EP0349331B1 - Farbphotographisches Material - Google Patents

Farbphotographisches Material Download PDF

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Publication number
EP0349331B1
EP0349331B1 EP89306645A EP89306645A EP0349331B1 EP 0349331 B1 EP0349331 B1 EP 0349331B1 EP 89306645 A EP89306645 A EP 89306645A EP 89306645 A EP89306645 A EP 89306645A EP 0349331 B1 EP0349331 B1 EP 0349331B1
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Prior art keywords
carbon atoms
group
coupler
alkyl
photographic element
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French (fr)
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EP0349331A2 (de
EP0349331A3 (en
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Richard Peter C/O Eastman Kodak Co. Szajewski
Terry Ray C/O Eastman Kodak Co. Taber
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Eastman Kodak Co
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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
    • G03C7/32—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

  • This invention relates to color photographic elements.
  • it relates to color photographic elements with a particular combination of development inhibitor releasing compound and cyan dye-forming coupler.
  • Photographic couplers which release a development inhibitor in a controlled manner are described in U.S. Patents 4,248,962 and 4,409,323, inter alia. These couplers comprise a coupler moiety which has a timing group joined in its coupling position. A development inhibitor is attached to the timing group and is released from it after the bond between the timing group and the coupler is cleaved as a result of reaction between the coupler and oxidized color developing agent. Mechanisms by which such release of the development inhibitor from the timing group can occur include an intermolecular nucleophilic displacement reaction, an electron transfer reaction, and a hydrolysis reaction. Development inhibitors also can be released, as a function of development, from timing groups which are released from compounds which are not couplers such as the hydrazides of U.S. Patent 4,684,604 and the hydroquinones of European Patent Application 0,167,168.
  • cyan dye-forming image couplers that contain a ureido group in the 2-position.
  • a photographic element comprising a support bearing a silver halide emulsion layer having associated therewith a DIR compound having the structure I: wherein: CAR is a carrier moiety, TIME is a timing group and INH is a development inhibitor moiety; together with a cyan dye-forming coupler having the structure II: wherein: m is 0 or 1; n is 0, 1 or 2; Y is halogen, or sulfonyl; Q is -O- or -NH-; R1 is an unsubstituted or a substituted, straight or branched chain alkyl group having from 1 to 20 carbon atoms, an unsubstituted or a substituted cycloalkyl group having from 3 to 8 carbon atoms in the ring, an alkylcarbonyl or an alkoxycarbonyl group having from 1 to 20 carbon atoms in the alkyl or the alkoxy moiety; R2 is as defined for R
  • substituents include hydroxy, halogen, or alkoxy having from 1 to 8 carbon atoms.
  • substituents include alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, hydroxy, halogen, alkoxycarbonyl, aryloxycarbonyl, carboxy, acyl, acyloxy, carbonamido, carbamoyl, alkylsulfonyl, arylsulfonyl, sulfonamido and sulfamoyl groups wherein the alkyl and aryl substituents, and the alkyl and aryl moieties of the alkoxy, aryloxy, alkylthio, arylthio, alkoxycarbonyl, arylcarbonyl, acyl, acyloxy, carbonamido, carbamoyl, alkylsulfonyl, arylsulfonyl, sulfonamido and sulfamoyl substituents can contain, respectively, from
  • Coupling off groups defined by Z are well known to those skilled in the art.
  • coupling-off groups include alkoxy, aryloxy, heteroyloxy, sulfonyloxy, acyloxy, acyl, heterocyclyl, sulfonamido, phosphonyloxy and arylazo. These coupling-off groups are described in the art, for example, in U.S. Patent Nos. 2,455,169; 3,227,551; 3,432,521; 3,476,563; 3,617,291; 3,880,661; 4,052,212 and 4,134,766; and in U.K. Patents and published application Nos. 1,466,728; 1,531,927; 1,533,039; 2,006,755A and 2,017,704A.
  • Suitable coupling-off groups which can be represented by Z are: -OCH3, -OC6H5, -OCH2CONHCH2CH2OH, -OCH2CONHCH2CH2OCH3, -OCH2CONHCH2CH2OCOCH3, -OCH2CH2NHSO2CH3, and Especially preferred Z groups are hydrogen and where R4 is an alkyl or an alkoxy group having from 1 to 10 carbon atoms.
  • cyano group is in the para position with respect to the ureido group and n is 0.
  • n 0, the cyano group is para to the ureido group, R1 is alkyl of 1 to 20 carbon atoms and R2 is hydrogen or alkyl of 1 to 4 carbon atoms.
  • n 0, the cyano group is para to the ureido group, R1 is alkyl of 1 to 14 carbon atoms, R2 is hydrogen and R3 is alkyl of 2 to 24 carbon atoms.
  • the carrier moiety can be any moiety which, as a result of reaction with oxidized color developing agent, will release the timing group.
  • the carrier is a coupler, but it can be another group, such a hydrazide, a hydrazine or a hydroquinone.
  • Coupler moieties can form a colored or colorless, diffusible or nondiffusible, reaction product with oxidized color developing agent. Preferred are cyan dye-forming coupler moieties.
  • the DIR compounds are DIR couplers represented by the structure where COUP is a coupler moiety.
  • the preferred - INH group is a mercaptotetrazole or benzotriazole inhibitor.
  • the DIR compound is a cyan dye-forming DIR coupler and is contained in a red-sensitive silver halide emulsion layer together with the cyan dye-forming image coupler or the DIR compound is a yellow dye-forming DIR coupler and is contained in a red-sensitive silver halide emulsion layer together with the cyan dye-forming image coupler.
  • Particularly preferred are couplers where COUP is a naphtholic cyan dye-forming coupler moiety represented by the following generalized structure: where: the unsatisfied bond represents the point of attachment of the timing group, and BALL is a ballast group such as aryl and alkyl, especially alkoxyaryl and aryloxyalkyl.
  • COUP is a yellow dye forming coupler moiety having one of the structures or where the unsatisfied bond is the point of attachment to the timing group
  • BALL is a ballast group such as alkoxycarbonyl, alkoxy, alkylsulfonamido and alkylsulfamyl
  • X is as defined below
  • Y is alkyl such as methyl and t-butyl, and aryl such as phenyl and alkoxy phenyl.
  • TIME timing groups, represented by TIME, for use in these couplers are described in the aforementioned ′962 and ′323 patents and European Patent Application 0255085.
  • timing groups which have the structures: and where: p is 1 to 4; q is 0 or 1; A is -O- or R5 is hydrogen, alkyl of 1-20 carbon atoms or aryl of 6 to 20 carbon atoms; and X is hydrogen and one or more substituents independently selected from hydroxy, cyano, fluoro, chloro, bromo, iodo, nitro, alkyl, alkoxy, aryl, aryloxy, alkoxycarbonyl, aryloxycarbonyl, carbonamido, and sulfonamido X is preferably hydrogen, cyano, nitro or sulfonamido.
  • the development inhibitor which is eventually released from the DIR coupler can be any of the development inhibitors known in the art, such as mercaptotetrazoles, selenotetrazoles, mercaptobenzothiazoles, selenobenzothiazoles, mercaptobenzoxazoles, selenobenzoxazoles, mercaptobenzimidazoles, selenobenzimidazoles, benzotriazoles, and benzodiazoles.
  • the compounds and couplers used in this invention are, in general, known compounds and can be prepared by techniques known in the art. Compounds, described in the copending applications referred to above on page 6 are novel and can be prepared by the procedures described in those applications.
  • the coupler combinations used in the elements of this invention can be incorporated in silver halide emulsions and the emulsions can be coated on a support to form a photographic element.
  • one or both of the couplers can be incorporated in photographic elements adjacent the silver halide emulsion where, during development, the coupler will be in reactive association with development products such as oxidized color developing agent.
  • the photographic elements can be either single color or multicolor elements.
  • the cyan dye-forming coupler is usually associated with a red-sensitive emulsion, although it could be associated with an unsensitized emulsion or an emulsion sensitized to a different region of the spectrum.
  • Multicolor elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element, including the layers of the image-forming units, can be arranged in various orders as known in the art.
  • a typical multicolor photographic element comprises a support bearing a cyan dye image-forming unit comprising at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta image forming unit comprising at least one green-sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler.
  • the element can contain additional layers, such as filter layers, interlayers, overcoat layers, subbing layers, and the like.
  • the silver halide emulsions employed in the elements of this invention can be comprised of silver bromide, silver chloride, silver iodide, silver chlorobromide, silver chloroiodide, silver bromoiodide, silver chlorobromoiodide or mixtures thereof.
  • the emulsions can include silver halide grains of any conventional shape or size. Specifically, the emulsions can include coarse, medium or fine silver halide grains. High aspect ratio tabular grain emulsions are specifically contemplated, such as those disclosed by Wilgus et al U.S. Patent 4,434,226, Daubendiek et al U.S. Patent 4,414,310, Wey U.S.
  • Patent 4,399,215 Solberg et al U.S. Patent 4,433,048, Mignot U.S. Patent 4,386,156, Evans et al U.S. Patent 4,504,570, Maskasky U.S. Patent 4,400,463, Wey et al U.S. Patent 4,414,306, Maskasky U.S. Patents 4,435,501 and 4,643,966 and Daubendiek et al U.S. Patents 4,672,027 and 4,693,964.
  • silver bromoiodide grains with a higher molar proportion of iodide in the core of the grain than in the periphery of the grain such as those described in GB 1,027,146; JA 54/48,521; US 4,379,837; US 4,444,877; US 4,665,012; US 4,686,178; US 4,565,778; US 4,728,602; US 4,668,614; US 4,636,461; EP 264,954.
  • the silver halide emulsions can be either monodisperse or polydisperse as precipitated.
  • the grain size distribution of the emulsions can be controlled by silver halide grain separation techniques or by blending silver halide emulsions of differing grain sizes.
  • Sensitizing compounds such as compounds of copper, thallium, lead, bismuth, cadmium and Group VIII noble metals, can be present during precipitation of the silver halide emulsion.
  • the emulsions can be surface-sensitive emulsions, i.e., emulsions that form latent images primarily on the surfaces of the silver halide grains, or internal latent image-forming emulsions, i.e., emulsions that form latent images predominantly in the interior of the silver halide grains.
  • the emulsions can be negative-working emulsions, such as surface-sensitive emulsions or unfogged internal latent image-forming emulsions, or direct-positive emulsions of the unfogged, internal latent image-forming type, which are positive-working when development is conducted with uniform light exposure or in the presence of a nucleating agent.
  • the silver halide emulsions can be surface sensitized.
  • Noble metal e.g., gold
  • middle chalcogen e.g., sulfur, selenium, or tellurium
  • reduction sensitizers employed individually or in combination, are specifically contemplated.
  • Typical chemical sensitizers are listed in Research Disclosure , Item 17643, cited above, Section III.
  • the silver halide emulsions can be spectrally sensitized with dyes from a variety of classes, including the polymethine dye class, which includes the cyanines, merocyanines, complex cyanines and merocyanines (i.e., tri-, tetra-, and poly-nuclear cyanines and merocyanines), oxonols, hemioxonols, styryls, merostyryls, and streptocyanines.
  • Illustrative spectral sensitizing dyes are disclosed in Research Disclosure , Item 17643, cited above, Section IV.
  • Suitable vehicles for the emulsion layers and other layers of elements of this invention are described in Research Disclosure Item 17643, Section IX and the publications cited therein.
  • the elements of this invention can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein. These additional couplers can be incorporated as described in Research Disclosure Section VII, paragraph C and the publications cited therein.
  • the photographic elements of this invention can contain brighteners (Research Disclosure Section V), antifoggants and stabilizers (Research Disclosure Section VI), antistain agents and image dye stabilizers (Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (Research Disclosure Section VIII), hardeners (Research Disclosure Section XI), plasticizers and lubricants (Research Disclosure Section XII), antistatic agents (Research Disclosure Section XIII), matting agents (Research Disclosure Section XVI) and development modifiers (Research Disclosure Section XXI).
  • the photographic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
  • Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX.
  • Processing to form a visible dye image includes the step of contacting the element with a color developing agent to reduce developable silver halide and oxidize the color developing agent. Oxidized color developing agent in turn reacts with the coupler to yield a dye.
  • Preferred color developing agents are p-phenylene diamines.
  • 4-amino-3-methyl-N,N-diethylaniline hydrochloride 4-amino-3-methyl-N-ethyl-N- ⁇ -(methanesulfonamido)ethylaniline sulfate hydrate, 4-amino-3-methyl-N-ethyl-N- ⁇ -hydroxyethylaniline sulfate, 4-amino-3- ⁇ -(methanesulfonamido)ethyl-N,N-diethylaniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonic acid.
  • this processing step leads to a negative image.
  • this step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the element to render unexposed silver halide developable.
  • a direct positive emulsion can be employed to obtain a positive image.
  • couplers for use in the elements of the invention are shown in Tables I and II above.
  • Photographic elements were prepared with the following layers, in the order indicated, on a cellulose acetate film support:
  • Layer 1 Red sensitized AgBrI emulsion (having an average grain diameter of 0.52»m, 6.4 mole % I) (1.61g Ag/m2, 2.69g gel/m2), cyan image coupler (see Table III) and cyan DIR coupler (see Table III). Equimolar quantities of image couplers were used in the elements and the DIR couplers were used in amounts that would give essentially the same density and gamma in each of the elements after exposure and processing.
  • Layer 2 Overcoat layer of gelatin (1.08 g/m2) and Hardener bisvinylsulfonylmethane coated at 1.75% by weight of total gelatin.
  • the dried coatings were exposed (1/15 sec.) to daylight through a graduated density step wedge and processed at 37.8°C, as follows:
  • Color photographic elements were prepared with the following layers, in the order indicated, on a cellulose acetate film support.
  • Layer 1 A slow cyan dye-forming layer comprising a blend of a red-sensitized 0.42»m silver bromoiodide emulsion (6.1 mol% I) at 1.29g Ag/m2 and a red-sensitized 0.21»m AgBrI emulsion (4.8 mole% I) at 0.43g Ag/m2, gelatin (2.69g/m2), a masking coupler 1-hydroxy-4-(4-[2-(8-acetamido-1-hydroxy-3,6-disulfonaphthyl)azo]phenoxy)-2-( ⁇ -[2,4-di-tert.-amylphenoxy]butyl)naphthamide dipyridine salt (0.041g/m2), a cyan dye-forming coupler (see Table IV) and a DIR coupler (see Table IV).
  • Layer 2 A fast cyan dye-forming layer comprising a 0.76»m silver bromoiodide emulsion (6 mole% I) at 1.08g Ag/m2, gelatin (1.61g/m2), a cyan dye-forming coupler (see Table IV) and a DIR coupler (see Table IV).
  • Layer 5 A gelatin overcoat layer (2.8g/m2) hardened with bisvinylsulfonylmethane at 1.75% by weight of total gelatin. Equimolar quantities of the image coupler (C-1 or II-1) were used and the quantity of DIR coupler (I-2) was chosen to give essentially the same density and gamma in the exposed and processed element.
  • Multicolor photographic elements were prepared having the following schematic structure. In this structure the numbers in parenthesis show the coverage in g/m2.
  • the amounts of couplers in each of the cyan dye forming layers were chosen to give essentially the same density and contrast in the exposed and processed elements.
  • the dried coatings were exposed (1/500 sec), through a graduated density step wedge (Wratten 29 filter), and processed for 3-1/4 minutes in the C-41 process described in the British Journal of Photography Annual, 1977, pages 201-205.
  • the AMT acutance values for 35 mm film system were calculated as described in the previous example.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

Claims (10)

  1. Farbphotographisches Element mit einem Träger sowie einer Silberhalogenidemulsionsschicht, dadurch gekennzeichnet, daß dem Element zugeordnet ist eine DIR-Verbindung der Struktur I:
    Figure imgb0055
     worin bedeuten:
       CAR einen Trägerrest;
       TIME eine Zeitgebergruppe; und
       INH einen Entwicklungsinhibitorrest;
    gemeinsam mit einem einen blaugrünen Farbstoff bildenden Bildkuppler der Struktur II:
    Figure imgb0056
     worin bedeuten:
    m gleich 0 oder 1;
    n gleich 0, 1 oder 2;
    Y Halogen oder Sulfonyl;
    Q gleich -O- oder -NH-;
    R¹ eine unsubstituierte oder eine substituierte, geradkettige oder verzweigtkettige Alkylgruppe mit 1 bis 20 Kohlenstoffatomen, eine unsubstituierte oder eine substituierte Cycloalkylgruppe mit 3 bis 8 Kohlenstoffatomen im Ring, eine Alkylcarbonyl- oder eine Alkoxycarbonylgruppe mit 1 bis 20 Kohlenstoffatomen in dem Alkyl- oder dem Alkoxyrest;
    R² hat die für R¹ angegebene Bedeutung oder steht für Wasserstoff;
    R³ eine unsubstituierte oder eine substituierte Alkylgruppe mit 1 bis 24 Kohlenstoffatomen, eine unsubstituierte oder eine substituierte Cycloalkylgruppe mit 3 bis 8 Kohlenstoffatomen im Ring, eine unsubstituierte oder eine substituierte Arylgruppe mit 6 bis 24 Kohlenstoffatomen oder eine unsubstituierte oder eine substituierte heterocyclische Gruppe mit 3 bis 8 Atomen im heterocyclischen Ring;
    wobei gilt, daß wenn R³ eine primäre Alkylgruppe ist, R¹ mindestens 2 Kohlenstoffatome enthält;
    Z Wasserstoff oder eine abkuppelnde Gruppe; und
    der -CN-Substituent an der Phenylureidogruppe befindet sich in para- oder meta-Stellung zur Ureidogruppe.
  2. Farbphotographisches Element nach Anspruch 1, bei dem in der Struktur II die Cyanogruppe sich in der para-Position befindet und n gleich 0 ist.
  3. Farbphotographisches Element nach Anspruch 2, in dem in der Struktur II R¹ für eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen steht und R² für Wasserstoff oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen.
  4. Farbphotographisches Element nach Anspruch 2, in dem in der Struktur II R¹ für eine Alkylgruppe mit 1 bis 14 Kohlenstoffatomen steht, R² für Wasserstoff und R³ für eine Alkylgruppe mit 2 bis 24 Kohlenstoffatomen.
  5. Farbphotographisches Element nach einem der Ansprüche 2 bis 4, in dem in der Struktur I CAR für einen einen blaugrünen oder gelben Farbstoff bildenden Kupplerrest steht;
    TIME eine der folgenden Strukturen aufweist:
    Figure imgb0057
    Figure imgb0058
     und
    Figure imgb0059
     worin bedeuten:
    p gleich 1 bis 4;
    q gleich 0 oder 1;
    A gleich -O- oder
    Figure imgb0060
     R⁵ gleich Wasserstoff, eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen oder eine Arylgruppe mit 6 bis 20 Kohlenstoffatomen;
    X gleich Wasserstoff und einen oder mehrere Substituenten, die unabhängig voneinander ausgewählt sind aus Hydroxy, Cyano, Fluoro, Chloro, Bromo, Iodo, Nitro, Alkyl, Alkoxy, Aryl, Aryloxy, Alkoxycarbonyl, Aryloxycarbonyl, Carbonamido und Sulfonamido, und worin
    INH für einen Mercaptotetrazolinhibitor oder einen Benzotriazolinhibitor oder einen Oxadiazolinhibitor steht.
  6. Photographisches Element nach Anspruch 5, in dem der DIR- Kuppler eine der folgenden Strukturen aufweist:
    Figure imgb0061
    Figure imgb0062
     oder
    Figure imgb0063
     worin bedeuten:
    BALL eine Ballastgruppe;
    R⁵ Wasserstoff, Alkyl mit 1 bis 20 Kohlenstoffatomen oder Aryl mit 6 bis 20 Kohlenstoffatomen;
    INH einen Mercaptotetrazol- oder einen Benzotriazolinhibitor;
    X gleich Wasserstoff, Cyano, Nitro oder Sulfonamido;
    p gleich 1 bis 4; und
    q gleich 0 oder 1.
  7. Photographisches Element nach Anspruch 1, in dem der einen blaugrünen Farbstoff liefernde Kuppler eine der folgenden Strukturen aufweist:
    Figure imgb0064
    Figure imgb0065
    Figure imgb0066
    Figure imgb0067
    Figure imgb0068
  8. Photographisches Element nach Anspruch 1, in dem die DIR-Verbindung ein Kuppler mit einer der folgenden Strukturen ist:
    Figure imgb0069
    Figure imgb0070
    Figure imgb0071
    Figure imgb0072
  9. Farbphotographisches Element nach Anspruch 1, in dem die DIR-Verbindung ein einen blaugrünen Farbstoff liefernder DIR-Kuppler ist und in einer rot-empfindlichen Silberhalogenidemulsionsschicht gemeinsam mit dem den blaugrünen Farbstoff liefernden Bildkuppler enthalten ist.
  10. Farbphotographisches Element nach Anspruch 1, in dem die DIR-Verbindung ein einen gelben Farbstoff liefernder DIR-Kuppler ist und in einer rot-empfindlichen Silberhalogenidemulsionsschicht zusammen mit dem den blaugrünen Farbstoff liefernden Bildkuppler enthalten ist.
EP89306645A 1988-06-30 1989-06-30 Farbphotographisches Material Expired - Lifetime EP0349331B1 (de)

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US21341588A 1988-06-30 1988-06-30
US213415 1988-06-30

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EP0349331A2 EP0349331A2 (de) 1990-01-03
EP0349331A3 EP0349331A3 (en) 1990-06-27
EP0349331B1 true EP0349331B1 (de) 1995-03-22

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Publication number Priority date Publication date Assignee Title
US5759733A (en) * 1987-11-28 1998-06-02 Ricoh Company, Ltd. Liquid developer for electrostatic electrophotography
CA2010000A1 (en) * 1989-04-07 1990-10-07 Paul B. Merkel Photographic recording material containing a cyan dye-forming coupler
JPH0380245A (ja) * 1989-08-24 1991-04-05 Konica Corp ハロゲン化銀カラー写真感光材料
JP2860411B2 (ja) * 1990-03-30 1999-02-24 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
JPH03288848A (ja) * 1990-04-06 1991-12-19 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JP2715342B2 (ja) * 1991-02-15 1998-02-18 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
US5250400A (en) * 1992-02-26 1993-10-05 Eastman Kodak Company Photographic material and process comprising a pyrazolotriazole coupler
EP0570973B1 (de) * 1992-05-22 1998-11-18 Eastman Kodak Company Farbphotographische Materialien und Verfahren mit DIR- oder DIAR-Kupplern und phenolischen Kupplerlösungsmitteln
US5399466A (en) * 1993-01-15 1995-03-21 Eastman Kodak Company [Method of processing] photographic elements having fogged grains and development inhibitors for interimage
US5411839A (en) * 1993-01-15 1995-05-02 Eastman Kodak Company Image formation in color reversal materials using strong inhibitors
US5380633A (en) * 1993-01-15 1995-01-10 Eastman Kodak Company Image information in color reversal materials using weak and strong inhibitors
US5399465A (en) * 1993-01-15 1995-03-21 Eastman Kodak Company Method of processing reversal elements comprising selected development inhibitors and absorber dyes
US5399467A (en) * 1993-10-29 1995-03-21 Eastman Kodak Company Photographic couplers having a ballast containing a sulfone or sulfoxide group

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JPS56114946A (en) * 1980-02-15 1981-09-09 Konishiroku Photo Ind Co Ltd Silver halide photographic sensitive material
US4775616A (en) * 1986-12-12 1988-10-04 Eastman Kodak Company Cyan dye-forming couplers and photographic materials containing same

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JPH0247650A (ja) 1990-02-16
ATE120285T1 (de) 1995-04-15
DE68921802D1 (de) 1995-04-27
DE68921802T2 (de) 1995-11-16
EP0349331A2 (de) 1990-01-03
EP0349331A3 (en) 1990-06-27

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