US3311474A - Photographic material - Google Patents

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Publication number
US3311474A
US3311474A US303124A US30312463A US3311474A US 3311474 A US3311474 A US 3311474A US 303124 A US303124 A US 303124A US 30312463 A US30312463 A US 30312463A US 3311474 A US3311474 A US 3311474A
Authority
US
United States
Prior art keywords
compound
group
silver halide
light
sensitive
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
Application number
US303124A
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English (en)
Inventor
Willems Jozef Frans
Sevens Gerard Michiel
Sels Francis Jeanne
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.)
Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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.)
Filing date
Publication date
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Application granted granted Critical
Publication of US3311474A publication Critical patent/US3311474A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium

Definitions

  • Fog depends on the development circumstances as well as on the state of the light-sensitive emulsion. Indeed, the fog increases according to the degree of development, and in constant development circumstances according to the storing time of the light-sensitive emulsion, the temperature and the relative humidity of the atmosphere wherein the emulsion is stored. For it is generally known to carry out accelerated tests on the stability of the lightsensitive emulsion by bringing it for a certain time in an atmosphere of increased temperature and/ or relative humidity. It is evident that a light-sensitive emulsion should be obtained which is as stable as possible at high temperature and high relative humidity for instance in view of its use in tropical countries.
  • Fog arises also When some chemical substances such as hydrogen sulfide, hydrogen peroxide and strong reductors act upon the lightsensitive silver halide emulsion layer. Fog occurs generally all over the surface of the light-sensitive emulsion layer but when the emulsion is very strongly fogged the fog is mostly not uniformly spread.
  • Antifogging agents and stabilizers are substances which act upon the light-sensitive silver halide emulsion layer in such a way that the arising of fog on development is either prevented or strongly reduced.
  • heterocyclic compounds carrying a mercapto group substituted by an alkyl carbonyl radical, an aryl carbonyl radical, an alkyl sulfonyl radical or an aryl sulfonyl radical said radicals being in their turn either or not substituted are especially good stabilizers and anti-fogging agents for a light-sensitive silver halide emulsion without causing an appreciable desensitization of the light-sensitive silver halide emulsion material.
  • Light-sensitive material comprises essentially a support and a light-sensitive silver halide emulsion layer, wherein the light-sensitive 3,31 1,474 Patented Mar. 28, 1967 emulsion layer and/or a Water-permeable layer which is in effective contact with said light-sensitive emulsion layer comprise(s) a compound of the following general formula:
  • These compounds bearing a substituted mercapto group may also be incorporated in a light-sensitive material of use in the silver salt diffusion transfer process. In that case they do not act merely as a stabilizer but also as a black-toning agent. In the last case they may also be incorporated in the image-receiving material If these compounds are to be incorporated into the light-sensitive silver halide emulsion layer this may be effected by adding them to the emulsion in whatever stage of its preparation.
  • the compounds in the silver halide emulsion layer may also the incorporated into a Water-permeable layer present at the same side of the support as the light-sensitive silver halide emulsion layer for instance into a gelatin covering layer, into an intermediate layer, etc.
  • the adding of said compounds bearing a substituted mercapto group mostly occurs from a solution of said com-pounds for instance in water, a lower aliphatic alcohol and acetone.
  • the emulsions used may be sensitized according to a known method. They may be chemically sensitized by ripening in the presence of small amounts of sulfur containing compounds such as allyl isothiocyanate, allyl thiourea, sodium thiosulfate etc.
  • the emulsions may also be sensitized by means of reductors for instance tin compounds as described in the French patent specification 1,146,955 and in the Belgian patent specification 568,687, imino-a-mino methane sulfinic acid compounds as described in the British patent specification 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium.
  • polyalkylene oxide derivatives for instance polyethylene oxide having a molecular weight comprised between 1000 and 20,000, further condensation products of alkylene oxides with aliphatic alcohols or glycols, cyclic dehydration products of hexitoles, alkyl substituted phenols, aliphatic carboxylic acids, aliphatic amines and diamines or with aliphatic atmides.
  • Said condensation products have a molecular weight of at least 700 and preferably above 1000.
  • sensitizers may of course be applied together as described in the Belgian patent specification 537,278 and the British patent specification 727,982.
  • said compounds with substituted mercapto group may be applied to optically as well as to nonoptically sensitized emulsions.
  • Example 1 To a series of the same high-sensitive gelatin silver bromo-iodide emulsions (about 3.5% of iodide) are added 0.055 millimole of stabilizers according to the present invention and other comparative stabilizers per kg. of emulsion. After the classic chemical ripening said emulsions are coated onto a support and dried. The materials thus obtained are cut into two strips A and B. The strips A are immediately exposed for 4 seconds and developed for 4 minutes in the developing bath of the comp ositioin given below whereas the strips B first are stored for 5 days at high temperature and high relative humidity before being treated likewise.
  • the developing bath has the following composition:
  • the compounds according to the present invention may be applied in all kinds of emulsions such as silver bromo-iodide emulsions, silver bromide emulsions, silver bromo-chloride emulsions, silver chloride emulsions and silver chloro-iodide emulsions thus in all usable negative and positive photographic film and paper kinds.
  • emulsions such as silver bromo-iodide emulsions, silver bromide emulsions, silver bromo-chloride emulsions, silver chloride emulsions and silver chloro-iodide emulsions thus in all usable negative and positive photographic film and paper kinds.
  • the amount of compounds with substituted mercapto group may vary according to the use thereof as stabilizer and/or as black-toning agent, the kind of silver halide or mixture of silver halides applied, the ripening state, the occasional presence of other emulsion additives such as color couplers, optical bleaching agents, anti-oxidation agents, black-toning agent etc.
  • the amount of stabilizer generally varies from 0.01 to to 3 g. per mole of silver halide. In special circumstances, however, for instance for obtaining defined effects, larger amounts may be applied.
  • the compounds bearing a substituted mercapto group act as black-toning agent in a diffusion transfer process and further have a specially strong anti-fogging and stabilizing action on a light-sensitive silver halide emulsion layer without, however, having an appreciable desensitizing action.
  • the light-sensitive material thus obtained is image-wise exposed and then passed together with an image-receiving material through an ordinary treating bath for producing diffusion transfer images. After a contact period of 20 seconds both materials are separated and a neutr black positive image of the original is obtained.
  • the light-sensitive material thus prepared shows, immediately after adding said compound a decrease in sensitivity and gradation contrary to the material comprising the compound with substituted mercapto group.
  • Photographic material comprising at least one lightsensitive silver halide emulsion layer wherein said matewherein:
  • Z represents the atoms necessary to complete a heterocyclic ring
  • A represents a member selected from the group consisting of a -COR group and a SO R group wherein R represents a member selected from the group consisting of an alkyl radical, and an aryl radical.
  • Photographic material according to claim 1 wherein said compound is incorporated in the light-sensitive emulsion layer.
  • Image-receiving material for use in a silver complex diffusion transfer process comprising in at least one water-permeable layer a compound of the following formula:
  • C-S-A 8 group consisting of an alkyl radical, and an aryl radical.
  • a photographic silver complex diffusion transfer process according to which a positive image of an original is obtained by development of an image-wise exposed light-sensitive silver halide emulsion layer and diffusion of the non-developed complexed silver halide from the emulsion layer to an image-receiving material Where the complexed silver halide is transformed into a silver containing image in the presence of development nuclei and at least one compound of the following formula:
  • Z represents the atoms necessary to complete a heterocyclic ring
  • A represents a member selected from the group consisting of a COR group and a -SO R group wherein R represents a member selected from the group consisting of an alkyl radical, and an aryl radical.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Plural Heterocyclic Compounds (AREA)
US303124A 1962-08-31 1963-08-19 Photographic material Expired - Lifetime US3311474A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE2041926 1962-08-31

Publications (1)

Publication Number Publication Date
US3311474A true US3311474A (en) 1967-03-28

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Application Number Title Priority Date Filing Date
US303124A Expired - Lifetime US3311474A (en) 1962-08-31 1963-08-19 Photographic material

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BE (1) BE621948A (en))
DE (1) DE1173336B (en))
GB (1) GB1053587A (en))

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420664A (en) * 1966-01-03 1969-01-07 Gaf Corp Dehydrodithizone and mercaptotetrazolium salts as silver halide photographic antifoggants and stabilizers
US4131470A (en) * 1976-12-21 1978-12-26 Veb Filmfabrik Wolfen Process for the stabilization and antifogging of photographic silver halide emulsions
US4396707A (en) * 1980-09-02 1983-08-02 Agfa-Gevaert Aktiengesellschaft Photographic material, process for the production thereof, process for the production of photographic images and new triazoles
US5081009A (en) * 1988-02-01 1992-01-14 Fuji Photo Film Co., Ltd. Process for preparing an internal latent image silver halide emulsion

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365294A (en) * 1963-04-27 1968-01-23 Agfa Ag Photographic material containing yellow fog-preventing agents
GB1470369A (en) * 1973-06-22 1977-04-14 Agfa Gevaert Photographic complex diffusion transfer process
DE3062779D1 (en) * 1979-11-16 1983-05-19 Asahi Chemical Ind Novel tetrazole-5-thiol esters and process for preparing cefamandole using same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE874702C (de) * 1945-12-15 1953-04-27 Gen Aniline & Film Corp Stabilisatoren fuer photographische Emulsionen
DE957183C (de) * 1953-07-01 1957-01-31 Eastman Kodak Co Stabilisiertes photographisches Material

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420664A (en) * 1966-01-03 1969-01-07 Gaf Corp Dehydrodithizone and mercaptotetrazolium salts as silver halide photographic antifoggants and stabilizers
US4131470A (en) * 1976-12-21 1978-12-26 Veb Filmfabrik Wolfen Process for the stabilization and antifogging of photographic silver halide emulsions
US4396707A (en) * 1980-09-02 1983-08-02 Agfa-Gevaert Aktiengesellschaft Photographic material, process for the production thereof, process for the production of photographic images and new triazoles
US5081009A (en) * 1988-02-01 1992-01-14 Fuji Photo Film Co., Ltd. Process for preparing an internal latent image silver halide emulsion

Also Published As

Publication number Publication date
BE621948A (en))
GB1053587A (en))
DE1173336B (de) 1964-07-02

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