EP0422462B1 - Produit d'enregistrement photographique couleur avec des coupleurs libérant des colorants stables à la chaleur - Google Patents

Produit d'enregistrement photographique couleur avec des coupleurs libérant des colorants stables à la chaleur Download PDF

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EP0422462B1
EP0422462B1 EP90118642A EP90118642A EP0422462B1 EP 0422462 B1 EP0422462 B1 EP 0422462B1 EP 90118642 A EP90118642 A EP 90118642A EP 90118642 A EP90118642 A EP 90118642A EP 0422462 B1 EP0422462 B1 EP 0422462B1
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Prior art keywords
coupler
layer
silver halide
halide emulsion
absorption
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EP90118642A
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German (de)
English (en)
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EP0422462A3 (en
EP0422462A2 (fr
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Hans-Joachim Dr. Schumann
Erich Dr. Wolff
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Agfa Gevaert AG
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Agfa Gevaert AG
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—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, multilayer recording material with at least one silver halide emulsion layer with a sensitivity for each of the three main spectral ranges red, green, blue and associated color couplers to form the complementary colored cyan, purple or yellow partial color images, which due to the special structure of the color couplers Image dyes formed in the chromogenic development during normal and especially during MULTICOPY operation of high-performance (scan) printers do not produce a temperature-related color cast in the paper copies.
  • the absorption of the image dyes converts the light energy into thermal energy, which means that the negative used as a template can be warmed up to 45 ° C and more. Filters can be faded in during measurement and exposure, but filters also have residual permeabilities in the filtered out area due to the high radiation power.
  • the radiation power rises sharply from the blue to the red and infrared spectral range (FIG. 1), so that the red-light-absorbing cyan dyes in particular contribute to the heating of the original.
  • the IR heat radiation is expediently removed using a heat protection filter (SCHOTT, Mainz) or eliminated by passing the light beam through a water filter.
  • SCHOTT heat protection filter
  • high-performance (scan) printers only read (scan) the original for a large number of identical copies to determine the exposure time and filtering, and then the corresponding number of copies are printed with this fixed data.
  • the original becomes increasingly warm within a short time during the repeated exposure. This leads to a decrease in density in the original and thus to an increasing overexposure of the copy (color cast).
  • this error does not occur if only one copy is made of the original or in the first copy of a large number of copies which are subsequently made from the same original, but only if one in the original as a result of multiple exposure Warming has occurred.
  • the invention has for its object to provide a color photographic negative recording material from a negative can be produced, the image dyes of which have a better thermal stability and which is consequently more suitable as a template in the production of color copies, in particular in a high-performance (scan) printer.
  • a color photographic negative recording material which contains special cyan couplers which, in the chromogenic development, provide cyan dyes with better thermal stability.
  • the recording material according to the invention is particularly adapted and suitable for processing in high-performance (scan) printers, especially also in multi-copy mode, i.e. if a large number of identical copies are made in succession from the same original.
  • I o or I is the spectral radiation flow in front of or behind the sample.
  • the temperature coefficient a describes the temperature dependence of the absorption A of the absorption band and is the change in absorption ⁇ A per degree, normalized to the absorption A at 23 ° C.
  • the temperature coefficient b describes the temperature dependence of the position ⁇ max of the absorption band and is the spectral change ⁇ ⁇ per degree, normalized to the wavelength ⁇ max at 23 ° C.
  • the importance of the invention lies in the fact that the absorption properties of the image dyes produced in the chromogenic development from the color couplers are largely independent of the ambient temperature within the temperature range of 10 - 60 ° C., so that the copying results are only slightly dependent on a temperature change within the specified range Dimensions are affected. In normal copying, only a few copies, as a rule about 1-3, are made of a negative original, the negative being warmed up only slightly by the copying light.
  • the thermal load on the negative due to the repeated copying exposure in the so-called multicopying operation is considerably greater if the same negative is exposed very often within a short time and the heat generated in this way cannot be dissipated quickly enough.
  • a plurality of copies in the above sense means more than 5, preferably more than 10 and most preferably more than 50.
  • the transparent color negative used as a template in the process of the present invention is prepared by chromogenic development of an imagewise exposed color photographic (negative) recording material which contains the aforementioned cyan, magenta and yellow couplers, at least the cyan coupler used being one for whose dye the condition mentioned applies. This condition preferably also applies to the dyes which are produced from the magenta and yellow couplers used in the chromogenic development.
  • An alkyl group contained on the phenoxy group represented by R 1 is preferably methyl or isopropyl; an alkoxy group is preferably methoxy; a cycloalkyl group is preferably cyclohexyl.
  • Example 1 Examples of cyan couplers according to the invention are listed in Example 1, Table 1 (couplers C-1 to C-8).
  • the coupling residue contained in the pyrazoloazole couplers of the formula IV is, for example, a residue of imidazolo [1,2-b] pyrazole, imidazolo [3,4-b] pyrazole, pyrazolo [2,3-b] pyrazole, pyrazolo [3,2 -c] -1,2,4-triazole, pyrazolo [2,3-b] -1,2,4-triazole, pyrazolo [2,3-c] -1,2,3-triazole or pyrazolo [2, 3-d] tetrazole.
  • the corresponding structures are given below by the formulas IV-1 to IV-7.
  • the substituents R, S, T and U represent hydrogen, alkyl, aralkyl, aryl, alkoxy, aroxy, alkylthio, arylthio, amino, anilino, acylamino, cyano, alkoxycarbonyl, carbamoyl, Sulfamoyl, where these radicals can be further substituted and can contain, for example, a ballast radical.
  • S and T together can also represent a radical to complete a fused-on, optionally substituted benzene ring.
  • the color couplers can be 4-equivalent couplers, but also 2-equivalent couplers.
  • the latter are derived from the 4-equivalent couplers in that they contain a substituent in the coupling point, which is split off during the coupling.
  • the 2-equivalent couplers include those that are colorless, as well as those that have an intense inherent color that disappears when the color is coupled or is replaced by the color of the image dye produced (mask coupler).
  • the color couplers used according to the invention are assigned in the usual way to silver halide emulsion layers with different spectral sensitivity, so that during the chromogenic development of the negative material, complementary-colored partial color images are generated to the color of the exposure light.
  • the couplers or other compounds can be incorporated into the silver halide emulsion layers in such a way that a solution, a dispersion or an emulsion is first prepared by the coupler and then the casting solution for the layer in question is added.
  • the selection of the suitable solvent or dispersing agent depends on the solubility of the compound.
  • Hydrophobic compounds can also be introduced into the casting solution using high-boiling solvents, so-called oil formers. Corresponding methods are described for example in US-A-2 322 027, US-A-2 801 170, US-A-2 801 171 and EP-A-0 043 037.
  • oligomers or polymers instead of the high-boiling solvents or additionally, oligomers or polymers, so-called polymeric oil formers, can be used.
  • the compounds can also be introduced into the casting solution in the form of loaded latices.
  • Suitable oil formers are, for example, alkyl phthalates, phosphonic acid esters, phosphoric acid esters, citric acid esters, benzoic acid esters, amides, fatty acid esters, trimesic acid esters, alcohols, phenols, aniline derivatives and hydrocarbons.
  • oil formers are dibutylphthalate, dicyclohexylphthalate, di-2-ethylhexylphthalate, decylphthalate, triphenylphosphate, tricresylphosphate, 2-ethylhexyldiphenylphosphate, tricyclohexylphosphate, tri-2-ethylhexylphosphate, tridecoxyphosphate, 2-ethylhexylphosphate, tridecoxyphosphate, 2-ethylhexylphosphate, , 2-ethylhexyl p-hydroxybenzoate, diethyldodecanamide, N-tetradecylpyrrolidone, isostearyl alcohol, 2,4-di-t-amylphenol, dioctylacelate, glycerol tributyrate, isostearyl lactate, trioctyl citrate, N, N-octoxy-5-butyl-2-butyl
  • Each of the differently sensitized, light-sensitive layers of the negative material can consist of a single layer or can also comprise two or more silver halide emulsion partial layers (DE-C-1 121 470).
  • red-sensitive silver halide emulsion layers are often arranged closer to the support than green-sensitive silver halide emulsion layers and these are in turn closer than blue-sensitive layers, a non-light-sensitive yellow filter layer generally being located between green-sensitive layers and blue-sensitive layers.
  • the silver halide emulsion layers can contain further additives, in particular, to produce the various partial color images photographically active additives such as antioxidants, white couplers, DIR couplers, DAR couplers, FAR couplers and the like.
  • the non-light-sensitive intermediate layers which are generally arranged between layers of different spectral sensitivity, can contain agents which prevent undesired diffusion of developer oxidation products from one light-sensitive layer into another light-sensitive layer with different spectral sensitization.
  • Suitable agents which are also called scavengers or EOP-catchers, are described in Research Disclosure 17 643 (Dec. 1978), chapters VII, 17 842 (Feb. 1979) and 18 716 (Nov. 1979), page 650 and in EP A-0 069 070, 0 098 072, 0 124 877, 0 125 522.
  • R1, R2 -C8H17-t -C12H25-s -C6H13-t -C8H17-s -C15H31
  • sub-layers of the same spectral sensitization can differ with regard to their composition, in particular with regard to the type and amount of the silver halide grains.
  • the sublayer with higher sensitivity will be located further away from the support than the sublayer with lower sensitivity.
  • Partial layers of the same spectral sensitization can be adjacent to one another or through other layers, for example through Layers of other spectral sensitization must be separated.
  • all highly sensitive and all low-sensitive layers can be combined to form a layer package (DE-A-19 58 709, DE-A-25 30 645, DE-A-26 22 922).
  • the photographic material can also contain UV light-absorbing compounds, whiteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve dye, coupler and white stabilization and to reduce the color fog, plasticizers (latices), Contain biocides and others.
  • Examples are aryl-substituted benzotriazole compounds (US-A-3 533 794), 4-thiazolidone compounds (US-A-3 314 794 and 3 352 681), benzophenone compounds (JP-A-2784/71), cinnamic acid ester compounds (US-A-3 705 805 and 3,707,375), butadiene compounds (US-A-4,045,229) or benzoxazole compounds (US-A-3,700,455).
  • Suitable formalin scavengers include H2N-CONH- (CH2) 2-NH-CONH2,
  • Additives to improve dye, coupler and whiteness stability and to reduce the color fog can belong to the following chemical substance classes: hydroquinones, 6-hydroxychromanes, 5-hydroxycoumarans, spirochromans, spiroindanes , p-alkoxyphenols, sterically hindered phenols, gallic acid derivatives, methylenedioxybenzenes, aminophenols, sterically hindered amines, derivatives with esterified or etherified phenolic hydroxyl groups, metal complexes.
  • the layers of the photographic material can be hardened with the usual hardening agents.
  • Suitable curing agents include formaldehyde, glutaraldehyde and similar aldehyde compounds, diacetyl, cyclopentadione and similar ketone compounds, bis (2-chloroethylurea), 2-hydroxy-4,6-dichloro-1,3,5-triazine and other compounds, the reactive halogen contain (US-A-3 288 775, US-A-2 732 303, GB-A-974 723 and GB-A-1 167 207), divinyl sulfone compounds, 5-acetyl-1,3-diacryloylhexahydro-1,3, 5-triazine and other compounds containing a reactive olefin bond (US-A-3 635 718, US-A-3 232 763 and GB-A-994 869); N-hydroxymethylphthalimide and other N-methylol compounds (US-A-2 732 316 and
  • the hardening can be effected in a known manner by adding the hardening agent to the casting solution for the layer to be hardened, or by overlaying the layer to be hardened with a layer which contains a diffusible hardening agent.
  • Immediate hardeners are understood to mean compounds which crosslink suitable binders in such a way that the hardening is completed to such an extent immediately after casting, at the latest after 24 hours, preferably at the latest after 8 hours, that no further change in the sensitometry and the swelling of the layer structure occurs as a result of the crosslinking reaction .
  • Swelling is understood to mean the difference between the wet film thickness and the dry film thickness during the aqueous processing of the film (Photogr. Sci., Eng. 8 (1964), 275; Photogr. Sci. Eng. (1972), 449).
  • hardening agents which react very quickly with gelatin are, for example, carbamoylpyridinium salts which are able to react with free carboxyl groups of the gelatin, so that the latter react with free amino groups of the gelatin with the formation of peptide bonds and crosslinking of the gelatin.
  • Color photographic negative materials are usually processed by developing, bleaching, fixing and washing or by developing, bleaching, fixing and stabilizing without subsequent washing, whereby bleaching and fixing can be combined into one processing step.
  • All developer compounds which have the ability to react in the form of their oxidation product with color couplers to form azomethine or indophenol dyes can be used as the color developer compound.
  • Suitable color developer compounds are aromatic compounds of the p-phenylenediamine type containing at least one primary amino group, for example N, N-dialkyl-p-phenylenediamines such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methanesulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-ethyl-N-hydroxyethyl) -3-methyl-p-phenylenediamine and 1- (N-ethyl-N-methoxyethyl) -3-methyl-p-phenylenediamine.
  • Other useful color developers are described, for example, in J. Amer. Chem. Soc. 73 , 3106 (1951) and G. Haist, Modern Photographic Processing, 1979, John Wiley and Sons, New York, page 545 ff.
  • bleaching agents e.g. Fe (III) salts and Fe (III) complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes can be used.
  • Iron (III) complexes of aminopolycarboxylic acids are particularly preferred, especially e.g. of ethylenediaminetetraacetic acid, propylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, nitrilotriacetic acid, iminodiacetic acid, N-hydroxyethylethylenediaminetriacetic acid, alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulfates and peroxides e.g. Hydrogen peroxide.
  • the bleach-fixing bath or fixing bath is usually followed by washing, which is designed as countercurrent washing or consists of several tanks with their own water supply.
  • the washing can be completely replaced by a stabilizing bath, which is usually carried out in countercurrent.
  • this stabilizing bath also acts as a final bath.
  • Coupler: DBP: EA: Manoxol 1: 1: 3: 0.1 results.
  • the mixture was then emulsified in 7.5% gelatin solution.
  • the emulsate was stirred at 1000 rpm for 6 min, during which it heated up to approx. 50 ° C. and EA was suctioned off in a water jet vacuum (200-300 mbar).
  • the emulsions thus produced were mixed with a silver bromide iodide emulsion (0.7 mol% iodide) in a ratio of 1 mol coupler: 5.2 mol AgNO3, applied to a layer of cellulose acetate and covered with a protective layer of a 3% gelatin solution, which as Hardening agent contained a carbamoylpyridinium betaine (CAS Reg. No. 65411-60-1). After drying and slicing, the samples thus produced were exposed behind a step wedge and processed in the negative AP 70 process (38 ° C.).
  • Table 1 also shows the measurements of the density decrease in the measuring station (scanning station) of the MSP printer when the original is stationary.
  • the extent of the temperature effect is the slopes ( ⁇ A / ⁇ T) or ( ⁇ / ⁇ T), which are described by the coefficients a and b.
  • a decrease in density of e.g. 0.09 at D 1.37 of the dye CC-1-CD4 is prohibitive in multicopy and recognizable as a clear color cast.
  • the temperature dependency can be described more precisely by means of the absorption measurement, since the measurement is spectral, in contrast to the integral printer measurement. Therefore, the absorption measurements are preferably shown in the following examples.

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Claims (4)

  1. Matériau d'enregistrement pour photographie en couleurs, qui contient, sur un support stratifié transparent, au moins une couche d'émulsion à l'halogénure d'argent sensible au rouge et un copulant pour le bleu-vert du type du naphtol ou du phénol attribué à cette dernière, au moins une couche d'émulsion à l'halogénure d'argent sensible au vert et un copulant magenta du type de la 5-pyrazolone ou du pyrazoloazole attribué à cette dernière, et au moins une couche d'émulsion à l'halogénure d'argent sensible au bleu et un copulant pour le jaune du type de l'acylacétanilide attribué à cette dernière, caractérisé en ce que, pour le colorant bleu-vert formé dans la couche à partir du copulant pour le bleu-vert lors du développement chromogène, en utilisant la 1-(N-éthyl-N-hydroxyéthyl)-3-méthyl-p-phénylènediamine (CD 4) comme révélateur chromogène, il y a lieu de respecter la relation ci-après : a · (1 + b) ≦ 1,5
    Figure imgb0133
     dans laquelle
    a   représente les coefficients de température de l'absorption A (T = 23°C) = 1g I o I
    Figure imgb0134
    Figure imgb0135
     et
    b   les coefficients de température de la longueur d'onde d'absorption λ (T = 23°C)
    Figure imgb0136
  2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que, également pour les colorants d'image formés dans la couche à partir du copulant pour le bleu-vert et à partir du copulant pour le jaune lors du développement chromogène, en utilisant la 1-(N-éthyl-N-hydroxyéthyl)-3-méthyl-p-phénylènediamine (CD 4) comme révélateur chromogène, il y a lieu de respecter les conditions ci-après : a · (1 + b) ≦ 1,5
    Figure imgb0137
     dans laquelle
    a   représente les coefficients de température de l'absorption A (T = 23°C) = 1g I o I
    Figure imgb0138
    Figure imgb0139
     et
    b   les coefficients de température de la longueur d'onde d'absorption λ (T = 23°C)
    Figure imgb0140
  3. Matériau d'enregistrement selon l'une quelconque des revendications 1 et 2, caractérisé en ce que le copulant pour le bleu-vert répond à la formule II ci-après :
    Figure imgb0141
     dans laquelle
    W   représente H ou bien un ou deux autres substituants supplémentaires,
    R¹   représente un groupe phénoxy qui présente, sur le noyau phényle, au moins une position o non substituée et qui peut être substitué en outre avec 1 - 3 substituants choisis parmi le groupe comprenant un groupe alkyle contenant de 1 à 3 atomes de carbone, un groupe alcoxy ou un groupe cycloalkyle;
    R²   représente un groupe alkyle contenant au moins 8 atomes de carbone;
    X   représente H, un atome d'halogène ou encore un groupe qui se sépare lors de la copulation chromogène.
  4. Procédé pour la préparation de plusieurs images positives identiques en couleurs d'un original transparent, de préférence dans une imprimante (scanner) à rendement élevé, dans lequel l'original est balayé (scanné) une fois ligne par ligne pour fixer les données requises d'exposition et de filtrage; après quoi, on expose, avec les données d'exposition et de filtrage ainsi établies, successivement une multitude de sections différentes d'un matériau d'impression pour photographie en couleurs à travers le même original et on le soumet ensuite à un développement chromogène,
    et dans lequel, pour la fabrication de l'original transparent, on utilise un matériau d'enregistrement pour photographie en couleurs qui contient, sur un support stratifié transparent, au moins une couche d'émulsion à l'halogénure d'argent sensible au rouge et un copulant pour le bleu-vert du type du naphtol ou du phénol attribué à cette dernière, au moins une couche d'émulsion à l'halogénure d'argent sensible au vert et un copulant magenta du type de la 5-pyrazolone ou du pyrazoloazole attribué à cette dernière, et au moins une couche d'émulsion à l'halogénure d'argent sensible au bleu et un copulant pour le jaune du type de l'acylacétanilide attribué à cette dernière, et on l'expose en forme d'image de la manière habituelle et ensuite, on le soumet à un développement chromogène,
    caractérisé en ce que, pour le colorant bleu-vert formé dans la couche à partir du copulant pour le bleu-vert lors du développement chromogène, en utilisant la 1-(N-éthyl-N-hydroxyéthyl)-3-méthyl-p-phénylènediamine (CD 4) comme révélateur chromogène, il y a lieu de respecter la relation ci-après : a · (1 + b) ≦ 1,5
    Figure imgb0142
     dans laquelle
    a   représente les coefficients de température de l'absorption A (T = 23°C) = 1g I o I
    Figure imgb0143
    Figure imgb0144
     et
    b   les coefficients de température de la longueur d'onde d'absorption λ (T = 23°C)
    Figure imgb0145
EP90118642A 1989-10-11 1990-09-28 Produit d'enregistrement photographique couleur avec des coupleurs libérant des colorants stables à la chaleur Expired - Lifetime EP0422462B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3933899A DE3933899A1 (de) 1989-10-11 1989-10-11 Farbfotografisches aufzeichnungsmaterial mit farbkupplern, die thermostabile farbstoffe liefern
DE3933899 1989-10-11

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EP0422462A2 EP0422462A2 (fr) 1991-04-17
EP0422462A3 EP0422462A3 (en) 1991-05-22
EP0422462B1 true EP0422462B1 (fr) 1995-09-06

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EP (1) EP0422462B1 (fr)
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Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4333999A (en) * 1979-10-15 1982-06-08 Eastman Kodak Company Cyan dye-forming couplers
DE3273155D1 (en) * 1981-06-11 1986-10-16 Konishiroku Photo Ind Cyan couplers and colour photographic materials containing them
JPS59177553A (ja) * 1983-03-28 1984-10-08 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
DE3580785D1 (de) * 1984-05-10 1991-01-17 Fuji Photo Film Co Ltd Farbphotographisches lichtempfindliches silberhalogenidmaterial.
US4609619A (en) * 1984-09-17 1986-09-02 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide color photographic material
DE3624777A1 (de) * 1986-07-22 1988-01-28 Agfa Gevaert Ag Fotografisches farbkupplerhaltiges material
JPH07122739B2 (ja) * 1987-02-23 1995-12-25 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
JPH0833632B2 (ja) * 1987-04-10 1996-03-29 コニカ株式会社 形成される色素の分光吸収特性が良好なハロゲン化銀写真感光材料
EP0294193A3 (en) * 1987-06-05 1989-02-15 Konica Corporation Apparatus for forming color image, and light-sensitive silver halide color photographic material suited for optical scanning exposure
EP0296854B1 (fr) * 1987-06-24 1993-08-18 Konica Corporation Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière

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DE59009617D1 (de) 1995-10-12
EP0422462A3 (en) 1991-05-22
US5200305A (en) 1993-04-06
DE3933899A1 (de) 1991-04-18
JPH03241344A (ja) 1991-10-28
EP0422462A2 (fr) 1991-04-17

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