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
  • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
  • G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
  • G03C7/30552—Mercapto

Definitions

• This invention relates to a color photographic element comprising a development facilitating concentration of a development facilitator coupler.
• Color photographic images in color photographic materials are commonly formed by a reaction between an oxidized silver halide developing agent and a dye-forming compound commonly called a coupler. This type of reaction has been well known in the photographic art.
• Such color photographic materials employed in the photographic art also contain light-sensitive silver halide emulsion layers.
• Typical color photographic materials are described in, for example, U.S. Patent 4,980,267 and 4,982,996 and European Patent 193,389. However such patents do not disclose means for reducing silver halide concentrations in a color photographic silver halide material, particularly in the magenta layers of such a material.
• the present invention provides for such a reduction in silver concentration by the use of a color photographic element comprising a support bearing at least one photographic silver halide emulsion layer containing at least one magenta image dye-forming coupler wherein the magenta image dye-forming coupler is at least one pyrazolo [3,2-c]-1,2,4-triazole, pyrazolo [1,5-b]-1,2,4-triazole or 1,2,4-anilino-5-pyrazolone; and, the emulsion layer comprises a development facilitator coupler in an amount sufficient to facilitate development, the development facilitator coupler comprising a coupling-off group (A) that is represented by the formula -S-R8-R9 wherein R8 is alkylene containing 1 to 8 carbon atoms and R9 is a water solubilizing group, wherein the concentration of development facilitator coupler enables no bleach accelerator effect upon exposure and processing of the photographic element.
• A coupling-off group
• the amount of the development facilitator coupler is a development facilitating concentration that enables a significant reduction in the concentration of photographic silver halide and or image dye forming coupler required to form a useful color image, especially a magenta image upon exposure and processing of the color photographic element.
• the concentration of photographic silver halide can be lowered by at least 5 wt% measured as silver ion with the concentration being lowered by a least 13 wt% to 25% and sometimes more.
• the concentration of the image dye forming coupler can be reduced by at least 5 wt.% and typically by 23 to 37 wt.%. It will be appreciated both silver halide and image dye forming coupler can be reduced in combination to provide the most useful color image.
• the magenta image dye-forming coupler can be selected from a pyrazolo [3,2-C]-1,2,4-triazole, pyrazolo [1,5-b]-1,2,4-triazole, and anilino-5-pyrazolone.
• a typical example of the pyrazolo [3,2-c]-1,2,4-triazole magenta image dye-forming coupler has the structure: wherein: R1 and R2 individually are substituents that do not adversely affect the coupling action of the coupler; X is hydrogen or a coupling-off group known in the photographic art.
• R1 and R2 individually represent hydrogen or a substituent.
• R1 is a substituent, it can be chosen from any of a number of well-known substituents for that position of a pyrazolo coupler, and is chosen so as to be compatible with the desired characteristics (e.g., activity, hue) of the coupler.
• substituents useful as R1 include a substituted or unsubstituted alkyl group, (e.g., a methyl group, propyl group,) a t-butyl group, a trifluoromethyl group, a tridecyl group, a 3-(2,4-di-t-amylphenoxy) propyl group), a substituted or unsubstituted amyl group (e.g., a phenyl group, a 4-t-butylphenyl group, a 2,4,6,-trimethylphenyl group), a substituted or unsubstituted heterocyclic group (e.g., a 2-furyl group, a 2-thienyl group), a cyano group, a substituted or unsubstituted alkoxy group (e.g, a methoxy group, an ethoxy group), a substituted or unsubstituted aryloxy group (e.g., a pheny
• an acetoxy group, a hexadecanoyloxy group a substituted or unsubstituted caramoyloxy group (e.g., an N-phenylcarbamoyloxy group, an N-ethylcarbamoyloxy group), a substituted or unsubstituted silyoxy group (e.g., a trimethylsilyoxy group), a substituted or unsubstituted sulfonyloxy group (e.g., a dodecylsulfonyloxy group), a substituted or unsubstituted acylamino group (e.g., an acetamido group, a benzamido group), a substituted or unsubstituted anilino group (e.g., a phenylamino group, a 2-chloroanilino group), a substituted or unsubstituted ureido group (e.g.
• a substituted or unsubstituted alkoxycarbonylamino group e.g., a methoxycarboylamino group, a tetradecyloxycarbonylamino group
• a substituted or unsubstituted aryloxycarbonylamino group e.g., a phenoxycarbonylamino group, a 2,4-di-tert-butylphenoxycarbonylamino group
• a substituted or unsubstituted sulfamido group e.g., a methanesulfonamido group, a hexadecanesulfonamido group
• a substituted or unsubstituted carbamoyl group e.g., a N-ethylcarbamoyl group, an N,N-dibutylcarbamoyl group
• a substituted or unsubstituted acyl e.g.
• X represents a hydrogen atom or a group capable of being released by a coupling reaction with an oxidized aromatic primary amine developing agent (referred to herein as a coupling-off group).
• Coupling-off groups are known in the art and may include a group containing an aliphatic group, an aromatic group, a heterocyclic group, an aliphatic, aromatic, or heterocyclic carbonyl group that is bonded to the coupling active carbon via an oxygen atom, a nitrogen atom, a sulfur atom, or a carbon atom, a halogen atom, an aromatic azo group, and the like.
• the aliphatic, aromatic, or heterocyclic group contained in such coupling-off groups may have one or more substitutients, as described above for R1.
• Examples of coupling-off groups include a halogen atom (e.g., fluorine, chlorine, bromine), an alkoxy group (e.g., ethoxy, dodecyloxy, carboxypropyloxy), an aryloxy group (e.g., 4-chlorophenoxy group, a 4-methoxyphenoxy group), an acyloxy group (e.g., an acetoxy group, a tetradecanoyloxy group), an aliphatic or aromatic sulfonyloxy group (e.g., a methanesulfonyloxy group, a toluenesulfonyloxy group), an acylamino group (e.g., a dichloroacetylamino group, a trifluoroacetylamino group), an aliphatic or aromatic sulfonamido group (e.g., a methanesulfonamido group, a p
• Typical pyrazole [3,2-c]-1,2,4-triazole magenta image dye-forming couplers within the described structure are disclosed in, for example, U.S. Patents 4,777,121; 4,443,536; 5,019,489; European Patent 284,240; U.S. Patent 4,808,502; U.S. Patent 4,835,094; European Patent 285,274; and U.S. Patent 4,960,685.
• Especially useful magenta image dye-forming couplers are:
• Useful magenta image dye forming couplers include pyrazolotriazole couplers comprising pyrazolo-[1,5-b]-1,2,4-triazole couplers. Such couplers are represented by the formula: wherein R1, R2 and X are defined above.
• Typical pyrazolo [1,5-b]-1,2,4-triazole couplers are described in for example U.S Patents 4,540,654; 4,659,652; 4,774,172; 4,822,730; and 4,925,781; Japanese Published Patent Application No. 61-147254; European Patents 226,849;294,785; 119,860 and 234,428.
• Useful image dye forming couplers also comrise anilino-5-pyrazolone couplers.
• Such couplers include those represented by the formula: wherein R3 is a substitutent that does not adversely affect the coupling action of the coupler; typically an aryl group; preferably 2,4,6-trichlorophenyl; R4 is an unsubstituted or substituted anilino group; and, X is hydrogen or a coupling group known in the photographic art.
• R3 is typically a substituted or unsubstituted aryl group (e.g., phenyl, 2-chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3,5-dibromophenyl, 2-cyanophenyl, 4-cyanophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-methylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 4-butylphenyl, 2-trifluoromethylphenyl, 2,6-dichloro-4-methoxycarbonylphenyl, 2,6-dichloro-4-tetradecyloxycarbonylphenyl, 2,6-dichloro-4-cyanophexyl, 2-ethoxyphenyl, 4-phenylphenyl, 4-phenoxyphenyl, 2-methyl-5-
• R4 is typically an unsubstituted or substituted anilino group represented by the formula: wherein, R5 and R6 and R7 individually are hydrogen or a substituent that does not adversely affect the coupling action of the coupler, and at least one of R5, R6 and R7 is a ballast group known in the photographic art.
• R5, R6 and R7 individually are, for example, hydrogen alkyl (e.g., methyl, t -butyl, octyl, and dodecyl), alkoxy (e.g., methoxy, ethoxy, octyloxy), alkylthio (e.g., methylthio, butylthio, dodecylthio), an amido group (e.g., acetamido, butyramido, methylsulfonamido, diacylamido, succinamido), a halogen atom (e.g., fluorine, chlorine, or bromine), a hydroxy group, a cyano group or a photographic ballast group known in the photographic art.
• alkyl e.g., methyl, t -butyl, octyl, and dodecyl
• alkoxy e.g., methoxy, ethoxy, o
• X is hydrogen or a coupling-off group as defined above.
• Typical anilino-5-pyrazole couplers are described in, for example, U.S Patents 4,346,165; 3,907,571; 4,243,747; 2,343,703; 3,935,015; 4,351,897; 4,477,563; 4,853,319; 3,127,967; 3,519,429; 4,243,747; and 4,443,536; and, European Patent 226,664;
• Combinations of magenta image dye-forming couplers are also useful.
• development facilitating means the use of a compound that enables lowering of the silver halide concentration or coupler concentration or both and whose presence yields increased silver development.
• the compound's presence can yield an increase in developed silver of at least 3% measured as developed silver in mg/m2.
• the development facilitating concentration is one which is effective in reducing the concentration of silver halide measured as silver ion and/or in reducing the concentration of magenta dye forming couplers which is required to provide a developed image.
• the development facilitating concentration can range from 0.1 to 65 mg/m2 of a development facilitator coupler, the coupler selected so as to avoid bleach acceleration.
• the development-facilitating concentration can range from 0.25 to 33 mg/m2.
• a development facilitator coupler such as, typically requires a development facilitating concentration within the range of 0.25 to 33 mg/m2.
• the development-facilitator coupler useful in the invention includes a coupling-off group (A) that is represented by the formula -S-R8-R9 wherein R8 is alkylene containing 1 to 8 carbon atoms, such as -CH2-, -CH2CH2-, or R9 is a water-solubilizing group, such as carboxyl.
• A coupling-off group
• a typical developing facilitating coupler is represented by the structure: where COUP is a coupler moiety known in the photographic art such as a yellow, magenta or cyan dye forming coupler moiety, and the remainder of the molecule defined by S-R8-R9 is bonded to the coupling position of COUP, where R8 and R9 are as defined above.
• a preferred color photographic element according to the invention comprises a preferred development facilitator coupler having the formula: or
• the color photographic element comprises at least one red-sensitive photographic silver halide emulsion layer containing at least one cyan image dye-forming coupler, at least one green-sensitive photographic silver halide emulsion layer containing at least one magenta image dye-forming coupler and at least one blue-sensitive silver halide emulsion layer containing at least one yellow image dye-forming coupler and wherein the development facilitator coupler is in the green-sensitive silver halide emulsion layer.
• the silver halide emulsions employed in the elements of this invention can be either negative-working or positive-working. Suitable emulsions and their preparation are described in Research Disclosure Sections I and II and the publications cited therein. Suitable vehicles for the emulsion layers and other layers of elements of this invention are described in Research Disclosure Section IX and the publications cited therein.
• the elements of the invention can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein. These couplers can be incorporated in the elements and emulsions as described in Research Disclosure Section VII, paragraph C and the publications cited therein.
• the photographic elements of this invention or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilizers (See Research Disclosure Section VI), antistain agents and image dye stabilizers (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section IX), plasticizers and lubricants (See Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
• brighteners see Research Disclosure Section V
• antifoggants and stabilizers See Research Disclosure Section VI
• antistain agents and image dye stabilizers see Research Disclosure Section VII, paragraphs I and J
• light absorbing and scattering materials see Research Disclosure Section VIII
• hardeners see Research Disclosure Section IX
• plasticizers and lubricants See Research Disclosure Section XII
• antistatic agents see Research Disclosure Section XIII
• matting agents see Research Disclosure
• 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.
• the processing step described above gives 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 uniformly fogging the element to render unexposed silver halide developable.
• a direct positive emulsion can be employed to obtain a positive image.
• Coupler solvents useful in the present invention include:
• a three color photographic film was prepared as follows using conventional surfactants, and antifoggants and the materials indicated. After providing a developable image and then processing in accordance with the Kodak C-41 process (British Journal of Photography, pp. 196-198(1988)) excellent results were obtained.
• a three color photographic film was prepared as follows using conventional surfactants, and antifoggants and the materials indicated. After providing a developable image and then processing in accordance with the Kodak C-41 process (British Journal of Photography, pp. 196-198(1988)) excellent results were obtained.
• Coupler solvent selection can influence stability of the photographic element when keeping. For example, improved stability can be observed when the coupler solvent (A) is used.

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Citations (2)

• 1992
  • 1992-12-22 EP EP92204055A patent/EP0550109A1/de not_active Withdrawn
• 1993
  • 1993-01-04 JP JP4993A patent/JPH05249627A/ja active Pending

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