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EP0615633B1 - Solutions de developpement - Google Patents

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Publication number
EP0615633B1
EP0615633B1 EP92924625A EP92924625A EP0615633B1 EP 0615633 B1 EP0615633 B1 EP 0615633B1 EP 92924625 A EP92924625 A EP 92924625A EP 92924625 A EP92924625 A EP 92924625A EP 0615633 B1 EP0615633 B1 EP 0615633B1
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EP
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Prior art keywords
redox
compound
formula
solution
amplification solution
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EP92924625A
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German (de)
English (en)
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EP0615633A1 (fr
Inventor
Peter Jeffery Twist
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Kodak Ltd
Eastman Kodak Co
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Kodak Ltd
Eastman Kodak Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/3017—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials with intensification of the image by oxido-reduction
    • G03C7/302—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials with intensification of the image by oxido-reduction using peroxides
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents

Definitions

  • This invention relates to photographic developer solutions for use in photographic colour processing and in particular to redox developer solutions.
  • Redox (or RX) amplification processes have been described, for example, in British specification Nos 1,268,126, 1,399,481, 1,403,418 and 1,560,572.
  • colour materials are developed to produce a silver image (which may contain only small amounts of silver) which then catalyses redox amplification to form a dye image.
  • the redox amplifying solution contains a reducing agent, for example a colour developing agent, and an oxidising agent which is more powerful than silver halide and which will oxidise the colour developing agent in the presence of the silver image which acts as the catalyst.
  • the oxidised colour developer reacts with a colour coupler (usually contained in the photographic material) to form image dye.
  • the amount of dye formed depends on the time of treatment or the availability of colour coupler rather than the amount of silver in the image as is the case in conventional colour development processes.
  • a particular application of this technology is in the processing of silver chloride colour paper, especially such paper with low silver levels.
  • the amplifying solution contains both an oxidising agent and a reducing agent it is, however, inherently unstable and will decompose on keeping. This instability is catalysed during the processing by the seasoning of species present in the gelatin layer in the photographic material, such as complex transition metal ions such as manganese (Mn), and/or catechol disulphonate 'CDS', 'TIRON',TM.
  • complex transition metal ions such as manganese (Mn)
  • catechol disulphonate 'CDS', 'TIRON',TM catechol disulphonate 'CDS', 'TIRON',TM.
  • sequestering agents which can form a fairly stable soluble complex with the calcium ions or transition metal ions so that the free metal ions, especially ferric ions, are then present in only minute amounts.
  • sequestering agents may include, for example, a polyacetic acid such as diethylaminetriamine pentaacetic acid 'DTPA' or an alkylidene -1,1-diphosphonic acid, such as 1-hydroxy-ethylidene-1,1-diphosphonic acid 'HEPA'.
  • a redox-amplification solution comprising hydrogen peroxide or a substance capable of releasing hydrogen peroxide, a reducing agent, such as a colour developing agent, and in combination three or more sequestering agents comprising a compound of formula (I), as hereinbelow defined, or a salt thereof, a compound of formula (II), as hereinbelow defined, and a compound of formula (III) as hereinbelow defined, for complexing with a transition metal ion to inhibit catalysis of the decomposition of the redox-amplification solution by impurities emanating from a photographic material and enhance the stability of the solution.
  • One class of sequestering agent that is present according to the invention is a polyalkylcarboxylic, phosphonic or sulphonic acid containing at least one amine group which has condensed with one or more alkyl hydrogens of the alkylcarboxylic, phosphonic, or sulphonic-acid, which may be represented by the formula (I)
  • At least one of X 1 , X 2 , X 3 and X 4 is a carboxylic acid group and examples of compounds of formula (I) that are particularly suitable are ethylenediaminetetraacetic acid 'EDTA', propylenediaminetetraacetic acid 'PDTA', nitrilotriacetic acid 'NTA' but most preferably diethylenetriaminepentaacetic acid 'DTPA', these compounds generally being use in the form of their corresponding tetra- or penta-sodium salts.
  • a compound of formula (I), or a salt thereof is combined with an alkylidene-1,1-diphosphonic acid, of formula (II), as defined hereinbelow and a polyhydroxyl phenyl, of formula (III), as defined hereinbelow
  • a compound of formula (II) is defined as
  • a compound of formula (III) is defined as wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, a straight or branched chain alkyl group having 1 to 6 carbon atoms, a hydroxyl, sulphonyl or carboxyl group. and is especially dihydroxyphenyl sulphonate ('catechol' disulphonate 'CDS') or 'TIRON'.
  • the redox-amplification solution comprises diethylenetriaminepentaacetic acid, 'DTPA' or a salt thereof and 1-hydroxy-ethylidene-1,1 diphosphonic acid,'HEPA'
  • sequestering agents may be combined with the ratio of any two of them being in the range 1:1 to 20:1 by volume, wherein either sequestering agent may be present in the greater amount.
  • Each sequestering agent is added in an amount of from .05ml to 100ml/litre of redox solution, preferably lml to 10ml, most preferably 2ml to 6.5ml or an equivalent amount of solid active compound.
  • Compounds capable of releasing hydrogen peroxide include metal peroxides; compounds which include hydrogen peroxide in their crystal structure such as sodium percarbonate; other peroxy compounds such as sodium perborate and persulphate; or soluble organic peroxides, such as butyl peroxide or benzyl peroxide.
  • the hydrogen peroxide or a compound such as mentioned above is added in a sufficient quantity to oxidise the colour developing agent in a suitable length of time.
  • 30% hydrogen peroxide is used in an amount of from 0.5 to 100ml/litre amplification bath, preferably about 5ml/litre but equivalent amounts of, for example, 8% or 3% hydrogen peroxide may also be used.
  • the reducing agent which is generally a colour developing agent, may be any primary aromatic amine, such as a p-aminophenol or p-phenylenediamine.
  • Colour developing agents which can be used include 4-amino-N,N-diethylaniline hydrochloride, 4-amino-3-methyl-N,N-diethylaniline hydrochloride, 4-amino-3-methyl-N-ethyl-N- ⁇ -hydroxyethylaniline sulphate and preferably N-ethyl-N- ⁇ -methanesulphonamidoethyl-3-methyl-4-aminoaniline (CD3).
  • the reducing agent is added in an amount of from about 1 to 20 g/litre, preferably 2 to 5 g/litre.
  • the redox amplification solution preferably has one or more acids, alkalis or buffers , such as an alkali metal carbonate, carbonate/hydrogen carbonate buffer or phosphate buffer to maintain the pH at the required level, which is usually at about pH 10.
  • alkalis or buffers such as an alkali metal carbonate, carbonate/hydrogen carbonate buffer or phosphate buffer to maintain the pH at the required level, which is usually at about pH 10.
  • the solution must be well buffered to provide a large reservoir of hydroxyl ions as a hydrogen ion is produced for each atom of metallic silver formed.
  • the colour developing agent becomes a more powerful reducing agent with respect to the silver and therefore there is a higher rate of photographic development.
  • a high pH makes the developer more susceptible to aerial oxidation and hence more developing agent or protection from oxygen is required.
  • an anti-oxidant such as diethylhydroxylamine may be used.
  • the redox amplification solutions of the present invention may be used with any type of photographic silver halide colour material.
  • Such materials and their possible constituents are described, for example, in Research Disclosure Item 308119, December 1989, published by Kenneth Mason Publications, Emsworth, Hants, United Kingdom. However materials based on predominantly silver chloride emulsions are preferred.
  • the present invention also provides a method of photographic colour processing including a redox amplification step, which comprises the addition of hydrogen peroxide, or a compound capable of releasing hydrogen peroxide, a reducing agent, such as a colour developing agent, and in combination three or more sequestering agents comprising a compound of formula (I), as hereinbefore defined, or a salt thereof, a compound of formula (II), as hereinbefore defined, and a compound of formula (III), as hereinbefore defined, for complexing with a transition metal ion to inhibit catalysis of the decomposition of the redox-amplification solution by impurities emanating from a photographic material and enhance the stability of the solution.
  • a redox amplification step which comprises the addition of hydrogen peroxide, or a compound capable of releasing hydrogen peroxide, a reducing agent, such as a colour developing agent, and in combination three or more sequestering agents comprising a compound of formula (I), as hereinbefore defined, or a salt thereof,
  • the redox amplification stage may be followed directly by a bleach step or an intermediate stop bath may be employed.
  • the photographic material to be processed preferably contains low levels of silver to reduce light scattering and is preferably based on emulsions which comprise at least 80%, preferably at leat 90%, silver chloride and especially substantially pure silver chloride.
  • a developer-amplifier (DEVAMP) of the following composition was prepared:- Component Concentration Potassium carbonate 10.0 g/l Potassium bromide 1.0 mg/l Potassium chloride 0.35 g/l Diethylhydroxylamine (anti-oxidant) 4.0 ml/l CD3 (colour developing agent) 3.5 g/l H 2 O 2 (30%) 5.0 ml/l pH 10.3 Temperature 35°C
  • a developer-amplifier of the composition shown in Example 1 was prepared and a solution of each of the following in tap water containing approximately 200ppm of equivalent calcium carbonate prepared and transferred to glass cylinders maintained at 35°C in a water thermostat.
  • the 'DTPA' is used in the form of a 40% solution of its penta-sodium salt.

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

Abstract

Solution d'amplification d'oxydoréduction comportant du peroxyde d'hydrogène ou une substance pouvant dégager du peroxyde d'hydrogène, ou bien un agent de réduction, par exemple un révélateur couleur, ainsi qu'au moins deux agents complexants associés l'un à l'autre et destinés à se complexer avec un ion d'élément de transition afin d'inhiber la catalyse des impuretés issues d'un enduit de pellicule photographique, et d'améliorer la stabilité de la solution; procédé de traitement photographique en couleurs comprenant l'utilisation de la solution d'amplification d'oxydoréduction; et son utlilisation à cette fin.

Claims (18)

  1. Solution pour le développement par réaction d'amplification par système redox comprenant du peroxyde d'hydrogène, ou une substance capable de libérer du peroxyde d'hydogène, un agent réducteur, tel qu'un développateur chromogène, et en combinaison, trois agents séquestrants ou plus comprenant un composé de formule (I), ou un sel de ce dernier, un composé de formule (II) et un composé de formule (III) pour complexer un ion d'un métal de transition afin d'inhiber la catalyse de la décomposition de la solution pour le développement par réaction d'amplification par système redox par les impuretés émanant d'un produit photographique et de renforcer la stabilité de la solution, dans laquelle le composé de formule (I) est représenté par la structure :
    Figure imgb0016
     où :
    X1 et X2 peuvent être identiques ou différents, et chacun est un atome d'hydrogène, un groupe alkyle à chaîne droite ou ramifiée de 1 à 6 atomes de carbone, un groupe hydroxyle, carboxyle, sulphonyle ou phosphonyle ou le groupe Z,
    où Z =
    Figure imgb0017
    où a, b, c et d sont identiques ou différents et chacun est un atome d'hydrogène, un groupe alkyle à chaîne droite ou ramifiée de 1 à 6 atomes de carbone, un groupe hydroxyle, carboxyle, sulphonyle ou phosphonyle ou X1 et/ou X2 peuvent être des motifs récurrents de A ou B,
    Y est tel que défini pour a, b, c et d ou est le groupe Z ou le groupe B,
    Figure imgb0018
    où
    X3 et X4 sont des groupes identiques ou différents et sont tels que définis pour X1 et X2,
    où la somme de m, n et r est un entier de 1 à 10, et où l'un des atomes d'hydrogène ou les deux atomes d'hydrogène de chacun des groupes (CH2)m, (CH2)n ou (CH2)r peuvent être remplacés par un groupe alkyle à chaîne droite ou ramifiée de 1 à 6 atomes de carbone, à la condition qu'au moins l'un des groupes X1, X2, X3 et X4 soit ou contienne un groupe carboxylique, sulphonyle ou phosphonyle ou un sel de ces derniers, le composé de formule (II) est représenté par la structure :
    Figure imgb0019
    où X est un atome d'hydrogène, un atome d'halogène ou un groupe hydroxyle,
    n est de 0 à 12,
    et le composé de formule (III) est représenté par la structure :
    Figure imgb0020
     où
    R1, R2, R3 et R4 sont identiques ou différents et chacun est un atome d'hydrogène, un groupe alkyle à chaîne droite ou ramifiée de 1 à 6 atomes de carbone, un groupe hydroxyle, sulphonyle ou carboxyle.
  2. Solution selon la revendication 1, comprenant un composé de formule (I), dans laquelle au moins un des groupes X1, X2, X3 et X4 est un groupe acide carboxylique.
  3. Solution selon l'une quelconque des revendications 1 et 2, dans laquelle le composé de formule (I) est l'acide diéthylène-triaminepentaacétique ou un sel de ce dernier.
  4. Solution selon l'une quelconque des revendications 1 et 2, dans laquelle le composé de formule (I) est l'acide éthylène-diaminetétraacétique ou un sel de ce dernier.
  5. Solution selon l'une quelconque des revendications 1 et 2, dans laquelle le composé de formule (I) est l'acide propylène-diaminetétraacétique ou un sel de ce dernier.
  6. Solution selon l'une quelconque des revendications 1 et 2, dans laquelle le composé de formule (I) est l'acide nitrilo-triacétique ou un sel de ce dernier.
  7. Solution selon la revendication 1, dans laquelle le composé de formule (II) est l'acide 1-hydroxyéthylidène-1,1-diphosphonique.
  8. Solution selon la revendication 1, dans laquelle le composé de formule (III) est le sulfonate de dihydroxyphényle.
  9. Solution selon l'une quelconque des revendications 1 à 3, 7 et 8, comprenant, en combinaison, de l'acide diéthylènetriaminepentaacétique ou un sel de ce dernier, de l'acide l-hydroxy-éthylidène-1,1-diphosphonique et du sulfonate de dihydroxyphényle.
  10. Solution selon l'une quelconque des revendications précédentes, dans laquelle le rapport de deux des agents séquestrants est compris entre 1:1 et 20:1 en volume, et dans laquelle l'un ou l'autre des agents séquestrants peut être présent en plus grande quantité.
  11. Solution selon l'une quelconque des revendications précédentes, dans laquelle on ajoute chaque composé selon une quantité de 0,05 ml à 100 ml/litre ou une quantité équivalente de composé actif solide à la solution pour le développement par réaction d'amplification par système redox.
  12. Solution selon la revendication 11, dans laquelle la quantité de chaque composé est comprise entre 2 ml et 6,5 ml ou son équivalent solide.
  13. Solution selon l'une quelconque des revendications précédentes, dans laquelle on utilise une quantité de peroxyde d'hydrogène à 30 % de 0,5 à 100 ml/litre, de préférence d'environ 5 ml/litre de solution.
  14. Solution selon l'une quelconque des revendications précédentes, dans laquelle l'agent réducteur est la N-éthyl-N-β-méthanesulfonamidoéthyl-3-méthyl-4-aminoaniline.
  15. Solution selon l'une quelconque des revendications précédentes, dans laquelle on ajoute une quantité d'agent réducteur comprise entre 1 et 20 g/litre, de préférence de 2 à 5 g/litre.
  16. Procédé de traitement photographique chromogène comprenant une étape d'amplification par système redox qui comprend l'addition de peroxyde d'hydrogène ou d'un composé capable de libérer du peroxyde d'hydrogène, un agent réducteur, tel qu'un développateur chromogène, et en combinaison, trois agents séquestrants ou plus comprenant un composé de formule (I), ou un sel de ce dernier, un composé de formule (II) et un composé de formule (III), tels que définis dans la revendication 1, pour complexer un ion d'un métal de transition afin d'inhiber la catalyse de la décomposition de la solution pour le développement par réaction d'amplification par système redox par les impuretés émanant d'un produit photographique et de renforcer la stabilité de la solution.
  17. Procédé selon la revendication 16, dans lequel la solution pour le développement par réaction d'amplification par système redox est telle que revendiquée dans l'une quelconque des revendications 1 à 15.
  18. Utilisation de la solution pour le développement par réaction d'amplification par système redox telle que revendiquée dans l'une quelconque des revendications 1 à 15 dans un procédé de traitement photographique chromogène tel que revendiqué dans la revendication 16.
EP92924625A 1991-12-03 1992-11-30 Solutions de developpement Expired - Lifetime EP0615633B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9125689 1991-12-03
GB919125689A GB9125689D0 (en) 1991-12-03 1991-12-03 Developer solutions
PCT/EP1992/002763 WO1993011460A1 (fr) 1991-12-03 1992-11-30 Solutions de developpement

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EP0615633A1 EP0615633A1 (fr) 1994-09-21
EP0615633B1 true EP0615633B1 (fr) 1997-02-19

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EP (1) EP0615633B1 (fr)
JP (1) JPH07502131A (fr)
DE (1) DE69217557T2 (fr)
GB (1) GB9125689D0 (fr)
WO (1) WO1993011460A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9419978D0 (en) * 1994-10-04 1994-11-16 Kodak Ltd Photographic processing solution composition
US7493646B2 (en) 2003-01-30 2009-02-17 United Video Properties, Inc. Interactive television systems with digital video recording and adjustable reminders

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2015403A1 (de) * 1970-04-01 1971-10-21 Agfa-Gevaert Ag, 5090 Leverkusen Photographische Farbentwickler
DE2246610C3 (de) * 1972-09-22 1980-01-03 Agfa-Gevaert Ag, 5090 Leverkusen Photographischer Farbentwickler
DE2646807A1 (de) * 1976-10-16 1978-04-20 Agfa Gevaert Ag Verfahren zur farbverstaerkung durch eine oxidative farbkupplung insbesondere bei silberarmen materialien
US4264716A (en) * 1979-09-10 1981-04-28 Eastman Kodak Company Photographic color developer compositions
JPS5965843A (ja) * 1982-10-07 1984-04-14 Fuji Photo Film Co Ltd カラ−画像形成方法
CA1314424C (fr) * 1986-01-24 1993-03-16 Sheridan E. Vincent Substances de developpement pour la photographie en couleurs particulierement utiles aves les elements photographiques a haute teneur en chlorures
DE3706823A1 (de) * 1986-03-04 1987-09-10 Fuji Photo Film Co Ltd Verfahren zur ausbildung eines farbbildes
GB8909580D0 (en) * 1989-04-26 1989-06-14 Kodak Ltd Method of forming a photographic colour image
US4975357A (en) * 1989-05-23 1990-12-04 Eastman Kodak Company Method of photographic color development using polyhydroxy compounds, metal ions and sequestering agents

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Publication number Publication date
GB9125689D0 (en) 1992-01-29
WO1993011460A1 (fr) 1993-06-10
DE69217557T2 (de) 1997-08-28
DE69217557D1 (de) 1997-03-27
EP0615633A1 (fr) 1994-09-21
JPH07502131A (ja) 1995-03-02

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