EP0437818B1 - Matériau d'enregistrement pour la photographie en couleurs - Google Patents

Matériau d'enregistrement pour la photographie en couleurs Download PDF

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EP0437818B1
EP0437818B1 EP90125261A EP90125261A EP0437818B1 EP 0437818 B1 EP0437818 B1 EP 0437818B1 EP 90125261 A EP90125261 A EP 90125261A EP 90125261 A EP90125261 A EP 90125261A EP 0437818 B1 EP0437818 B1 EP 0437818B1
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Prior art keywords
compounds
color
alkyl
couplers
layer
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EP90125261A
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German (de)
English (en)
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EP0437818A3 (en
EP0437818A2 (fr
Inventor
Helmut Dr. Mäder
Friedrich-Wilhelm Dr. Kunitz
Werner Dr. Liebe
Fritz Dr. Nittel
Dieter Rockser
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Agfa Gevaert AG
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Agfa Gevaert AG
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    • 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
    • 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
    • G03C7/392—Additives
    • G03C7/396—Macromolecular additives

Definitions

  • the invention relates to a color photographic recording material having at least one silver halide emulsion layer and a diffusion-resistant ⁇ -acylacetanilide yellow coupler, the anilide group of which is substituted by an N-acylsulfamoyl group which is dissolved in a specific organic solvent.
  • the coupling speed of the color couplers with the oxidation product of the color developer should be as high as possible and the highest possible color density should be achieved.
  • the color couplers and the dyes obtained from them must be sufficiently stable to light, elevated temperature and moisture. This applies to both fresh material and processed material. For example, the remaining coupler still present in the image whites of the processed material must not turn yellow.
  • the dyes should be sufficiently resistant to gaseous reducing or oxidizing agents. They must also be firmly anchored in the image layer and should separate as fine a grain as possible during chromogenic development.
  • the dyes resulting from the color couplers in the chromogenic development must have a favorable absorption curve with a maximum that corresponds to the color of the desired partial image and the lowest possible secondary absorptions.
  • An aliphatic radical represented by Y is preferably a tert-alkyl radical, in particular tert-butyl.
  • a cycloaliphatic radical represented by Y is, for example, a cyclohexyl, norbornyl or adamantyl radical.
  • a group represented by X on color coupling is preferably a cyclic group attached via an oxygen atom or via a nitrogen atom, in particular a ring nitrogen atom, e.g. an optionally substituted 5- or 6-membered heterocyclic ring linked via a ring nitrogen atom.
  • Such cleavable groups also known as escape groups, usually give the coupler the behavior of a 2-equivalent coupler, i.e. the coupler only requires half as much developable silver halide for color coupling as the corresponding 4-equivalent coupler, in which X denotes a hydrogen atom.
  • the refugee groups also include those that are photographically effective and, for example, inhibit or accelerate development.
  • the couplers are known from US-A-4 617 256.
  • the couplers of the formula (I) have the disadvantage that the dyes produced from them with the customary color developers of the p-phenylenediamine series have unsatisfactory lightfastness.
  • these couplers are sparingly soluble in common solvents such as tricresyl phosphate, which leads to crystalline precipitations and thus to casting errors (so-called point errors).
  • the object of the invention was therefore to overcome these disadvantages without losing the positive properties of this coupler class.
  • the invention therefore relates to a color photographic recording material having at least one silver halide emulsion layer and a diffusion-resistant coupler of the formula (I), characterized in that liquid compounds containing carboxylic ester groups and having a molecular weight of at least 350 are used as oil formers for the color couplers of the formula (I), and the photosensitive layers of the material comprise silver halide emulsions with at least 95 mol% AgCl.
  • the oil formers are preferably mono- or diesters of aliphatic or aromatic dicarboxylic acids and aliphatic or araliphatic alcohols or polyesters of aliphatic or aromatic dicarboxylic acids and aliphatic diols.
  • the molecular weight preferably does not exceed 1200.
  • Suitable oil formers are e.g. Dinonyl adipate, dinonyl phthalate, octadecylene succinic acid monobenzyl ester and polymers of adipic acid or phthalic acid and diols, e.g. Butanediol and / or pentanediol. Up to 30% by weight of the oil binder can be replaced by other oil formers, e.g. Tricresyl phosphate or polyalkylene glycols can be replaced. However, the yellow couplers are preferably only dissolved in the oil former according to the invention.
  • the diffusion-resistant yellow couplers of the present invention are incorporated in the oil formers according to the invention, if appropriate in the presence of a wetting or dispersing agent, in a known manner into the casting solution of the silver halide emulsion layers or other colloid layers.
  • the hydrophilic casting solution can of course contain other conventional additives in addition to the binder.
  • the color coupler solution does not need to be directly dispersed in the casting solution for the silver halide emulsion layer or other water permeable layer; Rather, it may also be advantageously first dispersed in an aqueous non-photosensitive solution of a hydrophilic colloid, whereupon the mixture obtained is mixed with the coating solution for the photosensitive silver halide emulsion layer or another water-permeable layer before application.
  • 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.
  • the light-sensitive layer to which the yellow coupler according to the invention is assigned is in particular blue-sensitized.
  • the color photographic material which preferably contains a reflective support, also contains at least one green-sensitive layer to which a magenta coupler is assigned and at least one red-sensitive layer to which a cyan coupler is assigned, and optionally intermediate and protective layers.
  • 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 and thereby 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, e.g. as a development inhibitor or accelerator.
  • Examples of such 2-equivalent couplers are the known DIR couplers as well as DAR or. FAR coupler.
  • Color couplers for producing the blue-green partial color image are usually couplers of the phenol or ⁇ -naphthol type.
  • Color coupler for generating the purple partial color image are usually couplers of the 5-pyrazolone, indazolone or pyrazoloazole type.
  • the blue-green and purple couplers can be incorporated in the same way and with the same oil formers as the yellow couplers.
  • Suitable oil formers for magenta and cyan couplers are, in addition, other alkyl phthalates, phosphonic esters, phosphoric esters, citric acid esters, benzoic acid esters, amides, fatty acid esters, trimesic acid esters, alcohols, phenols, aniline derivatives and hydrocarbons.
  • oil formers are dibutylphthalate, dicyclohexylphthalate, di-2-ethylhexylphthalate, decylphthalate, triphenylphosphate, tricresylphosphate, 2-ethylhexyldiphenylphosphate, tricyclohexylphosphate, tri-2-ethylhexylphosphate, tridecoxyphosphate, 2-ethylhexylphosphate, tridecoxyphosphate, 2-ethylhexylphosphate, , 2-ethylhexyl p-hydroxybenzoate, diethyldodecanamide, N-tetradecylpyrrolidone, isostearyl alcohol, 2,4-di-tert.-amylphenol, dioctylacelate, glycerol tributyrate, isostearyl lactate, trioctyl citrate, N, N-doxy-5-butyl-2-butyl
  • the non-light-sensitive intermediate layers which are generally arranged between layers of different spectral sensitivity, can contain agents which prevent undesired diffusion of developer oxidation products prevent from one photosensitive to another photosensitive layer with different spectral sensitization.
  • Suitable agents which are also called scavengers or EOP-catchers, are described in Research Disclosure 17 643 (Dec. 1978), Chapter VII, 17 842/1979, pages 94-97 and 18.716 / 1979, page 650 and in EP-A- 69,070, 98,072, 124,877, 125,522 and in US-A-463,226.
  • the silver halide present as a light-sensitive component in the photographic material can be predominantly compact crystals, which are e.g. are regular cubic or octahedral or can have transitional forms.
  • platelet-shaped crystals can preferably also be present, the average ratio of diameter to thickness of which is preferably at least 5: 1, the diameter of a grain being defined as the diameter of a circle with a circle content corresponding to the projected area of the grain.
  • the layers can also have tabular silver halide crystals in which the ratio of diameter to thickness is substantially greater than 5: 1, e.g. 12: 1 to 30: 1.
  • the silver halide grains can also have a multi-layered grain structure, in the simplest case with an inner and an outer grain area (core / shell), the halide composition and / or other modifications, such as doping of the individual grain areas, being different.
  • the middle The grain size of the emulsions is preferably between 0.2 ⁇ m and 2.0 ⁇ m, the grain size distribution can be either homodisperse or heterodisperse. Homodisperse grain size distribution means that 95% of the grains do not deviate from the mean grain size by more than ⁇ 30%.
  • the emulsions can also contain organic silver salts, for example silver benzotriazolate or silver behenate.
  • Two or more kinds of silver halide emulsions, which are prepared separately, can be used as a mixture.
  • the photographic emulsions can be prepared using various methods (e.g. P. Glafkides, Chimie et Physique Photographique, Paul Montel, Paris (1967), GF Duffin, Photographic Emulsion Chemistry, The Focal Press, London (1966), VL Zelikman et al, Making and Coating Photographic Emulsion, The Focal Press, London (1966) from soluble silver salts and soluble halides.
  • various methods e.g. P. Glafkides, Chimie et Physique Photographique, Paul Montel, Paris (1967), GF Duffin, Photographic Emulsion Chemistry, The Focal Press, London (1966), VL Zelikman et al, Making and Coating Photographic Emulsion, The Focal Press, London (1966) from soluble silver salts and soluble halides.
  • Salts or complexes of metals such as Cd, Zn, Pb, Tl, Bi, Ir, Rh, Fe may also be present during the precipitation and / or physical ripening of the silver halide grains.
  • the precipitation can also be carried out in the presence of sensitizing dyes.
  • Complexing agents and / or dyes can be rendered ineffective at any time, for example by changing the pH or by an oxidative treatment.
  • the soluble salts are removed from the emulsion, e.g. by pasta and washing, by flakes and washing, by ultrafiltration or by ion exchangers.
  • the silver halide emulsion is generally subjected to chemical sensitization under defined conditions - pH, pAg, temperature, gelatin, silver halide and sensitizer concentration - until the optimum sensitivity and fog are reached.
  • the procedure is e.g. described by H. Frieser "The basics of photographic processes with silver halides" page 675-734, Akademische Verlagsgesellschaft (1968).
  • Chemical sensitization can be carried out with the addition of compounds of sulfur, selenium, tellurium and / or compounds of the metals of subgroup VIII of the periodic table (for example gold, platinum, palladium, iridium) Nitrogen compounds (e.g. imidazoles, azaindenes) or spectral sensitizers (described, for example, by F. Hamer "The Cyanine Dyes and Related Compounds", 1964, or Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, vol. 18, pp. 431 ff. and Research Disclosure No. 17643, Section III).
  • Nitrogen compounds e.g. imidazoles, azaindenes
  • spectral sensitizers described, for example, by F. Hamer "The Cyanine Dyes and Related Compounds", 1964, or Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, vol. 18, pp. 431 ff. and Research Disclosure No. 17643, Section III).
  • a reduction sensitization with the addition of reducing agents can be carried out by hydrogen, by low pAg (eg less than 5) and / or high pH (eg above 8).
  • the photographic emulsions may contain compounds to prevent fogging or to stabilize the photographic function during production, storage or photographic processing.
  • Azaindenes are particularly suitable, preferably tetra- and penta-azaindenes, in particular those which are substituted by hydroxyl or amino groups. Such connections are for example from Birr, Z. Wiss. Phot. 47 (1952), pp. 2-58. Furthermore, salts of metals such as mercury or cadmium, aromatic sulfonic or sulfinic acids such as benzenesulfinic acid, or nitrogen-containing heterocycles such as nitrobenzimidazole, nitroindazole, optionally substituted benzotriazoles or benzothiazolium salts can be used as antifoggants.
  • metals such as mercury or cadmium, aromatic sulfonic or sulfinic acids such as benzenesulfinic acid, or nitrogen-containing heterocycles such as nitrobenzimidazole, nitroindazole, optionally substituted benzotriazoles or benzothiazolium salts can be used as antifoggants.
  • Heterocycles containing mercapto groups for example mercaptobenzthiazoles, mercaptobenzimidazoles, mercaptotetrazoles, mercaptothiadiazoles, mercaptopyrimidines, are particularly suitable, these mercaptoazoles also being able to contain a water-solubilizing group, for example a carboxyl group or sulfo group.
  • mercaptobenzthiazoles for example mercaptobenzthiazoles, mercaptobenzimidazoles, mercaptotetrazoles, mercaptothiadiazoles, mercaptopyrimidines
  • these mercaptoazoles also being able to contain a water-solubilizing group, for example a carboxyl group or sulfo group.
  • a water-solubilizing group for example a carboxyl group or sulfo group.
  • the stabilizers can be added to the silver halide emulsions before, during or after their ripening.
  • the compounds can also be added to other photographic layers which are assigned to a halogen silver layer.
  • the photographic emulsion layers or other hydrophilic colloid layers of the light-sensitive material produced according to the invention can contain surface-active agents for various purposes, such as coating aids, to prevent electrical charging, to improve the sliding properties, to emulsify the dispersion, to prevent adhesion and to improve the photographic characteristics (eg acceleration of development, high contrast, sensitization etc.).
  • non-ionic surfactants for example alkylene oxide compounds, glycerol compounds or glycidol compounds
  • cationic surfactants for example higher alkylamines, quaternary ammonium salts, pyridine compounds and other heterocyclic compounds
  • sulfonium compounds or phosphonium compounds anionic surfactants containing an acid group, for example carboxylic acid, sulfonic acid, a phosphoric acid, sulfuric acid ester or phosphoric acid ester group
  • ampholytic surfactants for example amino acid and aminosulfonic acid compounds and sulfur or phosphoric acid esters of an amino alcohol.
  • the photographic material can also contain UV light-absorbing compounds, whiteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve dye, coupler and white stabilization and to reduce the color fog, plasticizers (latices), Contain biocides and others.
  • Examples are aryl-substituted benzotriazole compounds (US-A-3 533 794), 4-thiazolidone compounds (US-A-3 314 794 and 3 352 681), benzophenone compounds (JP-A-2784/71), cinnamic acid ester compounds (US-A-3 705 805 and 3,707,375), butadiene compounds (US-A-4,045,229) or benzoxazole compounds (US-A-3,700,455).
  • Certain layers of binder in particular the layer furthest away from the carrier, but also occasionally intermediate layers, especially if they represent the layer furthest away from the carrier during production, can contain photographically inert particles of an inorganic or organic nature, e.g. as matting agents or as spacers ( DE-A-33 31 542, DE-A-34 24 893, Research Disclosure 17 643, (Dec. 1978), Chapter XVI).
  • photographically inert particles of an inorganic or organic nature e.g. as matting agents or as spacers ( DE-A-33 31 542, DE-A-34 24 893, Research Disclosure 17 643, (Dec. 1978), Chapter XVI).
  • the average particle diameter of the spacers is in particular in the range from 0.2 to 10 ⁇ m.
  • the spacers are water-insoluble and can be alkali-insoluble or alkali-soluble, the alkali-soluble ones generally being removed from the photographic material in the alkaline development bath.
  • suitable polymers are polymethyl methacrylate, copolymers of acrylic acid and methyl methacrylate and hydroxypropyl methyl cellulose hexahydrophthalate.
  • the layers of the photographic material can be hardened with the usual hardening agents.
  • Suitable curing agents include formaldehyde, glutaraldehyde and similar aldehyde compounds, diacetyl, cyclopentadione and similar ketone compounds, bis (2-chloroethylurea), 2-hydroxy-4,6-dichloro-1,3,5-triazine and other compounds, the reactive halogen contain (US-A-3 288 775, US-A-2 732 303, GB-A-974 723 and GB-A-1 167 207) divinyl sulfone compounds, 5-acetyl-1,3-diacryloylhexahydro-1,3,5 triazine and other compounds containing a reactive olefin bond (US-A-3 635 718, US-A-3 232 763 and GB-A-994 869); N-hydroxymethylphthalimide and other N-methylol compounds (US-A-2 732 316 and US
  • the hardening can be effected in a known manner by adding the hardening agent to the casting solution for the layer to be hardened, or by overlaying the layer to be hardened with a layer which contains a diffusible hardening agent.
  • Immediate hardeners are understood to mean compounds which crosslink suitable binders in such a way that the hardening is completed immediately after casting, at the latest after 24 hours, preferably after 8 hours at the latest, so that no further change in the sensitometry caused by the crosslinking reaction and the swelling of the layer structure occurs .
  • Swelling is understood to mean the difference between the wet film thickness and the dry film thickness during the aqueous processing of the film (Photogr. Sci., Eng. 8 (1964), 275; Photogr. Sci. Eng. (1972), 449).
  • hardening agents that react very quickly with gelatin are e.g. to carbamoylpyridinium salts, which are able to react with free carboxyl groups of the gelatin, so that the latter react with free amino groups of the gelatin to form peptide bonds and crosslink the gelatin.
  • Color photographic negative materials are usually processed by developing, bleaching, fixing and washing or by developing, bleaching, fixing and stabilizing without subsequent washing, whereby bleaching and fixing can be combined into one processing step.
  • All developer compounds which have the ability to react in the form of their oxidation product with color couplers to form azomethine or indophenol 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-methanesulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-ethyl-N-hydroxyethyl) -3-methyl-p-phenylenediamine and 1- (N-ethyl-N-methoxyethyl) -3-methyl-p-phenylenediamine.
  • Other useful color developers are described, for example, in J. Amer. Chem. Soc. 73 , 3106 (1951) and G. Haist, Modern Photographic Processing, 1979, John Wiley and Sons, New York, page 545 ff.
  • bleaching agents e.g. Fe (III) salts and Fe (III) complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes can be used.
  • Iron (III) complexes of aminopolycarboxylic acids are particularly preferred, especially e.g. of ethylenediaminetetraacetic acid, propylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, nitrilotriacetic acid, iminodiacetic acid, N-hydroxyethylethylenediaminetriacetic acid, alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulfates and peroxides e.g. Hydrogen peroxide.
  • the bleach-fixing bath or fixing bath is usually followed by washing, which is designed as countercurrent washing or consists of several tanks with their own water supply.
  • the washing can be completely replaced by a stabilizing bath, which is usually carried out in countercurrent.
  • this stabilizing bath also acts as a final bath.
  • a protective layer of 0.9 g / m2 of gelatin and 0.3 g / m2 of the hardening agent of the formula was applied to this layer applied and the samples dried.
  • the samples were exposed behind a grayscale wedge, developed in the color developer specified below, then fixed to bleach, washed and dried.
  • Coupler V1 has the formula:
  • TKP is comparable to the oil formers according to the invention with regard to the sensitometric properties, but shows an increased number of pouring errors compared to the samples according to the invention, which is shown in Example 2.
  • Samples 4 to 11 are according to the invention.

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

Claims (2)

  1. Matériau ou support pour enregistrement photographique en couleurs, comportant au moins une couche d'émulsion d'halogénure d'argent photosensible et un coupleur pour jaune, résistant à la diffusion et associé à cette couche, ce coupleur ayant pour formule
    Figure imgb0035
     dans laquelle
    Y   représente un reste aliphatique ou cycloaliphatique,
    X   représente un atome d'hydrogène ou un groupe scindable lors du couplage chromogène,
    R¹   représente un reste alkyle ayant 1 à 20 atomes de carbone,
    R²   représente un reste alkyle ayant 1 à 20 atomes de carbone,
    les restes alkyles R¹ et R² présentant ensemble au moins 12 atomes de carbone, matériau caractérisé en ce que l'on utilise comme produit oléfiant pour le coupleur chromogène de formule (I) des composés liquides contenant des groupes esters d'acide carboxylique et présentant un poids moléculaire valant au moins 350, et en ce que les couches photosensibles du matériau ou du support présentent des émulsions d'halogénure d'argent comportant au moins 95 mol% de chlorure d'argent.
  2. Matériau ou support pour enregistrement de photographies en couleurs selon la revendication 1, dans le cas duquel le coupleur pour jaune répond à la formule
    Figure imgb0036
     dans laquelle
    R³   représente un reste alkyle en C₁₁-C₂₀,
    R⁴   représente un reste alkyle en C₁-C₄, et
    R⁵   représente un reste phényle éventuellement substitué par de l'halogène ou par un reste alkyle en C₁-C₄.
EP90125261A 1990-01-13 1990-12-21 Matériau d'enregistrement pour la photographie en couleurs Expired - Lifetime EP0437818B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4000844 1990-01-13
DE4000844A DE4000844A1 (de) 1990-01-13 1990-01-13 Farbfotografisches aufzeichnungsmaterial

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EP0437818A2 EP0437818A2 (fr) 1991-07-24
EP0437818A3 EP0437818A3 (en) 1991-10-09
EP0437818B1 true EP0437818B1 (fr) 1995-09-06

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DE4322056A1 (de) * 1993-07-02 1995-01-12 Agfa Gevaert Ag Farbfotografisches Material
US5605785A (en) * 1995-03-28 1997-02-25 Eastman Kodak Company Annealing processes for nanocrystallization of amorphous dispersions

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Publication number Priority date Publication date Assignee Title
EP0364807A2 (fr) * 1988-10-15 1990-04-25 Agfa-Gevaert AG Matériau de reproduction photographique couleur

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DE3441525A1 (de) * 1984-11-14 1986-05-15 Agfa-Gevaert Ag, 5090 Leverkusen Farbfotografisches farbkupplerhaltiges aufzeichnungsmaterial

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EP0364807A2 (fr) * 1988-10-15 1990-04-25 Agfa-Gevaert AG Matériau de reproduction photographique couleur

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EP0437818A3 (en) 1991-10-09
DE59009631D1 (de) 1995-10-12
EP0437818A2 (fr) 1991-07-24

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