Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
  • C07C317/08—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
• • 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
  • G03C1/30—Hardeners

Definitions

• This invention relates to a hardener for the gelatin films of a light-sensitive silver halide photographic material, said hardener comprising a compound of the general formula,
• a light-sensitive silver halide photographic material is prepared by forming various layers such as silver halide photographic emulsion layer, filter layer, inter layer, protective layer, sub layer, backing layer, etc. on a suitable support such as glass, paper or synthetic resin film.
• These layers are composed mainly of gelatin, so that the physical properties of said layers are dependent chiefly upon the physical properties of gelatin.
• gelatin itself is low in melting point, water-swelling and low in mechanical strength, and these properties are not desirable, or rather to say, are fatal drawbacks for the layers constituting a light-sensitive silver halide photographic material.
• Phenyl 3-phenyl-2-propynyl sulfone The above-mentioned compounds may be synthesized by oxidizing corresponding acetylene sulfides according to, for example, the method disclosed in Bull. Soc. Chim. Fr., 1966, 3024. Procedures for synthesis of the compounds are set forth below as reference examples.
• the hardener prol propynyl sulfone in the form of prisms, yield 88.2%, vides effective stability without giving any detrimental m.p. 909 1 C. effect to the photographic emulsion, and exhibits excel-
• the compound having the aforesaid general formula lent hardening effect even when the photographic may be incorporated as a gelatin film hardener into any terial is subjected to high temperature development of gelatin-containing layers constituting a lightand automatic treatment.
• the present invention is illustrated in further detail emulsion layer, inter layer, protective layer and backbelow with reference to examples, but it is needless to lug layer, whereby the film can be hardened.
• a photographic film bearing the abovevarious modifications are possible within the scope of mentioned layers may be hardened by immersing the the in ention. film in a solution of the said compound, or by dipping the film in any of the baths containing the said com- EXAMPLE 1 pound at the time of development treatment.
• the hardener of the Present invention y be used in combina- A silver iodobromide emulsion for photographic negtion with a known inorganic hardener such as chroative,which emulsion contains 3 mole% of silver iodide mium alum or chromium trichloride, or a known orwas charged with a gold sensitizer and then subjected ganic hardener such as formalin, glyoxal, acrolein or to second ripening. Subsequently, the emulsion was dithe like.
• a known inorganic hardener such as chroative,which emulsion contains 3 mole% of silver iodide mium alum or chromium trichloride, or a known orwas charged with a gold sensitizer and then subjected ganic hardener such as formalin, glyoxal, acrolein or to second ripening. Subsequently
• the hardremaining 3 portions were individually incorporated ener of the present invention is used ordinarily in the with each of methanol solutions of the previously exform of a solution in water or methanol, but may also emplified compounds (2), (7) and (10) and then be used in the form of a solution in one or more of or coated on a support to prepare samples of the present ganic solvents such as dimethylformamide and the like. invention.
• the amount of the hardener to be incorporated is pref- These samples were individually stored at 55C.
• the hardstored samples and the fresh samples (which were imener is desired to be incorporated into a light-sensitive mediately after coating on supports) were individually silver halide emulsion layer, it is preferable to incorpoimmersed in pure water, and the temperature at which rate the hardener after the second ripening of said sileach sample was dissolved on the film surface was meaver halide emulsion. in this case, the hardener of the sured.
• the stored samples were impresent invention may be used in combination with mersed in a 3% solution of sodium carbonate monohyother ordinary additives for said photographic emuldrate at 50C., and the time required for each sample sion such as, for example, stabilizers, coating aids, sento initiate the dissolution of its film surface was measitizers or sensitizing dyes. Further, the photographic sured. Further, the samples were subjected to sensitomemulsion used may have been subjected to chemical etry to measure the values of relative speed and fog of sensitization by use of gold or sulfur, and may have the photographic emulsions. The results obtained were been incorporated with an coupler. as set forth in Table 1.
• the samples according to the present invention had no desensitizing action, successfully inhibited the fog and displayed excellent hardening effects.
• EXAMPLE 2 The same photographic emulsion as in Example 1 was subjected to second ripening and then charged with a color coupler l-(4.'-phenoxy-3-sulfophenyl)-3- heptadecyl-S-pyrazolone. Thereafter, the emulsion was divided into 4 portions, and one portion was coated as it was on a support to prepare a control sample, while the remaining 3 portions were individually incorporated with each of aqueous solutions of the previously exemplified compounds (3), (6) and (11) and then coated on supports to prepare samples of the present invention.
• EXAMPLE 3 A high speed light-sensitive silver iodobromide emulsion for roentgenography, which contained 3 mol of silver iodide was subjected to ordinary chemical ripening, and then charged with 100 ml. per liter of the emulsion of 5-methyl-7-hydroxy-s-triazolo(2.5- a)pyrimidine as a stabilizer and 2 g per liter of the emulsion of saponin as a coating aid. Subsequently, the emulsion was divided into seven portions, and one portion was coated as it was on a cellulose triacetate support to prepare a control sample, while the remaining six portions were individually coated to prepare samples of the present invention.
• the films were measured in surface strength in the following manner: Each sample was dipped for 2 minutes in a 3% sodium carbonate (mono- TABLE 2 Hardening characteristics Sensitivity Pure water bath C.) Alkali bath (sec.) characteristics of emulsion After After Amount of (immediately After storage After storage hardener after preparation) Immedistorage at C Immedistorage at 50 C per 10 g. ately at (1. and RH ately at 55 C. and RH of gelatin Relative after for 3 for after for 3 80% for Sample (mg.) Fog speed coating days 3 days coating days 3 days Control sample 0. 06 32 38 42 2. 0 2. 5 3. 2 Sample incorporated with exemplified compound 250 0. 04 56 95 Sample incorporated with exemplified compound (6) 250 0.03 98 63 122 280 Sample incorporated with exemplified compound (11) 5 0- 04 96 68 92 Above 65. b Above 300.
• the samples according to the present invention displayed excellent hardening effects without injuring the photographic properties. Moreover, not only the couplers used were not injured in color development but also no dye stains were observed.
• the film surface strength is expressed in terms of a load (g) with which the film surface had begun to be scratched with the pin.

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)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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Publications (1)

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Cited By (6)

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Citations (3)

• 1970
  • 1970-06-20 JP JP45053612A patent/JPS4913326B1/ja active Pending
• 1971
  • 1971-06-15 CA CA115,743A patent/CA962505A/en not_active Expired
  • 1971-06-17 GB GB2848771A patent/GB1307203A/en not_active Expired
  • 1971-06-19 DE DE19712130483 patent/DE2130483A1/de active Pending
  • 1971-06-21 US US00155237A patent/US3772023A/en not_active Expired - Lifetime

Patent Citations (3)

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