US3740221A - Development of photographic material - Google Patents
Development of photographic material Download PDFInfo
- Publication number
- US3740221A US3740221A US00078919A US3740221DA US3740221A US 3740221 A US3740221 A US 3740221A US 00078919 A US00078919 A US 00078919A US 3740221D A US3740221D A US 3740221DA US 3740221 A US3740221 A US 3740221A
- Authority
- US
- United States
- Prior art keywords
- pyrazolidinone
- developing
- aryl
- hydroxylamine
- bath
- 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
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- 239000000463 material Substances 0.000 title description 19
- 229910052709 silver Inorganic materials 0.000 abstract description 30
- 239000004332 silver Substances 0.000 abstract description 30
- 239000003795 chemical substances by application Substances 0.000 abstract description 27
- -1 SILVER HALIDE Chemical class 0.000 abstract description 25
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 22
- 239000000203 mixture Substances 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 description 13
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 5
- 150000002443 hydroxylamines Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004133 Sodium thiosulphate Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 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
- 238000005406 washing Methods 0.000 description 3
- JIPBZEFOQFUCIQ-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-4,4-dimethylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)CN1C1=CC=C(O)C=C1 JIPBZEFOQFUCIQ-UHFFFAOYSA-N 0.000 description 2
- SAQHUYUDATUGDI-UHFFFAOYSA-N 4,4-diethyl-1-(4-methoxyphenyl)pyrazolidin-3-one Chemical compound N1C(=O)C(CC)(CC)CN1C1=CC=C(OC)C=C1 SAQHUYUDATUGDI-UHFFFAOYSA-N 0.000 description 2
- YKYMNPPYHHBLGC-UHFFFAOYSA-N 4,4-dimethyl-1-(4-methylphenyl)-5-propan-2-yloxypyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)C(OC(C)C)N1C1=CC=C(C)C=C1 YKYMNPPYHHBLGC-UHFFFAOYSA-N 0.000 description 2
- BOICYHPBHGWXHQ-UHFFFAOYSA-N 4,4-dimethyl-1-phenyl-5-phenylmethoxypyrazolidin-3-one Chemical compound C=1C=CC=CC=1N1NC(=O)C(C)(C)C1OCC1=CC=CC=C1 BOICYHPBHGWXHQ-UHFFFAOYSA-N 0.000 description 2
- NSGIHDIFHBJPRZ-UHFFFAOYSA-N 5-butoxy-4,4-dimethyl-1-(4-methylphenyl)pyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)C(OCCCC)N1C1=CC=C(C)C=C1 NSGIHDIFHBJPRZ-UHFFFAOYSA-N 0.000 description 2
- CIAAMEWBOHUULM-UHFFFAOYSA-N 5-methoxy-4,4-dimethyl-1-(4-methylphenyl)pyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)C(OC)N1C1=CC=C(C)C=C1 CIAAMEWBOHUULM-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- WEZYZKZCABUSRJ-UHFFFAOYSA-N n,n-diethylhydroxylamine;oxalic acid Chemical compound CCN(O)CC.OC(=O)C(O)=O WEZYZKZCABUSRJ-UHFFFAOYSA-N 0.000 description 2
- YERGVOHOBQDWPR-UHFFFAOYSA-N n-[4-(4,4-diethyl-3-oxopyrazolidin-1-yl)phenyl]acetamide Chemical compound N1C(=O)C(CC)(CC)CN1C1=CC=C(NC(C)=O)C=C1 YERGVOHOBQDWPR-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 description 1
- MTJVRSKTTYDZBP-UHFFFAOYSA-N 4,4-dimethyl-1-(4-methylphenyl)-5-phenylmethoxypyrazolidin-3-one Chemical compound C1=CC(C)=CC=C1N1C(OCC=2C=CC=CC=2)C(C)(C)C(=O)N1 MTJVRSKTTYDZBP-UHFFFAOYSA-N 0.000 description 1
- PHEGOFFINWTBQQ-UHFFFAOYSA-N 4,4-dimethyl-1-(4-methylphenyl)-5-propoxypyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)C(OCCC)N1C1=CC=C(C)C=C1 PHEGOFFINWTBQQ-UHFFFAOYSA-N 0.000 description 1
- SJSJAWHHGDPBOC-UHFFFAOYSA-N 4,4-dimethyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)CN1C1=CC=CC=C1 SJSJAWHHGDPBOC-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- XPAZGLFMMUODDK-UHFFFAOYSA-N 6-nitro-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N=CNC2=C1 XPAZGLFMMUODDK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 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
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/04—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
- G03C8/06—Silver salt diffusion transfer
Definitions
- R is aryl, R and R are hydrogen, alkyl, aralkyl or aryl, and R is hydrogen, alkyl, alkoxy, aralkoxy or aryloxy.
- the 1-aryl-3-pyrazolidinone compound exhibits a superadditive effect on the hydroxylamine developing agent.
- This invention relates to the development of photographic materials containing exposed silver halide, to new developing combinations and to photographic materials and solutions containing such combinations.
- hydroxylamine and derivatives thereof of which the oxidation products have the favourable property of leaving no residual stain in the silver image obtained has been disclosed amongst others in United States patent specification 2,857,276 of Edwin H. Land and Helen J. Tracy, issued Oct. 21, 1958.
- hydroxylamine derivatives that have been proposed for use as silver halide develop- Patented June 19, 1973 ing agents and of which the development activity is higher than that of the N,N-dialky-l hydroxylamines include for example arninoalkyl hydroxylamines, more especially N,N-dialkylhydroxylamines having in at least one of the N-alkyl groups an intralinear amino nitrogen atom, either cyclic or acyclic, examples of which can be found in United States patent specification 3,287,125 of Milton Green, Adnan A. Sayigh and Henri Ulrich, issued Nov.
- alkoxyhydroxylamines more especially N,N- dialkylhydroxylamines of which at least one of the N-alkyl groups is substituted by alkoxy or alkoxyalkoxy, examples of which can be found in United States patent specification 3,293,034 of Milton Green, Adnan A. Sayigh and Henri Ulrich, issued Dec. 20, 1966 and sulphone hydroxylamines, more especially N,N-dialkylhydroxylamines having in at least one of the N-alkyl groups an intralinear sulphonyl (SO group, examples of which can be found in United States patent specification 3,287,124 of Milton Green, Adnan A. Sayigh and Henri Ulrich, issued Nov. 22, 1966.
- SO group examples of which can be found in United States patent specification 3,287,124 of Milton Green, Adnan A. Sayigh and Henri Ulrich, issued Nov. 22, 1966.
- N,N-dialkylhydroxylamines having in at least one of the N-alky'l groups a quaternary ammonium group either cyclic or acyclic which excel by their high development activity have been proposed for use as silver halide developing agents in the co-pending application filed on even date herewith for Novel Photographic Developers assigned U.S. Ser. No. 78,916.
- the 1-aryl-3-pyrazolidinone compounds having a superadditive development effect with hydroxylamine developing agents can be represented by the following general formula:
- a process of making photographic records which comprises treating a photographic material having layers containing developable silver salts with an aqueous alkaline solution in the presence of a hydroxylamine developing agent and an 1-aryl-3-pyrazolidinone compound is described above.
- the invention also includes developer compositions comprising in addition to a hydroxylamine developing agent, an l-aryl-3-pyrazolidinone compound as described.
- hydroxylamine developing agent it is intended to embrace hydroxylamine itself as well as derivatives thereof as described above.
- the 1-aryl-3-pyrazolidinones of use according to the present invention may be added to the developing bath or to the emulsion or to both simultaneously.
- Developer compositions that comprise the superadditive developing agents according to the present invention may comprise in addition thereto any of the common ingredients employed in developing compositions e.g. alkalies such as sodium hydroxyde, potassium hydroxide, sodium carbonate, trisodium phosphate, etc., silver halide solvents such as sodium thiosulphate, preservatives such as sulphites, bisulphites, metabisulphites and acids such as 'boric acid, and citric acid.
- alkalies such as sodium hydroxyde, potassium hydroxide, sodium carbonate, trisodium phosphate, etc.
- silver halide solvents such as sodium thiosulphate
- preservatives such as sulphites, bisulphites, metabisulphites and acids such as 'boric acid, and citric acid.
- developer composition may comprise potassium bromide and watersoftening agents such as polyphosphates and derivatives of ethylene diamine tetraacetic acid, antifoggants such as benzotriazole, S-nitrobenzotriazole and 6-nitrobenzimidazole, and wetting agents as well as other compounds known in the photographic development technique such as development restrainers and development accelerators.
- potassium bromide and watersoftening agents such as polyphosphates and derivatives of ethylene diamine tetraacetic acid
- antifoggants such as benzotriazole, S-nitrobenzotriazole and 6-nitrobenzimidazole
- wetting agents as well as other compounds known in the photographic development technique such as development restrainers and development accelerators.
- the ratio of hydroxylamine developing agent to l-aryl- 3-pyrazolidinone compound used in the present invention can be chosen in such a way that the combination is suited for the development of all kinds of materials including materials having silver chloride emulsion layers of low sensitivity as Well as materials having highly sensitive silver bromo-iodide emulsion layers. This ratio may vary within wide limits and also depends on the particular hydroxylamine developing agent used. In most cases the ratio is chosen in such a way that the amount of the hydroxylamine developing agent strongly outweghts the 1-aryl-3-pyrazolidinone compound.
- a strong superadditive effect is obtained by using an amount of 0.05 millimole to 10 millimole, preferably from 0.3 millimole to 6 millimole, of 1-aryl-3-pyraZolidinone to an amount of 10 to 100 millimole of hydroxylamine developing agent, per litre of developing composition.
- an amount of 0.05 millimole to 10 millimole preferably from 0.3 millimole to 6 millimole
- 1-aryl-3-pyraZolidinone to an amount of 10 to 100 millimole of hydroxylamine developing agent, per litre of developing composition.
- larger amounts of said 1-aryl-3-pyrazolidinone compounds can be used, although the superadditive effect obtained with higher concentrations is not more considerable.
- novel combination of developing agents of the invention may be used in conventional or wet development of silver halide emulsions, in diffusion transfer processes, both dye and silver, in such photographic processes known as stabilization processing wherein it is desired to eliminate or minimize the need for washing or stabilizng operatons in liquid baths subsequent to the formation of the silver print, etc.
- an exposed silver halide emulsion is treated with a liquid processing composition while in superposed relationship with an image-receiving material.
- the exposed silver halide is developed to silver and the unexposed silver halide is converted into a complex silver salt which is transferred to the image-receiving material and there reduced to silver to form a positive print.
- the processing composition normally includes a silver halide solvent, such as sodium thiosulphate, which forms with silver halide a soluble complex as is well known in the art of forming silver images by transfer, and may also include a film-forming material such as sodium cal-boxymethyl cellulose or hyroxyethyl cellulose, starch or gum for increasing the viscosity of the composition, as, for instance, in the case of in-camera silver complex diffusion transfer processing.
- a silver halide solvent such as sodium thiosulphate
- a film-forming material such as sodium cal-boxymethyl cellulose or hyroxyethyl cellulose, starch or gum for increasing the viscosity of the composition, as, for instance, in the case of in-camera silver complex diffusion transfer processing.
- the developing agents of use according to the invention may be employed in solution or they may be initially incorporated in a layer of the photosensitive material, e.g. a silver halide emulsion layer or other colloid layer in water-permeable relationship therewith. In silver complex diffusion transfer processes they may also be incorporated in a layer of the image-receiving material which, during processing, is in supperposed relationship with the photosensitive silver halide material.
- the developing agents When the developing agents are incorporated into the materials to be processed it is possible to limit the processing liquid to a simple aqueous alkaline solution. It is also possible, of course, to incorporate only the 1-aryl-3-pyrazolidinone developing agents into the materials to be processed and to employ the hydroxylamine developing agent in the processing liquid or vice versa.
- EXAMPLE 1 Strips of a photographic material comprising a lightsensitive silver halide emulsion layer coated on a cellulose-triacetate support are exposed through a grey filter with a light-quantity (E) which corresponds to the shoulder part of the density/ log E curve.
- E light-quantity
- Each of the exposed strips is developed at 20 C. in a separate developing bath.
- One of them is developed in a bath A containing as developing agent only hydroxylamine hydrochloride and having the following composition:
- EXAMPLE 2 This example is analogous to Example 1, with the only difference that now a developing bath B is used according to the co-pending application filed on even date herewith for Novel Photographic Developers.
- EXAMPLE 5 This example is analogous to Example l, with the difference that now a developing bath E is used which Densities obtained after a developing time of- Developing bath 0 see. 20 sec. 1 min. 3 min. 5 min.
- 56 3 0 plus 1.264. g. (4.27 mmole) of Comound 9 0. 04 0. 30 1. 00 2.
- a photosensitive element was prepared comprising on a paper support a silver bromoiodide emulsion layer containing per kg. an amount of silver halide corresponding to 60 g. of silver nitrate.
- the photosensitive element and an image-receiving element which comprises a silver recep tive layer containing development nuclei dispersed in a matrix of colloidal silica coated on a water-impervious support according to the practice: described in United 7 States patent specification 2,823,122 of Edwin H. Land, issued Feb. 11, 1958, were advanced in susperposed relationship between a pair of pressure applying rollers to spread between them in a thin layer the following processing composition:
- Photographic developing method which comprises developing an exposed silver halide emulsion layer of a photographic material with an aqueous alkaline composition in the presence of a hydroxylamine developing agent and a l-aryl-3-pyrazolidinone compound corresponding to the formula:
- R stands for an aryl group
- each of R and R stands for hydrogen, alkyl, aralkyl or aryl
- R stands for hydrogen, alkyl, alkoxy, aralkoxy or aryloxy.
- Photographic developing method according to claim 1, wherein said method is used for making images according to the silver complex diffusion transfer process.
- Photographic developing method according to claim 1, wherein said hydroxylamine developing agent and said 1-aryl-3-pyrazolidinone compound are both present in the said aqueous composition.
- Photographic developing composition for developing an exposed silver halide emulsion layer of a photographic material comprising in aqueous alkaline solution in addition to a hydroxylamine developing agent, a 1-aryl-3- pyrazolidinone compound, corresponding to the formula:
- R stands for an aryl group
- each of R and R stands for hydrogen, alkyl, aralkyl or aryl, and
- R stands for hydrogen, alkyl, alkoxy, aralkoxy or aryloxy.
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5256769 | 1969-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3740221A true US3740221A (en) | 1973-06-19 |
Family
ID=10464417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00078919A Expired - Lifetime US3740221A (en) | 1969-10-27 | 1970-10-07 | Development of photographic material |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3740221A (enrdf_load_stackoverflow) |
| JP (1) | JPS4913580B1 (enrdf_load_stackoverflow) |
| BE (1) | BE757904A (enrdf_load_stackoverflow) |
| CA (1) | CA985945A (enrdf_load_stackoverflow) |
| FR (1) | FR2065920A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1327035A (enrdf_load_stackoverflow) |
| NL (1) | NL7015734A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4040832A (en) * | 1975-07-02 | 1977-08-09 | Polaroid Corporation | Pyrazolidone type developing agents |
| US4209580A (en) * | 1978-10-02 | 1980-06-24 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| US4266002A (en) * | 1978-10-02 | 1981-05-05 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| US4298673A (en) * | 1972-03-10 | 1981-11-03 | Fuji Photo Film Co., Ltd. | Lithographic type diffusion transfer developing composition |
| US4367279A (en) * | 1974-09-06 | 1983-01-04 | Eastman Kodak Company | Silver halide complexing agents of sulfones, nitriles, and onium salts |
| US5300514A (en) * | 1990-07-17 | 1994-04-05 | Eli Lilly And Company | Pyrazolidinone CCK and gastrin antagonists and pharmaceutical formulations thereof |
| US5618652A (en) * | 1995-03-22 | 1997-04-08 | Fuji Photo Film Co., Ltd. | Image formation method by silver salt diffusion transfer |
-
0
- BE BE757904D patent/BE757904A/xx unknown
-
1969
- 1969-10-27 GB GB5256769A patent/GB1327035A/en not_active Expired
-
1970
- 1970-09-14 JP JP45080858A patent/JPS4913580B1/ja active Pending
- 1970-10-02 FR FR7035810A patent/FR2065920A5/fr not_active Expired
- 1970-10-05 CA CA094,826A patent/CA985945A/en not_active Expired
- 1970-10-07 US US00078919A patent/US3740221A/en not_active Expired - Lifetime
- 1970-10-27 NL NL7015734A patent/NL7015734A/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298673A (en) * | 1972-03-10 | 1981-11-03 | Fuji Photo Film Co., Ltd. | Lithographic type diffusion transfer developing composition |
| US4367279A (en) * | 1974-09-06 | 1983-01-04 | Eastman Kodak Company | Silver halide complexing agents of sulfones, nitriles, and onium salts |
| US4040832A (en) * | 1975-07-02 | 1977-08-09 | Polaroid Corporation | Pyrazolidone type developing agents |
| US4209580A (en) * | 1978-10-02 | 1980-06-24 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| US4266002A (en) * | 1978-10-02 | 1981-05-05 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| US5300514A (en) * | 1990-07-17 | 1994-04-05 | Eli Lilly And Company | Pyrazolidinone CCK and gastrin antagonists and pharmaceutical formulations thereof |
| US5643926A (en) * | 1990-07-17 | 1997-07-01 | Eli Lilly And Company | Pyrazolidinone CCK and gastrin antagonists and pharmaceutical formulations thereof |
| US5618652A (en) * | 1995-03-22 | 1997-04-08 | Fuji Photo Film Co., Ltd. | Image formation method by silver salt diffusion transfer |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2065920A5 (enrdf_load_stackoverflow) | 1971-08-06 |
| JPS4913580B1 (enrdf_load_stackoverflow) | 1974-04-01 |
| NL7015734A (enrdf_load_stackoverflow) | 1971-03-25 |
| CA985945A (en) | 1976-03-23 |
| GB1327035A (en) | 1973-08-15 |
| BE757904A (enrdf_load_stackoverflow) | 1971-04-23 |
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