EP0011051A2 - Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs - Google Patents

Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs Download PDF

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Publication number
EP0011051A2
EP0011051A2 EP79810141A EP79810141A EP0011051A2 EP 0011051 A2 EP0011051 A2 EP 0011051A2 EP 79810141 A EP79810141 A EP 79810141A EP 79810141 A EP79810141 A EP 79810141A EP 0011051 A2 EP0011051 A2 EP 0011051A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
color photographic
light
recording material
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.)
Granted
Application number
EP79810141A
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German (de)
English (en)
Other versions
EP0011051A3 (en
EP0011051B1 (fr
Inventor
David G. Dr. Leppard
Michael Dr. Rasberger
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0011051A2 publication Critical patent/EP0011051A2/fr
Publication of EP0011051A3 publication Critical patent/EP0011051A3/xx
Application granted granted Critical
Publication of EP0011051B1 publication Critical patent/EP0011051B1/fr
Expired 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
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/3924—Heterocyclic
    • G03C7/39244—Heterocyclic the nucleus containing only nitrogen as hetero atoms
    • G03C7/39248—Heterocyclic the nucleus containing only nitrogen as hetero atoms one nitrogen atom

Definitions

  • the present invention relates to a color photographic recording material which contains at least one light stabilizer in at least one light-sensitive silver halide emulsion layer and / or in at least one of the customary auxiliary layers.
  • color photographic recording materials which contain color couplers in light-sensitive silver halide emulsion layers are known to be exposed and developed with an aromatic developer containing primary amino groups.
  • the oxidized developer substance then reacts with the color coupler to form an image dye, the amount of which depends on the amount of incident light.
  • a multilayer photographic light-sensitive material is used which consists of a red-sensitive layer containing the cyan coupler, a green-sensitive layer containing the magenta coupler, and a blue-sensitive layer which in turn contains the yellow coupler.
  • the corresponding dyes with the colors blue-green, purple and yellow are created.
  • Phenols or a-naphthols are usually used as cyan couplers, pyrazolones as magenta couplers and acylacetylamides as yellow couplers.
  • the dyes formed after development are accordingly indophenols, indamines or azomethines.
  • the ultraviolet absorbers In order to achieve adequate light protection, however, relatively large amounts of the ultraviolet absorbers must be used, which generally has the consequence that the thickness of the photographic layers into which the ultraviolet absorbers are incorporated must be increased. Such a measure is highly undesirable for the photographic properties of the material. In addition, the ultraviolet absorbers do not provide effective protection against fading of color images by visible light.
  • Another disadvantage of using relatively large amounts of ultraviolet absorbers is that large amounts of solvent are required in order to achieve the desired fine distribution of these compounds in the aqueous binder emulsions. If concentrated solutions of the ultraviolet absorbers are used, there is a risk that they will become uncontrolled when incorporated into the binder emulsions, ie not in the separate the desired fine distribution and so uniform protection against ultraviolet radiation cannot be achieved.
  • the present invention therefore relates to a color photographic recording material which contains at least one piperidine compound as light stabilizer in at least one light-sensitive silver halide emulsion layer, an intermediate layer and / or a protective layer, characterized in that the piperidine compound of the formula in which R 1 is hydrogen or alkyl having 1 to 4 carbon atoms, R 2 is alkyl or hydroxyalkyl each having 1 to 12 carbon atoms, alkenyl or alkynyl having 3 or 4 carbon atoms, benzyl or R6CO-, in which R 6 is hydrogen, alkyl having 1 up to 12 carbon atoms, alkenyl with 2 or 3 carbon atoms, chloromethyl, cyclohexyl, benzyl or optionally substituted phenyl or phenylethyl with two alkyl groups each with 1 to 4 carbon atoms and a hydroxyl group, R 3 is hydrogen or methyl, R 4 and R 5 per alkyl with 1 to 5 carbon atoms or cycl
  • the light stabilizers can also be used in combination with conventional ultraviolet absorbers.
  • the present invention furthermore relates to a process for stabilizing color photographic recording materials by incorporating at least one light stabilizer of the formula (1), if appropriate in combination with an ultraviolet absorber, into at least one light-sensitive and / or auxiliary layer of the material, a process for the preparation of the harmful action light-stabilized color photographic images by imagewise exposure and color development of the aforementioned recording materials and the color photographic images thus obtained.
  • R 1 is alkyl with 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl or n-butyl. Ethyl and especially methyl are preferred.
  • R 2 is alkyl having 1 to 12 carbon atoms
  • primary alkyl groups such as those mentioned above, as well as, for example, n-amyl, n-hexyl, n-octyl, n-nonyl, n-decyl or n-dodecyl are generally suitable.
  • the analogous residues apply to hydroxyalkyl.
  • R 2 in the meaning alkenyl or alkynyl with 3 or 4 carbons can be, for example, allyl, methallyl or propargyl.
  • R 2 are alkyl or hydroxyalkyl each having 1 to 4 carbon atoms, alkenyl or alkynyl having 3 or 4 carbon atoms, benzyl and also acyl, where formyl, acetyl, propionyl, acrylyl, methacrylyl, crotonyl, benzoyl or benzylcarbonyl can be mentioned.
  • R 3 is hydrogen or methyl.
  • R 4 and R 5 are each alkyl having 1 to 5 carbon atoms, the primary alkyl radicals already mentioned above, and also secondary and tertiary alkyl groups, such as isopropyl, isobutyl or tert. Butyl are suitable.
  • R 4 and R 5 are also cycloalkyl having 5 to 8 carbon atoms, such as, in particular, in particular cyclopentyl and cyclohexyl.
  • Preferred meanings of R 4 and R are alkyl having 1 to 4 carbon atoms, in particular methyl and tert. Butyl.
  • the substituent Y as an optionally present substituent on the central carbon atom in the compounds of the formula (1) can be hydrogen, straight-chain or branched alkyl having 1 to 12 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, n-amyl, n-hexyl, n- and iso-heptyl, n-octyl, n-nonyl, n-decyl, n-jndecyl or Dodecyl and the corresponding isomers.
  • Y has the meaning - (CH 2 ) q COOR 7 , in which q is 0 or an integer from 1 to 10, hydrogen, methyl or ethyl are suitable for R 7 .
  • R 8 is methyl or ethyl, furthermore phenyl or benzyl; Y is also cyan, benzyl or a radical of the formulas (la) or (1b); wherein the substituents have the meanings given.
  • the substituent R 9 in the formula (Ib) has the meaning hydrogen, methyl or ethyl.
  • Color photographic recording materials which have at least one compound of the formula as light stabilizers are now preferred contain, wherein R 10 is methyl, ethyl, benzyl, acetyl, acrylyl, methacrylyl, crotonyl, allyl or propargyl.
  • the compounds of the formulas (1) to ( 31 ) are known compounds which are described, for example, in DE-OS 2 456 364, 2 647 452, 2 654 058 and 2 656 76 9 .
  • the compounds can be prepared by various methods, with several reaction steps generally being required.
  • Starting materials for the first reaction stage are, for example, malonic acid or one of its reactive derivatives, such as the di ' alkyl esters, and 4-hydroxy- or 4-aminopiperidines, the substituents (R 2 ) on the nitrogen atom of the piperidine ring already in the molecule can be present or can be introduced into the molecule in a later N-alkylation or N-acylation step by customary methods.
  • Suitable alkylating or acylating agents are, for example, alkyl halides, alkenyl halides, propargyl chloride, benzyl chloride or carboxylic acid chlorides, which are preferably reacted with the piperidine derivative in the presence of molar amounts of a base. Hydroxyalkyl residues are introduced into the molecule by reaction with epoxides, for example ethylene oxide or propylene oxide.
  • the compounds of formula (1) can either be introduced first with the hydroxybenzyl substituent and then with the substituent Y or - preferably - first with the substituent Y and then with the hydroxybenzyl group.
  • the hydroxybenzyl group can be introduced by reaction with an alkyl-substituted hydroxybenzyldithiocarbamate of the formula HO-benzyl-S-CS-N (R ") 2 , where R" is an alkyl group having 1 to 5 carbon atoms or both groups R "together with the nitrogen represent a morpholine, pyrrolidine or piperidine ring.
  • R " is an alkyl group having 1 to 5 carbon atoms or both groups R "together with the nitrogen represent a morpholine, pyrrolidine or piperidine ring.
  • dithiocarbamates can be obtained by reacting a phenol with formaldehyde, carbon disulfide and a secondary amine.
  • substituent Y is present in the compounds of the formulas (1) and (2), it can be introduced into the molecule by the known methods of C-alkylation of activated methylene compounds.
  • the compounds of formulas (1) and (2) are hardly soluble in water, and therefore they are in a low boiling organic solvent such as methyl acetate, ethyl acetate, carbon tetrachloride, chloroform, methanol, ethanol, n- h utanol, dioxane, acetone or benzene , a high-boiling organic solvent, such as tricresyl phosphate, dimethylformamide, dimethyl sulfoxide, di-n-butyl phthalate or ethyl-N-diphenylcarbamate, or a solvent mixture of the above-mentioned low-boiling and high-boiling organic solvents, the solution obtained becomes a protective colloid solution, in particular an aqueous gelatin solution and dispersed by means of a colloid mill of a homogenizer or by using ultrasound.
  • a protective colloid solution in particular an aqueous gelatin solution and dispersed by means of
  • the dispersions thus obtained are then used to produce the layers of color photographic recording materials (for example film, paper or silver color bleaching materials).
  • These layers can, for example, be intermediate or protective layers, but in particular light-sensitive (blue and red-sensitive) silver halide emulsion layers, in which the cyan, cyan, magenta and yellow dyes are formed from the corresponding color couplers during the development of the exposed recording material will.
  • ultraviolet absorbers are also used, they are located in the same layers, but preferably in the intermediate or protective layers.
  • the light stabilizer can also be applied in the treatment baths that are used after the color development, e.g. in fixing and / or washing baths, although a certain solubility of the compounds of the formula (1) in alcohols, (methanol / ethanol) aqueous alkali and / or water is required.
  • the light stabilizer can be incorporated not only into the usual photographic emulsion layers, but also into a receiving layer.
  • Any cyan, purple and yellow couplers that are used to form the dyes mentioned and thus the color images can be used. You can e.g. be dissolved in an alkaline solution or in a high-boiling organic solvent, these solutions then being dispersed in an aqueous gelatin solution and incorporated into a photographic silver halide emulsion.
  • the silver halide emulsions preferably contain gelatin as a binder, optionally in a mixture with other high-molecular natural or synthetic compounds.
  • the silver halide emulsions can for example be silver bromide, silver chloride or silver iodide emulsions or also those emulsions which contain a mixture of silver halides, e.g. Silver bromide-iodide or silver chloride-bromide emulsions.
  • the emulsions can be chemically sensitized, they can also contain conventional organic stabilizers and antifoggants and also conventional plasticizers, such as e.g. Glycerin.
  • the emulsions can also be hardened with the hardeners customary for gelatin.
  • the emulsions may also contain conventional casting aids.
  • the emulsions can be applied to conventional supports for photographic recording material.
  • the usual developer baths can be used to develop the color photographic recording material. These typically contain a p-phenylenediamine type developer, a development retardant such as potassium bromide, an antioxidant such as sodium sulfite and a base e.g. an alkali hydroxide or alkali carbonate.
  • the developing baths may also contain a conventional antifoggant and complexing agent.
  • the amount of the light stabilizer can vary within wide limits and is approximately in the range from 1 to 500 mg, preferably 1 to 300 and in particular 200 mg per m 2 of the layer into which it (they) is (are) incorporated.
  • the ultraviolet absorber can be present together with the light stabilizer in one layer or in an adjacent layer.
  • the weight ratio between a conventional ultraviolet absorber and the light stabilizer of the formula (1) is approximately (5-10): 1, the molar ratio approximately (10-20): 1.
  • Examples of ultraviolet absorbers are e.g. Compounds of the benzophenone, acrylonitrile, thiazolidone, benztriazole, oxazole, thiazole and imidazole type.
  • the color images obtained with the recording material according to the invention by exposure and development show a clearly improved light fastness to visible and ultraviolet light.
  • the compounds of formula (1) are practically colorless, so that there is no discoloration of the images; in addition, they are well compatible with the usual photographic additives present in the individual layers; Because of their good effectiveness, their use amount can be reduced and thus their precipitation or crystallization is avoided if they are incorporated as an organic solution in the aqueous binder emulsions used for the production of photographic layers.
  • the individual processing steps required to produce the color images after exposure of the photographic recording material are not adversely affected by the light stabilizers. Furthermore, the so-called pressure fog formation that frequently occurs with blue-sensitive emulsions can be largely suppressed. This can e.g.
  • 7.0 ml of 6% gelatin solution and 0.5 ml of an 8% solution of the wetting agent of the formula are added in isopropanol / water (3: 4) and 0.5 ml of water, then emulsified with the aid of an ultrasound device and with a power of 100 watts, for 5 minutes 2.5 ml of freshly sonicated coupler additive emulsion, 0.8 ml of silver bromide emulsion containing 2.8% silver, 0.7 ml of a 1% aqueous solution of the hardener of the formula 0.4 ml of a 1.5% aqueous gelatin solution and 4.0 ml of water are mixed together, adjusted to a pH of 6.5 and poured onto a substrate glass plate of 13x18 cm format at 40 ° C. After the layer has solidified at 10 ° C., the plate is dried in a drying cabinet with circulating air at room temperature.
  • a strip of the coated glass plate cut to a format of 4.0 cm x 6.5 cm is exposed to 500 lux for 6 seconds under a step wedge and then processed at 32.8 ° C ( ⁇ 0.3 ° C) as follows:
  • the developer bath has the following composition:
  • the pH is 10.1.
  • a conventional bath which has the following composition, for example, serves as the bleach-fix bath.
  • the step wedge obtained in this way is irradiated in an Atlas device (lamp 2500 W) with 10,000 Langley units each, with and without an ultraviolet filter (Kodak filter 2C).
  • the data show the good protection of the photographic material against the harmful influence of light, which can be achieved when using the light stabilizers used according to the invention.
  • the effects are significantly improved compared to those that can be achieved with known light stabilizers already used in photographic materials.
  • Good results are also achieved with the compounds of the formulas (4), (6), (8) to (22) and (24) to (3 1 ).
  • 0.4 ml of 1.5% aqueous gelatin solution and 4.0 ml of water are mixed with one another, adjusted to a pH of 6.5 and poured at 40 ° C. onto a 13 x 18 cm format glass plate. After the layer has solidified at 10 ° C., the plate is dried in a drying cabinet with ambient air at room temperature.
  • a strip of the coated glass plate cut to a format of 4.0 cm ⁇ 6.5 cm is exposed under a step wedge at 500 lux for 6 seconds and then at 32.8 ° C. ( ⁇ 0.3 ° C.) as in Example 1 described processed.
  • a clear, sharp, blue-green colored step wedge is obtained with an absorption maximum at 653 nm and a maximum density of 1.10.
  • step wedge and step wedges produced analogously, which were produced using the compounds (105) to (110), are exposed and measured as described in Example 1. Table 2 contains the results.
  • Analog other photographic materials are prepared, each dissolved in addition to the color coupler ol light stabilizers in amounts of 0,7.10 -3 M and 1.4 x 10 -3 mol per m 2 in Essigester contain.
  • Gelatin solutions are prepared as in Example 1, but the light stabilizers of the formulas (23) (according to the invention) and (105) and (106) (comparison) and the yellow coupler of the formula are used or the formula (DE-OS 2 757 380).
  • the light stabilizers and the yellow couplers are used in a molar ratio of 1: 1.
  • Example 1 The production of the coated glass plates, the exposure and photographic processing and the light fastness test are carried out as in Example 1.
  • the light fastness test is carried out with an irradiation of 15,000 Langley units.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Hydrogenated Pyridines (AREA)
EP79810141A 1978-11-06 1979-10-31 Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs Expired EP0011051B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1139678 1978-11-06
CH11396/78 1978-11-06

Publications (3)

Publication Number Publication Date
EP0011051A2 true EP0011051A2 (fr) 1980-05-14
EP0011051A3 EP0011051A3 (en) 1980-05-28
EP0011051B1 EP0011051B1 (fr) 1982-09-15

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EP79810141A Expired EP0011051B1 (fr) 1978-11-06 1979-10-31 Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs

Country Status (5)

Country Link
US (1) US4268593A (fr)
EP (1) EP0011051B1 (fr)
JP (1) JPS5565954A (fr)
CA (1) CA1145605A (fr)
DE (1) DE2963689D1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082817A1 (fr) * 1981-12-17 1983-06-29 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0103540A1 (fr) * 1982-08-18 1984-03-21 Ciba-Geigy Ag Matériel d'enregistrement photographique en couleurs
EP0109937A2 (fr) * 1982-11-18 1984-05-30 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0110828A2 (fr) * 1982-11-26 1984-06-13 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0111448A2 (fr) * 1982-12-08 1984-06-20 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0111447A2 (fr) * 1982-12-03 1984-06-20 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0112802A2 (fr) * 1982-12-16 1984-07-04 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0113124A2 (fr) * 1982-12-30 1984-07-11 Konica Corporation Matériel photographique à l'halogénure d'argent sensible à la lumière
EP0114029A2 (fr) * 1982-12-16 1984-07-25 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0114028A2 (fr) * 1982-12-16 1984-07-25 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0104146B1 (fr) * 1982-09-21 1986-07-30 Ciba-Geigy Ag Matériau d'enregistrement photographique couleur

Families Citing this family (15)

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Publication number Priority date Publication date Assignee Title
JPS58102231A (ja) * 1981-12-14 1983-06-17 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS60222853A (ja) * 1984-04-20 1985-11-07 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
EP0203746B2 (fr) * 1985-05-11 1994-08-24 Konica Corporation Matériau photographique à l'halogénure d'argent sensible à la lumière
US4728599A (en) * 1985-12-02 1988-03-01 Eastman Kodak Company Sterically hindered phenolic ester photographic coupler dispersion addenda and photographic elements employing same
DE3783288T2 (de) 1986-08-15 1993-04-22 Fuji Photo Film Co Ltd Farbkopie und verfahren zu deren herstellung.
EP0382285B1 (fr) * 1989-02-08 1994-10-26 Agfa-Gevaert N.V. Matériau de toner en particules
US5449777A (en) * 1993-07-08 1995-09-12 Ciba-Geigy Corporation Phenolic s-triazines
JP3584119B2 (ja) 1996-04-05 2004-11-04 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
US7090969B1 (en) 2005-03-15 2006-08-15 Eastman Kodak Company Coupler and image dye light-stabilizing systems
DE602006017124D1 (de) * 2006-12-18 2010-11-04 3M Innovative Properties Co (meth)acrylharzzusammensetzung und folien daraus
JP4988383B2 (ja) * 2007-03-02 2012-08-01 スリーエム イノベイティブ プロパティズ カンパニー （メタ）アクリル系着色フィルム、マーキングフィルム、レセプターシート、及びその製造方法
JP5307378B2 (ja) * 2007-10-26 2013-10-02 スリーエム イノベイティブ プロパティズ カンパニー （メタ）アクリル系フィルムおよびこれを用いたマーキングフィルム
JP2009270062A (ja) 2008-05-09 2009-11-19 Fujifilm Corp 紫外線吸収剤組成物
CN112010799B (zh) * 2020-09-08 2022-03-25 宿迁联盛科技股份有限公司 一种受阻胺光稳定剂中间体及其制备方法和应用
CN112010800B (zh) * 2020-09-08 2021-11-16 宿迁联盛科技股份有限公司 一种含受阻酚的受阻胺光稳定剂及其制备方法和应用

Citations (2)

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Publication number Priority date Publication date Assignee Title
DE2126187A1 (de) * 1970-05-28 1971-12-09 Sankyo Co Ltd , Komshiroku Photo Industry Co Ltd , Tokio Mittel gegen das Ausbleichen von Farbfotografien
DE2654058A1 (de) * 1975-12-08 1977-06-23 Ciba Geigy Ag Hydroxybenzylmalonsaeurederivate

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US2596926A (en) * 1949-12-16 1952-05-13 Gen Aniline & Film Corp Preparation of azine dye images
US3183219A (en) * 1963-10-29 1965-05-11 Polaroid Corp 2-benzoyl-5-methoxyphenyl acrylate and polymers thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2126187A1 (de) * 1970-05-28 1971-12-09 Sankyo Co Ltd , Komshiroku Photo Industry Co Ltd , Tokio Mittel gegen das Ausbleichen von Farbfotografien
DE2654058A1 (de) * 1975-12-08 1977-06-23 Ciba Geigy Ag Hydroxybenzylmalonsaeurederivate
FR2334672A1 (fr) * 1975-12-08 1977-07-08 Ciba Geigy Ag Esters et amides hydroxybenzyl-maloniques de piperidyle-4, utilisables comme stabilisants de matieres plastiques

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082817A1 (fr) * 1981-12-17 1983-06-29 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0103540A1 (fr) * 1982-08-18 1984-03-21 Ciba-Geigy Ag Matériel d'enregistrement photographique en couleurs
EP0104146B1 (fr) * 1982-09-21 1986-07-30 Ciba-Geigy Ag Matériau d'enregistrement photographique couleur
EP0109937A2 (fr) * 1982-11-18 1984-05-30 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0109937A3 (en) * 1982-11-18 1986-01-02 Ciba-Geigy Ag Colour-photographic recording material
EP0110828A3 (en) * 1982-11-26 1985-12-27 Ciba-Geigy Ag Colour-photographic recording material
EP0110828A2 (fr) * 1982-11-26 1984-06-13 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0111447A2 (fr) * 1982-12-03 1984-06-20 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0111447A3 (en) * 1982-12-03 1986-01-02 Ciba-Geigy Ag Colour-photographic recording material
EP0111448A3 (en) * 1982-12-08 1985-12-27 Ciba-Geigy Ag Colour-photographic recording material
EP0111448A2 (fr) * 1982-12-08 1984-06-20 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
US4629682A (en) * 1982-12-08 1986-12-16 Ciba-Geigy Ag Recording material for color photography
EP0114029A2 (fr) * 1982-12-16 1984-07-25 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0114028A2 (fr) * 1982-12-16 1984-07-25 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0112802A3 (en) * 1982-12-16 1985-12-11 Ciba-Geigy Ag Colour-photographic recording material
EP0114028A3 (en) * 1982-12-16 1985-12-27 Ciba-Geigy Ag Colour-photographic recording material
EP0114029A3 (en) * 1982-12-16 1985-12-27 Ciba-Geigy Ag Colour-photographic recording material
EP0112802A2 (fr) * 1982-12-16 1984-07-04 Ciba-Geigy Ag Matériel d'enregistrement photographique couleur
EP0113124A3 (en) * 1982-12-30 1985-10-23 Konishiroku Photo Industry Co. Ltd. Silver halide photographic light-sensitive material
EP0113124A2 (fr) * 1982-12-30 1984-07-11 Konica Corporation Matériel photographique à l'halogénure d'argent sensible à la lumière

Also Published As

Publication number Publication date
JPS5720617B2 (fr) 1982-04-30
DE2963689D1 (en) 1982-11-04
EP0011051A3 (en) 1980-05-28
JPS5565954A (en) 1980-05-17
CA1145605A (fr) 1983-05-03
US4268593A (en) 1981-05-19
EP0011051B1 (fr) 1982-09-15

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