US3689271A - Incorporation process for materials used to form photographic layers - Google Patents

Incorporation process for materials used to form photographic layers Download PDF

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Publication number
US3689271A
US3689271A US814808A US3689271DA US3689271A US 3689271 A US3689271 A US 3689271A US 814808 A US814808 A US 814808A US 3689271D A US3689271D A US 3689271DA US 3689271 A US3689271 A US 3689271A
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Prior art keywords
gelatine
solution
emulsion
alkyl
compound
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US814808A
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English (en)
Inventor
Fritz Nitttel
Erich Reckziegel
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Agfa Gevaert AG
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Agfa Gevaert AG
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/38—Dispersants; Agents facilitating spreading

Definitions

  • the present invention relates to a process for incorporating substances in materials which are used to form photographic layers and auxiliary layers.
  • colour couplers such as colour couplers, UV absorbers, white toners and similar additives may be incorporated in gelatine solutions by using so-called oil forming agents.
  • colour couplers are incorporated in water-soluble colloidal materials commonly used in the production of photographic products by dissolving the colour coupler in an organic liquid of relatively high boiling point which is insoluble in water, and emulsifying or dispersing the solution in the colloidal material.
  • hydrophilic developers e.g.
  • N-butyl-N-w-sulphobutylp-phenylenediamine penetrate the oil droplets only to a slight extent, if at all. This causes loss in sensitivity, flattening of the gradation and a reduced image density. Also, residues of hydrophobic developer may be retained in the droplets and cause fogging when the photographic material is treated in oxidising bleaching baths.
  • Hydrophilic substances such as colour couplers which carry a carboxyl group are incorporated in gelatine in the form of their sodium salts. Since the gelatine solutions are subsequently adjusted to a pH of 6.2 to 6.5, these compounds are generally present in microcrystalline distribution.
  • the protective colloidal action of gelatine is in many cases insufiicient, so that recrystallisation occurs influencing sensitivity, gradation and colour brilliance in an uncontrollable manner.
  • hydrophilic substances of the above mentioned types moreover, have the property of increasing the viscosity of the casting solution, in some cases to such an extent that such solutions can no longer be worked up.
  • R represents an alkyl or alkylene group which has 1 to 18 carbon atoms, preferably 5 to 12 carbon atoms and is branched and may be substituted, preferably by OH and/or OR groups
  • R represents a hydrogen atom, an alkyl or alkylene group which has 1 to 18 carbon atoms, preferably 5 to 12 carbon atoms and is branched and may be substituted, preferably by OH and/or OR groups
  • Q represents an alkyl group which has 1 to 9 carbon atoms and may be substituted, preferably by COOH, or one of the groups COX or -CH COX in which X may have the following meaning: (1) a hydrogen atom, a hydroxy group, an alkoxy group with 1 to 18 carbon atoms and preferably 5 to 12 carbon atoms, (2) an O-alkylene-[O-alkylene] -O-alkyl group in which the alkylene and alkyl radical preferably contain 1 to 4 carbon atoms and n denotes 0 to 10,
  • alkyl radical may contain up to 21 carbon atoms, is preferably branched and may in turn be substituted as may also the aryl radical, especially with such groups as OH, COOH, OCH CN and phenyl,
  • a hydrazine group which may be substituted by an alkyl group preferably having 1 to 5 carbon atoms or by the group which alkyl substituents may in particular be substituted by OH, COOH, OCH and CEN groups,
  • the radical i-C H appearing in many compounds in the above list represents the group l,1,3,5-tetramethylocten-(2)-yl whose structural formula is Versatic acid 911 is an isomeric mixture of highly branched tertiary and secondary carboxylic acids having 9 to 11 carbon atoms, and Versatic acid 1519 is a mixture of carboxylic acids of the same type having 15 to 19 carbon atoms.
  • the method of preparation of the compounds used in the present invention is generally known.
  • monoalkylated cyclic carboxylic acid anhydrides are reacted with alcohols or with amines.
  • Emulsifiable substances such as colour couplers, UV absorbents, white toners or stabilisers are dissolved together with the compounds according to the present invention, in an organic solvent which is immiscible with water and emulsified with the casting solution for the photographic layer, using an emulsifying apparatus.
  • the emulsifying apparatuses used for this purpose may, for example, be high speed stirrers, so-called mixing sirens, ultraturrax or ultrasound apparatuses.
  • Hydrophilic substances e.g. the above mentioned colour couplers which contain carboxyl groups or hydrophilic substances such as colour couplers which contain SO H groups are incorporated by a different method.
  • the compounds of the present invention are dissolved in an alkaline medium together with the additives which are present in an alkali soluble form and a wetting agent, and this solution is added with intensitive stirring to an acidified casting solution as explained above.
  • the pH of the casting solution is thereby shifted to 6.2-6.5.
  • Certain colour couplers which do not contain SO H or COOH groups and which are soluble in alkali as enolates can be incorporated in the same manner.
  • the compounds of the present invention have the advantage that, apart from a very pronounced tendency to prevent crystallisation, especially in the presence of colour couplers which have been incorporated by emulsification, they do not prevent the coupling of oxidised colour developers.
  • the compounds form soaps at alkaline pH values, i.e. during development.
  • the additives used with the compounds according to the present invention do not separate out in an alkaline medium. They therefore also prevent precipitation of the dye produced or the appearance or turbulent colour surfaces. The separation of colour components by crystallisation which might otherwise occur even during digestion is also prevented.
  • the compounds used according to the present invention cause neither flattening of the gradation nor reduction in the image density and in addition they substantially prevent the increase in viscosity which many colour couplers containing COOH or SO H groups cause during digestion.
  • the compounds of the present invention are generally employed in the proportion of 0.1 to 10 parts by weight per part by weight of the substance which is to be incorporated, the preferred range lying between 0.3 and 1 part by weight.
  • the use of higher concentrations of up to 10 parts by weight is of interest in cases in which only small quantities of an additive, e.g. a sta-biliser, are to be incorporated into the casting solution.
  • suitable organic solvents which are immiscible with Water are the chlorinated short-chained aliphatic compounds such as methylene dichloride, as well phatic compounds such as methylene di chloride, as well as ethyl acetate.
  • the binder used for the photographic layers is preferably gelatine but this may be partly replaced by other film-forming natural or synthetic polymers.
  • Suitable polymers for this purpose include alginic acid and its derivatives such as its salts, esters, or amides, carboxymethyl cellulose, alkyl cellulose, starch and its derivatives, polyvinyl alcohol, copolymers of vinyl alcohol and vinyl acetate, polyvinyl pyrrolidone, anionic polyurethanes and other latices such as copolymers of acrylic ester, acrylonitrile and acrylamide.
  • the photographic layers may contain any known additives such as anti-fog agents, stabilisers, hardeners, plasticisers and wetting agents. In addition, they may be both chemically and spectrally sensitised.
  • the light sensitive emulsions may be chemically sensitised by carrying out the ripening in the presence of small quantities of sulphur-containing compounds such as allyl isothiocyanate, allyl thiourea and sodium thiosulphate.
  • the light sensitive emulsions may also be sensitised with reducing agents, e.g. the tin compounds described in Belgian Pats. Nos. 493,464 and 568,687, and the iminoaminomethanesulphinic acid compounds described in Belgian Pat. No. 547,323 or small quantities of noble metal compounds such as compounds of gold, platinum, palladium, iridium, ruthenium and rhodium.
  • the emulsions may also be sensitised with polyalkylene oxide derivatives, e.g. a polyethylene oxide having a molecular weight of between 1000 and 20,000, condensation products of alkylene oxide and aliphatic alcohols, glycols, cyclic dehydration products of hexitols, alkyl substituted phenols, aliphatic carboxylic acids, aliphatic amines, aliphatic diamines and amides.
  • the condensation products have a molecular weight of at least 700, preferably more than 1000.
  • combinations of these sensitisers may, of course, be used as described in Belgian Pat. No. 537,278 and in British patent specification No. 727,982.
  • EXAMPLE 1 A solution of 40 g. of the following blue green coupler HsC 5 11 and 20 g. of Compound 3 dissolved in 160 cc. of ethyl acetate is emulsified in 1 kg. of a 10% gelatine solution at 50 C. After removal of the solvent in a thin layer evaporator, the emulsion is added to 1 kg. of a red sensitised silver halide gelatine emulsion which contains 0.33 mol of silver bromide, 0.0075 mol of silver iodide and g. of gelatine per kg.
  • the mixture prepared in this Way is used as a red sensitive layer containing a blue green coupler, in a multilayered colour photographic material in the usual manner.
  • EXAMPLE 2 40 g. of the following blue green coupler or: @iD-b ONHC Hu EXAMPLE 3 25 g. of the following purple coupler are emulsified in 1 kg. of 10% gelatine solution in the same manner as in Example 1 together with 12.5 g. of Compound 26 and added to 1 kg. of a green sensitised halide gelatine emulsion.
  • Example 1 The mixture is worked up as in Example 1.
  • the green sensitive layer has the same properties as the emulsion described in Example 1.
  • EXAMPLE 4 36 g. of the following yellow coupler iuHaa Q-o 001120 ONH- F COOH together with 18 g. of Compound 30 are dissolved in a mixture of 360 ml. of water, 40 ml. of 5 N NaOH, and the resulting solution 75 ml. of methanol and emulsified at 40 C. in 1 litre of a gelatine solution which contains 90 ml. of a 21% solution of monosodium citrate.
  • the emulsion thus formed has a pH of 6.1 and is added to 1 kg. of a blue sensitive silver halide gelatine emulsion which contains 0.33 mol of silver bromide, 0.0075 mol of silver iodide and 90 g. of gelatine per kg.
  • Example 2 The final mixture is worked up in the same manner as in Example 1 to give a blue sensitive layer which contains yellow coupler and has the same properties as the emulsion obtained in Example 1.
  • the coupler crystallises out after a short time.
  • EXAMPLE 5 22.5 g. of the following purple coupler together with 12 g. of Compound 28 and 1 g. of the his- (2-ethyl)-hexyl ester of sulphosuccinic acid as wetting agent are dissolved in a mixture of 230 ml. of water, 30 m1. of 5 N NaOH and 75 ml. of methanol and thesolution emulsified at 40 C. in 1 litre of a 10% gelatine solution which contains 40 ml. of a 21% monosodium citrate solution. The resulting emulsion is added to 1 kg. of a green sensitised silver halide gelatine emulsion which contains 0.33 mol of silver bromide, 0.0075 mol of silver iodide and g. of gelatine per kg.
  • EXAMPLE 6 25 g. of the following purple coupler l SOaH together with 12.5 g. of Compound 4 and 1 g. of the bis- (2-ethyl)-hexyl ester of sulphosuccinic acid as wetting agent are dissolved in a mixture of 250 ml. of water, 50 ml. of 1 N lithium hydroxide solution and 75 ml. of methanol and the solution emulsified at 40 C. in 1 litre of a 10% gelatine solution which contains 40 ml. of 21% monosodium citrate solution.
  • the emulsion is added to 1 kg. of a green sensitised silver halide gelatine emulsion which contains 0.33 mol of silver bromide 0.0075 mol of silver iodide and 90 g. of gelatine per kg.
  • the mixture is worked up as before.
  • Compound 4 is omitted the coupler crystallises out on digestion.
  • EXAMPLE 8 40 g. of the yellow coupler used in Example 7 together with 20 g. of Compound 2 are dissolved as indicated in that example and added to 1 kg. of a blue sensitive silver halide gelatine emulsion which contains 0.33 mol of silver bromide, 0.0075 mol of silver iodide and 120 g. of gelatine per kg. and to which 40 ml. of a 21% monosodium citrate solution have previously been added. The result is similar to that obtained in Example 6.
  • EXAMPLE 9 40 g. of the yellow coupler used in Example 7 together with 20 g. of Compound 7 are dissolved as described in that example and added to 1 kg. of a blue sensitive silver halide gelatine emulsion which contains 0.33 mol of silver bromide, 0.0075 mol of silver iodide and 120 g. of gelatine per kg.-The result'is similar to that obtained in Example 6.
  • EXAMPLE 10 30 g. of the following UV absorber Ho (min N together with 10 g. of Compound 25 are dissolved in ethyl acetate and emulsified in 1 kg. of a gelatine solution. The emulsion is cast as a UV protective layer over a colour photographic material.
  • the protective layer produced by the process according to the invention is clear whereas a layer produced without Compound 25 remains cloudy.
  • EXAMPLE 11 30 g. of the UV absorber used in Example 10 together with g. of Compound 28 are dissolved in ethyl acetate and emulsified in 1 kg. of a 10% gelatine solution. The emulsion is cast as a UV protective layer over a colour photographic material. The result is similar to that obtained in Example 10.
  • EXAMPLE 12 0.5 g. of the following white toner N- N O Cfis 100 mg. of a stabiliser of the following formula together with 3 g. of Compound 3 are dissolved in 10 ml. of methylene di chloride and the solution emulsified in 1 kg. of a 10% gelatine solution. The emulsion is used as a protective layer for colour photographic material.
  • Compound 3 prevents diffusion of the stabiliser into the adjacent layers.
  • EXAMPLE 14 22 g. of the following purple coupler together with 15 g. of Compound 28 and 1 g. of the bis- (2-ethy1)-hexyl ester of sulphosuccinic acid as wetting agent are dissolved in a mixture of 400 ml. of water, ml. of 5 N NaOH and 60 ml. of methanol and the solution emulsified at 40 C. in 1 litre of 10% gelatine solution which contains 40 ml. of a 21% monosodium citrate solution. The emulsion is added to 1 kg.
  • R represents an alkyl or unsaturated alkyl and has at least 5 carbon atoms
  • Q is COX or an alkyl having up to 9 carbon atoms and a COX substituent
  • X is hydroxy, alkoxy of up to 18 carbons which may be alkoxy or amino substituted, or amino substituted by alkyl or aryl radicals of up to 21 carbons 'which radicals can be OH, CN, alkoxy, carboxy or amine substituted, or a hydrazine or hydroxylamine radical and an amount effective to stabilize the emulsification.
  • R represents a branched alkyl or unsaturated alkyl and has from 5 to 12 carbon atoms
  • Q is COX or CH COX
  • X is hydroxy, alkoxy of up to 18 carbons which may be alkoxy or amino substituted, or amino substituted by alkyl or aryl radicals of up to 21 carbons which radicals can be OH, CN, alkoxy, carboxy or amine substituted, or a hydrazine or hydroxylamine radical and in an amount effective to stabilize the emulsification.
  • R represents an alkyl or unsaturated alkyl and has at least 5 carbon atoms
  • Q is COX or an alkyl having up to 9 carbon atoms and a COX substituent
  • X is hydroxy, alkoxy of up to 18 carbons which may be alkoxy or amino substituted, or amino substituted by alkyl or aryl radicals of up to 21 carbons which radicals can be OH, CN, alkoxy, carboxy or amine substituted, or a hydrazine of hydroxylamine radical and in an amount effective to stabilize the emulsification.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US814808A 1968-04-11 1969-04-09 Incorporation process for materials used to form photographic layers Expired - Lifetime US3689271A (en)

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Application Number Priority Date Filing Date Title
DE1772192A DE1772192C2 (de) 1968-04-11 1968-04-11 Verfahren zur Herstellung von lichtempfindlichen und nicht lichtempfindlichen Schichten für photographische Aufzeichnungsmaterialien

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BE (1) BE731288A (de)
DE (1) DE1772192C2 (de)
FR (1) FR2006109A1 (de)
GB (1) GB1222753A (de)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765897A (en) * 1970-10-09 1973-10-16 Agfa Gevaert Ag Process of incorporating additives into photographic emulsions
US3998641A (en) * 1973-12-10 1976-12-21 Agfa-Gevaert, A.G. Photographic material containing yellow couplers
FR2314517A1 (fr) * 1975-06-13 1977-01-07 Agfa Gevaert Ag Materiau photographique couleur contenant un derive d'hydroxyindane
US4003748A (en) * 1974-03-07 1977-01-18 Agfa-Gevaert, A.G. Incorporation process
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US4304769A (en) * 1974-09-17 1981-12-08 Eastman Kodak Company Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
EP0043037A1 (de) * 1980-07-01 1982-01-06 Agfa-Gevaert AG Dispergierverfahren
US4330606A (en) * 1979-09-08 1982-05-18 Agfa-Gevaert Ag Color photographic materials and color photographic images
US4339515A (en) * 1979-09-08 1982-07-13 Agfa-Gevaert Aktiengesellschaft Method of stabilizing color photographic materials and a color photographic material
US4368259A (en) * 1980-01-22 1983-01-11 Agfa-Gevaert Aktiengesellschaft Color photographic recording material containing an emulsified, hydrophilic color-forming compound
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4512969A (en) * 1974-09-17 1985-04-23 Eastman Kodak Company Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles
US5426019A (en) * 1993-12-30 1995-06-20 Eastman Kodak Company Color photographic element
US5451497A (en) * 1993-12-30 1995-09-19 Eastman Kodak Company Photographic dispersion having improved stability
EP0696758A1 (de) 1994-08-10 1996-02-14 Agfa-Gevaert AG Lichtempfindliches fotografisches Aufzeichnungsmaterial mit lichtabsorbierendem Farbstoff
US5580705A (en) * 1991-12-27 1996-12-03 Konica Corporation Method of bleaching silver halide color photographic light-sensitive materials using particular ferric chelates
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2455431A1 (de) 2003-10-23 2012-05-23 Fujifilm Corporation Tinte und Tintensatz zur Tintenstrahlaufzeichnung
EP2712894A1 (de) 2012-09-26 2014-04-02 Fujifilm Corporation Azoverbindung, wässrige Lösung, Tintenzusammensetzung, Tinte zur Tintenstrahlaufzeichnung, Tintenstrahlaufzeichnungsverfahren, Tintenpatrone zur Tintenstrahlaufzeichnung und tintenstrahlaufzeichnetes Material

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4959300A (en) * 1987-04-15 1990-09-25 Konica Corporation Silver halide photographic light-sensitive material with improved gradation balance
US5508147A (en) * 1993-01-04 1996-04-16 Eastman Kodak Company Color photographic element with improved resistance to thermal and photochemical yellowing and method thereof
GB2301444B (en) * 1995-03-23 1999-02-24 Eastman Kodak Co Photographic elements comprising cyan coupler dispersions with improved stability and increased activity
US5726003A (en) * 1996-08-15 1998-03-10 Eastman Kodak Company Cyan coupler dispersion with increased activity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE470936A (de) * 1940-02-24
US3287134A (en) * 1964-03-09 1966-11-22 Du Pont Photgraphic layers and their preparation

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765897A (en) * 1970-10-09 1973-10-16 Agfa Gevaert Ag Process of incorporating additives into photographic emulsions
US3998641A (en) * 1973-12-10 1976-12-21 Agfa-Gevaert, A.G. Photographic material containing yellow couplers
US4003748A (en) * 1974-03-07 1977-01-18 Agfa-Gevaert, A.G. Incorporation process
US4512969A (en) * 1974-09-17 1985-04-23 Eastman Kodak Company Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles
US4304769A (en) * 1974-09-17 1981-12-08 Eastman Kodak Company Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
FR2314517A1 (fr) * 1975-06-13 1977-01-07 Agfa Gevaert Ag Materiau photographique couleur contenant un derive d'hydroxyindane
US4052216A (en) * 1975-06-13 1977-10-04 Agfa-Gevaert, A.G. Color photographic material containing a hydroxyindane
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4339515A (en) * 1979-09-08 1982-07-13 Agfa-Gevaert Aktiengesellschaft Method of stabilizing color photographic materials and a color photographic material
US4330606A (en) * 1979-09-08 1982-05-18 Agfa-Gevaert Ag Color photographic materials and color photographic images
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US4368259A (en) * 1980-01-22 1983-01-11 Agfa-Gevaert Aktiengesellschaft Color photographic recording material containing an emulsified, hydrophilic color-forming compound
EP0043037A1 (de) * 1980-07-01 1982-01-06 Agfa-Gevaert AG Dispergierverfahren
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US5580705A (en) * 1991-12-27 1996-12-03 Konica Corporation Method of bleaching silver halide color photographic light-sensitive materials using particular ferric chelates
US5451497A (en) * 1993-12-30 1995-09-19 Eastman Kodak Company Photographic dispersion having improved stability
US5426019A (en) * 1993-12-30 1995-06-20 Eastman Kodak Company Color photographic element
EP0696758A1 (de) 1994-08-10 1996-02-14 Agfa-Gevaert AG Lichtempfindliches fotografisches Aufzeichnungsmaterial mit lichtabsorbierendem Farbstoff
EP2455431A1 (de) 2003-10-23 2012-05-23 Fujifilm Corporation Tinte und Tintensatz zur Tintenstrahlaufzeichnung
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2712894A1 (de) 2012-09-26 2014-04-02 Fujifilm Corporation Azoverbindung, wässrige Lösung, Tintenzusammensetzung, Tinte zur Tintenstrahlaufzeichnung, Tintenstrahlaufzeichnungsverfahren, Tintenpatrone zur Tintenstrahlaufzeichnung und tintenstrahlaufzeichnetes Material

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FR2006109A1 (de) 1969-12-19
GB1222753A (en) 1971-02-17
DE1772192A1 (de) 1971-03-04
DE1772192C2 (de) 1983-03-17
BE731288A (de) 1969-10-10

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