GB2273101A - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- GB2273101A GB2273101A GB9322792A GB9322792A GB2273101A GB 2273101 A GB2273101 A GB 2273101A GB 9322792 A GB9322792 A GB 9322792A GB 9322792 A GB9322792 A GB 9322792A GB 2273101 A GB2273101 A GB 2273101A
- Authority
- GB
- United Kingdom
- Prior art keywords
- photosensitive resin
- resin composition
- parts
- group
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims description 62
- -1 titanocene compound Chemical class 0.000 claims description 66
- 229910052782 aluminium Inorganic materials 0.000 claims description 49
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 49
- 239000003999 initiator Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000011230 binding agent Substances 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 17
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 17
- 150000003918 triazines Chemical class 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 claims description 2
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
- 238000007639 printing Methods 0.000 description 39
- 239000007864 aqueous solution Substances 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000004793 Polystyrene Substances 0.000 description 26
- 230000035945 sensitivity Effects 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000007644 letterpress printing Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003486 chemical etching Methods 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000007788 roughening Methods 0.000 description 5
- 229940001593 sodium carbonate Drugs 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000004115 Sodium Silicate Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- 229910052911 sodium silicate Inorganic materials 0.000 description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 125000004953 trihalomethyl group Chemical group 0.000 description 4
- 230000004304 visual acuity Effects 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000007743 anodising Methods 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 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 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-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
- 244000215068 Acacia senegal Species 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Chemical group 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- SUDVPELGFZKOMD-UHFFFAOYSA-N 1,2-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)C)C(C(C)C)=CC=C3SC2=C1 SUDVPELGFZKOMD-UHFFFAOYSA-N 0.000 description 1
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 1
- GDGUCRQNTDPGSD-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO.OCC(CO)(CO)CO GDGUCRQNTDPGSD-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- TWMGONWXQSKRMH-UHFFFAOYSA-N 2-[4-(2-phenylethenyl)phenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=CC(C=CC=3C=CC=CC=3)=CC=2)=N1 TWMGONWXQSKRMH-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- VYKGZYAKGHXTNC-UHFFFAOYSA-N 2-nonyl-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(CCCCCCCCC)CO1 VYKGZYAKGHXTNC-UHFFFAOYSA-N 0.000 description 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- RXHZPGSSIWOFGS-UHFFFAOYSA-N 9-(3-acridin-9-ylpropyl)acridine Chemical compound C1=CC=C2C(CCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 RXHZPGSSIWOFGS-UHFFFAOYSA-N 0.000 description 1
- IPRFSEGUKLMSFA-UHFFFAOYSA-N 9-(5-acridin-9-ylpentyl)acridine Chemical compound C1=CC=C2C(CCCCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 IPRFSEGUKLMSFA-UHFFFAOYSA-N 0.000 description 1
- YDTZWEXADJYOBJ-UHFFFAOYSA-N 9-(7-acridin-9-ylheptyl)acridine Chemical compound C1=CC=C2C(CCCCCCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 YDTZWEXADJYOBJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- HEMIGQSLPQVXSZ-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(CC)(CO)CO.C(O)NC(C=C)=O Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(CC)(CO)CO.C(O)NC(C=C)=O HEMIGQSLPQVXSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical group [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-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
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001915 proofreading effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
Description
2273101 PHOTOSENSITIVE RESIN COMPOSITION
FIELD OF THE INVENTION
This invention relates to a photosensitive resin composition having very high sensitivity and excellent developability. More particularly, it relates to a photosensitive resin composition which cures on exposure to visible light, such as ultraviolet rays and argon laser light, to provide a pattern and is useful as a resist (e.g., a photoresist, a photosolder resist, a plating resist) for printing plates, such as a letterpress printing plate, an intaglio printing plate and a litho printing plate, or printed circuit boards, as a resist for preparing a color filter or a black matrix of liquid crystal displays or plasma displays, and as a photopolymerizable paste composition. The present invention also relates to a presensitized plate using the photosensitive resin composition.
BACKGROUND OF THE INVENTION
Techniques of applying a photosensitive resin composition comprising a high polymeric binder, an ethylenically unsaturated double bondcontaining monomer, and a triazine photopolymerization initiator to printing plate making, formation of a photoresist, and the like are hitherto known. The triazine photopolymerization initiators are broadly employed because of their higher sensitivity to achieve satisfactory im, :Ige reproducibility than various other - 1 i initiators, such as benzophenone initiators, anthraquinone initiators, and thioxanthone initiators.
Examples of known photosensitive resin compositions described above include a photosensitive image-forming composition comprising a 2,4,5triarylimidazolyl dimer as a photopolymerization initiator and an addition polymerizable ethylenically unsaturated monomer discl6sed in JPA-60-202437 (the term "JP-A" as used herein means an "unexamined published Japanese patent application") and a photosensitive composition containing a photosensitive s-triazine compound disclosed in JP-A-60- 239736.
The triazine compounds described in these publications have a disadvantage of poor storage stability and are apt to produce scum during development. In order to overcome this, triazine compounds having a specific structure have been proposed as disclosed in JP-A-63-68831 and JP-A-63-70243. In recent years, however, development of photosensitive compositions having a higher resolving power and improved developability have been demanded in the field of printing plates, printed circuit boards, electronic devices, and the like, and even the above-mentioned improved triazine compounds are still unsatisfactory in both of resolving power and developability.
With the latest technological development of electronic devices such as computers, factory automation has advanced also in the field of printing, enabling integral processing from
2 - j input of an original or image data through plate making, inclusive of editing and proofreading. In such an advanced plate making technique, direct imaging using a laser beam is employed. The laser beam to be used is pref erably an argon laser beam having a wavelength of 488 nm in the visible region. Hence, it has been demanded to develop a resin composition having photosensitivity to visible light. Various photosensitive resin compositions meeting this demand have been proposed to date as described, e.g., in JP-A-63-260909, JP-A-1105238, JP-A-1203413, JP-A-1-203414, JP-A-2-1714, JP-A-273813, JP-A-2-127404, and JP-A3-239703.
Of these proposals, the compositions described in JP-A63-260909, JP-A-1105238, JP-A-1-203413, JP-A-203414, JP-A-21714 and JP-A-2-73813 use an acridine compound and a trihalomethyl-containing triazine compound as a photopolymerization initiator, and the compositions of JP-A-2127404 and JP-A-3-239703 use a metallocene compound in addition to the abovementioned photopolymerization initiators.
On the other hand, with respect to a presensitized plate (hereinafter abbreviated as a PS plate) suitable for producing a litho printing plate, a known process for producing a PS plate comprises subjecting surfacegrained aluminum plate 1 to anodizing to form oxide layer 2, rendering the oxide layer hydrophilic, and then coating a photosensitive resin composition on the resulting aluminum substrate to form photosensitive resin layer 3 as shown in FIG. 1. If desired, 3 - overcoat layer 4 may be provided on the resin layer as an oxygen barrier.
When the above-mentioned PS plate, etc.. is exposed to high energy radiation, such as ultraviolet light, a film original must be used, which gives rise to a problem of poor image reproducibility due to the poor image reproduction of the film itself and insufficient contact between the film and the photosensitive resin layer. When a laser beam is used f or exposure, image formation is conducted by direct scanning without using a film original and is therefore free from the problem of reproducibility. The problem associated with image formation with a laser beam is that a high-energy shortwavelength laser has a short life for practical use and that a laser having a relatively long wavelength, such as an argon laser, has low energy and demands a highly sensitive photosensitive resin composition. It has therefore been demanded to develop such a highly sensitive photosensitive resin composition.
Returning to the compositions using an acridine compound and a trihalomethyl-containing triazine compound, their sensitivity to argon laser light is insufficient, with the problems such as a long exposure time required and a reduction in image reproducibility due to insufficient curing still remaining unsolved. The technique using a metallocene compound in combination as disclosed in JP-A-2-127404 also j fails to satisfy all the requirements of sensitivity, adhesion, developability, and pattern forming precision.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a photosensitive resin composition which has a high resolving power, satisfactory developability, and sufficient sensitivity to argon laser light of low energy and is useful as a photoresist, a photosolder resist or a plating resist for printing plates, such as a letterpress printing plate, an intaglio printing plate and a litho printing plate, or printed circuit boards; a resist composition for preparing a color filter or a black matrix of liquid crystal displays or plasma displays; and a photopolymerizable paste composition.
Another object of the present invention is to provide a PS plate which is sensitive to argon laser light to f orm a precise image and capable of reducing the number of steps involved for plate making.
In order to accomplish the above objects, the present inventors have conducted extensive and intensive investigations. As a result, they have found that a specific triazine compound having a bromine atom on the substituted phenyl nucleus thereof or a specific trihalomethyl-containing triazine compound is an excellent photopolymerization initiator providing a photosensitive resin composition having a high resolving power, satisfactory developability, and sufficient 4 sensitivity to argon laser light. The present invention has been completed based on this finding.
The present invention relates to a photosensitive resin composition comprising a high polymeric binder, an ethylenically unsaturated double bond-containing monomer, and a photopolymerization initiator, in which the photopolymerization initiator is at least one compound selected from triazine compounds represented by formulae (I) through (V):
x1 N--<\ C (X3 b Rl /' ---/ N N-\ C (X3 t \X2 b xl N -<\ C (X3)3 N H2.C\,/---\x2N<C(X3)3 Xl N -\ C (X3)3 Rl-.R2 / ' N N-\C (X3)3 - 6 (I) (II) (III) 3 xl C)- '\-R2-/ /1 H: X2 R 3 N-< C (X3)3 N N \C (X3)3 CC1 1 H C 2 4 CC1 R 3 (IV) (V) wherein X' and X1 each independently represents a hydrogen atom or a bromine atom; X3 represents a chlorine atom or a bromine atom; R' represents an alkyl group having f rom 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms; R 2 represents a methylene group or a vinylene group; and R 3 and R 4 each independently represents- a hydrogen atom or a methyl group.
It is preferable to use the photopolymerization initiators of formulae (I) to (V) in combination with a titanocene compound and/or an acridine compound.
The present invention also provides a PS plate comprising an aluminum substrate whose surface has been mechanically and electrolytically grained, anodized, and rendered hydrophilic having provided thereon a photosensitive v- resin layer, in which the photosensitive resin layer comprises the above- mentioned photosensitive resin composition.
The PS plate preferably has an oxygen-barrier overcoat layer mainly comprising polyvinyl alcohol on the photosensitive resin layer thereof.
BRIEF DESCRIPTION OF THE DRAWINGS
FIGs. 1 and 2 each shows a cross section of a PS plate according to the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Specific examples of the triazine compounds represented by f ormulae (I) to (V) which can be used as a photopolymerization initiator in the present invention are shown below f or illustrative purposes only but not for limitation (1) (2) CH30 N N \ CC15 CC13 NU N H:
CCIS -.8 - (3) (4) (5) (6) (7) (8) r PN _C13 CH3 N N:--'\/ r CC13 CH - r N Ci3 WC14- 7 N W--( rr CCL N--C6 CH3 H=CH- N -c N-\ CC6 N--C6 CH30 H2-/ N N ----< C r CC6 - Br3 N CH3 3-C N rr CBr3 cci3 N - CHz0::Y--i--H=C. < N N--\ Br C1-13 - 9 (9) (10) (11) (H20 N-\ Br cce, C;%/-,-13 N CHz0 -0- -/ N N--\ CCL N -\.
0--n -e N (Z CL, Among these compounds, preferred are Compounds (1) and (10).
These triazine compounds can be obtained by, for example, reacting trichloroacetonitrile with a compound having a cyano end group in the presence of sodium hydroxide as a catalyst. The thus prepared triazine compounds are usually high-melting needle crystals having a melting point between 1001C and 3001C and assuming a pale yellow to orange color.
As compared with conventional triazine compounds, the compounds according to the present invention exhibit significantly improved solubility in the solvents hereinafter described owing to a bromine atom introduced into the phenyl nucleus thereof or a specific trihalomethyl group introduced into the triazine nucleus. As a result, they have highly - lo i increased sensitivity to light and improved developability. They also have improved sensitivity to visible light enough to cure with argon laser light.
The PS plate having a photosensitive resin layer comprising the photosensitive resin composition of the present invention can achieve imaging with argon laser light without using a film original. Therefore, it has high precision of image formation and reduces the number of steps for plate making.
If desired, the photopolymerization initiator according to the present invention may be used in combination with known initiators for further improvement in sensitivity. Specific but non-limiting examples of usable other initiators include anthraquinone and derivatives thereof (e.g... 2methylanthraquinone, 2-ethylanthraquinone), benzoin and derivatives thereof (e.g., benzoin methyl ether, benzoin ethyl ether), thioxanthone derivatives (e.g., chlorothioxanthone, diisopropylthioxanthone), benzophenone and derivatives thereof (e.g., 4,41bis(dimethylamino)benzophenone), acetophenone and derivatives thereof (e. g., dimethoxyphenylacetophenone), Michler's ketone, and benzil.
Preferably, a titanocene compound and/or an acridine compound such as 9phenylacridine are used in combination with the photopolymerization initiator of the present invention to provide a photosensitive resin composition sensitive to visible light of relatively low energy, such as argon laser light.
- il A titanocene compound, which imparts sensitivity to visible light to a high polymeric binder, includes a compound represented by formula (VI) shown below as disclosed in JP-A-2127404, JP-A-3-27393, and JP-A-3-239703.
R,,,R 7 R R 8 (VI) wherein R-5 and R 6, which may be the same or dif f erent, each represents a substituted or unsubstituted cyclopentadienyl group; and R 7 and R, which may be the same or different, each represents a substituted or unsubstituted phenyl group.
The titanocene compound is preferably used in an amount of from 10 to 30 parts by weight, more preferably from 12 to 20 parts by weight, based on 100 parts by weight of the total solids content of the photosensitive resin composition. The total solids content of the photosensitive resin composition means a total of a high polymeric binder, an ethylenically unsaturated double bond-containing monomer and a photopolymerization initiator. It is difficult to achieve a sufficient increase in sensitivity to visible light with less than 10 parts by weight of the titanocene compound. If the amount of the titanocene compound is more than 30 parts by weight, a reduction in film strength of the resulting cured film may result.
The triazine compounds according to the present invention are characterized by their structure having a bromine- substituted phenyl group, a piperonyl group and/or a substituted styryl group as well as their physical properties as compared with the conventionally employed bistrihalomethyltriazine compounds or tristrihalomethyltriazine compounds. By virtue of these characteristics, the triazine compounds of the invention raise sensitivity of a photosensitive resin composition about ten times over a titanocene compound used alone.
In order to suppress reduction in sensitivity due to air oxidation of the photosensitive resin composition, an acridine compound is preferably used in combination. Examples of suitable acridine compounds are 9phenylacridine, 9-(4substituted)phenylacridine, 9-substitutedaminoacridine, 1,7bis(9-acridinyl)heptane, 1,5-bis(9-acridinyl)pentane, and 1,3bis(9-acridinyl)propane.
The acridine compound is preferably used in an amount of from 0.1 to 10 parts by weight, more preferably from 0.5 to 5 parts by weight, based an 100 parts by weight of the total solids content of the photosensitive resin composition. If the amount of the acridine compound is less than 0. 1 parts by weight, the effect of preventing sensitivity reduction due to oxygen may not be fully exerted as expected in some cases. The acridine compound in amounts exceeding 10 parts by weight are apt to bring about undesired effects, such as an abrupt reduction in development rate and production of a development residue.
In addition to the above-mentioned components, the photosensitive resin composition of the present invention preferably contains a coumarin compound as a sensitizer for further increasing its sensitivity. Suitable coumarin compounds include those represented by formulae (i) and (ii) shown below and commercially available compounds, such as LS157, LS-153 and LS-158, produced by Mitsui Toatsu Chemicals, Inc.
S:C) N (C2Hs).2N 0 0 H N 0 0 (i) (ii) The coumarin compound is preferably added in such an amount as to adjust the absorbance of the photosensitive resin composition to a range of from 0.1 to 1.5, more preferably from 0.3 to 0.8, at 488 nm. If the absorbance is less than 0.1 or more than 1.5, a reduction in sensitivity are apt to result in some cases.
14 - A The triazine compounds represented by formulae (I) to (V) are preferably used either individually or in combination of two or more thereof in a total amount of f rom 0 - 1 to 15 parts by weight, more preferably from 0. 5 to 5 parts by weight, based on 100 parts of the total solids content of the photosensitive resin composition. If the amount is less than 0.1 parts by weight, no improvement in sensitivity is shown in some cases. If it is more than 15 parts by weight, there is a tendency that a non-developed residue or a foreign matter due to insufficient dissolution is produced. In addition to the triazine compounds of the invention, known trihalomethyltriazine compounds may be added in combination in a total amount not exceeding 50% by weight of the total triazine compounds.
The high polymeric binders which can be used in the present invention include homo- or copolymers of monomers selected f rom compounds having a phenolic hydroxyl group (e. g., p-hydroxyphenyl (meth)acrylate), compounds having an aliphatic hydroxyl group (e.g., 2-hydroxyethyl (meth)acrylate), substituted or unsubstituted alkyl (meth)acrylates, (meth)acrylamides, vinyl ethers, vinyl esters, vinyl ketones, alkylene- substituted aromatic compounds (e.g., styrene), olefins, (meth)acrylonitriles, and compounds having an unsaturated double bond (e. g., acrylic acid).
Specific examples of suitable high polymeric binders are polyamide, polyvinyl esters, polyvinyl acetal, polyvinyl - 15 ethers, epoxy resins, alkyd resins, polyethylene oxide, polyvinylmethylacetamide, polyvinylmethylformamide, polyvinylpyrrolidone, polydimethylacrylamide, chlorinated polyethylene, chlorinated polypropylene, and polyalkyl acrylates.
Additionally, alkyl acrylate-acrylonitrile copolymers, polyvinyl chloride, vinyl chloride-acrylonitrile copolymers, polyvinylidene chloride, vinylidene chloride-acrylonitrile copolymers, polyvinyl acetate, polyvinyl alcohol, acrylonitrile-styrene copolymers, acrylonitrile- styrenebutadiene copolymers, polystyrene, polymethylstyrene, polyurethane, methyl cellulose, acetyl cellulose, polyvinyl formal, and polyvinyl butyral may also be used as a binder.
Addition of an organic acid, such as a carboxylic acid, to the abovementioned monomers provides alkali -developable binders. In this case, the alkali-developable high polymeric binders preferably have an acid value between 100 and 150 and an average molecular weight of 10,000 to 200,000. High polymeric binders containing a hydroxyl or carboxylic group may be modified with glycidyl (meth)acrylate, etc. to have an additional unsaturated double bond.
When the carboxyl-containing high polymeric binder is a copolymer, the copolymer is preferably prepared in the presence of a monomer having an unsaturated double bond (e.g., (meth)acrylic acid or crotonic acid), a copolymer of maleic anhydride or a half ester thereof, a reaction product between - 16 j a hydroxyl-containing copolymer and an acid anhydride, and the like.
Preferred combinations of monomers of the high polymeric binders include a combination of methacrylic acid/methyl methacrylate/benzyl methacrylate/hydroxyphenyl methacrylate and a combination of methacrylic acid/methyl methacrylate/styrene/hydroxyphenyl methacrylate.
The monomers containing an ethylenically unsaturated double bond which can be used in the present invention preferably include monomers or oligomers containing at least one, and preferably two or more addition polymerizable ethylenically unsaturated groups, having a molecular weight of 5,000 or less, and having a boiling point of 1000C or higher at atmospheric pressure.
Specific examples of such monomers or oligomers include (meth)acrylic acid, (meth)acrylic ester (e.g., methyl (meth)acrylate and ethyl (meth)acrylate), (meth)acrylamide, (meth)acrylonitrile, allyl compound, vinyl ether, vinyl ester, ethylene glycol mono(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol mono(meth)acrylate, polyethyelne glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolethane tri(meth)acrylate, neopentyl glycol tri(meth)acrylate, dipentaerythritol di(meth)acrylate, di(meth)acrylate, pentaerythritol pentaerythritol tetra(meth)acrylate, hexa(meth)acrylate, hexanediol tri(acryloyloxyethyl) isocyanurate, (meth)acrylate of an ethylene oxide- or propylene oxide-added polyhydric alcohol (e.g., glycerol), urethane acrylate compound, and epoxy acrylate compound.
Preferred ethylenically unsaturated double bondcontaining monomers are polyfunctional monomers.
Polyfunctional monomers serving as a crosslinking agent preferably include ethylene glycol diacrylate, ethylene glycol di(meth)acrylate, triethylene glycol diacrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol diacrylate, tetraethylene glycol di(meth)acrylate, propylene glycol diacrylate, propylene glycol di(meth)acrylate, trimethylolpropane triacrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol triacrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetraacrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol pentaacrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexa(meth)acrylate, and carboepoxy diacrylate.
Among them, more preferred are trimethylolpropane triacrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tri(meth)acrylate and pentaerythritol tetraacrylate.
If desired, the photosensitive resin composition of the present invention may further contain known additives, such as thermal polymerization initiators (e.g., methyl hydroquinone), antifoaming agents, and dyes. When the photosensitive resin - 18 composition is used as a photasolder resist composition or a plating resist composition, the additives such as fine particles of metals or metal oxides (e.g., copper, brass, aluminum, silicon oxide, aluminum oxide, magnesium oxide) and fine particles of plastics compatible with the photosensitive resin composition may be preferably added in an amount of from 1 to 40 parts by weight per 100 parts by weight of the total solids content of the photosensitive resin composition.
The compounding ratio of the above-mentioned components in the photosensitive resin composition more or less varies depending on the final use (e.g., use for a PS plate, a letterpress printing plate, a printed circuit board). Preferably, the photosensitive resin composition comprises from 10 to 60 parts by weight of the high polymeric binder, from 20 to 70 parts by weight of the ethylenically unsaturated double bond-containing monomer, and from 0.1 to 30 parts by weight of the photopolymerization initiator each based on 100 parts by weight of the total solids content of the photosensitive resin composition.
The photosensitive resin composition is prepared by mixing the abovementioned components with the aid of from 10 to 1,000 parts by weight of a known solvent, such as alkylene glycol mono(or di)alkyl ethers, ketones, alcohols, and carboxylic acid esters, per 100 parts by weight of the total solids content of the photosensitive resin composition.
The photosensitive resin composition according to the present invention is useful as a photoresist, a photosolder resist or a plating resist in the production of various printing plates, such as a letterpress printing plate, an intaglio printing plate, a litho printing plate, etc. or printed circuit boards, a resist for preparing a color filter or a black matrix of liquid crystal displays or plasma displays, and a photopolymerizable paste composition.
When the composition is used for production of a printing plate, it is coated on a substrate (e.g., metal, plastic) to form a photosensitive resin layer. Suitable examples of such substrates include plates of metals, such as iron, aluminum, zinc, copper, brass and stainless steel; synthetic resins, such as polyethylene terephthalate (PET), nylon, polyethylene, polypropylene and acrylic resins, shaped into a plate or a film according to the specifications of a printing machine used; and laminates of the resin films prepared by using an adhesive, etc.
A resist can be prepared from the photosensitive resin composition by using an argon laser as a light source as follows. The composition is first diluted with a known organic solvent, such as methyl ethyl ketone, toluene, ethylene glycol monomethyl ether and 2-methoxyethanol, to a solid content of about 5 to 20% by weight. The coating composition is coated on a substrate, such as an aluminum plate, or, in the case of preparing a dry film resist, on a PET film to a dry film - 20 thickness of from 1 to 4 g/M2 and dried in an air flow at room temperature to form a photosensitive resin layer.
It is preferable to provide an oxygen-barrier overcoat layer mainly comprising polyvinyl alcohol (PVA) on the photosensitive resin layer. The overcoat layer may consist of PVA, or polyalkylenealcohol (average molecular weight: 250 to 1,000) may be added to the overcoat layer in an amount of from 10 to 70 parts based on 100 parts of PVA. PVA to be used preferably has an average molecular weight of 300 to 1,000 and a degree of, saponification (i.e., rate of hydrolysis of an acetyl group) of 70 to 90%. For easy coating, PVA is used as diluted with water to a solid content of 5 to 20% by weight. In preparing a PVA aqueous solution, approximately the same amount of silicon dioxide powder as PVA and an adequate amount of a surface active agent, e.g., a nonylphenyl ethylene oxide adduct, are preferably added. The overcoat layer is preferably coated to a dry film thickness of 1 to 2 gm.
The thus prepared film cures with high sensitivity on imagewise exposure to 1 to 3 Mj/CM2 of argon laser light (wavelength: 488 nm). A holding time of exposure is preferably from about 30 minutes to about 1 hour. Exposure to laser light is carried out by scanning with a laser beam emitted from a fine nozzle according to the instructions from a controller so that imaging can be effected with far higher precision than the conventional imaging by UV irradiation using a film original. Use of a laser as- a light source also provides an advantage of simplification of operation. After the exposure, the film is developed by brushing in a developer, f or example, a dilute sodium carbonate aqueous solution at room temperature for about 1 minute to form a resist pattern.
The thus prepared resist pattern is suitable as a resist against etching in the production of a PS plate, a letterpress printing plate, an intaglio printing plate, a printed circuit board, and so forth.
A PS plate, a precursor of a litho printing plate, etc., is usually prepared by using an aluminum or aluminum alloy plate as a substrate in the same manner as for a resist as described above. Examples of suitable aluminum or aluminum alloy plates include those specified in JIS A-1050, JIS A-1100, JIS A-3003, JIS A-3103, and JIS A-5005.
The aluminum plate is first subjected to mechanical surf ace graining. If desired, the aluminum plate may be subjected to a pretreatment for removing a rolling lubricant from the surface or a pretreatment for exposing a clean aluminum surface with a solvent (e.g., trichloroethylene), a surface active agent or a sodium silicate for the former pretreatment, and with an alkali etching solution of sodium hydroxide, potassium hydroxide, etc. for the latter pretreatment. Mechanical surface graining of an aluminum plate can be carried out by various known methods, for example, sandblasting, ball graining, wire graining, and brush graining, with brush graining being preferred. For the details of brush graining, refer to U.S. Patent 3,891,516 (corresponding to JPB-51-46003) and JP-B-50-40047 (the term "JP-B" as used herein means an "examined published Japanese patent application"). Mechanical surface graining is preferably performed to give an average center-line surface roughness Ra (according to JIS B 0601) of from 0.2 to 1.0 gm. By the mechanical surface graining, the surface of the aluminum plate is given unevenness at relatively large intervals (primary structure) and fine projections (secondary structure) on all over the uneven surface.
The mechanically grained aluminum plate is then chemically etched in order to clear the surface off any remaining abrasive and aluminum dust and to remove the fine projections thereby to facilitate uniform and effective achievement of subsequent electrochemical surface roughening. The chemical etching is carried out by soaking the aluminum plate in an aqueous solution of an acid or a base capable of dissolving aluminum. For the details, reference can be made to U.S. Patent 3,834,998. Suitable acids include sulfuric acid, persulf uric acid, and hydrochloric acid, and suitable bases include sodium hydroxide, potassium hydroxide, sodium tertiary phosphate, sodium secondary phosphate, potassium tertiary phosphate, potassium secondary phosphate, sodium aluminate, and sodiumcarbonate. A basic aqueous solution is preferred as an acidic etching solution f or its higher etching rate. When chemical etching is effected with a basic aqueous solution, smut is generally produced on the aluminum surface. This being the case, the aluminum plate is preferably subjected to desmutting with phosphoric acid, nitric acid, sulfuric acid, chromic acid or a mixed acid containing two or more of these acids.
The thus treated aluminum plate is then electrochemically roughened in an acidic electrolytic solution comprising an aqueous solution of nitric acid, hydrochloric acid, a mixture of nitric acid and hydrochloric acid, and a mixture of these acids and others, such as organic acids, sulfuric acid and phosphoric acid. The electrolytic bath may contain a corrosion.. inhibitor (or a stabilizer). The electrochemical surface roughening may be conducted in any of a batch system, a semi-continuous system and a continuous system.
After completion of the electrolytic surface roughening, the aluminum plate is again subjected to chemical etching with a base, such as sodium hydroxide. This chemical etching is carried out in the same manner as in the abovedescribed chemical etching using a base. The chemical etching is preferably followed by desmutting with phosphoric acid, nitric acid, sulfuric acid, chromic acid, etc.
The surface roughened aluminum plate is then subjected to anodizing in accordance with well-known procedures. For example, anodizing is carried out in an electrolytic solution comprising an aqueous or non-aqueous solution of sulfuric acid, 1 phosphoric acid, oxalic acid, chromic acid, amidosulf onic acid, a mixture of two or more of these acids, which may contain an AP ion, by mainly using a direct current. An alternating current or a combination of a direct current and an alternating current may also be used.
The anodized aluminum plate may further be subjected to a treatment for rendering the surface hydrophilic by, for example, immersion in an aqueous solution of an alkali metal silicate, e.g., sodium silicate, as taught in U.S. Patents 2,714,066 and 3,181,461. The silicate treatment is preferably followed by a treatment for further rendering the surface hydrophilic with phosphonic acid.
If desired, an undercoat layer comprising a high polymer containing a sulfonic group- containing monomer unit as described in JP-A-59-101651 or an undercoat layer comprising a compound containing an -NH4 group, a COOH group or an -S03H group may be provided on the aluminum plate.
The resulting aluminum substrate is coated with the photosensitive resin composition of the present invention to obtain a litho printing plate precursor, such as a PS plate, having a photosensitive resin layer. Coating is carried out by means of a bar coater, a f oiler, and the like. The coated composition is then dried, for example, at about18OC for 4 to 8 minutes. A dry f ilm, thickness is generally f rom, 1 to 10 g/M2. preferably from 2 to 4 g/M2. If the dry thickness is less than 1 g/MZ' the resulting printing plate are apt to have poor printing durability and poor ink receptivity. If it is more than 10 g/m 2, the printing plate precursor are apt to have impractical sensitivity.
If desired, an oxygen-barrier overcoat layer mainly comprising PVA may be provided on the photosensitive resin layer by means of a roller coater, a foiler, etc. Drying of the overcoat layer is effected by, for example, at about 80'C for 1 to 3 minutes.
The present invention will now be illustrated in greater detail with reference to Examples, but the present invention should not be construed as being limited thereto. All the percents, parts, and ratios are by weight unless otherwise indicated.
EXAMPLE 1-1 1) Preparation of Aluminum Substrate:
Pretreatment of aluminum plate 1 shown in FIG. 2 was conducted as follows.
The surface of aluminum plate 1 having a thickness of 0. 30 mm was grained with a nylon brush and a pumice stone aqueous slurry and thoroughly washed with water. The aluminum plate was soaked in a 10% sodium hydroxide aqueous solution at 70C for 60 seconds, washed with running water, neutralized with a 20% nitric acid aqueous solution, and washed with water.
The aluminum plate was then subjected to electrolytic surface roughening in a 1% nitric acid aqueous solution at an anode-hour quantity of electricity of 160 C/dM2 using a sinusoidal alternating current at an anode-hour voltage VA of 12.7 V. The resulting aluminum plate had an Ra of 0.6 4m.
The aluminum plate was soaked in a 30% sulfuric acid aqueous solution at 500C for 2 minutes for desmutting and then subjected to anodic oxidation in a 20% sulfuric acid aqueous solution at a current density of 2 A/dM2 for 2 minutes to form oxide layer 2 having a thickness of 2.7 g/M2. Subsequently, the aluminum plate was immersed in a 2.5% sodium silicate aqueous solution at 700C for 1 minute, washed with water, and dried to prepare an aluminum substrate.
2) Preparation of Photosensitive Resin ComiDosition:
High polymeric binder comprising methylmethacrylate/methacrylic acid/hydroxyphenyl methacrylate/ benzyl methacrylate (50/20/10/20) Pentaerythritol triacrylate Triazine Compound (1) 9-Phenylacridine parts parts 2 parts 0.2 part Methyl hydroquinone 0.05 part Ethylene glycol monomethyl ether 100 parts Methyl ethyl ketone 60 parts The above components were thoroughly kneaded, and resulting composition was coated on the aluminum substrate a dry coverage of 2 g/M2 and dried at 1000C for 2 minutes obtain PS plate 4 having photosensitive resin layer 3.
the to to 3) Preparation of Litho Printing Plate:
PS plate 4 was exposed to 20 mj/cm2 of ultraviolet light f rom. an ultrahigh pressure mercury lamp through a photomask and then immersed in a 0. 5% sodium carbonate aqueous solution at 250C for 3 minutes to obtain a printing pattern. The resulting pattern suffered neither appreciable loss in film thickness due to corrosion with the developer nor remaining of the film on the non-exposed area. Finally, the aluminum substrate with the printing pattern on it was rubberized with gum arabic and postcured by exposure to 1 j/CM2 Of light of a metal halide lamp to complete a litho printing plate.
The resulting printing plate was mounted on a printing machine and printing was carried out. About 300,000 satisfactory prints were obtained.
EXAMPLE 1-2 1) Preparation of Photosensitive Resin Composition:
High polymeric binder described in Example 1-1 Pentaerythritol triacrylate Triazine Compound (2) Titanocene compound (a) e1__ I- p,,[ 1 -'\ - 28 parts parts 3 parts 10 parts 9-Phenylacridine 3 parts Ethylene glycol monomethyl ether 100 parts Methyl ethyl ketone 60 parts The above components were thoroughly kneaded to prepare a photosensitive coating composition.
2) Preparation of Litho Printina Plate:
The coating composition was coated on the same aluminum substrate as prepared in Example 1-1 to a dry thickness of 3.5 g/cml. After drying the coated composition, an aqueous solution containing PVA and silicon dioxide powder (PVA/ S'C)2 /water = 7/7/86 by weight) was coated thereon to a dry film thickness of 1.5 g/cm2 to form an overcoat layer for oxygen shielding and for excluding adverse influences of standing wave.
The resulting PS plate was imagewise scanned with an argon laser beam of 1 Mj/CM2, and developed and postcured in the same manner as in Example 171 to complete a printing plate. The pattern suffered neither appreciable loss in thickness due to corrosion with the developer nor remaining of the film on the non-exposed area.
The resulting printing plate was mounted on a printing machine and printing was carried out. About 150,000 satisfactory prints were obtained.
EXAMPLE 1-3 1) Preparation of Photosensitive Resin ComDosition:
Partially saponified PVA (degree of polymerization: 500; degree of saponification: 80%) Condensate of dimethylolurea dimethyl 60 parts ether and N-methylolacrylamide Trimethylolpropane triacrylate 20 parts Triazine Compound (1) 5 parts Methyl hydroquinone 0.05 part Methanol 50 parts Water 150 parts The above components were thoroughly kneaded to prepare a photosensitive coating composition. 2) Preparation of Letterpress Printing Plate: The coating composition was coated on a 0.5 nun thick aluminum substrate prepared in the same manner as in Example 1-1 to a dry film thickness of 1 mm and dried at 40C for 15 hours to obtain a letterpress'printing plate precursor. The precursor was exposed to 700 Mj/CM2 Of Ultraviolet light through a photomask having a negative pattern, developed with warm water at 450C for 2 minutes by means of a spray washer, dried, and postcured at 1 j/CM2 to complete a letterpress printing plate. When printing was carried out using the resulting printing plate, 300,000 satisfactory prints free from stains on the image area were obtained.
parts - 30 7 EXAMPLE 1-4
11 Preparation of Photosensitive Resin Composition:
Methyl acrylate/methyl methacrylate/ 50 parts isobutyl methacrylate (25/50/25; average molecular weight: 50,000) Pentaerythritol triacrylate Triazine Compound (1) Methyl hydroquinone Oil Blue #613 (produced by Orient Chemical Co., Ltd.) Ethyl acetate/methyl ethyl ketone (7/3) parts 2 parts 0.05 part 0.02 part parts The above components were kneaded to prepare a photosensitive coating. composition.
2) PreDaration of Printed Circuit Board:
The coating composition was coated on a copper-clad glass epoxy substrate having a copper foil thickness of 35 4m to a dry f ilm thickness of 50 Im and dried. The resulting cured film was exposed to 100 mJ/cm2 of ultraviolet light through a photomask,and developed with a 1% sodium carbonate aqueous solution at 27'C for 60 minutes by means of a spray washer to form an etching resist. The resulting resist was free from pattern deficiencies, peeling and remaining of the unexposed area.
The copper surface was then subjected to spray etching with a ferric chloride aqueous solution (specific gravity: 40OBe (Baumd degree)) at 450C at a spray pressure of 1.2 kg/cm2 for 60 seconds. After washing with water, the resist film was removed with a 5% sodium hydroxide aqueous solution to provide a copper wiring pattern with high fidelity to the pattern of the photomask.
As is apparent from Examples 1-1 to 1-4, the photosensitive resin composition according to the present invention which contains at least one photopolymerization initiator selected from the triazine compounds represented by formulae (I) to (V) easily dissolves in a solvent and therefore provides a printing plate such as a PS plate, etc. with high sensitivity and satisfactory developability.
When the triazine compound of the present invention is used in combination with a titanocene compound or an acridine compound, a photosensitive resin composition sensitive to visible light of relatively low energy, such as argon laser light, can be obtained.
EXAMPLE 2-1 1) Preparation of Aluminum Sub_strate:
A 0.3 mm thick aluminum plate (JIS A-1050 material) was degreased by soaking in a 10% sodium hydroxide aqueous solution at 501C for 20 seconds, washed with water, neutralized in a 25% sulfuric acid aqueous solution for 30 seconds, and washed with water. The surface of the aluminum plate was grained with a nylon brush and an aqueous slurry of pumice stone (400 mesh), followed by thoroughly washing with water. The plate was then etched with a 20% sodium hydroxide aqueous solution at 701C to dissolve out 10 g/mZ of aluminum, followed by washing with water. The etched aluminum plate was desmutted with a 25% nitric acid aqueous solution and washed with water.
The aluminum plate was then subjected to electrolytic surface roughening in an electrolytic solution containing 15 g/k of nitric acid at 500C. The plate was further etched with a 1% sodium hydroxide aqueous solution at 70'C to dissolve Out 1 g/M2 of aluminum, desmutted by soaking in a 10% sulfuric acid aqueous solution at 500C for 2 minutes, and then anodized in a 10% sulfuric acid aqueous solution to form 2.5 g/m 2 of an oxide layer. The thus treated aluminum plate was immersed in a 2.5% sodium silicate aqueous solution at 80C for 1 minute to obtain an aluminum substrate for a PS plate.
2) Preparation of Photosensitive Resin Composition:
Methyl methacrylate/methacrylic acid/ hydroxyphenyl methacrylate/benzyl methacrylate (50/20/10/20) Trimethylolpropane triacrylate Titanocene compound (a) described in Example 1-2 Triazine P (triazine compound produced by PANCHIM Co.):
Ccl N --t%/, N n 2"--o Ccl-I 9-Phenylacridine Coumarin Methyl ethyl ketone/toluene (712) 33 - parts parts 25 parts 7 parts 3 parts 2 parts 160 parts 3) Preparation of Printinq Plate The photosensitive resin composition was coated on the above-prepared aluminum substrate and dried to form a photosensitive resin layer having a dry thickness of 3.5 g/M2. An aqueous solution containing PVA and silicon dioxide powder (PVA/Si02/water = 7/7/86 by weight) was further coated thereon to a dry film thickness of 1.5 g/CM2 to form an overcoat layer for oxygen shielding and for excluding adverse influences of standing wave.
The resulting PS plate was imagewise scanned with an argon laser beam of 1 mj/cm2 and developed by immersion in a 0.5% sodium carbonate aqueous solution at 261C for 3 minutes. The thus formed printing pattern suffered no pattern deficiency due to corrosion with the developer and had no residual resist film on the non-exposed area. Finally, the surface of the plate was rubberized with gum arabic and postcured by exposure to 1 J/m2 of light of a metal halide lamp to complete a printing plate.
EXAMPLE 2-2
A PS plate was prepared in the same manner as in Example 2-1, except for replacing Triazine P of the photosensitive resin composition with Triazine PES (triazine compound produced by PANCHIM Co.) in the same amount. The resulting PS plate was imagewise scanned with 2.5 Mj/CM2 Of argon laser light and developed in the same manner as in Example 2-1 to obtain a satisfactory printing pattern similarly to Example 2-1. Formula of Triazine PES is as follows.
CC1 C2H50 CC1 EXAMPLE 2-3
A PS plate was prepared in the same manner as in Example 2-1, except for decreasing the amount of titanocene compound (a) of the photosensitive resin composition to 10 parts. The PS plate was imagewise scanned with 12 Mj/CM2 Of argon laser light. The resulting pattern suffered a slight loss in thickness but was free from pattern deficiencies or peeling. It is assumed that the effects of the present invention would not be produced if the amount of the titanocene compound is less than that used in this example.
COMPARATIVE EXAMPLE 2-1 A PS plate was prepared in the same manner as in Example 2-1, except for replacing Triazine P of the photosensitive resin composition with 2,4- bistrichloromethyl-6(4-styrylphenyl)-s-triazine in the same amount. The PS plate was imagewise scanned with 3.5 Mj/CM2 of argon laser light and developed in the same manner as in Example 2-1. The resulting pattern showed a large loss of the thickness in the exposed area, local pattern deficiencies, and peeling. Further, the - Further, the residual resist film was observed on part of the unexposed area.
As is apparent from Examples 2-1 to 2-3 and Comparative Example 2-1, the photosensitive resin composition containing, as a photopolymerization initiator, a triazine compound according to the present invention in combination with a titanocene compound exhibits sufficient sensitivity to argon laser light in the visible region of low energy. Since image formation on the PS plate prepared by using the photosensitive resin composition can be carried out by imagewise scanning with an argon laser beam, no film original is needed. Therefore, high precision in image formation can be attained, and the number of steps involved in plate making can be reduced.
While the invention has been described in detail and with reference to specific examples thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.
- 36
Claims (12)
1. A photosensitive resin composition comprising a polymeric binder, an ethylenically unsaturated double bond-containing monomer, and a photopolymerization initiator, in which the photopolymerization initiator is at least one compound selected from the group consisting of triazine compounds represented by formulae (I) through (V):
Xl W-<\ C (X3)3 R1 N 2 = C (X3b XI N-- C (X3) N H2 1 x2N=C (X3)3 xl N C (X3)3 R2 \ N X2 N=<C(X3)3 xl - N C (X3)3 p2-/ N /0 H-.d X2 N-\C (X3)3 37 (I) (II) (III) (IV) R3 CC1 3 / 17 ' I' 1 ---\ r 1 - i CC1 H 2C--) j4 3 (V) wherein X' and X2 each independently represents a hydrogen atom or a bromine atom; X3 represents a chlorine atom or a bromine atom; R' represents an alkyl group having f rom 1 to 3 carbon atoms or an alkoxy group having from 1 to 3 carbon atoms; R 2 represents a methylene group or a vinylene group; and R' and R 4 each independently represents a hydrogen atom or a methyl group.
2. A photosensitive resin composition as claimed in claim 1, wherein the composition further contains at least one compound selected from the group consisting of a titanocene compound and an acridine compound as a photopolymerization initiator.
3. A photosensitive resin composition as claimed in claim 1, wherein the ethylenically unsaturated double bondcontaining monomer is a polyfunctional monomer.
4. A photosensitive resin composition as claimed in claim 1, wherein the triazine compound is used in a total amount of from 0.1 to 15 parts by weight based on 100 parts of the total solids content of the photosensitive resin composition.
- 38
5. A photosensitive resin composition as claimed in claim 1, wherein at least one additive selected from the group consisting of particles of metal, particles of metal oxide and particles of plastic is added into the photosensitive resin composition in an amount of from 1 to 40 parts by weight per 100 parts by weight of the total solids content of the photosensitive resin composition.
6. A photosensitive resin composition as claimed in claim 1, wherein the polymeric binder is used in an amount of from 10 to 60 parts by weight, the ethylenically unsaturated double bond-containing monomer is used in an amount of from 20 to 70 parts by weight, and the photopolymerization initiator is used in an amount of from 0.1 to 30 parts by weight each based on 100 parts by weight of the total solids content of the photosensitive resin composition.
7. A photosensitive resin composition as claimed in claim 1, wherein alkylene glycol monoalkyl ether, alkylene glycol dialkyl ether, ketone, alcohol, or carboxylic acid ester is added as a solvent to the photosensitive resin composition.
8. A presensitized plate comprising an aluminum substrate whose surface has been mechanically and electrolytically grained, anodized, and rendered hydrophilic having provided thereon a photosensitive resin layer, in which the photosensitive resin layer comprises a photosensitive resin composition comprising a polymeric binder, an ethylenically unsaturated double bond-containing monomer, and - 39 1 a photopolymerization initiator, wherein the photopolymerization initiator is at least one compound selected from the group consisting of the triazine compounds defined in claim 1.
9. A presensitized plate as claimed in claim 8, wherein the photosensitive resin composition further contains at least one compound selected from the group consisting of a titanocene compound and an acridine compound as a photopolymerization initiator.
10. A presensitized plate as claimed in claim 8, wherein the photosensitive resin layer have provided thereon an overcoat layer mainly comprising polyvinyl alcohol.
11. A presensitized plate as claimed in claim 10, wherein the polytrinyl, alcohol has an average molecular weight of 300 to 1,000 and a degree of saponification of 70 to 90%.
12. A presensitized plate as claimed in claim 10, wherein the overcoat layer has a dry film thickness of 1 to 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32479992A JP3187569B2 (en) | 1992-11-10 | 1992-11-10 | Photosensitive resin composition and PS plate using the same |
| JP7703793A JP3263172B2 (en) | 1993-04-02 | 1993-04-02 | Photopolymerizable composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9322792D0 GB9322792D0 (en) | 1993-12-22 |
| GB2273101A true GB2273101A (en) | 1994-06-08 |
| GB2273101B GB2273101B (en) | 1997-03-05 |
Family
ID=26418133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9322792A Expired - Fee Related GB2273101B (en) | 1992-11-10 | 1993-11-05 | Photosensitive resin composition |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE4338437C2 (en) |
| GB (1) | GB2273101B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0723167A2 (en) * | 1995-01-17 | 1996-07-24 | Mitsubishi Chemical Corporation | Photopolymerizable composition for a color filter |
| US5885746A (en) * | 1994-12-29 | 1999-03-23 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive resin composition, photosensitive printing plate using the same and method of manufacturing printing master plate |
| US5908734A (en) * | 1996-07-09 | 1999-06-01 | Tokyo Ohka Kogyo Co., Ltd. | Image formation method with a post exposure heating step |
| US6010824A (en) * | 1992-11-10 | 2000-01-04 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive resin composition containing a triazine compound and a pre-sensitized plate using the same, and photosensitive resin composition containing acridine and triazine compounds and a color filter and a pre-sensitized plate using the same |
| GB2348206A (en) * | 1999-03-25 | 2000-09-27 | Murata Manufacturing Co | Photosensitive conductive paste |
| EP1510865A2 (en) * | 2003-08-28 | 2005-03-02 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition and image recording material |
| EP1779197A1 (en) * | 2004-07-05 | 2007-05-02 | LG Chem, Ltd. | Display panel includidng patterned spacer |
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| WO1981002262A1 (en) * | 1980-02-14 | 1981-08-20 | Minnesota Mining & Mfg | Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-striazine |
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| EP0313007A2 (en) * | 1987-10-23 | 1989-04-26 | Hoechst Celanese Corporation | Mixture polymerised by visible light |
| EP0379200A2 (en) * | 1989-01-19 | 1990-07-25 | Mitsubishi Kasei Corporation | Photopolymerizable composition |
| EP0503674A1 (en) * | 1991-03-15 | 1992-09-16 | Fuji Photo Film Co., Ltd. | Light-sensitive bistrihalomethyl-S-triazine compound and photopolymerizable composition containing same |
| US5219709A (en) * | 1992-02-26 | 1993-06-15 | Mitsubishi Kasei Corporation | Photopolymerizable composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH07120036B2 (en) * | 1987-07-06 | 1995-12-20 | 富士写真フイルム株式会社 | Photopolymerizable composition |
| DE4007428A1 (en) * | 1990-03-09 | 1991-09-12 | Hoechst Ag | Photopolymerisable mixt. sensitive to near UV and visible light |
| DE4013358A1 (en) * | 1990-04-26 | 1991-10-31 | Hoechst Ag | METHOD FOR THE PRODUCTION OF PRINTING FORMS OR PHOTORESISTS BY IMPROPER IRRADIATION OF A PHOTOPOLYMERIZABLE RECORDING MATERIAL |
| DE4204949A1 (en) * | 1992-02-19 | 1993-09-09 | Hoechst Ag | METHOD FOR PRODUCING A MULTICOLORED IMAGE AND LIGHT-SENSITIVE MATERIAL FOR CARRYING OUT THIS PROCESS |
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- 1993-11-05 GB GB9322792A patent/GB2273101B/en not_active Expired - Fee Related
- 1993-11-10 DE DE19934338437 patent/DE4338437C2/en not_active Expired - Fee Related
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|---|---|---|---|---|
| GB1388492A (en) * | 1971-09-03 | 1975-03-26 | Minnesota Mining & Mfg | Chromophore-substituted halomethyl-s-triazines |
| GB2029428A (en) * | 1978-08-29 | 1980-03-19 | Fuji Photo Film Co Ltd | Photosensitive resin composition giving print-out images |
| WO1981002262A1 (en) * | 1980-02-14 | 1981-08-20 | Minnesota Mining & Mfg | Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-striazine |
| GB2195121A (en) * | 1986-08-08 | 1988-03-30 | Fuji Photo Film Co Ltd | Light-sensitive composition |
| EP0313007A2 (en) * | 1987-10-23 | 1989-04-26 | Hoechst Celanese Corporation | Mixture polymerised by visible light |
| US4845011A (en) * | 1987-10-23 | 1989-07-04 | Hoechst Celanese Corporation | Visible light photoinitiation compositions |
| EP0379200A2 (en) * | 1989-01-19 | 1990-07-25 | Mitsubishi Kasei Corporation | Photopolymerizable composition |
| EP0503674A1 (en) * | 1991-03-15 | 1992-09-16 | Fuji Photo Film Co., Ltd. | Light-sensitive bistrihalomethyl-S-triazine compound and photopolymerizable composition containing same |
| US5219709A (en) * | 1992-02-26 | 1993-06-15 | Mitsubishi Kasei Corporation | Photopolymerizable composition |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6010824A (en) * | 1992-11-10 | 2000-01-04 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive resin composition containing a triazine compound and a pre-sensitized plate using the same, and photosensitive resin composition containing acridine and triazine compounds and a color filter and a pre-sensitized plate using the same |
| US5885746A (en) * | 1994-12-29 | 1999-03-23 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive resin composition, photosensitive printing plate using the same and method of manufacturing printing master plate |
| EP0723167A2 (en) * | 1995-01-17 | 1996-07-24 | Mitsubishi Chemical Corporation | Photopolymerizable composition for a color filter |
| EP0723167A3 (en) * | 1995-01-17 | 1997-04-02 | Mitsubishi Chem Corp | Photopolymerizable composition for a color filter |
| US5863678A (en) * | 1995-01-17 | 1999-01-26 | Mitsubishi Chemical Corporation | Photopolymerizable composition for a color filter |
| US5908734A (en) * | 1996-07-09 | 1999-06-01 | Tokyo Ohka Kogyo Co., Ltd. | Image formation method with a post exposure heating step |
| GB2348206A (en) * | 1999-03-25 | 2000-09-27 | Murata Manufacturing Co | Photosensitive conductive paste |
| GB2348206B (en) * | 1999-03-25 | 2001-11-07 | Murata Manufacturing Co | Photosensitive conductive paste |
| US6315927B1 (en) | 1999-03-25 | 2001-11-13 | Murata Manufacturing Co., Ltd. | Photosensitive conductive paste |
| EP1510865A2 (en) * | 2003-08-28 | 2005-03-02 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition and image recording material |
| EP1510865A3 (en) * | 2003-08-28 | 2006-06-07 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition and image recording material |
| EP1779197A1 (en) * | 2004-07-05 | 2007-05-02 | LG Chem, Ltd. | Display panel includidng patterned spacer |
| EP1779197A4 (en) * | 2004-07-05 | 2011-01-05 | Lg Chemical Ltd | Display panel includidng patterned spacer |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4338437A1 (en) | 1994-05-11 |
| DE4338437C2 (en) | 1998-11-05 |
| GB2273101B (en) | 1997-03-05 |
| GB9322792D0 (en) | 1993-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20071105 |