EP0379893B1 - Matériau de reproduction photographique couleur avec un composé émulsifié générateur de couleur - Google Patents

Matériau de reproduction photographique couleur avec un composé émulsifié générateur de couleur Download PDF

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Publication number
EP0379893B1
EP0379893B1 EP90100495A EP90100495A EP0379893B1 EP 0379893 B1 EP0379893 B1 EP 0379893B1 EP 90100495 A EP90100495 A EP 90100495A EP 90100495 A EP90100495 A EP 90100495A EP 0379893 B1 EP0379893 B1 EP 0379893B1
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EP
European Patent Office
Prior art keywords
compounds
color
layer
recording material
couplers
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Expired - Lifetime
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EP90100495A
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German (de)
English (en)
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EP0379893A3 (en
EP0379893A2 (fr
Inventor
Fritz Dr. Nittel
Helmut Dr. Mäder
Werner Dr. Liebe
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • G03C7/388—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

Definitions

  • the invention relates to a color photographic recording material which, in association with at least one light-sensitive silver halide emulsion layer, contains an emulsified, comparatively hydrophilic coloring compound.
  • Hydrophilic color couplers and other coloring compounds are generally added to the photographic coating solutions in the form of an aqueous or aqueous-alcoholic solution.
  • the required amounts of alkali are used in the preparation of the solutions, provided that the coupler is not already present in water-soluble form as the alkali salt.
  • Hydrophilic color couplers are often characterized by particularly high coupling speeds and are therefore very desirable in the production of highly sensitive color photographic recording materials.
  • When incorporating Hydrophilic compounds from aqueous-alkaline solution in photographic layers have serious disadvantages, insofar as the high salt content in the emulsion caused by the neutralization of the alkaline solutions causes poor flatness and high brittleness of the materials.
  • the casting solutions generally have to be diluted strongly with water in order to compensate for the increase in viscosity caused by the reaction of the sulfo groups or carboxyl groups with the amino groups of the gelatin.
  • this method makes it difficult to produce layers with a desired high packing density on color couplers or other coloring compounds.
  • hydrophobic coloring compounds are used and these are incorporated in an emulsified form into the photographic coating solutions in a known manner using high-boiling organic solvents, so-called oil formers.
  • oil formers are phthalic acid esters, such as dibutyl phthalate or di-n-nonyl phthalate, and phosphoric acid esters, such as tricresyl phosphate; the oil formers mentioned are comparatively hydrophobic and therefore usually very well suited for incorporating hydrophobic substances.
  • the suitability of an oil producer is expressed in that the coloring compound in the relevant oil former has the highest possible solubility and a low tendency to crystallize.
  • Coloring compounds are occasionally used because of their special properties, which in the aforementioned hydrophobic oil formers still have a certain, in many cases still sufficient, but nevertheless reduced solubility and have a clearly hydrophilic character. Such coloring compounds are referred to below as "comparatively hydrophilic".
  • the reduced solubility in the hydrophobic oil formers manifests itself in an increased tendency to crystallize and affects the technical production of the O / W emulsion (oil in water) of the coloring compounds on the one hand, and on the other hand their use in low-binder layers, for example in layers with no more than 40% by weight gelatin, particularly noticeable. If the O / W emulsions are produced on an industrial scale and a co-solvent used is removed rapidly, for example at a rate of more than 30 g / s, crystallization often occurs. In addition, the comparatively hydrophilic coloring compounds mentioned are obviously not sufficiently diffusion-resistant in many cases when using the conventional hydrophobic oil formers, and this disadvantage is particularly evident when used in layers with little binder.
  • the invention has for its object to provide new oil formers for coloring compounds, especially for comparatively hydrophilic coloring compounds. It has now been found that polypropylene oxides with an OH group content of between 1 and 3% by weight are suitable.
  • the present invention relates to a color photographic recording material with at least one silver halide emulsion layer, which is associated with a coloring compound incorporated with the aid of an oil former, characterized in that the oil former contains at least 30% by weight of a polypropylene oxide with an OH content of 1-3 % By weight.
  • the polypropylene oxide used according to the invention as an oil former can be produced by reacting water or monohydric or polyhydric alcohols with propylene oxide (PO), water with about 20-50 times the amount by weight of PO and the alcohol in question, depending on the molecular weight and value, with about 10 - 100 times the molar amount of PO are reacted to set an OH content of 1-3% by weight.
  • PO propylene oxide
  • the molecular weight of the polypropylene oxide a statistical distribution over the entirety of the molecules is generally obtained.
  • Examples of monohydric or polyhydric alcohols to be used are ethanol, propanol, isopropanol, n-butanol, isobutanol, ethylene glycol, 1,2- and 1,3-propylene glycol, glycerol, tetramethylolethane, pentaerythritol, trimethylolpropane.
  • Examples of compounds according to the invention are given below.
  • the molar amount of PO which has been reacted with 1 mol of water or mono- or polyhydric alcohol is given.
  • emulsions of coloring compounds can be produced in a manner known per se.
  • these are generally O / W emulsions (oil-in-water emulsions) in which the oily phase contains the coloring compound to be emulsified, at least one polypropylene oxide (oil former) according to the invention, optionally an auxiliary solvent and further optionally an emulsifying auxiliary, and the aqueous phase usually contains a suitable binder, for example gelatin.
  • the auxiliary solvent is normally removed again in the course of the preparation of the emulsate.
  • the oil former according to the invention can also be used in the form of a mixture.
  • hydrophilic oil formers such as, for example, long-chain aliphatic substituted succinic acid esters of the like, as described for example in DE-A 1 772 192, can also be used.
  • the proportion of polypropylene oxides according to the invention in the total amount of oil former should not be less than 30% by weight.
  • coloring compounds of all kinds can be incorporated into photographic layers. These are generally non-diffusing compounds that can be colored or colorless. Under the conditions of photographic development, a dye is formed from such compounds, either by releasing an optionally pre-formed colored residue as a diffusing dye or by chromogenic coupling with the oxidation product of a color developer. In the latter case, there are color couplers, e.g. Yellow coupler, magenta coupler or cyan coupler.
  • 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 intrinsic color that disappears when the color is coupled or is replaced by the color of the image dye produced (mask coupler), and the white couplers that react with color developer oxidation products yield essentially colorless products.
  • the 2-equivalent couplers also include those couplers which contain a cleavable residue in the coupling site, which is released upon reaction with color developer oxidation products and thereby either directly or after one or more further groups have been cleaved from the primarily cleaved residue (e.g. DE-A-27 03 145, DE-A-28 55 697, DE-A-31 05 026, DE-A-33 19 428), a certain desired photographic activity unfolds, for example as a development inhibitor or accelerator.
  • Examples of such 2-equivalent couplers are the known DIR couplers as well as DAR or. FAR coupler.
  • DIR, DAR or FAR couplers Since with DIR, DAR or FAR couplers the effectiveness of the residue released during coupling is mainly desired and the color-forming properties of these couplers are less important, such DIR, DAR or FAR couplers are also suitable which give essentially colorless products on coupling (DE-A-15 47 640).
  • the cleavable residue can also be a ballast residue, so that upon reaction with color developer oxidation products coupling products are obtained which are diffusible or at least have a weak or restricted mobility (US Pat. No. 4,420,556).
  • the oil formers according to the invention are used with particular advantage to incorporate those compounds which, as explained at the outset, are referred to as "comparatively hydrophilic". These are in particular compounds that contain one or more -SO2-NH groups and / or phenolic hydroxyl groups in their molecule. Examples of such compounds are couplers C-26, M-2, M-8, M-19, M-20, M-21, Y-3, Y-7 and Y-13. By virtue of such groupings, the coloring compounds have an increased solubility in the alkaline processing baths usually used, so that an undesired diffusion into adjacent layers cannot normally be completely prevented during processing. The less binder the individual layers contain, the more this undesirable effect occurs.
  • the comparatively hydrophilic coloring compounds are obviously less soluble in the commonly used hydrophobic oil formers, which manifests itself in an increased tendency to crystallize. If, on the other hand, the comparatively hydrophilic coloring compounds are incorporated with the help of the oil formers according to the invention, then not only the tendency towards crystallization but also the tendency to diffuse is significantly reduced. When using the oil formers according to the invention, it is therefore possible to reduce the proportion by weight of the binder in a layer containing at least one coloring compound and optionally silver halide to 40% or less.
  • color photographic materials are color negative films, color reversal films, color positive films, color photographic paper, color reversal photographic paper, color sensitive materials for the color diffusion transfer process or the silver color bleaching process.
  • Suitable supports for the production of color photographic materials are e.g. Films and foils of semi-synthetic and synthetic polymers such as cellulose nitrate, cellulose acetate, cellulose butyrate, polystyrene, polyvinyl chloride, polyethylene terephthalate and polycarbonate and paper laminated with a baryta layer or ⁇ -olefin polymer layer (e.g. polyethylene).
  • These carriers can be colored with dyes and pigments, for example titanium dioxide. They can also be colored black for the purpose of shielding light.
  • the surface of the support is generally subjected to a treatment in order to improve the adhesion of the photographic emulsion layer, for example a corona discharge with subsequent application of a substrate layer. Layer supports with a light-reflecting surface are preferred.
  • the color photographic materials usually contain at least one red-sensitive, green-sensitive and blue-sensitive silver halide emulsion layer and, if appropriate, intermediate layers and protective layers.
  • Essential constituents of the photographic emulsion layers are binders, light-sensitive silver halide and coloring compounds, eg color couplers.
  • Gelatin is preferably used as the binder. However, this can be replaced in whole or in part by other synthetic, semi-synthetic or naturally occurring polymers.
  • Synthetic gelatin substitutes are, for example, polyvinyl alcohol, poly-N-vinylpyrrolidone, polyacrylamides, polyacrylic acid and their derivatives, in particular their copolymers.
  • Naturally occurring gelatin substitutes are, for example, other proteins such as albumin or casein, cellulose, sugar, starch or alginates.
  • Semi-synthetic gelatin substitutes are usually modified natural products.
  • Cellulose derivatives such as hydroxyalkyl cellulose, carboxymethyl cellulose and phthalyl cellulose and gelatin derivatives, which have been obtained by reaction with alkylating or acylating agents or by grafting on polymerizable monomers, are examples of this.
  • the binders should have a sufficient amount of functional groups so that enough resistant layers can be produced by reaction with suitable hardening agents.
  • functional groups are in particular amino groups, but also carboxyl groups, hydroxyl groups and active methylene groups.
  • the gelatin which is preferably used can be obtained by acidic or alkaline digestion. Oxidized gelatin can also be used. The production such gelatins are described, for example, in The Science and Technology of Gelatine, edited by AG Ward and A. Courts, Academic Press 1977, page 295 ff.
  • the gelatin used in each case should contain the lowest possible level of photographically active impurities (inert gelatin). High viscosity, low swelling gelatins are particularly advantageous.
  • the silver halide present as a light-sensitive component in the photographic material can contain chloride, bromide or iodide or mixtures thereof as the halide.
  • the halide content of at least one layer can consist of 0 to 15 mol% of iodide, 0 to 100 mol% of chloride and 0 to 100 mol% of bromide.
  • silver bromide iodide emulsions are usually used; in the case of color negative and color reversal paper, silver chloride bromide emulsions with a high chloride content are used up to pure silver chloride emulsions.
  • It can be predominantly compact crystals, which are, for example, regularly cubic or octahedral or can have transitional forms.
  • platelet-shaped crystals can preferably also be present, the average ratio of diameter to thickness of which is preferably at least 5: 1, the diameter of a grain being defined as the diameter of a circle with a circle content corresponding to the projected area of the grain.
  • the layers can also have tabular silver halide crystals in which the ratio of diameter to thickness is substantially greater than 5: 1, for example 12: 1 to 30: 1.
  • the silver halide grains can also have a multi-layered grain structure, in the simplest case with an inner and an outer grain area (core / shell), the halide composition and / or other modifications, such as e.g. Doping of the individual grain areas are different.
  • the average grain size of the emulsions is preferably between 0.2 ⁇ m and 2.0 ⁇ m, the grain size distribution can be either homodisperse or heterodisperse. Homodisperse grain size distribution means that 95% of the grains do not deviate from the mean grain size by more than ⁇ 30%.
  • Two or more kinds of silver halide emulsions, which are prepared separately, can be used as a mixture.
  • the photographic emulsions may contain compounds to prevent fogging or to stabilize the photographic function during production, storage or photographic processing.
  • the photographic emulsions can be spectrally sensitized using methine dyes or other dyes.
  • Particularly suitable dyes are cyanine dyes, merocyanine dyes and complex merocyanine dyes.
  • Sensitizers can be dispensed with if the intrinsic sensitivity of the silver halide is sufficient for a certain spectral range, for example the blue sensitivity of silver bromides.
  • the differently sensitized emulsion layers are assigned non-diffusing monomeric or polymeric color couplers, which can be located in the same layer or in a layer adjacent to it.
  • the red-sensitive layers are cyan couplers
  • the green-sensitive layers are magenta couplers
  • the blue-sensitive layers are yellow couplers.
  • the couplers or other compounds can be incorporated into silver halide emulsion layers and other layers in such a way that a solution, a dispersion or an emulsion is first prepared from the compound in question and then added to the casting solution for the layer in question.
  • the selection of the suitable solvent or dispersing agent depends on the solubility of the compound.
  • Hydrophobic compounds can 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.
  • suitable oil formers which can be used in addition to the polypropylene oxides according to the invention are dibutyl phthalate, dicyclohexyl phthalate, di-2-ethylhexyl phthalate, decyl phthalate, triphenyl phosphate, tricresyl phosphate, 2-ethylhexyl diphenyl phosphate, tricyclohexyl phosphate, tri-2-ethylhexyl tri-ethyl-tri-ethylhexyl tri-ethyl-tri-ethyl-tri-ethyl-tri-ethyl-trihydrate, tri-2-ethylhexyl tri-ethyl-tri-ethyl-tri-ethyl-tri-ethylate -2-ethylhexylphenyl phosphate, 2-ethylhexylbenzoate, dodecylbenzoate, 2-ethylbenz
  • 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 and 0 125 522.
  • the photographic recording material can furthermore contain UV light-absorbing compounds, whiteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives for improving the dye, coupler and white stabilization and for reducing the color fog, plasticizers (latices), Contain biocides.
  • 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).
  • Ultraviolet absorbing couplers such as ⁇ -naphthol type cyan couplers
  • ultraviolet absorbing polymers can also be used. These ultraviolet absorbents can be fixed in a special layer by pickling.
  • Filter dyes suitable for visible light include oxonol dyes, hemioxonol dyes, styryl dyes, merocyanine dyes, cyanine dyes and azo dyes. Of these dyes, oxonol dyes, hemioxonol dyes and merocyanine dyes are used particularly advantageously.
  • Suitable whiteners are e.g. in Research Disclosure 17,643 (Dec. 1978), Chapter V, in US-A-2,632,701, 3,269,840 and in GB-A-852,075 and 1,319,763.
  • binder layers in particular the most distant layer from the support, but also occasionally intermediate layers, especially if they are the most distant layer from the support during manufacture, may contain photographically inert particles of inorganic or organic nature, e.g. as a matting agent or as a spacer (DE-A-33 31 542, DE-A-34 24 893, Research Disclosure 17 643, (Dec. 1978), Chapter XVI).
  • photographically inert particles of inorganic or organic nature e.g. as a matting agent or as a spacer (DE-A-33 31 542, DE-A-34 24 893, Research Disclosure 17 643, (Dec. 1978), Chapter XVI).
  • the average particle diameter of the spacers is in particular in the range from 0.2 to 10 ⁇ m.
  • the spacers are water-insoluble and can be alkali-insoluble or alkali-soluble, the alkali-soluble ones generally being removed from the photographic material in the alkaline development bath.
  • suitable polymers are polymethyl methacrylate, copolymers of acrylic acid and methyl methacrylate and hydroxypropyl methyl cellulose hexahydrophthalate.
  • 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 US
  • 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.
  • the last-mentioned curing 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.
  • Coupler emulsions are produced according to the following general emulsification instructions.
  • the oil phase is emulsified into the aqueous phase with a mixed siren. After the addition is complete, the mixture is post-homogenized at 50 bar using a high-pressure homogenizer.
  • auxiliary solvent ethyl acetate
  • solvent evaporator evaporating between 30 and 50 g of ethyl acetate per second.
  • connection W-1 was used as the white coupler.
  • a color photographic recording material was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene.
  • the quantities given relate to 1 m2.
  • the corresponding amounts of AgNO3 are given.
  • the oil formers and yellow couplers used in the blue-sensitive layer are given in Tables 2 and 3.
  • the processing baths were produced according to the following recipes:
  • Table 2 shows the percent yellow secondary density obtained after green exposure, based on a magenta density of 1.0.
  • the relevant value is also given in brackets in the first line, which was obtained for CPM and K-4 with a material which differed only in layer 2 by a gelatin content of 50% by weight. It is clear that when the oil formers according to the invention are used, the gelatin content in layer 2 can be reduced to values below 40% by weight without the yellow secondary density being disadvantageously increased by undesirable diffusion of the yellow coupler into the magenta layer.
  • the percentage magenta density obtained after blue exposure is given.
  • the value given in brackets in the first line means the magenta secondary density of a corresponding material which has a gelatin content of 50% by weight in layer 2. It is again clear that the reduction in the gelatin content in layer 2 also has a disadvantageous effect on the undesirable diffusion of the magenta coupler and that, surprisingly, this disadvantageous effect can be suppressed in the yellow layer when the oil former according to the invention is used.
  • Example 2 Various of the materials defined in Example 2 in connection with Table 2 with the yellow coupler K-4 were exposed and processed and then exposed to a radiation of 1.5 ⁇ 107 lxh in a Xenotest device.
  • the percentage decrease in the yellow density was determined for different initial densities once in the yellow color separation wedge and once in the neutral wedge and is given in Table 4 (values of the neutral wedge in brackets).

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

Claims (6)

  1. Matériau d'enregistrement pour photographie en couleurs, comprenant au moins une couche d'émulsion à l'halogénure d'argent à laquelle est attribué un composé chromogène incorporé à l'aide d'un oléifiant, caractérisé en ce que l'oléifiant est constitué à concurrence d'au moins 30% en poids d'un oxyde de polypropylène ayant une teneur OH de 1 à 3% en poids.
  2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que l'oxyde de propylène est un produit réactionnel d'eau et d'alcools mono- ou polyvalents avec de l'oxyde de propylène.
  3. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que le composé chromogène présente au moins un groupe -SO₂-NH.
  4. Matériau d'enregistrement selon la revendication 3, caractérisé en ce que le composé chromogène est un copulant chromogène.
  5. Matériau d'enregistrement selon la revendication 4, caractérisé en ce que le composé chromogène est un copulant chromogène pour le jaune à deux équivalents.
  6. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que la fraction pondérale du liant dans la couche contenant l'oxyde de polypropylène s'élève à 40% ou moins.
EP90100495A 1989-01-24 1990-01-11 Matériau de reproduction photographique couleur avec un composé émulsifié générateur de couleur Expired - Lifetime EP0379893B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3901903 1989-01-24
DE3901903 1989-01-24

Publications (3)

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EP0379893A2 EP0379893A2 (fr) 1990-08-01
EP0379893A3 EP0379893A3 (en) 1990-12-05
EP0379893B1 true EP0379893B1 (fr) 1994-08-31

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DE (1) DE59006926D1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5491052A (en) * 1992-03-13 1996-02-13 Eastman Kodak Company Yellow layer for color photographic elements
DE69319161T2 (de) * 1992-03-13 1999-02-11 Eastman Kodak Co Gelbschicht für farbphotographisches Papier
US5451497A (en) * 1993-12-30 1995-09-19 Eastman Kodak Company Photographic dispersion having improved stability
US5426019A (en) * 1993-12-30 1995-06-20 Eastman Kodak Company Color photographic element
JPH0854716A (ja) * 1994-08-12 1996-02-27 Konica Corp ハロゲン化銀写真感光材料およびその処理方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1472768A1 (de) * 1965-07-01 1969-03-27 Agfa Gevaert Ag Chemisch sensibilisiertes photographisches Material
JPS5224412B2 (fr) * 1971-08-25 1977-07-01

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EP0379893A3 (en) 1990-12-05
DE59006926D1 (de) 1994-10-06
EP0379893A2 (fr) 1990-08-01

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