US3740221A - Development of photographic material - Google Patents

Development of photographic material Download PDF

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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
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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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US00078919A
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English (en)
Inventor
J Willems
P Schots
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert NV
Agfa Gevaert AG
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Agfa Gevaert AG
Priority date (The priority date 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 date listed.)
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Publication of US3740221A publication Critical patent/US3740221A/en
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02Photosensitive materials characterised by the image-forming section
    • G03C8/04Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
    • G03C8/06Silver 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.

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  • 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)
US00078919A 1969-10-27 1970-10-07 Development of photographic material Expired - Lifetime US3740221A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5256769 1969-10-27

Publications (1)

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US3740221A true US3740221A (en) 1973-06-19

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US00078919A Expired - Lifetime US3740221A (en) 1969-10-27 1970-10-07 Development of photographic material

Country Status (7)

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US (1) US3740221A (ja)
JP (1) JPS4913580B1 (ja)
BE (1) BE757904A (ja)
CA (1) CA985945A (ja)
FR (1) FR2065920A5 (ja)
GB (1) GB1327035A (ja)
NL (1) NL7015734A (ja)

Cited By (7)

* Cited by examiner, † Cited by third party
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

Cited By (8)

* Cited by examiner, † Cited by third party
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
JPS4913580B1 (ja) 1974-04-01
GB1327035A (en) 1973-08-15
CA985945A (en) 1976-03-23
FR2065920A5 (ja) 1971-08-06
NL7015734A (ja) 1971-03-25
BE757904A (ja) 1971-04-23

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