EP0313083B1 - Farbphotographisches Silberhalogenidmaterial - Google Patents

Farbphotographisches Silberhalogenidmaterial Download PDF

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Publication number
EP0313083B1
EP0313083B1 EP88117593A EP88117593A EP0313083B1 EP 0313083 B1 EP0313083 B1 EP 0313083B1 EP 88117593 A EP88117593 A EP 88117593A EP 88117593 A EP88117593 A EP 88117593A EP 0313083 B1 EP0313083 B1 EP 0313083B1
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Prior art keywords
group
aliphatic
aromatic
atom
heterocyclic
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French (fr)
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EP0313083A2 (de
EP0313083A3 (en
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Keiji C/O Fuji Photo Film Co. Ltd. Mihayashi
Hidetoshi C/O Fuji Photo Film Co. Ltd. Kobayashi
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C7/32—Colour coupling substances
    • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material

Definitions

  • R3 in general formula [A] represents a hydrogen atom or R6U.
  • R6 represents a hydrogen atom, an aliphatic group which preferably has from 1 to 30 carbon atoms, an aromatic group which preferably has from 6 to 30 carbon atoms, a heterocyclic group which preferably has from 1 to 30 carbon atoms, an -OR7 group, an SR7 group, a -COR8 group, an group, a -PO(R7)2 group, a -PO(-OR7)2 group, a group, an group, a -CO2R7 group, an -SO2R7 group, an -SO2OR7 group, or an imido group which preferably has from 4 to 30 carbon atoms (for example succinimido group, maleimido group, phthalimido group, diacylamino group).
  • T in general formula [A] represents a hydrogen atom or a group which can be eliminated by a coupling reaction with the oxidized form of a primary aromatic amine developing agent.
  • groups of the latter type of group include halogen atoms (fluorine atom, chlorine atom, bromine atom and iodine atom), sulfo group, thiocyanato group, isothiocyanato group, selenocyanato group, aliphatic oxy groups which preferably have from 1 to 30 carbon atoms, aromatic oxy groups which preferably have from 6 to 30 carbon atoms, aliphatic thio groups which preferably have from 1 to 30 carbon atoms, aromatic thio groups which preferably have from 6 to 30 carbon atoms, heterocyclic thio groups which preferably have from 1 to 30 carbon atoms, heterocyclic oxy groups which preferably have from 1 to 30 carbon atoms, aromatic azo groups which preferably have from 6 to 30 carbon atoms, heterocyclic groups which preferably
  • Examples of -SR7 groups include a methylthio group, ethylthio group, allylthio group, n-butylthio group, benzylthio group, n-dodecylthio group, phenylthio group, p-t-octylphenylthio group, p-dodecylphenylthio group, and a p-octyloxyphenylthio group.
  • R represents a hydrogen atom, an alkyl group which has from 1 to 4 carbon atoms or a chlorine atom.
  • G represents a -CONH- group, a -COO-group or a substituted or unsubstituted phenylene group.
  • J represents a substituted or unsubstituted alkylene group, phenylene group or aralkylene group.
  • L represents a -CONH- group, -NHCONH- group, -NHCOO-group, -NHCO- group, -OCONH- group, -NH- group, -COO-group, -OCO- group, -CO- group, -O- group, -SO2- group, -NHSO2- group or an -SO2NH- group.
  • a', b' and c' each represent 0 or 1.
  • Q represents a cyan coupler residual group in which a hydrogen atom other than that of the hydroxyl group in the 1-position has been removed from a compound which can be represented by the general formula [A].
  • R32 is a hydrogen atom, a halogen atom (for example a chlorine atom, bromine atom), an alkyl group [for example a substituted alkyl group such as a sulfonamido substituted alkyl group (e.g., sulfonamidomethyl group, 1-sulfonamidoethyl group, 2-sulfonamidoethyl group, 1-methyl-2-sulfonamidoethyl group, 3-sulfonamidopropyl group), acylamino substituted alkyl group (e.g., acylaminomethyl group, 1-acylaminoethyl group, 2-acylaminoethyl group, 1-methyl-2-acylaminoethyl group, 3-acylaminopropyl group), sulfonamido substituted phenylalkyl group (e.g., p-sulfonamidophenylmethyl group, p-s
  • R31, R32, R32' or X is a divalent linking.group and dimers are formed
  • R31, R32 or R32' represents a substituted or unsubstituted alkylene group (for example methylene group, ethylene group, 1,10-decylene group, -CH2CH2-O-CH2-CH2- group), a substituted or unsubstituted phenylene group (for example 1,4-phenylene group, 1,3-phenylene group, and
  • X represents a divalent group corresponding appropriately with the above mentioned univalent groups.
  • non-color forming ethylenic monomers which do not couple with the oxidation products of primary aromatic amine developing agents include acrylic acid, ⁇ -chloroacrylic acid, ⁇ -alkylacrylic acids (for example methacrylic acid), esters and amides derived from these acrylic acids (for example acrylamide, methacrylamide, n-butylacrylamide, t-butylacrylamide, diacetoneacrylamide, methacrylamide, methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, t-butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate and ⁇ -hydroxyethylmethacrylate), methylenebisacrylamide, vinyl esters (
  • the method used to add the magenta couplers to the photosensitive material is based on the method used for the other couplers described hereinafter.
  • the amount of high boiling point organic solvent which is used as a dispersing medium with respect to the couplers is from 0 to 4.0, preferably from 0.1 to 2.0, and more desirably from 0.3 to 1.0, in terms of the ratio by weight.
  • the order of a middle-sensitive emulsion layer/a high-sensitive emulsion layer/a low-sensitive emulsion layer from the farthest side from a support may be used in a same color sensitivity layer as described in JP-A-59-202464.
  • the silver halide contained in the photographic emulsions of the photographic materials of the present invention is preferably a silver iodobromide, silver iodochloride or silver iodochlorobromide which contains not more than about 30 mol% of silver iodide.
  • the most desirable silver halides are silver iodobromides which contain from about 2 mol% to about 25 mol% of silver iodide.
  • tabular grains which have an aspect ratio of at least about 5 can be used in the present invention.
  • Tabular grains can be easily prepared utilizing known methods including those disclosed by Gutoff in Photographic Science and Engineering , Volume 14, pp. 248 - 257 (1970), in U.S. Patents 4,434,226, 4,414,310, 4,433,048 and 4,439,520, and in British Patent 2,112,157.
  • the colored couplers for correcting unwanted absorptions of the colored dyes disclosed in Research Disclosure No. 17643, section VII-G, U.S. Patent 4,163,670, JP-B-57-39413, U.S. Patents 4,004,929 and 4,138,258, and in British Patent 1,146,368 are preferred.
  • Suitable supports which can be used in the present invention have been disclosed on page 28 of the aforementioned Research Disclosure No. 17643, and in the section from the right hand column of page 647 to the left hand column of page 648 of Research Disclosure No. 18716.
  • the total film thickness of the hydrophilic colloid layer is 28 ⁇ m or less in the side of the emulsion layer and that the film swelling speed (T 1/2 ) is 30 s or less.
  • the film thickness means a film thickness which is determined under moisture conditioning at 25°C for 55% RH (2 days).
  • the film swelling speed (T 1/2 ) is determined according to a known method in the art, for example, using a swelling meter whose type is described in A. Green et al, Photographic Science and Engineering , vol. 19, No. 2, pages 124 to 129.
  • the film swelling speed (T 1/2 ) is defined as the time in which the film thickness reaches a saturated film thickness which is 90% of the maximum swell thickness when treated with a color developer at 30°C for 3 min and 15 s.
  • Typical examples of these compounds include 3-methyl-4-amino-N,N-diethylaniline, 3-methyl-4-amino-N-ethyl-N- ⁇ -hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N- ⁇ -methanesulfonamidoethylaniline, 3-methyl-4-amino-N-ethyl-N- ⁇ -methoxyethylaniline, and the sulfate, hydrochloride and p-toluenesulfonate salts of these compounds. Two or more of these compounds can be used conjointly, depending on the intended purpose.
  • They may also contain, as required, various preservatives, such as hydroxylamine, diethylhydroxylamine, sulfite, hydrazines, phenylsemicarbazides, triethanolamine, catechol sulfonic acids, triethylenediamine (1,4-diazabicyclo[2,2,2]octane), organic solvents such as ethylene glycol and diethylene glycol, development accelerators such as benzyl alcohol, poly(ethylene glycol), quaternary ammonium salts and amines, color forming couplers, competitive couplers, fogging agents such as sodium borohydride, auxiliary developing agents such as l-phenyl-3-pyrazolidone, viscosity imparting agents, various chelating agents as typified by the aminopolycarboxylic acids, aminopolyphosphonic acids, alkylphosphonic acids and phosphonocarboxylic acids, typical examples of which include ethylenediamine tetraacetic acid, nitrilo
  • Color development is carried out after a normal black and white development in the case of reversal processing.
  • the known black and white developing agents for example the dihydroxybenzenes such as hydroquinone, the 3-pyrazolidones such as 1-phenyl-3-pyrazolidone, and the amino phenols such as N-methyl-p-aminophenol, can be used individually or in combinations in the black and white development bath.
  • Bleach accelerators can be used, as required, in the bleach baths, bleach-fix baths, or bleach or bleach-fix pre-baths. Actual examples of useful bleach accelerators have been disclosed in the following specifications: compounds having a mercapto group or a disulfide group are disclosed in U.S.
  • Thiosulfates, thiocyanates, thioether based compounds, thioureas and large quantities of iodides can be used as fixing agents, but thiosulfates are generally used for this purpose, and ammonium thiosulfate in particular can be used in the widest range of applications.
  • Sulfites or bisulfites, or carbonyl-bisulfite addition compounds, are the preferred preservatives for bleach-fix baths.
  • the silver halide color photographic materials of this invention are generally subjected to a water washing and/or stabilizing process after the desilvering process.
  • the amount of water used in the water washing process can be fixed within a wide range according to the nature of the photosensitive material (for example the materials, such as the couplers, which are being used), the purpose for use, the wash water temperature, the number of washing tanks (the number of washing stages), the replenishment system, i.e., whether a counter-flow or a sequential-flow system is used, and various other conditions.
  • the relationship between the amount of water used and the number of water washing tanks in a multi-stage counter-flow system can be obtained using the method outlined on pages 248 to 253 of Journal of the Society of Motion Picture and Television Engineers , Volume 64 ( May 1955).
  • the pH of the wash water used in the processing of the photosensitive materials of the invention is within the range of from 4 to 9, and preferably within the range of from 5 to 8.
  • the wash water temperature and washing time can be set variously according to the nature of the photosensitive material and the application. In general, washing conditions of from 20 seconds to 10 minutes at a temperature of from 15 to 45°C, and preferably of from 30 seconds to 5 minutes at a temperature of from 25 to 40°C, are selected.
  • the photosensitive materials of the present invention can be processed directly in a stabilizing bath instead of being subjected to a water wash as described above.
  • the known methods disclosed in JP-A-57-8543, JP-A-58-14834 and JP-A-60-220345 can all be used for this purpose.
  • a stabilization process may be carried out following the aforementioned water washing process.
  • the stabilizing baths contain formalin and surfactant and are used as a final bath for color photosensitive materials.
  • Various chelating agents and fungicides can be added to these stabilizing baths.
  • the overflow which accompanies replenishment of the above mentioned wash water and/or stabilizer can be re-used in other processes such as a desilvering process.
  • the various processing baths are used at a temperature of from 10 to 50°C in the present invention.
  • the standard temperature is normally from 33 to 38°C, but processing is accelerated and the processing time is shortened at higher temperatures and, conversely, higher picture quality and improved stability of the processing baths can be achieved at lower temperatures.
  • processes using hydrogen peroxide intensification or cobalt intensification as disclosed in West German Patent 2,226,770 or U.S. Patent 3,674,499 can be carried out in order to economize on silver in the photosensitive material.
  • silver halide photosensitive materials of this invention can also be used as heat developable photosensitive materials as disclosed in U.S. Patent 4,500,626, JP-A-60-133449, JP-A-59-218443 and JP-A-61-238056, and in European Patent 210,660A2.

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

Claims (7)

  1. Farbphotographisches Silberhalogenidmaterial, umfassend
    mindestens zwei rotempfindliche Silberhalogenidemulsionsschichten, die unterschiedliche Empfindlichkeiten haben und mindestens einen Cyankuppler enthalten;
    mindestens eine grünempfindliche Silberhalogenidemulsionsschicht, die mindestens einen Magentakuppler enthält; und
    mindestens eine blauempfindliche Silberhalogenidemulsionsschicht, die mindestens einen Gelbkuppler enthält, worin die Schichten auf einem Träger angeordnet sind und mindestens einer der Cyankuppler dargestellt ist durch die allgemeine Formel (A), und mindestens einer der Magentakuppler dargestellt ist durch die allgemeine Formel (I) oder die allgemeine Formel (II):
    Figure imgb0182
     worin R₁ ein Halogenatom, eine aliphatische Gruppe, eine aromatische Gruppe, eine heterocyclische Gruppe, eine Amidinogruppe, eine Guanidinogruppe oder eine Gruppe, die dargestellt ist durch -COR₄, -SO₂R₄, -SOR₄,
    Figure imgb0183
     -NHCOR₄, -NHSO₂R₄, -HNSOR₄, oder
    Figure imgb0184
     darstellt,
    R2 ein Halogenatom, eine Hydroxylgruppe, eine Carboxylgruppe, eine Sulfogruppe, eine Aminogruppe, eine Cyanogruppe, eine Nitrogruppe, eine aliphatische Gruppe, eine aromatische Gruppe, eine Carbonamidogruppe, eine Sulfonamidogruppe, eine Carbamoylgruppe, eine Sulfamoylgruppe, eine Ureidogruppe, eine Acylgruppe, eine Acyloxygruppe, eine aliphatische Oxygruppe, eine aromatische Oxygruppe, eine aliphatische Thiogruppe, eine aromatische Thiogruppe, eine aliphatische Sulfonylgruppe, eine aromatische Sulfonylgruppe, eine aliphatische Sulfinylgruppe, eine aromatische Sulfinylgruppe, eine aliphatische Oxycarbonylgruppe, eine aromatische Oxycarbonylgruppe, eine aliphatische Oxycarbonylaminogruppe, eine aromatische Oxycarbonylaminogruppe, eine Sulfamoylaminogruppe, eine heterocyclische Gruppe oder eine Imidogruppe darstellt,
    1' 0 oder eine ganze Zahl bis 3 ist,
    R₃ ein Wasserstoffatom oder eine R₆U-Gruppe darstellt,
    T ein Wasserstoffatom oder eine Gruppe darstellt, die durch eine Kupplungsreaktion mit der oxidierten Form eines primären aromatischen Amin-Entwicklungsmittels entfernt werden kann,
    R₄ und R₅ jeweils unabhängig voneinander eine aliphatische Gruppe, eine aromatische Gruppe, eine heterocyclische Gruppe, eine Aminogruppe, eine aliphatische Oxygruppe oder eine aromatische Oxygruppe darstellen,
    R₆ ein Wasserstoffatom, eine aliphatische Gruppe, eine aromatische Gruppe, eine heterocyclische Gruppe, eine -OR₇ -Gruppe, eine -SR₇ -Gruppe, eine -COR₈ -Gruppe, eine
    Figure imgb0185
     - Gruppe, eine -PO(R₇)₂ -Gruppe, eine -PO(-OR₇)₂ -Gruppe, eine
    Figure imgb0186
     -Gruppe, eine
    Figure imgb0187
     -Gruppe, eine -CO₂R₇ -Gruppe, eine -SO₂R₇ -Gruppe, eine -SO₂OR₇ -Gruppe oder eine Imidogruppe darstellt, und U eine 〉N-R₉ -Gruppe, eine -CO- -Gruppe, eine -SO₂- -Gruppe, eine -SO- -Gruppe oder eine Einfachbindung darstellt,
    R₇ eine aliphatische Gruppe, eine aromatische Gruppe oder eine heterocyclische Gruppe darstellt,
    R₈ ein Wasserstoffatom, eine aliphatische Gruppe, eine aromatische Gruppe oder eine heterocyclische Gruppe darstellt, und
    R₉ und R₁₀ jeweils unabhängig voneinander ein Wasserstoffatom, eine aliphatische Gruppe, eine aromatische Gruppe, eine heterocyclische Gruppe, eine Acylgruppe, ein aliphatische Sulfonylgruppe oder eine aromatische Sulfonylgruppe darstellen oder miteinander verbunden sein können, um einen Ring zu bilden, wenn 1' einen Wert von 2 oder mehr hat, die R₂-Gruppen gleich oder verschieden sein können oder miteinander verbunden sein können, um einen Ring zu bilden, oder R₂ und R₃, oder R₃ und T jeweils miteinander verbunden sein können, um Ringe zu bilden, oder Dimere oder größere Einheiten (Oligomere oder Polymere) gebildet werden können durch Verbinden über zweiwertige Gruppen oder Gruppen mit höherer Wertigkeit an irgendeinem von R₁, R₂, R₃ oder T; mit der Maßgabe, daß der Cyankuppler der Formel (A) nicht
    Figure imgb0188
     ist,
    Figure imgb0189
     worin R₃₁ eine Alkylgruppe, eine Arylgruppe oder eine heterocyclische Gruppe darstellt,
    R₃₂ ein Wasserstoffatom oder eine Substituentengruppe darstellt,
    R₃₂' eine Alkylgruppe, eine Arylgruppe, eine Alkylthiogruppe, eine Arylthiogruppe oder eine heterocyclische Thiogruppe darstellt, und
    X ein Wasserstoffatom oder eine bei der Kupplung abspaltbare Gruppe darstellt,
    worin die rotempfindliche Schicht mit der geringsten Empfindlichkeit einen Vier-Äquivalent-Cyankuppler der allgemeinen Formel (A) enthält, worin T ein Wasserstoffatom ist, und die rotempfindliche Schicht mit der höchsten Empfindlichkeit einen Zwei-Äquivalent-Cyankuppler der allgemeinen Formel (A) enthält, worin T eine Gruppe ist, die kein Wasserstoffatom ist.
  2. Farbphotographisches Material nach Anspruch 1, worin
    R₁ gewählt ist aus der Gruppe bestehend aus einem Halogenatom, einer -COR₄ -Gruppe und einer -SO₂R₄ -Gruppe, worin R₄ eine Aminogruppe ist,
    l' 1 ist,
    R₂ gewählt ist aus der Gruppe bestehend aus einem Halogenatom, einer aliphatischen Gruppe, einer aromatischen Oxygruppe, einer Carbonamidogruppe, einer Sulfonamidogruppe und einer Cyanogruppe,
    R₃ eine R₆U-Gruppe ist, worin R₆ gewählt ist aus der Gruppe bestehend aus einer aliphatischen Gruppe, einer aromatischen Gruppe, einer -OR₇ -Gruppe und einer -SR₇ -Gruppe,
    T gewählt ist aus der Gruppe bestehend aus einem Halogenatom, einer aliphatischen Oxygruppe und einer aliphatischen Thiogruppe,
    R₃₂ gewählt ist aus der Gruppe bestehend aus einer Alkylgruppe, einer Arylgruppe, einer Alkylthiogruppe und einer Arylthiogruppe, und
    X gewählt ist aus der Gruppe bestehend aus einem Halogenatom, einer Carboxylgruppe, einer Gruppe, die über ein Sauerstoffatom verbunden ist, einer Gruppe, die über ein Stickstoffatom verbunden ist und einer Gruppe, die über ein Schwefelatom verbunden ist.
  3. Farbphotographisches Material nach Anspruch 2, worin
    R₁ eine -COR₄ -Gruppe ist, worin R₄ eine Aminogruppe ist,
    l₁ 1 ist,
    R₂ gewählt ist aus der Gruppe bestehend aus einem Fluoratom, einem Chloratom, einer Trifluormethylgruppe, einer Methoxygruppe und einer Cyanogruppe, und
    R₃ gewählt ist aus der Gruppe bestehend aus einer aliphatischen Oxycarbonylgruppe, einer aliphatischen Sulfonylgruppe und einer aromatischen Sulfonylgruppe.
  4. Farbphotographisches Material nach Anspruch 1, worin R31 eine Alkylgruppe oder eine Arylgruppe darstellt.
  5. Farbphotographisches Material nach Anspruch 1, worin X eine Arylthiogruppe darstellt.
  6. Farbphotographisches Material nach Anspruch 1, worin die Menge eines organischen Lösungsmittels mit hohem Siedepunkt, welches als Dispergiermittel für den durch Formel (I) oder (II) dargestellten Kuppler verwendet wird, 0,3 bis 1,0, bezogen auf das Gewicht, beträgt.
  7. Farbphotographisches Material nach Anspruch 1, worin die Menge eines organischen Lösungsmittels mit hohem Siedepunkt, welches als Dispergiermittel für den durch Formel (A) dargestellten Kuppler verwendet wird, 0 bis 0,3, bezogen auf das Gewicht, beträgt.
EP88117593A 1987-10-22 1988-10-21 Farbphotographisches Silberhalogenidmaterial Expired - Lifetime EP0313083B1 (de)

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JP26747887A JPH01108546A (ja) 1987-10-22 1987-10-22 ハロゲン化銀カラー写真感光材料
JP267478/87 1987-10-22

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EP0313083A3 EP0313083A3 (en) 1990-04-25
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Publication number Priority date Publication date Assignee Title
EP0421453A1 (de) * 1989-10-05 1991-04-10 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
DE4004039A1 (de) * 1990-02-10 1991-08-14 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial mit neuen farbigen blaugruenkupplern
JPH0432840A (ja) * 1990-05-29 1992-02-04 Fuji Photo Film Co Ltd ハロゲン化銀カラーネガ写真感光材料
US5298368A (en) * 1991-04-23 1994-03-29 Eastman Kodak Company Photographic coupler compositions and methods for reducing continued coupling

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EP0161626A2 (de) * 1984-05-10 1985-11-21 Fuji Photo Film Co., Ltd. Farbphotographisches lichtempfindliches Silberhalogenidmaterial

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DE3854888T2 (de) 1996-06-13
EP0313083A3 (en) 1990-04-25
JPH01108546A (ja) 1989-04-25
DE3854888D1 (de) 1996-02-22

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