EP0257451B1 - Matériau d'enregistrement photographique couleur - Google Patents

Matériau d'enregistrement photographique couleur Download PDF

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Publication number
EP0257451B1
EP0257451B1 EP87111670A EP87111670A EP0257451B1 EP 0257451 B1 EP0257451 B1 EP 0257451B1 EP 87111670 A EP87111670 A EP 87111670A EP 87111670 A EP87111670 A EP 87111670A EP 0257451 B1 EP0257451 B1 EP 0257451B1
Authority
EP
European Patent Office
Prior art keywords
color
layer
silver halide
alkyl
oil
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.)
Expired - Lifetime
Application number
EP87111670A
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German (de)
English (en)
Other versions
EP0257451A3 (en
EP0257451A2 (fr
Inventor
Günter Dr. Renner
Johannes Dr. Sobel
Klaus Dr. Wagner
Günter Dr. Junkers
Friedhelm Dipl.-Chem. Sommer
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
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Publication date
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Publication of EP0257451A2 publication Critical patent/EP0257451A2/fr
Publication of EP0257451A3 publication Critical patent/EP0257451A3/de
Application granted granted Critical
Publication of EP0257451B1 publication Critical patent/EP0257451B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C7/3003—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
    • G03C7/3012—Combinations of couplers having the coupling site in pyrazolone rings and photographic additives
    • 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
    • G03C7/3885—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 solvent

Definitions

  • the invention relates to a color photographic recording material with at least one light-sensitive silver halide emulsion layer, to which a pyrazolone magenta coupler and an oil former are assigned.
  • magenta couplers In general, compounds derived from pyrazolone-5 are used as magenta couplers, ie as color couplers which are suitable for producing the magenta color image.
  • Common purple couplers are, for example Pyrazolone-5 compounds which are substituted in the 3-position by an acylamino group.
  • 3-anilinopyrazolone-5-couplers are characterized by narrow-band absorption, which leads to brilliant color renditions, by low secondary densities in both the red and the blue spectral range, by heating, tropical and storage cabinet stability, by excellent light stability that with p -Phenylenediamines formed azomethine dyes and characterized by high reactivity and coupling activity.
  • the invention was therefore based on the object of finding a way of using 3-anilinopyrazolones in which the disadvantages indicated above do not occur, but the advantageous properties are retained.
  • halogen such as chlorine and bromine
  • Alkoxy R1, R2 and R5 is in particular C1-C16 alkoxy.
  • Acylamino R1 and R2 or as a removable group X preferably corresponds to the formulas and where R5 is alkyl, aryl, alkoxy or aryloxy and R6 is hydrogen or C1-C4-alkyl.
  • Alkyl R2, R3 and R5 is in particular C1-C16 alkyl, Aryl or aryloxy R5 are especially phenyl and phenoxy.
  • the alkoxy-carbamyl radicals preferably have C1-C16 alkoxy groups.
  • Cycloalkyl R3 is especially C5-C7-cycloalkyl.
  • R4 is preferably methoxy, cyclopentyloxy, cyclohexyloxy or chlorine.
  • Alkylthio R1 is especially C1-C16 alkylthio.
  • Couplers and / or oil formers may be located in a layer adjacent to the photosensitive silver halide emulsion layer, but are preferably incorporated into the photosensitive silver halide emulsion layer.
  • Known methods for incorporating couplers and oil formers into the silver halide emulsion layer are described, for example, in US Pat. No. 2,322,027.
  • Suitable phenolic oil formers correspond to the following formulas:
  • the color photographic recording material according to the invention contains at least one light-sensitive silver halide emulsion layer and preferably a sequence of several such light-sensitive silver halide emulsion layers and, if appropriate, non-light-sensitive binder layers arranged between them.
  • the oil-forming agent according to the invention can be used alone or together with other known oil-forming agents, but if the magenta coupler is dissolved in a mixture of oil-forming agents, such a mixture consists of more than 50% by weight of an oil-forming agent of the present invention.
  • the light-sensitive silver halide emulsions used in the light-sensitive layers can contain chloride, bromide and iodide or mixtures thereof as the halide.
  • the halide content of at least one layer can consist of 0 to 12 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. They can be characterized in that they essentially have a thickness of more than 0.2 ⁇ m.
  • the average ratio of diameter to thickness is preferred less than 8: 1, whereby 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 heterodisperse or else monodisperse emulsions, which preferably have an average grain size of 0.3 ⁇ m to 1.2 ⁇ m.
  • the silver halide grains can also have a layered grain structure.
  • the emulsions can be chemically and or spectrally sensitized in the usual way; they can also be stabilized by suitable additives. Suitable chemical sensitizers, spectral sensitizing dyes and stabilizers are described, for example, in Research Disclosure 17643 (December 1978); Reference is made in particular to chapters III, IV and VI.
  • the color photographic recording material according to the invention preferably contains at least one silver halide emulsion layer for the recording of 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.
  • Blue-sensitive silver halide emulsion layers do not necessarily have to contain a spectral sensitizer, since in many cases the intrinsic sensitivity of the silver halide is sufficient for the recording of blue light.
  • Each of the 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 layer support than green-sensitive silver halide emulsion layers and these in turn are closer than blue-sensitive layers, a non-light-sensitive yellow filter layer generally being located between green-sensitive layers and blue-sensitive layers.
  • 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 immediately adjacent to one another or arranged in such a way that a light-sensitive layer with a different spectral sensitivity is located between them (DE-A-1 958 709, DE-A-2 530 645, DE-A -2 622 922).
  • Color photographic recording materials according to the invention usually contain, in spatial and spectral assignment to the silver halide emulsion layers of different spectral sensitivity, color couplers for producing the different partial color images cyan, purple and yellow, the pyrazolone purple couplers dispersed with the oil former of the present invention are generally assigned to a green-sensitive silver halide emulsion layer.
  • 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 allows an image-wise match 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 of the relevant partial color image (in general, for example, the colors cyan, purple or yellow 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 multiple silver halide emulsion layers of the same spectral sensitivity, each of them may contain a color coupler, but these color couplers are not necessarily need to 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, generally a coupler of the phenol or ⁇ -naphthol type.
  • Green-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for generating the purple partial color image, with other purple couplers, e.g. of the indazolone or pyrazoloazole type are used.
  • blue-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for producing the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • Color couplers of this type are known in large numbers and are described in a large number of patents. Examples include the publications “Farbkuppler” by W. PELZ in “Mitanderen aus den Anlagens Laboratorien der Agfa, Leverkusen / Ober", Volume III, page 111 (1961) and by K. VENKATARAMAN in “The Chemistry of Synthetic Dyes", Vol 4, 341 to 387, Academic Press (1971).
  • Color couplers can be either conventional 4-equivalent couplers or 2-equivalent couplers, which require a smaller amount of silver halide to produce the color.
  • 2-equivalent couplers are derived from the 4-equivalent couplers in that they contain a substituent in the coupling site, which is split off during the coupling.
  • the 2-equivalent couplers include both those that are practically colorless and 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.
  • the latter couplers can also be present in the light-sensitive silver halide emulsion layers and serve there as mask couplers to compensate for the undesired secondary densities of the image dyes.
  • the known white couplers are also to be counted among the 2-equivalent couplers, but they do not give any dye on reaction with color developer oxidation products.
  • the 2-equivalent couplers also include those couplers which contain a detachable residue in the coupling point, which is released when reacting with color developer oxidation products and thereby develops a certain desired photographic activity, for example as a development inhibitor or accelerator. Examples of such 2-equivalent couplers are the known DIR couplers as well as DAR and FAR couplers.
  • the cleavable residue can also be a ballast residue, so that in the reaction with color developer oxidation products coupling products, for example dyes, can be obtained which are diffusible or at least have a weak or restricted mobility.
  • Weak or restricted mobility means mobility that is dimensioned such that the contours of the discrete dye spots formed in the chromogenic development 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 the 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 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 usual supports e.g. Cellulose ester supports, e.g. Cellulose acetate and polyester.
  • paper supports which can optionally be coated, e.g. with polyolefins, especially with polyethylene or polypropylene.
  • polyolefins especially with polyethylene or polypropylene.
  • hydrophilic film-forming agents for example proteins, in particular gelatin, are suitable as protective colloids or binders for the layers of the recording material.
  • Casting aids and plasticizers can be used. Reference is made to Research Disclosure 17643, Chapter IX, XI and XII.
  • the layers of the photographic material can be hardened in the usual way, for example with hardeners which contain at least two reactive oxirane, aziridine or acryloyl groups. Furthermore, it is also possible to harden the layers in accordance with the process described in DE-A-22 18 009. It is also possible to harden the photographic layers or the color photographic multilayer materials with hardeners of the diazine, triazine or 1,2-dihydroquinoline series or with hardeners of the vinyl sulfone type. Other suitable curing agents are known from DE-A-24 39 551, DE-A-22 25 230, DE-A-24 39 551 and also from Research Disclosure 17 643, Chapter X. The stabilizing effect of the oil formers according to the invention is particularly pronounced when hardening agents which activate carboxyl groups, e.g. Carbamoylpyridinium or carbamoyloxypyridinium salts can be used.
  • hardening agents which activate carboxyl groups e.g. Carbamoylpyr
  • Suitable color developer substances for the material according to the invention are in particular those of the p-phenylenediamine type, for example 4-amino-N, N-diethyl-aniline hydrochloride, 4-amino-3-methyl-N-ethyl-N- ⁇ - (methanesulfonamido) ethylaniline sulfate hydrate, 4 -Amino-3-methyl-N-ethyl-N- ⁇ -hydroxyethylaniline sulfate, 4-amino-N-ethyl-N- (2-methoxyethyl) -m-toluidine-di-p-toluenesulfonic acid and N-ethyl-N- ⁇ -hydroxyethyl-p-phenylenediamine. Further useful color developers are described, for example, in J.Amer.Chem.Soc. 73 , 3100 (1951) and in G. Haist, Modern Photographic Processing, 1979, John Wi
  • the material is usually bleached and fixed. Bleaching and fixation and fixation 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, nitrilotriacetic acid, iminodiacetic acid, N-hydroxyethyl acetic acid diamine , Alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • a solution of 100 g of coupler, 45 g of oil former (tricresyl phosphate or phenols according to the invention or mixtures thereof), 200 g of ethyl acetate and 2 g of sodium dodecylbenzenesulfonate are stirred into 1 l of 10% strength by weight gelatin solution at 45 ° C. using an intensive stirrer. After stirring for a further 5 minutes, the mixture is passed through a high-pressure homogenizer (Knollenberg) or ultrasonic homogenizer (Sonic) and the ethyl acetate is removed by evaporation in vacuo.
  • Knollenberg high-pressure homogenizer
  • Sonic ultrasonic homogenizer
  • the dispersions produced in this way have an excellent shelf life both in cold storage (at 4 - 10 ° C) and when stored at elevated temperatures (for example at 40 ° C) without the separation of crystals or coarse particles.
  • the following layers were applied in each case in the order given here on a transparent layer support made of cellulose triacetate.
  • Table 4 provides information about the combinations of purple coupler and oil former or oil former weight ratios used in the versions 6 and 7 described in the versions.
  • A is a comparison test.
  • the value of the blue-green density measured behind the red filter results from the residual secondary density of the pp-dye formed, since a co-coupling of the blue-green component in layers 3 and 4 is excluded by the presence of the 2,5-di-tertiary octylhydroquinone.

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

Claims (3)

  1. Matériau d'enregistrement photographique en couleurs avec au moins une couche photosensible d'émulsion d'halogénure d'argent à laquelle est associé un coupleur du type 3-anilinopyrazolone de formule I accompagné d'un oléifiant ou d'un mélange d'oléifiant,
    Figure imgb0044
     formule I dans laquelle
    n   signifie 1 à 5,
    m   signifie 1 à 3,
    X   représente un groupe scindable ou séparable,
    R₁   représente un halogène, un groupe alcoxy, alkylthio, acylamino, et
    R₂   représente un halogène, un groupe cyano, thiocyanato, alcoxy, alkyle, acylamino, alcoxycarbamyle,
    l'oléifiant ou au moins 50% en poids du mélange d'oléifiants consistant en un composé phénolique de formule générale II
    Figure imgb0045
     dans laquelle
    p   signifie 1 à 5,
    q   est un nombre ≦ (5 - p),
    R₃   représente un groupe alkyle ou cycloalkyle, et
    R₄   représente un substituant quelconque différent de alkyle,
    le nombre d'atomes de carbone du reste alkyle R₃ étant supérieur ou égal à 8.
  2. Matériau d'enregistrement photographique en couleurs selon la revendication 1, caractérisé en ce que des coupleurs et des oléifiants se trouvent dans la couche photosensible d'émulsion d'halogénure d'argent.
  3. Matériau d'enregistrement photographique en couleurs selon la revendication 1, caractérisé en ce que
    X   représente l'hydrogène, un groupe -S-aryle, -O-aryle, -NH-acyle, hétérocyclyle ou -N=N-aryle,
    R₁   représente un halogène, un groupe alcoxy en C₁-C₆, alkylthio en C₁-C₆ ou
    Figure imgb0046
     ou
    Figure imgb0047
     avec
    R₅   représentant un groupe alkyle, aryle, alcoxy ou aryloxy, et
    R₆   représentant l'hydrogène ou un groupe alkyle en C₁-C₄.
EP87111670A 1986-08-21 1987-08-12 Matériau d'enregistrement photographique couleur Expired - Lifetime EP0257451B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863628318 DE3628318A1 (de) 1986-08-21 1986-08-21 Farbfotografisches aufzeichnungsmaterial
DE3628318 1986-08-21

Publications (3)

Publication Number Publication Date
EP0257451A2 EP0257451A2 (fr) 1988-03-02
EP0257451A3 EP0257451A3 (en) 1989-05-03
EP0257451B1 true EP0257451B1 (fr) 1991-10-23

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Family Applications (1)

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EP87111670A Expired - Lifetime EP0257451B1 (fr) 1986-08-21 1987-08-12 Matériau d'enregistrement photographique couleur

Country Status (4)

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US (1) US4952487A (fr)
EP (1) EP0257451B1 (fr)
JP (1) JPS6353552A (fr)
DE (2) DE3628318A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0380223A1 (fr) * 1989-01-17 1990-08-01 Konica Corporation Filtre couleur et son procédé de production
EP0415883A3 (en) * 1989-08-28 1991-08-21 Ciba-Geigy Ag Stabilizers for colour photographic materials
GB9010966D0 (en) * 1990-05-16 1990-07-04 Kodak Ltd Photographic material comprising a magenta dye image forming coupler combination
DE69220905T2 (de) * 1991-07-17 1999-01-21 Eastman Kodak Co., Rochester, N.Y. Magenta bildfarbstoff-kuppler mit verbessertem farbton
US5376519A (en) * 1992-04-23 1994-12-27 Eastman Kodak Company Photographic material containing a coupler composition comprising magenta coupler, phenolic solvent, and at least one aniline or amine
US5411841A (en) * 1993-05-24 1995-05-02 Eastman Kodak Company Photographic elements containing magenta couplers and process for using same
US5455150A (en) * 1993-06-10 1995-10-03 Eastman Kodak Company Color photographic negative elements with enhanced printer compatibility
US5447831A (en) * 1993-10-19 1995-09-05 Eastman Kodak Company Photographic element employing hue correction couplers
JPH08160583A (ja) * 1994-12-12 1996-06-21 Konica Corp ハロゲン化銀カラー写真感光材料
US5563026A (en) * 1995-04-28 1996-10-08 Eastman Kodak Company Color negative element having improved green record printer compatibility
US20150198063A1 (en) 2014-01-14 2015-07-16 Alstom Technology Ltd Cooled stator heat shield

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2835579A (en) * 1955-08-31 1958-05-20 Eastman Kodak Co N-alkyl and acylphenol coupler solvents for color photography
JPS5334044A (en) * 1976-09-10 1978-03-30 Hitachi Ltd Clutch
JPS5699340A (en) * 1980-01-09 1981-08-10 Fuji Photo Film Co Ltd Color image stabilizing method to provide color fastness to light
JPS587632A (ja) * 1981-07-07 1983-01-17 Fuji Photo Film Co Ltd ハロゲン化銀カラ−感光材料
JPS59139031A (ja) * 1983-01-29 1984-08-09 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS602953A (ja) * 1983-06-20 1985-01-09 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS6086544A (ja) * 1983-10-18 1985-05-16 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS62141556A (ja) * 1985-12-14 1987-06-25 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPS62247368A (ja) * 1986-04-21 1987-10-28 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
DE3613974C2 (de) * 1986-04-25 1996-01-25 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial

Also Published As

Publication number Publication date
EP0257451A3 (en) 1989-05-03
JPS6353552A (ja) 1988-03-07
DE3628318A1 (de) 1988-02-25
DE3774037D1 (fr) 1991-11-28
US4952487A (en) 1990-08-28
EP0257451A2 (fr) 1988-03-02

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