Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
  • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
  • C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • 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

Definitions

• ABSTRACT wherein: R is a cyano group or a rr-deficient heterocycle, and R is an aryl group, a substituted aryl group, a heterocycle or a substituted heterocycle.
• the nitrile compounds have a favourable effect on the sensitometric properties of the silver halide emulsion that are developed at elevated temperature. They reduce the supplemental fog produced by development at elevated temperature.
• the present invention relates tothe development at increased temperature of exposed photographic radiation sensitive silver halide elements.
• antifoggants or stabilizers e.g. heterocyclic mercapto compounds such as l-phenyl-5-mercapto-tetrazole and azaindenes, more particularly tetraor pentaazaindenes, especially those substituted by hydroxy or amino groups eg 5 -methyl-7-hydroxy-s-triazolo-[ 1,5- a]pyrimidine.
• the latter compounds are used to stabilize the emulsion against formation and growth of fog when the photographic materials are stored before use.
• the compounds have only a relatively weak effect in reducing fog formation when the photographic materials are used immediately after preparation.
• l-Phenyl-5- mercaptotetrazole on the contrary, has a high fogreducing effect immediately after the preparation of the photographic emulsions. Therefore, both compounds are generally used together in the emulsion.
• nitrile compounds selected from the group consisting of (a) benzene compounds carrying at least two cyano groups onthe benzene nucleus (b) vr-deficient heterocycles e.g. pyridine, quinoline, isoquinoline, etc. carrying at least one cyano group on the heterocyclic nucleus and (c) compounds carrying at least one cyano group on an olefinic group and corresponding to the formula:
• the present invention provides a method of producing photographic images, which comprises developing an exposed photographic element comprising a support and at least one photographic silver halide emulsion, at a temperature above 30 C wherein the said development is carried out in the presence of at least one nitrile compound as defined above.
• nitrile compounds of use according to the invention are particularly useful in photographic silver halide materials, which are stabilized against formation and growthof fog by means of azaindene compounds as described above and therefore the present invention also provides light-sensitive silver halide materials, which comprise an azaindene stabilizer, especially 5 methyl- 7hydroxy-s-triazolo-[l,5-a]pyrimidine, and a nitrile compound as defined above.
• Chem. 1 Com mun. 85, NC 353 (1970).
• nitrile compounds used in accordance with the present invention may be present in any of the water-permeable colloid layers of the photographic material, which are in water-permeable relationship with the silver halide emulsion layer e.g. a gelatin antistress layer, an intermediate layer, a filter layer, etc.
• the silver halide emulsion layer e.g. a gelatin antistress layer, an intermediate layer, a filter layer, etc.
• the preparation of the silver halide emulsions involves three separate operations:
• the compounds of use according to the present invention can be added to the emulsion during no matter what step of emulsion preparation, preferably just before the coating of the emulsion on a suitable support, e.g. paper, glass, or film such as cellulose triacetate and polyethylene terephthalate.
• a suitable support e.g. paper, glass, or film such as cellulose triacetate and polyethylene terephthalate.
• the compounds of use according to the invention can be used with any type of light-sensitive material that after exposure is intended to be processed at elevated temperature.
• Various silver salts can be used as light-sensitive salt, e.g. silver bromide, silver iodide, silver chloride or mixed silver halides, e.g. silver chlorobromide or silver bromoiodide. They are particularly yaluable to improve the fog on rapid processing at elevated temperature of medium or high-speed image forming silver halide emulsions, in which the silver halide is predominantly silver bromide, e.g. silver bromoiodide emulsions, the iodide content of which is generally less than mole percent.
• the silver halides are dispersed in the common hydrophilic colloids such as gelatin, casein, zein, polyvinylalcohol, carboxymethyl cellulose, alginic acid etc. gelatin being, however, favoured.
• the common hydrophilic colloids such as gelatin, casein, zein, polyvinylalcohol, carboxymethyl cellulose, alginic acid etc. gelatin being, however, favoured.
• the silver halide emulsions for being processed after exposure at elevated temperature generally are silver halide emulsions having a low content of hydrophilic colloid e.g. gelatin.
• the ratio of hydrophilic colloid, more particularly gelatin, to silver halide expressed as silver nitrate is generally comprised between 0.2 and 0.6.
• the compounds of use according to the invention may be used in amounts varying between very wide limits. The optimum amount for each individual compound can be easily determined by some simple test known to those skilled in the art. In the silver halide emulsion they are generally employed in amounts comprised between 1 mg and 1,000 mg per mole of silver halide.
• the silver halide emulsions can be sensitized chemically as well as spectrally.
• the emulsions can be digested with naturally active gelatin or sulphur compounds, e.g. allyl thiocyanate, allyl thiourea, sodium thiosulphate etc.
• the emulsions can be sensitized also by means of reductors, e.g. tin compounds as described in UK. Pat. Specification 789,823 and by means of small amounts of noble metal compounds, e.g. of gold, platinum, palladium, iridium, ruthenium, and rhodium as described by R. Koslowsky, Z. Wiss. Phot. 46, 67-72 (.1951).
• noble metal compounds are ammonium chloropalladate, potassium chloroplatinate, potassium chloroaurate, and potassium aurithiocyanate.
• the emulsions can also be sensitized chemically with a combination of the above chemical sensitizers.
• the emulsions may further comprise compounds that sensitize the emulsion by development acceleration, e.g. alkylene oxide polymers.
• alkylene oxide polymers may be of various type, e.g. polyethylene glycol having a molecular weight of 1,500 or more, alkylene-oxide condensation products or polymers as described in US. Pat. Nos. 1,970,578 2,240,472 2,423,549 2,441,389 2,531,832 and 2,533,990 and in U.1(. Pat. Specifications 920,637 940,051 945,340 991,608 and 1,015,023.
• These development accelerating compounds may also be present in the silver halide developing solution.
• emulsions can be sensitized spectrally, e.g. by means of the common methine dyes such as neutrocyanines, basic or acid carbocyanines, rhodacyanines, 60 mpound.
• common methine dyes such as neutrocyanines, basic or acid carbocyanines, rhodacyanines, 60 mpound.
• hemicyanines styryl dyes, oxonol dyes and the like.
• Such spectrally sensitizing dyes have been described by F. M. l-lamer in The cyanine dyes and related compounds (1954).
• w 7 M The common emulsion stabilizers or antifoggants can be added to the silver halide emulsions or the developing bath.
• Known antifoggants or stabilizers are, e. g. sulphinic and selenic acid or salts thereof, aliphatic, aromatic or heterocyclic mercapto compounds or disulphides, e.g.
• benzothiazoline-2-thione and l-phenyl-S- mercaptotetrazole which may comprise sulpho groups or carboxyl groups, nitroindazole, nitrobenztriazole, nitrobenzimidazole, mercury compounds, e.g. those described in Belgian Pat. Nos. 524,121 677,337 707,386 and 709,195 and as already noted above azaindenes, particularly the tetraor pentaazaindenes and especially those substituted by hydroxyor amino groups as described by Birr in Z. Wiss. Phot. 47, 2-58 (1952).
• addenda e.g. hardening agents such as formaldehyde, mucochloric and mucobromic acid, dialdehydes, etc. wetting agents, e.g. the fluorinated surfactants of U.K. Pat. Application No. 58431/68, plasticizers, matting agents e.g. polymethyl methacrylate and silica particles, colour couplers, mask-forming compounds, light-screening dyes etc. may be present in the silver halide emulsion or another layer of the lightsensitive materials of the invention.
• hardening agents such as formaldehyde, mucochloric and mucobromic acid, dialdehydes, etc.
• wetting agents e.g. the fluorinated surfactants of U.K. Pat. Application No. 58431/68
• plasticizers e.g. polymethyl methacrylate and silica particles
• colour couplers e.g. polymethyl methacrylate and silica particles
• Example 1- A silver bromoiodide X-ray emulsion ready for coating comprises per kg an amount of silver halide corresponding to 190 g of silver nitrate, 74 g of gelatin, 545 mg of 5 methyl-7-hydroxy-s-triazolo[ l ,5-a]pyrimidine, 6.5 mg of 1-phenyl-Smercaptotetrazole, and 0.45 mg of mercury cyanide.
• the emulsion portions were coated on a polyethylene terephthalate support and dried.
• Method of producing photographic images whichcomprises developing an exposed photographic element comprising a support and at least one photographic silver halide emulsion, at a temperature above C, wherein the said development is carried out in the presence of at least one nitrile compound selected from the group consisting of:
• R is an aryl group or a heterocycle.
• a light-sensitive photographic silver halide material which comprises besides an azaindene emulsion stabilizer at least one nitrile compound selected from 30 the group consisting of:
• R is a cyano group or a 'rr-deficient heterocycle
• R is an aryl group or a heterocycle.
• a light-sensitive photographic material wherein the ratio of gelatin to silver halide expressed as silver nitrate in the emulsion is comprised between 0.2 and 0.6.
• I 9 A light-sensitive material according to claim 6, .wherein the azaindene emulsion stabilizer is 5-methyl-' '-7-hydroxy-s-trizolo[ l ,S-a] pyrimidine.

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• 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)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Plural Heterocyclic Compounds (AREA)

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Citations (5)

• 0
  • BE BE788688D patent/BE788688A/nl unknown
• 1971
  • 1971-09-17 GB GB4351871A patent/GB1395161A/en not_active Expired
• 1972
  • 1972-09-13 FR FR7232681A patent/FR2152995B3/fr not_active Expired
  • 1972-09-14 US US00289093A patent/US3841878A/en not_active Expired - Lifetime
  • 1972-09-15 DE DE2245287A patent/DE2245287A1/de active Pending

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