EP0318799B1 - Matériau de reproduction photographique couleur avec un coupleur phénolique bleu vert - Google Patents

Matériau de reproduction photographique couleur avec un coupleur phénolique bleu vert Download PDF

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Publication number
EP0318799B1
EP0318799B1 EP88119386A EP88119386A EP0318799B1 EP 0318799 B1 EP0318799 B1 EP 0318799B1 EP 88119386 A EP88119386 A EP 88119386A EP 88119386 A EP88119386 A EP 88119386A EP 0318799 B1 EP0318799 B1 EP 0318799B1
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EP
European Patent Office
Prior art keywords
alkyl
recording material
layer
aryl
color
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
EP88119386A
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German (de)
English (en)
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EP0318799A3 (en
EP0318799A2 (fr
Inventor
Hans Dr. Langen
Wolfgang Dr. Himmelmann
Reinhart Dr. Matejec
Erwin Dr. Ranz
Heinz Dr. Reif
Prem Dipl.-Ing. Lalvani
Gerd Dr. Krauss
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 of EP0318799A2 publication Critical patent/EP0318799A2/fr
Publication of EP0318799A3 publication Critical patent/EP0318799A3/de
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Publication of EP0318799B1 publication Critical patent/EP0318799B1/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
    • G03C7/32—Colour coupling substances
    • G03C7/34—Couplers containing phenols
    • G03C7/346—Phenolic couplers
    • 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 which contains at least one layer of a phenolic cyan coupler and a plasticizing acrylate polymer latex.
  • a color photographic recording material which contains at least one layer of a phenolic cyan coupler and a plasticizing acrylate polymer latex.
  • ballast in photographic layers causes poor mechanical properties of the respective photographic material.
  • the volume filling level of the gelatin should not be less than 45%, so that the known mechanical properties such as elongation at break, breaking strength etc. are acceptable.
  • the proportion of the binder has to be reduced.
  • the mechanical properties deteriorate, among other things. also sensitivity to pressure and tension, which are ultimately also reflected in the sensitometry. Even more rational manufacturing processes, which include result in higher material temperatures when watering, affect pressure and tensile sensitivity.
  • recording materials which have been hardened with such fragmenting hardeners, in particular in connection with the phenolic cyan couplers which have recently been used because of higher dye stability, have an increased sensitivity to mechanical stress.
  • Such recording materials for example, after bending, as e.g. is sometimes unavoidable when transporting film inside the camera with the emulsion layer being wound on the outside, a density drop in the bending area after development (winding error).
  • US-A-2 960 404 describes a method of adding polyhydric alcohols, e.g. Ethylene glycol, glycerin and trimethylolpropane for the gelatin layer. The addition of these compounds counteracts the winding error, but such compounds cause the surface of photographic recording materials to stick strongly.
  • polyhydric alcohols e.g. Ethylene glycol, glycerin and trimethylolpropane
  • the invention has for its object to provide a color photographic recording material which contains a phenolic cyan coupler and is hardened with a fragmenting hardener and which has a reduced sensitivity to mechanical stress. It has been found that the use of certain plasticizing acrylate polymer latexes as a layer additive can reduce the sensitivity to mechanical stress.
  • An acyl radical represented by R 1 is in particular an acyl radical which is derived from aliphatic or aromatic carboxylic acids, in particular halogen-, alkyl-, alkoxy- or aroxy-substituted carboxylic acids, or from N-alkyl- or N-aryl-substituted carbamic acids.
  • couplers of the formula I in which R2 is an acylamino group preference is given to those in which the acyl radical represented by R1 is derived from an N-phenylcarbamic acid, the phenyl ring preferably being substituted, for example by halogen, cyano, -CF3, alkylsulfonyl, Sulfamoyl or -SO2F.
  • the acrylate polymer used can be a homopolymer or a copolymer which has a lower proportion of one or more monomers (comonomers) copolymerizable with alkyl acrylate, for which, for example, the following are possible: acrylamide, acrylic acid, sulfonic acid group-containing acrylic monomers, e.g. ⁇ -acrylamido- ⁇ -methylpropanesulfonic acid (AMPS), hydroxyalkyl acrylate, glycidyl acrylate, alkoxyalkyl acrylate.
  • monomers e.g. ⁇ -acrylamido- ⁇ -methylpropanesulfonic acid (AMPS)
  • composition must be selected so that the proportion of the comonomer may have to be kept so low that a copolymer which is insoluble in water is always obtained as a latex during the copolymerization.
  • polymer latex also suitable as polymer latex are graft polymers of polyalkyl acrylate on suitable polymeric graft bases, e.g. on polyurethanes as described, for example, in US Pat. No. 3,791,857, or on gelatin or on polyvinylpyrrolidone.
  • alkyl acrylate copolymers with a small proportion of a copolymerized copolymerizable wetting agent, as described, for example, in EP-A-0 010 335.
  • the glass transition temperature Tg is decisive for the suitability as a softening acrylate polymer latex.
  • the glass transition temperature is determined using differential thermal analysis (G. W. MILLER, Applied Polymer Symposia No. 10, (1969), pp. 35-72).
  • Plasticizing polymers in the sense of the present invention are those with a glass transition temperature below -10 ° C.
  • the particles of the acrylate polymer latex used according to the invention can also be surrounded by a thin shell of a harder polymer and can be present as a so-called core / shell polymer, as described, for example, in DE-A-3 516 466.
  • a harder polymer can, for example, have a glass transition temperature of above 35 ° C.
  • Gelatin is preferably used as the proteinaceous binder in the recording material according to the invention.
  • the hardening agent used to harden the proteinaceous binder, in particular the gelatin corresponds to the following formula III A - B (III) wherein A and B denote parts of the curing agent which are bonded together by a reactive bond which is released in the course of the curing reaction, at least one of the A and B parts of the molecule remaining in the hardened binder matrix in modified form as a result of reaction with the binder as inert fiber .
  • the curing agents used according to the invention can be one of the two above assign designated groups.
  • the fragmenting hardeners of the first group split off water from the gelatin chains, which they add. As a result, they escape balance and then remain in the layer as inert fiber.
  • carboxyl group-activating hardeners are to be counted for this.
  • one part of the molecule is firmly incorporated into the crosslinked binder matrix when the gelatin chains are linked, while another part of the molecule forms a low-molecular inert fiber during the hardening reaction with the gelatin, which at least partially remains in the binder matrix.
  • Suitable fragmenting hardeners are, for example, water-soluble sulfates from a heteroaromatic bis- or polysulfone as described in DE-A-3 708 541 or water-soluble addition compounds from tertiary amine and a heteroaromatic bis- or polysulfone as described in DE-A-3 628 717.
  • the diffusion-resistant phenolic cyan coupler is incorporated into the coating solution of the red-sensitive silver halide emulsion layer together with the plasticizing acrylate polymer latex.
  • the preferably oil-soluble or hydrophobic couplers can be added to a hydrophilic colloid solution from a solution in a suitable coupler solvent (oil former), if appropriate 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 advantageously be first dispersed in an aqueous non-photosensitive solution of a hydrophilic colloid, whereupon the mixture obtained, if appropriate after the removal of the low-boiling organic solvents used, is mixed with the casting solution for the photosensitive silver halide emulsion layer or another water-permeable layer before application.
  • Suitable light-sensitive silver halide emulsions are emulsions of silver chloride, silver bromide or mixtures thereof, possibly with a low silver iodide content of up to 10 mol% in one of the commonly used hydrophilic binders.
  • Gelatin is preferably used as a binder for the photographic layers. However, this can be replaced in whole or in part by other natural or synthetic binders.
  • the emulsions can be chemically and spectrally sensitized in the usual way and the emulsion layers as well as other non-photosensitive layers are hardened in the usual way, for which purpose a fragmenting hardener is used according to the present invention.
  • Color photographic recording materials usually contain at least one silver halide emulsion layer for the recording of light in the three spectral ranges red, green and blue.
  • the light-sensitive layers are spectral in a known manner by means of suitable sensitizing dyes sensitized.
  • 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 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 usually arranged closer to the support than green-sensitive silver halide emulsion layers and these are in turn closer than blue-sensitive layers, a yellow filter layer which is not sensitive to light 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 for producing multicolored images usually contain, in spatial and spectral assignment to the silver halide emulsion layers of different spectral sensitivity, coloring compounds, here 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 to the silver halide emulsion layer that an interaction between them is possible which permits an image-wise match between the silver image formed during development and the color image 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.
  • a spectral assignment is to be 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, each of the spectral sensitivities (red, green, blue) having a different color of the relevant partial color image (e.g. teal, purple, yellow) is assigned.
  • 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 assigned at least one non-diffusing phenolic cyan coupler.
  • Green-sensitive silver halide emulsion layers are assigned at least one non-diffusing color coupler for producing the purple partial color image, color couplers of the 5-pyrazolone, indazolone or pyrazoloazole type usually being 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. One example is the publications "Color Coupler" by W.
  • the color couplers can be both conventional 4-equivalent couplers and 2-equivalent couplers in which a smaller amount of silver halide is required 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 when reacted with color developer oxidation products.
  • the 2-equivalent couplers include the known DIR couplers, which are couplers which contain a detachable residue in the coupling point, which is released as a diffusing development inhibitor when reacted with color developer oxidation products.
  • Other photographically active compounds for example development accelerators or fogging agents, can also be released during the development from such couplers.
  • the color photographic recording material of the present invention can contain further additives, for example antioxidants, dye-stabilizing agents and agents for influencing the mechanical and electrostatic properties.
  • further additives 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 use. 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 is developed with a color developer compound.
  • All developer compounds which have the ability in the form of their oxidation product with color couplers can be used as the color developer compound React azomethine dyes.
  • 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.
  • Iron-III complexes of aminopolycarboxylic acids are particularly preferred, 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.
  • Example 1 The formulas of the compounds used in Example 1 are listed below: Different versions of the specified recording material were produced, which differed only in the cyan coupler contained in layers 3 and 4 and the curing agent used, and in the presence or absence of a polymer according to the present invention.
  • cyan couplers were used for comparison:
  • General dispersion instructions for the cyan couplers 100 g of coupler are dissolved together with 80 g of dibutyl phthalate in 300 ml of ethyl acetate and at 50 ° C. with a high-speed mixing siren in 1.3 l of 7.5% gelatin, likewise heated to 50 ° C., which is additionally mixed with 10 g of sodium dodecylbenzenesulfonate. emulsified. The low-boiling solvent is then removed in vacuo and the remaining dispersion is allowed to solidify at 6 ° C.
  • the strips were evaluated using a Joyce-Gevaert densitometer. The difference in density of the cyan dye ⁇ D max / cyan visible on the test strips as a crossbar was measured.
  • the maximum density loss shown as a crossbar in Examples 1 and 2 can also be shown as a complete gradation as follows.
  • 2 sensitometer strips are individually stored as in the 1st test method.
  • the winding takes place with a counterweight of 100 g.
  • the strips are attached using extremely thin polyester adhesive tape (60 ⁇ m).
  • the strips are then exposed with a graduated gray wedge and processed as described in Example 1.
  • the blue-green gradations obtained are then measured.
  • the Ea-wrapped strip has a flatter bg gradation than the egg-wrapped strip.
  • Table 3 shows the values of the combination tested.

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

Claims (7)

  1. Matériau d'enregistrement photographique en couleur à au moins une couche contenant un halogénure d'argent photosensible et un coupleur en vert-bleu dans un solvant protéique et qui a été durci à l'aide d'un durcisseur du liant protéique formant au durcissement des matières de charge inertes qui restent dans la couche, caractérisé en ce que cette couche photosensible d'émulsion d'halogénure d'argent au moins contient un coupleur phénolique en vert-bleu résistant à la diffusion, de formule I
    Figure imgb0039
     dans laquelle
    R¹   représente un groupe acyle;
    R²   représente un groupe acylamino;
    R³   représente H ou un halogène, ou bien R² et R³ forment ensemble un noyau hétérocyclique azoté condensé;
    X   représente H, un halogène ou un groupe éliminable au couplage de couleur,
    et une dispersion de particules, insolubles dans l'eau, d'un polymère consistant principalement en motifs de structure polymérisés d'un monomère de formule II



            CH₂=CH-COO-R   (II)



    dans laquelle R représente un groupe alkyle en C₁-C₈, et qui a une température de transition du second ordre Tg inférieure à -10°C.
  2. Matériau d'enregistrement selon revendication 1, caractérisé en ce que le groupe acyle du groupe acylamino représenté par R² répond à la formule
    Figure imgb0040
     dans laquelle
    Z représente O ou S;
    R⁴ représente un groupe alkylène en C₁-C₂₀;
    R⁵ représente un halogène, un groupe hydroxy, carboxy, alkyle, cycloalkyle, aryle, aralkyle, alcoxy, aryloxy, alkylsulfamoyle, arylsulfamoyle, alkylsulfonamido, arylsulfonamido, alkylsulfonyle, arylsulfonyle, alcoxycarbonyle ou acyloxy; et m est un nombre allant de 1 à 3.
  3. Matériau d'enregistrement selon revendication 1, caractérisé en ce que le groupe acyle représenté dans la formule I par R¹ dérive d'un acide N-phénylcarbamique.
  4. Matériau d'enregistrement selon revendication 1, caractérisé en ce que les particules de polymère sont enrobées d'une enveloppe mince d'un polymère plus dur.
  5. Matériau d'enregistrement selon l'une des revendications 1 à 4, caractérisé en ce que le liant protéique consiste en gélatine durcie par un durcisseur de formule III



            A-B   (III)



    dans laquelle A et B sont des parties de la molécule du durcisseur qui sont liées entre elles par une liaison réactive, laquelle, dans le cours de la réaction de durcissement, est scindée, une au moins des parties de molécule A et B restant, sous la forme modifiée par la réaction avec la gélatine, à l'état de matière de charge inerte dans la gangue de gélatine durcie.
  6. Matériau d'enregistrement selon revendication 5, caractérisé en ce que le durcisseur est un durcisseur activant les groupes carboxyle.
  7. Utilisation d'une dispersion de particules, insolubles dans l'eau, d'un polymère consistant principalement en motifs de structure polymérisés d'un monomère de formule II de la revendication 1 et ayant une température de transition du second ordre Tg inférieure à -10°C dans un matériau d'enregistrement photographique en couleur en tant qu'additif à une couche contenant un halogénure d'argent photosensible et un coupleur phénolique en vert-bleu résistant à la diffusion dans un liant protéique et qui a été durci à l'aide d'un durcisseur du liant protéique avec formation de matières de charge inertes restant dans la couche en vue d'amoindrir la sensibilité aux contraintes mécaniques.
EP88119386A 1987-12-03 1988-11-22 Matériau de reproduction photographique couleur avec un coupleur phénolique bleu vert Expired - Lifetime EP0318799B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3740930 1987-12-03
DE19873740930 DE3740930A1 (de) 1987-12-03 1987-12-03 Farbfotografisches aufzeichnungsmaterial mit einem phenolischen blaugruenkuppler

Publications (3)

Publication Number Publication Date
EP0318799A2 EP0318799A2 (fr) 1989-06-07
EP0318799A3 EP0318799A3 (en) 1990-04-25
EP0318799B1 true EP0318799B1 (fr) 1993-12-15

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EP88119386A Expired - Lifetime EP0318799B1 (fr) 1987-12-03 1988-11-22 Matériau de reproduction photographique couleur avec un coupleur phénolique bleu vert

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EP (1) EP0318799B1 (fr)
JP (1) JPH01187550A (fr)
DE (2) DE3740930A1 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3443700A1 (de) * 1984-11-30 1986-06-05 Agfa-Gevaert Ag, 5090 Leverkusen Fotografisches farbkupplerhaltiges material
DE3516466C2 (de) * 1985-05-08 1995-03-23 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial mit einem polymeren Gelatineweichmacher
DE3608998A1 (de) * 1986-03-18 1987-10-01 Agfa Gevaert Ag Fotografisches aufzeichnungsmaterial

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DE3740930A1 (de) 1989-06-15
JPH01187550A (ja) 1989-07-26
EP0318799A3 (en) 1990-04-25
EP0318799A2 (fr) 1989-06-07
DE3886364D1 (de) 1994-01-27

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