EP0512304B1 - Farbphotographische Pyrazolotriazol Magentakuppler enthaltende Silberhalogenidelemente - Google Patents

Farbphotographische Pyrazolotriazol Magentakuppler enthaltende Silberhalogenidelemente Download PDF

Info

Publication number
EP0512304B1
EP0512304B1 EP92106738A EP92106738A EP0512304B1 EP 0512304 B1 EP0512304 B1 EP 0512304B1 EP 92106738 A EP92106738 A EP 92106738A EP 92106738 A EP92106738 A EP 92106738A EP 0512304 B1 EP0512304 B1 EP 0512304B1
Authority
EP
European Patent Office
Prior art keywords
group
couplers
coupler
silver halide
pat
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP92106738A
Other languages
English (en)
French (fr)
Other versions
EP0512304A1 (de
Inventor
Enzo Coraluppi
Vinicio Busatto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GlassBridge Enterprises Inc
Original Assignee
Imation Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Imation Corp filed Critical Imation Corp
Publication of EP0512304A1 publication Critical patent/EP0512304A1/de
Application granted granted Critical
Publication of EP0512304B1 publication Critical patent/EP0512304B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/381—Heterocyclic compounds
    • G03C7/382—Heterocyclic compounds with two heterocyclic rings
    • G03C7/3825—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms
    • G03C7/3835—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms four nitrogen atoms

Definitions

  • the present invention relates to a silver halide color photographic light-sensitive element containing a photographic coupler and, more in particular, a lH-pyrazolo[3,2-c]-1,2,4-triazole magenta coupler having at a position other than the coupling position a ballasting group.
  • color images are obtained in the photographic silver halide elements by reaction between the oxidation product of an aromatic primary amine developing agent and a dye-forming coupler and it is known to use a combination of a yellow coupler, a cyan coupler and a magenta coupler as such dye-forming couplers.
  • 5-pyrazolone couplers are normally used as magenta dye-forming couplers. It is known that dyes formed from 5-pyrazolone couplers are excellent in fastness to heat and light and have the predominant absorption which approaches to the ideal one, but they tend to have absorptions other than the predominant one at about 430 nm which necessitates the use of masking couplers or other masking techniques. The dyes also display low resistance to the action of formaldehyde.
  • magenta dye-forming couplers For overcoming these problems, there have been proposed as magenta dye-forming couplers, pyrazolobenzimidazole couplers as described in GB Pat. No. 1,047,612, pyrazolo-triazole couplers as described in US Pat. No. 3,725,067, and, more recently, 1H-imidazolo-[1,2-b]-pyrazole couplers as described in US Pat. No. 4,500,630, 1H-pyrazolo[1,3-b]-1,2,4-triazole as described in EP Pat. No. 119860, 1H-pyrazo]o[1,5-d]-tetrazole as described in Research Disclosure No. 24220, and 1H-pyrazolo[1,5]-pyrazole as described in JP Pat. Appl. No. 43659/85.
  • couplers When intended for incorporation in photographic elements, couplers are normally dispersed with the aid of a high boiling solvent or adsorbed onto a polymer latex. Couplers are rendered nondiffusible in the photographic elements and compatible with the coupler solvent or the polymer latex by including a ballast group on the coupler in a position other than the coupling position.
  • Pyrazolo-triazole and pyrazolobenzimidazole magenta couplers with a ballast group having a p-hydroxyphenylsulfonyl group or a p-hydroxyphenylsulfinyl group as a terminal group are described in EP Pat. Appl. No. 73636.
  • Pyrazolobenzimidazole, pyrazolotriazole and imidazopyrazole magenta couplers having a subsituted p-hydroxyphenylsulfonyl group or a substituted p-hydroxyphenylsulfinyl group as a terminal group are described in US Pat. No. 4,513,082.
  • Pyrazolotriazole magenta couplers with a ballast group having an aminosulfonyl or aminocarbonyl group as a terminal group are described in US Pat. Nos. 4,548,899 and 4,822,730.
  • Pyrazolotriazole magenta couplers with a ballast group comprising a carboxy group are described in EP Pat. Appl. No. 284240 and in US Pat. No. 4,835,094.
  • couplers may overcome the above-described problems of 5-pyrazolone magenta couplers, there is a continuing desire to improve, or optimize the couplers for particular applications.
  • Many properties of the coupler and the resulting dye are desirably modified, in particular providing pyrazoloazole couplers which yield dyes having predominant absorption maxima at wavelengths substantially corresponding to that of 5-pyrazolone magenta couplers.
  • the invention relates to a silver halide color photographic element comprising a support and at least one silver halide emulsion layer containing at least one nondiffusible magenta coupler of the 1H-pyrazolo[3,2-c]--1,2,4-triazole series having at a position other than the coupling position a group expressed by the general formula (I) wherein L is an aralkylene divalent linking group containing a ballasting residue and having the arylene group of said aralkylene group directly connected to -(NH) n -SO 2 -, n is 0 or 1, characterized in that R is a substituent selected within the group consisting of a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a sulfonamido group and an acetylsulfonamido group, with the proviso that the phenyl group containing the substituent R does not include a
  • Magenta dyes can be obtained by chromogenic development of said magenta couplers with high reactivity, high color density, little absorption in the blue and green regions, little change in hue irrespective of storage conditions, and absorption maxima at wavelengths corresponding to that of 5-pyrazolone magenta couplers.
  • magenta couplers according to the present invention can be expressed by the following general formula (II) wherein R 1 is a hydrogen atom, an alkyl group or an aryl group, Z is a hydrogen atom, a halogen atom or a group which can be eliminated upon coupling reaction with the oxydized product of a color developing agent and L, n and R each has the same meaning as in the general formula (I).
  • R1 in formula (II) represents a hydrogen atom, an alkyl group, or an aryl group.
  • Preferred alkyl groups are those having 1 to 8 carbon atoms. More preferred alkyl groups are those having 1 to 4 carbon atoms, such as methyl, trifluorometyl, ethyl, ethoxyethyl and t-butyl.
  • a preferred aryl group represented by R 1 is a phenyl group which may be substituted, such as p-methoxyphenyl, 4-t-butylphenyl or m-chloromethylphenyl.
  • Z represents a hydrogen atom or a group which can be eliminated upon coupling reaction with the oxidized product of a color developing agent.
  • group include a halogen atom (e.g. chlorine or fluorine) or a group, preferably a cyclic group, which is linked to the coupling position through an oxygen atom, a nitrogen atom or a sulfur atom (e.g. an aryloxy group such as phenoxy, p-methoxyphenoxy or p-tert.butylcarbonamidophenoxy, an arylthio group such as phenylthio, and a heterocyclic thio group such as 1-ethyltetrazole-5-thioyl).
  • a halogen atom e.g. chlorine or fluorine
  • a group preferably a cyclic group, which is linked to the coupling position through an oxygen atom, a nitrogen atom or a sulfur atom
  • an aryloxy group such as phenoxy, p
  • eliminable group is a cyclic group
  • it may be attached to the coupling position of the coupler molecule directly through an atom which forms part of a ring, e.g. a nitrogen atom.
  • a halogen atom is preferred, and a chlorine atom is particularly preferred.
  • R represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, e.g. methyl, ethyl, propyl, butyl, which may be substituted with known substituents such as halogen atoms, an alkoxy group of 1 to 4 carbon atoms, e.g. methoxy, ethoxy, propoxy, butoxy which may be substituted, a sulfonamido group or an acetylsulfonamido group.
  • the divalent linking group L attached to a non-coupling position of the 1H-pyrazolo[3,2-c]-1,2,4-triazole magenta coupler is an aralkylene group having an alkylene group linked to an arylene group either directly or having in the main chain of said aralkylene group -O-, -S-, -NHCO-, -CONH-, -NHSO 2 - or -SO 2 NH-.
  • the arylene group is preferably a phenylene group which may substituted, e.g. with an alkyl, alkoxy, halogen or acylamino.
  • the divalent linking group L contains a ballasting residue which may consist of the totality of the divalent linking group or may be formed by said divalent linking group L containing a ballast residue in the form of a substituent.
  • the alkylene group for example , may be a 1,2-alkylene group with up to 20 carbon atoms, or the arylene group may be substituted, e.g. with an alkoxy group or acylamino group containing up to 20 carbon atoms.
  • ballasting groups enable the magenta couplers according to this invention to be incorporated in a nondiffusible form in the gelatin layers used in the silver halide photographic elements.
  • These groups are organic groups generally containing straight or branched chain aliphatic groups with generally 8 to 20 carbon atoms.
  • These ballasting groups are attached to the coupler molecule either directly or indirectly, e.g. through one of the following groups: NHCO, NHSO 2 , NR (wherein R represents hydrogen or alkyl), COO, O or S.
  • a preferred divalent linking group L is represented by the general formula (III) wherein R 2 is an alkyl group of 4 to 20 carbon atoms.
  • Examples of useful divalent linking group are as follows:
  • Particularly preferred couplers used in this invention have the general formula (IV): wherein R, R 1 , R 2 and Z are as defined above.
  • magenta couplers for use in the present invention may be readily synthesized by any of the known techniques. Specific examples of the couplers for use in the present inventiom are shown below.
  • magenta dye forming couplers for use in this invention may be incorporated in a silver halide photographic material by any of the methods known in the art for incorporation of nondiffusible couplers, such as, for example, a solid dispersion method, a latex dispersion method, and preferably an oil dispersion method.
  • nondiffusible couplers such as, for example, a solid dispersion method, a latex dispersion method, and preferably an oil dispersion method.
  • the couplers can be dissolved in a high boiling water insoluble solvent and the resulting solution emulsified into an aqueous medium as described for example in US Pat. Nos.
  • hydrophobic couplers are dissolved in said high boiling organic solvents in combination with low boiling organic solvents and the resulting solution emulsified into the aqueous medium as described for example in US Pat. Nos. 2,801,170, 2,801,171, 2,949,360, etc.
  • Typical known high boiling solvents include phthalate esters (e.g. dibutyl phthalate and dioctyl phthal- ate), phosphate esters (e.g. tricresyl phosphate and trioctyl phosphate) and N-substituted acid amides (e.g. N,N-diethyllauramide).
  • Typical known low boiling solvents include ethyl acetate, butyl acetate, methyl ethyl ketone, cyclohexanone, 2-ethoxyethyl acetate, dimethylformamide, etc. Specific examples of the latex dispersion method are described in US Pat. No. 4,199,363, etc.
  • the pyrazolotriazole magenta couplers for use in this invention are preferably incorporated in light-sensitive silver halide emulsion layers.
  • the addition amount thereof is from 0.003 to 1 mole, preferably from 0.005 to 0.3 mole per mole of silver halide for color photographic light sensitive elements.
  • the silver halide emulsion layer containing the pyrazolotriazole magenta couplers described above or a layer sensitive to the same region of the visible spectrum may contain conventional magenta dye-forming couplers, DIR couplers, BAR couplers, FAR couplers, DAR couplers and colored couplers (all these couplers exhibiting variuos effects upon processing) as described below.
  • the photographic elements of the present invention are preferably multilayer color elements comprising a blue sensitive or sensitized silver halide emulsion layer associated with yellow dye-forming couplers, a green sensitized silver halide emulsion layer associated with magenta dye-forming couplers and a red sensitized silver halide emulsion layer associated with cyan dye-forming couplers, at least one of the couplers in the element being a coupler as described above.
  • Each layer can comprise a single emulsion layer or multiple emulsion sub-layers sensitive to a given region of the visible spectrum.
  • multilayer elements contain multiple blue, green or red sublayers, there can be in any case relatively faster and slower sub-layers.
  • the photographic elements can contain additional layers, such as filter layers, interlayers, overcoat layers, subbing layers, and the like.
  • Coupler is positioned in such a relation to the silver halide emulsion layer that the coupler and the layer are capable of interacting to give rise to an imagewise correspondence between the silver image formed on development and the color image produced from the coupler. This is generally achieved by arranging the coupler in the silver halide emulsion layer or in an adjacent layer of binder which may be light-insensitive.
  • Preferred couplers for use in this invention include those which are nondiffusible due to the presence of hydrophobic ballast group in the molecule.
  • Typical examples of useful color couplers are naphtholic, phenolic or pyrazoloazole cyan dye-forming couplers, pyrazolone or pyrazoloazole magenta dye-forming couplers and open chain or heterocyclic ketomethylene yellow dye-forming couplers. Cyan, magenta and yellow couplers, which can be used in this invention, are described in Research Disclosures No. 17643, Chapter VII (December 1978) and No. 18717 (November 1979).
  • two-equivalents yellow couplers are preferably used, such as those which are oxygen atom-releasing yellow couplers and nitrogen atom-releasing yellow couplers.
  • Illustrative yellow dye-forming couplers are shown in US Pat. Nos. 2,407,210, 2,875,057, 3,265,506, 3,408,194, 3,447,928, 3,933,501, 4,022,620, 4,326,024 and 4,401,752, in GB Pat. Nos.
  • Cyan couplers which can be used in this invention include naphtholic, phenolic and pyrazoloazole couplers.
  • Specific examples of the naphtholic couplers are the naphtholic couplers described in US Pat. No. 2,474,293 and the oxygen atom-releasing two-equivalent naphtholic couplers described in US Pat. Nos. 4,052,212, 4,146,396, 4,228,233, and 4,296,200.
  • Specific examples of the phenolic couplers are described in US Pat. Nos. 2,369,929, 2,423,730, 2,772,162, 2,895,826, and 3,772,002.
  • Specific examples of pyrazoloazole cyan couplers are described in EP Pat. Appl. 287,265.
  • Cyan couplers preferably used in this invention are 2,5-diacylamino substituted phenolic cyan couplers described in US Pat. Nos. 2,772,162, 3,758,308, 4,126,396, 4,334,011, and 4,327,173, in DE Pat. Appl. No. 3,229,729 and in JA Pat. Appl. 42761/83, and the phenolic couplers having a phenylureido group at the 2-position and an acylamino group at the 5-position described in US Pat. Nos. 3,446,622, 4,333,999, 4,451,559, 4,427,767, etc.
  • magenta dye-forming couplers defined above according to this invention may be used either alone or in combination with themselves. If desired, they may be used in combination with known magenta dye-forming couplers such as pyrazolone, indazolone, cyanoacetyl, pyrazoloazole and pyrazolotriazole couplers.
  • Useful magenta dye-forming couplers may include those described in US Pat. Nos. 2,600,788, 2,983,608, 3,026,653, 3,127,269, 3,311,476, 3,419,391, 3,519,429, 3,558,319, 3,582,322, 3,615,506, 3,384,908, and 3,891,445, in DE Pat. No. 1,810,464, in DE Pat.
  • the color couplers may be 4-equivalent or they may be 2-equivalent couplers.
  • the latter are derived, as is known, from 4-equivalent couplers in that they contain, in the coupling position, a group which is released in the coupling reaction.
  • the 2-equivalent couplers include both those which are colourless and those which have an intense color which disappears during the coupling reaction and may be replaced by the color of the image dye produced.
  • the latter (masking couplers) are used, together with the above described couplers, for correcting the undesired absorption of the image dyes of the magenta and cyan couplers at a short wavelength region.
  • Typical examples of masking couplers are the yellow-colored magenta couplers described in US Pat. No. 4,163,670 and in JA Pat. No. 39413/82, and the magenta-colored cyan couplers described in US Pat. Nos. 4,004,929, 4,138,258, and in GB Pat. No. 1,146,368.
  • couplers providing diffusible colored dyes can be used together with the above mentioned couplers for improving graininess and specific examples of these couplers are magenta couplers described in US Pat. No. 4,366,237 and GB Pat. No. 2,125,570 and yellow, magenta and cyan couplers described in EP Pat. No. 96,873, and in DE Pat. Appl. No. 3,324,533.
  • 2-equivalent couplers those couplers wich carry in the coupling position a group which is released in the color development reaction to give a certain photographic activity, e.g. as development inhibitor or accelerator or bleaching accelerator, either directly or after removal of one or further groups from the group originally released.
  • 2-equivalent couplers include the known DIR couplers as well as DAR, FAR and BAR couplers. Typical examples of said couplers are described in DE Pat. Appl. Nos.
  • the light-sensitive silver halide color photographic element may contain high molecular weight color couplers as described for example in US Pat. No. 4,080,211, in EP Pat. Appl. No. 27,284 and in DE Pat. Appl. Nos. 1,297,417, 2,407,569, 3,148,125, 3,217,200, 3,320,079, 3,324,932, 3,331,743, and 3,340,376.
  • the silver halide emulsions used in the present invention may be fine dispersions of silver chloride, silver bromide, silver chloro-bromide, silver iodo-bromide and silver chloro-iodo-bromide grains in a hydrophilic binder.
  • the silver halide grains may have different phases between the inside thereof and the surface thereof. Also, the silver halide grains may be ones forming mainly surface latent images or ones forming latent images mainly in the inside thereof.
  • hydrophilic binder any hydrophilic polymer of those conventionally used in photography can be advantageously employed including gelatin, a gelatin derivative such as acylated gelatin, graft gelatin, etc., albumin, gum arabic, agar agar, a cellulose derivative, such as hydroxyethyl-cellulose, carboxymethyl-cellulose, etc., a synthetic resin, such as polyvinyl alcohol, polyvinylpyrrolidone, polyacrylamide, etc.
  • Preferred silver halide grains are silver iodo-bromide or silver iodo-bromo-chloride containing 1 to 20% by mole of silver iodide per mole of silver halide.
  • the silver halide grains may have any crystal form such as cubic, octahedral, spherical or tabular or a mixed crystal form.
  • the silver halide grains may have a uniform grain size or a broad grain size distribution.
  • the size of the silver halide ranges from about 0.1 to 5 ⁇ m.
  • the silver halide grains may have different phases between the inside thereof and the surface thereof. Also, the silver halide grains may be ones forming latent images mainly on the surfaces thereof or ones forming latent images mainly in the insides thereof.
  • the total silver halide content in the blue sensitive, green sensitive and red sensitive emulsion layers of the photographic elements comprising the pyrazolotriazole couplers according to this invention is 7.5 g/m 2 or more as calculated on silver, with proportions in each sensitive layer varying as desired according to the particular needs.
  • the silver halide emulsions may be prepared using a single-jet method, a double-jet method, or a combination of these methods or may matured using, for example, an ammonia method, a neutralization method, an acid method, etc., as described in Research Disclosure 17643, I and II, December 1978.
  • the emulsions which can be used in the present invention can be chemically and optically sensitized, as described in Research Disclosure 17643, III and IV, December 1978. They can contain optical brighteneres, antifogging agents and stabilizers, antistain agents and image dye stabilizers, filter and antihalo dyes, hardeners, coating aids, plasticizers and lubricants, matting agents, development modifiers and other auxiliary substances, as described for example in Research Disclosure 17643, V, VI, VII, VIII, XI, XIII, XVI and XXI, December 1978.
  • the layers of the photographic element can contain various colloids, alone or in combination, such as binders, as for example described in Research Disclosure 17643, IX, December 1978.
  • the above described layers can be coated onto several support bases (cellulose triacetate, paper, resin-coated paper, polyester) by adopting various methods, as described in Research Disclosure 17643, XV and XVI, December 1978.
  • the light-sensitive silver halides contained in the photographic element after exposure can be processed to form a visible image by associating the silver halides with an aqueous alkaline medium in the presence of a developing agent contained in the medium or in the element. Processing formulations and techniques are described in Research Disclosure 17643, XIX, XX and XXI, December 1978.
  • Film 1 was prepared by coating a cellulose triacetate support base, subbed with gelatin, with the following layers in the following order: (a) a layer of green-sensitized silver halide emulsion comprising a blend of a low-sensitivity silver bromoiodide emulsion (having 2.5% silver iodide moles and a mean grain size of 0.18 ⁇ m) and a medium-sensitivity silver chloro-bromo-iodide (having 7.2% silver iodide moles and 5% silver chloride moles and a mean grain size of 0.4 ⁇ m) coated at a silver coverage of 2.0 g/m 2 and a gelatin coverage of 1.8 g/m 2 and the magenta dye forming coupler A, dispersed in the layer with high boiling water insoluble organic solvents, at a coverage of 1.18 millimole/m 2 .
  • a layer of green-sensitized silver halide emulsion comprising a blend of a low
  • Film 2 (comparison) was prepared as Film 1, except that the magenta dye forming coupler was coupler B.
  • Film 3 (invention) was prepared as Film 1, except that the magenta dye forming coupler was coupler (1).
  • Film 4 (invention) was prepared as Film 1, except that the magenta dye forming coupler was coupler (2).
  • magenta couplers of the present invention have good values of fog, sensitivity and contrast, and absorption maxima comparable with that of the 5-pyrazolone magenta coupler A.
  • the comparison pyrazolotriazole coupler B has inferior photographic results and is more reddish in hue.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Claims (6)

  1. Farbphotographisches Silberhalogenidelement, umfassend einen Träger und wenigstens eine Silberhalogenidemulsionsschicht, die wenigstens einen diffusionsunfähigen Magentakuppler der 1H-Pyrazolo[3,2-c]-1,2,4-triazol-Reihe mit einem Rest der allgemeinen Formel an einer anderen als an der Kupplungsposition enthält,
    Figure imgb0024
     wobei L ein zweiwertiger verknüpfender Aralkylenrest ist, welcher eine Ballastgruppe enthält, und wobei der Arylenrest des Aralkylenrests direkt an -(NH)n-SO2-gebunden ist, und n 0 oder 1 beträgt, dadurch gekennzeichnet, daß R ein Substituent ist, ausgewählt aus einem Wasserstoffatom, einem Alkylrest mit 1 bis 4 Kohlenstoffatomen, einem Alkoxyrest mit 1 bis 4 Kohlenstoffatomen, einem Sulfonamidrest und einem Acetylsulfonamidrest, mit der Maßgabe, daß die Phenylgruppe, die den Rest R enthält, keinen Substituenten mit mehr als 4 Kohlenstoffatomen umfaßt.
  2. Photographisches Element nach Anspruch 1, wobei in der Hauptkette des Aralkylenrests -O-, -S-, -NHCO-, CONH-, NHSO2- oder -SO2NH- enthalten sein kann.
  3. Photographisches Element nach Anspruch 1, wobei L einen zweiwertigen Rest der allgemeinen Formel darstellt,
    Figure imgb0025
     wobei R2 ein Alkylrest mit 4 bis 20 Kohlenstoffatomen ist.
  4. Photographisches Element nach Anspruch 1, wobei der Kuppler die allgemeine Formel aufweist,
    Figure imgb0026
     wobei R1 ein Wasserstoffatom, einen Alkylrest oder einen Arylrest bedeutet, und Z ein Wasserstoffatom, ein Halogenatom oder einen Rest bedeutet, der bei der Kupplungsreaktion mit dem oxidierten Produkt eines Farbentwicklungsmittels eliminicrt wcrden kann.
  5. Photographisches Element nach Anspruch 1, wobei der Kuppler die allgemeine Formel aufweist,
    Figure imgb0027
     wobei R2 ein Alkylrest mit 4 bis 20 Kohlenstoffatomen ist, R1 ein Wasserstoffatom, einen Alkylrest oder einen Arylrest bedeutet und Z ein Wasserstoffatom, ein Halogenatom oder einen Rest bedeutet, der bei dcr Kupplungsreaktion mit dem oxidierten Produkt eines Farbentwicklungsmittels eliminiert werden kann.
  6. Photographisches Element nach Anspruch 1, wobei der Kuppler die allgemeine Struktur aufweist:
    Figure imgb0028
    Figure imgb0029
     oder
    Figure imgb0030
EP92106738A 1991-05-09 1992-04-21 Farbphotographische Pyrazolotriazol Magentakuppler enthaltende Silberhalogenidelemente Expired - Lifetime EP0512304B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI911263A IT1247912B (it) 1991-05-09 1991-05-09 Elementi fotografici a colori agli alogenuri d'argento contenenti un copulante magenta pirazolotriazolico
ITMI911263 1991-05-09

Publications (2)

Publication Number Publication Date
EP0512304A1 EP0512304A1 (de) 1992-11-11
EP0512304B1 true EP0512304B1 (de) 1997-12-17

Family

ID=11359865

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92106738A Expired - Lifetime EP0512304B1 (de) 1991-05-09 1992-04-21 Farbphotographische Pyrazolotriazol Magentakuppler enthaltende Silberhalogenidelemente

Country Status (4)

Country Link
EP (1) EP0512304B1 (de)
JP (1) JP3165733B2 (de)
DE (1) DE69223545T2 (de)
IT (1) IT1247912B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60107132T2 (de) 2000-03-07 2005-11-03 Fuji Photo Film Co. Ltd., Minamiashigara Lichtempfindliches photographisches Silberhalogenidmaterial
JP4253131B2 (ja) 2000-08-14 2009-04-08 富士フイルム株式会社 ハロゲン化銀カラー写真感光材料及びそれに用いる化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06100802B2 (ja) * 1985-10-14 1994-12-12 富士写真フイルム株式会社 ハロゲン化銀カラ−写真感光材料
DE3860351D1 (de) * 1987-03-09 1990-08-30 Eastman Kodak Co Photographische silberhalogenidmaterialien und verfahren, das einen pyrazoloazolkuppler enthaelt.

Also Published As

Publication number Publication date
DE69223545D1 (de) 1998-01-29
EP0512304A1 (de) 1992-11-11
IT1247912B (it) 1995-01-05
ITMI911263A1 (it) 1992-11-09
DE69223545T2 (de) 1998-06-25
ITMI911263A0 (it) 1991-05-09
JPH05150419A (ja) 1993-06-18
JP3165733B2 (ja) 2001-05-14

Similar Documents

Publication Publication Date Title
US4588679A (en) Color photographic silver halide light-sensitive material
US3933500A (en) Color photographic light-sensitive material
US4585732A (en) Silver halide photographic light-sensitive material
US4636457A (en) Process for forming direct positive images, direct positive silver halide elements, compositions and compounds as characteristics feature of such processes and elements
US4327175A (en) Silver halide color photographic light-sensitive material
US4072525A (en) Silver halide photographic material containing two-equivalent color coupler
US4835094A (en) Color photographic recording material containing a color coupler of the pyrazoloazole series
JP2753292B2 (ja) ハロゲン化銀カラー写真感光性材料
EP0356925A2 (de) Photographisches Element sowie Verfahren mit einem einen Entwicklunsinhibitor freisetzenden Kuppler und einem einen gelben Farbstoff liefernden Kuppler
US5143821A (en) Color photographic material comprising a 2-alkoxy pyrazolo[1,5-a]benzimidazole color coupler
EP0433947B1 (de) Farbphotographisches Element und Verfahren
EP0512304B1 (de) Farbphotographische Pyrazolotriazol Magentakuppler enthaltende Silberhalogenidelemente
USRE29379E (en) Color photographic light-sensitive material
US4935321A (en) Photographic recording material comprising a dye image-forming compound
EP0309159B1 (de) Photographisches Eintragungsmaterial, enthaltend farbbildende Kupplerverbindungen
US6043017A (en) Color photographic silver halide material
US4199361A (en) Color photographic light-sensitive element
US4977072A (en) Color photographic recording material containing color couplers
US5015565A (en) Color photographic recording material
US5332656A (en) Silver halide color photographic light-sensitive material
EP0456443A1 (de) Farbfotografisches, lichtempfindliches, Silberhalogenid enthaltendes Material
EP0309158B1 (de) Photographisches Eintragungsmaterial mit einer ein purpurrotes Farbbild bildenden Kupplerverbindung
US4532202A (en) Coupler for photography
US5496692A (en) Silver halide color photographic light-sensitive material
JPS6257024B2 (de)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB IT

17P Request for examination filed

Effective date: 19930506

17Q First examination report despatched

Effective date: 19960429

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB IT

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: IMATION CORP.

REF Corresponds to:

Ref document number: 69223545

Country of ref document: DE

Date of ref document: 19980129

ET Fr: translation filed
ITF It: translation for a ep patent filed

Owner name: IMATION S.P.A.

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20030403

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20030430

Year of fee payment: 12

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041103

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041231

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20050314

Year of fee payment: 14

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050421

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20060421

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20060421