EP0560457B1 - Couche jaune pour papier couleur photographique - Google Patents

Couche jaune pour papier couleur photographique Download PDF

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Publication number
EP0560457B1
EP0560457B1 EP19930200701 EP93200701A EP0560457B1 EP 0560457 B1 EP0560457 B1 EP 0560457B1 EP 19930200701 EP19930200701 EP 19930200701 EP 93200701 A EP93200701 A EP 93200701A EP 0560457 B1 EP0560457 B1 EP 0560457B1
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Prior art keywords
coupler
dispersion
yellow
layer
dye
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German (de)
English (en)
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EP0560457A1 (fr
Inventor
James Philip c/o Eastman Kodak Company van Meter
Pranab C/O Eastman Kodak Company Bagchi
Brian c/o Eastman Kodak Company Thomas
Thomas Arthur c/o Eastman Kodak Company Rosiek
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—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 polymer or latex
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/38—Dispersants; Agents facilitating spreading
    • 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
    • G03C2200/00—Details
    • G03C2200/48—Polyoxyethylene

Definitions

  • This invention relates to color photographic elements and to a method of preparing the same. More particularly, it relates to photographic elements containing certain yellow coupler dispersions and silver halide having an unexpected increase in photographic activity of the yellow dispersion and also an unexpected increase of the stability of the developed yellow dye to light fade.
  • Ballasted photographic dye forming couplers are usually incorporated in photographic systems as a colloidal emulsion, usually called a dispersion in the photographic art.
  • the various methods of preparation of photographic coupler dispersions of prior art are illustrated in Figure 1.
  • the coupler is added to a high boiling water immiscible solvent (called a permanent solvent) such as tricresyl phosphate, dibutyl phthalate, etc.
  • a low boiling water miscible solvent such as ethylacetate, propanol, methyl-isobutyl ketone, etc. is also added to promote the solubility of less soluble couplers.
  • the mixture is heated to form a true crystal free solution, called the "coupler solution” as indicated in Figure 1.
  • a second solution of the stabilizing surfactant or surfactants is added to a mixture of gelatin and water and heated to produce a true solution called the "surfactant solution” as indicated in Figure 1.
  • the surfactant used in the "surfactant solution” is usually an anionic surfactant.
  • the "surfactant solution” and the “coupler solution” are then mixed together with mild stirring to form what is known as a “premix”.
  • the premix consists of a crude emulsion of the oil phase (i.e., the "coupler solution") in the aqueous phase (i.e., the "surfactant solution”).
  • the crude “dispersion” is composed of droplets of very large particles, of the order of 5-15 ⁇ m in diameter and is as such not usable for high quality photographic products.
  • dispersions When dispersions are prepared with auxiliary solvents an additional step is necessary to remove the water miscible solvent such that it does not evaporate during the cooling operations to cause excessive evaporation load or create an environmentally hazardous situation.
  • Those dispersions that are treated by some type of an evaporation procedure to remove the auxiliary solvent under a controlled condition are called “evaporated” dispersions.
  • the crude premix can be chill set and noodled by extrusion through orifices and washed by cold water to remove the water soluble auxiliary solvent.
  • Dispersions prepared by this process are usually called “washed” dispersions. Washed dispersions are in general more expensive than evaporated dispersions as they may involve up to 50 hours of tedious washing procedures. Both "washed” and evaporated dispersions lead to dispersion droplets that have broad size distribution with mean diameters ranging between 0.1 to 0.3 ⁇ m. "Washed” and “evaporated” dispersions are usually suitable for low volume film products.
  • U.S. Patent 3,860,425, issued June 14, 1975 to Ono et al teaches the use of a mixture of (1) a nonionic surface active agent containing polyoxypropylene units having a molecular weight greater than 500 and polyoxyethylene units, and at a molar ratio of said polyoxyethylene units to the polyoxypropylene units ranging from 0.1 to 0.6 and (2) an anionic surface active agent having an -OSO 3 M group or an -SO 3 M group, wherein M represents a monovalent cation, and a hydrophobic group in the preparation of a milled dispersion of oleophilic materials, for photographic use.
  • Such dispersions have particle diameters between 0.67 to 0.19 ⁇ m. Between about 0.05 to about 0.10 gram of the anionic surfactant and between about 0.02 gram to about 0.10 gram of the nonionic surfactant per gram of the oleophilic dispersed phase of the coupler are used.
  • U.S. Patent 5,013,640, issued May 7, 1991 to Bagchi et al discloses the use of block oligomeric surfactants comprising hydrophobic polyoxyethylene block (A) and hydrophilic polyoxypropylene block (B) joined in the manner of A-B-A, B-A-B, A-B, (A-B) n ⁇ G ⁇ (B-A) n , a (B-A) ⁇ G ⁇ (A-B) n , where G is a connector organic moiety and n is between 1 and 3, as melt addenda to reduce viscosity of a microprecipitated dispersion melt in gelatin.
  • the said microprecipitated dispersion being preprecipitated as a slurry in water before gelatin addition using preferably an anionic surfactant.
  • the particle size of the microprecipitated dispersions have diameters between 0.01 to 0.05 ⁇ m.
  • EP-A-379893 discloses the use of polypropylene oxides having an OH-content of 1-3 wt% as oil formers for use in preparing dispersions of nondiffusible color providing compounds such as color couplers.
  • the oil formers are disclosed as being prepared by reacting water or an alcohol with propylene oxide so as to attain a statistic distribution of the molecular weight of the polypropylene oxide across the entire molecule (page 2, lines 48-53).
  • Photographic papers contain a layer comprising a UV-absorbing compound dispersed in protective layers to absorb the damaging UV-radiation and prevent it from reaching the image dyes.
  • a UV-absorbing compound dispersed in protective layers to absorb the damaging UV-radiation and prevent it from reaching the image dyes.
  • UV-absorbing compounds have a slight yellow coloration, which when applied in large enough quantities cause the white areas of paper to appear yellow, which is highly undesirable. Therefore, there is a limit to the extent that such UV-absorptive materials can be applied in a photographic product such as paper.
  • Patent 4,656,125 issued April 7, 1987, to Rinner et al discloses that dye stability can be achieved by the addition of stabilizer compounds to the coupler dispersions. A need to enhance the activity of photographic couplers and enhance the stability of image dyes from fade is desired.
  • An object of this invention is to provide more active, (one yielding more dye-density per unit lay down) yellow couplers, dispersed by conventional milling procedures by the simple addition of polyoxyalkylene compounds to the dispersion melt just prior to coating of a photographic product.
  • Another object of the invention is to provide more light-stable yellow dye-forming coupler dispersion melts for quality improvement of photographic products such as color papers and color display materials.
  • Another objective of this invention is to provide a multilayer photographic package, where the bottom slow-developing yellow layer is more active.
  • a color photographic recording element comprising at least one blue-sensitive photographic silver halide emulsion layer comprising dispersed particles having an average diameter of 0.1 to 0.3 ⁇ m and being other than microprecipitated particles, and comprising a yellow image-dye forming pivalylacetanilide coupler, characterized in that the emulsion layer further comprises from about 0.1 to about 0.6 gram of a polyoxyalkylene polymer, per gram of the yellow coupler, wherein the polyoxyalkylene polymer is a non-aromatic polyoxyethylene-polyoxypropylene block co-polymer having at least two terminal hydroxy groups.
  • the polyoxyalkylene polymer is present in the amount of from about 0.1 to about 0.3 gram per gram of yellow coupler.
  • R2 is arylsulfonyl, it may be substituted, for example, with PhOCH 2 PhOH or NHCH 2 CH 2 OH.
  • Ballasting groups usually comprise one or more 5 to 25 carbon atom containing organic moiety whose function is to immobilize the coupler and the formed image dye during photographic development by imparting poor water diffusibility to the coupler compound.
  • Kodachrome® type couplers are unballasted and therefore are soluble in developer solutions. Such couplers are usually incorporated in the developer solutions.
  • Fisher couplers usually contain a solubilizing -SO 3 - group to impart base solubilizing characteristics to the coupler molecule.
  • the ballast is the polymer backbone which may also be gelatin.
  • ballasting polymeric backbone is achieved through the coupling off group rendering the formed dye more mobile and transferable by diffusion or by thermal evaporation after photographic development.
  • a broad description of such coupler compounds can be found in "The Theory of the Photographic Process", 4th Edition, McMillan, New York, 1977 by T.H. James.
  • Typical ballast group -Y- are extensively described in US 3,770,446 (1973), US 3,265,506 (1966) etc. and are hereby incorporated herein by reference.
  • ballast groups that can be used are disclosed in US patents 2,875,057; 2,407,210; 2,298,443; 3,048,194; 4,022,620; 4,443,536 and 3,447,928, which are also included herein by reference.
  • the invention is carried out by adding required amounts of the polymeric polyoxyalkylene surface active compound and preferably a surface active compound comprising at least a polyoxypropylene (POP) block and a polyethylene (POE) block to the dispersion melts, prepared by conventional milling procedure prior to coating the film product.
  • POP polyoxypropylene
  • POE polyethylene
  • a method of preparing a blue sensitive layer in a silver halide photographic light sensitive element which comprises forming a dispersion of a yellow image dye-forming coupler having particles with an average diameter of 0.1 to 0.3 ⁇ m, in a hydrophilic colloid, mixing the dispersion with a silver halide emulsion and applying the resulting composition to form a layer, characterized in that the yellow coupler is a pivalylacetanilide coupler and the method further comprises the step of adding a polyoxyalkylene polymer to the dispersion or the emulsion in the amount of from about 0.1 to 0.6 gram per gram of yellow coupler in the dispersion prior to forming the layer.
  • the surfactant used to prepare the surfactant solution of Fig. 1 is any surfactant that will aid the formation of stable dispersions of particles.
  • Such surfactants for the preparation of the dispersion can be anionic and are in general defined as follows:
  • the anionic dispersion surfactants of this invention comprise a 6 to 25 carbon atom hydrophobic moiety made up of either aliphatic, aromatic or of both types of hydrocarbons, or fluorocarbon groups terminated by single or multiple anionic charges arising from -COO - , -SO 3 - or -OSO 3 - groups or a combination thereof.
  • Such surfactants for the preparation of the dispersions can also be polyether surfactants definable as follows:
  • the polyether dispersion surfactants of this invention comprise a 6 to 25 carbon atom hydrophobic moiety made up of either aliphatic, aromatic or of both types of hydrocarbon or fluorocarbon groups and at least 2 oxyethylene and/or glycidyl ether groups that may or may not be terminated with a single or multiple negative change arising from -COO - , -0SO 3 - ,or -OSO 4 - groups or a combination thereof.
  • Class-B Polyether Dispersion Surfactants are as follows: DS-B5 n-C 12 H 25 ⁇ O ⁇ (CH 2 -CH 2 -O) 23 -OH (Trycol 5964, Henkel)
  • Such surfactants for the preparation of the dispersion can also be sugar surfactants defined as follows:
  • the sugar dispersion surfactants of this invention are characterized by having one to three hydrophobic tails, each tail containing from about 6 to 25 carbon atoms comprising either aliphatic, aromatic or a combination of both types of hydrocarbon or fluorocarbon groups and also having one or more attached hydrophilic mono- or oligosacharidic hydrophilic chains that may or may not be terminated by single or multiple anionic charges arising from -COO - , -OSO - 3 or -SO - 3 groups or a combination thereof.
  • the dispersion surfactant or surfactants can be used by themselves or as any combination of mixtures of different classes or different individual surfactants at a level performing between about 0.03g to about 0.lg of total surfactant, as a single surfactant or in combination for the preparation of the dispersion per g of the coupler to be dispersed.
  • the preferred surfactant is Alkanol-XC (DS-A11).
  • the couplers of this invention are yellow-dye forming pivalylacetanilide (PAA) couplers of general structure as indicated earlier. Specific examples of such class of couplers are as follows:
  • Suitable surface active polyoxyalkylene polymers and preferably block polymeric compounds containing polyoxyethylene and polyoxypropylene blocks or block polymers with multiple polyoxyethylene-polyoxypropylene blocks connected together by an organic moiety that impart high activity and high dye-stability when added to a silver halide gelatino coating melt containing conventionally predispersed PAA couplers of this invention, are given to Table I.
  • the block polymeric addenda of this invention is added to a coating melt to the extent of 0.1 to 0.6g per gram of the PAA coupler of this invention.
  • the preferred amount is between 0.1 to 0.3g of the block polymeric compound per gram of the PAA coupler.
  • the preferred block polymeric materials of this invention are (P-1) through (P-6).
  • Particularly preferred are polyoxyalkylene polymers of the formula: or where a has a value of 5 to 500 and, b has a value of 5 to 500.
  • Pluronic L44 which has the following structure.
  • This invention is very specific to couplers of the PAA class.
  • the addition of the surface active materials of this invention produce no activity advantage or dye stability advantage to other couplers.
  • the noninventive coupler combinations with the surface active addenda of this invention exemplified hereinafter are as follows:
  • nonionic surface active materials show this unique simultaneous effect of increased activity and added dye stability.
  • the noninventive, nonionic surfactant used in this example is the alkyl polyglycoside (APG-225), which has the following structure.
  • Dye stabilizers and associated scavengers used in preparation of these dispersions are as follows:
  • UV-absorbing compounds used in the layers over the sensitized layers are as follows:
  • the coating format for testing these PAA-yellow couplers, from the base up is as follows:
  • Example 9 Extraction of the dye from the coatings and determination of their yield with a known extinction coefficient of the dye for the two invention Examples 9 and 10 are also shown in Table III in comparison with the control Example 8. It is seen that in Example 9 there is about a 46% and in Example 10 about 60% increased dye yield. The addition of L44 increased the dye yield for coupler (CY-1). APG 225 which is also a nonionic amphiphile did not show any increase in dye density (Table III). The actual sensitometric curves of the control Example 8 and the invention Examples 9 and 10 are also shown in Fig. 2, where it is seen that the spiking of L44 produces a very large boost in the Dmax of the coating of PAA coupler (CY-1). It is also seen that the boost in activity is nonlinear.
  • Fig. 3 shows plots of the dye density yield vs silver formed in the step wedge image as measured by x-ray fluorescence, after fixing out the Ag halide following the color development step.
  • the invention examples show larger dye density for the same amount of silver developed in comparison to the control coatings.
  • Another advantage of this invention is high dye stability of the formed dye image. This was demonstrated by exposing the images for 2 and 4 weeks to high intensity (50 K Lux) light balanced to the color temperature of sunshine under ambient humidity and temperature conditions. The density losses measured from a density of 1.7 are also listed in Table III. It is observed that in the inventive Examples 9 and 10 where L44 was present dye density losses were considerably smaller compared to the control Example 8 and the noninventive Example 11 which contained the noninventive material APG 224. It is observed that control Example 8 did not contain any L44.
  • the coating format for testing yellow coupler (CY-2), from the base up, is as follows:
  • the spreading agent Olin 10G was used at a level of 0.3% of the melt volume of each layer.
  • the coating format for testing magenta coupler (C-1), from base up is as follows:
  • the spreading agent Olin 10G was used at a level of 0.3% of the melt volume of each layer.
  • the coating format for testing magenta coupler (C-2), from base up is as follows:
  • the spreading agent Olin 10G was used at a level of 0.3% of the melt volume of each layer.
  • the coating format for testing cyan coupler (C-3), from base up is as follows:
  • the spreading agent Olin 10G was used at a level of 0.3% of the melt volume of each layer.
  • the coating format for testing cyan coupler (C-4), from base up is as follows:
  • a typical full multilayer photographic element in accordance with this invention has the following configuration: (Numbers indicate coverage in mg per square ft.) (Numbers within " " indicate same in mg per square meter) LAYER 7 Overcoat: 125.0 Gelatin; "1336" 2.0 (ST-3) (Conventional Scavenger Dispersed in Solvent); "21” LAYER 6 UV Protection Layer: 61.0 Gelatin; “653” 34.3 Tinuvin 328 (Co-dispersed) Ultraviolet light absorber; “364" 5.7 Tinuvin 326 (Co-dispersed) Ultraviolet light absorber; "60” 4.0 (ST-3) (Co-dispersed in Solvent); "43” LAYER 5 Red Layer: 115.0 Gelatin; "1230” 39.3 (C-3) (Cyan Cplr.

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Claims (9)

  1. Elément d'enregistrement photographique couleur comprenant au moins une couche d'émulsion photographique aux halogénures d'argent sensible au bleu comprenant des particules dispersées ayant un diamètre moyen compris entre 0,1 et 0,3 µm, autres que des particules microprécipitées, et comprenant un coupleur pivalylacétanilide formateur de colorant d'image jaune, caractérisé en ce que la couche d'émulsion comprend aussi 0,1 à 0,6 gramme environ d'un polymère de polyoxyalkylène par gramme de coupleur jaune, dans lequel le polymère de polyoxyalkylène est un copolymère séquence non aromatique de polyoxyéthylène et de polyoxypropylène ayant au moins deux groupes hydroxy terminaux.
  2. Elément d'enregistrement photographique couleur selon la revendication 1, dans lequel le polymère de polyoxyalkylène est présent à une concentration comprise entre 0,1 et 0,3 gramme environ par gramme de coupleur jaune.
  3. Elément d'enregistrement photographique couleur selon la revendication 1, dans lequel la dispersion de coupleur formateur de colorant d'image jaune contient un solvant de coupleur.
  4. Elément d'enregistrement photographique couleur selon la revendication 1, dans lequel le polymère de polyoxyalkylène est
    Figure 00530001
    Figure 00530002
    où la valeur de a est comprise entre 5 et 500 et la valeur de b est comprise entre 5 et 500.
  5. Elément d'enregistrement photographique couleur selon l'une quelconque des revendications précédentes, dans lequel le coupleur jaune répond à la formule : où X est un hydrogène ou un groupe qui se sépare au couplage, et Y est un groupe ballast.
  6. Elément d'enregistrement photographique couleur selon la revendication 5, dans lequel X représente -H, -Cl, -OCOR1, -SAr, -SO2R1, -OSO2R1,
    Figure 00540002
    où R1 représente un groupe alkyle ; R2 représente un groupe alkyle ou un groupe arylsulfonyle, alkoxycarbonyle, alkylsulfonamido ou carboxyle éventuellement substitué ; R3 représente un hydrogène ou un groupe alkylsulfonamido ; Ar représente un groupe aryle'; et Z représente n'importe quel groupe organique permettant de compléter le cycle.
  7. Procédé de préparation d'une couche sensible au bleu dans un élément photographique photosensible aux halogénures d'argent, qui comprend la formation d'une dispersion d'un coupleur formateur de colorant d'image jaune dans un colloïde hydrophile, le mélange de la dispersion avec une émulsion aux halogénures d'argent et l'application de la composition résultante pour former une couche, procédé caractérisé en ce que le coupleur jaune est un coupleur pivalylacétanilide et le procédé comprend aussi une étape d'addition d'un polymère de polyoxyalkylène à la dispersion ou à l'émulsion, en une quantité comprise entre 0,1 et 0,6 gramme environ par gramme de coupleur jaune contenu dans la dispersion, avant de former la couche.
  8. Procédé selon la revendication 7, dans lequel le polymère de polyoxyalkylène est un copolymère séquencé de polyoxyéthylène et de polyoxypropylène.
  9. Procédé selon la revendication 7 ou 8, dans lequel le coupleur jaune est tel que défini dans la revendication 5 ou 6.
EP19930200701 1992-03-13 1993-03-11 Couche jaune pour papier couleur photographique Expired - Lifetime EP0560457B1 (fr)

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DE69421257T2 (de) * 1993-12-30 2000-05-31 Eastman Kodak Co., Rochester Farbphotographisches Element
EP0674221B1 (fr) * 1994-02-18 1998-08-26 Kodak Limited Agents tensioactifs et compositions colloidales hydrophiles et matériaux les contenant
US5484695A (en) * 1994-02-18 1996-01-16 Eastman Kodak Company Surfactants and hydrophilic colloid compositions and materials containing them
GB2303626B (en) * 1995-07-25 1998-12-09 Kodak Ltd Surfactants and hydrophilic colloid compositions and materials containing them

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JPS5224412B2 (fr) * 1971-08-25 1977-07-01
DE59006926D1 (de) * 1989-01-24 1994-10-06 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial mit einer emulgierten farbgebenden Verbindung.
US5013640A (en) * 1989-06-15 1991-05-07 Eastman Kodak Company Preparation of low viscosity small-particle photographic dispersions in gelatin

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