DE19601142A1 - Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths - Google Patents

Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths

Info

Publication number
DE19601142A1
DE19601142A1 DE1996101142 DE19601142A DE19601142A1 DE 19601142 A1 DE19601142 A1 DE 19601142A1 DE 1996101142 DE1996101142 DE 1996101142 DE 19601142 A DE19601142 A DE 19601142A DE 19601142 A1 DE19601142 A1 DE 19601142A1
Authority
DE
Germany
Prior art keywords
silver halide
characterized
developer
formula
color
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.)
Withdrawn
Application number
DE1996101142
Other languages
German (de)
Inventor
Peter Dr Bergthaller
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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
Priority to DE19525500 priority Critical
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Priority to DE1996101142 priority patent/DE19601142A1/en
Priority claimed from JP19696796A external-priority patent/JPH0934074A/en
Publication of DE19601142A1 publication Critical patent/DE19601142A1/en
Application status is Withdrawn legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20Quaternary compounds thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/66Nitrogen atoms
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/305Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30541Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407Development processes or agents therefor
    • G03C7/413Developers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/305Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers

Abstract

In a new process for generating a coloured picture from a dye coupler contg. silver halogenide material the development takes place in presence of a cpd. of formula (I), where R1, R2 and C form a system able to couple at the C-atom; NLG = 'non-leaving group' which cannot be hydrolytically cleaved; and DEV = developer rest. Also claimed is a silver halogenide colour photographic material contg. (I). Pref. cpd. (I) can either be present in the developer bath or in the silver halogenide material. The concn. of (I) in the silver halogenide emulsion layer is pref. 5-100 mmole/m2, esp. 10-50 mmole/m2. The colour photographic silver halogenide material comprises: (a) >= 1 dye coupler; (b) >= 1 silver halogenide emulsion layer, >= 1 of which contains a cpd. (I).

Description

Farbfotografische Bilder werden überwiegend durch bildmäßiges Belichten eines farbfotografischen Silberhalogenidmaterials, das Farbkuppler enthält, und chromo gene Entwicklung erzeugt. Color photographic images development contains predominantly by imagewise exposure of a color photographic silver halide material, color couplers and chromo gene produced.

Dazu wird das belichtete Material mit einem Bad in Kontakt gebracht, das eine Farbentwicklersubstanz enthält, deren Oxidationsprodukt mit den Farbkupplern zu Farbstoffen kuppelt, üblicherweise zu gelben, purpurnen und blaugrünen Farb stoffen. For this purpose, the exposed material is brought into contact with a bath containing a color developing agent whose oxidation product of coupling with the color couplers to dyes, to yellow usually materials magenta and cyan color. Die Farbentwicklersubstanzen sind überlicherweise N,N-disubstituierte p- Phenylendiamine. The color developing agents are customarily N, N-disubstituted p-phenylenediamines.

Es ist bereits vorgeschlagen worden, Farbentwicklersubstanzen in geschützter Form, z. It has already been suggested color developers in protected form, for example. B. in acylierter Form oder als Sulfamide dem farbfotografischen Material zuzusetzen, in einem Prozeß mit einem entwicklerfreien Bad freizusetzen und so, nach Oxidation an den belichteten Silberhalogenidkörnern, mit den Farbkupplern zur Reaktion zu bringen. B. add in acylated form or as sulfamides the color photographic material to release in a process with a developer free bath and so as to bring, after oxidation at the exposed silver halide grains to the reaction with the color couplers.

Die verkappten Entwickler kuppeln zu langsam und gestatten nicht die Herstellung von Bildern hoher Farbdichte. The blocked developer couple too slow and does not allow for the production of images of high color density.

Das Einlagern von Farbentwicklern in freier Form führt ebenfalls nicht zum Erfolg, da ein viel zu hoher Schleier erzeugt wird. The storing of color developers in free form also is not successful because a lot is produced at high veil.

Aufgabe der Erfindung war, ein System bereitzustellen, das mit einem farbent wicklerfreien Bad verarbeitet werden kann und dennoch zu ausreichend hohen Farbdichten und zu niedrigem Schleier führt. The object of the invention to provide a system that can be processed with a color t wicklerfreien bathroom and still results in sufficiently high color densities and low fog.

Es wurde nun gefunden, daß diese Aufgabe dadurch gelöst werden kann, wenn die Verarbeitung des belicheten Silberhalogenidmaterials in Gegenwart einer Verbin dung der Formel (I) durchgeführt wird: It has now been found that this object can be solved by, when the processing of silver halide belicheten dung in the presence of a Verbin of formula (I) is performed:

worin wherein
R₁ und R₂ zusammen mit dem C-Atom ein am C-Atom kupplungsfähiges System bilden, R₁ and R₂ form a clutch capable at the C-atom system together with the carbon atom,
NLG eine vom C-Atom während des Kupplungsprozesses hydrolytisch nicht abspaltbare Gruppe ("Non-leaving group") und NLG a hydrolytically non-removable from the C-atom during the coupling process group ( "non-leaving group") and
DEV einen Farbentwicklerrest ("Developer") bedeuten, der gegebenenfalls eine weitere Schutzgruppe enthalten kann. DEV represents a color developer remainder ( "Developer"), which may optionally contain a further protecting group.

Die Verbindung der Formel (I) kann im Entwicklerbad eingesetzt oder, vor zugsweise in das Silberhalogenidmaterial eingelagert werden, insbesondere in jede kupplerhaltige Silberhalogenidemulsionsschicht. The compound of formula (I) can be used in the developer or are stored before preferably in the silver halide material, in particular in any coupler-containing silver halide emulsion layer.

Die Verbindungen der Formel (I) können wasser- oder öllöslich sein. The compounds of formula (I) can be water- or oil-soluble. Im ersten Fall werden sie dem Material aus wäßriger Lösung, im zweiten Fall gelöst in einem hochsiedenden organischen Lösungsmittel zugesetzt. In the first case, they are added to the material from an aqueous solution dissolved in the second case in a high boiling organic solvent.

Die Herstellung der Verbindungen der Formel (I) erfolgt z. The preparation of the compounds of formula (I) z is carried out. B. durch Kupplung einer oxidierten Farbentwicklersubstanz mit einer Verbindung, die eine kupplungs fähige Methingruppe und an der Methingruppe einen Substituenten enthält, der nicht unter Ausbildung einer Azomethinverbindung abgespalten werden kann. B. which can be cleaved to form an azomethine compound by coupling an oxidized color developing agent with a compound that includes a clutch capable methine group and the methine group a substituent not.

Derartige Verbindungen werden auch als "Weißkuppler" bezeichnet. Such compounds are also called "white couplers". Bekannte Weißkuppler entstammen den Verbindungsklassen der Pyrazolone, Pyrrole, Isoxazolone und Imidazolone. Known white couplers are derived from the classes of compounds of pyrazolones, pyrroles, isoxazolones and imidazolones.

Bevorzugte Ausführungsformen der Verbindungen der Formel (I) sind in den Unteransprüchen angegeben. Preferred embodiments of the compounds of formula (I) are given in the subclaims.

Beispiele für geeignet Verbindungen sind die folgenden: Examples of suitable compounds are the following:

Herstellungs- und Anwendungsbeispiele maskierte Farbentwickler Manufacturing and application examples masked color developer Verbindung 35 compound 35

Man trägt unter Stickstoff in 200 ml Wasser 11,4 g (0,044 mol) 1-(4-Sulfophenyl)- 3,5-dimethylpyrazolon-5 und 12,4 g Farbentwickler CD-3 ein, gibt 26 g Kalium carbonat zu und trägt bei 25°C unter Rühren 12,2 g Diacetoxyjodbenzol ein. One carries under nitrogen in 200 ml of water, 11.4 g (0.044 mol) of 1- (4-sulfophenyl) - 3,5-dimethylpyrazolone-5 and 12.4 g of color developer CD-3, outputs 26 g of potassium carbonate and contributes to at 25 ° C with stirring, 12.2 g of a Diacetoxyjodbenzol. Die Temperatur steigt auf 35°C, das Gemisch färbt sich deutlich dunkler. The temperature rises to 35 ° C, the mixture turns significantly darker. Man rührt unter Stickstoff 4 Stunden nach und läßt zur Kristallisation drei Tage stehen. The mixture is stirred under nitrogen for 4 hours and allowed to crystallize are three days. Man saugt das schwach bräunliche Pulver ab, wäscht mit 50 ml 15 gew.-%iger Kalium acetatlösung und trocknet an der Luft. The slightly brownish powder is filtered off, washed with 50 ml of 15 wt .-% potassium acetate solution and dried in air.

Ausbeute: 8 g graues, in Wasser gut lösliches und aus Isopropanol umkristalli sierbares Pulver. Yield: 8 g of gray, well soluble in water and sierbares from isopropanol umkristalli powder.

Verbindung 2 compound 2

Man löst 20 g (0,1 mol) 1-Phenyl-3-ethyl-4-methylpyrazolon-5 in 100 ml Ethyl acetat, gibt 25 g Farbentwickler CD-4 (Hydrochlorid) zu, unterschichtet nach Durchblasen mit Stickstoff mit 400 ml 20 gew.-%iger Kaliumcarbonatlösung und trägt 35 g Diacetoxyjodbenzol ein. Dissolve 20 g (0.1 mol) of 1-phenyl-3-ethyl-4-methylpyrazolone-5 acetate in 100 ml ethyl, 25 g of color developer CD-4 (hydrochloride) to, underlaid by nitrogen sparging with 400 ml of 20 wt .-% potassium carbonate solution and carries a 35 g Diacetoxyjodbenzol. Nach 1 Stunde trennt man die Ethylacetatphase ab, trocknet mit wenig Magnesiumsulfat, dampft am Rotationsverdampfer ein. After 1 hour, the ethyl acetate phase is separated, dried with little magnesium sulfate, evaporated on a rotary evaporator. Der nach Verrühren mit wenig Acetonitril zurückbleibende Rückstand (30 g) wird ohne weitere Reinigung eingesetzt. The remaining after trituration with a little acetonitrile residue (30 g) is used without further purification.

Anwendungsbeispiel 1 Application Example 1 Einzelschicht 1 Single layer 1

Auf einen polyethylenkaschierten Papierträger wird eine fotografische Schicht gegossen, die folgende Bestandteile enthält: Onto a polyethylene laminated paper support is a photographic layer is cast, that includes the following components:

1,08 g Gelatine grünsensibilisierte Silberchloridemulsion mit 99,5% Chlorid und 0,5% Bromid, mittlere Korngröße 0,6 µm, entsprechend einem Auftrag von 0,45 g AgNO₃. 1.08 g of gelatin green-sensitized silver chloride emulsion containing 99.5% of chloride and 0.5% of bromide, average grain size 0.6 .mu.m, corresponding to a coverage of 0.45 g of AgNO₃.

Einzelschicht 2 Single layer 2

Zusammensetzung wie in 1), jedoch enthält die Schicht zusätzlich 0,6 g Verbin dung 35. Composition as in 1), but the coating contains in addition 0.6 g Verbin dung 35th

Beide Schichten werden durch Auftrag einer wäßrigen Schicht des Soforthärtungs mittels der Formel Both layers are formed by applying an aqueous layer of the Soforthärtungs by the formula

gehärtet. hardened.

Die Schichten werden unter einem Keil belichtet und dem üblichen Papierverarbeitungsprozeß unterworfen, jedoch mit folgenden Abweichungen: The layers are exposed through a wedge and subjected to the usual paper processing process, but with the following differences:
Prozeß 1: Typ RA 4 Process 1: Type RA 4
Prozeß 2: der Gehalt an Farbentwickler CD-3 wird auf ein Fünftel vermindert Process 2: the content of the color developer CD-3 is reduced to one-fifth
Prozeß 3: der Entwickler enthält anstelle des Farbentwicklers CD-3 1,3 g Phenidon/1000 ml Process 3: The developer includes, in place of the color developer CD-3, 1.3 g phenidone / 1000 ml

Beide Schichten werden in allen drei Prozeßvarianten verarbeitet und hinter einem Grünfilter vermessen: Both layers are processed in all three process variants and measured behind a green filter:

Man erkennt aus den Ergebnissen, daß die Einlagerung eines weißgekuppelten Pyrazolonderivates dazu führt, daß bei Verminderung des Anteils an Farbent wickler auf 20% des ursprünglichen Wertes die sensitometrischen Daten nur geringfügig verändert werden. It can be seen from the results that the incorporation of a weißgekuppelten Pyrazolonderivates causes the sensitometric data are changed only slightly at reducing the level of color t developers to 20% of the original value. Die Prozeßsicherheit eines derartigen Materials kann als stark verbessert angesehen werden. The process reliability of such material can be viewed as greatly improved.

Man erkennt weiterhin, daß mit einem derartigen Material, das den Farbentwickler in Form eines oxidativ aktivierbaren Pseudoleukoverbindung enthält, auch in einem farbentwicklerfreien Prozeß brauchbare Farbbilder erhalten werden können, wenn der Entwickler geeignete Elektronentransfer-agentien enthält. It will further be appreciated that with such a material containing the color developer in the form of an oxidatively activatable Pseudoleukoverbindung, even in a color developer free process useful color images can be obtained when the developer contains useful electron transfer agents. Ein derartiges Material ist somit grundsätzlich für ein Farbverstärkungsverfahren geeignet, wobei zur Verarbeitung lediglich Alkali und ein Verstärkungsmittel, z. Such a material is thus generally suitable for a color enhancement process, wherein for processing only alkali and a reinforcing agent, z. B. eine stabilisierte Wasserstoffperoxid-Additionsverbindung benötigt werden. B. a stabilized hydrogen peroxide addition compound are required. Der erforderliche Farb entwickler kann in wasserlöslich maskierter Form eingesetzt werden. The required color developer can be used in water-masked form.

Anwendungsbeispiel 2 Example 2

Es wird ein dreischichtiger Papierversuchsaufbau mit unten liegendem Gelbguß hergestellt, bei dem im It is made a three-layer paper test setup with bottom-brass, in which the
Vergleich A: die blauempfindliche Schicht wie üblich aufgebaut ist, Comparative A: the blue-sensitive layer is constructed as usual,
der erfindungsgemäße Aufbau B: 0,35 g Verbindung 2 enthält: the structure according to the invention B: 0.35 g of compound 2 contains:
der erfindungsgemäße Aufbau C: 0,35 g Verbindung 26 the assembly of the invention C: 0.35 g of compound 26
der erfindungsgemäße Aufbau D: 0,35 g Verbindung 35 the assembly of the invention D: 0.35 g of compound 35
der erfindungsgemäße Aufbau E: 0,3 g Verbindung 21. the structure E according to the invention: 0.3 g of compound 21st

Alle 5 Versuchsmaterialien werden in All five test materials are in
Prozeß 1 (Prozeß RA-4) mit einem typgemäßen Farbentwickler verarbeitet. Process 1 (process RA-4) are processed with a type proper color developer.

Prozeß 4: mit einem Farbentwickler verarbeitet, dessen pH-Wert durch Zugabe von Natriumdihydrogenphosphat um 0,4 pH-Einheiten vermindert ist. Process 4: processed with a color developer whose pH is reduced by adding sodium dihydrogen phosphate by 0.4 pH units. Man erhält folgende Ergebnisse: This gives the following results:

Das Beispiel zeigt, daß die besondere Empfindlichkeit der tiefstgelegenen Gelb schicht eines Colorpapieres gegen Verarbeitungsschwankungen, insbesondere gegen nicht ausreichende Regenerierung unter Abfall des pH-Wertes durch die Einlagerung von erfindungsgemäß maskierten und oxidativ aktivierbaren Farb entwicklervorläufern stark vermindert werden kann. The example shows that the particular sensitivity of the deepest yellow layer of a color paper to processing variations, in particular to insufficient regeneration under drop in pH by the incorporation of the present invention masked and oxidatively activatable color developer precursors can be greatly reduced.

Claims (11)

1. Verfahren zur Erzeugung eines farbigen Bildes aus einem farbkuppler haltigen Silberhalogenidmaterial durch chromogene Entwicklung, dadurch gekennzeichnet, daß die Entwicklung in Gegenwart einer Verbindung der Formel (I) durchgeführt wird: worin 1. A method for generating a color image from a color coupler-containing silver halide by chromogenic development, characterized in that the development in the presence of a compound of formula (I) is carried out: wherein
R₁ und R₂ zusammen mit dem C-Atom ein am C-Atom kupplungsfähiges System bilden, R₁ and R₂ form a clutch capable at the C-atom system together with the carbon atom,
NLG eine vom C-Atom während des Kupplungsprozesses hydrolytisch nicht abspaltbare Gruppe ("Non-leaving group") und NLG a hydrolytically non-removable from the C-atom during the coupling process group ( "non-leaving group") and
DEV einen Farbentwicklerrest ("Developer") bedeuten. DEV a color developer remainder ( "Developer") mean.
2. Verfahren nach Anspruch I, dadurch gekennzeichnet, daß die Verbindung der Formel (I) im Entwicklerbad ist. 2. The method of claim I, characterized in that the compound of formula (I) in the developer is.
3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die Verbindung der Formel (I) im Silberhalogenidmaterial ist. 3. The method according to claim 1, characterized in that the compound of formula (I) in the silver halide material.
4. Farbfotografisches Silberhalogenidmaterial mit wenigstens einer wenigstens einen Farbkuppler und wenigstens eine Silberhalogenidemulsion enthalten den Silberhalogenidemulsionsschicht, dadurch gekennzeichnet, daß die wenigstens eine Silberhalogenidemulsionsschicht eine Verbindung der Formel (I) enthält, worin R₁, R₂, NLG und DEV die in Anspruch 1 genannte Bedeutung besitzen. 4. Color photographic silver halide material having at least one at least one color coupler, and at least one silver halide emulsion containing the silver halide emulsion layer, characterized in that the at least one silver halide emulsion layer contains a compound of formula (I) wherein R₁, R₂, NLG and DEV have the meaning given in claim 1 ,
5. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 4, dadurch gekennzeichnet, daß R₁ und R₂ zu einem Ring geschlossen sind. 5. Color photographic silver halide material according to claim 4, characterized in that R₁ and R₂ are closed to form a ring.
6. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 3, dadurch gekennzeichnet, daß NLG mit DEV zu einem hydrolytisch spaltbaren Ring geschlossen ist. 6. A color photographic silver halide material according to claim 3, characterized in that NLG is closed with DEV to a hydrolytically cleavable ring.
7. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 4, dadurch gekennzeichnet, daß NLG mit R₁ und R₂ zu einem nicht hydrolytisch spaltbaren Ring geschlossen ist. 7. A color photographic silver halide material according to claim 4, characterized in that NLG is closed with R₁ and R₂ to a non-hydrolytically cleavable ring.
8. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 4, dadurch gekennzeichnet, daß DEV der Rest eines N,N-disubstituierten p-Phenylen diamins ist. 8. Color photographic silver halide material according to claim 4, characterized in that DEV is the residue of N, N-disubstituted p-phenylene diamine.
9. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 8, dadurch gekennzeichnet, daß DEV der Formel entspricht, worin 9. A color photographic silver halide material according to claim 8, characterized in that DEV is of the formula wherein
R₃ einen Alkylrest und R₃ an alkyl radical and
R₄ einen unsubstituierten oder substituierten Alkylrest bedeuten. R₄ is an unsubstituted or substituted alkyl group.
10. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 4, dadurch gekennzeichnet, daß die Verbindung der Formel (I) der Formel (II) entspricht, worin 10. A color photographic silver halide material according to claim 4, characterized in that the compound of formula (I) corresponds to formula (II) wherein
R₅ eine Alkyl- oder Acylaminogruppe und R₅ is an alkyl or acylamino group, and
R₆ eine Alkyl- oder Arylgruppe bedeuten, und R₆ represents an alkyl or aryl group, and
DEV die in Anspruch 4 genannte Bedeutung besitzt. DEV has the meaning given in Claim. 4
11. Farbfotografisches Silberhalogenidmaterial nach Patentanspruch 4, dadurch gekennzeichnet, daß die Verbindung der Formel (I) in der wenigstens einen Silberhalogenidemulsionsschicht in einer Menge von 5 bis 100 mMol/m², vorzugsweise 10 bis 50 mMol/m² eingesetzt wird. 11. A color photographic silver halide material according to claim 4, characterized in that the compound of formula (I) is used a silver halide emulsion layer in an amount of 5 to 100 mmol / m², preferably 10 to 50 mmol / m at least in the.
DE1996101142 1995-07-13 1996-01-15 Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths Withdrawn DE19601142A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19525500 1995-07-13
DE1996101142 DE19601142A1 (en) 1995-07-13 1996-01-15 Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996101142 DE19601142A1 (en) 1995-07-13 1996-01-15 Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths
JP19696796A JPH0934074A (en) 1995-07-13 1996-07-09 Color image forming method

Publications (1)

Publication Number Publication Date
DE19601142A1 true DE19601142A1 (en) 1997-01-16

Family

ID=7766707

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1996101142 Withdrawn DE19601142A1 (en) 1995-07-13 1996-01-15 Colour photographic process and material using masked developer - combining high colour densities with decreased fogging and sensitivity to process variations, also allowing use of developer free baths

Country Status (1)

Country Link
DE (1) DE19601142A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1246006A3 (en) * 2001-03-29 2004-08-11 Fuji Photo Film Co., Ltd. Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
US7125988B2 (en) 2002-09-27 2006-10-24 Fuji Photo Film Co., Ltd. Dye-forming coupler and silver halide color photographic light-sensitive material
US7193080B2 (en) 2001-03-30 2007-03-20 Fuji Photo Film, Co., Ltd. Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
US7196194B2 (en) 2001-03-29 2007-03-27 Fuji Photo Film Co., Ltd Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
US7495103B2 (en) 2004-06-24 2009-02-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8354427B2 (en) 2004-06-24 2013-01-15 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8410274B2 (en) 2005-12-28 2013-04-02 Vertex Pharmaceuticals Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US8802700B2 (en) 2010-12-10 2014-08-12 Vertex Pharmaceuticals Incorporated Modulators of ATP-Binding Cassette transporters
US9701639B2 (en) 2014-10-07 2017-07-11 Vertex Pharmaceuticals Incorporated Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
US9751839B2 (en) 2009-03-20 2017-09-05 Vertex Pharmaceuticals Incorporated Process for making modulators of cystic fibrosis transmembrane conductance regulator
US10272046B2 (en) 2012-02-27 2019-04-30 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196194B2 (en) 2001-03-29 2007-03-27 Fuji Photo Film Co., Ltd Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
EP1246006A3 (en) * 2001-03-29 2004-08-11 Fuji Photo Film Co., Ltd. Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
US7193080B2 (en) 2001-03-30 2007-03-20 Fuji Photo Film, Co., Ltd. Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound
US7125988B2 (en) 2002-09-27 2006-10-24 Fuji Photo Film Co., Ltd. Dye-forming coupler and silver halide color photographic light-sensitive material
US8829204B2 (en) 2004-06-24 2014-09-09 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US7495103B2 (en) 2004-06-24 2009-02-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8324242B2 (en) 2004-06-24 2012-12-04 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8354427B2 (en) 2004-06-24 2013-01-15 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US9090619B2 (en) 2004-06-24 2015-07-28 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8614327B2 (en) 2004-06-24 2013-12-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8629162B2 (en) 2004-06-24 2014-01-14 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8101767B2 (en) 2004-06-24 2012-01-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8741925B2 (en) 2004-06-24 2014-06-03 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8754224B2 (en) 2005-12-28 2014-06-17 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US8410274B2 (en) 2005-12-28 2013-04-02 Vertex Pharmaceuticals Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9139530B2 (en) 2005-12-28 2015-09-22 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9670163B2 (en) 2005-12-28 2017-06-06 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9931334B2 (en) 2005-12-28 2018-04-03 Vertex Pharmaceuticals Incorporated Solid forms of N[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9751839B2 (en) 2009-03-20 2017-09-05 Vertex Pharmaceuticals Incorporated Process for making modulators of cystic fibrosis transmembrane conductance regulator
US8802700B2 (en) 2010-12-10 2014-08-12 Vertex Pharmaceuticals Incorporated Modulators of ATP-Binding Cassette transporters
US10272046B2 (en) 2012-02-27 2019-04-30 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US9701639B2 (en) 2014-10-07 2017-07-11 Vertex Pharmaceuticals Incorporated Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator

Similar Documents

Publication Publication Date Title
DE4142956C2 (en) Bleachable antihalation system for photographic materials
US4421845A (en) Silver halide photographic light-sensitive material
US3615506A (en) Silver halide emulsions containing 3-cyclicamino-5-pyrazolone color couplers
DE2823414C2 (en)
US4060418A (en) Phenoxy carbonyl derivatives of a paraphenylenediamine color developer and their use in an image-receiving sheet for color diffusion transfer
EP0242685B1 (en) Oxidative release of photographically useful groups from hydrazide compounds
EP0173540A2 (en) Color image forming method
DE2855697C2 (en)
DE2703145C2 (en)
EP0318579B1 (en) Stabilizing bath for use in photographic processing
EP0080896B2 (en) Method for the formation of dye image
US2860974A (en) Photographic color correction process
US4232112A (en) Process for treating silver halide color photographic photosensitive material
DE3020416C2 (en)
JP3136010B2 (en) Method of forming a color photographic material and a photographic color image
US4959299A (en) Silver halide color photographic materials
DE3008321C2 (en)
GB656131A (en) Improvements in and relating to processes and material for the manufacture of colourphotographic images
US2756142A (en) Photographic color reproduction process
US4629683A (en) Processing silver halide photographic material with blocked agent and hydroxylamine
DE60020283T2 (en) Cyan coupler solvent and stabilizer-containing photographic element and process
US3958993A (en) Development inhibitor-releasing type compound for photographic use
US2284877A (en) Light sensitive color element
US4348475A (en) Process for the production of photographic images
US5273865A (en) Photographic color developing composition and method for processing a silver halide color photographic element

Legal Events

Date Code Title Description
8130 Withdrawal