US3767402A - Photographic colour material - Google Patents

Photographic colour material Download PDF

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Publication number
US3767402A
US3767402A US00176689A US3767402DA US3767402A US 3767402 A US3767402 A US 3767402A US 00176689 A US00176689 A US 00176689A US 3767402D A US3767402D A US 3767402DA US 3767402 A US3767402 A US 3767402A
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Prior art keywords
formula
quinoxaline
colour
minutes
percent
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US00176689A
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English (en)
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H Schlunke
C Egli
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Ilford Imaging Switzerland GmbH
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Ciba Geigy AG
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Assigned to ILFORD AG, A CO. OF SWITZERLAND reassignment ILFORD AG, A CO. OF SWITZERLAND ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CIBA-GEIGY AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • 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

Definitions

  • ABSTRACT A photographic light-sensitive material for the silver bleaching process which comprises on a support in at least one layer a quinoxaline of formula O ⁇ N Ar gN Az v 11 Claims, N0 Drawings PHOTOGRAPHIC COLOUR MATERIAL This invention relates to photographic material which contains quinoxalines as colour bleaching catalysts.
  • a photographic eight-sensitive material for the silver bleaching process which comprises on a support in at least one layer a quinoxaline of formula or 6,7-position, as colour bleaching catalysts.
  • Advantageously quinoxalines of formula are used, wherein A and A each represent an alkyl group with at most 5 carbon atoms or an optionally substituted benzene group and n represents 1 or 2, whereby the rings are interconnected in the indicated manner.
  • Groups A, and A or A and A., as well as groups A; and A of the following formula (3) can be the same or different.
  • Alkyl groups with 1 m5, preferably 1 to-3 carbon atoms which can be used are e.g. amyl, n-sec. or tert. butyl, n or isopropyl, ethyl or in particular methyl groups.
  • bicyclic aralkyl groups are mentioned e.g. the naphthenyl or benzyl group.
  • the at most bicyclic aryl groups are naphthalene, diphenyl or benzene groups, having optionally further substituents such as, e.g., lower alkyl, lower alkoxy, hydroxy, substituted amines, amine or halogen. Particularly lower alkyl groups can be used as substituents for the amine.
  • Heterocyclic 5 or 6-membered groups which can be used are, e.g., pyridyl, furyl or thienyl groups.
  • the compounds of formula (1) are dioxolo or dioxano quinoxalines.
  • A is a methyl or phenyl group and n is l or 2, whereby the rings are interconnected in the indicated manner, are particularly suitable.
  • the quinoxalines of formula (1) can be used as colour bleaching catalysts in a processing bath, preferably in a colour bleaching bath and/or in a layer of the photographic material.
  • the reduction products of the quinoxalines of formula (1) can also be used for so-called bleach development, by themselves acting as hydrogen developers in an acid medium.
  • the quinoxalines of formula (I) can be used either alone or in the presence of other conventional colour bleaching catalysts. It is also possible to use various quinoxalines of formula (1) simultaneously in the colour bleaching bath. Finally the quinoxalines of formula (1 can also be used together with other bleachingpromoting measures, e.g., together with an irradiation or bubbling with a gas of the colour bleaching bath or in additon of organic solvents to the colour bleaching bath. 7 w
  • the quinoxalines of formula (1 can therefore be incorporated into a coating free from bleachable image dye.
  • the multi-layer material can therefore have for example an additional gelatin layer containing only the catalyst located directly on the emulsion carrier or between two colour layers. In the latter case the catalystcontaining layer also acts as a separating layer.
  • the catalyst can also be incorporated into colloidal silver or layers containing filter or antihalo dye or covering coatings. These filter layers as well as the coatings with the image dyes advantageously contain gelatin as the layers colloid.
  • the quinoxalines of formula l can also be incorporated directly into a layer containing image dye.
  • the mjlti-layer material can have the conventional composition. Colour-photographic images can be produced in per se known manner with the photographic materials of tje indicated composition.
  • the colour bleaching catalysts of formula (I) can, as already indicated, e. g. be added to the colour bleaching bath where they then directly exert their action. They can also be added to a previous treatment bath, e.g., the developer, a hardening bath, a stop bath or a special bath preceeding the silver bleaching bath. In this way a certain portion of the catalyst quantity introduced is absorbed and retained by the photographic coating material until it can act in the colour bleaching bath. Depending on the particular use the quantity of catalyst used can vary within wide limits. Generally it suffices for a strong action to add 0.001 to 0.
  • a silve complex constituent such as, e.g., alkali metal bromide or iodide or thiourea and optionally an anti-oxidising agent such as e.'g. sodium hypophosphite and for giving the necessary pH-value a stong organic or inorganic acid such as, e.g., benzenesulphonic acid, hydrochloric acid, sulphuric acid, phosphoric acid or sodium bisulphate.
  • a photographic, light-sensitive material for the silver dyebleach process containing on a carrier in at least one layer as a colour bleaching catalyst a quinoxaline of formula 1 and photographic processing baths, particularly colour bleaching baths, characterised in that as the colour bleaching catalyst they contain at least a quinoxaline of formula (1).
  • a further object of the invention is a process for pro ducing colour photographic images according to the silver dye-bleach process on materials containing on a substrate at least one silve halide emulsion layer with a bleachable image dye by exposure, developing the silver image and colour bleaching, characterised in that the colour bleaching is performed in the presence of at least one quinoxaline of formula (1) as the colour bleaching catalyst.
  • quinoxalines of formula (1) are admirably suited for this purpose. They are characterised by a very favourable position of their redox potentials and good solubility in the colour bleaching bath in the requisite concentrations. Particularly if the groups A, and A of formula (1) each represent a methyl group the quinoxalines according to the invention of formula (1) have a good activity and lead to a favourable gradation. In addition, when they are pres-.
  • Quinoxalines of formula (1) are appropriately prepared in per se known manner (cf J.C.E. Simpson, Condensed Pyridazine and Pyrazine Rings in A. Weissberger, The Chemistry of Heterocyclic Compounds, J. Wiley & Sons, New York, 1953, 203ff) by condensation of the corresponding aromatic 1,2-diamine with a 1,2-dicarbonyl compound.
  • diamine it is possible to use the corresponding more stable nitroaniline or the corresponding o-dinitro compound, which can be reduced to the desired diamine and then without intermediate separation reacted to give quinoxaline.
  • benzofuroxans or their reduction products can also be reduced to 1,2-diamines via intermediate stages (F.B. Mallory S.P. varimbi, J. Org. Chem., 28, l656ff, 1963) and condensed to quinoxalines.
  • 1,2-dicarbonyl compound it is also possible to react an a-substituted halogeno ketone of formula wherein X is a nucleophilic group, e.g. -l, -Br, -Cl, or -Ol-l with the o-diamine to give the corresponding 1,2- dihydroquinoxaline (J. Figueras, J. Org. Chem., 31, 803ff, I966), which is then oxidised in situ to quinoxaline.
  • X is a nucleophilic group
  • o-diamine 1,2- dihydroquinoxaline
  • the quinoxalines are obtained in better yield and greater purity if the condensation is performed under nitrogen.
  • a-Oximinoketones can also be reacted with 1,2- diamines to give quinoxalines (cf. J.C.E. Simpson, loc.
  • Preparation Instructions General instructions An appropriate o-dinitro derivative is dissolved in a suitable solvent, e.g.,”methanol, ethanol, glacial acetic acidor dimethyl formamide or also only suspended with 1 to percent by weight of hydrogenation catalyst e.g., a 10 percent palladium-carbon catalyst and hydrogenated under normal pressure, optionally with initial heating.
  • a suitable solvent e.g., methanol, ethanol, glacial acetic acidor dimethyl formamide
  • hydrogenation catalyst e.g., a 10 percent palladium-carbon catalyst and hydrogenated under normal pressure, optionally with initial heating.
  • the catalyst isfiltered off under N and the filtrate under N is mixed with an at least equimolar quantity of distilled or recrystallised diketone or a solution of the diketone in a suitable solvent, whereby in most cases a colour deepening occurs and the temperature rises.
  • the mixture is refluxed until the end of the reaction and the desired substance is isolated after cooling.
  • the product can be purified by recrystallising from a suitable solvent by distillation or if necessary by chromatography or sublimation.
  • the dinitro derivative it is possiblein some cases to use the corresponding o-nitroamino compound. If the o-diamino compound is single and obtainable with sufficient purity it can be reacted directly or in the form of its salt (hydrochloride, hydrosulphate, hydroperchlorate, etc.) with the corresponding diketone in a suitable solvent under nitrogen. When using a salt it is recommended that an equivalent quantity of sodium or potassium acetate be added to saturate the liberated acid.
  • the redox potentials are determined in the usual manner by means of polarography.
  • the solvent used is in all cases a mixture of dimethylformamide-ZN sulphuric acid in a ratio of 1:1.
  • the potential is measured relative to an Ag/AgCl electrode of known potential and then converted to the potential relative to a normal hydrogen electrode. Whereas in certain cases two single electron transitions, characterised by that two polarographic waves are observed in other cases only one polarographic wave is observed, corresponding to the average redox potential.
  • the hot solution is mixed with a freshly prepared solution of 36.5 g of 95 percent sodium-m-nitrobenzenesulphonate and 66g (1.45mol) of sodium hydroxide in 287ml of H 0 and 45ml of ethanol and refluxed for 2 hours. After cooling overnight 300ml of water are added and the solution distilled to 500ml. The residue from which already part of the desired product is precipitated is continuously extracted for 12 hours with 500ml of ethyl acetate.
  • This oil is mixed with 44ml of glacial acetic acid and 35ml,of acetic anhydride and after adding 0.55g of zinc powder is refluxed for 1 hour.
  • the still hot solution is poured onto 200ml of an ice-water mixture.
  • the resulting crystals are filtered off and dried at 60C in vacuo. Yield 47.8 percent of theory (based on the nitro compound) of m.p. 134.1C.
  • the thin-layer chromatogram in trichloromethanezmethanol 9:1 as the solvent system reveals a main spot, whilst the IR and NMR spectra show the strips characteristic of the structure. 2.
  • Example 1 On a l3 X 18cm glass plate is cast a solution of 3.3m] If instead of compound G compound Edissolved in of 6 percent gelatin, 2.0m] of a 1 percent solution of the dimethyl formamide is used, then proceeding as dehardener 2,4-dichloro-6-phenylamino-l,3,5-triazinoscribed in Example 1 again a clean positive image of 3'-sulphonic acid, 0.5ml of a 2.10 molar solution of 5 the exposed wedge is obtained. If instead of compound compound G in acetone and 4.2m] of water.
  • I OIH HOa S (104) dium acetate and 10ml of glacial acetic acid per and acovering layer. All these layers are hardened with litre of water; a halogenotriazine compound such as 2,4-dichloro-6- 3 rinse f 4 i t phenylamino-l,3,5-triazino-3'-sulphonic acid. 4. colour bleach for 6 minutes with a solution of 10g This Copying material is successively exposed under of potassium iodide in 1 1m of lN -sulphuric acid; a Step Wedge into the three Spectral areas blue (Kqdak 5 time for 2 minutes Wratten filter 2B+49), green (Kodak.
  • Wratten filter W t X29 d 6. bleach the remaining silver for 2 minutes with a g i d t an bath containing 150ml of 37 percent hydrochloric escnbed m xamp e eve ope or minutes an fixed. Subsequently bleaching takes place in a silver 5g of upper sulphate and 30g of potasslum bleaching bath containing per litre 27ml of 96percent bromide per litre;
  • Example 5 A photographic material as described in Example 3 is as stated exposed into the three spectral areas. Subsequently the copy is developed as follows:
  • Example 6 On a 13 X 18cm glass plate is cast a solution with the following composition: 3.3ml of a 6 percent gelatin, 3.3ml of a silver bromide emulsion containing 5.3g of silver per 100g of emulsion, 1.0ml of a 1 percent solution of the hardener described in Example 1, 03ml of a 1 percent solution of the blue-green dye of formula (101) and 2.1ml of water. After drying on the thus obtained layer is copied a step wedge and the plate is then treated as follows:
  • Example 7 A solution consisting of 3.3ml of 6 percent gelatin, 3.3ml of a silver bromide solution containing 5.3g of silver per 100g of emulsion, 1.0m] of a 1 percent solution of the hardener described in Example I, 0.3m! of a 1 percent solution of the blue-green dye of formula (10]) described in Example 1, 0.5m] of a 4.10 molar solution of compound G in acetone and 1.6ml of water is cast on a 13 X 18cm glass plate. After drying on the thus obtained layer a step wedge is copied (50 lux, 10 sec.) and the copy processed further as described in Example 1. After drying a clean bleached colourless positive image is obtained of the wedge used as the original.
  • Example 8 A photographic material as described in Example 3 is, as described in Example 3, exposed into the three spectral areas. The copy is then treated as follows:
  • Example 9 On a 13 X 18cm glass plate is cast a solution of 3.3m! of 6 percent gelatin, 2.0ml of a 1 percent solution of the hardener described in Example 1, 3.3m] of a silver bromide emulsion containing per 100g of emulsion, 5 .3 g of silver, 0.3m] of a 1 percent solution of the blue-green dye of formula (101) and 1.1m] of water. After drying, a step wedge is copied thereon (501lux, 3 sec.) and the copy is treated as follows:
  • Example 1 colour bleach for 6 minutes with a solution containing per litre 10g of potassium iodide, 27ml of 96.percent sulphuric acid and 10ml of a 4.10 molar solution of compound A, B, C or H in ethanol or in another suitable watermiscible, photographically inactive solvent. After briefly rinsing, the remaining silver is oxidised as described hereinbefore, rinsed and fixed. After thorough washing-out and drying in all cases a clean bleached co lourless image of the original used is obtained with a clearly graduated gradation.
  • Example 1 l A 13 X 18cm glass plate is coated with a solution of 3.3m] of 6 percent gelatin, 2.0ml of a 1 percent solution of the hardener described in Example 1, 3.3m] of a silver bromide emulsion containing 5.3g of silver per 100g of emulsion, 0.5m] of the yellow dye of formula and 0.9m] of water. After drying a step wedge is copied thereon lux, 5 sec.) and treated analogously to Examples 9 and 10, whereby instead of the compounds contained therein the colour bleaching bath contains 10ml of 4.10 molar solution of one of the substances B, F and .l in acetone or another suitable, watermiscible photographically inactive solvent. After drying a clean bleached colourless yellow image of the original used is obtained.
  • Example 12 On a photographic material as described in Example 10 a step wedge is exposed (500 lux, 10 sec.). The strip is well moistened with a lN-sulphuric acid containing 10 mo] of compound B per litre and subsequently brought into close contact with a polished iron plate. After briefly rinsing, fixing takes place followed by thorough rinsing.
  • A, and A are each an alkyl group with at most 5 carbon atoms, an at most bicyclic aralkyl group with 1 to 5 carbon atoms in the alkyl portion, an at most bicyclic aryl group or a 5 or 6-membered heterocyclic group having as hetero atoms N, O or S, and n is 1 or 2, whereby the oxygencontaining ring is connected with the quinoxaline group in the 5,6 or 6,7-position, as a colour bleaching catalyst.
  • Photographic material according to claim 1 which comprises a quinoxaline of formula wherein A and A are each an alkyl group with at most 5 carbon atoms, benzene, lower alkyl-benzene, lower alkoxy-benzene, hydroxybenzene, aminobenzene or halobenzene, and n is l or 2 as a colour bleaching catalyst.
  • Photographic material according to claim 2 which comprises a quinoxaline of formula Nj Ar N Au wherein A and A are each a methyl or phenyl group and n is l or 2 as a colour bleaching catalyst.
  • Photographic material according to claim 3 which comprises a quinoxaline of formula wherein A is a methyl or phenyl group and n is 1 or 2 as a colour bleaching catalyst.
  • Photographic material according to claim 4 which comprises a quinoxaline of formula /o NIom (CHM:
  • a and A are each an alkyl group with maximum 5 carbon atoms, an at most bicyclic aralkyl group with l to 5 carbon atoms in the alkyl portion, an at most bicyclic aryl group or a 5 or 6-membered heterocyclic group having as hetero atoms N, O or S, and n is l or 2, whereby the oxygen-containing ring is connected with the quinoxaline ring in the 5,6 or 6,7- position as the colour bleaching catalyst.
  • a quinoxaline of formula characterised in that as the colour bleaching catalyst a quinoxaline of formula is used, wherein A and A are each an alkyl group with maximum 5 carbon atoms, benzene, lower alkylbenzene, lower alkoxy-benzene, hydroxybenzene, aminobenzene or halobenzene, and n is l or 2.
  • n is l or 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US00176689A 1970-09-04 1971-08-31 Photographic colour material Expired - Lifetime US3767402A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1325170A CH543108A (de) 1970-09-04 1970-09-04 Verwendung von Chinoxalinen in photographischen Verfahren

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US3767402A true US3767402A (en) 1973-10-23

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US00176689A Expired - Lifetime US3767402A (en) 1970-09-04 1971-08-31 Photographic colour material

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US (1) US3767402A (enrdf_load_stackoverflow)
JP (1) JPS5333844B1 (enrdf_load_stackoverflow)
BE (1) BE772141A (enrdf_load_stackoverflow)
CH (1) CH543108A (enrdf_load_stackoverflow)
DE (1) DE2144298C2 (enrdf_load_stackoverflow)
FR (1) FR2109736A5 (enrdf_load_stackoverflow)
GB (1) GB1351789A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4145217A (en) * 1976-05-24 1979-03-20 Ciba-Geigy Ag Quinoxalines and their use in photographic processes
US4202698A (en) * 1976-05-24 1980-05-13 Ciba-Geigy Ag Quinoxalines and their use in photographic processes
US4323682A (en) * 1976-05-24 1982-04-06 Ciba Geigy Ag Quinoxalines and their use in photographic processes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2669517A (en) * 1952-12-10 1954-02-16 Gen Aniline & Film Corp Furoquinoxalines and thienoquinoxalines as catalysts in dye bleach baths for color photography
US3615494A (en) * 1968-07-16 1971-10-26 Fuji Photo Film Co Ltd Method of producing color photographic images by the silver dye bleach method
US3656953A (en) * 1969-03-13 1972-04-18 Ciba Geigy Ag Silver dyestuff bleaching process using quinoxaline catalyst

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1051970A (enrdf_load_stackoverflow) * 1964-03-20
CH433980A (de) * 1964-07-07 1967-04-15 Ciba Geigy Verwendung von Acylaminoverbindungen als Farbbleichkatalysatoren für das Silberfarbbleichverfahren
CH439964A (de) * 1964-12-10 1967-07-15 Ciba Geigy Verwendung von organischen Verbindungen als Katalysatoren für das Silberfarbbleichverfahren

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2669517A (en) * 1952-12-10 1954-02-16 Gen Aniline & Film Corp Furoquinoxalines and thienoquinoxalines as catalysts in dye bleach baths for color photography
US3615494A (en) * 1968-07-16 1971-10-26 Fuji Photo Film Co Ltd Method of producing color photographic images by the silver dye bleach method
US3656953A (en) * 1969-03-13 1972-04-18 Ciba Geigy Ag Silver dyestuff bleaching process using quinoxaline catalyst

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4145217A (en) * 1976-05-24 1979-03-20 Ciba-Geigy Ag Quinoxalines and their use in photographic processes
US4202698A (en) * 1976-05-24 1980-05-13 Ciba-Geigy Ag Quinoxalines and their use in photographic processes
US4323682A (en) * 1976-05-24 1982-04-06 Ciba Geigy Ag Quinoxalines and their use in photographic processes

Also Published As

Publication number Publication date
GB1351789A (en) 1974-05-01
DE2144298A1 (de) 1972-03-09
FR2109736A5 (enrdf_load_stackoverflow) 1972-05-26
DE2144298C2 (de) 1982-02-04
CH543108A (de) 1973-10-15
BE772141A (fr) 1972-03-03
JPS5333844B1 (enrdf_load_stackoverflow) 1978-09-18

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