EP0331319B1 - Methode zur Erzeugung von Bildern - Google Patents
Methode zur Erzeugung von Bildern Download PDFInfo
- Publication number
- EP0331319B1 EP0331319B1 EP89301610A EP89301610A EP0331319B1 EP 0331319 B1 EP0331319 B1 EP 0331319B1 EP 89301610 A EP89301610 A EP 89301610A EP 89301610 A EP89301610 A EP 89301610A EP 0331319 B1 EP0331319 B1 EP 0331319B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- isothiazolinone
- compound
- formula
- hydrogen atom
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 24
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 239000000463 material Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000012545 processing Methods 0.000 claims description 25
- -1 silver halide Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 229910052709 silver Inorganic materials 0.000 claims description 14
- 239000004332 silver Substances 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000084 colloidal system Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000003780 insertion Methods 0.000 claims description 5
- 230000037431 insertion Effects 0.000 claims description 5
- UQWKODATNHLJMV-UHFFFAOYSA-N 5-chloro-1,2-thiazolidin-3-one Chemical compound ClC1CC(=O)NS1 UQWKODATNHLJMV-UHFFFAOYSA-N 0.000 claims description 3
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000243 solution Substances 0.000 description 17
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 239000000654 additive Substances 0.000 description 3
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- SMCADWLRQAABMX-UHFFFAOYSA-N 2-octyl-1,2-thiazol-5-one Chemical compound CCCCCCCCN1C=CC(=O)S1 SMCADWLRQAABMX-UHFFFAOYSA-N 0.000 description 2
- XMHYOOBGVFVBKP-UHFFFAOYSA-N 5-oxo-n-propyl-1,2-thiazole-2-carboxamide Chemical compound CCCNC(=O)N1C=CC(=O)S1 XMHYOOBGVFVBKP-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- 239000004327 boric acid Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- UEFCKYIRXORTFI-UHFFFAOYSA-N 1,2-thiazolidin-3-one Chemical class O=C1CCSN1 UEFCKYIRXORTFI-UHFFFAOYSA-N 0.000 description 1
- ADEIQWLHURSTIT-UHFFFAOYSA-N 2,4-dimethyl-1,2-thiazol-5-one Chemical compound CC1=CN(C)SC1=O ADEIQWLHURSTIT-UHFFFAOYSA-N 0.000 description 1
- AIPDJWRVGZJVNP-UHFFFAOYSA-N 2-(1-phenylethyl)-1,2-thiazol-5-one Chemical compound C1=CC(=O)SN1C(C)C1=CC=CC=C1 AIPDJWRVGZJVNP-UHFFFAOYSA-N 0.000 description 1
- WQHWPQGSJOSAKL-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)-1,2-thiazol-5-one Chemical compound CC(C)(C)CC(C)(C)N1C=CC(=O)S1 WQHWPQGSJOSAKL-UHFFFAOYSA-N 0.000 description 1
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- IYFOEVOXKZUQPJ-UHFFFAOYSA-N 5-chloro-1,2-benzothiazol-3-one Chemical compound C1=C(Cl)C=C2C(O)=NSC2=C1 IYFOEVOXKZUQPJ-UHFFFAOYSA-N 0.000 description 1
- ZRZOBPWIGRCUKG-UHFFFAOYSA-N 5-methyl-1,2-benzothiazol-3-one Chemical compound CC1=CC=C2SNC(=O)C2=C1 ZRZOBPWIGRCUKG-UHFFFAOYSA-N 0.000 description 1
- QZFIGQFIRSBAFE-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2SNC(=O)C2=C1 QZFIGQFIRSBAFE-UHFFFAOYSA-N 0.000 description 1
- XKILGFTUWYSXJN-UHFFFAOYSA-N 5-oxo-n-(2,4,4-trimethylpentan-2-yl)-1,2-thiazole-2-carboxamide Chemical compound CC(C)(C)CC(C)(C)NC(=O)N1C=CC(=O)S1 XKILGFTUWYSXJN-UHFFFAOYSA-N 0.000 description 1
- YCBOEZYEWZSOGQ-UHFFFAOYSA-N 6-ethoxy-1,2-benzothiazol-3-one Chemical compound CCOC1=CC=C2C(=O)NSC2=C1 YCBOEZYEWZSOGQ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- XEIPQVVAVOUIOP-UHFFFAOYSA-N [Au]=S Chemical compound [Au]=S XEIPQVVAVOUIOP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- ZUIVNYGZFPOXFW-UHFFFAOYSA-N chembl1717603 Chemical compound N1=C(C)C=C(O)N2N=CN=C21 ZUIVNYGZFPOXFW-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
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- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- SPZSOBPDTRBGCQ-UHFFFAOYSA-N ethyl 2-[(5-oxo-1,2-thiazole-2-carbonyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)N1C=CC(=O)S1 SPZSOBPDTRBGCQ-UHFFFAOYSA-N 0.000 description 1
- JAIYOEBQIVTKPT-UHFFFAOYSA-N ethyl 4-(5-oxo-1,2-thiazol-2-yl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1SC(=O)C=C1 JAIYOEBQIVTKPT-UHFFFAOYSA-N 0.000 description 1
- CHHJLHHGJRFBFL-UHFFFAOYSA-N ethyl N-(carbamothioylamino)-N-(carbamoylamino)carbamate Chemical compound CCOC(=O)N(NC(N)=O)NC(N)=S CHHJLHHGJRFBFL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KRJIPZXNQFELAC-UHFFFAOYSA-N n-(2-methoxyphenyl)-5-oxo-1,2-thiazole-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)N1SC(=O)C=C1 KRJIPZXNQFELAC-UHFFFAOYSA-N 0.000 description 1
- ZNSMCZOARVMOEC-UHFFFAOYSA-N n-(3-chlorophenyl)-5-oxo-1,2-thiazole-2-carboxamide Chemical compound ClC1=CC=CC(NC(=O)N2SC(=O)C=C2)=C1 ZNSMCZOARVMOEC-UHFFFAOYSA-N 0.000 description 1
- FKFKNQLYEUCBLZ-UHFFFAOYSA-N n-(3-nitrophenyl)-5-oxo-1,2-thiazole-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)N2SC(=O)C=C2)=C1 FKFKNQLYEUCBLZ-UHFFFAOYSA-N 0.000 description 1
- DQQCFCDHRUQBKM-UHFFFAOYSA-N n-(4-methoxyphenyl)-5-oxo-1,2-thiazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1SC(=O)C=C1 DQQCFCDHRUQBKM-UHFFFAOYSA-N 0.000 description 1
- WSMYMLVZEDBQGP-UHFFFAOYSA-N n-(4-nitrophenyl)-5-oxo-1,2-thiazole-2-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)N1SC(=O)C=C1 WSMYMLVZEDBQGP-UHFFFAOYSA-N 0.000 description 1
- TXMVMFWPRBUBPC-UHFFFAOYSA-N n-butyl-5-oxo-1,2-thiazole-2-carboxamide Chemical compound CCCCNC(=O)N1C=CC(=O)S1 TXMVMFWPRBUBPC-UHFFFAOYSA-N 0.000 description 1
- AZTDZKGJGAGAIP-UHFFFAOYSA-N n-dodecyl-5-oxo-1,2-thiazole-2-carboxamide Chemical compound CCCCCCCCCCCCNC(=O)N1C=CC(=O)S1 AZTDZKGJGAGAIP-UHFFFAOYSA-N 0.000 description 1
- HWLBKMSSJSIKJD-UHFFFAOYSA-N n-ethyl-5-oxo-1,2-thiazole-2-carboxamide Chemical compound CCNC(=O)N1C=CC(=O)S1 HWLBKMSSJSIKJD-UHFFFAOYSA-N 0.000 description 1
- MMPURPAEGVBSFX-UHFFFAOYSA-N n-methyl-5-oxo-1,2-thiazole-2-carbothioamide Chemical compound CNC(=S)N1C=CC(=O)S1 MMPURPAEGVBSFX-UHFFFAOYSA-N 0.000 description 1
- AIDQTRBQHWVGOF-UHFFFAOYSA-N n-methyl-5-oxo-1,2-thiazole-2-carboxamide Chemical compound CNC(=O)N1C=CC(=O)S1 AIDQTRBQHWVGOF-UHFFFAOYSA-N 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- GNHOJBNSNUXZQA-UHFFFAOYSA-J potassium aluminium sulfate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GNHOJBNSNUXZQA-UHFFFAOYSA-J 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/37—Antiseptic agents
Definitions
- the present invention relates to a method for the formation of images which is capable of rapid processing and does not cause problems such as roller transfer marks.
- the automatic processor it is advantageous also for the automatic processor to speed up the processing of X-ray films. For example, even if the processor is a compact-type automatic processor, if its processing speed is increased, its processing capacity per unit time then increases, while if its processing capacity need not be increased, then the processor can be of an even smaller size, thus contributing to space-saving.
- Rapid processing requires an increased film-transport speed but, if an automatic processor, e.g., a roller-transport-type automatic processor, is used, it tends to cause roller transfer marks on the surface of processed film.
- an automatic processor e.g., a roller-transport-type automatic processor
- gelatin fragments from the section of the leading end or trailing end of the film being processed become attached onto transport rollers, and the gelatin fragments are then transferred from the rollers onto the surface of the subsequent film, whereby the fragments appear in the form of linear stain marks in the roller transport direction.
- EP-A-238,271 discloses a silver halide photographic material comprising at least one hydrophilic colloidal layer on a support, wherein the photographic material has a water content of from 10 to 20 g/m2 upon completion of the washing step during processing with a roller transport type automatic processor.
- EP-A-308,212 discloses a method for processing a silver halide light-sensitive photographic material by a super-rapid process and also discloses an automatic processing machine for use in such a process.
- the image-wise exposed silver halide light-sensitive photographic material comprises a support and a photographic component layer provided on at least one side of the support.
- the material is processed under conditions satisfying the equation 50 ⁇ l 0.75 x T ⁇ 124 wherein l and T have the meanings given below.
- EP-A-316,864 discloses a method of processing a silver halide photographic light-sensitive material in a roller-transporting type processing equipment, comprising the steps of developing, fixing, washing and drying.
- the photographic material is comprised of a support having thereon at least one hydrophilic layer including a silver halide emulsion layer containing at least one compound selected from silver chloride, silver bromochloride and silver bromochloroiodide each containing silver chloride of not less than 60 mol% and water content of the photographic material just after the washing step is 5 to 16g/m2.
- EP-A-308,212 and EP-A-316,864 are part of the state of the art by virtue of Article 54(3) EPC.
- the present invention provides a method for the formation of images which, as a result of solving the above problems, is capable of forming images by rapid processing and which reduces roller transfer marks.
- the present invention provides a method of forming a photographic image by processing an imagewise exposed silver halide light-sensitive photographic material in an automatic processor, wherein said light-sensitive photographic material contains at least one compound of formula [I] or formula [II] below; wherein R1 is a hydrogen atom, a straight-chain or branched-chain alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, an alkylamido group, an arylamido group, an alkylthioamido group, an arylthioamido group, an alkylsulfoamido or an arylsulfoamido group; R2 and R3 are independently a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a cyano group, an alkylthio group, an arylthio group,
- FIG. 1 and Figure 2 show the constructions of the automatic processors that are used in Examples of this invention.
- Figure 3 shows the construction of the cutting machine that is used in the examples.
- the indication numbers that are used in Figures 1 and 2 are as follows: 1...the first roller at the inlet for inserting a light-sensitive material, 2...the final roller at the outlet in the drying section, 3a...developer bath, 3b...fixer bath, 3c...wash water bath, 4...a light-sensitive material, 5...squeegee section, 6...drying section, and 7...drying air outlet port.
- R1 is a hydrogen atom or a straight-chain or branched-chain alkyl, cycloalkyl, alkenyl, aralkyl, aryl, heterocyclic, alkylamido, arylamido, alkylthioamido, arylthioamido, alkylsulfoamido or arylsulfoamido group; and R2 and R3 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a cyano group, an alkylthio group, an arylthio group, an alkylsulfoxido group, an alkylsulfonyl group, an alkylsulfinyl group or a heterocyclic group, such that the above alkyl
- Compounds of Formula I can be synthesised by the method disclosed in EP-1,555,415; wherein R4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydroxymethyl group; and R5 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; such that the above-mentioned groups for R4 and R5 may independently be substituted and provided that the compound of formula II is not 1,1-dimethylol-1-bromo-1-nitromethane.
- Compounds of formula II may be synthesised by referring to: Henry, Recueil destician chimiques des Ray-Bas, 16 251.
- R6 represents a hydrogen atom, an alkyl group or an alkoxy group
- R7, R8, and R9 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group or a nitro group
- R10 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a -CONHR13 group (wherein R13 is an alkyl, aryl, alkylthio, arylthio, alkylsulfonyl or arylsulfonyl group) or a heterocyclic group
- R11 and R12 each represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group,
- Benzoisothiazoline-3-one 2-methyl-benzoisothiazoline-3-one, 2-ethyl-benzoisothiazoline-3-one, 2-(n-propyl)-benzoisothiazoline-3-one, 2-(n-butyl)-benzoisothiazoline-3-one, 2-(sec-butyl)-benzoisothiazoline-3-one, 2-(t-butyl)-benzoisothiazoline-3-one, 2-methoxy-benzoisothiazoline-3-one, 2-ethoxy-benzoisothiazoline-3-one, 2-(n-propyloxy)-benzoisothiazoline-3-one, 2-(butyloxy)-benzoisothiazoline-3-one, 5-chloro-benzoisothiazoline3-one, 5-methyl-benzoisothiazoline-3-one, 6-ethoxy-benzoisothiazoline-3-one, 6-cyano-benzoisothiazoline-3-one
- the number of carbon atoms of each of the alkyl group and alkenyl group is generally 1 to 36, and more preferably 1 to 18.
- the number of carbon atoms of the cycloalkyl group is generally 3 to 12, and more preferably 3 to 6.
- Each of the alkyl, cycloalkyl, alkenyl, aralkyl, aryl and heterocyclic groups represented by the R10 may have a substituent which may be selected from among halogen atoms and groups including nitro, cyano, thiocyano, aryl, alkoxy, aryloxy, carboxy, sulfoxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, acyloxy, sulfamoyl, carbamoyl, acylamino, diacylamino, ureido, thioureido, urethane, thiourethane, sulfonamido, heterocyclic, arylsulfonyloxy, alkylsulfonyloxy, arylsulfonyl, alkylsulfonyl, arylthio, alkylthio,
- the number of carbon atoms of the alkyl group represented by the R11 or R12 is generally 1 to 18, and more preferably 1 to 9, and that of the cycloalkyl group represented by the same is generally 3 to 18, and more preferably 3 to 6.
- Each of these groups represented by the R11 or R12 may have a substituent, which is, for example, a halogen atom or a nitro, sulfo, aryl or hydroxy group.
- 2-(N-methylcarbamoyl)-3-isothiazolinone 5-methyl-2-(N-methylcarbamoyl)-3-isothiazolinone, 2-(N-methylthiocarbamoyl)-3-isothiazolinone, 4-bromo-5-methyl-2-(N-methylcarbamoyl)-3-isothiazolinone, 4-cyano-5-methylthio-2-(N-methylcarbamoyl)-3-isothiazolinone, 4-cyano-5-methylsulfinyl-2-(N-methylcarbamoyl)-3-isothiazolinone, 4-cyano-5-methylsulfonyl-2-(N-methylcarbamoyl)-3-isothiazoline, 2-(N-n-butylcarbamoyl)-3-isothiazolinone, 2-(N-t-octylcarbamoyl)-3-isothiazolinone, 5-
- any of these 1,2-benzoisothiazoline-3-one compounds of Formula [III] to be used in this invention is generally contained in said photographic material in a proportion of 1x10 ⁇ 5 to 10% by weight relative to the total amount of hydrophilic colloid contained in the photographic material, and particularly preferably from 1x10 ⁇ 4 to 1% by weight relative to the total amount of hydrophilic colloid contained in the photographic material.
- any of these isothiazoline-3-one compounds of Formula [IV] is generally contained in said photographic material in a proportion of from 1x10 ⁇ 4 to 10% by weight relative to the total amount of hydrophilic colloid contained in the photographic material, and particularly preferably from 3x10 ⁇ 4 to 1% by weight relative to the total amount of hydrophilic colloid contained in the photographic material. It goes without saying that the amount of these compounds added is allowed to be outside the range mentioned above, depending on, for example, the kind of light-sensitive material to be used, the layer to which the compound is to be added and coating method.
- any of these compounds may be dissolved into water or a solvent, not adversely affecting photographic characteristics; suitable organic solvents include alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, glycols such as ethylene glycol and propylene glycol, esters such as ethyl acetate, and the solution may be added to a hydrophilic colloid, may be coated on the protective layer, or may be incorporated into a photographic light-sensitive material by immersing the photographic light-sensitive material into the solution.
- suitable organic solvents include alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, glycols such as ethylene glycol and propylene glycol, esters such as ethyl acetate, and the solution may be added to a hydrophilic colloid, may be coated on the protective layer, or may be incorporated into a photographic light-sensitive material by immersing the photographic light-sensitive material into the solution.
- the compound may be dissolved into a high-boiling solvent, a low-boiling solvent or a mixture of these solvents, then emulsifiedly dispersed in the presence of a surface active agent, and then added to a liquid containing a hydrophilic colloid or coated over the protective layer.
- the compound may be incorporated into a high-polymer compound such as butyl polyacrylate, then dispersed in the presence of a surface active agent, and the dispersed liquid is then added to a liquid containing a hydrophilic colloid or coated over the protective layer.
- the above l can be found on the basis of, e.g., a light-sensitive material comprising a 175 ⁇ m-thick polyethylene terephthalate support having photographic component layers thereon.
- T implies the whole period of time the leading end of a sheet of film takes to travel from the insertion of it in the first roller at the film inlet, passing through the developer bath, crossover section, fixer bath, crossover section, wash water bath, crossover section and drying section, until the ejection of it from the final roller at the film outlet in the drying section of an automatic processor; in other words, the quotient (sec.) obtained by dividing the whole length (in meters) of the processing line by the line transport speed (meters/sec.).
- crossover section passage time is included, well-known to those skilled in the art, is that even in the crossover section, substantial processing is considered to be still going on due to the preceding process' liquid contained in the swelled gelatin layer of the film in transit.
- the whole number of the transport rollers of the automatic processor for use in the image forming method of this invention when expressed in terms of the value obtained dividing the l, the whole processing line's length of the automatic processor, by the number of the rollers, is desirable to be in the range of from 0.01 to 0.04. Also, the processing time proportions and ranges required in the individual processing positions are desired to be as follows: Insertion + developing + crossover: 25 to 40% Fixing + crossover: 12 to 25% Washing + crossover: 10 to 25% Squeeze + drying: 25 to 45% Total 100 %
- each roller to be used in its transport-functional part, is desirable to be 12mm to 60mm in diameter and 30cm to 110cm in length.
- the roller may be made of various materials; for example, bakelite-type materials which may contain glass powder, metal powder or plastic powder) or rubber-type materials (e.g., neoprene, isoprene, silicone rubber) may be used for the rollers in the developing, fixing, washing and drying sections, and repellent and elastic silicone rubber or highly water-absorbing synthetic leather such as the commercial product called 'Kurarino' (Kuraray Co., Ltd.) may be preferably used for the rollers in the crossover and squeeze sections.
- bakelite-type materials which may contain glass powder, metal powder or plastic powder
- rubber-type materials e.g., neoprene, isoprene, silicone rubber
- repellent and elastic silicone rubber or highly water-absorbing synthetic leather such as the commercial product called 'Kurarino' (Kuraray Co., Ltd.) may be preferably
- the above l is in the range of from 0.7m to 3.1m so that satisfactory results can be obtained. If the l is less than 0.7m, the individual processes become small with the number of the rollers to be used being reduced, thus reducing the sensitivity of or affecting the transportability of the light-sensitive material being processed. In contrast, if the l is larger than 3.1m, the transport speed is increased to excess, whereby not only is the film liable to get scratched but the durability of the automatic processor deteriorates abruptly.
- the product of l 0.75 and T is less than 50, the sensitivity of the film in processing is abruptly lowered, and, in a film containing not less than 10mg/m2 of a sensitizing dye per side of its support, the residual dye stain also becomes a problem.
- the product of l 0.75 and T should be not less than 76.
- various additives may be added to the developer solution and fixer solution to be used in the automatic processor.
- Typical additives to be added to the developer solution include an antifoggant; a development accelerator comprised of an alkali agent such as sodium hydroxide, sodium carbonate or potassium carbonate; an inorganic or organic restrainer such as potassium bromide, 2-methylbenzimidazole or methylbenzothiazole; a water softener such as a polyphosphate; and an anti-surface-overdevelopement agent comprising a small amount of an iodide or mercapto compound.
- a development accelerator comprised of an alkali agent such as sodium hydroxide, sodium carbonate or potassium carbonate
- an inorganic or organic restrainer such as potassium bromide, 2-methylbenzimidazole or methylbenzothiazole
- a water softener such as a polyphosphate
- an anti-surface-overdevelopement agent comprising a small amount of an iodide or mercapto compound.
- a preservative such as a sulfite; a buffer such as a carbonate, boric acid, a borate or an alkanolamine; an alkali agent such as a hydroxide or a carbonate; a dissolving aid such as polyethylene glycol or an ester thereof; a pH control agent comprised of an organic acid such as acetic acid; a sensitizer such as a quaternary ammonium salt; or a surface active agent, for example, may be used.
- the developer solution may contain a hardening agent.
- a hardening agent a dialdehyde-type hardening agent may be suitably used.
- the developer solution may also contain a chelating agent such as, e.g.. ethylenediaminetetraacetic acid or an alkali metal salt thereof, a polyphosphate or a nitriloacetate.
- a chelating agent such as, e.g.. ethylenediaminetetraacetic acid or an alkali metal salt thereof, a polyphosphate or a nitriloacetate.
- the developing temperature is generally determined in relation to the developing time.
- the developing temperature and developing time are preferably 30 to 40°C and 6 to 20 seconds, respectively.
- the fixer bath to be used in the fixing process of this invention is generally an aqueous solution containing, e.g., a thiosulfate and a water-soluble aluminum compound, and the solution may also contain a polybasic acid such as citric acid, or tartaric acid, and its pH is preferably about 3.5 to 5.0 (at 20°C).
- a polybasic acid such as citric acid, or tartaric acid
- the developing process may be followed by a stop process.
- the stop process is excluded from general roller-transport-type automatic processors, so that part of the developer solution is carried out into the fixer solution, whereby the pH of the fixer solution may sometimes be raised.
- the pH of the fixer solution is preferably adjusted to 3.6 to 4.7 (at 20°C).
- a thiosulfate such as ammonium thiosulfate or sodium thiosulfate is generally used. Of these ammonium thiosulfate is particularly suitably used from the fixing speed point of view.
- the amount of the fixing agent although allowed to be arbitrarily varied, is normally from 0.1 to 5 moles per liter.
- a water-soluble aluminum salt may be used which functions principally as a hardening agent in the fixer solution.
- This is a compound which is generally known as a hardening agent for acid hardening fixing solutions, and examples of it include aluminum chloride, aluminum sulfate and potassium alum.
- the fixing temperature and time in this invention are preferably 20° to 35°C and 4 to 15 seconds, respectively.
- a photographic material that has been developed and fixed is generally washed and then dried.
- the washing takes place in order to almost completely remove the silver salt that has been dissolved by fixing, and is preferably carried out for a period of 5 to 12 seconds at 20° to 50°C.
- the drying is to take place at a temperature of 40° to 100°C for an appropriate period of time.
- the drying time although allowed to be arbitrarily varied according to ambient conditions, is normally from 5 to 15 seconds.
- roller-transport-type automatic processor suitably usable in practicing this invention are given in Figure 1 and Figure 2.
- 1 is the first roller at the film inlet in the insertion section
- 2 is the final roller at the film outlet in the drying section
- 3a is a developer bath
- 3b is a fixer bath
- 3c is a wash water bath
- 4 is a light-sensitive material to be processed
- 5 is a squeegee section
- 6 is a drying section
- 7 is a drying air outlet port.
- a silver iodobromide emulsion of which the average silver iodide content is 2.0 mole% was subjected to gold-sulfur sensitization by using a chloroaurate, sodium thiosulfate and ammonium thiocyanate, stabilized by using 4-hydroxy-6-methyl-1,3,3a,7-tetrazaindene, and spectrally sensitized by using the following Sensitizing Dyes A and B:
- an emulsion liquid (silver halide coating liquid).
- the following adding amounts are values per mole of silver halide.
- a protective layer coating liquid containing matting agents comprised of 1g/liter of polymethyl methacrylate having an average particle size of 3.5 ⁇ m and 30g/liter of colloidal silica and the following compounds as surface active agents was prepared.
- the thus prepared emulsion and the protective layer coating liquid were coated simultaneously, in the order of the emulsion layer and protective layer from the support side, at a coating speed of 90m/min on both sides of a 175 ⁇ m-thick polyethylene terephthalate film support, both sides of which were subbed with an aqueous copolymer-dispersed liquid obtained by diluting to 10% by weight a copolymer comprised of three different monomers: 50% by weight of glycidyl methacrylate, 10% by weight of methyl acrylate, and 40% by weight of butyl methacrylate, whereby samples No.1 through No.33 were obtained.
- the coating weight of silver of each sample was 40mg/dm2.
- the gelatin coating weight of the emulsion layer was 2.0g/m2, and that of the protective layer was 1.0g/m2.
- the gelatin that was used in each layer was lime-treated Ossein gelatin.
- each sample was cut into pieces by the cutting machine shown in Figure 3, wherein A1 and A2 indicate cutting blades, and B indicates a light-sensitive material (sample). Evaluation of the roller transfer marks on each sample was made by expressing in terms of the difference ⁇ D between the densities, measured by an automatic densitometer, of the roller transfer marks and of their ambient areas.
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Photographic Processing Devices Using Wet Methods (AREA)
Claims (6)
- Verfahren zur Erzeugung eines photographischen Bildes durch Behandeln eines bildgerecht belichteten lichtempfindlichen photographischen Silberhalogenid-Aufzeichnungsmaterials in einer automatischen Behandlungsvorrichtung, wobei das lichtempfindliche photographische Aufzeichnungsmaterial mindestens eine Verbindung der Formel [I] oder der Formel [II]
worin bedeuten:
R₁ ein Wasserstoffatom, eine gerad- oder verzweigtkettige Alkylgruppe, eine Cycloalkylgruppe, eine Alkenylgruppe, eine Aralkylgruppe, eine Arylgruppe, eine heterocyclische Gruppe, eine Alhylamidogruppe, eine Arylamidogruppe, eine Alkylthioamidogruppe, eine Arylthioamidogruppe, eine Alkylsulfoamido- oder eine Arylsulfoamidogruppe;
R₂ und R₃ unabhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine Alkylgruppe, eine Cycloalkylgruppe, eine Arylgruppe, eine Cyanogruppe, eine Alkylthiogruppe, eine Arylthiogruppe, eine Alkylsulfoxidgruppe, eine Alkylsulfonylgruppe, eine Alkylsulfinylgruppe oder eine heterocyclische Gruppe, wobei die zuvor genannten Alkyl-, Cycloalkyl-, Alkenyl-, heterocyclischen, Aralkyl- und Arylgruppen substituiert sein können und wobei R₂ und R₃ zusammen eine einen Ring vervollständigende zweiwertige Gruppe bilden können, mit Ausnahme von 5-Chlorisothiazolin-3-on; worin bedeuten:
R₄ ein Wasserstoffatom, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatom(en) oder eine Hydroxymethylgruppe und R₅ ein Wasserstoffatom oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatom(en), wobei die zuvor genannten Gruppen R₄ und R₅ substituiert sein können, ausschließlich 1,1-Dimethylol-1-brom-1-nitromethan,
enthält und die Behandlung unter der folgenden Gleichung:
worin bedeuten:
l die Länge (in m) zwischen der Achse der ersten Walze am Filmeinlaß im Einführabschnitt und der Achse der letzten Walze am Filmauslaß in dem Trocknungsabschnitt einer automatischen Behandlungsvorrichtung mit Walzentransport in der Größenordnung von mehr als 0,7 und weniger als 3,1 m und
T die Zeit (in s), die das lichtempfindliche photographische Silberhalogenid-Aufzeichnungsmaterial zum Durchtritt durch die Länge l benötigt,
genügenden Bedingungen erfolgt. - Verfahren nach Anspruch 1, wobei die Verbindung der Formel [I] aus einer 1,2-Benzoisothiazolin-3-on-Verbindung der Formel [III] oder einer Isothiazolin-3-on-Verbindung der Formel [IV] besteht:
worin bedeuten:
R₆ ein Wasserstoffatom, eine Alkylgruppe oder eine Alkoxygruppe;
R₇, R₈ und R₉ unabhängig voneinander ein Halogenatom, eine Alkylgruppe, eine Alkoxygruppe, eine Cyanogruppe oder eine Nitrogruppe, wobei die zuvor genannten Gruppen R₆, R₇, R₈ und R₉ substituiert sein können; worin bedeuten:
R₁₀ ein Wasserstoffatom, eine Alkylgruppe, eine Cycloalkylgruppe, eine Alkenylgruppe, eine Aralkylgruppe, eine Arylgruppe, eine -CONHR₁₃-Gruppe oder eine heterocyclische Gruppe, wobei R₁₃ für eine Alkylgruppe, eine Arylgruppe, eine Alkylthiogruppe, eine Arylthiogruppe, eine Alkylsulfonylgruppe oder eine Arylsulfonylgruppe steht, wobei die zuvor genannten Gruppen R₁₀ substituiert sein können;
R₁₁ und R₁₂ unabhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine Alkylgruppe, eine Cycloalkylgruppe, eine Arylgruppe, eine heterocyclische Gruppe, eine Cyanogruppe, eine Alkylthiogruppe, eine Arylthiogruppe, eine Alkylsulfoxidgruppe, eine Alkylsulfinylgruppe oder eine Alkylsulfonylgruppe, wobei die zuvor genannten Gruppen R₁₁ und R₁₂ substituiert sein können. - Verfahren nach Anspruch 2, wobei die 1,2-Benzoisothiazolin-3-on-Verbindung der Formel [III] in dem photographischen Aufzeichnungsmaterial in einer Menge von 1 x 10⁻⁵ bis 10 Gew.-%, bezogen auf die Gesamtmenge an in dem photographischen Aufzeichnungsmaterial enthaltenem hydrophilen Kolloid vorhanden ist.
- Verfahren nach Anspruch 3, wobei der Gehalt an der Verbindung 1 x 10⁻⁴ bis 1 Gew.-% beträgt.
- Verfahren nach einem der Ansprüche 2 bis 4, wobei die Thiazolin-3-on-Verbindung der Formel [IV] in dem photographischen Aufzeichnungsmaterial in einer Menge von 1 x 10⁻⁴ bis 10 Gew.-%, bezogen auf die Gesamtmenge an in dem photographischen Aufzeichnungsmaterial enthaltenem hydrophilen Kolloid vorhanden ist.
- Verfahren nach Anspruch 5, wobei der Gehalt der Verbindung 3 x 10⁻⁴ bis 1 Gew.-% beträgt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP37717/88 | 1988-02-20 | ||
| JP63037717A JP2613415B2 (ja) | 1988-02-20 | 1988-02-20 | 画像形成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0331319A1 EP0331319A1 (de) | 1989-09-06 |
| EP0331319B1 true EP0331319B1 (de) | 1994-01-26 |
Family
ID=12505266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89301610A Expired - Lifetime EP0331319B1 (de) | 1988-02-20 | 1989-02-20 | Methode zur Erzeugung von Bildern |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0331319B1 (de) |
| JP (1) | JP2613415B2 (de) |
| DE (1) | DE68912619T2 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6911302B2 (en) | 2002-07-11 | 2005-06-28 | Eastman Kodak Company | Coating composition for photographic materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2786889B1 (fr) | 1998-12-03 | 2001-02-02 | Eastman Kodak Co | Procede pour empecher la croissance des micro-organismes dans les dispersions photographiques |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0238271A2 (de) * | 1986-03-13 | 1987-09-23 | Konica Corporation | Photographisches Silberhalogenidmaterial und Verfahren zu dessen Behandlung |
| EP0316864A2 (de) * | 1987-11-17 | 1989-05-24 | Konica Corporation | Lichtempfindliches photographisches Silberhalogenidmaterial und Verfahren zur Behandlung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5848892B2 (ja) * | 1977-08-03 | 1983-10-31 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料用親水性コロイドの防腐方法 |
| JPS59226343A (ja) * | 1983-06-07 | 1984-12-19 | Konishiroku Photo Ind Co Ltd | 写真用コロイド銀水性組成物の防腐方法 |
| JPS60119547A (ja) * | 1983-12-01 | 1985-06-27 | Konishiroku Photo Ind Co Ltd | 写真用水性分散液組成物の防腐方法 |
| JPS62105138A (ja) * | 1985-10-31 | 1987-05-15 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料の処理方法 |
| US5081007A (en) * | 1987-09-15 | 1992-01-14 | Konica Corporation | Method for processing a silver halide light-sensitive photographic material and an automatic processor therefor |
-
1988
- 1988-02-20 JP JP63037717A patent/JP2613415B2/ja not_active Expired - Fee Related
-
1989
- 1989-02-20 DE DE1989612619 patent/DE68912619T2/de not_active Expired - Fee Related
- 1989-02-20 EP EP89301610A patent/EP0331319B1/de not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0238271A2 (de) * | 1986-03-13 | 1987-09-23 | Konica Corporation | Photographisches Silberhalogenidmaterial und Verfahren zu dessen Behandlung |
| EP0316864A2 (de) * | 1987-11-17 | 1989-05-24 | Konica Corporation | Lichtempfindliches photographisches Silberhalogenidmaterial und Verfahren zur Behandlung |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6911302B2 (en) | 2002-07-11 | 2005-06-28 | Eastman Kodak Company | Coating composition for photographic materials |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2613415B2 (ja) | 1997-05-28 |
| DE68912619T2 (de) | 1994-05-26 |
| DE68912619D1 (de) | 1994-03-10 |
| EP0331319A1 (de) | 1989-09-06 |
| JPH01213659A (ja) | 1989-08-28 |
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