EP0141128B1 - Matériau d'enregistrement photographique couleur - Google Patents

Matériau d'enregistrement photographique couleur Download PDF

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Publication number
EP0141128B1
EP0141128B1 EP84110240A EP84110240A EP0141128B1 EP 0141128 B1 EP0141128 B1 EP 0141128B1 EP 84110240 A EP84110240 A EP 84110240A EP 84110240 A EP84110240 A EP 84110240A EP 0141128 B1 EP0141128 B1 EP 0141128B1
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Prior art keywords
layer
silver
material according
mol
sensitive
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EP84110240A
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German (de)
English (en)
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EP0141128A3 (en
EP0141128A2 (fr
Inventor
Helmut Dr. Kampfer
Hans Dr. Langen
Erwin Dr. Ranz
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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
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/3924—Heterocyclic

Definitions

  • the invention relates to a color photographic recording material with improved fog resistance, which has at least one light-sensitive silver halide emulsion layer and at least one layer which contains colloidal silver.
  • Photographic materials undergo a number of adverse changes during storage, including the loss of sensitivity and the increase in fog. These deficiencies occur particularly easily if the material contains layers that contain colloidal silver as a light-absorbing medium. Such layers are arranged, for example, as a silver filter yellow layer (according to Carey Lea) for absorbing unwanted blue light between the blue-sensitive and the green- and red-sensitive layers.
  • a gray, black or blue colloidal silver-containing antihalation layer can be applied under the light-sensitive layers in order to prevent the backscattering of light into the light-sensitive layers and thus a deterioration in sharpness.
  • the advantage of silver as a light-absorbing medium over organic dyes for filter layers is usually that the same absorption effect can be achieved with much thinner layers.
  • a layer containing colloidal silver can adversely affect the photographic properties of the adjacent light-sensitive partial layers. This can be particularly noticeable during storage due to increased fog and loss of sensitivity.
  • Antifoggants which can be used are above all heterocyclic compounds, such as benzimidazoles, benzotriazoles and heterocyclic mercapto compounds, in particular 1-phenyl-5-mercaptotetrazole and its 1-amidophenyl and 1-ureidophenyl derivatives. According to DE-OS 1 547 694 and US Pat. No.
  • No. 3,695,881 discloses a method for producing images in which iodide ions from an emulsion containing silver iodide increases the solubility of another emulsion which has been treated with a phenyl mercaptotetrazole. According to DE-OS 2 437 353 and GB 1 471 554, contamination by silver in the development of black and white materials should be avoided by development in the presence of amidophenyl mercaptotetrazoles.
  • antifoggants with excellent activity are among the proposed compounds, particularly mercaptotetrazole derivatives, they generally have the serious disadvantage that they reduce the photographic sensitivity to a greater or lesser extent by hindering the bleaching of the developed silver during processing or that they contribute to adverse changes in the photographic properties by diffusion into light-sensitive neighboring layers.
  • the object of the invention is to provide an improved color photographic material with at least one light-sensitive silver halide emulsion layer and at least one layer containing colloidal silver, which does not have these disadvantages, in particular the reduction in photographic sensitivity, to the known extent.
  • the antifoggants correspond to the following formula la in which the substituents have the meaning given above.
  • Suitable substituents for R 1 , R 2 , Ar and Het are those which are suitable for antifoggants in light-sensitive silver halide materials, for example hydroxyl, alkoxy, such as, for example, methoxy or ethoxy, halogen, such as fluorine, chlorine or bromine. Het in particular can also be substituted with an aryl, preferably with a phenyl radical.
  • R 1 is hydrogen or an alkyl radical.
  • R 2 represents an alkyl radical.
  • M preferably represents hydrogen.
  • the recording material has at least one blue-sensitive, at least one green-sensitive and at least one red-sensitive layer.
  • the colloidal silver-containing layer is a yellow filter layer, the silver-free layer being arranged with a connection I between the yellow filter layer and a green- or red-sensitive layer.
  • the material according to the invention each has at least one blue, green and red sensitive layer and an antihalation layer with colloidal silver, a silver-free layer with the compound 1 to be used according to the invention being arranged between the antihalation layer and the specified layers.
  • the present invention compounds to be used are preferably used in amounts of from 10- 2 to 10- 8 mol / m 2, preferably in amounts of from 10- 4 to 10- 6 mol / m 2 of the silver-free layers added.
  • colored photographic images can be produced by a wide variety of processes, e.g. according to the silver color bleaching process or according to the color diffusion process.
  • the material according to the invention is particularly suitable for producing colored photographic images by chromogenic development in the presence of color couplers which react with the oxidation product of developers, generally p-phenylenediamines, to form dyes.
  • the color couplers can be added to the color developer.
  • the photographic material itself contains the usual color couplers, which are usually incorporated into the silver halide layers.
  • the red-sensitive layer can contain a non-diffusing color coupler for producing the blue-green partial color image, usually a coupler of the phenol or a-naphthol type.
  • the green-sensitive layer can contain, for example, at least one non-diffusing color coupler for producing the purple partial color image, color couplers of the 5-pyrazolone or imidazolone type usually being used.
  • the blue-sensitive layer can contain, for example, a non-diffusing color coupler for generating the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • the color couplers can e.g. are 6-, 4- and 2-equivalent couplers, including the so-called white couplers, which do not produce any dye when reacted with color developer oxidation products, and DIR couplers.
  • Suitable couplers are known, for example, from the publications “Color Coupler” by W. Pelz in “Messages from the Research Laboratories of Agfa, Leverkusen / Kunststoff”, Volume 111, page 111 (1961), K. Venkataraman in “The Chemistry of Synthetic Dyes”, Vol. 4, 341 to 387, Academic Press (1971) and TH games, "The Theory of the Photographic Process", 4th Ed., pp. 353-362, and from Research Disclosure No. 17643 of December 1978, Section VII.
  • the color photographic recording materials according to the invention preferably contain at least one silver halide emulsion layer unit for recording light from each of the three spectral ranges red, green and blue.
  • Each of these layer units can comprise a single silver halide emulsion layer or also a plurality of silver halide emulsion layers.
  • Color photographic recording materials with double layers for the different spectral ranges are known, for example, from US Pat. Nos. 3,663,228, 3,849,138 and 4,184,876.
  • the silver halide emulsions used can contain chloride, bromide and iodide or mixtures thereof as the halide.
  • the halide content of at least one layer consists of 0 to 10 mol% of Agl, 0 to 10 mol% of AgCl and 0 to 100% of AgBr, the sum of these proportions being 100%.
  • the halide portion can also consist predominantly of chloride.
  • the silver halide horns can e.g. be cubic, octahedral or tabular.
  • the emulsions can be optically sensitized in a manner known per se, e.g. with the usual polymethine dyes, such as neutrocyanines, basic or acidic carbocyanines, rhodacyanines, hemicyanines, styryl dyes, oxonols and the like.
  • polymethine dyes such as neutrocyanines, basic or acidic carbocyanines, rhodacyanines, hemicyanines, styryl dyes, oxonols and the like.
  • Such sensitizers are from F.M. Hamer in "The Cyanine Dyes and related Compounds", (1964). In this regard, reference is made in particular to Ullmann's Encyclopedia of Chemical Engineering, 4th edition. Volume 18, pages 431 ff and on the above-mentioned Research Disclosure No. 17643, Section IV.
  • antifoggants In addition to the antifoggants to be used according to the invention, commonly used antifoggants and stabilizers can be used.
  • azaindenes preferably tetra- or penta-azaindenes, in particular those which are substituted by hydroxyl or amino groups.
  • Such connections are described, for example, in the article by Birr, Z. Wiss. Phot. 47, 1952), pp. 2-58.
  • Other suitable stabilizers and antifoggants are given in Research Disclosure No. 17643 above in Section IV.
  • the usual layer supports can be used for the materials according to the invention, e.g. Cellulose ester supports, e.g. Cellulose acetate and polyester. Also suitable are paper supports, which can optionally be coated, e.g. with polyolefins, especially with polyethylene or polypropylene.
  • Cellulose ester supports e.g. Cellulose acetate and polyester.
  • paper supports which can optionally be coated, e.g. with polyolefins, especially with polyethylene or polypropylene.
  • polyolefins especially with polyethylene or polypropylene.
  • hydrophilic film-forming agents are suitable as protective colloid or binder for the layers of the recording material, e.g. Proteins, in particular gelatin, alginic acid or their derivatives such as esters, amides or salts, cellulose derivatives such as carboxymethyl cellulose and cellulose sulfates, starch or their derivatives or hydrophilic synthetic binders such as polyvinyl alcohol, partially saponified polyvinyl acetate, polyvinyl pyrrolidone and others.
  • Proteins in particular gelatin, alginic acid or their derivatives such as esters, amides or salts, cellulose derivatives such as carboxymethyl cellulose and cellulose sulfates, starch or their derivatives or hydrophilic synthetic binders such as polyvinyl alcohol, partially saponified polyvinyl acetate, polyvinyl pyrrolidone and others.
  • the layers can also contain other synthetic binders in dissolved or dispersed form, such as homo- or copolymers of acrylic or methacrylic acid or their derivatives, such as first, amides or nitriles, and also vinyl polymers, such as vinyl esters or vinyl ethers.
  • binders specified in Research Disclosure 17643 above in Section IX.
  • the layers of the photographic material can be hardened in the usual manner, for example with formaldehyde, with hardeners of the epoxy type, the heterocyclic ethyleneimine and the acryloyl type. Furthermore, it is also possible to harden the layers in accordance with the process of German Offenlegungsschrift 2 218 009 in order to obtain color photographic materials which are suitable for high-temperature processing. It is also possible to harden the photographic layers or the color photographic multilayer materials with hardeners of the diazine, triazine or 1,2-dihydroquinoline series or with hardeners of the vinyl sulfone type.
  • Suitable color developer substances for the material according to the invention are in particular those of the p-phenylenediamine type, e.g. 4-amino-N, N-diethyl-aniline hydrochloride; 4-amino-3-methyl-N-ethyl - N- ⁇ - (methanesulfonamido) ethylaniline sulfate hydrate; 4-amino-3-methyl-N-ethyl-N-ß-hydroxy-ethyl-aniline sulfate; 4-amino-N-ethyl-N- (2-methoxyethyl) -m-toluidine-di-p-toluenesulfonic acid and N-ethyl-N-ß-hydroxyethyl-p-phenylenediamine.
  • the p-phenylenediamine type e.g. 4-amino-N, N-diethyl-aniline hydrochloride; 4-amino
  • the material is usually bleached and fixed. Bleaching and fixing can be carried out separately or together.
  • the usual compounds can be used as bleaching agents, for example fur salts and Fe 3 + complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes, etc.
  • Particularly preferred are iron III complexes of aminopolycarboxylic acids, in particular, for example, ethylenediaminetetraacetic acid, nitrilotriacetic acid, lminodiacetic acid, N-hydroxyethylethylenediamine diamine , Alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • the layers specified below are applied in succession to a cellulose triacetate support provided with an antihalation layer and an adhesive layer.
  • the stated quantities relate to 1 m 2 .
  • the silver application is indicated by specifying the equimolar amounts of silver nitrate:
  • the layer contains a silver bromide iodide emulsion (6 mol% silver iodide), a cyan coupler, a DIR coupler and a mask coupler. Silver application: 3.4 g.
  • the layer contains a silver bromide iodide emulsion with 10 mol% silver iodide and a cyan coupler. Silver application: 2.2 g.
  • the intermediate layer contains 0.7 g of gelatin, 0.09 g of a scavenger for developer oxidation products of the following formula dispersed therein:
  • the layer contains a silver bromide iodide emulsion (6 mol% silver iodide) as well as a purple coupler of the pyrazolone type, a DIR coupler and a yellow mask coupler.
  • the layer contains a silver bromide iodide emulsion (10 mol% silver iodide) and a purple coupler of the pyrazolone type dispersed therein.
  • the intermediate layer contains 0.5 g of gelatin and disperses therein the scavenger for developer oxidation products indicated under layer 3 and optionally the antifoggants indicated in Table 2 below.
  • the yellow filter layer contains colloidal silver. Density: 0.7.
  • the layer contains a silver bromide iodide emulsion (5 mol% silver iodide) and dispersed therein a mixture of yellow couplers of the benzoylacetanilide type.
  • the layer contains a blue-sensitive layer with 6 mol% of silver iodide and a mixture of the yellow couplers indicated under layer 8.
  • the layer contains 0.8 g of a benzotriazole-type UV absorber dispersed in gelatin.
  • the top layer consists of hardened gelatin.
  • the samples were subjected to the following storage conditions A to check their storage stability: 7 days storage at a temperature of 35% ° C, 90% relative humidity and with exclusion of light.
  • Example 1 According to the general construction scheme given in Example 1, five different assemblies to Q were produced, which differed in that the compounds listed in Table 3 below were added in the intermediate layer indicated under 6 between the yellow filter layer and the green-sensitive layer of high sensitivity.
  • Example 2 It can be seen from Example 2 that with increasing amount of the compounds to be used according to the invention, the increase in fog which occurs during storage A decreases.
  • Example 1 A recording material according to Example 1, Structure A is produced, but the compounds to be used according to the invention which are indicated in Table 4 below were introduced into the adhesive layer between the antihalation layer made of colloidal silver and the red-sensitive layer of low sensitivity.
  • the material is stored as described in Example 1 under storage conditions A and B, exposed and then developed as indicated in Example 1.

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

Claims (10)

1. Matériau d'enregistrement de photographie en couleurs comportant au moins une couche d'émulsion photosensible d'halogénure d'argent, au moins une couche contenant de l'argent colloïdal, ainsi qu'au moins une couche exempte d'argent disposée entre ces couches, caractérisé en ce que la couche exempte d'argent contient au moins un agent antivoile répondant à la formule suivante:
Figure imgb0015
dans laquelle
R1 représente un atome d'hydrogène ou un radical aliphatique éventuellement substitué et contenant 1 à 6 atomes de carbone,
R2 représente un radical aliphatique n-valent éventuellement substitué contenant 4 à 17 atomes de carbone, lorsque n représente 1, et 2 à 17 atomes de carbone, lorsque n représente 2,
m représente 0 ou 1,
n représente 1 ou 2,
M représente un atome d'hydrogène, un atome d'un métal alcalin ou un groupe ammonium,
Ar représente un radical aromatique bivalent éventuellement substitué,
Het représente un radical hétérocyclile bivalent contenant au moins un atome de N et pouvant éventuellement être substitué.
2. Matériau selon la revendication 1, caractérisé en ce que l'agent antivoile répond à la formule suivante:
Figure imgb0016
dans laquelle les substituants ont les significations indiquées dans la revendication 1.
3. Matériau selon la revendication 1, caracrérisé en ce qu'il contient au moins un copulant chromogène.
4. Matériau selon la revendication 1, caractérisé en ce qu'il contient au moins une couche sensible au bleu, au moins une couche sensible au vert et au moins une couche sensible au rouge, en ce que la couche contenant de l'argent colloïdal est une couche filtrante jaune et en ce que la couche exempte d'argent est disposée entre le couche filtrante jaune et une couche sensible au vert ou au rouge.
5. Matériau selon la revendication 1, caractérisé en ce qu'il contient au moins une couche sensible au bleu, une couche sensible au vert et une couche sensible au rouge, ainsi qu'une couche antihalo constituée d'argent colloïdal, tandis que la couche exempte d'argent est disposée entre la couche antihalo et les autres couches.
6. Matériau selon la revendication 1, caractérisé en ce que le composé de formule est contenu en une quantité de 10-2 à 10-8 mole/m2.
7. Matériau selon la revendication 1, caracrérisé en ce que le composé de formule est contenu en une quantité de 10-4 à 10-6 mole/m2.
8. Matériau selon la revendication 1, caractérisé en ce qu'au moins une couche d'émulsion photosensible d'halogénure d'argent est divisée en au moins deux couches partielles de sensibilité différente.
9. Matériau selon la revendication 1, caractérisé en ce que l'halogénure d'argent de la couche d'émulsion photosensible d'halogénure d'argent est constitué de 0 à 10% molaires d'iodure d'argent, de 0 à 10% molaires de chlorure d'argent et de 0 à 100% molaires de bromure d'argent, la somme de ces fractions se complétant à 100%.
10. Matériau selon la revendication 1, caractérisé en ce que la couche d'émulsion photosensible à l'halogénure d'argent contient principalement, comme halogénure d'argent, du bromure d'argent.
EP84110240A 1983-09-10 1984-08-29 Matériau d'enregistrement photographique couleur Expired EP0141128B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3332688 1983-09-10
DE19833332688 DE3332688A1 (de) 1983-09-10 1983-09-10 Farbfotografisches aufzeichnungsmaterial

Publications (3)

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EP0141128A2 EP0141128A2 (fr) 1985-05-15
EP0141128A3 EP0141128A3 (en) 1986-01-22
EP0141128B1 true EP0141128B1 (fr) 1988-04-20

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EP84110240A Expired EP0141128B1 (fr) 1983-09-10 1984-08-29 Matériau d'enregistrement photographique couleur

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US (1) US4576907A (fr)
EP (1) EP0141128B1 (fr)
JP (1) JPS6073627A (fr)
DE (2) DE3332688A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4957855A (en) * 1989-09-21 1990-09-18 Eastman Kodak Company Photographic recording material with improved raw stock keeping
JPH03202849A (ja) * 1989-12-28 1991-09-04 Konica Corp レーザー光源用ハロゲン化銀写真感光材料
DE69205263T2 (de) * 1991-12-19 1996-05-15 Eastman Kodak Co Photographisches Umkehrelement und dessen Verarbeitungsverfahren.
JP6655449B2 (ja) * 2016-03-30 2020-02-26 株式会社日本触媒 スクアリリウム化合物

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1445324A (fr) * 1964-09-01 1966-07-08 Eastman Kodak Co Nouveaux mercaptotérazoles et leur utilisation comme inhibiteurs de surdéveloppement dans le traitement de produits photographiques en couleurs
DE1935310C3 (de) * 1968-07-15 1974-02-07 Fuji Photo Film Co. Ltd., Ashigara, Kanagawa (Japan) Verfahren zur Entwicklung eines farbenphotographischen Aufzeichnungsmaterials
US3695881A (en) * 1970-11-25 1972-10-03 Eastman Kodak Co Positive image production with unfogged internal image silver halide emulsion containing mercaptan retarder and a surface latent image silver halide emulsion
DE2308530A1 (de) * 1973-02-21 1974-08-29 Agfa Gevaert Ag Verfahren zur steuerung der entwicklung von farbumkehrfilmen
DE2336721A1 (de) * 1973-07-19 1975-02-06 Agfa Gevaert Ag Farbphotographisches mehrschichtenmaterial mit verbesserter farbdichte
JPS5037436A (fr) * 1973-08-03 1975-04-08
JPS5559463A (en) * 1978-10-30 1980-05-02 Konishiroku Photo Ind Co Ltd Color photographic material
US4448878A (en) * 1981-11-13 1984-05-15 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials

Also Published As

Publication number Publication date
JPS6073627A (ja) 1985-04-25
US4576907A (en) 1986-03-18
EP0141128A3 (en) 1986-01-22
EP0141128A2 (fr) 1985-05-15
DE3332688A1 (de) 1985-03-28
DE3470613D1 (en) 1988-05-26

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