EP0577192B1 - Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler - Google Patents

Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler Download PDF

Info

Publication number
EP0577192B1
EP0577192B1 EP19930201812 EP93201812A EP0577192B1 EP 0577192 B1 EP0577192 B1 EP 0577192B1 EP 19930201812 EP19930201812 EP 19930201812 EP 93201812 A EP93201812 A EP 93201812A EP 0577192 B1 EP0577192 B1 EP 0577192B1
Authority
EP
European Patent Office
Prior art keywords
coupler
substituted
photographic
group
unsubstituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP19930201812
Other languages
English (en)
French (fr)
Other versions
EP0577192A1 (de
Inventor
William James C/O Eastman Kodak Company Begley
Stephen Paul C/O Eastman Kodak Company Singer
David Thomas C/O Eastman Kodak Company Southby
Donald c/o Eastman Kodak Company Singleton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0577192A1 publication Critical patent/EP0577192A1/de
Application granted granted Critical
Publication of EP0577192B1 publication Critical patent/EP0577192B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
    • 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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30576—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the linking group between the releasing and the released groups, e.g. time-groups
    • 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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30594—Combination of substances liberating photographically active agents

Definitions

  • This invention relates to new photographic couplers, such as naphtholic and acylanilide couplers, that are capable of forming washout dyes and releasing bleach accelerator groups in a photographic material upon photographic processing for formation of an improved image and to a photographic material and process using such compounds.
  • a photographically useful group (PUG) from a compound, such as a photographic coupler, in a photographic material and process.
  • PAG photographically useful group
  • U.S. Patents 4,248,962; 4,409,323 and 4,861,701 describes groups that enable timed release of a photographically useful group.
  • Bleach accelerator groups have also been used as coupling-off groups, such as described in European Patent Specification No. 193389 and U.S. Patents 4,861,701; 4,959,299 and 4,912,024.
  • the part of the compound that remains in the photographic material after release of the coupling-off groups and the dye that is formed in the material from the reaction with oxidized developer often provide undesired properties in the photographic material during or after photographic processing.
  • the dye formed from a coupler upon release of the coupling-off group often adversely affects the desired image.
  • One answer to this problem has been to provide a water-solubilizing group on the parent coupler to enable the dye formed from the coupler to be washed out of the photographic element upon photographic processing.
  • Such couplers are described in, for example, U.S. Patents 4,482,629 and 5,026,628.
  • a class of washout couplers (couplers capable of forming dyes that may be washed out of photographic materials containing such couplers upon photographic processing) that are especially useful is the naphtholic class of couplers, such as described in U.S. Patents 4,482,629 and 5,026,628.
  • EP-A-0443530 describes a photographic naphtholic coupler moiety comprising a ballast free naptholic coupler moiety containing a -CONH 2 group in the 2- position and a ballasted coupling-off group in the 4- position enables good wash out of dye formed upon oxidative coupling from a photographic material during processing of such a photographic material.
  • a naphtholic coupler is useful in photographic silver halide materials and processes.
  • EP-A-0485965 describes a photographic silver halide element comprising a combination of a first coupler that is capable of releasing a development inhibitor moiety during photographic processing that enhances development inhibition and a second coupler that enables release of a bleach accelerator group upon processing.
  • the photographic silver halide element is useful in photographic imaging.
  • couplers have not provided both enabling of washout of the dye formed and bleach acceleration upon processing of the photographic material containing such a coupler.
  • DIR's development inhibitor releasing couplers
  • a color photographic element comprising a support bearing at least one photographic silver halide emulsion layer, an image dye-forming coupler, and a combination of a development inhibitor releasing coupler and a wash-out coupler, the wash-out coupler (A) being distinct from the development inhibitor releasing coupler, and
  • the development inhibitor releasing coupler is selected from a timed and non-timed development inhibitor releasing coupler (B).
  • Couplers used in the invention can be coated in imaging layers, non-imaging layers or interlayers.
  • Non-imaging layers or interlayers can contain interlayer scavengers, filter dyes of any type known in the photographic art including solid particle dispersion, conventional oil-in water dispersed filter dyes and washout filter dyes, non-imaging silver emulsions such as fine particle Carey-Lea or Lippmann emulsion containing layers, or yellow colored silver emulsions which are non-imaging layers.
  • the interlayers can be located between imaging layers, between non-imaging layers, between an imaging and an non-imaging layer, between an antihalation layer and an interlayer or between an antihalation and an imaging layer.
  • said couplers behave as photographic scavengers, forming washout dyes, and preventing excess oxidized color developer from diffusing to another imaging layer.
  • these couplers can affect the development inhibition of the silver halide in not only the layer in which it is coated but also in adjacent layers thus allowing for the use of increased amounts of development inhibiting releasing compounds in photographic elements, resulting in increased sharpness.
  • one particular advantage of locating said couplers in an interlayer is to minimize any speed loss due to direct competition of oxidized color developer for said couplers over the imaging couplers.
  • washout coupler (A) utilized in this invention is represented by the formula: wherein
  • the development inhibiting releasing coupler (B) may be selected from: wherein:
  • U. S. Patent 4,886,736 discloses timing groups at Col. 16, line 50 through Col. 21 useful for DIR couplers (B) and such groups may contain a ballast.
  • INH can be any releasable development inhibitor group.
  • Typical INH groups are described in, for example U.S. Patents 4,477,563; 4,782,012; 4,886,736; 4,912,024; 4,959,299; and 5,026,628.
  • Preferred development inhibitor groups are heterocyclic inhibitor groups which for example, include mercaptotetrazoles, mercaptoxadiazoles, mercaptothiadiazoles and benzotriazoles.
  • Structures A-1 through A-8 as follows, represent typical releasable development inhibitor groups. wherein:
  • the photographic couplers used in the invention can be incorporated in photographic elements by means and processes known in the photographic art. In a photographic element prior to exposure and processing the photographic coupler should be of such size and configuration that it will not diffuse through the photographic layers.
  • coupler (A) cleaves the bond between the coupling-off group and the coupler moiety of the coupler (A). Tailoring of the particular parts of the releasing groups and timing groups as required for a given releasable bleach accelerator group allows control over the timing and rate of the release of the bleach accelerator group.
  • the releasing group and/or timing groups can contain a ballast group, BALLAST, if desired.
  • BALLAST is a ballast group that is known in the photographic art.
  • the ballast group as described is an organic group of such size and configuration as to confer on the molecule sufficient bulk to render the molecule substantially non-diffusible from the layer in which it is coated in a photographic element.
  • Representative ballast groups include substituted or unsubstituted alkyl or aryl groups typically containing 8 to 40 carbon atoms.
  • the naphtholic coupler moiety can be ballasted or unballasted provided that the dye formed upon oxidative coupling is capable of being washed out of the photographic element.
  • the photographic element can comprise other couplers known in the photographic art.
  • the photographic element can, for example comprise at least one photographic coupler that is capable of release during photographic processing a reagent or a photographic dye.
  • a photographic reagent herein is a moiety that upon release further reacts with components in the photographic element, such as a development inhibitor, a development accelerator, a bleach inhibitor, a bleach accelerator, a coupler (for example, a competing coupler, a dye-forming coupler, or a development inhibitor releasing coupler (DIR coupler), a dye precursor, a dye, a developing agent (for example, a competing developing agent, a dye-forming developing agent, or a silver halide developing agent), a silver complexing agent, a fixing agent, an image toner, a stabilizer, a hardener, a tanning agent, a fogging agent, an ultraviolet radiation absorber, an antifoggant, a nucleator, a chemical or spectral sensitizer or desensitizer.
  • the bleach accelerator group can be present in the coupling-off group as a preformed species or it can be present in a blocked form or as a precursor.
  • the bleach accelerator group can be for example a preformed bleach accelerator group or the bleach accelerator function can be blocked.
  • the naphtholic couplers used in the invention are especially useful in combination with at least one development inhibitor releasing coupler (DIR couplers) known in the photographic art.
  • DIR couplers development inhibitor releasing coupler
  • the photographic couplers used in the invention can be incorporated in photographic elements by means and processes known in the photographic art. In a photographic element prior to exposure and processing the photographic coupler should be of such size and configuration that it will not diffuse through the photographic layers.
  • Photographic elements of this invention can be processed by conventional techniques in which color forming couplers and color developing agents are incorporated in separate processing solutions or compositions or in the element.
  • Photographic elements in which the compounds used in this invention are incorporated can be a simple element comprising a support and a single silver halide emulsion layer or they can be multilayer, multicolor elements.
  • the compounds used in this invention can be incorporated in at least one of the silver halide emulsion layers and/or in at least one other layer, such as an adjacent layer, where they will come into reactive association with oxidized color developing agent which has developed silver halide in the emulsion layer.
  • the silver halide emulsion layer can contain or have associated with it, other photographic coupler compounds, such as dye-forming couplers, colored masking couplers, and/or competing couplers. These other photographic couplers can form dyes of the same or different color and hue as the photographic couplers used in this invention. Additionally, the silver halide emulsion layers and other layers of the photographic element can contain addenda conventionally contained in such layers.
  • a typical multilayer, multicolor photographic element can comprise a support having thereon a red-sensitive silver halide emulsion unit having associated therewith a cyan dye image-providing material, a green-sensitive silver halide emulsion unit having associated therewith a magenta dye image-providing material and a blue-sensitive silver halide emulsion unit having associated therewith a yellow dye image-providing material, at least one of the silver halide emulsion units having associated there with a photographic coupler used in the invention.
  • Each silver halide emulsion unit can be composed of one or more layers and the various units and layers can be arranged in different locations with respect to one another.
  • the light sensitive silver halide emulsions can include coarse, regular or fine grain silver halide crystals or mixtures thereof and can be comprised of such silver halides as silver chloride, silver bromide, silver bromoiodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide and mixtures thereof.
  • the emulsions can be negative-working or direct-positive emulsions. They can form, latent images predominantly on the surface of the silver halide grains or predominantly on the interior of the silver halide grains. They can be chemically and spectrally sensitized.
  • the emulsions typically will be gelatin emulsions although other hydrophilic colloids are useful. Tabular grain light sensitive silver halides are particularly useful such as described in Research Disclosure , January 1983, Item No. 22534, and U.S. Patent 4,434,226.
  • the support can be any support used with photographic elements.
  • Typical supports include cellulose nitrate film, cellulose acetate film, polyvinylacetal film, polyethylene terephthalate film, polycarbonate film and related films or resinous materials as well as glass, paper, metal.
  • a flexible support is employed, such as a polymeric film or paper support.
  • Paper supports can be acetylated or coated with baryta and/or an a-olefin polymer, particularly a polymer of an a-olefin containing 2 to 10 carbon atoms such as polyethylene, polypropylene, ethylene-butene copolymers.
  • the coupler (A) can be used in photographic elements in the same way as photographic couplers which release bleach accelerator groups have previously been used in photographic elements.
  • the couplers can be incorporated in a photographic element for different purposes and in different locations.
  • 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 useful in the invention are p-phenylene diamines.
  • the processing step described above gives a negative image.
  • this step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form a dye, and then uniformly fogging the element to render unexposed silver halide developable.
  • a direct positive emulsion can be employed to obtain a positive image.
  • Photographic elements were prepared comprising the bleach accelerating releasing couplers (BARCs) forming washout dyes as described.
  • BARCs bleach accelerating releasing couplers
  • Example 1 Table 1, it can be seen that compound B-2 used in the invention, releases a bleaching fragment which gives desired bleaching and contrast increases without undesired large speed increases observed with comparison compound Cm-1.
  • the large speed increase associated with Cm-1 is due to the formation of cyan dye which does not wash out of the element.
  • Table 1 also shows two variations in bleaching fragment both of which contain a carboxylic acid group, released from B-3 and B-4. Both give the desired increases in contrast and bleaching performance similar to B-2. They do not show the large speed increases associated with the comparison compound Cm-1.
  • Example 2
  • Strips of each element were exposed to white light through a graduated density step tablet and then developed 3.25 minutes at 40°C in the color developer solution CDs1, described, stopped, washed, bleached using bleach solutions, Bls2, Bls3, and modified bleach solutions Bls1 and Bls3 as described, fixed, washed and dried.
  • Bls3 Distilled water 600mL Ammonium bromide 50.0g 1,3-Propanediaminetetraacetic acid 30.27g Ammonium hydroxide (28% ammonia) 35.20g Ferric nitrate nonahydrate 36.40g Glacial acetic acid 26.50g 1,3-Diamino-2-propanoltetraacetic acid (Rexpronol Acid, Grace) 1.0g Ammonmium ferric EDTA (1.56M, pH 7.05, 44% wgt.) (contains 10% molar excess EDTA, 3.5% wgt.) 149.0g Distilled water to make 1.0L pH at 26.7°C 5.25 +/- 0.10 Adjusted pH with NH 4 OH or HNO 3 .
  • the photographic element containing compound B-2 used in the invention has less red density at D max , than the comparison Cm-1, showing that during processing, the dye formed from the compound used in the invention, is washing out of the photographic element. This is not the case for Cm-1.
  • Table 2 also shows that the photographic element containing compound B-2 used in the invention has lower D min values than those containing S-1. This shows that the compound used in the invention is very effective scavanger of oxidized color developer.
  • Compounds used in the invention give excellent bleaching when coated in interlayers.

Landscapes

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

Claims (8)

  1. Farbfotografisches Element mit einem Träger, auf dem sich mindestens eine fotografische Silberhalogenid-Emulsionsschicht befindet, ein bildfarbstoffbildender Kuppler und eine Kombination eines einen Entwicklungsinhibitor freisetzenden Kupplers ("DIR-Kuppler") und eines Auswaschkupplers (A), der sich vom DIR-Kuppler unterscheidet, wobei das Element
    (i) durch Reaktion mit oxidiertem Entwickler eine Verbindung bilden kann, die bei der Verarbeitung aus dem fotografischen Element ausgewaschen wird oder eine Verbindung bildet, die nach Weiterreaktion ausgewaschen wird und
    (ii) eine Bleichbeschleunigungsgruppe freisetzen kann und
    (iii) durch folgende Formel wiedergegeben wird:
    Figure 00460001
    wobei
    R3
    Wasserstoff ist;
    R4
    aus der Gruppe Wasserstoff, -Cl, -NO2, -OCH3, -NHSO2R5, NHCOR5, -SO2NHR5, -CONHR5, -CO2R5 und -COR5 ausgewählt wird;
    R5
    aus der Gruppe Wasserstoff, substituiertes oder unsubstituiertes Alkyl mit 1-5 Kohlenstoffatomen und substituiertes oder unsubstituiertes Aryl mit 6-8 Kohlenstoffatomen ausgewählt wird, und die substituierte oder unsubstituierte Alkyl- oder Arylgruppe eine solubilisierende Gruppe ist oder eine solubilisierende Gruppe enthält;
    R10
    aus der Gruppe Wasserstoff, substituiertes oder unsubstituiertes Alkyl, substituiertes oder unsubstituiertes Aryl, Nitro, substituiertes oder unsubstituiertes Amino, Carbonsäure, Sulfonsäure, Methoxy, Chlor, Brom, Estergruppen, Ketogruppen, -NHCOCH3, -CONHCH3, -NHSO2CH3 und -SO2NHCH3 ausgewählt wird;
    R11 und R12
    aus der Gruppe Wasserstoff, substituiertes oder unsubstituiertes Alkyl und substituiertes oder unsubstituiertes Aryl ausgewählt werden;
    Z1
    die Atome sind, die für die Ausbildung eines 6-gliedrigen Aryl- oder eines 5- oder 6-gliedrigen heterocyclischen Rings benötigt werden;
    Q
    Sauerstoff, Schwefel oder Stickstoff ist;
    W
    0, 1, 2 oder 3 ist;
    mindestens eine der Gruppen R10, R11 und R12 eine fotografische Ballastgruppe enthält, und
    BLEICHE für die Formel steht -S-R13-COOH,
    wobei R13 eine unsubstituierte oder substituierte Alkylengruppe mit 1 bis 8 Kohlenstoffatomen darstellt.
  2. Farbfotografisches Element nach Anspruch 1, dadurch gekennzeichnet, dass der Kuppler (A) durch folgende Formeln dargestellt wird:
    Figure 00470001
    Figure 00480001
  3. Farbfotografisches Element nach Anspruch 1 und 2 mit einem Träger, auf dem sich in der Reihenfolge
    mindestens eine rotempfindliche fotografische Silberhalogenid-Emulsionsschicht mit mindestens einem farbstoffbildenden Kuppler für das Blaugrünbild,
    mindestens eine grünempfindliche fotografische Silberhalogenid-Emulsionsschicht mit mindestens einem farbstoffbildenden Kuppler für das Purpurbild,
    mindestens eine blauempfindliche fotografische Silberhalogenid-Emulsionsschicht mit mindestens einem farbstoffbildenden Kuppler für das Gelbbild befindet und
    mindestens eine der Schichten mindestens einen wie in Anspruch 1 und 2 definierten Auswaschkuppler (A) und mindestens einen DIR-Kuppler enthält.
  4. Fotografisches Element nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass sich der Auswaschkuppler (A) in einer bilderzeugenden Schicht befindet.
  5. Fotografisches Element nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass sich der Auswaschkuppler (A) in einer Zwischenschicht zwischen zwei bilderzeugenden Schichten befindet.
  6. Farbfotografisches Element nach Anspruch 1 bis 5, dadurch gekennzeichnet, dass der DIR-Kuppler eine der folgenden Verbindungen ist:
    Figure 00490001
    wobei
    INH eine die fotografische Entwicklung inhibierende Gruppe ist;
    KUPPLER eine Kuppler-Komponente ist;
    BALLAST eine fotografische Ballastgruppe ist;
    Q entweder O (Sauerstoff), S (Schwefel) oder N (Stickstoff) ist;
    R6 und R10 Wasserstoff oder Substituenten sind, die aus der Gruppe substituiertes oder unsubstituiertes Alkyl, substituiertes oder unsubstituiertes Aryl, Nitro, Amino, substituiertes Amino, Carbonsäure, Sulfonsäure, Methoxy, Chlor, Brom, Estergruppen, Ketogruppen, -NHCOCH3, -CONHCH3, -NHSO2CH3 oder -SO2NHCH3 ausgewählt werden;
    R7, R8, R11 und R12 Substituenten sind, die aus der Gruppe Wasserstoff, substituiertes oder unsubstituiertes Alkyl und substituiertes oder unsubstituiertes Aryl ausgewählt werden;
    R9 substituiertes oder unsubstituiertes Alkyl oder substituiertes oder unsubstituiertes Aryl ist;
    Z1 die Atome sind, die für die Ausbildung eines 6-gliedrigen Aryl- oder eines 5- oder 6-gliedrigen heterocyclischen Rings benötigt werden;
    R2b eine Zeitgebergruppe ist;
    p und m jeweils 0 oder 1 sind;
    n 0, 1 oder 2 ist, und
    mindestens eine der Gruppen R6, R7, R8, R9, R10, R11 und R12 eine fotografische Ballastgruppe enthält, wenn m gleich 0 ist.
  7. Verfahren zur Bilderzeugung in einem belichteten, in Anspruch 1 - 6 definierten fotografischen Element, das die Entwicklung des fotografischen Elements mit einem Farbentwickler umfasst.
EP19930201812 1992-06-29 1993-06-23 Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler Expired - Lifetime EP0577192B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90624792A 1992-06-29 1992-06-29
US906247 1992-06-29

Publications (2)

Publication Number Publication Date
EP0577192A1 EP0577192A1 (de) 1994-01-05
EP0577192B1 true EP0577192B1 (de) 2000-08-09

Family

ID=25422148

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19930201812 Expired - Lifetime EP0577192B1 (de) 1992-06-29 1993-06-23 Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler

Country Status (3)

Country Link
EP (1) EP0577192B1 (de)
JP (1) JPH0659413A (de)
DE (1) DE69329172T2 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19832309C1 (de) * 1998-07-17 1999-10-14 Siemens Ag Integrierte Schaltung mit einem Spannungsregler

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2036041A1 (en) * 1990-02-22 1991-08-23 William James Begley Photographic material and process comprising wash-out naphtholic coupler
US5026628A (en) * 1990-02-22 1991-06-25 Eastman Kodak Company Photographic material and process comprising a compound capable of forming a wash-out dye
US5135839A (en) * 1990-11-13 1992-08-04 Eastman Kodak Company Silver halide material with dir and bleach accelerator releasing couplers

Also Published As

Publication number Publication date
EP0577192A1 (de) 1994-01-05
DE69329172T2 (de) 2001-04-05
JPH0659413A (ja) 1994-03-04
DE69329172D1 (de) 2000-09-14

Similar Documents

Publication Publication Date Title
EP0443530A2 (de) Photographisches Material und Verfahren, das einen auswaschbaren Naphtholkuppler umfasst
EP0349331A2 (de) Farbphotographisches Material
EP0583020B1 (de) Photographisches Material mit verbesserten Körnigkeitseigenschaften
EP0576088B1 (de) Photographisches Material und Verfahren, einen Kuppler umfassend, das eine auswaschbare Farbe zu bilden vermag
EP0577192B1 (de) Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler
US5283163A (en) Photographic material and process employing a development inhibitor releasing compound containing a fluorinated carbon alpha to an amide group
EP0608959B1 (de) Photographisches Element und Verfahren mit verbesserter Farbwiedergabe
US5192646A (en) Photographic elements having sulfoxide coupler solvents and addenda to reduce sensitizing dye stain
EP0574090A1 (de) 1-Äquivalentkuppler und freisetzbaren Farbstoffen mit niedrigem pKa
EP0571030B1 (de) Photographisches Material mit aneinander grenzenden rotempfindlichen Schichten
JP3195425B2 (ja) 水可溶化ナフトール系カプラーを用いるハロゲン化銀写真材料及び写真処理
EP0566416A1 (de) Photographisches Material mit nebeneinanderliegenden grünempfindlichen Schichten
EP0577182B1 (de) Photographisches Material und Verfahren, einen Kuppler umfassend, das einen auswaschbaren Farbstoff zu bilden vermag
US5358828A (en) Photographic element and process comprising a bleach accelerator releasing compound
US5318879A (en) Photographic element comprising a bleach accelerator releasing compound
EP0577193B1 (de) Photographisches Element enthaltend eine Kombination von einem Entwicklungsinhibitor freisetzenden Kuppler und einen Bleichbeschleuniger freisetzende Verbindung
EP0596575B1 (de) Photographisches Material und einen Pyrazolotriazolrestumfassendes Verfahren
US5286859A (en) Method of forming a photographic washout coupler (BARC) using a strong base
US5286613A (en) Photographic material comprising a combination of couplers forming washout and non-washout dyes
EP0566415A2 (de) Photographisches Material mit geringem Schleier
EP0550110B1 (de) Photographisches Material mit genauer Wiedergabe des Rots
EP0577183A1 (de) Photographisches Material eine Kupplermischung enthaltend, die auswaschbare Farben zu bilden vermag
EP0577191A2 (de) Photographisches Element und Verfahren, das eine bleichbeschleunigende freisetzende Verbindung umfasst und Verfahrer zur Herstellung dieser
JPH04241349A (ja) ハロゲン化銀カラー写真感光材料

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE FR GB IT LI NL

17P Request for examination filed

Effective date: 19940608

17Q First examination report despatched

Effective date: 19970829

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

RBV Designated contracting states (corrected)

Designated state(s): DE FR GB

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REF Corresponds to:

Ref document number: 69329172

Country of ref document: DE

Date of ref document: 20000914

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010623

26N No opposition filed
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20010623

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020228

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20020628

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040101