US3782948A - Photographic material containing nitro compounds for the silver dyestuff bleaching process - Google Patents

Photographic material containing nitro compounds for the silver dyestuff bleaching process Download PDF

Info

Publication number
US3782948A
US3782948A US00217654A US3782948DA US3782948A US 3782948 A US3782948 A US 3782948A US 00217654 A US00217654 A US 00217654A US 3782948D A US3782948D A US 3782948DA US 3782948 A US3782948 A US 3782948A
Authority
US
United States
Prior art keywords
formula
water
residue
nitro compounds
dye
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00217654A
Other languages
English (en)
Inventor
H Schaller
A Froehlich
A Oetiker
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.)
Ilford Imaging Switzerland GmbH
Original Assignee
Ciba Geigy 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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of US3782948A publication Critical patent/US3782948A/en
Assigned to CIBA-GEIGY AG reassignment CIBA-GEIGY AG ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: H.A. WHITTEN & CO.
Assigned to ILFORD AG, A CO. OF SWITZERLAND reassignment ILFORD AG, A CO. OF SWITZERLAND ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CIBA-GEIGY AG
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic 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
    • C07D231/14—Heterocyclic 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/24—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule
    • 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
    • G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Definitions

  • the present invention provides a photographic material for the s'iIver-dyestuff bleaching process said material consisting of different layers and containing in at least one silver halide layer an azo dye that can be bleached by silver which material contains in at least one of said layers a colorless or faintly colored nitro compound of the formula in which A represents an aromatic or heterocyclic residue consisting of one or two rings each containing 5 or 6 ring members; B represents an organic residue containing at least 8 members; D and E each represents an acid water-solubilizing group; m, n and p each represents 1, 2 or 3, and q and r each represents an integer of at least one.
  • the residue B is, for example, an at least 8-membered carbon chain which may contain hetero atoms.
  • a D E m 11 p q and r have the above meanings and B represents a residue which contains at least one aliphatic chain consisting of carbon atoms and, if desired, oxygen and/or nitrogen atoms, of at least twelve members in all, which residue is linked with the residue A directly or through an NR-CO-, ---CONR---, O- or NR-- bridge, where R represents a hydrogen atom or a lower alkyl group.
  • nitro compounds of the formula ilp-a ( ⁇ NOm (a ea -n+1 (m -1) (r-ll +1 in which A2, B4, D1, E1, "'11, n p q] and r1 have the above meanings, are preferably used.
  • nitro compounds of the Formula 7 those are especially valuable which correspond to the formula NH-C o-o O2N D1 in which G represents a residue of the formula xHZxft or C H COO'H (where x is a digit of from 11 to 17 and y a digit of from 14 to 20) and D represents a sulphonic or carboxylic acid group.
  • the compounds of the Formulae 1 to 8 can be readily manufactured by known methods, for example by reacting an acid chloride, for instance stearoyl chloride, lauroyl chloride, sebacinoyl chloride, abiethinoyl chlo ride, or an acid anhydride for instance dodecenyl'suo cinic anhydride, with the corresponding aminonitro compounds, or by reacting aromatic nitro compounds containing a replaceable halogen atom, for example 4-nitrochlorobenzene-Z-sulphonic acid, with a difiusioninhibiting amine or enol, for example 1,12-diaminm dodecane, N-methyloctadecylamine, pentaor tetra-ethyleneglycol or polyethylene-imine, or by reacting aromatic nitro-isocyanates, for example 3-nitro-phenylisocyanate or 3nitrophenyl-sulphonylisocyanate, with a dilfusion
  • the residue A in the Formula 1 preferably represents an aromatic residue consisting of one or two rings, for example a benzene or naphthalene residue or a heterocyclic residue consisting of one or two rings, for example a pyridine or quinoline ring; or A may also represent an aromatic-heterocyclic system, for example a phenylpyrazolone residue.
  • the residue A contains one or two nitro groups and may also be substituted by one or two acid water-solubilizing groups, for example sulphonic or carboxylic acid groups.
  • the residue A may be linked with the residue B either directly or through a bridge member.
  • B as diffusion-inhibiting group may be bound to group A directly or through a bridge member, e.g. S,
  • R is hydrogen or an alkyl group having at most 5 carbon atoms.
  • diffusion-inhibiting groups B are suitable, for instance, linear or branched, saturated or unsaturated substituted or unsubstituted hydrocarbon radicals which when substituted contain (a) nitrogen, oxygen or nitrogen and oxygen atoms, as substituents or chain members, (b) carbocyclic nuclei and (c) carbocyclic nuclei and nitrogen, oxygen or nitrogen and oxygen as substituents or chain members, said diffusion-inhibiting group containing at least 8 members.
  • the actual difiusion-inhibiting residue within the residue B may also be linked with an aromatic or heterocyclic ring, for example with a. benzene ring. This ring may, if desired, contain several such diifusion-inhibiting residues, in which case the residue B is advantageously linked with A by a bond starting from the ring.
  • Diffusion-inhibiting residues which represent the residue B itself or only a part thereof are, for example, alkyl, e.g. dodecyl, alkylamino, e.g. dodecylamino, alkanoyl, e.g.
  • the acid water-solubilizing groups D and E are linked with A or B; it is possible that both A and B, or only A, or only B or neither A nor B contain such groups.
  • D and E preferably represent sulphonic or canboxylic acid groups.
  • An acid group linked with B is formed, for example, by using an alkylene-substituted succinic anhydride or a sulphonatable unsaturated aliphatic compound, for example oleic acid, as acylating agent for A.
  • the introduction of acid water-solubilizing groups into the molecule of the nitro compound may be dispensed with without sacrificing the solubility in water.
  • the compounds of the Formula 1 may also be insoluble in water; such nitro compounds may also be soluble in a sparingly volatile organic solvent, for example in tricresyl phosphate or dibutyl phthalate.
  • the atomic grouping of the formula ( ⁇ Nom t in which A, D, n, p and r have the above meanings may appear in the molecule once or twice, depending on the number of the bond-forming groups in B.
  • tetraor pentaethylene glycol combine through their hydroxyl groups with two residues of the Formula 9, as do diamines, for example diaminodecane, or dicarboxylic acids, for example sebacic acid, while polyvalent residues B, for example polyvinyl alcohol, maleic anhydride copolymers or carbohydrates are capable of combining with several residues of the Formula 9; in. the case of the maleic anhydride copolymers the number of the liberated canboxyl groups in the ester or amide-like compound comprising the residue of the Formula 9 depends on the polymer and on the degree of conversion reached.
  • the residue of the Formula 9 may also be linked with the diffusion-inhibiting residue through so-called reactive compounds, for example cyanuric chloride, dichloropyrimidine, B-chloropropionyl chloride, dichloroquinoxaline carboxylic acid chloride or the like.
  • reactive compounds for example cyanuric chloride, dichloropyrimidine, B-chloropropionyl chloride, dichloroquinoxaline carboxylic acid chloride or the like.
  • watersoluble polymers miscible with gelatin are suitable above all, or under certain conditions even gelatin itself.
  • nitro compounds of Formula 1 are the following compounds of the Formulae I to XXXI:
  • 02N- NEG-CO-CnHu can OzN- NIH-C OCHgC HC 15H OaH (III) -NH-C O-CHz-C HC12H28 O OH zN (IV) 10 on p p o aNO-NH-C Q-CH2 0 131-0 n coon v NH-CO-CHz-CH-OrzE: 3 0 OH V om NHCO--CHz-CH-Cr2Hz;
  • polymers may also be mentioned, for example the reaction product of polyvinyl alcohol with 3-nitrophenylisocyanate or the reaction product of a vinyl alcohol/maleic anhydride copolymer with 1-amino-3-nitrobenzene.
  • the nitro compounds of the Formula 1 are substantially colorless and as a rue soluble as such or in the form of their alkali metal salts in water or in a mixture of water and an organic solvent, preferably methanol. When introduced into gelatine, they dry together with it and are then glass clear, even when they are dispersed in the gelatine. Water-insoluble nitro compounds may be dissolved in a sparingly volatile organic solvent and then finely dispersed in the gelatine.
  • the nitro compounds of Formula 1 may be added to all the layers or only to some of the emulsion, dye, emulsion dye, intermediate or auxiliary layers according to the desired effect.
  • the nitro compounds may be introduced into the disperse phase and/or the binder layer which serves as a matrix.
  • the term intermediate layers comprises especially the separating layers, while the auxiliary layers are lubricating layers, protective layers, filter layers, antihalation layers, or coatings, substrations and baryta layers.
  • the application of a bleaching catalyst improves the quality of the image.
  • the bleaching catalysts used in a bleaching process with metallic silver are reduced to hydro compounds which then undergo reoxidation and cause the bleaching of the dye.
  • the reduced form provided it does not act immediately in the bleaching process, migrates into the adjacent layers where it produces an undesired and harmful bleaching of the image dye.
  • the nitro compounds in the intermediate layers prevent this harmful effect by oxidizing the reduced catalyst migrating from the layer.
  • these nitro compounds can be added in different concentrations to the individual layers of a multi-layer material, especially to those which contain the image dye, with a view to influencing the sensitometric properties of the image-forming layers individually and thereby improving the physical properties of the image in the multi-layers.
  • a quinone a nitroso compound or an azo dye
  • a 0.02-molar aqueous quinone solution has at 420 nm. an absorption maximum of 0.76 density, whereas the compound of the Formula I, that is 2-stear0ylamino-6-nitrotoluene-4-sulphonic acid, in the same concentration shows no absorption in the visible region.
  • the compound of the Formula I that is 2-stear0ylamino-6-nitrotoluene-4-sulphonic acid
  • these nitro compounds are stable and are not affected by the action of light.
  • the initially pale yellow solution of quinone in gelatine prepared by adding 20 ml. of a methanolic 0.1-molar solution to ml.
  • the diflusion-resistant and soluble nitro compounds are easy and cheap to manufacture.
  • nitro compounds of the Formula 1 offer special advantages when used as additives to separating, filter or antihalation layers that contain colloidal silver or a fogged silver halide emulsion. 1
  • the nitro compounds of the Formula'l When the nitro compounds of the Formula'l are added to dyed layers, the nitro compounds compete with the dye during the bleaching process, whereby in general a flatter gradation in the dyed layer is produced.
  • the product is taken off the suction filter without drying, dissolved in 150 ml. of glacial acetic acid, mixed with 30 g. of carbon, heated to theboil and suction filtered hot.
  • the filtrate is mixed with 1000 ml. of water at the boil and then cooled to C.; the'precipitated crystals are suction filteredand'washedwith 1000 ml. of water.
  • Another recrystallizationfrom 1000 ml. of ethanol yields 200 g. of colorless crystals of 4-methyl-octadecylamino-3-aminobenzene sulphonieacidmelting at 181 C. 25 g.
  • Example 1 Two glass plates A and B, each measuring 13 x 18 cm., are coated with a dye gelatine solution of the following composition: 3.3 ml. of 6% gelatine solution, 2.0 ml. of 1,3-dichlorotriazine 5 aminobenzene-4-sulphonic acid (1% solution), 0.5 ml. of a 1% solution of the dye of the formula @011 S OaH 4.2 ml. of water.
  • Plate A is coated with a solution of 5.0 ml. of 10% gelatin, 1.0 ml. of 1% colloidal silver solution, 5.0 ml. of water and 2.0 ml. of 1,3-dichlorotriazine-S-aminobenzene-4'-sulphonic acid (1% solution) and plate B with a solution at 5.0 ml. of 10% gelatin, 1.0 ml. of colloidal silver solution (1% 5 .0 m1. of water, 0.125 g. of Z-nitro- 6-stearoylaminotoluene-4-sulphonic acid, 2.0 m1. of 1,3- dichlorotriazine-S-aminobenzene-4'-sulphonic acid (1% Each plate A and B is halved so that 4 plates, A A B and B are obtained.
  • the plates A and B are subjected to the usual dye bleaching process as follows:
  • a dye bleaching bath composed of: ml. of 37% hydrochloric acid, g. of potassium bromide, 8 g. of thiourea, 1 ml. of 2,5-dimethylpyrazine, made up with water to 1 litre, then rinsed in water for 2 minutes, fixed in a solution of 150 g. of sodium thiosulphate, 15 g. of sodium sulphite, 13.5 ml. of 100% acetic acid, 15 g. of sodium metaborate and 15 g. of potassium aluminium sulphate, made up with water to 1 litre, and then rinsed in water for 10 minutes.
  • a dye bleaching bath composed of: ml. of 37% hydrochloric acid, g. of potassium bromide, 8 g. of thiourea, 1 ml. of 2,5-dimethylpyrazine, made up with water to 1 litre, then rinsed in water for 2 minutes, fixed in a solution of 150 g. of sodium
  • Example 2 As described in Example 1 a 7% gelatin solution is mixed at 40 C. with a solution of a cyan image dye of the formula QC O-HN-Q and the usual casting additives for example a wetting agent, hardener and glycerine. By adding the requisite quantity of water the viscosity is then adjusted to the desired value. A layer 5n thick (in the dry state) is then produced on a photographic layer base at a casting temperature of 40 C. and a casting rate of 6 meters per minute.
  • a cyan image dye of the formula QC O-HN-Q the usual casting additives for example a wetting agent, hardener and glycerine.
  • gelatine interlay 2n a gelatine interlay 2,14 thick; in addition to the wetting agent and the hardener this layer contains no further additives.
  • gelatine interlay 2n a gelatine interlay 2n thick, which contains the same additives and also in addition 16.7% (referred to gelatine) of the compound of the Formula I.
  • Both interlays are then covered in the known manner with a silver halide emulsion to produce a layer 5 thick in the dry state.
  • the emulsion contains 7% of gelatine and 34 g. of silver per kg.
  • Both materials are exposed to incandescent light under a grey step wedge, developed in a bath containing l-methylamine-4-hydroxybenzene sulphate and hydroquinone to the same silver density and freed from silver halide in a bath containing sodium thiosulphate. After an intermediate rinsing in Water, the materials are treated for 8 minutes at 20 C. in a dye bleaching bath of the following composition:
  • Example 3 12' 12 ml. of methanol containing 1.25 g. of Compound XXIX, and 1 ml. of hardener solution (plate A).
  • each plate After drying, each plate is covered with a mixture of 1.65 ml. of 6% gelatine, 1 ml. of hardener and 0.29 ml. of a 1% aqueous solution of the dye of the formula son: on,
  • strip B reveals a yellow dye wedge, whereas strip A is of a uniform yellow color.
  • strip A reveals the relative value of 1.6 and strip B of 0.26, that is to say the reduced form of the catalyst diffusing from the" silver halide emulsion reaches the dye layer in strip B and produces a bleaching of the dye, whereas in strip A the compound of the'Formula XXIX which is present causes the reoxidation of the reducedcatalystwsozthat it: cannot react at all or only slightly in the dyed-layer.
  • any desired degree of gradation 'ofthe plates A and B can be achieved by a suitable choice of the concentration of Compound XXIX.
  • This method may also be used to obtain the optimum individual gradations in a multipack material, especially by using the appropriate quantity of Compound X'XIX in each individual layer.
  • Example 4 Atranspareti t cellulose'triacetate base is coated successively with the following layers: 1) Gelatinela'ye'r containing the dye of the formula Layer 1.5,u thick.s.-;Dye concentration: 0.11 g./m. (2) Silver bromide gelatin emulsion, red-sensitive. Layer 1.5g. thick. Concentrations 0.55 g. of silver/m (3) Interlay, containing the compound of the Formula XXX. Layer 1.5,u thick. Concentration: 0.44 g. of the compound of the Formula )OCX per m (4) Gelatine layer containing the dye of the formula SOaNa Layer 1.5,u thick. Concentration 0.15 g. of dye/m9.
  • the same multi-layer material is prepared but without Compound XXX in layer 3.
  • the two materials are exposed behind a step wedge and processed for (a) 10 minutes in the developer G p-Methylarninophenol sulphate 1 Sodium sulphite, anhydrous 20 Hydroquinone 4 Sodium carbonate, anhydrous 10 Potassium bromide 2 Made up with water to 1 litre.
  • B is a diffusion-inhibiting group bound to group A directly or through a -NR-CO
  • R is hydrogen or an alkyl group having at most 5 carbon atoms
  • B comprising a linear or branched, saturated or unsaturated
  • substituted or unsubstituted hydrocarbon radical which when substituted contains (a) nitrogen, oxygen or nitrogen and oxygen atoms,
  • diifusion-inhibiting group B contains from 8 to 25 carbon atoms and is selected from alkyl, alkylamino, alkanoyl, phenylcarbamoylalkylenecarbonyl, alkylphenoxymethylene, alkanoylaminophenylcarbamoylanilide, alkanoylphenylcarbamoyl, phenoxypolyethyleneoxyalkylene, alkylpyrazolone, N-alkylatedaminophenyl, aliphatic carbocyclic having up to 19 carbon atoms, benzamidodiphenylamino optionally substituted in the diphenyl moiety by lower alkoxy, phenylcarbamoyloxy-polyethylenoxycarbonyl and anilinoalkylene, D and E each is an acid group which confers water solubility, m, n, p and r each is 1 or 3.
  • D and E each is an acid group which confers water so
  • a photographic material according to claim 3 in which A is a benzene ring, D and E each is a sulfonic acid group or a carboxylic acid group, B is an alkyl radical having from 8 to 18 carbon atoms linked to group A through the NHCO bridge or a sulfonated benzene radical substituted by an alkylamino group wherein the alkyl moiety contains from 8 to 18 carbon atoms, said benzene radical being linked to group A through the CONH- bridge, m is 1, n, p, q and r each is 1 or 2.
  • a photographic material as claimed in claim 1 containing a nitro compound of the formula ('lJHa NH-CO-G OZN in which G represents a residue of the formula OxHZXil r C I-I COOH, in which x is a digit of from 11 to 17 and y is a digit of from 14 to 20, and D represents a sulfonic or carboxylic acid group.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
US00217654A 1968-04-09 1972-01-13 Photographic material containing nitro compounds for the silver dyestuff bleaching process Expired - Lifetime US3782948A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH523668A CH507536A (de) 1968-04-09 1968-04-09 Photographisches, Nitroverbindungen enthaltendes Material für das Silberfarbbleichverfahren

Publications (1)

Publication Number Publication Date
US3782948A true US3782948A (en) 1974-01-01

Family

ID=4290213

Family Applications (1)

Application Number Title Priority Date Filing Date
US00217654A Expired - Lifetime US3782948A (en) 1968-04-09 1972-01-13 Photographic material containing nitro compounds for the silver dyestuff bleaching process

Country Status (6)

Country Link
US (1) US3782948A (de)
BE (1) BE731162A (de)
CH (1) CH507536A (de)
DE (1) DE1917813A1 (de)
FR (1) FR2005820A1 (de)
GB (1) GB1245345A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957516A (en) * 1973-05-17 1976-05-18 Ciba-Geigy Ag Preparation for the processing of photographic materials
US4576885A (en) * 1983-01-26 1986-03-18 Ciba-Geigy Ag Photographic material for the silver dye bleach process
US4988805A (en) * 1987-07-29 1991-01-29 Bayer Aktiengesellschaft Naphtholazophenylazoaminonaphthol compounds and copper complexes thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1296109B (de) * 1966-09-13 1969-05-29 Gewerk Eisenhuette Westfalia Foerdermittelrueckvorrichtung mit am Ausbaugespann angeordnetem Rueckzylinder
JPS5938943B2 (ja) * 1977-06-21 1984-09-20 富士写真フイルム株式会社 ２−アルコキシアルコキシ−５−ニトロベンゼンスルホン酸およびその塩

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957516A (en) * 1973-05-17 1976-05-18 Ciba-Geigy Ag Preparation for the processing of photographic materials
US4576885A (en) * 1983-01-26 1986-03-18 Ciba-Geigy Ag Photographic material for the silver dye bleach process
US4988805A (en) * 1987-07-29 1991-01-29 Bayer Aktiengesellschaft Naphtholazophenylazoaminonaphthol compounds and copper complexes thereof

Also Published As

Publication number Publication date
CH507536A (de) 1971-05-15
FR2005820A1 (de) 1969-12-19
BE731162A (de) 1969-10-08
GB1245345A (en) 1971-09-08
DE1917813A1 (de) 1969-10-30

Similar Documents

Publication Publication Date Title
US3843371A (en) Photographic material stabilised against the deleterious effects of ultraviolet radiation
US2274782A (en) Light-sensitive photographic material
US3260597A (en) Photographic multicolor diffusion transfer process using dye developers and development arrestors
US2342546A (en) Production and use of dyestuffs
US3211554A (en) Photographic layers for the silver dyestuff bleaching method
US3471293A (en) Antihalation and filter dyes for photographic materials
US3255001A (en) Photographic products, processes and compositions utilizing insulated azo dye developers
US2899305A (en) Colour photography
US2976146A (en) Novel cyan-forming couplers
US3963492A (en) Method for processing silver dye bleach materials
US4237281A (en) Dyestuffs containing amino or imino groups
US2768894A (en) Photographic element with emulsion layer containing color former and wetting agent
US3796576A (en) Photographic material comprising a quinoxaline as dye bleaching catalyst
US3684729A (en) Brightener compositions
US2979405A (en) Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
US4443537A (en) Hydroquinone derivatives and their use in photographic materials
US3615494A (en) Method of producing color photographic images by the silver dye bleach method
US3135604A (en) Photographic processes, compositions, and products utilizing azo dye developers
US3094418A (en) Silver halide meulsions containing cationic oxonol and benzylidene dyes
US3038802A (en) Photographic color element with novel cyan dye
US2395776A (en) Color photography
US2328652A (en) Process of color photography and composition thereof
US2078398A (en) Photographic material having aldehyde screening dyes
US2688538A (en) Photographic elements and process of color correction utilizing styryl dyes as couplers
US3684513A (en) Color photographic silver dye bleach material containing azo dyes with acyl blocked auxochromic groups

Legal Events

Date Code Title Description
AS Assignment

Owner name: CIBA-GEIGY AG, SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:H.A. WHITTEN & CO.;REEL/FRAME:005184/0184

Effective date: 19890719

AS Assignment

Owner name: ILFORD AG, A CO. OF SWITZERLAND, SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:CIBA-GEIGY AG;REEL/FRAME:005319/0226

Effective date: 19900502