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
  • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
• • 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
  • G03C1/08—Sensitivity-increasing substances
  • G03C1/10—Organic substances
• • 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
  • G03C7/3003—Materials characterised by the use of combinations of photographic compounds known as such, or by a particular location in the photographic element
  • G03C7/3005—Combinations of couplers and photographic additives
  • G03C7/3008—Combinations of couplers having the coupling site in rings of cyclic compounds and photographic additives
  • G03C7/301—Combinations of couplers having the coupling site in pyrazoloazole rings and photographic additives
• • 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

Definitions

• This invention relates to photography and more particularly to a photographic recording material containing a magenta dye forming coupler.
• magenta dye forming couplers are known.
• One type examples of which are disclosed in U. S. Patents 3.725,067 and 4,443,536 and in U. K. Patents 1,247,493; 1,252,418 and 1,253,933, includes pyrazolotriazoles which can comprise various substituents, including ballast groups. While such couplers generally provide highly desired photographic results, it has been observed that some pyrazolotriazole couplers have an inhibiting effect upon silver halide development in photographic emulsions, thereby reducing speed and contrast of resulting dye images.
• hydrolyzable chalcogenazolium salts which comprise particular quaternized substituents are capable of overcoming silver halide development inhibition caused by the pyrazolotriazole couplers.
• the present invention provides a photographic recording material comprising a support having thereon a photographic silver halide emulsion layer and a pyrazolotriazole magenta coupler which inhibits silver halide development, said recording material being characterized in that it comprises a hydrolyzable chalcogenazolium salt of a middle chalcogen which salt comprises a quaternized substituent having a carbon chain interrupted by a divalent group which has the structural formula I: wherein:
• Pyrazolotriazole couplers which have been found to inhibit silver halide development include the following compounds:
• the quaternized chalcogenazolium salts which have been found to be effective in reducing silver halide development inhibition caused by particular pyrazolotriazole coupler compounds, are disclosed in U. S. Patent 4,578,348. These salts are capable of undergoing hydrolysis which opens the chalcogenazolium ring between the 2 and 3 positions thereof, that is between the ring chalcogen atom and the carbon atom which lies mediate the ring chalcogen atom and the nitrogen atom. As hydrolyzed, these salts demonstrate the ability to suppress silver halide development inhibition caused by the described couplers.
• R 4 is hydrogen
• ring opening occurs spontaneously after incorporating the chalcogenazolium salt of the above formula in a silver halide emulsion.
• a base such as an aqueous alkaline solution of an alkali or an alkaline earth metal, or ammonium hydroxide, can be employed prior to incorporation in a silver halide emulsion.
• the quaternized substituent Q can take the form represented by formula (IV): wherein:
• T is carbonyl and T' is sulfonyl.
• T and T can be either carbonyl or sulfonyl.
• T can in each occurrence be carbonyl or sulfonyl independently of other occurrences,
• m is preferably 1.
• R 4 can take the form of any other substituent that is compatible with ring opening hydrolysis of the chalcogenazolium salt in the manner indicated. In general, the simpler the form of R 4 , the more easily hydrolysis is accomplished. It is specifically recognized that R 4 can embrace substituents that do not permit spontaneous hydrolysis of quaternized chalcogenazolium salts in silver halide emulsion coatings.
• X, R 2 and R 3 can together complete any convenient chalcogenazolium nucleus or hydrolyzed chalcogenazolium nucleus, provided the chalcogen atom is a middle chalcogen atom.
• the middle chalcogen atoms are sulfur, selenium, and tellurium, being designated "middle" chalcogen atoms since they are the atoms in Group VI of the Periodic Table of Elements, except for the highest and lowest in atomic number.
• R 2 and R 3 can take any form found in known thiazolium and selenazolium ring containing nuclei.
• R 2 and R 3 can individually take the form of hydrogen or halogen atoms; hydrocarbon moieties (e.g., alkyl, aryl, alkaryl, or aralkyl) optionally linked through a divalent oxygen or sulfur atom (e.g., an alkoxy, aryloxy, alkaryloxy, aralkoxy, alkylthio, arylthio, alkarylthio, or aralkylthio group); cyano; an amino group, including primary, secondary, and tertiary amino groups; an amido group (e.g., acetamido and butyramido); a sulfonamido group (e.g., an alkyl or arylsulfonamido group); a sulfamoyl group (e.g.,
• the alkyl groups and the alkyl moeities of other groups preferably contain from 1 to about 8 carbon atoms (e.g., methyl, ethyl, propyl, butyl, amyl, hexyl, or octyl), and most preferably contain from 1 to about 4 carbon atoms and may be further substituted by other groups, such as halogen, cyano, aryl, carboxy, alkylcarbonyl, arylcarbonyl, arylcarbonyl, and aminocarbonyl.
• groups such as halogen, cyano, aryl, carboxy, alkylcarbonyl, arylcarbonyl, arylcarbonyl, and aminocarbonyl.
• the aryl groups and the aryl moieties of other groups preferably contain 6 to about 10 carbon atoms (e.g., phenyl or naphthyl) and include substituted or unsubstituted groups.
• Useful substituents include halogen, cyano, alkyl, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, and aminocarbonyl.
• R 2 and R 3 together form one or more fused carbocyclic aromatic rings -e.g., a benzo or naphtho ring, either of which can be optionally substituted.
• the salt can be a benzothiazolium salt, a benzoselenazolium salt, an ⁇ - or p-naphthothiazolium salt, or an ⁇ - or ⁇ -naphthoselenazolium salt, such as the quaternized but otherwise unsubstituted salts or the salts in which the fused carbocyclic rings are substituted.
• Fused carbocyclic ring substituents when present, can be chosen from among those identified above for R 2 and R 3 as individual substituents.
• the fused carbocyclic ring substituents when present, can be chosen from among those present in comparable nuclei in cyanine, merocyanine, and hemicyanine dyes.
• R 2 and R 3 together form a carbocyclic aromatic ring, such as a fused benzo or an a- or ⁇ -naphtho ring.
• the fused carbocyclic aromatic rings can be unsubstituted or substituted with aliphatic or aromatic groups comprised of hydrocarbon moieties optionally linked through a divalent oxygen or sulfur atom, amino groups, amido groups, sulfonamido groups, sulfamoyl groups, ureido groups, thioureido groups, hydroxy groups, COM groups, and S0 2 M groups, wherein M is chosen to complete an acid, ester, thioester, or salt.
• benzo or naphtho ring substituents are alkyl, alkoxy, alkylthio, and hydroxy substituents, where alkyl is preferably of from 1 to 8 carbon atoms, and most preferably of from 1 to 4 carbon atoms.
• Y is included in formulae (II) and (III) to provide electronically neutral compounds.
• Y can be chosen from a wide range of ions known to be compatible with silver halide emulsions.
• the chalcogenazolium salt or the hydrolyzed chalcogenazolium salt is a betaine, no charge balancing counter ion may be required, and n can be zero.
• the quaternized chalcogenazolium salt of formula (II) has a single positive charge and R 4 is an acid anion, such as a halide or p-toluenesulfonate.
• the hydrolyzed quaternized chalcogenazolium salt of formula (III) has a single negative charge and Y is a cation, such as that provided by the base employed to effect hydrolysis - e.g.. an alkali or alkaline earth metal, or the ammonium cation.
• Preferred chalcogenazolium salts useful in this invention have the structural formula (V): wherein:
• chalcogenazolium salts described above while disclosed in U. S. Patent 4,578,348 as being useful for improving speed/fog relationships in photographic recording materials, including color photographic materials, are not recognized as having any utility with respect to overcoming inhibition of silver halide development caused by particular pyrazolotriazole magenta couplers.
• the chalcogenazolium salts can be added to the silver halide emulsion at any time following precipitation of the silver halide grains to just prior to coating.
• the amount of chalcogenazolium salt which has been found to be effective to prevent silver halide development inhibition by the pyrazolotriazole coupler compound, and which is incorporated in the silver halide layer, is from about 0.01 to about 10 millimoles thereof per mole of silver.
• the preferred concentration of salt is from about 0.1 to about 2.0 millimoles thereof per mole of silver.
• This invention also relates to a process for reducing silver halide development inhibition in a photographic recording material comprising a pyrazolotriazole magenta coupler which comprises adding to a silver halide emulsion a hydrolyzable chalcogenazolium salt of a middle chalcogen which comprises a quaternized substituent having a carbon chain interrupted by a divalent group which has the structural formula: -L-T( ⁇ NH-T mR 1 wherein:
• the silver halide emulsions can include silver halide grains of any conventional shape or size.
• the emulsions can include coarse, medium or fine silver halide grains of either regular (e.g., cubic or octahedral) or irregular (e.g. multiply twinned or tabular) crystallographic form.
• High aspect ratio tabular grain emulsions are specifically contemplated, such as those disclosed by Wilgus et al U. S. Patent 4,434,226, Daubendiek et al U. S. Patent 4,414,310, Wey U. S. Patent 4,399,215, solberg et al U. S. Patent 4,433,048, Mignot U. S. Patent 4,386,156, Evans et al U. S. Patent 4,504,570, Maskasky U. S. Patent 4,400,463, Wey et al U. S. Patent 4,414,306, Maskasky U. S. Patents 4,435,501 and 4,643,966 and Daubendiek et al U. S. Patents 4,672,027 and 4,693,964.
• silver bromoiodide grains with a higher molar proportion of iodide in the core of the grain than in the periphery of the grain such as those described in GB 1,027,146; JA 54 / 48521; US 4,379,837; US 4,444,877; US 4,665,012; US 4,686,178; US 4,565,778; US 4,728,602; US 4,668,614; US 4,636,461; EP 264,954.
• the silver halide emulsions can be either monodisperse or plolydisperse as precipitated.
• the grain size distribution of the emulsions can be controlled by silver halide grain separation techniques or by blending silver halide emulsions of differing grain sizes.
• Sensitizing compounds such as compounds of copper, thallium, lead, bismuth, cadmium and Group VIII noble metals, can be present during precipitation of the silver halide emulsion, as illustrated by U. S. Patent Nos. 1.195.432: 1,951,933; 2.448.060: 2,628,167; 2,950,972; 3,448,709 and 3.737,313.
• the silver halide emulsions can be either monodispersed or polydispersed as precipitated.
• the grain size distribution of the emulsions can be controlled by silver halide grain separation techniques or by blending silver halide emulsions of differing grain sizes.
• the emulsions can include Lippmann emulsions and ammoniacal emulsions, as illustrated by Glafkides, Photographic Chemistry, Vol. 1, Fountain Press, London. 1958, pp. 365-368 and pp. 301-304; excess halide ion ripened emulsions as described by G. F. Duffin. Photographic Emulsion Chemistry, Focal Press Ltd., London, 1966, pp.
• the silver halide emulsions can be surface sensitized.
• Noble metal e.g., gold
• middle chalcogen e.g., sulfur, selenium, or tellurium
• reduction sensitizers employed individually or in combination, are specifically contemplated.
• a preferred method of sensitization is sulfur and gold.
• the silver halide emulsions can be spectrally sensitized with dyes from a variety of classes, including the polymethine dye class, which includes the cyanines, merocyanines, complex cyanines and merocyanines (i.e., tri-, tetra-, and polynuclear cyanines and merocyanines), oxonols, hemioxonols, styryls, merostyryls, and streptocyanines.
• Illustrative spectral sensitizing dyes are disclosed in Research Disclosure, Item 17643, cited above, Section IV.
• the silver halide emulsions as well as other layers of the photographic recording materials of this invention can contain as vehicles hydrophilic colloids, employed alone or in combination with other polymeric materials (e.g., lattices).
• Suitable hydrophilic materials include both naturally occurring substances such as proteins, protein derivatives, cellulose derivatives - e.g., cellulose esters, gelatin - e.g., alkali treated gelatin (cattle, bone, or hide gelatin) or acid treated gelatin (pigskin gelatin), gelatin derivatives - e.g.
• acetylated gelatin phthalated gelatin and the like, polysaccharides such as dextran, gum arabic, zein, casein, pectin, collagen derivatives, collodion, agar-agar, arrowroot, and albumin.
• the vehicles can be hardened by conventional procedures. Further details of the vehicles and hardeners are provided in Research Disclosure, Item 17643, cited above, Sections IX and X.
• Portions of the emulsion were then chemically and spectrally sensitized to the green region of the visible spectrum using sodium thiosulfate (2.5 mg / Ag mole), potassium tetrachloroaurate (1.25 mg/Ag mole), sodium thiocyanate (80 mg/Ag mole), a mixture of the green sensitizing dyes anhydro-5-chloro-9-ethyl-5'-phenyl-3'-(3-sulfobutyl)-3-(3-sulfopropyl)oxacarbocyanine hydroxide, sodium salt and anhydro-11-ethyl-1,1'- bis(3-sulfopropyl)naphth-[1,2-d]oxazolocarbocyanine hydroxide, sodium salt (0.7 millimole/Ag mole).
• the resulting photographic elements were imagewise exposed at 1/100 of a second through a 0 -4.0 density step tablet plus a Wratten No. 9 filter (Wratten is a trademark of Eastman Kodak Co., U.S.A.) to 600W, 5500 K tungsten light source. Processing was accomplished at 37.7° C in a color process of the type described in the British Journal of Photography Annual 1979, pages 204-206, at a development time of 2 minutes and 15 seconds. Results showed the coating containing chalcogenazolium salt S-1 provided improved relative speed and contrast values.
• Wratten No. 9 filter Wratten is a trademark of Eastman Kodak Co., U.S.A.

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• Engineering & Computer Science (AREA)
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• Silver Salt Photography Or Processing Solution Therefor (AREA)

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• 1989
  • 1989-09-11 EP EP19890116757 patent/EP0359169B1/de not_active Expired - Lifetime
  • 1989-09-11 DE DE1989623591 patent/DE68923591T2/de not_active Expired - Fee Related
  • 1989-09-13 JP JP23590089A patent/JPH02120738A/ja active Pending

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