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
  • 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
  • G03C7/32—Colour coupling substances
  • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material

Definitions

• This invention relates to color photographic elements.
• it relates to color photographic elements with a particular combination of development inhibitor releasing compound and cyan dye-forming coupler.
• Photographic couplers which release a development inhibitor in a controlled manner are described in U.S. Patents 4,248,962 and 4,409,323, inter alia. These couplers comprise a coupler moiety which has a timing group joined in its coupling position. A development inhibitor is attached to the timing group and is released from it after the bond between the timing group and the coupler is cleaved as a result of reaction between the coupler and oxidized color developing agent. Mechanisms by which such release of the development inhibitor from the timing group can occur include an intermolecular nucleophilic displacement reaction, an electron transfer reaction, and a hydrolysis reaction. Development inhibitors also can be released, as a function of development, from timing groups which are released from compounds which are not couplers such as the hydrazides of U.S. Patent 4,684,604 and the hydroquinones of European Patent Application 0,167,168.
• cyan dye-forming image couplers that contain a ureido group in the 2-position.
• a photographic element comprising a support bearing a silver halide emulsion layer having associated therewith a DIR compound having the structure I: wherein: CAR is a carrier moiety, TIME is a timing group and INH is a development inhibitor moiety; together with a cyan dye-forming coupler having the structure II: wherein: m is 0 or 1; n is 0, 1 or 2; Y is halogen, or sulfonyl; Q is -O- or -NH-; R1 is an unsubstituted or a substituted, straight or branched chain alkyl group having from 1 to about 20 carbon atoms, an unsubstituted or a substituted cycloalkyl group having from 3 to about 8 carbon atoms in the ring, an alkylcarbonyl or an alkoxycarbonyl group having from 1 to about 20 carbon atoms in the alkyl or the alkoxy moiety; R2 is as
• substituents include hydroxy, halogen, or alkoxy having from 1 to about 8 carbon atoms.
• substituents include alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, hydroxy, halogen, alkoxycarbonyl, aryloxycarbonyl, carboxy, acyl, acyloxy, carbonamido, carbamoyl, alkylsulfonyl, arylsulfonyl, sulfonamido and sulfamoyl groups wherein the alkyl and aryl substituents, and the alkyl and aryl moieties of the alkoxy, aryloxy, alkylthio, arylthio, alkoxycarbonyl, arylcarbonyl, acyl, acyloxy, carbonamido, carbamoyl, alkylsulfonyl, arylsulfonyl, sulfonamido and sulfamoyl substituents can contain, respectively, from
• Coupling off groups defined by Z are well known to those skilled in the art.
• coupling-off groups include alkoxy, aryloxy, heteroyloxy, sulfonyloxy, acyloxy, acyl, heterocyclyl, sulfonamido, phosphonyloxy and arylazo. These coupling-off groups are described in the art, for example, in U.S. Patent Nos. 2,455,169; 3,227,551; 3,432,521; 3,476,563; 3,617,291; 3,880,661; 4,052,212 and 4,134,766; and in U.K. Patents and published application Nos. 1,466,728; 1,531,927; 1,533,039; 2,006,755A and 2,017,704A.
• Suitable coupling-off groups which can be represented by Z are: Especially preferred Z groups are hydrogen and where R4 is an alkyl or an alkoxy group having from 1 to about 10 carbon atoms.
• cyano group is in the para position with respect to the ureido group and n is 0.
• n 0, the cyano group is para to the ureido group, R1 is alkyl of 1 to about 20 carbon atoms and R2 is hydrogen or alkyl of 1 to about 4 carbon atoms.
• n 0, the cyano group is para to the ureido group, R1 is alkyl of 1 to about 14 carbon atoms, R2 is hydrogen and R3 is alkyl of 2 to about 24 carbon atoms.
• the carrier moiety can be any moiety which, as a result of reaction with oxidized color developing agent, will release the timing group.
• the carrier is a coupler, but it can be another group, such a hydrazide, a hydrazine or a hydroquinone.
• Coupler moieties can form a colored or colorless, diffusible or nondiffusible, reaction product with oxidized color developing agent. Preferred are cyan dye-forming coupler moieties.
• the DIR compounds are DIR couplers represented by the structure where COUP is a coupler moiety.
• COUP is a yellow dye forming coupler moiety having one of the structures where the unsatisfied bond is the point of attachment to the timing group
• BALL is a ballast group such as alkoxycarbonyl, alkoxy, alkylsulfonamido and alkylsulfamyl
• X is as defined below
• Y is alkyl such as methyl and t-butyl, and aryl such as phenyl and alkoxy phenyl.
• TIME timing groups
• timing groups which have the structures: where: p is 1 to 4; q is 0 or 1; A is -O- or -O- -; R5 is hydrogen, alkyl of 1-20 carbon atoms or aryl of 6 to 20 carbon atoms; and X is hydrogen and one or more substituents independently selected from hydroxy, cyano, fluoro, chloro, bromo, iodo, nitro, alkyl, alkoxy, aryl, aryloxy, alkoxycarbonyl, aryloxycarbonyl, carbonamido, and sulfonamido.
• the development inhibitor which is eventually released from the DIR coupler can be any of the development inhibitors known in the art, such as mercaptotetrazoles, selenotetrazoles, mercaptobenzothiazoles, selenobenzothiazoles, mercaptobenzoxazoles, selenobenzothiazoles, mercaptobenzimidazoles, selenobenzimidazoles, benzotriazoles, and benzodiazoles.
• the coupler combinations of this invention can be incorporated in silver halide emulsions and the emulsions can be coated on a support to form a photographic element.
• one or both of the couplers can be incorporated in photographic elements adjacent the silver halide emulsion where, during development, the coupler will be in reactive association with development products such as oxidized color developing agent.
• the photographic elements can be either single color or multicolor elements.
• the cyan dye-forming coupler is usually associated with a red-sensitive emulsion, although it could be associated with an unsensitized emulsion or an emulsion sensitized to a different region of the spectrum.
• Multicolor elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
• the layers of the element, including the layers of the image-forming units, can be arranged in various orders as known in the art.
• a typical multicolor photographic element comprises a support bearing a cyan dye image-forming unit comprising at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta image forming unit comprising at least one green-sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler.
• the element can contain additional layers, such as filter layers, interlayers, overcoat layers, subbing layers, and the like.
• the silver halide emulsions employed in the elements of this invention can be comprised of silver bromide, silver chloride, silver iodide, silver chlorobromide, silver chloroiodide, silver bromoiodide, silver chlorobromoiodide or mixtures thereof.
• the emulsions can include silver halide grains of any conventional shape or size. Specifically, the emulsions can include coarse, medium or fine silver halide grains. 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 54/48,521; 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 polydisperse 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.
• the emulsions can be surface-sensitive emulsions, i.e., emulsions that form latent images primarily on the surfaces of the silver halide grains, or internal latent image-forming emulsions, i.e., emulsions that form latent images predominantly in the interior of the silver halide grains.
• the emulsions can be negative-working emulsions, such as surface-sensitive emulsions or unfogged internal latent image-forming emulsions, or direct-positive emulsions of the unfogged, internal latent image-forming type, which are positive-working when development is conducted with uniform light exposure or in the presence of a nucleating agent.
• 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.
• Typical chemical sensitizers are listed in Research Disclosure , Item 17643, cited above, Section III.
• 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 poly-nuclear cyanines and merocyanines), oxonols, hemioxonols, styryls, merostyryls, and streptocyanines.
• Illustrative spectral sensitizing dyes are disclosed in Research Disclosure , Item 17643, cited above, Section IV.
• Suitable vehicles for the emulsion layers and other layers of elements of this invention are described in Research Disclosure Item 17643, Section IX and the publications cited therein.
• the elements of this invention can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein. These additional couplers can be incorporated as described in Research Disclosure Section VII, paragraph C and the publications cited therein.
• the photographic elements of this invention can contain brighteners (Research Disclosure Section V), antifoggants and stabilizers (Research Disclosure Section VI), antistain agents and image dye stabilizers (Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (Research Disclosure Section VIII), hardeners (Research Disclosure Section XI), plasticizers and lubricants (Research Disclosure Section XII), antistatic agents (Research Disclosure Section XIII), matting agents (Research Disclosure Section XVI) and development modifiers (Research Disclosure Section XXI).
• the photographic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
• Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX.
• Processing to form a visible dye image includes the step of contacting the element with a color developing agent to reduce developable silver halide and oxidize the color developing agent. Oxidized color developing agent in turn reacts with the coupler to yield a dye.
• Preferred color developing agents are p-phenylene diamines.
• 4-amino-3-methyl-N,N-diethylaniline hydrochloride 4-amino-3-methyl-N-ethyl-N- ⁇ -(methanesulfonamido)­ethylaniline sulfate hydrate, 4-amino-3-methyl-N-­ethyl-N- ⁇ -hydroxyethylaniline sulfate, 4-amino-­3- ⁇ -(methanesulfonamido)ethyl-N,N-diethylaniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxy­ethyl)-m-toluidine di-p-toluene sulfonic acid.
• this processing step leads to a negative image.
• this step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the element to render unexposed silver halide developable.
• a direct positive emulsion can be employed to obtain a positive image.
• Couplers of the invention are shown in Tables I and II above.
• Photographic elements were prepared with the following layers, in the order indicated, on a cellulose acetate film support:
• Red sensitized AgBrI emulsion having an average grain diameter of 0.52 ⁇ m, 6.4 mole % I) (1.61g Ag/m2, 2.69g gel/m2), cyan image coupler (see Table III) and cyan DIR coupler (see Table III). Equimolar quantities of image couplers were used in the elements and the DIR couplers were used in amounts that would give essentially the same density and gamma in each of the elements after exposure and processing.
• Color photographic elements were prepared with the following layers, in the order indicated, on a cellulose acetate film support.
• a slow cyan dye-forming layer comprising a blend of a red-sensitized 0.42 ⁇ m silver bromoiodide emulsion (6.1 mol% I) at 1.29g Ag/m2 and a red-sensitized 0.21 ⁇ m AgBrI emulsion (4.8 mole% I) at 0.43g Ag/m2, gelatin (2.69g/m2), a masking coupler 1-hydroxy-4-(4-[2-(8-acetamido-1-hydroxy-3,6-­disulfonaphthyl)azo]phenoxy)-2-( ⁇ -[2,4-di-tert.-amyl-­ phenoxy]butyl)naphthamide dipyridine salt (0.041g/m2), a cyan dye-forming coupler (see Table IV) and a DIR coupler (see Table IV).
• a fast cyan dye-forming layer comprising a 0.76 ⁇ m silver bromoiodide emulsion (6 mole% I) at 1.08g Ag/m2, gelatin (1.61g/m2), a cyan dye-forming coupler (see Table IV) and a DIR coupler (see Table IV).
• a gelatin overcoat layer (2.8g/m2) hardened with bisvinylsulfonylmethane at 1.75% by weight of total gelatin.
• Equimolar quantities of the image coupler (C-1 or II-1) were used and the quantity of DIR coupler (I-2) was chosen to give essentially the same density and gamma in the exposed and processed element.
• Multicolor photographic elements were prepared having the following schematic structure. In this structure the numbers in parenthesis show the coverage in g/m2.
• the amounts of couplers in each of the cyan dye forming layers were chosen to give essentially the same density and contrast in the exposed and processed elements.
• the dried coatings were exposed (1/500 sec), through a graduated density step wedge (Wratten 29 filter), and processed for 3-1/4 minutes in the C-41 process described in the British Journal of Photography Annual, 1977, pages 201-205.
• the AMT acutance values for 35 mm film system were calculated as described in the previous example. Table V EX.

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• 1989
  • 1989-06-29 JP JP1165537A patent/JPH0247650A/ja active Pending
  • 1989-06-30 DE DE68921802T patent/DE68921802T2/de not_active Expired - Fee Related
  • 1989-06-30 AT AT89306645T patent/ATE120285T1/de active
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