EP0193389B2 - Verwendung eines Kupplers enhaltend eine abspaltbare, bleichbeschleunigende Gruppe - Google Patents

Verwendung eines Kupplers enhaltend eine abspaltbare, bleichbeschleunigende Gruppe Download PDF

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Publication number
EP0193389B2
EP0193389B2 EP19860301365 EP86301365A EP0193389B2 EP 0193389 B2 EP0193389 B2 EP 0193389B2 EP 19860301365 EP19860301365 EP 19860301365 EP 86301365 A EP86301365 A EP 86301365A EP 0193389 B2 EP0193389 B2 EP 0193389B2
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Prior art keywords
coupler
bleach accelerator
moiety
layer
group
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EP19860301365
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English (en)
French (fr)
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EP0193389A2 (de
EP0193389A3 (en
EP0193389B1 (de
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Jeffrey Louis Hall
Kenneth Norman Kilminster
Robert Fogg Romanet
Richard Peter Szajewski
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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
    • G03C7/305—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
    • G03C7/30552—Mercapto

Definitions

  • This invention relates to photographic materials and processes which utilize a compound capable of releasing a bleach accelerator moiety.
  • Photographic materials useful for forming dye images by means of a process which includes a bleaching step are known and used commercially. Such materials and processes are described in, for example. The Theory of the Photographic Process , 4th Edition, Edited by T. H. James, 1977, pages 462-463 and pages 335-361. The use in such photographic materials of a bleach accelerator releasing coupler is described in Research Disclosure , 1973, Item No. 11449.
  • the bleach accelerator releasing coupler also known as a BARC, has contained a heterocyclic group as the bleach accelerator moiety which is released during processing of the photographic element. These bleach accelerator releasing couplers cause an undesired degree of adverse development effects.
  • Couplers which have a thioether group at the coupling position have been known in the photographic art. Examples of such couplers are described in, for example, U.S. Patent 4,387,159, Japanese Published Patent Application 57-173836, U.S. Patent 3,227,554 and U.S. Patent 4,293,691. These compounds have been useful as development inhibitor releasing (DIR) couplers. Almost all of the couplers that are designed as development inhibitor releasing couplers have a thioether group and are oleophilic in order to help maintain the coupler in one location in the hydrophilic emulsion layers of the photographic material. Typically such couplers have ballast groups for this purpose. These have not required a balance of a strong affinity for silver and a balance of water solubility as is the case with bleach accelerator compounds.
  • DIR development inhibitor releasing
  • the present invention provides use of a coupler comprising a coupler moiety having a releasable bleach accelerator moiety represented by the formula: -(TIME) n -S-R1-R2 wherein TIME is a timing group; n is 0 or 1; R1 is a linking group consisting of alkylene comprising 1 to 8 carbon atoms; and, R2 is a water solubilizing group, as a bleach accelerator releasing coupler in a photographic element comprising a support, a photographic silver halide emulsion layer and the bleach accelerator releasing coupler incorporated in the emulsion layer or a layer adjacent thereto.
  • TIME is a timing group
  • n is 0 or 1
  • R1 is a linking group consisting of alkylene comprising 1 to 8 carbon atoms
  • R2 is a water solubilizing group
  • the releasable bleach accelerator moiety is in a location on the compound carrying the moiety which enables release of the bleach accelerator moiety at time during processing of the photographic element which enables acceleration of the bleaching step.
  • the bleach accelerator releasing compound is preferably a coupler having the bleach accelerator moiety in the coupling position.
  • the coupler can be, but need not be, a dye-forming coupler.
  • One embodiment of the invention is a silver halide photographic element containing a bleach accelerator releasing compound which has a releasable bleach accelerator moiety as described.
  • Coupler refers to the entire compound including the coupler moiety and the bleach accelerator moiety (TIME) n -S-R1-R2.
  • TIME bleach accelerator moiety
  • coupler moiety refers to that portion of the compound other than the bleach accelerator moiety.
  • the particular R1 group linking the sulfur atom and the water solubilizing group R2 can be varied to control such parameters as water solubility, diffusivity, silver affinity, silver ion complex solubility, silver development effects and other sensitometric effects. Since these parameters can be controlled by modification of R1, they need not be emphasized in selecting a particular coupler moiety and the particular water solubilizing group, but provide freedom in selecting such moieties and groups for a particular photographic element and process.
  • the bleach accelerator fragment is released at an appropriate time as a unit. That is, -S-R1-R2 is released as a unit.
  • the rate and total time of difussion of the bleach accelerator fragment in the photographic element must be such as to enable bleach acceleration in the appropriate layers of the photographic element during processing.
  • the timing group when present, also releases -S-R1-R2 as a unit.
  • Selection of R1 and R2 can also influence the rate and total time of release of the bleach accelerator moiety from the remainder of the compound, preferably the remainder of the coupler. It is necessary that the bleach accelerator moiety not adversely effect the processing steps and the photographic element.
  • Preferred photographic couplers used in the invention are represented by the formula: wherein COUP is a coupler moiety; m is 1 to 8; R3 and R4 are individually hydrogen or alkyl containing 1 to 4 carbon atoms; and wherein the total number of carbon atoms in is 1 to 8.
  • Alkyl includes straight or branched chain alkyl, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, and t-butyl.
  • the coupler moiety can be any moiety that will react with oxidized color developing agent to enable release of the bleach accelerator moiety.
  • the coupler moiety includes coupler moieties which are useful in conventional dye-forming couplers whrch yield dyes on reaction with oxidized color developing agents as well as coupler moieties which yield colorless products on reaction with oxidized color developing agents.
  • the coupler moiety can be unballasted or ballasted with an oil-soluble group. It can be monomeric, or it can form part of a dimeric, oligomeric or polymeric coupler, in which case more than one bleach accelerator moiety can be contained in the coupler. Each coupling position can release a bleach accelerator moiety.
  • the reaction product of the coupler moiety and oxidized color developing agent can be: (1) colored and nondiffusible, in which case it will remain in the location where it is formed; (2) colored and diffusible, in which case it may be removed during processing from the location where it is formed or allowed to migrate to a different location; or (3) colorless and diffusible or nondiffusible, in which case it will not contribute to image density.
  • the reaction product may be initially colored and/or nondiffusible but converted to colorless and/or diffusible products during the course of processing.
  • the bleach accelerator moiety is attached at the coupling position of the coupler moiety which enables the bleach accelerator moiety to be displaced upon reaction of the coupler with oxidized color developing agent.
  • the bleach accelerator moiety can be bonded to the remainder of the organic compound through a timing group (TIME).
  • TIME in the described structures is a group which enables the time release of -S-R1-R2 from COUP.
  • the timing mechanism can be any timing mechanism which is useful for releasing photographically useful groups from coupler moieties.
  • the timing mechanism can be as described in, for example U.S. Patent 4,248,962 or U.S. 4,409,323.
  • Release of the bleach accelerator moiety can involve a single reaction or it can involve sequential reactions. For example, two or more sequential reactions may be required within a TIME group to effect release of the bleach accelerator moiety.
  • the TIME group can have two bleach accelerator moieties bonded to different locations on the TIME group so that upon release of the TIME group from the coupler moiety two reactions can occur sequentially enabling sequential release of the two bleach accelerator moieties.
  • Another example is a reaction in the TIME group which may release a second coupler moiety which contains another timing group to which a photographically useful group is attached and from which it is released after the second coupler moiety reacts with oxidized color developing agent.
  • the TIME group can contain moieties and substituents which will permit control of one or more of the rates of reaction of COUP with oxidized color developing agent, the rate of diffusion of -TIME-S-R1-R2 once it is released from COUP and the rate of release of -S-R1-R2.
  • the TIME group can contain added substituents, such as added photographically useful groups which can remain attached to the timing group and be released independently.
  • the TIME groups can contain a ballast group.
  • R2 groups are examples of useful water solubilizing groups wherein R5 is H or alkyl of 1 to 4 carbons, R6 is alkyl of 1 to 4 carbons and wherein at least one of R5 and R6 is alkyl, and the total carbon atoms in R5 and R6 is no more than 8.
  • couplers are phenols and naphthols which form cyan dyes on reaction with oxidized color developing agents and have the releasable bleach accelerator moiety attached at the coupling position, that is the carbon atom in the 4-position of the coupler moiety.
  • R8, R9, R10, R11 and R12 individually represent ballast groups; R7 and R9, individually represent at least one halogen atom, such as chloro or fluoro; alkyl, such as alkyl containing 1 to 4 carbon atoms, for example methyl, ethyl, propyl or butyl; or alkoxy, such as alkoxy containing 1 to 4 carbon atoms, for example methoxy, ethoxy, propoxy and butoxy.
  • magenta dye-forming couplers are pyrazolones and pyrazolotriazoles which form magenta dyes upon reaction with oxidized color developing agents.
  • Structures of preferred magenta dye-forming couplers are: wherein R14, R16 and R17 are individually aryl, alkyl, such as alkyl containing 1 to 30 carbon atoms; and R13, R15 and R18 are individually ballast groups, or are phenyl or substituted phenyl, such as 2,4,6-trihalophenyl, for example 2,4,6-trichlorophenyl.
  • magenta dye-forming couplers examples include:
  • Couplers which form yellow dyes upon reaction with oxidized color developing agents are described in such representative patents as: U.S. Patent Nos. 2,875,057; 2,407,210; 3,265,506; 2,298,443; 3,048,194; and 3,447,928.
  • yellow dye-forming couplers are acylamides, for example, benzoylacetanilides and pivalylacetanilides.
  • yellow dye-forming couplers are: wherein R21, R23 and R25 are individually ballast groups; and R19, R20, R22 and R24 are individually hydrogen or one or more haqlogen, such as chlorine and fluoride; alkyl, such as alkyl containing 1 to 4 carbon atoms, for example methyl, ethyl, propyl and butyl; alkoxy, such as alkoxy containing 1 to 20 carbon atoms; or a ballast group.
  • yellow dye-forming couplers examples are:
  • Couplers which form colorless products or form products which do not significantly absorb electromagnetic radiation within the visible range of the spectrum are described in such representative patents as: U.K. Patent No. 861,138; U.S. Patent Nos. 3,632,345; 3,928,041; 3,958,993; and 3,961,959.
  • couplers are cyclic carbonyl containing compounds which form colorless products on reaction with oxidized color developing agents.
  • Couplers which form black dyes upon reaction with oxidized color developing agents are described in such representative patents as: U.S. Patent Nos. 1,939,231; 2,181,944; 2,333,106; 4,429,035; 4,439,518; 4,254,213; 4,387,158; 4,126,461 and 4,200,466.
  • couplers are resorcinols or m-aminophenols which form black products on reaction with oxidized color developing agents.
  • Structures of preferred couplers capble of forming a black dye are : wherein R31 and R32 are individually alkyl, such as alkyl containing 3 to 20 carbon atoms, phenyl or phenyl substituted with hydroxy, halo, such as chloro or bromo, amino, alkyl, such as alkyl containing 1 to 20 carbon atoms, or alkoxy, such as alkoxy containing 1 to 20 carbon atoms; and R33 and R34 are individually hydrogen, alkyl such as alkyl containing 1 to 20 carbon atoms, alkenyl, such as alkenyl containing 1 to 20 carbon atoms, or aryl, such as aryl containing 6 to 20 carbon atoms; and, R35 is one or more halogen, such as chlorine or bromine, alkyl, such as alkyl containing 1 to
  • couplers capable of forming a black dye are:
  • TIME groups which are useful enable relase of the bleach accelerator moiety at the appropriate time during processing, that is at the time which enables accelerated bleaching of the photographic element. Examples of such TIME groups are:
  • the bleach accelerator releasing coupler can be used in combination with a colorless coupler or a colored coupler and added to a silver halide emulsion together with an image dye-forming coupler, or alternatively in the form of an independent emulsion in an auxiliary layer, such as an intermediate layer and/or an undercoat layer.
  • the bleach accelerator releasing compounds are useful alone or in combinations with two or more bleach accelerator releasing compounds.
  • the bleach accelerator releasing couplers can be incorporated in photographic elements so that upon development of an exposed photographic element they will be in reactive association with oxidized color developing agent.
  • Coupler compounds incorporated in photographic processing solutions should be of such molecular size and configuration that they will diffuse through photographic layers with the processing solution.
  • the coupler compounds should be nondiffusible; that is, they should be of such molecular size and configuration that they will not significantly diffuse or wander from the layer which they are coated.
  • Photographic elements in which the photographic couplers 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 coupler compounds can be incorporated in the silver halide emulsion layer or in another 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 development inhibitor releasing (DIR) couplers, color forming couplers and colored masking couplers. These other photographic coupler compounds can form dyes of the same or different color and hue as the bleach accelerator releasing compounds. Additionally, the silver halide emulsion layer can contain addenda conventionally contained in such layers.
  • DIR development inhibitor releasing
  • a typical multilayer, multicolor photographic element used in this invention 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 therewith the bleach accelerator releasing compound.
  • Each silver halide emulsion unit can be composed of one or more layers and the various units and layers can arranged in different locations with respect to one another. Typical arrangements are described in U.S. Patent Nos.
  • the coupler compounds can be incorporated in or associated with one or more layers or units of the element.
  • the layer(s) and unit(s) affected by the bleach accelerator moiety can be controlled by incorporating in appropriate locations in the element scavenger layer(s) which will confine the action of the bleach accelerator moiety to the desired layer(s) or unit(s).
  • 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 emulsion can be negative-working or a direct-positive emulsion. They can form latent images predominantly on the surface of the silver halide grains or predominantly in the interior of the silver halide grains. They can be chemically and spectrally sensitized.
  • the emulsions typically will be gelatin emulsions although other hydrophillic colloids can be used in accordance with usual practice.
  • Tabular grain photographic silver halide emulsions described in, for example, Research Disclosure , January 1983, Item No. 22534 and U.S. Patent 4,434,226 are particularly useful.
  • 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 and the like. Typically, flexible support is employed, such as a polymeric film or paper support. Paper supports can be acetylated or caoted with baryta and/or an ⁇ -olefin polymer, particularly a polymer of an ⁇ -olefin containing 2 to 10 carbon atoms such as polyethylene, polypropylene, ethylene-butene copolymers and the like.
  • the coupler moiety is a dye-forming coupler, it can react with oxidized developing agent in the same or an adjacent layer to form a dye of the same or different color or hue as that obtained from the primary coupler. If the coupler moiety is a competing coupler, it can react with oxidized color developing agent in the same or an adjacent layer to reduce dye density.
  • bleach accelerator releasing compound The optimum concentration range of bleach accelerator releasing compound will depend upon such factors as the desired image, the location of the bleach accelerator releasing compound, processing conditions, the particular bleach composition, the particular layers of the photographic element, processing steps and the particular bleach accelerator moiety.
  • a typical concentration of bleach accelerator releasing compound in a photographic element is within the range of about 50 to about 500 mg/sq meter.
  • a particularly useful photographic element is a dye-forming photographic element having a layer format known to be useful in forming a multicolor image by a subtractive color process. Any or all of the respective color records can be in the form of a double or triple layer structure.
  • the process of forming a dye image in a photographic element as described comprises conventional color processing involving a bleaching step.
  • the bleaching step is preferably conducted separately from fixing.
  • the bleaching composition comprises known bleaching agents. Examples of typical processes are described in Research Disclosure , December 1978, Item No. 17643 and in "Modern Photographic Processing", by Grant Haist, Vol. 2, pages 569-587, John Wiley and Sons, N.Y., 1979.
  • Processing of a dye-forming photographic element according to the invention typically comprises a color development step, a bleaching step and a fixing step.
  • the bleaching step and fixing step can be combined into one step if desired.
  • processing steps which are also useful in this process include a pre-hardening step, a neutralization step, a first development step (black-and-white development), a stabilizing step, and water washing step. Processing steps are typically carried out at a temperature within the range of 18°C to 60°C.
  • the bleach accelerator releasing compounds are prepared by organic synthesis procedures known in the organic compound synthesis art.
  • the coupler moiety can be reacted with the bleach accelerator moiety in an appropriate solvent.
  • the following are representative preparations of bleach accelerator releasing couplers:
  • the desired product is extracted with diethyl ether to obtain, after crystallization, the desired bleach accelerator releasing coupler which is a colorless solid having a melting point of 139°C to 141°C.
  • the product is also identified by elemental and spectral analysis.
  • a multilayer color photographic element designated herein as Sample a, was prepared by coating the following layers on a cellulose triacetate film support in the designated order (levels coated are given in mg/m2 with silver halide stated as silver level):
  • Samples b, d, f, and h were prepared in the same manner as for Sample a except that coupler C-2 in Layer 2 was replaced by the amounts indicated in Table 1 of comparison coupler C-4, and bleach accelerator releasing couplers designated as BARC-1, -2, or -3, respectively. Further, Samples c, e, g and i were similarly prepared by replacing half of coupler C-1 in Layer 1 of Sample a by the indicated amounts of comparison coupler C-4 and BAR couplers 1, 2, or 3, respectively. These samples were each given a white light exposure through a graduated density step tablet and processed for 3.25 minutes in a color developer of the type described in the British Journal of Photography Annual, 1979, pp. 204-206. From plots of density to red light vs.
  • BARC-1 herein is: BARC-2 herein is: BARC-3 herein is:
  • Multilayer incorporated coupler photographic elements were prepared in the same manner as for Sample a of Example 1, with coated amounts given in mg/m2.
  • Control Sample j was coated as follows on the film support:
  • Sample m was prepared as for Sample j but adding bleach accelerator releasing couplers to both cyan and magenta layers 1, 2, 4 and 5 according to the changes indicated in preparing Samples k and l.
  • Example 1 The following examples can be carried out according to Example 1 with the exception that the bleach accelerator releasing coupler is replaced by the bleach accelerator releasing coupler designated in the following examples:

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Claims (7)

  1. Verwendung eines Kupplers mit einem Kupplerrest mit einem freisetzbaren Bleichbeschleunigerrest der Formel:

            -(TIME)n-S-R₁-R₂

    worin bedeuten:
    TIME eine Zeitgebergruppe;
    n gleich 0 oder 1;
    R₁ eine verbindende Gruppe, bestehend aus Alkylen mit 1 bis 8 Kohlenstoffatomen; und
    R₂ eine wasserlöslich machende Gruppe,
    als einen einen Bleichbeschleuniger freisetzenden Kuppler in einem photographischen Element mit einem Träger, einer photographischen Silberhalogenidemulsionsschicht und dem einen Bleichbeschleuniger freisetzenden Kuppler in der Emulsionsschicht oder einer hierzu benachbarten Schicht.
  2. Verwendung nach Anspruch 1, wobei die wasserlöslich machende Gruppe eine Carboxygruppe ist.
  3. Verwendung nach Anspruch 1, wobei der den Bleichbeschleuniger freisetzende Kuppler durch die folgende Formel wiedergegeben wird:
    Figure imgb0074
     worin bedeuten:
    COUP einen Kupplerrest;
    m gleich 1 bis 8;
    R₃ und R₄ einzeln Wasserstoff oder Alkyl mit 1 bis 4 Kohlenstoffatomen, wobei die Gesamtanzahl von Kohlenstoffatomen in dem Rest
    Figure imgb0075
     bei 1 bis 8 liegt.
  4. Verwendung nach Anspruch 1, wobei die Gruppe -S-R₁-R₂ entspricht -S-CH₂CH₂-COOH und worin n gleich 0 ist.
  5. Verwendung nach Anspruch 3, wobei der einen Bleichbeschleuniger freisetzende Kuppler eine Verbindung der folgenden Formel ist:
    Figure imgb0076
  6. Verwendung nach Anspruch 3, wobei der einen Bleichbeschleuniger freisetzende Kuppler eine Verbindung der folgenden Formel ist:
    Figure imgb0077
  7. Photographisches Element mit einem Träger, einer photographischen Emulsionsschicht mit tafelförmigen Silberhalogenidkörnern sowie einem einen Bleichbeschleuniger freisetzenden Kuppler nach einem der Ansprüche 1 bis 6 in der Emulsionsschicht oder einer hierzu benachbarten Schicht.
EP19860301365 1985-02-28 1986-02-26 Verwendung eines Kupplers enhaltend eine abspaltbare, bleichbeschleunigende Gruppe Expired - Lifetime EP0193389B2 (de)

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US70711585A 1985-02-28 1985-02-28
US707115 1985-02-28

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EP0193389A2 EP0193389A2 (de) 1986-09-03
EP0193389A3 EP0193389A3 (en) 1988-11-23
EP0193389B1 EP0193389B1 (de) 1990-10-24
EP0193389B2 true EP0193389B2 (de) 1995-03-15

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JP (1) JPH0823673B2 (de)
CA (1) CA1287765C (de)
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Publication number Priority date Publication date Assignee Title
JPH0820707B2 (ja) * 1986-09-11 1996-03-04 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
JPS63121845A (ja) * 1986-11-12 1988-05-25 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料及びその処理方法
JPS63301950A (ja) * 1987-01-19 1988-12-08 Konica Corp ハロゲン化銀カラー写真感光材料
JPS63216048A (ja) * 1987-03-05 1988-09-08 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
DE3853222T2 (de) * 1987-04-14 1995-06-29 Fuji Photo Film Co Ltd Verfahren zur Behandlung eines photographischen Silberhalogenidmaterials.
JPH0192747A (ja) * 1987-06-15 1989-04-12 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JP2543705B2 (ja) * 1987-06-25 1996-10-16 富士写真フイルム株式会社 ハロゲン化銀カラ−写真感光材料
JP2542858B2 (ja) * 1987-07-27 1996-10-09 富士写真フイルム株式会社 ハロゲン化銀カラ―写真感光材料の処理方法
JPH01131561A (ja) * 1987-08-13 1989-05-24 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
EP0310125B1 (de) * 1987-10-02 1995-04-19 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
JPH01108546A (ja) 1987-10-22 1989-04-25 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JP2553890B2 (ja) * 1987-10-29 1996-11-13 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
JPH01140153A (ja) 1987-11-27 1989-06-01 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JPH07117725B2 (ja) * 1987-11-30 1995-12-18 コニカ株式会社 粒状性に優れた色素画像が得られるハロゲン化銀カラー写真感光材料の処理方法
JPH0833628B2 (ja) 1987-12-15 1996-03-29 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
JP2684374B2 (ja) * 1988-01-20 1997-12-03 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
JP2528344B2 (ja) * 1988-02-10 1996-08-28 富士写真フイルム株式会社 ハロゲン化銀カラ―写真感光材料
JPH01213650A (ja) * 1988-02-20 1989-08-28 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
JPH01223454A (ja) * 1988-03-03 1989-09-06 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JP2565368B2 (ja) * 1988-03-09 1996-12-18 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
CA1338080C (en) * 1988-06-21 1996-02-27 Drake Matthew Michno Photographic materials having releasable compounds
US4859578A (en) * 1988-06-21 1989-08-22 Eastman Kodak Company Photographic recording material providing improved granularity properties
US4912024A (en) * 1988-06-21 1990-03-27 Eastman Kodak Company Photographic material having releasable compound
JP2565383B2 (ja) * 1988-09-29 1996-12-18 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
EP0365348A3 (en) * 1988-10-20 1990-11-14 Konica Corporation A silver halide color photographic light-sensitive material
JPH0354547A (ja) * 1989-07-24 1991-03-08 Konica Corp 保存性が良好なハロゲン化銀写真感光材料
EP0435334B1 (de) 1989-12-29 1997-11-05 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial, das einen gelb gefärbten Cyan-Kuppler enthält
DE69127002T2 (de) 1990-01-31 1997-11-20 Fuji Photo Film Co Ltd Farbphotographisches Silberhalogenidmaterial
JPH04445A (ja) 1990-04-17 1992-01-06 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
EP0458131B1 (de) 1990-05-09 1997-08-06 Fuji Photo Film Co., Ltd. Photographische Verarbeitungszusammensetzung und diese verwendendes Verarbeitungsverfahren
DE69131785T2 (de) 1990-08-20 2000-05-11 Fuji Photo Film Co Ltd Datenbehaltendes photographisches Filmerzeugnis und Verfahren zur Herstellung eines Farbbildes
US5135839A (en) * 1990-11-13 1992-08-04 Eastman Kodak Company Silver halide material with dir and bleach accelerator releasing couplers
US5525460A (en) 1992-03-19 1996-06-11 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion and light-sensitive material using the same
JP2777949B2 (ja) 1992-04-03 1998-07-23 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
EP0574090A1 (de) 1992-06-12 1993-12-15 Eastman Kodak Company 1-Äquivalentkuppler und freisetzbaren Farbstoffen mit niedrigem pKa
US5358828A (en) * 1992-06-29 1994-10-25 Eastman Kodak Company Photographic element and process comprising a bleach accelerator releasing compound
US5286859A (en) * 1992-06-29 1994-02-15 Eastman Kodak Company Method of forming a photographic washout coupler (BARC) using a strong base
US5300406A (en) * 1992-06-29 1994-04-05 Eastman Kodak Company Photographic element comprising a combination of a development inhibiting releasing coupler and a bleach accelerator releasing compound
US5318879A (en) * 1992-06-29 1994-06-07 Eastman Kodak Company Photographic element comprising a bleach accelerator releasing compound
US5385815A (en) 1992-07-01 1995-01-31 Eastman Kodak Company Photographic elements containing loaded ultraviolet absorbing polymer latex
US5407791A (en) 1993-01-18 1995-04-18 Fuji Photo Film Co., Ltd. Silver halide photographic material
DE69423374T2 (de) * 1993-01-29 2000-12-28 Eastman Kodak Co Fotografisches Material und Verfahren mit einem Thiol-Bleich-Hilfsmittel in der gering-empfindlichen Schicht einer Dreifach-Beschichtung
US5506094A (en) * 1993-07-28 1996-04-09 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5514530A (en) * 1993-07-28 1996-05-07 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5521057A (en) * 1993-07-28 1996-05-28 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yeilding dyes resistant to crystallization and reduction
US5510235A (en) * 1993-07-28 1996-04-23 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
EP0654705B1 (de) 1993-11-24 2000-06-21 Fuji Photo Film Co., Ltd. Photographische Verarbeitungszusammensetzung und Verarbeitungsverfahren
EP0684511B1 (de) 1994-05-20 2001-02-28 Eastman Kodak Company Niedrigkontrastfilm
DE69516332T2 (de) 1994-06-08 2000-11-30 Eastman Kodak Co Farbphotographisches Element, das neue Epoxy-Abfänger für restlichen Purpurrot-Kuppler enthält
EP0695968A3 (de) 1994-08-01 1996-07-10 Eastman Kodak Co Viskositätsverminderung in einer photographischen Schmelze
US5476760A (en) 1994-10-26 1995-12-19 Eastman Kodak Company Photographic emulsions of enhanced sensitivity
US5585228A (en) 1994-11-30 1996-12-17 Eastman Kodak Company Benzotriazole based UV absorbing compounds and photographic elements containing them
US5561031A (en) * 1995-03-23 1996-10-01 Eastman Kodak Company Color reversal elements with incorporated bleach accelerator
EP0762198B1 (de) 1995-08-02 2000-10-04 Eastman Kodak Company Filterfarbstoffe enthaltende photographische Elemente
DE69519571T2 (de) * 1995-09-18 2001-04-05 Tulalip Consultoria Com Socied Verfahren zur Herstellung von 4-Mercapto-1-naphtol-Verbindungen
US5723280A (en) 1995-11-13 1998-03-03 Eastman Kodak Company Photographic element comprising a red sensitive silver halide emulsion layer
US6183944B1 (en) 1995-11-30 2001-02-06 Eastman Kodak Company Aggregated dyes for radiation-sensitive elements
DE69731568T2 (de) 1996-01-26 2005-12-22 Eastman Kodak Co. Lichtempfindliche Silberhalogenidemulsionschicht mit gesteigerter photographischer Empfindlichkeit
US5747235A (en) 1996-01-26 1998-05-05 Eastman Kodak Company Silver halide light sensitive emulsion layer having enhanced photographic sensitivity
US5747236A (en) 1996-01-26 1998-05-05 Eastman Kodak Company Silver halide light sensitive emulsion layer having enhanced photographic sensitivity
JP3584119B2 (ja) 1996-04-05 2004-11-04 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
EP0816917B1 (de) * 1996-06-26 2002-09-18 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Farbphotographisches Silberhalogenidelement mit verbesserter Bleichbarkeit
EP0878735B1 (de) * 1997-05-15 2003-03-19 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Farbphotographisches Silberhalogenidelement mit verbesserter Bleichbarkeit
ITSV20000026A1 (it) 2000-06-21 2001-12-21 Ferrania Spa Elemento fotografico a colori
US6520694B1 (en) 2002-01-18 2003-02-18 Eastman Kodak Company System and method for processing photographic film images
US20130052594A1 (en) 2011-08-31 2013-02-28 Diane M. Carroll-Yacoby Motion picture films to provide archival images

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5149725A (de) * 1974-10-25 1976-04-30 Konishiroku Photo Ind
DD142764A1 (de) * 1979-04-04 1980-07-09 Horst Engelmann Lichtempfindliches,farbfotografisches silberhalogenidmaterial mit dir-kupplern
US4387159A (en) * 1980-05-29 1983-06-07 Veb Filmfabrik Wolfen Light sensitive, color photographic silver halide compositions with DIR-couplers
JPS57173836A (en) * 1981-04-20 1982-10-26 Konishiroku Photo Ind Co Ltd Silver halide color photographic material

Also Published As

Publication number Publication date
JPH0823673B2 (ja) 1996-03-06
EP0193389A2 (de) 1986-09-03
DE3675034D1 (de) 1990-11-29
CA1287765C (en) 1991-08-20
EP0193389A3 (en) 1988-11-23
EP0193389B1 (de) 1990-10-24
JPS61201247A (ja) 1986-09-05

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