EP0401612B1 - Produit photographique pour la reproduction couleur avec un coupleur DIR - Google Patents

Produit photographique pour la reproduction couleur avec un coupleur DIR Download PDF

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Publication number
EP0401612B1
EP0401612B1 EP90109914A EP90109914A EP0401612B1 EP 0401612 B1 EP0401612 B1 EP 0401612B1 EP 90109914 A EP90109914 A EP 90109914A EP 90109914 A EP90109914 A EP 90109914A EP 0401612 B1 EP0401612 B1 EP 0401612B1
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EP
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Prior art keywords
group
coupler
color
couplers
silver halide
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EP90109914A
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German (de)
English (en)
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EP0401612A2 (fr
EP0401612A3 (fr
Inventor
Hans Dr. Vetter
Heinrich Dr. Odenwälder
Peter Dr. Bergthaller
Thomas Dr. Krüger
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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
    • 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 releases a development inhibitor during color development.
  • DIR development inhibitor releasing
  • the DIR compounds can be those which release an inhibitor residue react with the oxidation product of a color developer to form a dye (DIR coupler), or those that release the inhibitor without simultaneously forming a dye. The latter are also referred to as DIR compounds 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.
  • Development inhibitors released are usually heterocyclic mercapto compounds or derivatives of benzotriazole.
  • DIR couplers which release monocyclic triazoles as development inhibitors are described, for example, in DE-A-28 42 063 and EP-A-0 272 573.
  • 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.
  • Such effects are, for example, the lowering of the gradation, the achievement of a finer grain of color, the improvement of the sharpness through the so-called edge effect and the improvement of the color purity and the color brilliance through so-called interimage effects.
  • DIR Development-Inhibitor-Releasing
  • 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 part of the light-sensitive layers because of the color they produce, unless the color secondary density to be attributed 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.
  • the invention has for its object to provide a color photographic recording material, the coupler with a triazole ring bound to the coupling point contains from which the triazole ring is released as a highly effective silver halide development inhibitor during development.
  • EP-A-0 345 553 (prior art according to Art. 54 (3) EPC) relates to a color photographic recording material with at least one silver halide emulsion layer with grains which have a layered grain structure and with DIR couplers which can split off inhibitors of great diffusibility, Suitable inhibitors include monocyclic 1,2,3-triazoles, which can be substituted with a (C1-C6) alkylcarbonyloxy- (C1-C4) alkylthio radical or a radical of the formula -S- (CH2) n -COOR32 , wherein R32 is a substituted or unsubstituted straight-chain, branched or cyclic aliphatic radical or an optionally substituted aryl radical, and n is 1 to 4.
  • EP-A-0 272 573 relates to a color photographic recording material having a coupler which can release a monocyclic 1,2,3-triazole ring as a photographically active group, for example as a silver halide development initiator.
  • the monocyclic 1,2,3-triazole ring contains substituents R1, R2, which can be, for example, an alkyl group, an alkylthio group (-S-R3) or a carboxylic acid ester group.
  • R1, R2 can be, for example, an alkyl group, an alkylthio group (-S-R3) or a carboxylic acid ester group.
  • the remainder of a coupler represented by A in Formula I can be the remainder of a coupler which gives a cyan, purple or yellow dye upon color development, or the remainder of a coupler which gives essentially colorless or only slightly colored products. It is essentially known coupler remains. Teal couplers generally have a phenolic or naphtholic structure. Examples for this are described for example in US-A-2 369 929, US-A-2 772 162, EP-A-0 067 689, GB-A-519 208. Purple couplers are derived from 5-pyrazolone, indazolone or various pyrazoloazoles. Examples are described, for example, in DE-A-25 36 191, DE-A-27 03 589 and DE-A-28 13 522, GB-A-1 247 493.
  • Yellow couplers are derived, for example, from ⁇ -acylacetanilides such as pivaloylacetanilides or benzoylacetanilides or malondianilides. Examples are described, for example, in US-A-2,875,057, US-A-3,265,506, US-A-4,359,521 and DE-A-2,655,871. Couplers which provide essentially colorless products and at the same time are photographically effective Release of connection are described, for example, in US-A-3,632,345, US-A-3,928,041, US-A-3,958,993, US-A-3,961,959, US-A-4,052,213, US-A -4 088 491.
  • 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 radical bound to it, in the present case a monocyclic triazole radical, in a subsequent reaction.
  • the group TIME is also referred to as a timing control element, because in the presence of such a group a photographically effective residue attached to it, for example an inhibitor residue, is released in many cases with a delay and can become effective.
  • Timing elements are, for example, a group the O atom being bonded 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 cleavage from the coupler undergoes an intramolecular nucleophilic displacement reaction and thereby releases the photographically active compound (for example DE-A-28 55 697), a group in which electron transfer can take place along a conjugated system after being split off from the coupler, thereby releasing the photographically active compound (for example DE-A-31 05 026), or a group in which X (for example -O-) is bonded 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).
  • a photographically active compound for example DE-A-27 03 145
  • An alkylthio radical represented by R 1 or R 2 in formula I preferably contains 1 to 7 C atoms; it can also be substituted, e.g. with one of the saponifiable groups mentioned.
  • An alkyl radical represented by R2 or R3 in formula I preferably contains 1 to 7 C atoms; it can also be substituted, in particular by halogen, such as Cl or F, or by -CN.
  • a heterocyclic group (R2) is a furyl group.
  • An aryl group represented by R3 is, for example, phenyl, optionally substituted, e.g. with alkyl or halogen.
  • the groups -CO-OR3, -O-CO-OR3 and -O-CO-R3, which are contained in one of the substituents R1, R2 at a distance of 2 to 4 atoms from the triazole ring, are groups which in aqueous alkali are saponifiable.
  • the 2 to 4 atoms which define the distance between the group -CO-OR3, -O-CO-OR3 or -O-CO-R3 which can be saponified in aqueous alkali and the triazole ring can be C atoms and / or heteroatoms. They can in turn contain a group -CO-O-, which in this case cannot be saponified in aqueous alkali or to a much lesser extent, cf. INH-1.
  • the advantageous properties of the couplers according to the invention are presumably due, among other things, to the fact that the triazole ring is apparently not only a good leaving group (escape group), so that the couplers are very reactive, but apparently also has a certain tendency to adsorb on the silver halide grain and thereby the development to inhibit the silver halide.
  • Suitable inhibitors are the following:
  • DIR couplers are the following:
  • the imino ether hydrochloride obtained is added in portions to a solution of 45 g of 2-amino-4-chlorobenzamide heated to 85 ° C. in 300 ml of propionic acid. The mixture is then held at 100 ° C. for 1 hour, under reflux for 1 hour and is discharged onto 1,500 g of ice. After standing overnight, the residue is decanted and stirred with methanol. 65 g of the compound crystallize out overnight. After drying mp 184 ° C to 186 ° C.
  • 19.5 g (0.04 ml) of the compound obtained in stage 2 are brominated in 200 ml of acetic acid with 6.4 g of bromine in 20 ml of acetic acid at 25 ° C. After adding 5 g of sodium acetate, it is poured onto 400 ml of ice and until stirred to complete crystallization. It is suctioned off, digested with 100 ml of methanol and suctioned off again. After drying 17.5 g with decomposition melting point 160 ° C to 170 ° C.
  • the purification is carried out by column chromatography on silica gel with toluene-ethyl acetate 8: 2 as the eluent. 5 g of compound with a melting point of 125 ° C. to 131 ° C. (two isomers! Are obtained.
  • the compounds of the present invention are suitable for use as DIR couplers in color photographic, in particular multilayer, recording materials. If they are 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.
  • the couplers according to the invention namely a comparatively low development inhibition in the layer to which such a compound is assigned, in addition to a comparatively high development inhibition in adjacent unassigned layers, naturally comes into play particularly when it is a multi-layer color photographic recording material which, in addition to a predominantly blue-sensitive silver halide emulsion layer, contains further light-sensitive silver halide emulsion layers with predominant sensitivity for the green or red spectral range of the visible light.
  • the DIR couplers according to the invention are preferably assigned to a green-sensitive layer as purple couplers or to a red-sensitive layer as cyan-green couplers. 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 DIR couplers according to the invention can also be used as color couplers in comparatively small amounts in order to produce the desired effects, in particular the interimage effects.
  • the DIR couplers according to the invention can thus advantageously also be used as yellow couplers in purple layers as well as in blue-green layers. The same applies to the purple couplers and the cyan couplers.
  • the diffusion-resistant DIR couplers of the present invention can optionally be incorporated together with other couplers in a known manner into the casting solution of the silver halide emulsion layers 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 advantageously first be dispersed in an aqueous, non-photosensitive solution of a hydrophilic colloid whereupon the mixture obtained, optionally after removal of the low-boiling organic solvents used, is mixed with the casting solution for the light-sensitive 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 as well as other non-light-sensitive layers can be hardened in the usual way with known hardening 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 need a spectral sensitizer included, since in many cases the intrinsic sensitivity of the silver halide is sufficient for the recording of blue light.
  • Each of the said photosensitive layers can consist of a single layer or in a known manner, e.g. in 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 generally arranged between layers of different spectral sensitivity and can contain means for 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 the production of multicolored images usually contain spatial and spectral assignment to the silver halide emulsion layers Different spectral sensitivity, color-providing compounds, here especially color couplers, for the generation of the different partial color images teal, 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 is understood to mean that the spectral sensitivity of each of the light-sensitive silver halide emulsion layers and the color of the partial color image generated from the spatially assigned color coupler are in a specific relationship to one another, with each of the spectral sensitivities (red, green, blue) having a different color of the relevant partial color image (e.g. teal, purple, yellow) is assigned.
  • 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 may contain its 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.
  • the color couplers can be 4-equivalent couplers, but also 2-equivalent couplers.
  • the latter are derived from the 4-equivalent couplers in that they contain a substituent in the coupling point, which is split off during the coupling.
  • the 2-equivalent couplers include those that are colorless, as well as those that have an intense intrinsic color that disappears when the color is coupled or is replaced by the color of the image dye produced (mask coupler), and the white couplers that react with color developer oxidation products yield essentially colorless products.
  • the 2-equivalent couplers also include those couplers which contain a cleavable residue in the coupling site, which is released upon reaction with color developer oxidation products, either directly or after one or more further groups have been cleaved from the primarily cleaved residue (e.g. DE-A-27 03 145, DE-A-28 55 697, DE-A-31 05 026, DE-A-33 19 428), a certain desired photographic effectiveness unfolds, for example as a development inhibitor or accelerator.
  • Examples of such 2-equivalent couplers are the known DIR couplers as well as DAR or. FAR coupler.
  • DAR or FAR couplers Since in the DIR, DAR or FAR couplers the effectiveness of the residue released during the 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-15 47 640).
  • 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-methyl-sulfonamidoethyl) -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-methyl-sulfonamidoethyl) -3-methyl-p-phenylenediamine, 1- (N-eth
  • the material is usually bleached and fixed. Bleaching and fixing can be carried out separately or together.
  • 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 0.1 g of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene.
  • IIE bg ⁇ red - ⁇ w ⁇ w
  • IIE pp ⁇ green - ⁇ w ⁇ w

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Claims (1)

  1. Matériau d'enregistrement pour photographie en couleurs, comprenant au moins une couche d'émulsion photosensible à l'halogénure d'argent et un copulant DIR attribué à cette dernière, qui porte un radical triazolyle monocyclique séparable lié à son endroit de copulation, caractérisé en ce que le copulant répond à la formule ci-après : A- (TIME) n -Z
    Figure imgb0119
     dans laquelle
    A   représente le radical d'un copulant qui copule avec le produit d'oxydation d'un agent de développement de l'halogénure d'argent, dans les conditions du développement photographique, et libère en l'occurrence le radical de formule -(TIME) n -Z;
    Figure imgb0120
    TIME   représente un chaînon qui est libéré lors de la réaction du copulant avec le produit d'oxydation d'un agent de développement de l'halogénure d'argent, conjointement avec le radical Z (un noyau triazole) qui y est lié et qui libère, à son tour, de manière retardée, le radical Z dans les conditions de développement;
    n   est égal à 0 ou 1;
    Z   représente un radical triazole répondant à une des formules
    Figure imgb0121
    R¹   représente un radical alkylthio;
    R²   représente H, un groupe alkyle, un groupe alkylthio, un groupe aryle ou un groupe hétérocyclique, au moins un des radicaux R¹ et R² contenant, à une distance de 2 à 4 atomes du noyau triazole, un groupe -CO-OR³, -O-CO-OR³ ou -O-CO-R³, saponifiable dans un alcali aqueux;
    R³   représente un groupe alkyle, un groupe cycloalkyle ou un groupe aryle,
    avec cette mesure que, au cas où le noyau triazole est un noyau 1,2,3-triazole, un radical alkylthio représenté par R¹ n'est pas un radical alkyl (en C₁-C₄) carbonyloxyalkyl (en C₁-C₄) thio ou un radical de formule -S-(CH₂)p-COOR⁴ où R⁴ représente un radical aliphatique à chaîne droite, à chaîne ramifiée ou cyclique, substitué ou non substitué, ou encore un radical aryle éventuellement substitué, et p représente un nombre de 1 à 4.
EP90109914A 1989-06-06 1990-05-24 Produit photographique pour la reproduction couleur avec un coupleur DIR Expired - Lifetime EP0401612B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3918394A DE3918394A1 (de) 1989-06-06 1989-06-06 Farbfotografisches aufzeichnungsmaterial mit einem dir-kuppler
DE3918394 1989-06-06

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EP0401612A2 EP0401612A2 (fr) 1990-12-12
EP0401612A3 EP0401612A3 (fr) 1991-06-05
EP0401612B1 true EP0401612B1 (fr) 1995-06-21

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US5200306A (en) * 1986-12-24 1993-04-06 Agfa Gevaert Aktiengesellschaft Color photographic recording material containing a coupler which releases a photographically active compound
JP2684256B2 (ja) * 1991-03-19 1997-12-03 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
JPH0553264A (ja) * 1991-08-23 1993-03-05 Konica Corp ハロゲン化銀カラー写真感光材料
US5378593A (en) * 1992-05-22 1995-01-03 Eastman Kodak Company Color photographic materials and methods containing DIR or DIAR couplers and carbonamide coupler solvents
EP0572894B1 (fr) * 1992-06-03 1999-08-04 Agfa-Gevaert AG Produit photographique d'enregistrement en couleur avec un coupleur DIR cyan
DE4218308A1 (de) * 1992-06-03 1993-12-09 Agfa Gevaert Ag Verfahren zur Herstellung von naphtholischen 2-Äquivalentcyankupplern
US5385815A (en) 1992-07-01 1995-01-31 Eastman Kodak Company Photographic elements containing loaded ultraviolet absorbing polymer latex
JPH07110558A (ja) * 1993-10-12 1995-04-25 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH08101477A (ja) 1994-08-01 1996-04-16 Eastman Kodak Co 水性写真用コーティング組成物
EP0747763B1 (fr) * 1995-06-06 1999-10-13 Imation Corp. Eléments photographiques couleur à l'halogénure d'argent sensible à la lumière présentant une qualité d'image améliorée
US5759757A (en) * 1996-10-17 1998-06-02 Eastman Kodak Company Photographic elements containing development inhibitor releasing compounds
US5821043A (en) * 1996-12-30 1998-10-13 Eastman Kodak Company 1,2,4-triazole-releasing pyrazolone DIR couplers
US6027867A (en) * 1997-06-25 2000-02-22 Konica Corporation Silver halide color photographic light sensitive material
US6004737A (en) * 1997-07-18 1999-12-21 Eastman Kodak Company Photographic element containing a yellow DIR coupler

Citations (1)

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EP0287833A1 (fr) * 1987-04-04 1988-10-26 Agfa-Gevaert AG Matériau d'enregistrement pour la photographie en couleurs avec un agent de copulation libérant un composé photographiquement actif

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US4049458A (en) * 1974-06-05 1977-09-20 Agfa-Gevaert, A.G. Photographic silver halide material containing 2-equivalent yellow couplers
CA1099559A (fr) * 1977-09-29 1981-04-21 Mario Fryberg Derives de 1,2,4-triazole a substitution par un groupement thio ou seleno en position 5
DE3626219A1 (de) * 1986-08-02 1988-02-04 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit einem gelb-dir-kuppler
DE3630564A1 (de) * 1986-09-09 1988-03-10 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit einem gelb-dir-kuppler
DE3636824A1 (de) * 1986-10-29 1988-05-05 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit einem gelb-dir-kuppler
EP0272573B1 (fr) * 1986-12-24 1990-06-06 Agfa-Gevaert AG Matériau de reproduction photographique couleur avec un coupleur libérant un composé photographiquement actif
DE3819469A1 (de) * 1988-06-08 1989-12-14 Agfa Gevaert Ag Fotografisches aufzeichnungsmaterial

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0287833A1 (fr) * 1987-04-04 1988-10-26 Agfa-Gevaert AG Matériau d'enregistrement pour la photographie en couleurs avec un agent de copulation libérant un composé photographiquement actif

Also Published As

Publication number Publication date
EP0401612A2 (fr) 1990-12-12
JPH0318844A (ja) 1991-01-28
US5021331A (en) 1991-06-04
DE59009272D1 (de) 1995-07-27
DE3918394A1 (de) 1990-12-13
EP0401612A3 (fr) 1991-06-05

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