproducibility of the printed image was evaluated based on the following criteria.
【0121】A;1〜5%の網点が再現している。 B;2〜5%の網点が再現している。 C;3〜5%の網点が再現している。 D;5%以下の網点が再現していない。A: 1 to 5% of halftone dots are reproduced. B: 2 to 5% of halftone dots are reproduced. C: 3 to 5% of halftone dots are reproduced. D: Dots of 5% or less are not reproduced.
【0122】一方、前記で得られた光重合性平版印刷版
を55℃で3日間放置した後、前記と同様の現像処理を
行い、その表面の反射吸光度を、フィルターなしの反射
濃度計(マクベス社製「RD−514」)を用いて測定
し、この値から、光重合性組成物層形成前の支持体表面
の反射吸光度の値を差引いた値により、以下の基準で、
支持体上に残留した光重合性組成物層の量を評価し、結
果を表1に示した。On the other hand, the photopolymerizable lithographic printing plate obtained above was allowed to stand at 55 ° C. for 3 days, and then subjected to the same developing treatment as described above, and the reflection absorbance of the surface was measured using a reflection densitometer (Macbeth without filter). (RD-514) manufactured by the company), and the value obtained by subtracting the value of the reflection absorbance of the surface of the support before the formation of the photopolymerizable composition layer from this value was calculated according to the following criteria.
The amount of the photopolymerizable composition layer remaining on the support was evaluated, and the results are shown in Table 1.
【0123】A;反射吸光度が0.02未満。 B;反射吸光度が0.02以上、0.04未満。 C;反射吸光度が0.04以上、0.06未満。 D;反射吸光度が0.06以上。A: Reflection absorbance is less than 0.02. B: The reflection absorbance is 0.02 or more and less than 0.04. C: Reflection absorbance is 0.04 or more and less than 0.06. D: Reflection absorbance is 0.06 or more.
【0124】又、一方、前記で得られた実施例1〜16
の光重合性平版印刷版を白色蛍光灯(三菱電機社製36
W白色蛍光灯「ネオルミスーパーFLR40S−W/M
/36」)の400ルクスの光強度照射下に1時間放置
した後、前記と同様の現像処理を行ったところ、組成物
層は全て溶解除去されていることが確認された。On the other hand, Examples 1 to 16 obtained above were obtained.
Of a photopolymerizable lithographic printing plate with a white fluorescent light (Mitsubishi Electric 36
W white fluorescent lamp "NEOLMI SUPER FLR40S-W / M"
/ 36 ") for 1 hour under irradiation with a light intensity of 400 lux, and the same developing treatment as described above was carried out. As a result, it was confirmed that the composition layer was completely dissolved and removed.
【0125】実施例17 支持体としてガラス板(コーニング社製「No.705
9」)を用いた外は、実施例2と同様にして光重合性平
版印刷版を作製して、画像露光し、現像した。支持体表
面のガムテープ剥離強度はA、ドラム回転数は500r
pm、経時安定性はAであった。Example 17 A glass plate ("No. 705" manufactured by Corning Incorporated) was used as a support.
Except for using 9 "), a photopolymerizable lithographic printing plate was prepared in the same manner as in Example 2, image-exposed, and developed. The peel strength of the gum tape on the surface of the support is A, and the drum rotation speed is 500r.
pm, and stability over time was A.
【0126】[0126]
【表1】 [Table 1]
【0127】[0127]
【表2】 [Table 2]
【0128】[0128]
【発明の効果】本発明によれば、近赤外線領域の光に対
して高感度を示し、経時安定性に優れると共に、紫外線
領域の光に対しては感応せず、白色蛍光灯下における取
扱性にも優れた光重合性画像形成材を提供することがで
きる。According to the present invention, it exhibits high sensitivity to light in the near-infrared region, is excellent in stability over time, is insensitive to light in the ultraviolet region, and is easy to handle under a white fluorescent lamp. In addition, a photopolymerizable image-forming material having excellent characteristics can be provided.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 長尾 卓美 神奈川県横浜市青葉区鴨志田町1000番地 三菱化学株式会社横浜総合研究所内 Fターム(参考) 2H025 AA00 AA01 AA11 AA16 AB03 AC01 AC08 AD01 BC13 BC31 BC45 BC51 CA14 CA28 CA39 CA42 DA18 2H096 AA06 BA05 EA02 EA04 EA23 ──────────────────────────────────────────────────の Continued on the front page (72) Inventor Takumi Nagao 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Mitsubishi Chemical Corporation Yokohama Research Laboratory F-term (reference) 2H025 AA00 AA01 AA11 AA16 AB03 AC01 AC08 AD01 BC13 BC31 BC45 BC51 CA14 CA28 CA39 CA42 DA18 2H096 AA06 BA05 EA02 EA04 EA23
Claims (8)
g/cm以下の表面を有する支持体の該表面に、下記の
(A)成分、及び、(B−1)成分、(B−2)成分を
含有する光重合性組成物の層が形成されてなることを特
徴とする光重合性画像形成材。 (A)エチレン性不飽和化合物 (B−1)ポリメチン鎖を介して複素環が結合された構
造のシアニン系色素カチオン (B−2)有機硼素アニオン1. The peel strength of the pressure-sensitive adhesive tape is 500.
On the surface of the support having a surface of not more than g / cm, a layer of the photopolymerizable composition containing the following components (A), (B-1) and (B-2) is formed. A photopolymerizable image forming material comprising: (A) Ethylenically unsaturated compound (B-1) Cyanine dye cation having a heterocyclic ring bonded via a polymethine chain (B-2) Organic boron anion
g/cm以下の表面を有する支持体の該表面に、下記の
(A)成分、(B)成分、及び、(C)成分を含有する
光重合性組成物の層が形成されてなることを特徴とする
光重合性画像形成材。 (A)エチレン性不飽和化合物 (B)ポリメチン鎖を介して複素環が結合された構造の
シアニン系色素カチオンと、有機硼素アニオン以外の対
アニオンとの塩 (C)ハロメチル基含有化合物2. The pressure-sensitive adhesive tape having a peel strength of 500.
A layer of a photopolymerizable composition containing the following components (A), (B) and (C) is formed on the surface of a support having a surface of not more than g / cm. Characteristic photopolymerizable image forming material. (A) Ethylenically unsaturated compound (B) Salt of a cyanine dye cation having a heterocyclic ring structure via a polymethine chain and a counter anion other than organic boron anion (C) Halomethyl group-containing compound
して下記一般式(I)で表される(メタ)アクリロイルオ
キシアルキル基含有ウレタン化合物を含有する請求項1
又は2に記載の光重合性画像形成材。 【化1】 〔式(I) 中、R0 は水素原子又はメチル基を示し、Uは
イソシアネート残基を示し、aは0〜3の整数、bは1
〜3の整数、cは1〜3の整数である。〕3. The method according to claim 1, wherein the ethylenically unsaturated compound as the component (A) comprises a (meth) acryloyloxyalkyl group-containing urethane compound represented by the following general formula (I).
Or the photopolymerizable image forming material according to 2. Embedded image [In the formula (I), R 0 represents a hydrogen atom or a methyl group, U represents an isocyanate residue, a is an integer of 0 to 3, b is 1
And an integer c, and c is an integer of 1 to 3. ]
ン、又は、(B)成分におけるシアニン系色素カチオン
が下記一般式(VI)で表されるインドール系又はベンゾチ
アゾール系色素カチオンである請求項1乃至3のいずれ
かに記載の光重合性画像形成材。 【化2】 〔式(VI)中、Y1 及びY2 は各々独立して、ジアルキル
メチレン基又は硫黄原子を示し、R3 及びR4 は各々独
立して、置換基を有していてもよいアルキル基、置換基
を有していてもよいアルケニル基、置換基を有していて
もよいアルキニル基、又は置換基を有していてもよいフ
ェニル基を示し、L2 は置換基を有していてもよいト
リ、ペンタ、ヘプタ、ノナ、又はウンデカメチン基を示
し、該ペンタ、ヘプタ、ノナ、又はウンデカメチン基上
の2つの置換基が互いに連結して炭素数4〜7のシクロ
アルケン環、シクロアルケノン環、シクロアルケンジオ
ン環、又はシクロアルケンチオン環を形成していてもよ
く、縮合ベンゼン環は置換基を有していてもよく、その
場合、隣接する2つの置換基が互いに連結して縮合ベン
ゼン環を形成していてもよい。〕4. The method according to claim 1, wherein the cyanine dye cation of the component (B-1) or the cyanine dye cation of the component (B) is an indole or benzothiazole dye cation represented by the following general formula (VI). Item 4. The photopolymerizable image forming material according to any one of Items 1 to 3. Embedded image [In the formula (VI), Y 1 and Y 2 each independently represent a dialkylmethylene group or a sulfur atom, and R 3 and R 4 each independently represent an alkyl group which may have a substituent, L 2 represents an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, or a phenyl group which may have a substituent, and L 2 may have a substituent. A good tri, penta, hepta, nona, or undecamethine group, wherein two substituents on the penta, hepta, nona, or undecamethine group are connected to each other to form a cycloalkene ring having 4 to 7 carbon atoms, a cycloalkene ring, A cycloalkenedione ring or a cycloalkenethione ring may be formed, and the condensed benzene ring may have a substituent, in which case, two adjacent substituents are connected to each other to form a condensed benzene ring. Even if it forms There. ]
記一般式(IX)で表されるものである請求項1、又は、3
乃至4のいずれかに記載の光重合性画像形成材。 【化3】 〔式(IX)中、R15、R16、R17、及びR18は各々独立し
て、置換基を有していてもよいアルキル基、置換基を有
していてもよいアルケニル基、置換基を有していてもよ
いアルキニル基、置換基を有していてもよいフェニル
基、又は複素環基を示し、これらは互いに連結して環状
構造を形成していてもよく、これらのうち少なくとも一
つは置換基を有していてもよいアルキル基である。〕5. The organic boron anion of the component (B-2) is represented by the following general formula (IX):
5. The photopolymerizable image forming material according to any one of items 1 to 4. Embedded image [In the formula (IX), R 15 , R 16 , R 17 , and R 18 are each independently an alkyl group which may have a substituent, an alkenyl group which may have a substituent, An alkynyl group which may have a group, a phenyl group which may have a substituent, or a heterocyclic group, which may be linked to each other to form a cyclic structure; One is an alkyl group which may have a substituent. ]
下記一般式(XII) で表されるビス(トリハロメチル)−
s−トリアジン化合物である請求項2乃至4のいずれか
に記載の光重合性画像形成材。 【化4】 〔式(XII) 中、Xはハロゲン原子を示し、Wは置換基を
有していてもよいアルキル基、置換基を有していてもよ
いアリール基、又は置換基を有していてもよい複素環基
を示し、R21は水素原子、ハロゲン原子、アルキル基、
又はアリール基を示し、rは0〜2の整数である。〕6. A halomethyl group-containing compound as the component (C) is a bis (trihalomethyl)-represented by the following general formula (XII).
5. The photopolymerizable image forming material according to claim 2, which is an s-triazine compound. Embedded image [In the formula (XII), X represents a halogen atom, W represents an alkyl group which may have a substituent, an aryl group which may have a substituent, or a group which may have a substituent. R 21 represents a hydrogen atom, a halogen atom, an alkyl group,
Or an aryl group, and r is an integer of 0-2. ]
乃至6のいずれかに記載の光重合性画像形成材。7. The support according to claim 1, wherein the support is an aluminum plate.
7. The photopolymerizable image forming material according to any one of items 1 to 6.
乃至7のいずれかに記載の光重合性画像形成材。8. The image forming material is a lithographic printing plate.
8. The photopolymerizable image forming material according to any one of items 1 to 7.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP25789398A JP2000089455A (en) | 1998-09-11 | 1998-09-11 | Photopolymerizable image forming material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25789398A JP2000089455A (en) | 1998-09-11 | 1998-09-11 | Photopolymerizable image forming material |
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Publication Number | Publication Date |
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JP2000089455A true JP2000089455A (en) | 2000-03-31 |
Family
ID=17312661
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---|---|---|---|
JP25789398A Withdrawn JP2000089455A (en) | 1998-09-11 | 1998-09-11 | Photopolymerizable image forming material |
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