US3180734A - Light sensitive photographic color element - Google Patents

Light sensitive photographic color element Download PDF

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Publication number
US3180734A
US3180734A US67483A US6748360A US3180734A US 3180734 A US3180734 A US 3180734A US 67483 A US67483 A US 67483A US 6748360 A US6748360 A US 6748360A US 3180734 A US3180734 A US 3180734A
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color
group
radical
compounds
photographic
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Expired - Lifetime
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US67483A
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Willems Jozef Frans
Koerber Willem Karel
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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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
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds

Definitions

  • a silver salt image and a color image are formed, the latter being formed by the reaction of the oxidation productsV of the color developing substances such as the usual p-dialkyl phenylene diamines with a color coupler present in said silver halide layer to form a dye.
  • a variant of this process consists in preparing a dispersion of silver halide grains in an aqueous solution of a hydrophilic binding agent, to emulsify this dispersion in a solution of -a hydrophobic binding agent in an organic solvent which is not miscible with water, and to emulsify thereafter the emulsion thus obtained in anaqueous solution of a hydrophilic layer-forming binding agent.
  • This method is described in the Belgian patent speciiication 551,312.
  • Still other -variants are:
  • a photographic emulsion prepared in a water-insoluble but water-permeable binding agent is dispersed in a water-soluble binding agent, e.g. gelatin or polyvinyl alcohol (US. patent specifications 2,490,749 and 2,548,526).
  • a water-soluble binding agent e.g. gelatin or polyvinyl alcohol (US. patent specifications 2,490,749 and 2,548,526).
  • R1 represents a member selected from the group consisting of an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group and a substituted aralkyl group;
  • R2 represents a member selected from the group consisting of a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group and a substituted aralkyl group;
  • R3 represents a member selected from the group consisting of a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, a hydroxyl group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, a hydrazino group and a substituted hydrazinno group;
  • R4 represents a member selected from the group consisting of an oxygen atom and an oxime group
  • X represents a member selected from the group consisting of a hydrogen atom and an acyl radical
  • Examples of compounds which correspond to the general formulae of this invention are among others: alphahydroxy (or alphaaryloxy)-acyl acetic acid esters II O OH O OCOR and the products which are formed by saponication or both by saponiiication and dicarboxylation, as well as the conversion products of these compounds, with amines, hydrazines, hydrazides and sulphonyl hydrazides.
  • This product can be prepared according to the description given in J. Chem. Soc. 1942, page 205.
  • This compound can be prepared by treating 2 mol of caprylic acid ester with a sodium dispersion according to I. Am. Chem. Soc., 57 (1935), page 2302.
  • the compounds according to the general Formulae I and IL dissolved in a suitable solvent are mixed with a solution of gelatin or of another binding agent Wherefrom the intermediate layers mentioned hereinbefore are prepared.
  • these compounds are used in a material which is composed of dispersed differently sensitized emulsion droplets such as for instance described in and known from the Belgian patent specifications 536,673 and 551,312, these compounds can be added to the intermediate discontinuous phases as well as to the outer continuous phases.
  • the inner discontinuous phase consists of two color sensitive emulsions and the hydrophilic outer continuous phase contains the non-sensitized emulsion and a color coupler for yellow, it is necessary to add these compounds to the hydrophobic intermediate discontinuous phase.
  • the amount is chosen lin such a way that the content of active compound lays between about 0.025 g. and 2 g. per sq m. of intermediate layer which corresponds with a concentration of 0.100 g. to 20 g. per litre of :intermediate layer solution. This concentration is not critical and can if necessary be shifted up to higher limits.
  • the compounds are poorly miscible with the aqueous colloid layers with which. they are mixed before casting, the compounds can be dispersed therein by means of a suitable emulsifying agent.
  • a suitable emulsifying agent are among other sodium salts of alkyl benzene sulphonic acids having surface-active properties.
  • a yellow filter layer between the bluesensitive layer and the green-sensitive layer in order to eliminate the sensitivity to blue of the emulsion layers sensitive respectively to green and to red.
  • a yellow iilter layer is usually composed of colloidal silver.
  • the compounds according to the present invention can advantageously be used in the yellow lter layer since the colloidal silver exercises an oxidizing effect on the usual color developers whereby these oxidation products can diffuse to an adjacent emulsion layer to produce an undesirable color. If the compounds according to the present invention are used, these oxidation products are immediately reduced again whereby their noxious f action is excluded.
  • FIG. 1 is a diagrammatic illustration of an otherwise conventional three-layer color material in which one of the novel reducing agents of this invention is incorporated in the yellow filter layer separating the blue-sensitive and green-sensitive layers and in an interlayer separating the green-sensitive and red-sensitive layers.
  • FIG. 2 is a similar illustration of an alternative embodiment in which the several emulsions are dispersed in a common colloid layer which contains the reducing agent of the invention.
  • Example 1 A photographic color material which is composed of respectively a suitable support, a red-sensitized silver halide layer containing a colorcoupler for cyan, an intermediate layer consisting of Compound according to Prep. 1 2 g.
  • the further finishing process is executed in the commonly known baths.
  • a color image is obtained showing a much better color reproduction than the color reproduction of a .color photographic material, simillarly composed and finished but comprising intenlayers which were coatedfrom a pure gelatin solution.
  • This improved color reproduction can e.g. be measured in the following way: a green selection of the three-layer material to be tested is made. Next, the H and D-curve of this green-selection is measured behind greenand rediilter in the Ansco-densitometer, and that step of the curves is selected the density of which behind the red filter is nearest to 0.50; the density x behind green filter is measured on the same step.
  • Example 2 The same photographic color material and processing as in Example l, but instead of 2 g. of the compound according to Preparation 1, 1.5 g. of the compound according to Preparation 2 are added to the gelatin intermediate layers.
  • the improved color reproduction obtained is expressed by a considerably improved measured side-absorption of 23.7% as against 37% of a same material without this compound in the intermediate layers.
  • Example 5 The same photographic color material and processing as in Example 1, but instead of 2 g. of the co-mpound according to Preparation l, 2 g. of the compound according to Preparation 3 are added to the gelatin intermediate layers and to the yellow filter layer.
  • the improved color reproduction obtained is expressed by a considerably improved measuredside-absorption of 26% as against 37% of a same material without this compound in the intermediate layers.
  • Example 4 A same photographic color material and processing as in Example l, 'but instead of 2 g. of the compound according to Preparation 1, 1 g. of the compound according to Preparation 4 is added to the gelatin intermediate layer and to the yelow filter layer.
  • the improved color reproduction obtained is expressed by a considerably improved measured side-absorrption of 25% as against 37% of a same material without this compound in the intermediate layers.
  • Example 5 50 cm.3 of a red-sensitized silver chloride emulsion with normal gradation, containing a color coupler for cyan, are mixed with 0.6 cm.3 of 10% aqueous solution of a polystyrene maleic anhydride composed of equimolecular amounts of both monomers. 5 g. of the butyraldehyde polyvinyl acetal known as Pioloform DS (registered trademark) .are dissolved in 25 cm.3 of chloroform, 25 cm.3 of amyl alcohol and 45 cm.3 of carbon tetrachloride. The photographic emulsion is emulsitied in the polyvinyl acetal solution with a colloid mill or a homogenizer.
  • Pioloform DS registered trademark
  • a green-sensitized silver chloride emulsion containing a color coupler for magenta is prepared and a blue-sensitive photographic emulsion containing a color coupler for yellow are prepared.
  • each of the emulsions thus obtained is again separately emulsiiied in 150 cm.3 of a 6% aqueous gelatin solution containing l g. of the compound according to Preparation 1 dissolved in 20 em of ethanol.
  • these three complex emulsions are mixed and coated onto a paper support.
  • color development as in Example l and lrther finishing the three different colors are formed in the three different inner phases. The color reproduction and the color separation are much better than in a material which is composed in quite the same way but wherein no compound was added to the gelatin phase.
  • Example 6 The same emulsion preparation and the same finishing as in Example 5 but 2 g. of the compound according to Preparation l are added per each 100 cm.3 of solvent to the hydrophobic phases consisting of butyraldehyde polyvinyl acetal.
  • the outer gelatin phase consists of pure gelatin. The color reproduction and the color separation are much better than when these compounds are not added.
  • a photographic color lm comprising a plurality of silver halide emulsions, each of said emulsions being sensitive to a different portion of the spectrum and containing a color coupler capable of coupling with the oxidation product of an aromatic amino color developing agent, and a separate colloid phase containing a reducing agent selected from the group consisting of a compound of the formula BiC-(IJH-Rz its enolic tautomer, and mixtures thereof, wherein an alkyl radical, a carboxy alkylene radical, a lower alkoxy carbonyl radical, and a lower hydroxy alkyl amino carbonyl radical, and
  • X is selected from the group consisting of hydrogen and a lower aliphatic carboxylic acyl radical.
  • a multilayer photographic color iilrn comprising a plurality of superposed silver halide emulsion layers, each of said emulsions being sensitive to a different portion of the spectrum and containing a color coupler capable of coupling with the oxidation product of an aromatic amino color developing agent, and an intermediate colloid layer containing a reducing agent selected from the group consisting of a compound of the formula rality of aqueous colloid silver halide emulsions, each ofl said emulsions being sensitive to a dilerent portion of the spectrum and containing a color coupler capable of coupling with the oxidation product of an aromatic amino color developing agent, as the phase surrounding the discontinuous inner phase a hydrophobic colloid and as the continuous outer phase a gelatin layer containing a reducing agent selected from the group consisting of a cornpound of the formula Rx-CH-Rz o X its enolic tautomer, and mixtures thereof, wherein R1 is a long chain alkyl radical,
  • R2 is selectedfrom the group consisting of hydrogen, an alkyl radical, a carboxy alkylene radical, a lower alkoxy carbonyl radical, and a lower hydroxy alkyl amino carbonyl radical, and
  • X is selected from the group consisting of hydrogen and a lower aliphatic carboxylic acyl radical.
  • a photographic color iilm comprising a colloid layer which contains as the discontinuous inner phase a plurality of aqueous colloid silver halide emulsions, each of said emulsions being sensitive to a dilierent portion of the spectrum and containing a color coupler capable of coupling with the oxidation product of an aromatic amino color developing agent, as the phase surrounding the discontinuous inner phase a hydrophobic colloid containing a reducing agent selected from the group consisting of a compound of the formula Rio-'on-Rz o 0X its enolic tautomer, and mixtures thereof, wherein R1 is a long chain alkyl radical,
  • R2 is selected from the group consisting of hydrogen, an alkyl radical, a carboxy alkylene radical, a lower alkoxy carbonyl radical, andra lower hydroxy alkyl amino carbonyl radical, and
  • X is selectedfrom the group ⁇ consisting of hydrogen and a lower aliphatic carboxylic acyl radical.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US67483A 1959-11-05 1960-11-07 Light sensitive photographic color element Expired - Lifetime US3180734A (en)

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BE2039339 1959-11-05

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GB (1) GB922550A (it)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3447928A (en) * 1965-07-26 1969-06-03 Eastman Kodak Co Silver halide emulsion containing twoequivalent yellow dye-forming coupler
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US3640716A (en) * 1968-05-20 1972-02-08 Fuji Photo Film Co Ltd Method of preventing color mixing in multilayer-type reversal color photographic light-sensitive materials
US3933493A (en) * 1971-07-02 1976-01-20 Mitsubishi Paper Mills, Ltd. Amidrazones as dye components and developer scavengers in diffusion transfer materials and processes
US4042394A (en) * 1973-05-07 1977-08-16 Eastman Kodak Company Photographic dye image stabilization
US4278750A (en) * 1979-09-06 1981-07-14 Eastman Kodak Company Novel electron donor precursors and photographic elements containing them

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE584331A (it) * 1959-11-05

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2336327A (en) * 1941-11-13 1943-12-07 Eastman Kodak Co Preventing color stain in photographic emulsions
US2403721A (en) * 1943-09-23 1946-07-09 Eastman Kodak Co Preventing color fog in photographic material
US2728661A (en) * 1953-10-16 1955-12-27 Eastman Kodak Co Ascorbic acid ester antistain agents
US2937086A (en) * 1955-07-26 1960-05-17 Eastman Kodak Co Multilayer reversal color material
DE1087449B (de) * 1959-11-05 1960-08-18 Gevaert Photo Prod Nv Verfahren zur Verbesserung der Farbwiedergabe in einem farbenphotographischen Material fuer das Farbentwicklungsverfahren

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2336327A (en) * 1941-11-13 1943-12-07 Eastman Kodak Co Preventing color stain in photographic emulsions
US2403721A (en) * 1943-09-23 1946-07-09 Eastman Kodak Co Preventing color fog in photographic material
US2728661A (en) * 1953-10-16 1955-12-27 Eastman Kodak Co Ascorbic acid ester antistain agents
US2937086A (en) * 1955-07-26 1960-05-17 Eastman Kodak Co Multilayer reversal color material
DE1087449B (de) * 1959-11-05 1960-08-18 Gevaert Photo Prod Nv Verfahren zur Verbesserung der Farbwiedergabe in einem farbenphotographischen Material fuer das Farbentwicklungsverfahren

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3447928A (en) * 1965-07-26 1969-06-03 Eastman Kodak Co Silver halide emulsion containing twoequivalent yellow dye-forming coupler
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US3640716A (en) * 1968-05-20 1972-02-08 Fuji Photo Film Co Ltd Method of preventing color mixing in multilayer-type reversal color photographic light-sensitive materials
US3933493A (en) * 1971-07-02 1976-01-20 Mitsubishi Paper Mills, Ltd. Amidrazones as dye components and developer scavengers in diffusion transfer materials and processes
US4042394A (en) * 1973-05-07 1977-08-16 Eastman Kodak Company Photographic dye image stabilization
US4278750A (en) * 1979-09-06 1981-07-14 Eastman Kodak Company Novel electron donor precursors and photographic elements containing them

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DE1087449B (de) 1960-08-18
GB922550A (en) 1963-04-03

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