EP0563638B1 - Matériau photographique d'enregistrement - Google Patents

Matériau photographique d'enregistrement Download PDF

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Publication number
EP0563638B1
EP0563638B1 EP93103858A EP93103858A EP0563638B1 EP 0563638 B1 EP0563638 B1 EP 0563638B1 EP 93103858 A EP93103858 A EP 93103858A EP 93103858 A EP93103858 A EP 93103858A EP 0563638 B1 EP0563638 B1 EP 0563638B1
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EP
European Patent Office
Prior art keywords
layer
alkyl
aryl
color
coupler
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Expired - Lifetime
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EP93103858A
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German (de)
English (en)
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EP0563638A1 (fr
Inventor
Jörg Dr. Hagemann
Günter Dr. Helling
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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
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39232—Organic compounds with an oxygen-containing function
    • 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
    • G03C7/3003—Materials characterised by the use of combinations of photographic compounds known as such, or by a particular location in the photographic element
    • G03C7/3005—Combinations of couplers and photographic additives
    • G03C7/3008—Combinations of couplers having the coupling site in rings of cyclic compounds and photographic additives
    • G03C7/301—Combinations of couplers having the coupling site in pyrazoloazole rings and photographic additives

Definitions

  • the invention relates to a photographic recording material with at least one silver halide emulsion layer, the new type of light stabilizer for those at Chromogenic development produced purple azomethine dyes of pyrazoloazole type contains.
  • Color developer - developed which is in accordance oxidation product resulting from the silver image of the developer substances with the color coupler with formation of a dye image reacts.
  • a color developer are usually aromatic, containing primary amino groups Compounds, especially those of the p-phenylenediamine type, used.
  • Light stabilizing agents are essentially suitable phenolic compounds, especially derivatives of Hydroquinones, either added to the couplers or linked in the form of substituents with the coupler molecules (DE-B-1 547 803, DE-A-26 17 826, DE-A-29 52 511, JP-N 53 070 822, JP-N 54 070 830, JP-N 54 073 032).
  • the known light stabilizers are sufficient but not in all respects the one made to them Conditions.
  • the invention has for its object for photographic Novel light stabilizers specify, especially those for improvement the light stability of those from magenta couplers, of the pyrazoloazole type produced purple image dyes are suitable.
  • a radical which can be split off under alkaline conditions and is represented by R 1 is, for example, an acyl radical which is derived from aliphatic or aromatic carboxylic acids;
  • Examples of radicals which can be split off under alkaline conditions are acetyl, dichloroacetyl, alkoxycarbonyl and pyruvoyl.
  • An alkyl radical represented by R 2 to R 6 preferably contains 1 to 4 carbon atoms, examples are methyl, ethyl, propyl, isopropyl, butyl, t-butyl.
  • An aryl radical represented by R 2 to R 6 contains 6 to 10 C atoms; Examples are phenyl and naphthyl.
  • the alkyl or aryl radicals can be further substituted, for example with halogen or alkyl.
  • An alkoxy radical represented by R 2 to R 6 can contain 1 to 18 carbon atoms.
  • the acyl radical in an acylamino radical represented by R 2 to R 6 is derived from aliphatic or aromatic carboxylic or sulfonic acids.
  • the compounds of the invention can be prepared in a simple manner by reacting amines of the formula II with monomeric mono-, di- or polyisocyanates.
  • isocyanates for the preparation of compounds of the formula I are all aromatic and aliphatic Isocyanates with 1 to 4 isocyanate groups such as e.g. 3-chlorophenyl isocyanate, Phenyl isocyanate, 1,3-phenylene diisocyanate, 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, the isomers of tolylene diisocyanate, optionally a mixture, 2,4-bis (4-isocyanatobenzyl) -1-isocyanato-benzene, Tris (4-isocyanatophenyl) methane, 2-ethyl-1,2,3-tris (3-isocyanato-4-methyl-anilinocarbonyloxy) propane, Tetrakis (5-isocyanatopentylcarbonyloxymethyl) methane, preferably the aliphatic Mono- and diisocyanates such as dodecyl iso
  • the compounds S-2 to S-14 are made in an analogous manner from the corresponding compounds of formula II and Isocyanates produced.
  • the color photographic recording material according to the invention contains at least one photosensitive silver halide emulsion layer and preferably a sequence several such photosensitive silver halide emulsion layers and optionally further auxiliary layers such as in particular protective layers and between the photosensitive Layers of non-photosensitive Binder layers, according to the present invention at least one of the existing photosensitive Silver halide emulsion layers according to the invention Connection in combination with a magenta coupler of the pyrazoloazole coupler type is.
  • the compounds of the invention act in primarily as a light stabilizer, i.e. the formed from the color coupler in the chromogenic development Azomethine dyes exhibit in the presence of Compounds according to the invention increased considerably Stability against exposure to light.
  • a light stabilizer i.e. the formed from the color coupler in the chromogenic development Azomethine dyes exhibit in the presence of Compounds according to the invention increased considerably Stability against exposure to light.
  • Oil formers can be used as coupler solvents.
  • the compounds according to the invention preferably do this 10 to 60 wt .-% of the total amount of oil in the respective layer. The fact that more Oil formers may only be required in smaller quantities are beneficial for shift load and / or the total layer thickness of the invention Recording materials.
  • the compounds of the invention fall in the manufacture (Implementation of active hydrogen atoms Compounds with isocyanates) mostly as low-melting Solids on and are as a solution in aprotic (hydrophobic) solvents, e.g. Ethyl acetate, during incorporation into the casting solution for the concerned Layer, if necessary together with the respective Color coupler used.
  • aprotic (hydrophobic) solvents e.g. Ethyl acetate
  • the familiarization takes place in the usual way, if necessary further Auxiliary solvents and / or high-boiling coupler solvents, so-called oil formers can be used.
  • Silver halide can be used as halide chloride, Contain bromide or iodide or mixtures thereof.
  • the halide content can be at least one 0 to 15 mol% layer of iodide, 0 to 100 mol% consist of chloride and 0 to 100 mol% of bromide.
  • silver bromide iodide emulsions with high chloride content up to pure silver chloride emulsions are used.
  • It can are mainly compact crystals, e.g. are regular cubic or octahedral or transitional forms can have. But preferably also platelet-shaped crystals are present, their average Ratio of diameter to thickness is preferably at least 5: 1, the diameter a grain is 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, where the ratio of diameter to thickness is significantly larger than 5: 1, e.g. 12: 1 to 30: 1.
  • the silver halide grains can also be multi-layered Have grain structure, in the simplest case with an inner and an outer grain area (core / shell), wherein the halide composition and / or other modifications, such as Endowments of the individual Grain areas are 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 both be homo- and heterodisperse. Homodisperse grain size distribution means 95% of the grains are not deviate more than ⁇ 30% from the average grain size.
  • the emulsions can also other silver salts, e.g. contain organic silver salts, such as silver benzotriazolate or silver behenate.
  • Two or more types of silver halide emulsions which are made separately, as a mixture be used.
  • the emulsions can be chemically and in the usual way or be spectrally sensitized; you can also by suitable additives must be stabilized.
  • Suitable chemical Sensitizers, spectral sensitizing dyes and stabilizers are, for example, in Research Disclosure 17643 (December 1978); referred special attention is paid to chapters III, IV and VI.
  • the color photographic recording material according to the invention contains preferably the one according to the invention Combination of pyrazoloazole coupler and connection of the Formula I containing, normally green-sensitized Silver halide emulsion layer further silver halide emulsion layers for recording light of the other spectral ranges red and blue.
  • the purpose of the photosensitive layers is known Spectrally by suitable sensitizing dyes sensitized.
  • Suitable green sensitizers are, for example 9-ethyl carbocyanines with benzoxazole, naphthoxazole or a benzoxazole and a benzthiazole as basic end groups as well as benzimidazocarbocyanines, which also may be further substituted and also at least a sulfoalkyl group on heterocyclic nitrogen must contain.
  • Each of the light-sensitive layers mentioned can consist of consist of a single layer or in a known manner, e.g. with the so-called double layer arrangement, too two or more silver halide emulsion partial layers include (DE-C-1 121 470).
  • negative films usually red sensitive silver halide emulsion layers arranged closer to the substrate than those sensitive to green Silver halide emulsion layers and these again closer than blue-sensitive, which is generally between green sensitive layers and blue sensitive Layers a non-photosensitive yellow filter layer.
  • blue-sensitive which is generally between green sensitive layers and blue sensitive Layers a non-photosensitive yellow filter layer.
  • the means for preventing the Incorrect diffusion of developer oxidation products included can.
  • Color photographic recording materials according to the invention usually contain in spatial and spectral Assignment to the silver halide emulsion layers different spectral sensitivity color coupler to generate the different part color images Cyan, magenta and yellow, with the invention Connections together with the respective color coupler preferably a green-sensitive silver halide emulsion layer assigned.
  • Spatial assignment is understood to mean that the color coupler is in such a spatial Relationship to the silver halide emulsion layer finds that an interaction between them is possible which is a visual match between the silver picture formed during development and the allows the color coupler generated color image. This is in usually achieved in that the color coupler in the Silver halide emulsion layer itself is included or in a neighboring one if necessary non-photosensitive binder layer.
  • Spectral assignment means that the Spectral sensitivity of each of the photosensitive Silver halide emulsion layers and the color of the the spatially assigned color coupler Partial color image in a certain relationship to each other stand, each of the spectral sensitivities (Red, green, blue) another color of the concerned Partial color image (generally e.g. the colors cyan, Purple or yellow in this order).
  • Each of the different spectrally sensitized silver halide emulsion layers can one or can also several color couplers can be assigned. When multiple silver halide emulsion layers same spectral sensitivity are present, each of them can be one Color couplers included, but these color couplers are not necessarily need to be identical. You should only at least approximately in the color development result in the same color, usually a color that is complementary to the color of the light for which the silver halide emulsion layers concerned predominantly are sensitive.
  • couplers can be 4 equivalent couplers, but also act as 2-equivalent couplers.
  • the latter are derived from the 4 equivalent couplers that they have a substituent in the coupling site included, which split off at the clutch becomes.
  • the 2-equivalent couplers include those which are colorless, as well as those which are intense Have their own color in the color coupling disappears or due to the color of the image dye produced is replaced (mask coupler), but also the White couplers that react with color developer oxidation products essentially colorless products surrender.
  • Coupler to be expected in the coupling point releasable residue contained in the reaction with color developer oxidation products is set free and either directly or after from the primary split off remainder one or more other groups have been split off (e.g. DE-A-27 03 145, DE-A-28 55 697, DE-A-31 05 026, DE-A-33 19 428), a specific one desired photographic effectiveness unfolds, e.g. as a development inhibitor or accelerator.
  • Examples the known ones for such 2-equivalent couplers DIR couplers as well as DAR or. FAR coupler.
  • the couplers used especially those according to the invention used pyrazoloazole type magenta couplers, for example of the formulas IV and V, can also in polymeric form, e.g. as a polymer latex for use reach.
  • High molecular weight color couplers are described, for example in DE-C-1 297 417, DE-A-24 07 569, DE-A-31 48 125, DE-A-32 17 200, DE-A-33 20 079, DE-A-33 24 932, DE-A-33 31 743, DE-A-33 40 376, EP-A-27 284, US-A-4 080 211.
  • the high molecular color couplers are usually by polymerizing ethylenically unsaturated monomers Color couplers manufactured.
  • the color couplers used can also be those that Dyes with poor or limited mobility deliver.
  • a mobility that is measured in this way is that the contours of chromogenic development formed discrete dye stains run and are smeared into each other.
  • This degree of mobility is to be distinguished on the one hand from the usual Case of complete immobility in photographic Layers used in conventional photographic materials for the color couplers or from them Dyes produced is aimed at a possible to achieve high sharpness, and on the other hand by the case of complete mobility of the dyes, the for example in color diffusion processes becomes.
  • the latter dyes usually have about at least one group they are in alkaline Make medium soluble.
  • the extent of the invention aimed weak mobility can be controlled are made by varying substituents, for example the solubility in the organic medium of the oil former or the affinity for the binder matrix in a more targeted manner Way to influence.
  • the color photographic Recording material of the present Invention contain other additives, such as Antioxidants, dye stabilizers and Means for influencing the mechanical and electrostatic Properties as well as UV absorbers.
  • additional connections are combined with the compounds of the invention, i.e. in the same Binding agent layer or in adjacent to each other Binder layers used.
  • Additives to improve the dye, coupler and White stability and to reduce the color fog can belong to the following chemical substance classes: Hydroquinones, 6-hydroxychromanes, 5-hydroxycoumarans, Spirochromanes, spiroindanes, p-alkoxyphenols, steric hindered phenols, gallic acid derivatives, Methylenedioxybenzenes, aminophenols, sterically hindered Amines, derivatives with esterified or etherified phenolic hydroxyl groups, metal complexes.
  • R -C 8 H 17 -t
  • R 1 -C 3 H 7 -i R
  • R 1 -C 4 H 9 -t
  • R 1 -C 5 H 11 -t
  • Compounds that absorb UV light are intended on the one hand to protect the image dyes from fading by UV-rich daylight and, on the other hand, as filter dyes to absorb the UV light in daylight upon exposure and thus improve the color rendering of a film. Connections of different structures are usually used for the two tasks.
  • 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).
  • Ultraviolet absorbing couplers such as Cyan couplers of the ⁇ -naphthol type
  • ultraviolet absorbing Polymers are used. These ultraviolet absorbents can be done by pickling in a special Layer fixed.
  • the invention is used to produce color photographic images color photographic recording material, assigned to at least one silver halide emulsion layer a color coupler and a connection of the Formula I contains, with a color developer compound developed.
  • Can be used as a color developer compound use all developer connections that the Have ability in the form of their oxidation product Color couplers react to azomethine dyes.
  • Suitable Color developer compounds are aromatic at least compounds containing a primary amino group of the p-phenylenediamine type, for example N, N-dialkyl-p-phenylenediamine, 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-phenylenediamine such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methylsulfonamidoethyl) -3-methyl-p-phenylenediamine, 1- (N-ethyl-
  • 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 Fe 3+ salts and Fe 3+ 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 of corresponding phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • Samples 2 to 12 were prepared in the same way as sample 1, with the difference that the tricresyl phosphate used in sample 1 was replaced in sample 2 (also compare samples 6-9) and that a light stabilizer was additionally used in samples 3-12 , namely in samples 3-11 a compound of formula I (according to the invention) and in sample 12 the comparison compound of formula: Samples 1-12 contained either tricresyl phosphate or dibutyl phthalate as oil formers (see Table 1).
  • the samples obtained were then exposed behind a graduated gray wedge.
  • the materials were then processed in the following manner using the processing baths listed below: development 210 s, 33 ° C bleaching 50 s, 20 ° C Fix 60 s, 20 ° C Water 120 s, 20 ° Dry.
  • the example shows that the compounds of the invention high maximum color densities can be achieved and at the same time improves the light stability of the image dye becomes.
  • the connection used as a comparison VP-1 according to GB 2 135 788 causes less improvement the light stability.
  • Example 1 As described in Example 1, it becomes a layer structure produced with the difference that in the green sensitive Layer instead of the magenta coupler M-5 Magenta coupler M-14 is used. You get that Sample 13 (comparison).
  • Samples 14-18 are prepared in the same manner as sample 13, except that layer 3 in sample 13 has one of the compounds according to the invention added. In the same way, sample 19 is prepared using the comparative compound VP-1. Processing and testing are carried out as described in Example 1.
  • the example shows that by using the invention Compounds the light stability of the image dyes is improved.
  • the used as a comparison Connection VP-1 according to GB 2 135 788 causes a lower one Improve light stability.
  • a color photographic recording material suitable for a rapid processing process was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene.
  • the quantities given relate to 1 m 2 .
  • the corresponding amounts of AgNO 3 are given for the silver halide application.
  • Samples 21 to 27 were produced in the same way as sample 20, with the difference that the 4th layer (sensitive to green) is a light stabilizer according to the invention of the formula I (samples 21 to 25) or the comparative compounds VP-1 and VP-2 (samples 26 or 27) were added.
  • the example shows a significant improvement in Light stability of the image dyes by the invention Connections as opposed to those for comparison used connections VP-1 and VP-2.
  • a color photographic recording material suitable for reversal processing was produced by applying the following layers in the order given to a transparent layer support made of cellulose triacetate provided with an adhesive layer.
  • the quantities given relate to 1 m 2 .
  • the corresponding amounts of AgNO 3 are given for the silver halide application.
  • Samples 29-33 are made in the same manner like sample 28 with the difference that the 6th and the 7th layer (green-sensitive layers) according to the invention Compound of formula I (samples 29-32) or the Compound VP-2 (sample 33) is added.
  • the maximum color density was then measured (Tab. 4) and the samples were exposed to the light of a xenon lamp standardized for daylight and exposed to 7.2 x 10 6 lx ⁇ h; the percentage decrease in density was then measured.
  • the example shows that the compounds according to the invention improve the light stability of the image dyes.
  • the connection VP-2 set as a comparison causes less improvement.

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

Claims (2)

  1. Matériau d'enregistrement photographique couleur comportant au moins une couche d'émulsion d'halogénure d'argent et un coupleur chromogène associé à celle-ci, caractérisé en ce qu'il contient en association à au moins une couche d'émulsion d'halogénure d'argent sensible à la lumière une combinaison d'un coupleur pyrazoloazole et d'un composé de formule générale I ou des formules VI-X :
    Figure 00650001
    Figure 00650002
    Figure 00650003
    Figure 00650004
    Figure 00660001
    Figure 00660002
    où
    R1
    représente H, un reste clivable dans des conditions alcalines, alkyle ou aryle,
    R2
    représente -OH, alkyle, aryle, alcoxy ou
    Figure 00660003
    R3, R4, R5 et R6
    représentent H, -OH, -COOH, -SO3H, -SO2H, alkyle, aryle, alcoxy, alkylsulfonyle, arylsulfonyle, sulfamoyle éventuellement substitué, acylamino ou
    Figure 00660004
    où au moins l'un des restes R2, R3, R4, R5 et R6 est un reste de formule
    Figure 00670001
    A
    représente un alkylène ayant 1 à 6 atomes de C,
    n
    représente 0 ou 1,
    R7
    représente H ou un alkyle éventuellement substitué par exemple par -COOH ou -SO3H, par exemple carboxyméthyle,
    R8
    représente un groupe alkyle, cycloalkyle ou aryle de 4 à 20 atomes de C, substitué une ou plusieurs fois par un groupe de formule
    Figure 00670002
    où
    R1 à R7, A et n
    ont les significations déjà indiquées, ou un alkyle, cycloalkyle ou aryle non substitué ayant 4 à 20 atomes de C,
    R1 et R3
    peuvent former un cycle à 5 ou 6 chaínons, où R2 = -OH ou alcoxy,
    R2 et R4
    peuvent former un cycle carbocyclique à 5 ou 6 chaínons.
  2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que le coupleur pyrazoloazole correspond à l'une des formules IV et V
    Figure 00670003
    où
    X
    représente H ou un groupe libérable dans les conditions du développement chromogène,
    R1, R2
    représentent H, alkyle, aralkyle, aryle, alcoxy, aroxy, alkylthio, arylthio, amino, anilino, acylamino, cyano, alcoxycarbonyle, carbamoyle, sulfamoyle, ces restes pouvant être substitués encore.
EP93103858A 1992-03-23 1993-03-10 Matériau photographique d'enregistrement Expired - Lifetime EP0563638B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4209346A DE4209346A1 (de) 1992-03-23 1992-03-23 Fotografisches Aufzeichnungsmaterial
DE4209346 1992-03-23

Publications (2)

Publication Number Publication Date
EP0563638A1 EP0563638A1 (fr) 1993-10-06
EP0563638B1 true EP0563638B1 (fr) 1998-06-17

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Country Status (4)

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EP (1) EP0563638B1 (fr)
JP (1) JPH0643614A (fr)
DE (2) DE4209346A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10111655A1 (de) * 2001-03-12 2002-10-02 Agfa Gevaert Ag Inkjet-Tinte
JP5892327B2 (ja) 2012-03-15 2016-03-23 Ｊｆｅスチール株式会社 無方向性電磁鋼板の製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0542053A1 (fr) * 1991-11-11 1993-05-19 Agfa-Gevaert AG Matériau photographique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3435443A1 (de) * 1984-09-27 1986-04-03 Agfa-Gevaert Ag, 5090 Leverkusen Fotografisches aufzeichnungsmaterial
DE3501722A1 (de) * 1985-01-19 1986-07-24 Agfa-Gevaert Ag, 5090 Leverkusen Lichtempfindliches, stabilisiertes fotografisches aufzeichnungsmaterial
JPH0762759B2 (ja) * 1986-01-22 1995-07-05 コニカ株式会社 ハロゲン化銀写真感光材料
JPH0648372B2 (ja) * 1986-11-13 1994-06-22 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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0542053A1 (fr) * 1991-11-11 1993-05-19 Agfa-Gevaert AG Matériau photographique

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JPH0643614A (ja) 1994-02-18
DE4209346A1 (de) 1993-09-30
EP0563638A1 (fr) 1993-10-06
DE59308679D1 (de) 1998-07-23
US5340709A (en) 1994-08-23

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