EP0442029A1 - Produit de reproduction photographique couleur avec des coupleurs jaunes formateurs de cyan - Google Patents

Produit de reproduction photographique couleur avec des coupleurs jaunes formateurs de cyan Download PDF

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Publication number
EP0442029A1
EP0442029A1 EP90114639A EP90114639A EP0442029A1 EP 0442029 A1 EP0442029 A1 EP 0442029A1 EP 90114639 A EP90114639 A EP 90114639A EP 90114639 A EP90114639 A EP 90114639A EP 0442029 A1 EP0442029 A1 EP 0442029A1
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EP
European Patent Office
Prior art keywords
recording material
coupler
color
cyan coupler
silver halide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP90114639A
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German (de)
English (en)
Inventor
Hans Dr. Langen
Dirk Dr. Hübner
Günter Dr. Renner
Heinz SchÀ¼tz
Erwin Dr. Ranz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert AG
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Agfa Gevaert AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0442029A1 publication Critical patent/EP0442029A1/fr
Withdrawn legal-status Critical Current

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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
    • G03C7/32—Colour coupling substances
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material

Definitions

  • the invention relates to a color photographic recording material with yellow cyan couplers.
  • Colored photographic images are usually produced by the chromogenic development process by developing imagewise exposed silver halide emulsion layers in the presence of suitable color couplers by means of suitable color-forming developer substances - so-called color developers.
  • a coupling reaction takes place between the oxidation product of the color developer, which arises in accordance with the image with the silver image produced, and the color coupler with the formation of a dye.
  • Naphtholic or phenolic cyan couplers are usually used to produce the cyan partial image.
  • the image dyes produced from this occasionally have undesirable secondary densities in the green and / or blue spectral range, which impair a true-to-color reproduction.
  • the present application relates to a color photographic recording material having at least one light-sensitive silver halide emulsion layer applied to a layer support, to which a colorless cyan coupler, a colored cyan coupler and a DIR compound are assigned, characterized in that the colored cyan coupler is a yellow dye; and that the DIR compound is one which, under the conditions of color development, releases an inhibitor or the precursor of an inhibitor with a diffusibility D f ⁇ 0.4.
  • a color photographic recording material colored with a yellow dye as represented by the colored cyan couplers used according to the invention, mainly absorbs blue light and has an absorption maximum between 360 and 470 nm.
  • the cyan coupler residue represented by CC can, for example, also have the same coupling structure as the colorless coupler used.
  • the bivalent connecting group represented by L can have any structure, as long as this ensures easy separation from the coupling point in the case of color coupling.
  • L is through an oxygen, sulfur or nitrogen atom linked to the coupling point of the coupler and may optionally contain one or more of the following groups alternating with alkylene or arylene groups: -O-, -S-, -NH-SO2-, -O-CO-, -O-CO-NH-, -CO-NH-.
  • photographically inert substituents represented by Q1, Q2 are, for example, halogen, alkoxy, alkyl, acylamino, carbamoyl, alkoxycarbonyl, CN, nitro or CF3.
  • Photographically inert means that these substituents do not significantly affect the photographic properties of the light-sensitive material either before or after the azo dye is released; however, they can very well have an influence on the color of the azo dye or of the colored coupler.
  • An alkyl radical represented by R1, R2 or R5 preferably contains 1-4 C atoms and can be substituted, e.g. with a carboxyl group.
  • An aryl group represented by R1, R2 or R5 is preferably phenyl, optionally substituted, e.g. with halogen, alkyl, alkoxy, acylamino, carbamoyl, sulfamoyl or sulfo.
  • a heterocyclic group represented by R2 is, for example, pyridyl, thienyl, benzthiazolyl.
  • the alkyl or alkoxy groups optionally contained in R3 and R4 preferably have 1-4 C atoms.
  • the aryl radicals optionally contained in R3 and R4 are in particular phenyl radicals which can be substituted with the same substituents as a phenyl radical represented by R1, R2 or R5.
  • Carbamoyl and sulfamoyl include carbamoyl or sulfamoyl residues substituted on the N atom (for example by alkyl or aryl).
  • Acylamino includes those acylamino residues whose acyl group is derived from aliphatic or aromatic carbamic or sulfamic acids or carbonic acid monoesters.
  • Examples of coupling components of the formula III are the following:
  • Examples of residues of coupling components of the formulas IV and V are the following:
  • Examples of yellow cyan couplers of formula I according to the invention are the following:
  • the inhibitors released during development from the DIR compounds used according to the invention can be heterocyclic mercapto compounds, or else nitrogen-containing heterocyclic compounds without mercapto groups, for example triazole or benzotriazole derivatives.
  • Such inhibitors as a constituent of DIR compounds are known in large numbers and are described, for example, in US Pat. Nos. 3,227,554, 3,617,291, 24 24 006, 2655 781, DE-A. A-28 42 063, DE-A-32 09 486, DE-A-34 27 235, DE-A-37 11 418.
  • D f degree of diffusion
  • Multilayer test materials A and B are made as follows:
  • the quantities refer to 1 m2.
  • the corresponding equivalent amount of AgNO3 is given for the silver halide application.
  • the silver halide emulsions are stabilized with 0.5 g of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene per 100 g of AgNO3.
  • test material B was also produced in the same way, but with the change compared to test material A that layer 2 is composed 0.346 g white coupler and 0.900 g gelatin.
  • test materials A and B are exposed in a dark room under room lighting with a 100 watt incandescent lamp at a distance of 1.5 m and an exposure time of 15 min.
  • Modified developers containing the development inhibitor to be tested are prepared in such a way that a 0.02 molar solution of the inhibitor in a methanol / water mixture (8: 2), which, if necessary, NaOH up to a pH of 9 contains, the developer is added and results in a diluted to 20 vol% developer by adding water.
  • Test materials A and B are each developed in the developer not containing the inhibitor and processed in the further steps.
  • the resulting blue green densities are measured with a densitometer.
  • the DIR compounds are very reactive, ie have a high reaction rate when reacting with developer oxidation products.
  • DIR compounds preferred according to the invention have a reactivity k of greater than 5000 l ⁇ mol ⁇ 1 ⁇ s ⁇ 1. Examples of suitable DIR compounds are listed below.
  • Cyan couplers of the general formulas VIa and VII are preferably used in which mean: R2 H or a group that can be released under the conditions of color development that does not impart color to the coupler; R3 Alkyl or aryl; R4 H, alkyl, aralkyl, acyl, where the acyl radical is derived from aliphatic or aromatic carboxylic or sulfonic acids from N-substituted carbamic or sulfinic acids or from carbonic acid semiesters, or R5 Alkyl; R6 a heterocyclic group or aryl; R7 a ballast remnant.
  • the recording material according to the invention has high interimage effects and excellent color rendering properties. It is also ideal for processing in high-speed processes. In particular, it has excellent bleachability. For example, such materials that have been cured to a swelling factor of ⁇ 3.5, measured in water of 10 ° dH at 20 ° C, can be completely bleached in less than 3 minutes.
  • the diffusion-resistant colorless cyan couplers, the colored cyan couplers of the formula I and the DIR compounds used according to the invention are introduced into the casting solution of the silver halide emulsion layers in a known manner or other colloid layers.
  • the oil-soluble or hydrophobic couplers can preferably be added to a hydrophilic colloid solution from a solution in a suitable coupler solvent (oil-forming agent), 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 couplers 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 coating solution for the photosensitive silver halide emulsion layer or another water-permeable layer before application.
  • the couplers can also be added separately and the couplers do not necessarily have to be added to the same layer.
  • the light-sensitive silver halide emulsions used can contain chloride, bromide and iodide or mixtures thereof as the halide.
  • the halide content of at least one layer consists of 0 to 20 mol% of iodide, 0 to 50 mol% of chloride and 50 to 100 mol% of bromide.
  • the crystals are predominantly compact, for example cubic or octahedral or have transitional forms and generally have an average grain size of more have than 0.2 ⁇ m.
  • the average ratio of diameter to thickness is preferably less than 8: 1, it being true that the diameter of a grain is defined as the diameter of a circle with a circle content corresponding to the projected area of the grain.
  • all or individual emulsions can also have essentially tabular silver halide crystals in which the ratio of diameter to thickness is greater than 8: 1.
  • the emulsions can be monodisperse emulsions which preferably have an average grain size of 0.3 ⁇ m to 1.2 ⁇ m.
  • the silver halide grains can have a layered grain structure.
  • hydrophilic film-forming agents are suitable as protective colloid or binder for the layers of the recording material, e.g. Proteins, especially gelatin. However, this can be replaced in whole or in part by other natural or synthetic binders. Casting aids and plasticizers can be used. Reference is made to Research Disclosure 17 643 (December 1978), in particular chapters IX, XI and XII.
  • the emulsions can be chemically and or spectrally sensitized in the usual way, they can be further stabilized with the usual silver halide stabilizing agents and the emulsion layers as well as other non-light-sensitive layers can be hardened in the usual way with known hardening agents be.
  • Suitable chemical sensitizers, spectral sensitizing dyes, stabilizers and curing agents are described, for example, in Research Disclosure 17643; Reference is made in particular to chapters III, IV, VI and X.
  • Color photographic recording materials usually contain at least one silver halide emulsion layer for recording light from each of 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.
  • the photographic emulsions can be spectrally sensitized using methine dyes or other dyes.
  • Particularly suitable dyes are cyanine dyes, merocyanine dyes and complex merocyanine dyes.
  • red sensitizers RS examples, in particular for negative and reversal film, are the red sensitizers RS, green sensitizers GS and blue sensitizers BS, which can be used individually or in combination with one another, for example RS-1 and RS-2, and GS-1 and GS -2.
  • Sensitizers can be dispensed with if the intrinsic sensitivity of the silver halide is sufficient for a certain spectral range, for example the blue sensitivity of silver bromides.
  • 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, can 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, which in turn are closer than blue-sensitive layers, with a non-light-sensitive yellow in general between green-sensitive layers and blue-sensitive layers Filter layer is located.
  • a layer which is not sensitive to light 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).
  • Such silver halide sublayers of the same spectral sensitivity generally have different photosensitivity (speed), the more sensitive sublayers generally being located further away from the layer support than less sensitive sublayers of the same spectral sensitivity.
  • 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, 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 that allows an image-like correspondence between the silver image formed during development and the color image generated 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 a possibly non-light-sensitive binder layer adjacent to it.
  • 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 partial color image ( in general, for example, the colors cyan, purple or yellow are assigned in this order).
  • One or more color couplers can be assigned to each of the differently spectrally sensitized silver halide emulsion layers. If there are several silver halide emulsion layers of the same spectral sensitivity, 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 therefore assigned at least one non-diffusing color coupler for producing the blue-green partial color image, in the present case at least one colorless cyan coupler, at least one yellow cyan coupler of the formula I and at least one DIR coupler with a diffusibility ⁇ 0.4.
  • an existing red or purple-colored secondary density of the cyan dye can also be masked if one of the usual red mask couplers is additionally assigned to the red-sensitive layers.
  • Such red cyan couplers are known and are described, for example, in DE-A-25 38 323.
  • Green-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler to produce the purple partial color image, and blue-sensitive silver halide emulsion layers are finally assigned at least one non-diffusing color coupler to produce the yellow partial color image.
  • Color couplers for producing the purple partial color image are generally couplers of the 5-pyrazolone, indazolone or pyrazoloazole type; suitable examples are
  • Color couplers for producing the yellow partial color image are generally couplers with an open-chain ketomethylene group, in particular couplers of the ⁇ -acylacetamide type; suitable examples of this are ⁇ -benzoylacetanilide couplers and ⁇ -pivaloylacetanilide couplers of the formulas
  • the couplers used i.e. in particular the cyan couplers, for example of the formulas VIa and VII
  • the magenta couplers e.g. 2-equivalent or 4-equivalent magenta couplers of the pyrazolone or pyrazoloazole type, for example of the formulas X and XI
  • the colored cyan couplers used according to the invention can also be in polymeric form, e.g. are used as polymer latex.
  • 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 weight color couplers are generally produced by polymerizing ethylenically unsaturated monomeric color couplers .
  • the color couplers used can also be those which provide dyes with poor or restricted mobility.
  • Weak or restricted mobility means mobility that is dimensioned such that the contours of the chromogenic development formed discrete dye spots run and are smeared into one another.
  • This degree of mobility is to be distinguished on the one hand from the usual case of complete immobility in photographic layers, which is sought in conventional photographic recording materials for the color couplers or the dyes produced therefrom, in order to achieve the highest possible sharpness, and on the other hand from the case of complete mobility of the dyes, which is sought for example in color diffusion processes.
  • the last-mentioned dyes usually have at least one group that make them soluble in the alkaline medium.
  • the extent of the weak mobility sought according to the invention can be controlled by varying substituents in order to influence, for example, the solubility in the organic medium of the oil former or the affinity for the binder matrix in a targeted manner.
  • the color photographic recording material of the present invention can contain further additives, such as, for example, antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties.
  • further additives such as, for example, antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties.
  • UV-absorbing compounds in one or more of the layers contained in the recording material, preferably in one of the upper layers. Suitable UV absorbers are described for example in US-A-3 253 921, DE-C-2 036 719 and EP-A-0 057 160.
  • the color photographic recording material according to the invention which contains at least one silver halide emulsion layer and at least one coupler of the formula I assigned to it, is developed with a color developer compound. All developer compounds which have the ability in the form of their oxidation product to react 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.
  • 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.
  • Example 1 the following compounds are used in addition to the couplers already mentioned:
  • Example 2 the procedure was analogous to that in Example 1, except that instead of colorless, almost colorless or yellowish coupling DIR compounds, bg and pp coupling DIR compounds were used.
  • Example 3 shows how the combination according to the invention systematically produces an approximately equally large and high interimage effect in all 3 color packets, which leads to color copies with excellent cost-effectiveness.
  • the layer structure corresponded to that of Example 1 with the following exceptions: In the layered structures 3-C, 3-D, 3-G and 3-H, 0.64 g of the cyan coupler C-2 was stored in the third layer and 0.12 g in the fourth layer instead of the cyan coupler C-4 and in the 3-I and 3-J layer constructions, 0.68 g in the 3rd layer and 0.14 g in the 4th layer of cyan coupler C-5.
  • Example 3 For this purpose, the materials mentioned in Example 3, 3-A, 3-B, 3-E, 3-F, 3-G, 3-H, 3-I and 3-J were subjected to the processing process described below after prior exposure.
  • Composition of the processing baths Make up to 1 liter with water after adjusting the pH to 10.5 with 1N KOH.
  • the final rinsing bath contains 0.5 g of Intrasol NP 9 from Bayer AG per l / water.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP90114639A 1990-02-10 1990-07-31 Produit de reproduction photographique couleur avec des coupleurs jaunes formateurs de cyan Withdrawn EP0442029A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4004039 1990-02-10
DE19904004039 DE4004039A1 (de) 1990-02-10 1990-02-10 Farbfotografisches aufzeichnungsmaterial mit neuen farbigen blaugruenkupplern

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EP0442029A1 true EP0442029A1 (fr) 1991-08-21

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0572894A3 (en) * 1992-06-03 1995-09-13 Agfa Gevaert Ag Color photographic recording material with a cyan-dir-coupler
US6011052A (en) * 1996-04-30 2000-01-04 Warner-Lambert Company Pyrazolone derivatives as MCP-1 antagonists

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10004446B4 (de) * 2000-02-03 2004-05-06 E.G.O. Elektro-Gerätebau GmbH Beleuchtungseinrichtung für eine Heizeinrichtung

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0313083A2 (fr) * 1987-10-22 1989-04-26 Fuji Photo Film Co., Ltd. Matériau photographique couleur à l'halogénure d'argent
DE3736048A1 (de) * 1987-10-24 1989-05-03 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit dir-verbindungen
DE3815469A1 (de) * 1988-05-06 1989-11-16 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit neuen farbigen blaugruenkupplern

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0313083A2 (fr) * 1987-10-22 1989-04-26 Fuji Photo Film Co., Ltd. Matériau photographique couleur à l'halogénure d'argent
DE3736048A1 (de) * 1987-10-24 1989-05-03 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit dir-verbindungen
DE3815469A1 (de) * 1988-05-06 1989-11-16 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit neuen farbigen blaugruenkupplern

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0572894A3 (en) * 1992-06-03 1995-09-13 Agfa Gevaert Ag Color photographic recording material with a cyan-dir-coupler
US6011052A (en) * 1996-04-30 2000-01-04 Warner-Lambert Company Pyrazolone derivatives as MCP-1 antagonists

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Publication number Publication date
DE4004039A1 (de) 1991-08-14

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