EP0188202B1 - Matériau d'enregistrement photographique et procédé de préparation d'images photographiques - Google Patents

Matériau d'enregistrement photographique et procédé de préparation d'images photographiques Download PDF

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Publication number
EP0188202B1
EP0188202B1 EP86100092A EP86100092A EP0188202B1 EP 0188202 B1 EP0188202 B1 EP 0188202B1 EP 86100092 A EP86100092 A EP 86100092A EP 86100092 A EP86100092 A EP 86100092A EP 0188202 B1 EP0188202 B1 EP 0188202B1
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EP
European Patent Office
Prior art keywords
recording material
photographic
water
layer
photographic recording
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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.)
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EP86100092A
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German (de)
English (en)
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EP0188202A2 (fr
EP0188202A3 (en
Inventor
Hans Dr. Langen
Heinz-Dieter Schütz
Ubbo Dr. Wernicke
Wolfgang Dr. Himmelmann
Günter Dr. Renner
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Agfa Gevaert AG
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Agfa Gevaert AG
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39288—Organic compounds containing phosphorus or silicon
    • 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
    • G03C7/396—Macromolecular additives

Definitions

  • the application relates to a photographic recording material having at least one light-sensitive silver halide emulsion layer and to a method for producing photographic images.
  • Silver halide-based photographic materials are developed and processed after imagewise exposure.
  • the developers used are refreshed to a large extent (English: regenerated) so that they can be used for longer.
  • regenerated a large extent
  • the invention has for its object to provide photographic recording materials and methods for producing photographic images that are stable against processing fluctuations.
  • a photographic recording material with at least one light-sensitive silver halide emulsion layer, a coupler assigned to this silver halide emulsion layer and optionally further layers was found.
  • the recording material contains a phosphonic acid or a water-soluble salt of diose acid and in the coupler-containing layer a polyacrylic acid derivative.
  • the polyacrylic acid derivative is a homo- or copolymer of an ester of unsubstituted or substituted acrylic acid which is soluble in water and insoluble in water.
  • Polymers with recurring units of the formula Ia are particularly preferred wherein R1 and R2 have the meaning given above.
  • Polyacrylic acid derivatives of the formula (I) can be prepared by polymerizing suitable monomers. Suitable monomers are in particular acrylic acid esters and other derivatives of acrylic acid. Different monomers of formula (I) can be used, so that the polyacrylic acid derivative obtained is a copolymer. In addition, other comonomers which do not fall under the formula (I) can also be polymerized. Suitable monomers which give repeating units of the formula (I) are given in Table 1 below:
  • the monomers specified in Table 1 are polymerized together with the following monomers, the monomers specified below each being present in the polymerization mixture in an amount of 1 to 5%: Acrylic acid, methacrylic acid, methacrylic acid methyl ester, fumaric acid butyl ester, acrylonitrile, acrylamide, vinyl isobutyl ether and styrene.
  • R10 and R11 especially when they represent an alkyl group, may be further substituted with at least one hydroxyl, -PO3M2-, -CH2PO3M2- or -N (CH2) n PO3M2 group, where M has the meaning given above.
  • Phosphonic acids to be used according to the invention and their water-soluble salts are also understood to mean those which, instead of a PO3M2 group, are a condensed phosphonic acid group, for example of the following structure exhibit.
  • polyacrylates in photographic recording materials is known per se;
  • GDR patent 144 129 the use of oligomeric polyalkyl acrylates as oil formers is particularly useful to prevent the tendency to crystallize, and in DE-AS 1 954 467 the use of higher molecular weight polyalkylacrylates as oil formers to improve sensitometry (lowering of fog, sensitivity and D-max Increase) described.
  • alkylphosphonic acids are also already known.
  • use is e.g. As a complexing agent for zinc as an emulsion additive (US 3 951 665), as a dispersant for color coupler emulgate (DD 160 619, DD 160 620, DD 160 621) and as a layer additive to prevent stains caused by metal dust (DE-PS 1 289 421).
  • a complexing agent for zinc as an emulsion additive
  • DD 160 619, DD 160 620, DD 160 621 as a dispersant for color coupler emulgate
  • DE-PS 1 289 421 a layer additive to prevent stains caused by metal dust
  • the recording material according to the invention preferably contains at least one blue, green and red sensitive layer on a support, which can be split into sub-layers of different sensitivity.
  • at least one blue-sensitive layer lies above the green- and red-sensitive layers and is separated from them by a yellow filter layer.
  • additional protective and intermediate layers can be used.
  • Color couplers are assigned to the light-sensitive silver halide emulsion layers, which react with color developer oxidation products to form a non-diffusing dye.
  • the color couplers are expediently housed in a non-diffusing manner in the light-sensitive layer itself or in close proximity to it.
  • 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 ⁇ -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 type usually being used.
  • the blue-sensitive layer can contain, for example, at least one non-diffusing color coupler for producing the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • the color couplers can be, for example, 6-, 4- and 2-equivalent couplers. Suitable couplers are known, for example, from the publications "Farbkuppler” by W. Pelz in “Mitanderen” from the research laboratories of Agfa, Leverkusen / Kunststoff “, Volume III, page 111 (1961), K. Venkataraman in” The Chemistry of Synthetic Dyes “, Vol. 4, 341 to 387, Academic Press (1971) and TH James," The Theory of the Photographic Process ", 4th Ed., Pp. 353-362, as well as from Research Disclosure No. 17643 of December 1978, Section VII, published by Industrial Opportunities Ltd., Homewell Havant, Hampshire, PO9 1 EF in Great Britain.
  • the recording material can also contain DIR compounds and white couplers which do not give any dye when reacted with color developer oxidation products.
  • the inhibitors which can be split off from the DIR compounds can be split off directly or via non-inhibiting intermediate compounds.
  • the light-sensitive 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 12 mol% AgI, 0 to 50 mol% AgCl and 50 to 100% AgBr, the sum of these proportions being 100% complementary.
  • the crystals are predominantly compact, for example cubic or are octahedral or have transitional forms. They can be characterized in that they essentially have a thickness of more than 0.2 ⁇ m.
  • the average ratio of diameter to thickness is preferably less than 8: 1, it being true that the diameter of a grain is defined as the diameter of a circle with a circle content corresponding to the projected area of the grain.
  • all or individual emulsions can also have essentially tabular silver halide crystals in which the ratio of diameter to thickness is greater than 8: 1.
  • the emulsions can be chemically sensitized.
  • the usual sensitizers are suitable for chemical sensitization of the silver halide grains.
  • Sulfur-containing compounds for example allyl isothiocyanate, allyl thiourea and thiosulfates, are particularly preferred.
  • Reducing agents and noble metals or noble metal compounds such as gold, platinum, palladium, iridium, ruthenium or rhodium are also suitable as chemical sensitizers, see R. Koslowsky, Z.Wiss.Phot. 46: 65-72 (1951). It is also possible to sensitize the emulsions with polyalkylene oxide derivatives. Reference is also made to Research Disclosure No. 17 643, section III.
  • 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, see F.M. Hamer in "The Cyanine Dyes and related Compounds", (1964), Ullmann's Encyclopedia of Industrial Chemistry, 4th edition. Volume 18, pages 431 ff and Research Disclosure No. 17643, Section IV.
  • polymethine dyes such as neutrocyanines, basic or acidic carbocyanines, rhodacyanines, hemicyanines, styryl dyes, oxonols and the like.
  • the commonly used antifoggants and stabilizers can be used.
  • Particularly suitable stabilizers are mercapto compounds, for example mercaptoazoles, acetylene derivatives, organic reducing agents and azaindenes, preferably tetra- or penta-azaindenes, in particular those which are substituted by hydroxyl or amino groups.
  • Such connections are, for example, in the article by Birr, Z.Wiss.Phot. 47 , 1952), pp. 2-58 and in Research Disclosure No. 17643 given above in Section IV.
  • the components of the photographic material can be incorporated using customary, known methods. If the compounds are soluble in water or alkali, they can be added in the form of aqueous solutions, optionally with the addition of water-miscible organic solvents such as ethanol, acetone or dimethylformamide. If they are water or are insoluble in alkali, they can be incorporated into the recording materials in a known manner in dispersed form. For example, a solution of these compounds in a low-boiling organic solvent can be mixed directly with the silver halide emulsion or initially with an aqueous gelatin solution and the organic solvent can then be removed. The dispersion of the respective compound thus obtained can then be mixed with the silver halide emulsion. If necessary, so-called oil formers are also used, generally higher-boiling organic compounds, which include the compounds to be dispersed in the form of oily droplets. Particularly suitable such oil formers are in particular:
  • Phosphoric acid esters such as triphenyl phosphate and tricresyl phosphate, phthalic acid esters such as dibutyl phthalate, amides such as dibutyl lauryl amide, ethers such as ethylene glycol monobenzyl ether, ketones such as 2-methylcyclohexanone, esters of aliphatic dibasic acid such as ethyl hexyl adipate, esters of aliphatic naphthyronidyl ether pyrid,
  • Polymeric oil formers such as polycondensation products of adipic acid and hexanediol or phthalic acid and hexanediol are also suitable.
  • Oil formers containing carboxyl groups can also advantageously be used, e.g. the succinic acid derivatives of at least one carboxyl group of US Pat. Nos. 3,689,271, 3,764,336 and 3,765,897.
  • the compounds to be emulsified are preferably first dissolved together with at least one compound of the formula (I), if appropriate in a mixture with an oil former, in an organic auxiliary solvent such as ethanol, ethyl acetate, diethyl carbonate, acetone or mixtures thereof.
  • an organic auxiliary solvent such as ethanol, ethyl acetate, diethyl carbonate, acetone or mixtures thereof.
  • the oil former is preferably used in an amount of 0.1 to 2 parts by weight per part by weight of the compound to be emulsified.
  • the organic solution obtained is emulsified in a hydrophilic colloid by customary methods.
  • components of the photographic material for example couplers and UV absorbers in the form of loaded latices, see DE-OS 2 541 274 and EP-A 14 921.
  • the components can also be defined as polymers in the material, see for example DE-OS 2 044 992, US 3 370 952 and US 4 080 211.
  • the usual substrates 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, especially gelatin, see Research Disclosure 17643 Section IX.
  • the layers of the photographic material can be hardened in the usual manner, for example with hardeners of the epoxy type, the heterocyclic ethylene imine and the acryloyl type. Furthermore, it is also possible to harden the layers in accordance with the process of German laid-open specification 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. Further suitable hardening agents are known from German laid-open documents 2 439 551, 2 225 230, 2 317 672 and from Research Disclosure 17643, section XI given above.
  • Development can be carried out in the presence of pH buffers, development inhibitors, anti-fogging agents, water softening complexing agents, preservatives, development accelerators, competitive couplers, fogging agents, auxiliary developer compounds and viscosity modifiers; Reference is made to Research Disclosure 17 544 of December 1978, published by Industrial Opportunities Ltd., Homewell Havant, Hampshire, Great Britain, Section XXI and Ullmanns Encyclopedia of Technical Chemistry, 4th Edition, Volume 18, 1979, in particular pages 451, 452 and 463 to 465. A detailed description of suitable developer compositions and processing methods is given by Grant Haist, Modern Photographic Processing, John Wiley and Sons, 1973, Volumes 1 and 2.
  • Suitable color developer substances for the material according to the invention are in particular those of the p-phenylenediamine type, for example 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- ⁇ -hydroxyethylaniline sulfate; 4-amino-N-ethyl-N- (2-methoxyethyl) -m-toluidine-di-p-toluenesulfonic acid and N-ethyl-N- ⁇ -hydroxyethyl-p-phenylenediamine.
  • 4-amino-N, N-diethyl-aniline hydrochloride 4-amino-3-methyl-N-ethyl-N- ⁇ - (methanesulfon
  • 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 Fe 3+ salts and Fe 3+ complex salts such as ferricyanides, dichromates, water-soluble cobalt complexes etc.
  • Iron-III complexes of aminopolycarboxylic acids in particular for example ethylenediaminetetraacetic acid, nitrilotriacetic acid, iminodiacetic acid, N, are particularly preferred -Hydroxyethylethylenediamintriessigkla, alkyliminodicarboxylic acids and corresponding phosphonic acids.
  • Persulphates are also suitable as bleaching agents.
  • dispersion A 100 g of the specified coupler are dissolved together with 50 g of compound 1.1 and 400 ml of ethyl acetate at 50 ° C and in a 1% of a 5% gelatin solution, also heated to 50 ° C, to which 10 g of triisopropylnaphthalenesulfonate were added, with a high-speed Mixer stirred in and then homogenized under high pressure.
  • the layers mentioned contain other conventional building blocks in addition to the components mentioned.
  • Variants 2 to 8 of Example 1 were prepared accordingly, the composition of dispersion A in layer 10 (low blue-sensitive layer) being varied according to the following table.
  • the developer was composed like developer E-1, but it contained no ethylenediaminetetraacetic acid and instead of 36.3 g potash only 20 g potash.
  • a layer structure was produced as in variant 1, but an additional 0.05 g of compound 2.4 was added to both blue-sensitive layers (layers 10 and 11).
  • Compound 1.1 was used as the oil former.
  • a material was produced as in Example 1, 2nd variant, except that Gb-3 was used as the gb coupler.
  • a material was produced as in the first variant, except that compound 1.2 was used instead of CPM as an oil former and an additional 0.05 g of compound 3.1 was added to the highly and low-sensitive blue-sensitized casting.

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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. Support d'enregistrement photographique comportant au moins une couche photosensible d'émulsion à l'halogénure d'argent, un coupleur associé à la couche d'émulsion à l'halogénure d'argent et, le cas échéant, d'autres couches, caractérisé en ce qu'il contient au moins un acide phosphonique ou un sel hydrosoluble de cet acide et, dans la couche contenant le coupleur, au moins un dérivé d'acide polyacrylique.
  2. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que l'acide phosphonique ou son sel hydrosoluble et le dérivé d'acide polyacrylique sont présents dans la même couche ou dans des couches voisines.
  3. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que le dérivé d'acide polyacrylique et l'acide phosphonique ou son sel hydrosoluble sont présents dans une couche sensible au bleu se trouvant à la partie supérieure.
  4. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que le dérivé d'acide polyacrylique présente des motifs récurrents de structure suivante :
    Figure imgb0017
     dans laquelle
    R¹    représente l'hydrogène ou un groupe alkyle ayant 1 à 4 atomes de carbone,
    A    est un groupe NR²R³ ou OR²
    R², R³    sont identiques ou différents et représentent l'hydrogène ou un groupe alkyle éventuellement substitué.
  5. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce qu'il contient en outre un agent oléifiant.
  6. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que l'acide phosphonique ou son sel hydrosoluble répond à au moins l'une des formules suivantes :
    Figure imgb0018
     dans lesquelles
    X    est un groupe PO₃ M₂ ou COOM
    M    est un atome d'hydrogène ou un cation hydrosolubilisant
    B    est un groupe de jonction éventuellement substitué
    R₁₀, R₁₁,    identiques ou différents, représentent l'hydrogène, un groupe carbamoyle, un groupe alkyle, un groupe aryle substitué, un groupe aralkyle, un groupe alicyclique, un reste hétérocyclique ou forment conjointement le reste complétant un système cyclique.
  7. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que le dérivé d'acide polyacrylique est présent en une quantité de 0,05 à 2,0 g/m² et l'acide phosphonique ou son sel hydrosoluble est présent dans une quantité de 0,05 à 2,0 g/m².
  8. Support d'enregistrement photographique suivant la revendication 1, caractérisé en ce que le dérivé d'acide polyacrylique est un ester soluble dans des solvants organiques et insoluble dans l'eau de l'acide acrylique éventuellement substitué.
  9. Procédé de production d'images photographi ques par développement d'un support d'enregistrement contenant un halogénure d'argent dans un révélateur photographique de couleurs, caractérisé en ce qu'on utilise un support d'enregistrement suivant la revendication 1.
  10. Procédé suivant la revendication 9, caractérisé en ce que le révélateur présente une valeur de pH comprise entre 9,5 et 10,5.
EP86100092A 1985-01-15 1986-01-07 Matériau d'enregistrement photographique et procédé de préparation d'images photographiques Expired - Lifetime EP0188202B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3501074 1985-01-15
DE19853501074 DE3501074A1 (de) 1985-01-15 1985-01-15 Fotografisches aufzeichnungsmaterial und verfahren zur herstellung fotografischer bilder

Publications (3)

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EP0188202A2 EP0188202A2 (fr) 1986-07-23
EP0188202A3 EP0188202A3 (en) 1988-12-07
EP0188202B1 true EP0188202B1 (fr) 1991-04-10

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US (1) US4710454A (fr)
EP (1) EP0188202B1 (fr)
JP (1) JPH0644139B2 (fr)
DE (2) DE3501074A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07122747B2 (ja) * 1987-09-11 1995-12-25 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
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
GB201509677D0 (en) 2015-06-04 2015-07-22 Ge Healthcare Bio Sciences Ab Manufacturing process for polysaccharide beads

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS589941B2 (ja) * 1976-08-06 1983-02-23 富士写真フイルム株式会社 写真画像の形成方法
US4310623A (en) * 1979-12-14 1982-01-12 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
JPS56143430A (en) * 1980-04-11 1981-11-09 Fuji Photo Film Co Ltd Photographic sensitive material with improved antistatic property
JPS59131933A (ja) * 1983-01-19 1984-07-28 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料

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DE3501074A1 (de) 1986-07-17
DE3678585D1 (de) 1991-05-16
JPH0644139B2 (ja) 1994-06-08
EP0188202A2 (fr) 1986-07-23
JPS61174545A (ja) 1986-08-06
US4710454A (en) 1987-12-01
EP0188202A3 (en) 1988-12-07

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