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
  • G03C1/30—Hardeners
• • 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
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3924—Heterocyclic
  • G03C7/39272—Heterocyclic the nucleus containing nitrogen and oxygen

Definitions

• This invention relates to photographic products useful for color prints in which staining is inhibited comprising gelatin-silver halide photographic emulsions, pyrazolone coupler and an isoxazolium salt as a hardener for the gelatin.
• One object of our invention is to provide photographic products adapted to the making of color prints in which staining effects are inhibited and the sensitometric properties are not adversely affected.
• Another object of our invention is to provide photographic products containing gelatin-silver halide photographic emulsions, pyrazolone couplers and as the hardener for the gelatin an isoxazolium salt.
• photographic products featuring the combination of emulsions having silver halide as the photosensitive element, a pyrazolone coupler which is capable of forming an azomethine dye with a phenylenediamine developer and a hardener having the following general formula:
• R is an aliphatic hydrocarbon group of 1 to 4 carbon atoms either with or without a sulfonate anion thereon
• R and R are each one of the following: hydrogen, unsubstituted alkyl, unsubstituted aryl, alkyl or aryl substituted with halogen, hydroxyl or sulfonate anion, a simple heterocyclic ring such as furyl or R and R together form an alicyclic ring
• X is an anion which contributes to the water solubility of the compound such as perchlorate, paratoluene-sulfonate or the like, unless sulfonate anion is already present, attached to R, R or R", will be free of staining when that combination is present on a paper support in its use for making photographic prints.
• Our invention is useful in combination with pyrazolone couplers such as those described in U.S. iPatent 2,640,766 of Spence
• the compounds which may be employed as hardeners in color emulsions in accordance with our invention are isoxazolium hardeners as are described in more detail in Burness and Wilson application Ser. No. 248,201, filed Dec. 31, 1962, now abandoned.
• combinations containing pyrazolone coupler, silver halide emulsion and hardener, the latter being of the type described in Ser. No. 248,201 have good brightness characteristics and exhibit less stain than compositions of like nature formerly used.
• Photographic layers in accordance with our invention show reduced stain and no adverse sensitometric eifect when an isoxazolium salt is used in a proportion which produces satisfactory hardness in layers containing gelatin-silver halide and an isoxazolium material.
• gelatin is primarily employed as the vehicle for the silver halide.
• polymers auxiliary to the gelatin may be present such as ethyl acrylate-acrylic acid copolymer, butyl acrylate-acrylic acid copolymer or some other acid substituted polymeric vehicle.
• our invention relate to color emulsions in which pyrazolone coupler is present but also included are color emulsions in which the coupler is provided from solution in some water immiscible solvent so as to constitute a packet form of emulsion.
• Our invention includes any of the recognized color photographic emulsions having silver halide as the photosensitive element, pyrazolone coupler and a hardener as described and claimed in Ser. No. 248,201.
• Our invention includes combinations of silver halide emulsion, hardener of the type described and claimed in Ser. No. 248,201 and pyrazolone coupler 1) when all three of these compo nents are in a single emulsion or (2) when one or more of these components are in a layer other than that containing one or more of these components as for example a multi-layer system in which one of the components is in a layer with or without one or both of the other members of the combination.
• Example 1 This example illustrates photographic color print material using a hardener of the invention plus a pyrazolone coupler in one case and a conventional type aldehyde hardener plus a pyrazolone coupler in the other in a multilayer photographic color product.
• a hardener of the invention plus a pyrazolone coupler in one case and a conventional type aldehyde hardener plus a pyrazolone coupler in the other in a multilayer photographic color product.
• samples B and C one emulsion contains both pyrazolone coupler and a hardener in accordance with the invention. That hardener is also used in the other five layers of the structure but pyrazolone coupler is absent.
• sample A the hardener used was an aidehyde-type hardener.
• Example 2 A magenta image-forming layer of the type of incorporated coupler photographic coating described in the example of Table I of US. Patent 3,046,129 of J. L. Graham et al. was prepared by coating a high speed silver bromoiodide emulsion sensitized to the green region of the spectrum, sulfur and gold sensitized and supplied with a dispersion in tri-o-cresylphosphate of a pyrazolone coupler such as coupler No. 7 of US. Patent 2,801,171 of Fierke et al. An isoxazolium salt was used as the hardener, the type and concentrations being listed in the following table together with a control using mucochloric acid. The results obtained were as follows:
• a photographic element which comprises a support having thereon a plurality of layers in which at least one of said layers contains gelatin-silver halide photographic emulsion, at least one of said layers contains pyrazolone coupler and at least one of said layers contains a hardener having the formula in which R is an aliphatic hydrocarbon grou of 1-4 carbon atoms either with or without a sulfonate anion thereon, R and R are each one of the following: hydrogen, unsubstituted alkyl, unsubstituted aryl, alkyl or aryl substituted with halogen, hydroxyl or sulfonate anion, a simple heterocyclic ring such as furyl or R and R" together form an alicyclic ring and X is ananion which contributes to the water solubility of the compound such as perchlorate, paratoluene-sulfonate or the like, unless sulfonate anion is already present, attached to R,
• R is an aliphatichydrocarbon group of l4 carbon atoms either with or without a sulfonate anion thereon
• R and R are each one of the following: hydrogen, unsubstituted alkyl, unsubstituted aryl, alkyl or aryl substituted with halogen, hydroxyl or sulfonate anion, a simple heterocyclic ring such as furyl or R and R"'together form an alicyclic ring and
• X is an anion which contributes to the water solubility of the compound such as perchlorate, paratoluenesulfonate or the like, unless sulfonate anion is already present, attached to R, R or R".
• a multilayer photographic product in which at least one layer contains gelatin-silver halide photographic emulsion, at least one layer contains pyrazolone coupler and at least one layer contains dimethylisoxazoliurnperchlorate.
• a multilayer photographic product in which at least one layer contains gelatin-silver halide photographic emulsion, at least one layer contains pyrazolone coupler and at least one layer contains Z-ethyLS-phenylisoxazolium-3-sulfonate.
• a multilayer photographic product in which at least one layer contains gelatin-silver halide photographic emulsion, at least one layer contains pyrazolone coupler and at least one layer contains Z-rnethyl-S-p-tolylisoxazolium-3'-sulfonate.
• a gelatin-silver halide photographic emulsion which contains pyrazolone coupler and dimethylisoxazoliumperchlorate.
• a gelatin-silver halide photographic emulsion useful in color photography which contains a pyrazolone coupler capable of forming an azomet-hine dye with a phenylenediamine developer and a hardener having the formula:
• R is an aliphatic hydrocarbon group of 1-4 carbon atoms either with or without a sulfonate anion thereon
• R and R" are each one of the following: hydrogen, unsubstituted alkyl, unsubstituted aryl, alkyl or aryl substituted with halogen, hy-droxyl or sulfonate anion, a simple heretocyclic ring such as furyl or R and R" together form an alicyclic ring
• X is an anion which contributes to the water solubility of the compound such as perchlorate, paratoluenesulfonate or the like, unless 5 sulfonate anion is already present, attached to R, R or R".
• a photographic element comprising a support bearing a plurality of layers which collectively contain silver halide, pyrazolone coupler and 2,5-dimethylisoxazoliumperchlorate.
• a photographic element comprising a support bearing a plurality of layers, one of which layers contains silver halide, pyrazolone coupler and a hardener having the formula:
• R is an aliphatic hydrocarbon group of 1-4 carbon atoms either With or Without a sulfonate anion thereon
• R and R" are each one of the following: hydrogen
• unsubstituted alkyl unsubstituted aryl, alkyl or aryl substituted with halogen, hydroXyl or sulfonate anion, a simple heterocyclic ring such as furyl or R and R together form an alicyclic ring and X is an anion which contributes to the Water solubility of the compound such as perchlorate, paratoluenesulfonate or the like, unless, sulfonate anion is already present, attached to R, R or R".

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• Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Chemical & Material Sciences (AREA)
• General Physics & Mathematics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

Priority Applications (4)

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Cited By (5)

Citations (1)

• 0
  • GB GB1143609D patent/GB1143609A/en active Active
• 1965
  • 1965-10-13 US US495723A patent/US3316095A/en not_active Expired - Lifetime
• 1966
  • 1966-10-12 DE DE19661547736 patent/DE1547736A1/de active Pending

Patent Citations (1)

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