Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
  • C07D487/14—Ortho-condensed systems
• • 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

• This invention relates to a light-sensitive silver halide photographic material containing in at least one of its photographic layers a hydroimidazo-s-triazine compound as stabilizer, and the object of the invention is to provide a light-sensitive silver halide photographic material which is stable in photographic properties under high temperature and high humidity conditions and is storable for a long period of time.
• emulsion layer interlayer, sub layer or protective layer.
• tetrazaindenes Preferable as such stabilizers, tetrazaindenes have been known heretofore.
• the conventional stabilizers are not always satisfactory and tend to cause deterioration of fog, sensitivity and the like photographic properties, during storage under high temperature and high humidity conditions. These drawbacks are obviously undesirable for lightsensitive materials to be used in Japan where high temperature and high humidity are brought about in summer.
• Hydroimidazo-s-triazine compounds can be synthesized by isomerization of aziridene rings with sodium iodide and triethylamine hydrochloride or rhodanate disclosed in Journal of the American Chemical Society, Vol. 83, page 2570, and Journal of Organic Chemistry, Vol. 25, page 46l, or by dehydrochlorination reaction of B-chloroethylamino groups disclosed in Journal of the American Chemical Society, Vol. 77, page 5922.
• hydroimidazo-s-triazine compounds those which are particularly useful in the present invention are represented by the following general Formulas I, ll, Ill and lV:
• SYNTHESIS EXAMPLE 5 graphic stabilizers not only for monochromatic photographic materials but also for color photographic materials.
• the amount of the hydroimidazo-s-triazine compound to be added to or incorporated into the photographic layers of a 5 light-sensitive photographic material varies depending not Y" of the q f p l 14 only on the kind of the compound but also on the kind of the A p 'l p py 'f f y f f emulsion employed, i.e.
• the emulsion is silver from cyanunc Chloride f P py sofhum f chloride, silver bromide or silver iodide, the content of the and acetone was l the same manner as synfhesls solid solution, the particle size and photographic sensitivity of Example 013mm the above-mentioned compound In the the silver halide emulsion, and the desired degree of stabilizaform of whlte sohdtion. Generally, however, the compound is added in an amount of about 0.0 1-8 g. per mole of silver halide.
• hydrolmidazo-s-trlazlnecompounds than those men- EXAMPLE 1 tloned above can also be synthesized according the the abovementioned synthesis examples.
• the present compound may control sample. Another portion was charged with an aqueous be added to a photographic emulsion in the form of a solution 2 solution of mg. per 0.035 mole of said silver halide of the in a suitable inorganic or organic solvent such as a mixed soluknown stabilizer 4-hydroxy 6methyll ,3,3a,7-tetrazaindene, tion of water and a lower alcohol, a lower alcohol, dimethyl and was coated onto a support to prepare a comparative samsulfoxide or the like.
• the present compound may be added at ple.
• the other four portions were individually charged with any time during the step for preparation of photographic methanol solutions of the compounds set forth in Table l in emulsion, and may be previously incorporated into the start- 30 such amounts as shown in the table, and were coated onto suping materials for preparation of the emulsion.
• howports to prepare samples of the present invention. it is preferable and is most effective to add the comples were subjected to ordinary sensitometry according to the pound after completion of the second aging. JlS method K-7604 to obtain the results as set forth in Table
• the photographic speed was shown in terms of a relative photographic material may have been subjected to noble value calculated by assuming as 100 the speed of the control metal sensitization, sulfur sensitization, sensitization with alsample immediately after coating.
• the hydroimidazo-s-triazine compounds of the present invention do not injure the photographic speed attained by said sensitization and inhibit the increase of fog generated thereby, with the result that the resulting photographic materials can be more effectively enhanced in light-sensitivity increase due to said sensitization, and can be prevented from lowering in photographic speed and increase in fog during storage, particularly under high temperature and high humidity conditions.
• the above-mentioned compounds in accordance with the present invention may be used, without any detrimental interactions, in combination with other photographic additives, e.g. other stabilizers, coating aids, hardeners, toners, matting agents and the like.
• other photographic additives e.g. other stabilizers, coating aids, hardeners, toners, matting agents and the like.
• the compounds of the present invention can inhibit the generation of color fog due to fog of silver halide emulsions, and hence, are effective as photo-
• Table 1 it is understood that the light-sensitive silver halide photographic materials of the present invention show markedly excellent stability in fog and speed, and have such properties that they are less in desensitization under high temperature and high humidity conditions than the known stabilizer.
• EXAMPLE 2 The same photographic emulsion as in Example 1 was subjected to second ripening and was the incorporated according to an ordinary procedure with the color former, l-(4-phenoxy-3'-sulfophenyl)-3-heptadecyl-5 pyrazolone, to prepare a color photographic emulsion.
• This emulsion was divided into three portions. One portion of the emulsion was coated, as it was, onto a support to prepare a control sample. The other two portions were individually charged with methanol solutions of 30 mg. and 40 mg. per 0.035 mole of said silver halide of the present Compound 8, and were coated onto supports to prepare samples of the present invention.
• N N l A light-sensitive silver halide photographic element com- N prising at least one photographic layer containing 0.0l-8g./ J mole of silver halide of a hydroimidazo-s-triazine compound, R- -R (IV) 20 having one of the following general Formulas I, II, III and IV wherein Rs, which may be same or different groups, represent individually H, CH;, or C H R and R which may be same or different groups, represent individually OH, OCH SCH or NH R represents H, NH OCH or OC H X represents NH(CH ),,NH,

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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)
• Plural Heterocyclic Compounds (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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Citations (2)

• 1969
  • 1969-12-02 GB GB1252995D patent/GB1252995A/en not_active Expired
  • 1969-12-03 DE DE19691960653 patent/DE1960653A1/de active Pending
  • 1969-12-04 US US882311A patent/US3663209A/en not_active Expired - Lifetime

Patent Citations (2)

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