EP0415056B1 - Matériau d'enregistrement pour photographie en couleurs à un coupleur libérant un composé photographiquement actif - Google Patents

Matériau d'enregistrement pour photographie en couleurs à un coupleur libérant un composé photographiquement actif Download PDF

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Publication number
EP0415056B1
EP0415056B1 EP90113825A EP90113825A EP0415056B1 EP 0415056 B1 EP0415056 B1 EP 0415056B1 EP 90113825 A EP90113825 A EP 90113825A EP 90113825 A EP90113825 A EP 90113825A EP 0415056 B1 EP0415056 B1 EP 0415056B1
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Prior art keywords
coupler
dir
silver halide
halide emulsion
recording material
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EP90113825A
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German (de)
English (en)
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EP0415056A2 (fr
EP0415056A3 (en
Inventor
Peter Dr. Bergthaller
Thomas Dr. Krüger
Rudolf Stolzenburg
Dirk Dr. Hübner
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
    • G03C7/30535—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site not in rings of cyclic compounds
    • 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
    • G03C7/30558—Heterocyclic group
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/156—Precursor compound
    • Y10S430/158—Development inhibitor releaser, DIR

Definitions

  • the invention relates to a color photographic recording material having at least one light-sensitive silver halide emulsion layer which contains a coupler which, during color development, contains a photographically active group, e.g. releases a development inhibitor.
  • DIR development inhibitor releasing
  • the DIR compounds can be those which release an inhibitor residue with the oxidation product of a color developer to form a dye (DIR coupler), or to those that release the inhibitor without simultaneously forming a dye. The latter are also referred to as DIR connections in the narrower sense.
  • DIR couplers are known, for example, from US-A-3 148 062, US-A-3 227 554, US-A-3 615 506, US-A-3 617 291 and DE-A-24 14 006.
  • the diffusible, photographically active compounds that are released during development can also be, for example, a dye, a coupler, a hardening agent, a silver halide solvent, a fogging agent, a development accelerator, a developer compound, a bleaching inhibitor, a bleaching accelerator Trade mordants or a sensitizer.
  • Development inhibitors released are usually heterocyclic mercapto compounds or triazoles or benzotriazoles.
  • DIR compounds With regard to the essentially colorless coupling DIR compounds, reference is made, for example, to US Pat. No. 3,632,345, DE-A-23 59 295 and DE-A-25 40 959.
  • DIR compounds By using DIR compounds, a large number of photographic, the Effects influencing image quality are brought about. Such effects are, for example, the lowering of the gradation, the achievement of a finer grain of color, the improvement of the sharpness by the so-called edge effect and the improvement of the color purity and Color brilliance through so-called interimage effects.
  • the colorless coupling DIR compounds have the advantage over the color coupling DIR couplers that they can be used universally, so that the same connection can be used in all light-sensitive layers of a color photographic recording material regardless of the color to be produced.
  • DIR couplers on the other hand, can usually only be used in some of the light-sensitive layers because of the color they produce, unless the color secondary density attributable to them is tolerable in the other layers.
  • This advantage of the DIR compounds is offset by the disadvantage that they are generally less reactive than the DIR couplers. In practice, therefore, it has mostly been limited to using DIR couplers, if necessary two or more different ones in the same recording material, different DIR couplers being assigned to the differently spectrally sensitized layers in accordance with the color produced from the latter.
  • the photographically active compound be released rapidly from the coupler upon development, especially when the photographically active compound is to influence the further course of development. It is therefore very desirable if the couplers in question are very active are.
  • the structure of the coupler is also of particular importance. DIR couplers derived from ⁇ -heterocyclically substituted acetamides are known from JP-A-52 082 423. EP-A-0 287 833 describes quinazolone acetanilide DIR couplers which have extremely advantageous properties.
  • the aim of the invention is to achieve improvements in general solubility and in alkali solubility while maintaining the good properties of the quinazolone acetanilides (good level of activity, high stability, good accessibility).
  • DIR couplers are obtained whose pK values are 2.5 to 3 units lower than those of the comparable quinazolone acetanilides.
  • An alkyl radical represented by R 1 in formula I is straight-chain or branched, substituted or unsubstituted and contains 1-20 C atoms; Methyl, ethyl, butyl, hexyl, dodecyl and in particular -C4H9-t are examples of this.
  • An aryl radical represented by Formula 1 or contained in R1 is in particular phenyl or a for example phenyl group substituted with halogen, alkyl, alkoxy, acylamino or sulfamoyl, for example p-alkoxyphenyl, o-alkoxyphenyl, 2-chloro-5-acylaminophenyl, 2-hexadecyloxy-5- (N-methyl) sulfamoyl.
  • An acyl radical represented by R3 or R4 in formula I can be derived from an aliphatic or aromatic carboxylic acid or sulfonic acid, from a carbamic acid or sulfamic acid or from a carbonic acid semi-ester.
  • a link represented by Formula I by TIME is a group which, after being split off from the coupling point of the coupler when it is coupled with the oxidation product of the silver halide developing agent, is capable of releasing a photographically active residue bound to it, in the present case a triazole of the formula II, in a subsequent reaction .
  • the group TIME is also referred to as a time control element because, in the presence of such a group, the photographically active residue attached to it is released in many cases with a delay and can take effect.
  • Known time control elements are, for example the O atom being bound to the coupling point of the coupler and the C atom being bound to an N atom of a photographically active compound (for example DE-A-27 03 145), a group which, after being split off from the coupler, is subject to an intramolecular nucleophilic displacement reaction and thereby releases the photographically active compound (for example DE-A-28 55 697), a group in which, after separation from the coupler, electron transfer can take place along a conjugate system, whereby the photographically active compound is released (for example DE-A-31 05 026), or one in which X (for example -O-) is attached to the coupling point of the coupler and the C atom is bound to an atom of the photographically active compound and in which R is, for example, aryl (for example EP-A-0 127 063).
  • the group TIME can also be a group which can itself undergo a coupling reaction or a redox reaction after being split off from the coupling
  • An alkyl radical represented by R5, R6, R7, R8 or R9 in formula II can be straight-chain or branched and can contain up to 10 carbon atoms; Examples are methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, pentyl, hexyl, octyl.
  • the alkyl radicals can be substituted, for example by hydroxyl, alkoxy, alkylthio, acylamino or a cyclic imide group.
  • a cycloalkyl radical represented by R7 is, for example, cyclohexyl; an aralkyl radical (R7, R8) is, for example, benzyl; an alkenyl radical is, for example, allyl or 2-butenyl; an alkynyl radical is, for example, propynyl.
  • a cyclic amino group (R8, R9) is for example a piperidino or morpholino group.
  • a heterocyclic group represented by R5 or R6 is, for example, a furyl, thiazolyl or 1,2,4-triazolyl group.
  • Such a heterocyclic group can carry further substituents, e.g. Alkyl, alkoxy, alkylthio (-S-R7).
  • R5 is alkylthio and R6 is H, alkyl, alkylthio, aryl or a heterocyclic group, with the proviso that that at least one of the radicals R5 and R6 contains a group saponifiable in aqueous alkali at a distance of 2 to 4 atoms from the triazole ring, cf.
  • the DIR couplers according to the invention from the series of benzo-1,2,4-sulfondiazine-3-acetic anilides are excellently soluble in esters and alcohols, so that their incorporation into photographic layers presents no difficulties and means no restrictions in the choice of the coupler solvent.
  • the new DIR couplers couple largely independently of the pH of the developer.
  • a material built with them is less susceptible to fluctuations in the alkali content of the developer in terms of its sensitometric properties than a material built with conventional DIR couplers.
  • the coupling color of the chromogenic dyes formed from the new DIR couplers is in the range from orange to scarlet red, so it contributes comparatively little to the image information of the negative.
  • the advantageous properties of the couplers according to the invention are probably not least due to this that the triazole ring is apparently not only a good leaving group (leaving group), so that the couplers are very reactive, but apparently also has a certain tendency to adsorb on the silver halide grain and thereby influence the processes taking place during the development of the silver halide.
  • the groups determining the effectiveness of the photographically active compound apparently come into particularly favorable contact with the surface of the silver halide grain. It is therefore preferred according to the invention if the photographically active compound is one which influences the development of the silver halide, for example a development accelerator, a fogging agent, a bleaching accelerator or particularly preferably a development inhibitor. In the latter case in particular, it is further preferred if at least one of the radicals R5 and R6 is -S-R7 and at least one contains a saponifiable group.
  • the couplers according to the invention can be used in comparatively low concentrations. This also facilitates their use in layers of the color photographic recording material in which mainly purple or cyan dyes are produced without the respective color image being significantly impaired by an undesirable secondary density.
  • the starting material is the 2-aminobenzenesulfonamides, which in turn have either 2-amino or 2-acylaminobenzenesulfochlorides or are easily accessible by hydrogenation of 2-nitrobenzenesulfonamides.
  • Substituents can either be present in the 2-aminobenzenesulfonamide from the outset or introduced by electrophilic substitution.
  • the alkylthio group of 2-amino-5-alkylthiobenzenesulfonamides can be introduced by the sequence rhodanation, alkaline hydrolysis, alkylation, an acylamino group by nitration, reduction and acylation.
  • the ketone, anilide or acylhydrazide function is introduced via the second building block, which is derived from an acyl acetic ester or a malonic ester.
  • 3-pivaloylmethyl-benzo-1,2,4-sulfonediazines are e.g. preferably produced by base-catalyzed condensation of pivaloyl acetate with 2-aminobenzenesulfonamides, benzo-1,2,4-sulfondiazine-3-acetanilide either by reacting a maloniminoether anilide with a 2-aminobenzenesulfonamide or in two stages by reacting a maloniminoether ester with a 2-aminobenzenesulfonamide and subsequently formed benzo-1,2,4-sulfondiazine-3-ethyl acetate.
  • the 1,2,3-triazole which acts as an inhibitor, is also preferably introduced in a conventional manner by halogenation, preferably bromination, and subsequent nucleophilic substitution, preferably under aprotic conditions.
  • halogenation preferably bromination
  • nucleophilic substitution preferably under aprotic conditions.
  • the compounds of the present invention are suitable for use as DIR couplers in color photographic, in particular multilayer, recording materials. Since they are essentially yellow couplers, they are preferably used in or associated with a light-sensitive silver halide emulsion layer with a predominant sensitivity to the blue spectral range of visible light.
  • Couplers which give only a little color during development can be assigned to a blue-sensitive, a green-sensitive or a red-sensitive layer or also several of these layers without fear of color falsification.
  • the diffusion-resistant DIR couplers of the present invention can be introduced into the casting solution of the silver halide emulsion layers in a known manner or other colloid layers.
  • oil-soluble or hydrophobic couplers can preferably be added to a hydrophilic colloid solution from a solution in a suitable coupler solvent (oil former), optionally in the presence of a wetting or dispersing agent.
  • the hydrophilic casting solution can of course contain other conventional additives in addition to the binder.
  • the solution of the coupler need not be directly dispersed in the casting solution for the silver halide emulsion layer or other water permeable layer; Rather, it can also be advantageously first dispersed in an aqueous, non-photosensitive solution of a hydrophilic colloid, whereupon the mixture obtained, after removal of the low-boiling organic solvents used, may be mixed with the casting solution for the photosensitive silver halide emulsion layer or another water-permeable layer before application.
  • Suitable light-sensitive silver halide emulsions are emulsions of silver chloride, silver bromide or mixtures thereof, possibly with a low silver iodide content of up to 15 mol% in one of the commonly used hydrophilic binders.
  • Gelatin is preferably used as a binder for the photographic layers. However, this can be replaced in whole or in part by other natural or synthetic binders.
  • the emulsions can be chemically and spectrally sensitized in the usual way, and the emulsion layers Like other non-photosensitive layers, they can be cured in the usual way with known curing agents.
  • Color photographic recording materials usually contain at least one silver halide emulsion layer for the recording of light from the three spectral ranges red, green and blue.
  • the light-sensitive layers are spectrally sensitized in a known manner by means of suitable sensitizing dyes.
  • Blue-sensitive silver halide emulsion layers do not necessarily have to contain a spectral sensitizer, since in many cases the intrinsic sensitivity of the silver halide is sufficient for the recording of blue light.
  • Each of the light-sensitive layers mentioned can consist of a single layer or, in a known manner, for example in the case of the so-called double-layer arrangement, also comprise two or more silver halide emulsion partial layers (DE-C-1 121 470).
  • red-sensitive silver halide emulsion layers are arranged closer to the support than green-sensitive silver halide emulsion layers and these in turn are closer than blue-sensitive layers, with a non-light-sensitive yellow filter layer generally being located between green-sensitive layers and blue-sensitive layers.
  • a non-light-sensitive intermediate layer is usually arranged between layers of different spectral sensitivity Preventing the incorrect diffusion of developer oxidation products.
  • silver halide emulsion layers of the same spectral sensitivity can be directly adjacent to one another or be arranged such that there is a light-sensitive layer with a different spectral sensitivity between them (DE-A-1 958 709, DE-A-25 30 645, DE-A -26 22 922).
  • Color photographic recording materials for producing multicolored images usually contain, in spatial and spectral assignment to the silver halide emulsion layers of different spectral sensitivity, coloring compounds, here in particular color couplers, for producing the different partial color images cyan, purple and yellow.
  • Spatial assignment is understood to mean that the color coupler is in such a spatial relationship with the silver halide emulsion layer that an interaction between them is possible which permits an image-wise match between the silver image formed during development and the color image produced from the color coupler. This is usually achieved by the fact that the color coupler is contained in the silver halide emulsion layer itself or in an adjacent, possibly non-light-sensitive binder layer.
  • Spectral assignment means that the spectral sensitivity of each of the photosensitive Silver halide emulsion layers and the color of the partial color image generated from the spatially assigned color coupler have a specific relationship to one another, with each of the spectral sensitivities (red, green, blue) being assigned a different color of the relevant partial color image (for example blue-green, purple, yellow).
  • Each of the differently spectrally sensitized silver halide emulsion layers can be assigned one or more color couplers. If several silver halide emulsion layers of the same spectral sensitivity are present, each of them can contain a color coupler, which color couplers need not necessarily be identical. They should only result in at least approximately the same color during color development, normally a color that is complementary to the color of the light, for which the silver halide emulsion layers in question are predominantly sensitive.
  • red-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for producing the blue-green partial color image
  • green-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for producing the purple partial color image
  • blue-sensitive silver halide emulsion layers are used for generating the yellow partial color coupler for producing the partial color image.
  • other assignments are also known.
  • DIR, DAR or FAR couplers Since with DIR, DAR or FAR couplers the effectiveness of the residue released during coupling is mainly desired and the color-forming properties of these couplers are less important, such DIR, DAR or FAR couplers are also suitable which give essentially colorless products on coupling (DE-A-1 547 640).
  • the cleavable residue can also be a ballast residue, so that upon reaction with color developer oxidation products coupling products are obtained which are diffusible or at least have a weak or restricted mobility (US Pat. No. 4,420,556).
  • the color photographic recording material additionally contains at least one DIR coupler of the formula I, which coupler contains not only in the yellow layer but also in the purple layer and / or also in the blue-green layer and also in a non-light-sensitive layer adjacent to one of the layers mentioned can be.
  • the color photographic recording material of the present invention may contain further additives, for example antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties.
  • antioxidants for example antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties.
  • dye-stabilizing agents for influencing the mechanical and electrostatic properties.
  • UV-absorbing compounds are described for example in US-A-3 253 921, DE-C-2 036 719 and EP-A-0 057 160.
  • hydrophilic film-forming agents are suitable as protective colloid or binder for the layers of the recording material, e.g. Proteins, especially gelatin. Bumping aids and plasticizers can be used. Reference is made to the compounds specified in Research Disclosure No. 17,643 in Sections IX, XI and XII.
  • the layers of the photographic material can be hardened in the usual manner, for example with hardeners of the epoxy type, the heterocyclic ethylene imine and the acryloyl type. Furthermore, it is also possible to harden the layers in accordance with the process of DE-A-22 18 009 in order to obtain color photographic materials which are suitable for high-temperature processing. It is also possible to harden the photographic layers with hardeners of the diazine, triazine or 1,2-dihydroquinoline series or with hardeners of the vinyl sulfone type.
  • the color photographic recording material according to the invention is developed with a color developer compound.
  • All developer compounds which have the ability to react in the form of their oxidation product with color couplers to form azomethine dyes can be used as the color developer compound.
  • Suitable color developer compounds are aromatic compounds of the p-phenylenediamine type containing at least one primary amino group, for example N, N-dialkyl-p-phenylenediamines, such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methylsulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-ethyl-N-hydroxyethyl-3-methyl-p-phenylenediamine and 1- (N-ethyl-N-methoxyethyl) -3-methyl-p-phenylenediamine.
  • N, N-dialkyl-p-phenylenediamines such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methylsulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-eth
  • the material is usually bleached and fixed. Bleaching and fixing can be carried out separately or together will.
  • the usual compounds can be used as bleaching agents, for example Fe3+ salts and Fe3+ complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes, etc.
  • Particularly preferred are iron III complexes of aminopolycarboxylic acids, in particular, for example, ethylenediaminetetraacetic acid, N-hydroxyethylethylenediamine triacetic acid, alkyliminodicarboxylic acids and alkyliminodicarboxylic acids and Phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • a color photographic recording material for color negative color development was produced (layer structure 1 A - comparison) by applying the following layers in the order given to a transparent cellulose triacetate support.
  • the quantities given relate to 1 m2.
  • the corresponding amounts of AgNO3 are given. All silver halide emulsions were stabilized per 100 g of AgNO3 with 0.5 g of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene.
  • UV absorber UV-1 UV absorber UV-1

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (6)

  1. Matériau d'enregistrement pour la photographie en couleurs, comprenant au moins une couche photosensible d'émulsion à l'halogénure d'argent et un coupleur associé à cette couche, qui permet de libérer un composé photographiquement actif, caractérisé en ce que le coupleur répond à la formule générale (I) suivante :
    Figure imgb0103
     dans laquelle :
    R¹   est un groupe alkyle éventuellement substitué, par exemple un groupe tertio-C₄H₉, un groupe aryle éventuellement substitué, par exemple p-alkoxyphényle, -NH-aryle ou -NH-NH-R³ ;
    R²   représente H, un halogène, par exemple le chlore, un groupe alkoxy, alkylthio ou -NH-R⁴ ;
    R³ et R⁴   sont des groupes acyle ;
    X   est le reste d'un composé photographiquement actif comprenant un noyau monocyclique 1,2,3- ou 1,2,4-triazolique ;
    TIME   est un membre de jonction qui est libéré lors de la réaction du coupleur avec le produit d'oxydation d'un révélateur de couleur conjointement avec le reste X qui y est lié et qui libère quant à lui dans les conditions de développement le reste X comme composé photographiquement actif ;
    n   a la valeur 0 ou 1.
  2. Matériau d'enregistrement suivant la revendication 1, caractérisé en ce que le coupleur est un coupleur DIR (X est le reste d'un inhibiteur de développement).
  3. Matériau d'enregistrement suivant l'une des revendications 1 et 2, caractérisé en ce que X est un groupe de formule suivante :
    Figure imgb0104
     dans laquelle
    Z   est le reste nécessaire pour compléter un noyau de 1,2,3- ou de 1,2,4-triazole ;
    R⁵ et R⁶   représentent H, un groupe alkyle, aryle, un groupe hétérocyclique, alkoxy, -S-R⁷, amino, acylamino, un groupe ester d'acide carboxylique ou -CO-NR⁸R⁹ ;
    R⁷   est un groupe alkyle, cycloalkyle, aralkyle, alcényle, alcynyle ou aryle ;
    R⁸   est un groupe alkyle, aralkyle ou aryle ;
    R⁹   est de l'hydrogène, un reste tel que R⁸, ou bien R⁸ et R⁹ forment conjointement le reste nécessaire pour compléter un groupe amino cyclique.
  4. Matériau d'enregistrement suivant la revendication 2, caractérisé en ce que le coupleur DIR est contenu dans une couche d'émulsion à l'halogénure d'argent principalement sensible au bleu, et en ce qu'il contient au moins une autre couche d'émulsion à l'halogénure d'argent principalement sensible au vert ou principalement sensible au rouge.
  5. Matériau d'enregistrement suivant la revendication 2, caractérisé en ce que le coupleur DIR est contenu dans une couche d'émulsion à l'halogénure d'argent principalement sensible au rouge.
  6. Matériau d'enregistrement pour la photographie en couleurs comprenant au moins une couche unitaire d'émulsion à l'halogénure d'argent principalement sensible au bleu, à laquelle au moins un coupleur jaune est associé, une couche unitaire d'émulsion à l'halogénure d'argent principalement sensible au vert, à laquelle au moins un coupleur magenta est associé, et une couche unitaire d'émulsion à l'halogénure d'argent principalement sensible au rouge, à laquelle au moins un coupleur cyan est associé, caractérisé en ce qu'au moins une couche partielle de la couche unitaire d'émulsion à l'halogénure d'argent principalement sensible au vert ou de la couche unitaire d'émulsion à l'halogénure d'argent principalement sensible au rouge contient un coupleur DIR de formule I suivante :
    Figure imgb0105
     dans laquelle
    R¹   est un groupe alkyle éventuellement substitué, par exemple un groupe tertio-C₄H₉, un groupe aryle éventuellement substitué, par exemple p-alkoxyphényle, -NH-aryle ou -NH-NH-R³ ;
    R²   représente H, un halogène, par exemple le chlore, un groupe alkoxy, alkylthio ou -NH-R⁴ ;
    R³ et R⁴   sont des groupes acyle ;
    X   est le reste d'un composé photographiquement actif comprenant un noyau monocyclique 1,2,3- ou 1,2,4-triazolique ;
    TIME   est un membre de jonction qui est libéré lors de la réaction du coupleur avec le produit d'oxydation d'un révélateur de couleur conjointement avec le reste X qui y est lié et qui libère quant à lui dans les conditions de développement le reste X comme composé photographiquement actif ;
    n   a la valeur 0 ou 1.
EP90113825A 1989-08-01 1990-07-19 Matériau d'enregistrement pour photographie en couleurs à un coupleur libérant un composé photographiquement actif Expired - Lifetime EP0415056B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3925438 1989-08-01
DE3925438A DE3925438A1 (de) 1989-08-01 1989-08-01 Farbfotografisches aufzeichnungsmaterial mit einem kuppler, der eine fotografisch wirksame verbindung freisetzt

Publications (3)

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EP0415056A2 EP0415056A2 (fr) 1991-03-06
EP0415056A3 EP0415056A3 (en) 1991-03-20
EP0415056B1 true EP0415056B1 (fr) 1994-06-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP90113825A Expired - Lifetime EP0415056B1 (fr) 1989-08-01 1990-07-19 Matériau d'enregistrement pour photographie en couleurs à un coupleur libérant un composé photographiquement actif

Country Status (4)

Country Link
US (1) US5021330A (fr)
EP (1) EP0415056B1 (fr)
JP (1) JPH0369935A (fr)
DE (2) DE3925438A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4329418A1 (de) * 1993-09-01 1995-03-02 Agfa Gevaert Ag Gelbkuppler
US5759757A (en) * 1996-10-17 1998-06-02 Eastman Kodak Company Photographic elements containing development inhibitor releasing compounds
EP1246006A3 (fr) * 2001-03-29 2004-08-11 Fuji Photo Film Co., Ltd. Un coupleur formateur de colorant, produit photographique à l'halogénure d'argent sensible à la lumière, et un colorant azométhinique
JP4010824B2 (ja) * 2001-03-29 2007-11-21 富士フイルム株式会社 色素形成カプラー、ハロゲン化銀写真感光材料およびアゾメチン色素化合物
US6677110B2 (en) * 2001-03-30 2004-01-13 Fuji Photo Film Co., Ltd. Dye-forming coupler, silver halide photographic light-sensitive material, and azomethine dye compound
EP1341035B1 (fr) * 2002-03-01 2007-12-26 FUJIFILM Corporation Matériau photographique couleur à l' halogénure d' argent sensible à la lumière
US20040091825A1 (en) * 2002-03-01 2004-05-13 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
EP2168634B1 (fr) 2002-09-13 2012-12-19 Kao Corporation Composition de teinture capillaire comprenant un colorant polyméthinique
EP1403704A1 (fr) * 2002-09-27 2004-03-31 Fuji Photo Film Co., Ltd. Coupleur formateur de colorant et matériau photographique couleur à l' halogénure d' argent sensible à la lumière
ATE516278T1 (de) * 2004-09-27 2011-07-15 Fujifilm Corp Verfahren zur herstellung von amidverbindungen
WO2019151451A1 (fr) 2018-01-31 2019-08-08 富士フイルム株式会社 Composition de coloration, article coloré et colorant azoïque

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3841880A (en) * 1973-04-03 1974-10-15 Eastman Kodak Co Silver halide emulsion containing ketomethylene photographic color-forming couplers
DE3711418A1 (de) * 1987-04-04 1988-10-20 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit einem kuppler, der eine fotografisch wirksame verbindung freisetzt
JPH0228645A (ja) * 1988-04-07 1990-01-30 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料

Also Published As

Publication number Publication date
EP0415056A2 (fr) 1991-03-06
JPH0369935A (ja) 1991-03-26
US5021330A (en) 1991-06-04
DE59006122D1 (de) 1994-07-21
EP0415056A3 (en) 1991-03-20
DE3925438A1 (de) 1991-02-07

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