EP0443530B1 - Matériau photographique et procédé comprenant un coupleur naphtol enlevable par lavage - Google Patents

Matériau photographique et procédé comprenant un coupleur naphtol enlevable par lavage Download PDF

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Publication number
EP0443530B1
EP0443530B1 EP19910102367 EP91102367A EP0443530B1 EP 0443530 B1 EP0443530 B1 EP 0443530B1 EP 19910102367 EP19910102367 EP 19910102367 EP 91102367 A EP91102367 A EP 91102367A EP 0443530 B1 EP0443530 B1 EP 0443530B1
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group
photographic
coupler
coupling
naphtholic
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English (en)
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EP0443530A2 (fr
EP0443530A3 (en
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William James C/O Eastman Kodak Company Begley
Teh Hsuan C/O Eastman Kodak Company Chen
Hans Gway C/O Eastman Kodak Company Ling
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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
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
    • G03C7/30523—Phenols or naphtols couplers

Definitions

  • This invention relates to a new photographic naphtholic coupler capable upon oxidative coupling of forming a dye that is capable of being washed out of the photographic material containing the coupler upon processing and to photographic materials and processes comprising the naphtholic coupler.
  • couplers are known in photographic materials and processes.
  • One of the classes of photographic couplers includes naphtholic couplers that typically form cyan dyes upon oxidative coupling in photographic materials and processes. These naphtholic couplers typically form cyan dyes upon oxidative coupling with color developing agents.
  • Such naphtholic couplers are also known which are capable of forming dyes upon oxidative coupling that can be washed out of the photographic material upon processing. These naphtholic couplers are described in, for example, U.S. Patent 4,482,629.
  • the naphtholic couplers that are capable of forming dyes that can be washed out of the photographic material upon photographic processing contain a water solubilizing group, such as a carboxy group or sulfonic acid group, substituted on a group in the 2- position of the naphtholic coupler. It has been desirable to provide a naphtholic coupler that is not as expensive to manufacture as the described naphtholic couplers and still provides a useful dye that can be washed out of the photographic material with the added advantage that the coupler enables a lower concentration of coupler to be used in a photographic element without significantly changing imaging results.
  • a water solubilizing group such as a carboxy group or sulfonic acid group
  • the present invention solves these problems by providing a photographic material comprising a support bearing at least one photographic silver halide emulsion layer and having in or adjacent the emulsion layer an immobile naphtholic coupler capable upon oxidative coupling of forming a dye that is capable of being washed out of the photographic element upon photographic processing, wherein the immobile naphtholic coupler comprises a ballast free naphtholic coupler moiety comprising a -CONH2 group in the 2- position and a ballasted coupling-off group in the 4- position.
  • the ballasted coupling-off group preferably comprises a releasable photographically useful group (PUG).
  • the immobile naphtholic coupler is typically represented by the formula: wherein Z is a ballasted coupling-off group, R1 is a ballast-free substituent that does not adversely affect the desired properties of the coupler and dye, and z is 0, 1, 2 or 3. R1 does not comprise a ballast group because such a group adversely affects wash-out properties of the dye formed from the naphtholic coupler.
  • the ballasted coupling-off group (Z) enables the naphtholic coupler to be immobile in the photographic material prior to exposure and processing.
  • the naphtholic coupler reacts with oxidized color developing agent to form a dye that is washed out of the element during processing.
  • the coupling-off group is released during processing.
  • the portion of the coupling-off group containing the ballast group remains in the location in which it was coated.
  • the coupling-off group preferably comprises a releasable photographically useful group (PUG) which is released upon photographic processing.
  • the PUG either is immobilized to remain in the location of the element in which it was coated or the PUG is mobile to allow it, after release, to move to a location in the element at which it can serve its intended function.
  • a preferred naphtholic coupler as described comprises a coupling-off group represented by the formula: -(LINK) n -(TIME) m -PUG wherein
  • a process of forming an image having the described advantages comprises developing an exposed photographic element as described by means of a color developing agent in the presence of the described naphtholic coupler and washing-out the dye formed from the naphtholic coupler.
  • Any naphtholic coupler moiety is useful that can contain the -CONH2 group in the 2- position and a coupling-off group in the 4- position and can form a compound, especially a dye, that can be washed out of the element upon oxidative coupling of the coupler. It will be appreciated that depending upon the particular developing agent and the particular type of processing, the reaction product of the coupler moiety and the oxidized developing agent can be colored or colorless. Examples of useful naphtholic coupler moieties can be unsubstituted except for the required substituents in the 2- and 4- positions as described.
  • the naphtholic coupler moieties in addition to the substituents in the 2- and 4- positions can contain other substituents that do not adversely affect the desired properties of the element and coupler.
  • substituents include 5-NHSO2CH3, 5-NHCOCH3 or 6-NHSO2CH3.
  • Useful naphtholic coupler moieties include those described in, for example, the following patents in which the group described in the 2- position is replaced with -CONH2, especially those having a ballasted coupling-off group: U.S. Patents 4,840,884; 4,861,701; 2,474,293; 3,227,554; 4,482,629 and 4,857,447.
  • any coupling-off group containing a ballast group known in the photographic art is useful in the 4- position of the described naphtholic coupler moiety.
  • Examples of useful coupling-off groups are described in, for example, U.S. Patent 4,861,701.
  • Preferred coupling-off groups are those that enable release of a PUG upon photographic processing, especially those that have a releasable timing group between the bond to the coupling position of the coupler and the releasable PUG.
  • Preferred timing groups are described in, for example, U.S. Patents 4,861,701; 4,248,962; 4,409,323; 4,482,629 and 4,857,447.
  • a preferred naphtholic coupler is represented by formula: wherein
  • T is, for example, a group that enables release of PUG by means of intramolecular nucleophilic displacement, such as described in U.S. 4,248,962 and U.S. 4,861,701.
  • reaction of the coupler with oxidized color developing agent cleaves the bond between the coupler and the coupling-off group. Then the bond between the PUG and the remainder of the coupling-off group is cleaved. Bond cleavage between the PUG and the remainder of the coupling-off group preferably does not involve the action of oxidized color developing agent.
  • the cleavage of the bond between the PUG and the remainder of the coupling-off group can involve any reaction known in the photographic art for cleavage of such groups, for example an intramolecular nucleophilic displacement reaction or other elimination reaction.
  • ballast group any ballast group known in the photographic art can be useful on the coupling-off group.
  • the ballast group (BALL) herein means an organic group of such size and configuration as to confer on the coupler molecule sufficient bulk to render the coupler substantially non-diffusible from the layer in which it is coated in a photographic element prior to exposure and processing.
  • Representative ballast groups include substituted or unsubstituted alkyl or aryl groups containing, for example, 8 to 40 carbon atoms.
  • Other useful ballast groups include sulfonamido groups containing 8 to 40 carbon atoms, carbonamido, carbamoyl, sulfamoyl, ester, sulfone, ether, thioether and amino groups.
  • a typical timing group T is a group that enables release of a PUG by means of intramolecular nucleophilic displacement, such as described in U.S. Patents 4,861,701; 4,857,440; 4,847,185 and 4,248,962.
  • Illustrative timing groups T are as follows: and other illustrative groups described in U.S. Patent 4,857,447.
  • R4, R5, R6, R 6a , R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23 and R24 individually are hydrogen or substituents that do not adversely affect the desired properties of the naphtholic coupler or dye formed, such as unsubstituted or substituted alkyl, for example, methyl, ethyl, propyl, n-butyl, t-butyl and eicosyl, or unsubstituted or substituted aryl, such as phenyl, or substituted phenyl, and PUG is a releasable photographically useful group. At least one of the described groups on the coupling-off group is a ballast group.
  • naphtholic coupler refers to the entire compound including the coupler moiety and the coupling-off group.
  • naphtholic coupler moiety refers to that portion of the coupler other than the coupling-off group.
  • the PUG can be any group that is typically made available in a photographic element in an imagewise fashion.
  • the PUG can be a photographic 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 a desensitizer.
  • a development inhibitor
  • the PUG 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 PUG can be for example a preformed development inhibitor or the development inhibiting function can be blocked by being the point of attachment to the carbonyl group bonded to PUG in the coupling-off group.
  • Other examples are a preformed dye, a dye that is blocked to shift its absorption, and a leuco dye.
  • a preferred naphtholic coupler as described is a photographic coupler containing a naphtholic coupler moiety and a PUG containing a hetero atom from VIb or Vb of the Periodic Table having a negative valence of 2 or 3 bonded to a carbonyl group of the coupling-off group.
  • Couplers which form cyan dyes upon reaction with oxidized color developing agents are described in such representative patents and publications as: U.S. Pat. Nos. 2,772,162; 2,895,826; 3,002,836; 3,034,892; 2,474,293; 2,423,730; 2,367,531; 3,041,236; 4,333,999 and "Farbkuppler-eine LiteraturREMsicht,” published in Agfa Mitannonen, Band III, pp. 156-175 (1961).
  • couplers are phenols and naphthols that form cyan dyes on reaction with oxidized color developing agents.
  • Couplers which form magenta dyes upon reaction with oxidized color developing agent are described in such representative patents and publications as: U.S. Pat. Nos. 2,600,788; 2,369,489; 2,343,703; 2,311,082; 3,152,896; 3,519,429; 3,062,653; 2,908,573 and "Farbkuppler-eine Literaturschreibsicht,” published in Agfa Mitannonen,Band III, pp. 126-156 (1961).
  • couplers are pyrazolones and pyrazolotriazoles that form magenta dyes upon reaction with oxidized color developing agents.
  • Couplers which form yellow dyes upon reaction with oxidized and color developing agent are described in such representative patents and publications as: U.S. Pat. Nos. 2,875,057; 2,407,210; 3,265,506; 2,298,443; 3,048,194; 3,447,928 and "Farbkuppler-eine Literaturschreibsicht,” published in Agfa Mitannonen, Band III, pp. 112-126 (1961).
  • couplers are acylacetamides, such as benzoylacetanilides and pivaloylacetanilides that form yellow dyes upon reaction with oxidized color developing agents.
  • Couplers which form colorless products upon reaction with oxidized color developing agent are described in such representative patents as: U.K. Patent No. 861,138; U.S. Pat. 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 agent.
  • Preferred development inhibitors are iodide and heterocyclic compounds such as mercaptotetrazoles, selenotetrazoles, mercaptobenzothiazoles, selenobenzothiazoles, mercaptobenzoxazoles, selenobenzoxazoles, mercaptobenzimidazoles, selenobenzimidazoles, oxadiazoles, benzotriazoles and benzodiazoles.
  • R29 is unsubstituted or substituted alkyl, such as butyl, 1-ethylpentyl, and 2-ethoxyethyl, or alkylthio, such as butylthio and octylthio;
  • R25 and R26 individually are hydrogen, alkyl of 1 to 8 carbon atoms such as methyl, ethyl, or butyl, phenyl or substituted phenyl; and
  • R27 and R28 individually are hydrogen or one or more halogen such as chloro, fluoro or bromo; alkyl of 1 to 4 carbon atoms, carboxyl, esters, such as -COOCH3, or other substituents such as -NHCOOCH3, -SO2OCH3, -OCH2CH2SO2CH3, or nitro groups.
  • Suitable dyes and dye precursors include azo, azomethine, azopyrazolone, indoaniline, indophenol, anthraquinone, triarylmethane, alizarin, nitro, quinoline, indigoid and phthalocyanine dyes or precursors of such dyes such as leuco dyes, tetrazolium salts or shifted dyes. These dyes can be metal complexed or metal complexable. Representative patents describing such dyes are U.S. Pat. Nos. 3,880,658; 3,931,144; 3,932,380; 3,932,381 and 3,942,987.
  • Preferred dyes and dye precursors are azo, azomethine and indoaniline dyes and dye precursors. Structures of some preferred dyes and dye precursors are:
  • Couplers released can be nondiffusible color-forming couplers, non-color forming couplers or diffusible competing couplers.
  • Representative patents and publications describing competing couplers are: "On the Chemistry of White Couplers," by W. Püschel, Agfa-Gevaert AG Mitteilungen and der Anlagen Anlagens-Laboratorium der Agfa-Gevaert AG, Springer Verlag, 1954, pp. 352-367; U.S. Pat. Nos. 2,998,314; 2,808,329; 2,689,793; 2,742,832; German Pat. No. 1,168,769 and British Pat. No. 907,274.
  • R32 is hydrogen or alkylcarbonyl, such as acetyl
  • R33 and R34 are individually hydrogen or a solubilizing group, such as sulfo, aminosulfonyl, and carboxy
  • R35 which is the same as R34 as defined above
  • R36 is halogen, aryloxy, arylthio, or a development inhibitor, such as a mercaptotetrazole, such as phenylmercaptotetrazole or ethylmercaptotetrazole.
  • Developing agents released can be color developing agents, black-and-white developing agents or cross-oxidizing developing agents. They include aminophenols, phenylene diamines, hydroquinones and pyrazolidones. Representative patents are: U.S. Pat. Nos. 2,193,015; 2,108,243; 2,592,364; 3,656,950; 3,658,525; 2,751,297; 2,289,367; 2,772,282; 2,743,279; 2,753,256 and 2,304,953.
  • Structures of preferred developing agents are: where R37 is hydrogen or alkyl of 1 to 4 carbon atoms and R38 is hydrogen or one or more halogen such as chloro or bromo; or alkyl of 1 to 4 carbon atoms such as methyl, ethyl or butyl groups.
  • R38 is as defined above.
  • R39 is hydrogen or alkyl of 1 to 4 carbon atoms and R40, R41, R42, R43 and R44 are individually hydrogen, alkyl of 1 to 4 carbon atoms such as methyl or ethyl; hydroxyalkyl of 1 to 4 carbon atoms such as hydroxymethyl or hydroxyethyl or sulfoalkyl containing 1 to 4 carbon atoms.
  • R46 is hydrogen, alkyl, such as ethyl and butyl, alkoxy, such as ethoxy and butoxy, or alkylthio, such as ethylthio and butylthio, for example containing 1 to 6 carbon atoms, and which may be unsubstituted or substituted
  • R47 is hydrogen, alkyl or aryl, such as phenyl
  • R48 and R49 are individually alkyl, such as alkyl containing 1 to 6 carbon atoms, for example ethyl and butyl
  • z is 1 to 6.
  • the image dye-forming couplers can be incorporated in photographic elements and/or in photographic processing solutions, such as developer solutions, 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 in which they are coated.
  • 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 of 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 of 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 of this invention.
  • 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 therewith a photographic coupler of 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 couplers of this invention can be incorporated in or associated with one or more layers or units of the photographic element.
  • a layer or unit affected by PUG can be controlled by incorporating in appropriate locations in the element a scavenger layer which will confine the action of PUG to the desired layer or unit.
  • At least one of the layers of the photographic element can be, for example, a mordant layer or a barrier layer.
  • 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 and the like. Typically, 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 ⁇ -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 coupling-off group contain a releasable PUG.
  • 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.
  • Naphtholic couplers as described can be prepared by reactions and methods known in the organic compound synthesis art. Similar reactions and methods are described in U.S. Patent 4,482,629. Typically, the naphtholic coupler is prepared by the following method:
  • Ph herein means phenyl
  • Phenyl-1,4-dihydroxy-2-naphthoate (100.0 g, 356.78 mmol) was dissolved in deoxygenated tetrahydrofuran (500 mL) and deoxygenated methanol (500 mL) added. To this solution, stirred at room temperature under the nitrogen atmosphere, was added ammonium acetate (50.0 g, 648.63 mmol) followed by concentrated ammonium hydroxide (1.0 L). After stirring for 3 hours the reaction was then poured into ice cold 2N-HCl (4.0 L) and enough concentrated HCl added to bring the pH to 1. The resulting product, compound (A2) was filtered off, washed well with water and air dried. The crude product was washed with dichloromethane and air dried. Yield 62.0 g (72%).
  • the oil was taken up in a mixture of ethyl acetate, dichloromethane, heptane and acetonitrile in the ratio of 20:20:56.4, respectively and subjected to flash chromatography eluting with the same solvent system to elute impurities from the column and then changed to a ratio of 27:50:20.4 to elute the product, compound (A12).
  • the product could be recrystallized from acetonitrile. Yield 61.0 g (58%).
  • Couplers that can be prepared by these methods of synthesis include, for example:
  • Photographic elements were prepared by coating the following layers on a cellulose ester film support (amounts of each component are indicated in mg/m):
  • Strips of each element were exposed to green light through a graduated density step tablet, or through a 35% modulation fringe chart for sharpness measurements, and then developed 3.25 minutes at 38°C in the following color developer, stopped, washed, bleached, fixed, washed and dried.
  • a photographic film was prepared, exposed and processed like the film in Examples 1 - 3.
  • the processed images were read with green light to determine the contrast. From plots of the logarithm of the contrast compared to the coated level of each DIR coupler, the reactivity was determined as the amount of DIR coupler in micromoles per square meter to reduce the contrast (gamma) to half (0.5) compared to its original contrast without the presence of the DIR coupler. The smaller the amount of the DIR compound required, the higher was the reactivity of the DIR coupler.
  • Coupler 3 was as described in Example 3. The results are given in following Table II: TABLE II Example No. Coupler No. Amount of DIR Coupler to Reduce Gamma in Half (Micromoles Per Square Meter) 4 3 108 C (Comparison) C 157 D (Comparison) D 151

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Claims (8)

  1. Produit photographique aux halogénures d'argent comprenant un support recouvert d'au moins une couche d'émulsion photographique aux halogénures d'argent et contenant dans la couche d'émulsion ou dans une couche adjacente, un coupleur naphtolique immobile capable de former, au cours du couplage par oxydation un colorant pouvant être éliminé par lavage de l'élément photographique au cours du traitement photographique, dans lequel le coupleur naphtolique immobile comprend un groupement coupleur naphtolique exempt de groupes ballasts contenant un groupe -CONH₂ en position 2 et un groupe ballasté se séparant au couplage en position 4.
  2. Produit photographique tel que revendiqué dans la revendication 1, dans lequel le coupleur naphtolique immobile est représenté par la formule :
    Figure imgb0071
     où Z est un groupe ballasté se séparant au couplage ; R¹ est un substituant exempt de groupes ballasts ; et z est 0, 1, 2 ou 3.
  3. Produit photographique tel que revendiqué dans la revendication 1, dans lequel le groupe se séparant au couplage est représenté par la formule :

            -(LINK)-n-(TIME)-mPUG

    où :
    TIME est un groupe retardateur susceptible d'être libéré du groupement LINK au cours du traitement photographique de l'élément ;
    LINK est un groupe de liaison capable d'être libéré du groupement coupleur naphtolique au cours du couplage par oxydation du coupleur naphtolique ;
    n et m sont individuellement 0, 1 ou 2 ;
    PUG est un groupe utile en photographie susceptible d'être libéré ; et
    au moins un des groupes n et m est 1 ou 2.
  4. Produit photographique tel que revendiqué dans la revendication 1, dans lequel le coupleur naphtolique est représenté par la formule :
    Figure imgb0072
     où :
    X représente les atomes nécessaires pour compléter un cycle à 5, 6 ou 7 chaînons, tel qu'un groupe aryle ou hétérocyclique ;
    BALL est un groupe ballast ;
    T est un groupe retardateur susceptible d'être libéré ;
    R et R³ représentent individuellement l'hydrogène, un groupe alkyle ou aryle substitué ou non ;
    q est 0, 1 ou 2 ; et
    PUG est un groupe utile en photographie susceptible d'être libéré.
  5. Produit photographique tel que revendiqué dans la revendication 1, dans lequel le coupleur naphtolique est :
    Figure imgb0073
    Figure imgb0074
     ou
    Figure imgb0075
  6. Produit photographique tel que revendiqué dans la revendication 1, dans lequel le groupe ballasté se séparant au couplage comprend un groupe utile en photographie susceptible d'être libéré, c'est-à-dire un inhibiteur de développement, un développateur, un accélérateur de développement, un inhibiteur de blanchiment, un accélérateur de blanchiment, un colorant, un précurseur de colorant, un stabilisant, un coupleur, un nucléateur, un agent de fixage, un agent pour modifier le ton de l'image, un agent tannant, un agent antivoile, ou un agent absorbant le rayonnement ultraviolet susceptible d'être libéré, directement ou indirectement relié à la position de couplage du groupement coupleur naphtolique.
  7. Procédé de formation d'une image photographique dans un produit photographique exposé tel que défini dans l'une quelconque des revendications 1 à 6, ledit procédé consistant à développer le produit photographique exposé aux halogénures d'argent avec un développateur chromogène.
  8. Coupleur photographique naphtolique tel que défini dans l'une quelconque des revendications 1 à 6.
EP19910102367 1990-02-22 1991-02-19 Matériau photographique et procédé comprenant un coupleur naphtol enlevable par lavage Expired - Lifetime EP0443530B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48360190A 1990-02-22 1990-02-22
US483601 1990-02-22

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EP0443530A2 EP0443530A2 (fr) 1991-08-28
EP0443530A3 EP0443530A3 (en) 1992-02-05
EP0443530B1 true EP0443530B1 (fr) 1996-04-10

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ID=23920737

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910102367 Expired - Lifetime EP0443530B1 (fr) 1990-02-22 1991-02-19 Matériau photographique et procédé comprenant un coupleur naphtol enlevable par lavage

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EP (1) EP0443530B1 (fr)
JP (1) JPH04356042A (fr)
CA (1) CA2036041A1 (fr)
DE (1) DE69118569T2 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5234800A (en) * 1990-02-22 1993-08-10 Eastman Kodak Company Photographic material and process comprising wash-out naphtholic coupler
US5021322A (en) * 1990-02-22 1991-06-04 Eastman Kodak Company Photographic element comprising a development inhibitor releasing compound having a linking group between the carrier and the inhibitor
JPH05188540A (ja) * 1991-06-28 1993-07-30 Eastman Kodak Co 写真カプラーの製造方法
US5250399A (en) * 1991-06-28 1993-10-05 Eastman Kodak Company Photographic material and process comprising a universal coupler
US5250398A (en) * 1991-06-28 1993-10-05 Eastman Kodak Company Photographic silver halide material and process comprising water-solubilized naphtholic coupler
US5264582A (en) * 1991-07-01 1993-11-23 Eastman Kodak Company Method of forming a photographic coupler capable of forming a wash-out dye
US5630927A (en) * 1992-04-13 1997-05-20 Fuji Photo Film Co., Ltd. Silver halide color light-sensitive material
US5288593A (en) * 1992-06-24 1994-02-22 Eastman Kodak Company Photographic material and process comprising a coupler capable of forming a wash-out dye (Q/Q)
EP0576089A3 (fr) * 1992-06-24 1995-02-08 Eastman Kodak Co Produit photographique et procédé comprenant un coupleur capable de former en colorant éliminable par lavage.
EP0576087A1 (fr) * 1992-06-24 1993-12-29 Eastman Kodak Company Matériau photographique et procédé comprenant un copulant capable de former un colorant enlevable par lavage
US5279929A (en) * 1992-06-24 1994-01-18 Eastman Kodak Company Photographic material and process comprising a coupler capable of forming a wash-out dye (C/C)
US5318879A (en) * 1992-06-29 1994-06-07 Eastman Kodak Company Photographic element comprising a bleach accelerator releasing compound
DE69329172T2 (de) * 1992-06-29 2001-04-05 Eastman Kodak Co Photographisches Element enthaltend einen DIR-Kuppler und einen eine Säure löslichmachende Gruppe enthaltenden Bleich- beschleuniger freisetzenden Kuppler
EP0577191B1 (fr) * 1992-06-29 1997-05-21 Eastman Kodak Company Elément photographique et procédé comprenant un composé libérant un accélérateur de blanchiment et méthodes de préparation d'un tel composé
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
JPH0659410A (ja) * 1992-08-12 1994-03-04 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JPH08137065A (ja) * 1994-11-14 1996-05-31 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
US5932407A (en) * 1997-04-30 1999-08-03 Eastman Kodak Company Color photographic element containing oxidized developer-scavenging naphtholic coupler forming wash-out dye

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248962A (en) * 1977-12-23 1981-02-03 Eastman Kodak Company Photographic emulsions, elements and processes utilizing release compounds
JPS58162949A (ja) * 1982-03-20 1983-09-27 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
US4861701A (en) * 1987-10-05 1989-08-29 Eastman Kodak Company Photographic element and process comprising a compound which comprises two timing groups in sequence
DE3823049A1 (de) * 1988-07-07 1989-03-09 Agfa Gevaert Ag Farbfotografisches aufzeichnungsmaterial

Also Published As

Publication number Publication date
DE69118569D1 (de) 1996-05-15
CA2036041A1 (fr) 1991-08-23
EP0443530A2 (fr) 1991-08-28
DE69118569T2 (de) 1996-11-21
JPH04356042A (ja) 1992-12-09
EP0443530A3 (en) 1992-02-05

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