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US2186849A - Manufacture of photographic silver halide emulsions - Google Patents

Manufacture of photographic silver halide emulsions Download PDF

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Publication number
US2186849A
US2186849A US94340A US9434036A US2186849A US 2186849 A US2186849 A US 2186849A US 94340 A US94340 A US 94340A US 9434036 A US9434036 A US 9434036A US 2186849 A US2186849 A US 2186849A
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US
United States
Prior art keywords
acid
silver halide
emulsion
photographic
color former
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
US94340A
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English (en)
Inventor
Wilmanns Gustav
Bitterfield Kreis
Kumetat Karl
Frohlich Alfred
Schneider Wilhelm
Brodersen Richard
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GAF Chemicals Corp
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Agfa Ansco Corp
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    • 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/02—Azo compounds containing chains of eight or more carbon atoms not provided for elsewhere in this class

Definitions

  • Our present invention relates to the manufacture of silver halideemulsion layers.
  • a known method of producing photographic pictures in color consists in using photographic emulsions which contain dyestufi components adapted during the development to form dyestuffs with the products of oxidation of the developer used.
  • Dyestufi components which are suitable for this method are named in U. S. Patents Nos. 1,102,028 and 1,055,155.
  • developers which have a free amino-group for example para phenylene diarnine, para dimethylamino-aniline, or ethoxy-para-dimethylamino-aniline, a picture in color is obtained.
  • a further object of the invention is to provide a color photographic multi-layer material comprising a series of superimposed emulsion layers, each layer containing a dyestuif component which is fast to diffusion.
  • This invention is based on the observation that the diffusion of the dyestuif components may be 'Ininimized or completely suppressed by using as the component in the manufacture of the-photographic silver halide emulsion a dyestuff component of the type more narrowly defined below which has in its molecule an aliphatic carbon chain of more than 5 carbon atoms.
  • the carbon chain may also comprise any substituentsand may be derived from an aliphatic unsaturated hydrocarbon.
  • dy estufi' components which in a solution alkaline with sodium carbonate or caustic alkali react with the oxidation products of the developer may be named, for example, phenols, naphthols, amino-naphthols, aniline, naphthylamines; also all bodies which contain a reactive methylene group, for instance an aceto-acetic acid ester, a cyano-acetic acid ester, a benzoyl acetic acid ester, benzoylaceto-nitrile, hydrindene, pyrazolones, coumarone, hydroxythionaphthenes and the like.
  • the introduction into these dyestufl components of an aliphatic carbon chain of more than 5 carbon atoms may be brought about in known manner to produce a homopolar linkage between the aliphatic carbon chain and color former.
  • a union like that in an acid 'amide, may be produced by introducing into an amino-group of the dyestufl component the radical of an aliphatic acid having more than 5 carbon atoms, for instance caprylic acid, lauric acid, undecylic acid, stearic acid, palmitic acid, oleic acid, erucic acid, melissic acid, cerotic acid, and stearolic acid, or by combining an acid group of the dyestufl?
  • an hydroxy-group in the dyestuff component may be acylated by means of an aliphatic chloride having more than 5 carbon atoms, for instance, the chloride of one of the above enumerated acids, or the dyestufl component may be synthesized from parent materials which already contain an aliphatic carbon chain of more than 5 carbon atoms.
  • dyestufi forming components are obtained if the aforementioned dyestufl! components contain besides an aliphatic carbon chain of more than 5 carbon atoms one or more groupings which render the compounds water soluble, for instance, the carboxyl group,.the sulfonic acid group, the thiosulfonic acid group,
  • the grouping which renders the components water soluble may also be introduced in the aliphatic radical which latter is introduced for making the component fast to diffusion.
  • Particularly suitable are such dyestufi components having in the aliphatic radical a double bond, since these double bonds can easily be sulfonated under such conditions that sulfonation at an undesired place is with certainty excluded.
  • Another possibility of introducing a grouping which renders the dyestuff component water soluble into the aliphatic radical consists in reacting the amino group of a dyestuif component containing an amino group with a halogen fatty acid halide and exchanging the halogen atom in the fatty acid radical for a sulfo group by boiling with sodium sulfite.
  • a dyestufi component thus obtained may be introduced into the photographic emulsion at any stage of its production.
  • the component is retained very firmly in the layer cast from the emulsion and the diffusing capacity of the component is the more diminished the higher is the number of carbon atoms in the aliphatic chain. If one selects a sufficiently large aliphatic radical, for example that of stearic acid, any diffusion of the dyestufi' component during the application of the layers or during the development of the finished composite photographic material may be completely prevented. Only with the use of emulsion layers of the kind described is the complete prevention of diffusion of the dyestuft component possible; multiple-color photographic.
  • Example 1 --1 mol. of l-(para-aminophenyD- 3-methyl-5-pyrazolone (either free or in the form offhydrochloride) is dissolved in dry pyridine and 1 mol. of stearic acid chloride is added. After heating for 1 hour on the water-bath the product is isolated by pouring the mass into water. 4 grams of this l-(para-stearyl-aminophenyl)-3-methyl-5-pyrazolone are dissolved in 3 cc. of caustic soda lye of 20 per cent strength and about 50 cc. of water. and the solution is added to 1000 grams of a photographic silver halide emulsion.
  • Example 2.1 mol. of l-(meta-aminophenyl)- 3-methyl-5-pyrazolone is dissolved in dry pyridine and there is added 1 mol. of oleic acid chloride. After warming for an hour on the waterbath the product is isolated by pouring the mass into water. 4 grams of this l-(meta-oleylaminophenyl)-3-methyl-5-pyrazolone are dissolved in 3 cc. of caustic soda lye of 20 per cent strength and 50 cc. of water and the solution is added to 1000 grams of a silver halide emulsion.
  • Example 3 -l mol. of octodecylamine is dissolved in dry pyridine and 1 mol. of l-hydroxy- Z-naphthoylchloride is added. After heating for 1 hour on the water-bath the product is isolated by pouring the mass into water. 4: grams of this 'octodecyl-1-hydroxy-Z-naphthoylamine are dissolved in 5 cc. of caustic soda lye of 20 per cent strength and about 50 cc. of methanol and the solution is added to 1000 grams of photographic silver halide emulsion.
  • the multi-layer film ismade, for example, as
  • an emulsion layer nonsensitized for color which contains per kilo of emulsion 10 grams of decanoyl-p-aminobenzoylacetic acid-para-anisidide.
  • the layers of emulsion may be applied in any other order. Filter layers may also be used.
  • Example 4 --p-Aminobenzoylacetanilide is converted into p-lauryl-aminobenzoylacetanilide by means of lauryl chloride. 5 grams of p-laurylaminobenzoylacetanilide and 2 cc. of a caustic soda solution of 50 per cent strength are dissolved in 50 cc. of methanol and the solution is added to 1 kilo of a silver halide gelatin emulsion. The photographic layers cast from this emulsion yield a yellow dyestuff picture after developing with p-diethylaminoaniiine.
  • Example 5 -m-Aminobenzoylacetanilide pcarbonic acid is converted into m-stearylaminobenzoylacetanilide-p'-carbonic acid by means of stearic acid chloride. 5 grams of m-stearylaminobenzoylacetanilide-p'-carbonic acid and 5 cc. of a caustic soda solution of 20 per cent strength are dissolved in 50 cc. of methanol and added to 1 kilo of a silver halide emulsion. Photographic layers cast from this emulsion yield after development with p-diethylaminoaniline a yellow dyestufl picture.
  • Example 6 -1 molecular proportion of phenylhydrazine-B-sulfor'ric acid is condensed by means of 1 molecular prcportio'n of p-nitro-benzoylacetic acid ester to l-(3'-suliophenyl)-3-(4"- nitrophenyl) -5-pyrazolone and this compound is reduced according to known methods to 1-(3'- sulfophenyl) 3 (4 aminophenyl) 5 -pyrazolone. The amino group of this compound is furthermore linked to stearic acid.
  • Example 7.-1 (m-stearylaminophenyl) 3 methyl-E-pyrazolone of Example 3 is sulfonated in concentrated sulfuric acid by means of 15 per cent of fuming sulfuric acid. In this reaction the sulfur group probably enters the meta-position with relation to the acylamino group. 10 grams of the sodium salt of 1-(5'-sulfo-3- stearylaminophenyl)-3-methyl-5-pyrazolone are dissolved in 50 cc. of water and added to 1 kilo of the silver halide emulsion. Photographic layers cast from this emulsion yield by development with p-diethylaminoaniline a red dyestuil picture with a cast te yellow.
  • Example 8 Aminophenolmethylpyrazolone is condensed with oleic acid chloride and the condensation product is sulfonated. When this product is added to a photographic silver halide emulsion, a layer cast from said emulsion is developed a red tint with p-dimethylaminoaniline after exposure.
  • Example ,9.a-hydroxynaphthoic acid chloride is condensed with oleyl amine and the product of condensation'is sulfonated.
  • a photographic silver halide emulsion layer containing the condensation product is developed a blue tint after 'exposure.
  • Example 10 --p-aminobenzoylacetanilide is condensed with a-bromostearic acid bromide and the condensation product is boiled with sodium sulfite. A photographic silver halide emulsion layer containing the product is developed a yellow tint after'exposure.
  • the photographic layers containing a dyestufi component rendered fast against diffusion may be quite generally applied for the purpose of color. photography. They may be applied in all proc-- been hitherto used for the same purpose, is based on the fact that the compounds in accordance with the present invention are absolutely fast to diffusion, even if they are most easily soluble in water, and that a carbon chain in accordance with the invention may be easily introduced into any dyestufi intermediate product molecule with out impairing thereactivity of this molecule.
  • Example 11.1 kilo of silver bromide emulsion is mixed with an aqueous solution of 15 grams of the sodium salt of 4"-stearylaminobenzoyl-3'- aminobenzoyl l-amino-8-hydroxynaphthalene 3.6-disulfonic acid. This emulsion is cast on a support to form a photographic layer. After exposure, development and fixing the silver picture is made in known manner into a dianisidineantitetraazotate picture. When immersing this antitetraazotate silver picture in' a dilute acid, a pure blue azo dyestuff picture is produced.
  • layers containing the components may be dyed with a suitable filtering dye.
  • Example 12 According to a. modification an amine capable of being diazotized is contained in the gelatin or silver halideemulsion, for instance, p-aminododecylbenzene or o-aminosulfooleylbenzene, and the silver picture is in known manner converted into an insoluble nitrite compound. Ii diazotation is started in optional manner, a dyestuff picture is obtained in the presence of a second azo coupling component. This second azo component can however be contained in the layer together with the amine capable of diazotation and may have been made fast to diffusion in any manner.
  • a. modification an amine capable of being diazotized is contained in the gelatin or silver halideemulsion, for instance, p-aminododecylbenzene or o-aminosulfooleylbenzene, and the silver picture is in known manner converted into an insoluble nitrite compound. Ii diazotation is started in optional manner, a dyestuff
  • Example 13.1 kilo of silver bromide emulsion is mixed with an aqueous solution of the sodium salt of 6-undecy1-2-hydroxy-l-benzoic acid, and this emulsion is made into photographic layers. After development, fixing and bleaching of a silver picture produced in this layer, the diazo compound from 4-aminodiphenylamine is in known. manner adsorbed at the silver ferrocyanide. After washing, coupling is effected by immersing the photographic layer in a. soda solution of 1 per cent strength and a yellow dyestuff picture is obtained. It is also possible to add to the emulsion at any stage before casting the fatty acid amide of an aminated leuco compound, for. instance, of an aminoindoxyl, and this may be oxidized to a dyestufl by treatment with lead chromate.
  • a photographic silver halide emulsion containing a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneimine-, azomethine, and azo dyestuffs, and having an alkyl radical of a carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a homopolar linkage.
  • a photographic silver halide emulsion con- 75 taining a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneimine-, azomethine, and azo dyestuils, and having an alkyl radical of an unsaturated carbon chain of more than carbon atoms linked to an atom of its molecule by a homopolar linkage.
  • a photographic silver halide emulsion containing a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneimine-, azomethine, and azo dyestuffs, and having an alkyl radicle of a substituted carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a homopolar linkage.
  • a photographic silver halide emulsion containing a color former fast to difiusion said color former being capable of forming a dye selected from the group consisting of quinoneimine, nzornethine, and azo dyestufis, said color former having an alkyl radical of a carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a homopolar linkage, and being substituted by a substituent whichimparts solubility in water to said color former.
  • a photographic silver halide emulsion containing a color former fast to diifusion said color former being capable of forming a dye selected from the group consisting of quinoneimine, azomethine--, and azo dyestuffs, said color former having an alkyl radical of a carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a homopolar linkage, and being substituted by at least one radical selected from the group consisting of carboxylic acid, sulfonic acid-, thiosulfonic acid-, arsenic acid-, and hydroxyl radicals.
  • a photographic silver halide emulsion containing a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneimine-, azomethine. and azo dyestufis, said color former having in its molecule an amino group substituted by an aliphatic acyl radical having a carbon chain of more than 5 carbon atoms.
  • a photographic silver halide emulsion containing a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneimine, azomethine, and azo dyestuffs, said color former having in its molecule an acid group substituted by an alkyl-amino radical having a carbon chain of more than 5 carbon atoms.
  • a silver halide gelatin emulsion for color photography containing a color former fast to diffusion with respect to the gelatin, said color former being capable of forming a dyestufi selected from the group consisting of quinoneiminc-, azomethine-, and azo dyestuffs in situ with a silver picture upon being contacted with a color forming developer, and having an alkyl radical of a carbon chain of 11 to 18 carbon atoms linked to an atom of its molecule by a homopolar linkage.
  • a silver halide gelatin emulsion for color photography containing a color former fast to diffusion with respect to the gelatin, said color former being capable of forming a dyestufl selected from the group consisting of quinoneimine, azomethine, and azo dyestufis in situ with a silver picture upon being contacted with a color forming developer, and having an alkyl radical of an unsaturated carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a homopolar linkage, said carbon chain being substituted by radicals which impart solubility in water to said color former.
  • a silver halide gelatin emulsion for color photography containing a color former fast to diffusion with respect to the gelatin, said color former being capable of forming a dyestuff selected from the group consisting of quinoneimine-, azomethine, and azo dyestuffs in situ with a silver picture upon being contacted with aggregater forming developer, said color former containing in its molecule an amino radical substituted by an aliphatic acid radical with a chain of from 11 to 18 carbon atoms.
  • a silver halide gelatin emulsion for color photography containing a color former fast to diffusion with respect to the gelatin, said color former being capable of forming a dyestufl selected from the group consisting of quinoneimine, azomethine--, and azo dyestuffs in situ with a silver picture upon being contacted with a color forming developer, said color former containing in its molecule an acid radical substituted by the radical of an aliphatic amine with a carbon chain of 11 to 18 carbon atoms.
  • a color photographic light-sensitive element comprising a support and a plurality of superposed silver halide gelatin emulsion layers, each layer containing a color former fast to difiusion with respect to the gelatin, said color former being capable of forming a dyestuff selected from the group consisting of quinoneimine-, azomethine-, and azo dyestuffs in situ with a silver picture upon being contacted with a color forming developer, and having an alkyl radical of a carbon chain of 11 to 18 carbon atoms linked to an atom of its molecule by a homopolar linkage.
  • a photographic silver halide emulsion containing a color former fast to diffusion said color former being capable of forming a dye selected from the group consisting of quinoneamine-, azomethine, and azo dyestuffs, and having an alkyl radicle of a carbon chain of more than 5 carbon atoms linked to an atom of its molecule by a linkage selected from the class consisting of a carbon to carbon linkage, an ester linkage and an acid amide linkage.
  • said color former is capable of producing the dyestufl by color forming development, wherein said carbon chain contains from 11 to 18 carbon atoms and is substituted by radicals imparting solubility in water to said color former.
  • KARL KUMETAT ALFRED FRGHLICH. WILHELM SCHNEIDER. RICHARD BRODERSEN.

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Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415382A (en) * 1944-03-31 1947-02-04 Du Pont Photographic elements including hydrophilic color formers
US2415381A (en) * 1944-03-31 1947-02-04 Du Pont Hydrophilic colloid color formers and photographic elements containing the same
US2423460A (en) * 1944-03-31 1947-07-08 Du Pont Photographic elements containing polyamide dye intermediate layers
US2425503A (en) * 1944-05-20 1947-08-12 Gen Aniline & Film Corp Nondiffusing couplers for color photography
US2435173A (en) * 1944-06-07 1948-01-27 Gen Aniline & Film Corp Acetyl n-heterocyclic couplers for color photography
US2435616A (en) * 1944-07-07 1948-02-10 Eastman Kodak Co Elimination coupling with azosubstituted couplers
US2437063A (en) * 1940-08-08 1948-03-02 Gen Aniline & Film Corp Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography
US2449244A (en) * 1945-01-25 1948-09-14 Gen Aniline & Film Corp Thioindoxyl couplers for color photography
US2450747A (en) * 1945-02-09 1948-10-05 Eastman Kodak Co Photographic emulsion containing nitraniline sulfonic acids
US2500487A (en) * 1948-11-09 1950-03-14 Gen Aniline & Film Corp Yellow diffusion-fast color formers of the benzimidazole class
US2530349A (en) * 1947-04-30 1950-11-14 Gen Aniline & Film Corp Cyan color formers capable of yielding fine grain images
US2545687A (en) * 1947-04-30 1951-03-20 Gen Aniline & Film Corp N-substituted benzimidazoles
US2567750A (en) * 1945-10-25 1951-09-11 Du Pont Light sensitive elements for color photography
US2571698A (en) * 1948-06-02 1951-10-16 Eastman Kodak Co Photographic masking process
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2591642A (en) * 1950-01-10 1952-04-01 Gen Aniline & Film Corp Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group
US2592864A (en) * 1945-11-28 1952-04-15 Dufay Chromex Ltd Color photography
US2635535A (en) * 1946-01-31 1953-04-21 Du Pont Mordanting
US2671021A (en) * 1950-12-27 1954-03-02 Gen Aniline & Film Corp Polymeric magenta color former
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions
US2688538A (en) * 1949-07-15 1954-09-07 Ici Ltd Photographic elements and process of color correction utilizing styryl dyes as couplers
US2694635A (en) * 1951-12-05 1954-11-16 Eastman Kodak Co Couplers for color photography
US2694718A (en) * 1951-12-05 1954-11-16 Eastman Kodak Co Sulfobenzamides
US2695233A (en) * 1950-12-09 1954-11-23 Gen Aniline & Film Corp Irreversibly dischargeable photographic filter layers and method of processing film containing the same
US2701197A (en) * 1951-12-15 1955-02-01 Eastman Kodak Co Nonpolymeric sulfonated hydroquinone antistain agents
US2704710A (en) * 1950-04-18 1955-03-22 Gen Aniline & Film Corp Precipitation of azo dyes in silver halide emulsions by means of guanidine and biguanide compounds containing long alkyl chains
US2723197A (en) * 1951-03-23 1955-11-08 Gen Aniline & Film Corp Silver halide emulsions for black and white prints containing brightening agents
US2772163A (en) * 1953-04-17 1956-11-27 Eastman Kodak Co Photographic emulsions containing couplers and hydrosols
US2829975A (en) * 1956-04-26 1958-04-08 Gen Aniline & Film Corp 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
US2902366A (en) * 1956-10-23 1959-09-01 Gen Aniline & Film Corp Acylated 3-aminopyrazolone couplers
US2908573A (en) * 1956-07-25 1959-10-13 Eastman Kodak Co Photographic color couplers containing mono-n-alkyl groups
US2993791A (en) * 1957-10-31 1961-07-25 Gen Aniline & Film Corp Color couplers containing long chain alkylaminoisophthalicester groups
US3008827A (en) * 1957-06-19 1961-11-14 Gevaert Photo Prod Nv Production of colored photographic images
US3042521A (en) * 1957-12-26 1962-07-03 Gen Aniline & Film Corp Antifoggants and stabilizers for photographic silver halide emulsion
US3112198A (en) * 1959-06-18 1963-11-26 Gen Aniline & Film Corp Non-diffusing color formers in which the long aliphatic chain thereon is provided with a terminal sulfo group
US3413072A (en) * 1964-02-04 1968-11-26 Oreal Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone

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DE744264C (de) * 1938-07-14 1944-01-13 Ig Farbenindustrie Ag Verfahren zum Herstellen farbiger photographischer Bilder mit Hilfe diffusionsechter Farbstoffbildner

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2437063A (en) * 1940-08-08 1948-03-02 Gen Aniline & Film Corp Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography
US2415382A (en) * 1944-03-31 1947-02-04 Du Pont Photographic elements including hydrophilic color formers
US2423460A (en) * 1944-03-31 1947-07-08 Du Pont Photographic elements containing polyamide dye intermediate layers
US2415381A (en) * 1944-03-31 1947-02-04 Du Pont Hydrophilic colloid color formers and photographic elements containing the same
US2425503A (en) * 1944-05-20 1947-08-12 Gen Aniline & Film Corp Nondiffusing couplers for color photography
US2435173A (en) * 1944-06-07 1948-01-27 Gen Aniline & Film Corp Acetyl n-heterocyclic couplers for color photography
US2435616A (en) * 1944-07-07 1948-02-10 Eastman Kodak Co Elimination coupling with azosubstituted couplers
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2449244A (en) * 1945-01-25 1948-09-14 Gen Aniline & Film Corp Thioindoxyl couplers for color photography
US2450747A (en) * 1945-02-09 1948-10-05 Eastman Kodak Co Photographic emulsion containing nitraniline sulfonic acids
US2567750A (en) * 1945-10-25 1951-09-11 Du Pont Light sensitive elements for color photography
US2592864A (en) * 1945-11-28 1952-04-15 Dufay Chromex Ltd Color photography
US2635535A (en) * 1946-01-31 1953-04-21 Du Pont Mordanting
US2530349A (en) * 1947-04-30 1950-11-14 Gen Aniline & Film Corp Cyan color formers capable of yielding fine grain images
US2545687A (en) * 1947-04-30 1951-03-20 Gen Aniline & Film Corp N-substituted benzimidazoles
US2571698A (en) * 1948-06-02 1951-10-16 Eastman Kodak Co Photographic masking process
US2500487A (en) * 1948-11-09 1950-03-14 Gen Aniline & Film Corp Yellow diffusion-fast color formers of the benzimidazole class
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions
US2688538A (en) * 1949-07-15 1954-09-07 Ici Ltd Photographic elements and process of color correction utilizing styryl dyes as couplers
US2591642A (en) * 1950-01-10 1952-04-01 Gen Aniline & Film Corp Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group
US2704710A (en) * 1950-04-18 1955-03-22 Gen Aniline & Film Corp Precipitation of azo dyes in silver halide emulsions by means of guanidine and biguanide compounds containing long alkyl chains
US2695233A (en) * 1950-12-09 1954-11-23 Gen Aniline & Film Corp Irreversibly dischargeable photographic filter layers and method of processing film containing the same
US2671021A (en) * 1950-12-27 1954-03-02 Gen Aniline & Film Corp Polymeric magenta color former
US2723197A (en) * 1951-03-23 1955-11-08 Gen Aniline & Film Corp Silver halide emulsions for black and white prints containing brightening agents
US2694635A (en) * 1951-12-05 1954-11-16 Eastman Kodak Co Couplers for color photography
US2694718A (en) * 1951-12-05 1954-11-16 Eastman Kodak Co Sulfobenzamides
US2701197A (en) * 1951-12-15 1955-02-01 Eastman Kodak Co Nonpolymeric sulfonated hydroquinone antistain agents
US2772163A (en) * 1953-04-17 1956-11-27 Eastman Kodak Co Photographic emulsions containing couplers and hydrosols
US2829975A (en) * 1956-04-26 1958-04-08 Gen Aniline & Film Corp 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
US2908573A (en) * 1956-07-25 1959-10-13 Eastman Kodak Co Photographic color couplers containing mono-n-alkyl groups
US2902366A (en) * 1956-10-23 1959-09-01 Gen Aniline & Film Corp Acylated 3-aminopyrazolone couplers
US3008827A (en) * 1957-06-19 1961-11-14 Gevaert Photo Prod Nv Production of colored photographic images
US2993791A (en) * 1957-10-31 1961-07-25 Gen Aniline & Film Corp Color couplers containing long chain alkylaminoisophthalicester groups
US3042521A (en) * 1957-12-26 1962-07-03 Gen Aniline & Film Corp Antifoggants and stabilizers for photographic silver halide emulsion
US3112198A (en) * 1959-06-18 1963-11-26 Gen Aniline & Film Corp Non-diffusing color formers in which the long aliphatic chain thereon is provided with a terminal sulfo group
US3413072A (en) * 1964-02-04 1968-11-26 Oreal Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone

Also Published As

Publication number Publication date
NL49334C (nl)
FR810401A (fr) 1937-03-22
BE416898A (nl)

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