EP0150517B1 - Eléments photographiques et liquides contenant un biocide pour le traitement de ces éléments - Google Patents

Eléments photographiques et liquides contenant un biocide pour le traitement de ces éléments Download PDF

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Publication number
EP0150517B1
EP0150517B1 EP19840200099 EP84200099A EP0150517B1 EP 0150517 B1 EP0150517 B1 EP 0150517B1 EP 19840200099 EP19840200099 EP 19840200099 EP 84200099 A EP84200099 A EP 84200099A EP 0150517 B1 EP0150517 B1 EP 0150517B1
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EP
European Patent Office
Prior art keywords
biocide
photographic
silver halide
dioxan
elements
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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
Application number
EP19840200099
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German (de)
English (en)
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EP0150517A1 (fr
Inventor
Godfried Antoon Kockelbergh
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
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Agfa Gevaert NV
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Publication date
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Priority to DE8484200099T priority Critical patent/DE3468281D1/de
Priority to EP19840200099 priority patent/EP0150517B1/fr
Priority to JP1337485A priority patent/JPS60186836A/ja
Publication of EP0150517A1 publication Critical patent/EP0150517A1/fr
Application granted granted Critical
Publication of EP0150517B1 publication Critical patent/EP0150517B1/fr
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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
    • 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
    • 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

Definitions

  • the present invention relates to photographic elements and liquids for the manufacture or processing of such elements containing a biocide.
  • a hydrophilic colloid e.g. containing gelatin being an ideal nutrient for bacteria and fungi
  • a biocide usually phenol to kill these micro-organisms.
  • the phenols used are phenol itself, thymol and p-chloro-m-cresol.
  • Phenols have a particularly unpleasant smell, are toxic for mammals, irritate the skin and have therefore to be manipulated with care. Moreover, they have a too small solubility in acidic aqueous media so that they may be incompatible with acidified photographic compositions e.g. particular silver halide gelatin coating compositions and acidic processing solutions from which the biocide could be applied by imbibition into the photographic element.
  • acidified photographic compositions e.g. particular silver halide gelatin coating compositions and acidic processing solutions from which the biocide could be applied by imbibition into the photographic element.
  • Phenols as biocide in photographic compositions cannot be replaced by any biocide suitable for industrial use since many of the known biocides affect the sensitometric properties of the photographic elements prepared or treated with compositions containing them.
  • nitro-alcohols have been described as useful compounds for inhibiting biological growth in acidic photographic processing compositions.
  • a photographic element containing a hydrophilic colloid and a biocide is provided, characterized in that said biocide is 5-bromo-5-nitro-1,3-dioxan having the following structural formula:
  • Said dioxan is active against gram-positive and gram-negative bacteria as well as fungi in concentrations otO.02 to 0.05% by weight in aqueous solutions and solid hydrophilic colloid compositions. Toxicological and dermatological investigations have demonstrated that said dioxan is tolerated by mammals without adverse reactions.
  • the 5-bromo-5-nitro-1,3-dioxan is soluble in neutral, alkaline as well as acidic aqueous media and is compatible (without affecting transparency) with layers containing a proteinaceous colloid binder such as gelatin.
  • Photographic materials containing according to the present invention a dioxan-biocide in a hydrophilic colloid medium are, e.g. photographic elements containing (a) silver halide hydrophilic colloid emulsion layer(s) and elements that are not photosensitive but contain a hydrophilic colloid layer and are suited for use as image-receiving element in conjunction with a photographic silver halide element in a diffusion transfer reversal (DTR-) processing.
  • DTR- diffusion transfer reversal
  • the optimum amount of the said dioxan biocide in elements for photographic image formation, coating compositions and processing liquids is readily determined by comparing the growth of bacteria and fungi with control liquids (solutions, emulsions or suspensions) and solid hydrophilic colloid media containing no biocide and those containing increasing concentrations thereof.
  • Photographic elements e.g. silver halide emulsion layer materials, containing in one or more hydrophilic colloid layers a coverage of 2 milligram to 30 milligram per m 2 of the 5-bromo-5-nitro-1,3-dioxan are adequately protected against microbiological growth.
  • 5-bromo-5-nitro-1,3-dioxan The bactericidal activity of 5-bromo-5-nitro-1,3-dioxan has been found to be at least 20 times as strong as that of phenol. The fungicidal activity compared with that of phenol is still higher. From comparative tests could further be concluded that 5-bromo-5-nitro-1,3-dioxan is a stronger bactericide than the nitro-propanols described in the already mentioned GB-A-1,177,048, which nitro-propanols are only stable in acidic medium.
  • the said dioxan-biocide can be incorporated into the coating composition of a silver halide emulsion layer or other colloid layers in water-permeable relationship therewith according to any technique known by those skilled in the art for incorporating photographic ingredients, such as colour couplers, into colloid compositions.
  • the dioxan-biocide can be incorporated in solutions or dispersions of photographic ingredients that include e.g. aqueous dispersions of polymers (latices) applied in the production of photographic elements. Since these dispersions or solutions are normally stored for days or weeks before being incorporated in the coating composition of a layer of a photographic element the dioxan-biocide also exerts its favourable bactericide activity on these solutions or dispersions.
  • aqueous dispersions of polymers latices
  • a liquid coating composition used in the manufacture of the present photographic material contains, e.g., said dioxan-biocide in a concentration in the range of 50 milligram to 500 milligram per litre.
  • hydrophilic colloid(s) serving as binding agent(s) are used in admixture with a synthetic polymer applied from a latex as described e.g. in EP-A-0010335 and GB-P 1,453,057, and such mixture contains the said dioxan-biocide already before use in the preparation of an element for photographic image formation according to the present invention.
  • the said dioxan-biocide can be used in conjunction with any kind of photographic silver halide emulsion where the silver salts can be, e.g., silver bromide, silver iodide, silver chloride or mixed silver halides such as silver chlorobromide, silver bromoiodide, and silver chlorobromoiodide.
  • the latent images may be formed predominantly at the surface of the silver halide crystals of formed predominantly inside the silver halide crystals.
  • the hydrophilic colloid used as the vehicle for the silver halide can be, e.g., gelatin, colloidal albumin, zein, casein, a cellulose derivative, e.g. carboxymethylcellulose, a synthetic hydrophilic colloid such as polyvinyl alcohol or poly-N-vinylpyrrolidone. If desired, compatible mixtures of two or more of these colloids can be employed for dispersing the silver halide.
  • Light-sensitive silver halide emulsions used in the preparation of a photographic element according to the present invention can be sensitized chemically as well as optically. They can be sensitized chemically by carrying out the ripening in the presence of small amounts of sulphur-containing compounds such as allylthiocyanate, allyl thiourea, or sodium thiosulphate.
  • sulphur-containing compounds such as allylthiocyanate, allyl thiourea, or sodium thiosulphate.
  • the emulsions can also be sensitized by means of reducing agents, e.g., tin compounds as described in FR-A-1,146,955 and in BE-A-568,687, imino- aminomethane salphinic acid compounds as described in GB-A-789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium, and rhodium compounds. They can be sensitized optically by means of cyanine and merocyanine dyes.
  • reducing agents e.g., tin compounds as described in FR-A-1,146,955 and in BE-A-568,687, imino- aminomethane salphinic acid compounds as described in GB-A-789,823
  • noble metal compounds such as gold, platinum, palladium, iridium, ruthenium, and rhodium compounds. They can be sensitized optically by means of cyanine and merocyanine dye
  • the said silver halide emulsions can also comprise compounds that sensitize the emulsions by development acceleration e.g. compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described i.a. in US­A­2,531,832­ 2,533,990, in GB-A-920,637 - 940,051 - 945,340 - 991,608 and 1,091,705; onium derivatives of amino-N-oxides as described in GB-A-1,121,696, and thioether compounds as described, e.g., in GB-A-1,455,413 and 1,528,951.
  • development acceleration e.g. compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described i.a. in US­A­2,531,832­ 2,533,990, in GB-A-920,637 - 940,051 - 945,340 - 991,608 and 1,091,705; onium derivative
  • the silver halide emulsions may be of the black-and-white or colour type, so that they may contain any type of colour coupler, dye or dye precursor, e.g. as is used in common silver halide colour photography or dye diffusion transfer photography.
  • the dioxan-biocide can be used in black-and-white and colour materials for the positive-negative photography or the reversal photography.
  • the emulsions may comprise stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-2-thione and 1-phenyl-2-tetrazoline-5-thione and compounds of the hydroxytriazolpyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in BE-A-524,121 and 677,337, and in GB-A-1,173,609.
  • stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-2-thione and 1-phenyl-2-tetrazoline-5-thione and compounds of the hydroxytriazolpyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in BE-A-524,121 and 677,337, and in GB-A-1,173,609.
  • the light-sensitive silver halide emulsions or hydrophilic colloid layers containing said dioxan-biocide may also comprise any other kind of ingredient such as those described therefor in Research Disclosure no. 17,643 of December 1978.
  • the silver halide emulsions containing said dioxan-biocide can be coated onto a wide variety of supports.
  • Typical supports are e.g. cellulose ester film, polyvinylacetal film, polystyrene film, polyethylene terephthalate film and related films or resinous materials as well as glass, paper, or paper boards, such as paper or paper board coated with plastics, e.g. polyethylene-coated paper.
  • the 5-bromo-5-nitro-1,3-dioxan is used in a silver halide developing solution, silver halide complexing solution or a silver metal bleaching solution.
  • the dioxan-biocide When incorporated in a treating solution for a photographic silver halide material the dioxan-biocide is used e.g. in a concentration of 50 milligram to 500 milligram per litre.
  • Such treating solution is, e.g., a silver halide developing solution, silver halide complexing solution or silver metal bleaching solution.
  • test solutions One group of the test solutions was infected in a same concentration by bacteria isolated from a spoiled gelatin solution and another group of test solutions was infected by fungi likewise isolated from a spoiled gelatin solution.
  • the infected test solutions were kept at 37°C to promote biological growth and samples of 1 ml were taken thereof after 24 h and 3 weeks.
  • the 1 ml samples were used to infect commercial nutrients for bacteria and fungi respectively which were incubated under the same circumstances for the development of colonies of micro-organisms.

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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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paints Or Removers (AREA)

Claims (5)

1. Elément photographique contenant un colloîde hydrophile et un biocide, caractérisé en ce que ce biocide est le 5-bromo-5-nitrol-1,3-dioxanne répondant à la formule structurale suivante:
Figure imgb0007
2. Elément photographique selon la revendication 1, caractérisé en ce qu'il contient une ou plusieurs couches d'émulsions aux halogénures d'argent.
3. Elément photographique selon la revendication 1 ou 2, caractérisé en ce qu'il contient ce biocide à raison de 2 mg à 30 mg/m2.
4. Liquide pour le traitement d'un élément photographique, ce liquide étant une solution dévelop- patrice pour les halogénures d'argent, une solution complexant les halogénures d'argent ou une solution de blanchiment de l'argent métallique contenant un biocide, caractérisé en ce que le biocide répond à la formule suivante:
Figure imgb0008
5. Liquide pour le traitement d'un élément photographique selon la revendication 4, caractérisé en ce qu'il contient ce biocide en une concentration se situant dans l'intervalle allant de 50 mg à 500 mg/litre.
EP19840200099 1984-01-26 1984-01-26 Eléments photographiques et liquides contenant un biocide pour le traitement de ces éléments Expired EP0150517B1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE8484200099T DE3468281D1 (en) 1984-01-26 1984-01-26 Photographic elements and liquide for the processing of such elements containing a biocide
EP19840200099 EP0150517B1 (fr) 1984-01-26 1984-01-26 Eléments photographiques et liquides contenant un biocide pour le traitement de ces éléments
JP1337485A JPS60186836A (ja) 1984-01-26 1985-01-25 写真素子および殺菌剤を含有するかかる素子を製造または処理するための液体

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19840200099 EP0150517B1 (fr) 1984-01-26 1984-01-26 Eléments photographiques et liquides contenant un biocide pour le traitement de ces éléments

Publications (2)

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EP0150517A1 EP0150517A1 (fr) 1985-08-07
EP0150517B1 true EP0150517B1 (fr) 1987-12-23

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JP (1) JPS60186836A (fr)
DE (1) DE3468281D1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3924110A1 (de) * 1989-07-20 1991-01-31 Agfa Gevaert Ag Fotografisches material und seine herstellung
EP0691578A3 (fr) 1994-03-22 1996-07-17 Agfa Gevaert Nv Elément formant image et méthode de la fabrication d'une plaque d'impression par le procédé de diffusion-transfert de sel d'argent
JP3400570B2 (ja) 1994-10-12 2003-04-28 富士写真フイルム株式会社 記録材料製造装置の殺菌方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542553A (en) * 1967-09-15 1970-11-24 Eastman Kodak Co Inhibiting biological growths in acidic photographic processing solutions with nitro alcohols
US3542810A (en) * 1968-09-05 1970-11-24 Eastman Kodak Co 5-acetal-2-norbornene compounds

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Publication number Publication date
EP0150517A1 (fr) 1985-08-07
JPH0530258B2 (fr) 1993-05-07
JPS60186836A (ja) 1985-09-24
DE3468281D1 (en) 1988-02-04

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