EP0321839B1 - Bain de blanchiment avec des substances accélérant le blanchiment - Google Patents

Bain de blanchiment avec des substances accélérant le blanchiment Download PDF

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Publication number
EP0321839B1
EP0321839B1 EP88120873A EP88120873A EP0321839B1 EP 0321839 B1 EP0321839 B1 EP 0321839B1 EP 88120873 A EP88120873 A EP 88120873A EP 88120873 A EP88120873 A EP 88120873A EP 0321839 B1 EP0321839 B1 EP 0321839B1
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Prior art keywords
bleaching
alkyl
aryl
cycloalkyl
heteroaryl
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EP88120873A
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German (de)
English (en)
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EP0321839A3 (en
EP0321839A2 (fr
Inventor
Peter Dr. Bergthaller
Helmut Häseler
Heinz Dr. Meckl
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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
    • G03C7/42—Bleach-fixing or agents therefor ; Desilvering processes
    • G03C7/421—Additives other than bleaching or fixing agents

Definitions

  • the invention relates to bleaching baths for processing an exposed color photographic light-sensitive silver halide material in which the bleaching function is accelerated, as a result of which the processing time is shortened and also difficult to bleach image silver can be completely bleached.
  • the minimum densities are reduced for reversible materials.
  • the basic stages of processing color photosensitive materials generally include a color development stage and a silver removal stage. In the case of reversal materials, there is also an upstream black / white development and a second exposure. In the last stage, the silver produced during development is oxidized with a bleaching agent and dissolved with a fixing agent.
  • the removal of the silver can be carried out in two stages with a bleaching bath and a fixing bath or in one stage with a bleach-fixing bath.
  • the bleach processing is predominantly carried out using an iron (III) ion complex salt (for example aminopolycarboxylic acid iron (III) complex salt, in particular iron (III) ethylenediaminetetraacetate complex salt).
  • iron (III) ion complex salt for example aminopolycarboxylic acid iron (III) complex salt, in particular iron (III) ethylenediaminetetraacetate complex salt.
  • Iodoso compounds, persulfates, cobalt (III) ion complex salts and cerium IV ion complex salts are also suitable.
  • iron (III) ion complex salts have a comparatively low oxidizing power. There was therefore a need to increase the bleaching power of a bleaching solution or bleach-fixing solution containing a bleaching agent with a low bleaching power, in particular an iron (III) ion complex salt.
  • bleach accelerators examples include thiourea derivatives (JP-OS 8506/70, US Pat. No. 3,706,561), selenourea derivatives (JP-OS 280/71), mercapto compounds with a five-membered ring (GB-PS 1 138 842), thiazole derivatives and thiadiazole derivatives ( CH-PS 336 257).
  • 5-Mercaptotetrazole has also been used as an accelerating agent for the removal of silver in a bleach-fix solution used (GB-PS 1 138 842). However, these compounds have weak accelerating power, poor solubility, or poor stability in the processing solution.
  • DE-OS 3 518 257 describes the bleaching accelerating effect of compounds of the formulas where R19 to R20 are hydrogen, alkyl, acyl or together the remaining members of a ring, m and l are an integer 1 to 3.
  • bleach-fixing baths based on iron-III-EDTA are usually used after the first development, the second exposure and the color development to remove silver from the paper.
  • bleach accelerators are added to the Bleach-fix bath required to effect bleaching sufficiently quickly and completely.
  • compounds such as 3-mercapto-1,2,4-triazole or 5-amino-2-mercapto-1,3,4-triadiazole are used successfully.
  • bleach accelerators in the bleach-fixer has also proven to be useful for color negative paper. If the bleaching is inadequate, residual amounts of silver remain in the materials, which can lead to incorrect information in the mostly IR-controlled cutting device, by means of which the image strip is not cut between the images but in the middle of the images.
  • bleach-fixing bath namely bleaching bath and fixing bath
  • bleach accelerators cannot be used because they no longer have a sufficient, accelerating effect in the bleaching bath, and because some of them do not are sufficiently soluble or cause sediments.
  • bleach accelerator Without bleach accelerator, the insufficiently bleached photo papers show considerable residual silver content in the dark areas of the image, which cannot be significantly reduced even by a longer bath time.
  • the object of the present invention is to provide bleaching or bleach-fixing baths, preferably bleaching baths, which are stable and have an excellent bleaching rate and do not form any sediment. They are intended to ensure low minimum densities in the case of reversal materials during the usual processing times and to completely bleach the residual silver in the blacks in the case of color negative papers. Other photographic properties should not be deteriorated.
  • bleaching or bleach-fixing baths which contain an iron (III) ion complex salt as bleaching agent are a 5- to 7-membered heterocyclic, at least one N- and at least one further heteroatom from the series O, N, S containing compound, which is substituted by -S ⁇ and carries a positive charge on a quaternary ring nitrogen atom, arranged in such a way that tautomeric charge balance to a neutral thione form is not possible.
  • Sulfonamido stands for compounds of the general formula R15-SO2-NH-, where R15 is hydrogen, C1-C8-alkyl, C5-C7-cycloalkyl, C6-C12-aryl or heteroaryl.
  • Sulfamoylamino stands for compounds of the general formula R16R17N-SO2-NH-, where R16 and R17 are the same or different and are hydrogen, C1-C8-alkyl, C5-C6-cycloalkyl, C6-C12-aryl or heteroaryl.
  • Acylamino stands for compounds of the general formula R18-CO-NH-, where R18 is hydrogen, C1-C8-alkyl, C5-C7-cycloalkyl, C6-C12-aryl or heteroaryl.
  • Heteroaryl in general represents a five- or six-membered optionally benzo-fused heteroaromatic ring containing 1 to 3 heteroatoms from the series N, O and S.
  • Hydrophilizing group is understood to mean the following structures: COOH, SO3H, PO (OH) 2, CH2OH, - (O-CH2-CH2) 2 ⁇ 20-OH.
  • Triazolium thiolates according to formula I are known from US 4,631,253 and the common preparation methods are described there.
  • Examples of thiadiazolium thiolates according to formulas II and III and their representation are from Grashey, Baumann and Lubos, Tetrahedron Letters 1968, 5881 and Kier, Scott, J. Heterocycl. Chem. 5, 277, (1968).
  • the oxadiazolium thiolates according to formulas IV are described by McCarthy, Ollis and Ramsden in J. Chem. Soc., Perkin Trans. I 1974, 627.
  • Thiazolium thiolates of the formula V and imidozolium thiolates of the formula VI are published by Huisgen et al in THL 1967, 1809-14.
  • the amount of the compound of the present invention in the bleaching and bleach-fixing baths varies depending on the kind of the processing solution, the kind of the photographic material to be processed, the processing temperature, the time required to carry out the desired processing, etc. However, an amount is 1 x 10 ⁇ 5 to 1 mole per liter of bleaching or bleach-fixing bath is suitable, 1 x 10 ⁇ 3 to 1 x 10 Mol1 mol being preferred. In general, the best range is determined by simple preliminary tests.
  • the compound to be used according to the invention can be added directly to the bleaching or bleach-fixing bath or introduced through an upstream conditioning bath.
  • the bleaching baths according to the invention can also be used in rapid processing processes with development times of less than 60 seconds, the color photographic recording materials used there having chloride-rich silver halide emulsion layers (at least 80 mol% AgCl).
  • Suitable iron (III) ion complex salts are complexes of iron (III) ions and a chelating agent such as an aminopolycarboxylic acid, an aminopolyphosphonic acid or a salt thereof, in particular an alkali metal salt or ammonium salt.
  • Typical examples of chelating agents are ethylenediaminetetraacetic acid; Disodium ethylenediaminetetraacetate; Diammonium ethylenediaminetetraacetate; Tetra (trimethylammonium) ethylenediaminetetraacetate; Tetrapotassium ethylenediaminetetraacetate; Tetrasodium ethylenediaminetetraacetate; Trisodium ethylenediaminetetraacetate; Diethylenetriaminepentaacetic acid; Pentasodium diethylenetriaminepentaacetate; Ethylenediamine-N- ( ⁇ -hydroxyethyl) -N, N ′, N′-triacetic acid; Trisodium ethylenediamine-N- ( ⁇ -hydroxyethyl) -N, N ′, N′-triacetate; Triammonium ethylenediamine-N- ( ⁇ -hydroxyethyl) -N, N ′, N′-triacetate; Propyl
  • the ferric ion complex salt can be used in the form of the complex salt or can be prepared in situ in the bleach or bleach-fix bath. Suitable cations are alkali cations and ammonium; the latter is preferred.
  • the bleaching solution of the present invention may contain rehalogenating agents such as bromides (e.g. potassium bromide, sodium bromide, ammonium bromide, etc.), chlorides (e.g. potassium chloride, sodium chloride, ammonium chloride, etc.) and the like in addition to the bleaching agents.
  • rehalogenating agents such as bromides (e.g. potassium bromide, sodium bromide, ammonium bromide, etc.), chlorides (e.g. potassium chloride, sodium chloride, ammonium chloride, etc.) and the like in addition to the bleaching agents.
  • additives which have a pH buffering action such as inorganic acids, organic acids or the salts thereof, which are known for use in customary bleaching solutions (for example boric acid, borax, sodium metaborate, acetic acid, sodium acetate, sodium carbonate, potassium carbonate, phosphorous acid , Phosphoric acid, sodium phosphate, citric acid, sodium citrate, tartaric acid
  • the pH of the bleaching solution is preferably 3.0 to 8.0, in particular 4.0 to 7.0.
  • thiosulfate eg sodium thiosulfate, ammonium thiosulfate, ammonium sodium thiosulfate, potassium thiosulfate, etc.
  • Thiocyanates eg sodium thiocyanate; Ammonium thiocyanate; Potassium thiocyanate, etc.
  • Thioether compounds e.g. ethylene bisthioglycolic acid, 3,6-di-thia-1,8-octanediol, etc.
  • thioureas can be used alone or in a combination of two or more.
  • special bleach-fixing agents containing a combination of a fixing agent and a large amount of a halide compound such as potassium iodide can also be used.
  • the ferric ion complex salt is usually present in an amount of 0.1 to 1 mol / l.
  • the amount of the fixing agent is generally 0.2 to 4 mol per liter of the bleach-fixing solution.
  • Bleach-fix solutions can also contain preservatives such as sulfites (e.g. sodium sulfite, potassium sulfite, ammonium sulfite, etc.), hydroxylamine, hydrazine, aldehyde-bisulfite adducts (e.g. acetaldehyde sodium bisulfite adduct), etc.
  • sulfites e.g. sodium sulfite, potassium sulfite, ammonium sulfite, etc.
  • hydroxylamine e.g. sodium sulfite, potassium sulfite, ammonium sulfite, etc.
  • hydroxylamine e.g. sodium sulfite, potassium sulfite, ammonium sulfite, etc.
  • hydroxylamine e.g. sodium sulfite, potassium sulfite, ammonium sulfite, etc.
  • hydroxylamine e.
  • the pH of the bleach-fix solution when used is usually 4.0 to 9.0, particularly preferably 5.0 to 8.0.
  • a color negative paper with a silver chloride bromide emulsion (80% AgBr and 20% AgCl) is exposed behind a step wedge and processed as follows: Color developer 210 sec. 33 ° C Watering 20 sec. 20 ° C Wiping the water off the surface of the pictures Bleach bath 50 sec. 20 ° C Watering 60 sec. 20 ° C Fixer 60 sec. 20 ° C Watering 120 sec. 20 ° C dry
  • the step wedges shown are examined with a PM 8030 infrared silver detector from Photo-Matic, Denmark.
  • the table below shows whether residual silver is still present in the blackening after using the freshly prepared bleaching bath.
  • the resistance of the bleaching bath was tested after 4 and 15 days of standing at 33 ° C.
  • sediment formation was assessed after 15 days of inactivity, which can occur especially when a bleach bath containing silver ions is in use.
  • Example 1 is repeated, 2.2 g of thioglycerol / l being added to the bleaching bath as the reference substance.

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

Claims (9)

  1. Bains de blanchiment ou de blanchiment-fixation contenant comme agent de blanchiment un sel complexe d'ions de fer III, caractérisés en ce qu'ils contiennent, en outre, un composé hétérocyclique ayant de 5 à 7 éléments contenant au moins un hétéro-atome N et au moins un autre hétéro-atome choisi dans la série O, N, S, qui est substitué par -S⁻ et qui porte une charge positive sur un atome d'azote quaternaire du cycle, disposé de façon à rendre impossible une compensation de charge tautomère donnant une forme thionique neutre.
  2. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule générale I
    Figure imgb0029
     dans laquelle
    R¹   représente un radical alkyle en C₁-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant.
    R²   représente de l'hydrogène, un radical alkyle en C₁-C₈, un alkényle en C₂-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂, un dialkylamino en C₁-C₈, contenant éventuellement un groupe hydrophilisant.
    R³   représente un groupe amino, acylamino, dialalkylamino en C₁-C₈, sulfonamido, sulfamoylamino, alkyle en C₁-C₈, alkényle en C₂-C₈, C₁-C₃-alcoxy-C₁-C₅-alkyle, cycloalkyle en C₅-C₁₀ ou aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant, et
    dans laquelle R¹ et R² ou R² et R³ peuvent être des groupes nécessaires pour compléter ensemble un cycle hétérocyclique.
  3. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule II ou III
    Figure imgb0030
     dans lesquelles
    R⁴   représente un radical alkyle en C₁-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant,
    R⁵   représente de l'hydrogène, un radical di-C₁-C₈-alkylamino, un radical alkyle en C₁-C₈, alkényle en C₂-C₈, hétéroaryle, cycloalkyle en C₅-C₁₀ ou aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant, et
    dans lesquelles R⁴ et R⁵ peuvent être ensemble des groupes nécessaires pour compléter un cycle hétérocyclique.
  4. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule IV
    Figure imgb0031
     dans laquelle
    R⁶   représente un radical alkyle en C₁-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant,
    R⁷   représente de l'hydrogène, un radical di-C₁-C₈-alkylamino, un radical alkyle en C₁-C₈, un alkényle en C₂-C₈, un hétéroaryle en C₅-C₆, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant, et
    dans laquelle R⁶ et R⁷ peuvent être ensemble des groupes nécessaires pour compléter un cycle hétérocyclique.
  5. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule V
    Figure imgb0032
     dans laquelle
    R⁸   représente un alkyle en C₁-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂ contenant éventuellement un groupe hydrophilisant,
    R⁹ et R¹⁰   représentent de l'hydrogène, un alkyle en C₁-C₈, un alkényle en C₂-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ ou un aryle en C₆-C₁₂ contenant éventuellement un groupe hydrophilisant, et
    dans laquelle R⁸ et R⁹ ou R⁸ et R¹⁰ peuvent être ensemble des groupes nécessaires pour compléter un cycle hétérocyclique.
  6. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule VI
    Figure imgb0033
     dans laquelle
    R¹¹ et R¹³   représentent un radical alkyle en C₁-C₈, un hétéroaryle en C₅-C₆, un cycloalkyle en C₅-C₁₀ et un aryle en C₆-C₁₂, contenant éventuellement un groupe hydrophilisant,
    R¹² et R¹⁴   représentent de l'hydrogène, un radical alkyle en C₁-C₈, un alkényle en C₂-C₈, un hétéroaryle, un cycloalkyle en C₅-C₁₀ et un aryle en C₆-C₁₂ contenant éventuellement un groupe hydrophilisant, et
    dans laquelle R¹¹ et R¹⁴ ou R¹¹ et R¹² ou R¹² et R¹³ peuvent être ensemble des groupes nécessaires pour compléter un cycle hétérocyclique.
  7. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, caractérisés en ce que le composé hétérocyclique correspond à la formule VII
    Figure imgb0034
     dans laquelle
    R¹⁹ et R²⁰   représentent un radical alkyle en C₁-C₃
    R²¹   représente de l'hydrogène et un radical méthyle.
  8. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, dans lesquels le composé supplémentaire est utilisé en quantités comprises entre 10⁻⁵ et 1 mol par litre de bain de blanchiment ou blanchiment-fixation.
  9. Bains de blanchiment et de blanchiment-fixation selon la revendication 1, dans lesquels le sel complexe d'ion de fer III de l'acide éthylène-diamine-tetraacétique est utilise comme agent de blanchiment.
EP88120873A 1987-12-23 1988-12-14 Bain de blanchiment avec des substances accélérant le blanchiment Expired - Lifetime EP0321839B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3743783 1987-12-23
DE19873743783 DE3743783A1 (de) 1987-12-23 1987-12-23 Bleichbaeder mit bleichbeschleunigenden substanzen

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EP0321839A2 EP0321839A2 (fr) 1989-06-28
EP0321839A3 EP0321839A3 (en) 1990-04-04
EP0321839B1 true EP0321839B1 (fr) 1992-11-11

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EP88120873A Expired - Lifetime EP0321839B1 (fr) 1987-12-23 1988-12-14 Bain de blanchiment avec des substances accélérant le blanchiment

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EP (1) EP0321839B1 (fr)
JP (1) JPH01201659A (fr)
DE (2) DE3743783A1 (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2775518B2 (ja) * 1989-12-04 1998-07-16 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法
WO1991008517A1 (fr) * 1989-12-04 1991-06-13 Fuji Photo Film Co., Ltd. Procede et composition de traitement de materiaux photographiques en halogenure d'argent
JP2775517B2 (ja) * 1989-12-04 1998-07-16 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法
JP2640984B2 (ja) * 1989-12-21 1997-08-13 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の処理方法
JPH04229860A (ja) * 1990-12-06 1992-08-19 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料の処理方法
JPH04243252A (ja) * 1991-01-18 1992-08-31 Fuji Photo Film Co Ltd ハロゲン化銀感光材料の現像処理方法
JP2893101B2 (ja) * 1991-02-19 1999-05-17 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法及び写真用定着能組成物
JP2772875B2 (ja) * 1991-05-14 1998-07-09 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の処理方法及び写真用漂白定着組成物
JPH04365036A (ja) * 1991-06-11 1992-12-17 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料の処理方法
JPH04365038A (ja) * 1991-06-11 1992-12-17 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料の処理方法
JP2867350B2 (ja) * 1991-09-19 1999-03-08 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
EP0533182B1 (fr) * 1991-09-20 1999-11-24 Eastman Kodak Company Procédé utilisant des bains comprenant thiolate de triazolium pour accélérer le développement de matériaux photographiques à l'halogénure d'argent
DE69424983T2 (de) 1993-11-24 2000-10-19 Fuji Photo Film Co., Ltd. Photographische Verarbeitungszusammensetzung und Verarbeitungsverfahren
JP3773278B2 (ja) 1994-11-10 2006-05-10 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の処理方法
US5945262A (en) * 1995-12-14 1999-08-31 Agfa-Gevaert, N.B. Correcting liquid for a silver imaged lithographic printing plate
DE10038018A1 (de) 2000-08-04 2002-02-21 Agfa Gevaert Ag Bleichbad
US20050123865A1 (en) * 2003-12-03 2005-06-09 Eastman Kodak Company Single-part bleach-fixing composition and method of processing

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3169466D1 (en) * 1980-12-12 1985-04-25 Eastman Kodak Co Photographic material containing a mesoionic 1,2,4-triazolium-3-thiolate silver halide stabilizing and fixing agent
JPS60144737A (ja) * 1984-01-09 1985-07-31 Fuji Photo Film Co Ltd カラ−拡散転写法用写真感光材料
JPS60163042A (ja) * 1984-02-03 1985-08-24 Fuji Photo Film Co Ltd 写真感光材料
JPS6291952A (ja) * 1985-10-18 1987-04-27 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真材料の処理方法

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DE3875930D1 (de) 1992-12-17
US4939075A (en) 1990-07-03
EP0321839A3 (en) 1990-04-04
DE3743783A1 (de) 1989-07-13
JPH01201659A (ja) 1989-08-14
EP0321839A2 (fr) 1989-06-28

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