US2801171A - Photographic color former dispersions - Google Patents

Photographic color former dispersions Download PDF

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Publication number
US2801171A
US2801171A US476561A US47656154A US2801171A US 2801171 A US2801171 A US 2801171A US 476561 A US476561 A US 476561A US 47656154 A US47656154 A US 47656154A US 2801171 A US2801171 A US 2801171A
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Prior art keywords
water
solvent
solution
color
coupler
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US476561A
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Scheuring S Fierke
Chechak Jonas John
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE543745D priority Critical patent/BE543745A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US476561A priority patent/US2801171A/en
Priority to GB31990/55A priority patent/GB791219A/en
Priority to DEE11699A priority patent/DE1003586B/de
Priority to FR1148474D priority patent/FR1148474A/fr
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Publication of US2801171A publication Critical patent/US2801171A/en
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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

Definitions

  • This invention relates to color photography and particularly to a method for incorporating couplers in silver halide emulsion layers.
  • low ratio coupler dispersions may be prepared by (I) dissolving the coupler in a solvent including a low boiling substantially water-insoluble organic solvent, or an appreciably water-soluble organic solvent, for the coupler, and less than about one part per part of coupler of a substantially water-insoluble low molecular weight organic crystalloidal solvent for the coupler, the crystalloidal solvent having a boiling point above about 175 C.
  • a mixing tank 1 provided with a suitable stirring device 2 may be used to produce the solution of the coupler in the solvent or mixture of solvents.
  • the low-boiling water-insoluble solvent or the water-soluble solvent or both is added through pipe 3 to dissolve the coupler, and the crystalloidal high-boiling solvent may also be added to the tank, if employed.
  • the solution is passed to a second tank 4 where gelatin solution is added, and the solution then homogenized in a colloid mill 5 and passed to the gel plate 6 where it is chilled and set by means of cooling coils 7.
  • the chilled dispersion is then noodled and either air dried directly as shown at 8 or first washed with water from a spray nozzle 9 as shown at 10 and then air dried as shown at 8.
  • the water washing step is required only if the coupler dispersion was made using a water-soluble solvent or mixture of water-soluble and water-insoluble solvents. If only the low-boiling water-insoluble solvent was used, the water washing step is not required and the dispersion can be directly air dried as shown at 8.
  • the dry dispersion is then mixed with a silver halide emulsion in tank 10 to form the final gelatino-silver halide emulsion containing the coupler dispersion.
  • Couplers which may be used according to our invention are those disclosed in Ielley and Vittum U. S. Patent 2,322,027 and the following:
  • the mixture was heated for 1 hours on the steam bath with continuous stirring. At no time was solution complete.
  • the mixture was cooled externally to 10 C. and to it was added 1 l. of ice water.
  • the mixture was made acid to Congo paper by the introduction of 15 cc. of concentrated hydrochloric acid. A few seeds of prod uct from a previous preparation were added and stirring continued for one hour.
  • the product separated as a white cheese-like ball.
  • the acidic aqueous liquor was decanted and replaced by 1200 cc. of petroleum ether in which the product dissolved readily.
  • the petroleum ether solution was washed successively with 500 cc. of water containing 25 cc. of concentrated hydrochloric acid, 500 cc. of water, 500 cc. of 2% sodium bicarbonate solution, 500 cc. of water.
  • the product was dissolved in 2 l. of petroleum ether by warming slightly. To the water-white solution was added 5 g. of Darco (activated carbon) and the mixture was filtered by suction through a layer of 5 g. of Darco on a Buchner funnel. The colorless filtrate was concentrated to a volume of 200 cc. and the product crystallized. The mixture was stirred smooth, cooled externally to 0 C. and filtered. The produce was washed on the funnel with 100 cc. of cold petroleum ether (0 C.). The solid was dried at 50 C. Yield: 53 g. (37%), M. P. 123124 C.
  • a-Diamylphenoxy-n-butyric acid In a 3-liter three-necked flask, equipped with a stirrer, thermometer and reflux condenser was placed 40 cc. of water and 660 cc. of denatured alcohol. In the alcohol was dissolved 80 g. (2.0 mole) of caustic soda pellets by stirring and heating at a boil. Stirring was maintained throughout the preparation. To this hot solution was added 234 g. (1.0 mole) of redistilled di-tert-amyl phenol and refluxing was continued for 5 minutes. The solution was cooled externally to 60 C. and 167 g. (1.0 mole) of a-bromo-n-butyric acid was added. The temperature of the solution rose 15 C. The solution was heated to a boil and boiling under the reflux was maintained for 3 hours. Some separation of salt occurred.
  • the mixture was cooled externally to room temperature and diluted with 1 liter of ice water and 200 cc. of concentrated hydrochloric acid. The resulting mixture showed a strong acidity on Congo paper.
  • the oily product was extracted with 500 cc. of ethyl ether (tech.) and the ether extract was washed with 500 cc. of water.
  • the ether solution was separated and transferred to a suitable Claisen flask.
  • the moist ether extract was concentrated by distillation, final traces of ether and water being removed by suction.
  • the syrupy residue was distilled in vacuo, an oil bath being used until all traces of diamyl phenol had been recovered. In the distillation a fore-run of about 15 g. was collected up to /1 mm. The diamyl phenol was collected at 11l-l69/1 mm., g. of it being recovered. Nearly all of the diamyl phenol boils at 123-l25/l mm. The oil bath was removed and the a-diamylphenoxy-n-butyric acid was distilled over a flame. The product was collected at l70-200/l mm. This product can be recognized by the sudden increase in the viscosity of the distillate. No appreciable residue was left in the still. Yield: 125 g. (39%).
  • a-Diamylphenoxy-n-butyry! chloride In a 500 cc. Claisen fiask was placed 160 g. (0.5 mole) of a-diamyl phenoXy-n-butyric acid and 160 g. (1.35 mole) of thionyl chloride (distilled over quinoline). On being warmed to 40 C. a gentle evolution of sulfur dioxide and hydrogen chloride commenced in the clear amber liquid. The temperature was held at 40-45" C. until the evolution of gas had ceased. This generally occurred after three hours.
  • p-Nitrophenoxyacetyl chloride In a 500-ml. flask were mixed 19.7 g. (0.1 mole) of p-nitrophenoxyacetic acid and 100 ml. of thionyl chloride. The mixture was refluxed for 5 hours on a steam bath and the excess thionyl chloride removed under reduced pressure. The removal of the thionyl chloride was continued until the residue had reached constant weight. The acid chloride was used without purification and gave good results. It may be crystallized from dried ligroin to obtain a white crystalline material melting at 86-87 C.
  • the mixture was refluxed with stirring for a total of onehalf hour, during which time the nitro compound dissolved and the froth over the refluxing solution became colorless.
  • the solution was filtered and the filtrate was drowned in 2 liters of water.
  • the amine which separated as a fine white solid was filtered and washed on the funnel with 2 x 250 cc. of 10% acetic acid and 8 x 250 cc. of water and dried at approximately 50 to constant weight.
  • the yield of product was 50 g. (93%).
  • the melting point was 205-6 (recrystallized amine melts at 216-18).
  • 2,4-di-tert.-amylphenoxy acetic acid then cooled to 60 and 94.5 g. (1.0 mole) of chloroacetic acid added.
  • the mixture was refluxed with stirring for three hours, cooled to room temperature, diluted with 1 liter of ice water and acidified with 200 cc. of cone. hydrochloric acid.
  • the diamylphenoxy acetic acid separated as an orange-brown oil, was extracted with 200 cc. of ether and the wet ether layer concentrated under reduced pressure on the steam-bath.
  • the heavy oil was vacuum distilled, collecting at 172-l76 at 1 mm./Hg. Yield: 127 g. (43%).
  • the viscous oil soon solidified to a wax-like solid.
  • the diamylphenoxy acetic acid can be purified by recrystalliaztion from hexane, M. P. l l6-117; snow-white powder.
  • the diazotization was run at a temperature not exceeding 5.
  • the diazonium solution was diluted with 500 cc. of denatured alcohol, treated with decolorizing carbon, and filtered.
  • a-Benzoyl-hamino-Z-methoxyacetanilide hydrochloride In a one-liter 3-necked flask equipped with a reflux condenser were placed 31.4 g. (0.1 mole) of a-benzoyl-2- methoxy-4-nitroacetanilide, 200 ml. of 50% aqueous denatured alcohol, and ml. of glacial acetic acid. The mixture was brought to a boil, the heat was removed, and 31.4 g. of iron powder was added as rapidly as possible. When the initial reaction had subsided, heat was again applied and the reaction mixture was refluxed 20 minutes. After filtration the filtrate was diluted as rapidly as possible with one liter of water and 300 ml.
  • High boiling organic crystalloidal coupler solvents which may be used according to our invention include (1) alkyl esters of phthalic acid in which the alkyl radical preferably contains less than 6 carbon atoms, e. g., methyl phthalate, ethyl phthalate, propyl phthalate, n-butyl phthalate, di-n-butyl phthalate, n-arnyl phthalate, isoamyl phthalate and dioctyl phthalate, (2) esters of phosphoric acid, e. g., triphenyl phosphate, tricresyl phosphate and diphenyl mono-p-tert. butyl phenyl phosphate, and (3) alkyl amides or acetanilide, e. g., N,n-butylacetanilide and N-methyl-p-methyl acetanilide.
  • Low boiling water-insoluble organic solvents in which the coupler is first dissolved and which are removed to form the substantially dry dispersion of coupler in gelatin include methyl, ethyl, propyl and butyl acetates, isopropyl acetate, ethyl propionate, sec. butyl alcohol, carbon tetrachloride and chloroform, which are volatile solvents and can be removed by air drying.
  • Water-soluble organic solvents include methyl isobutyl ketone, ,B-ethoxy ethyl acetate, fi-butoxy fi-ethoxy ethyl acetate, tetrahydrofurfuryl adipate, Carbitol acetate (diethylene glycol monoacetate), methoxy triglycol acetate, methyl Cellosolve acetate, acetonyl acetone, diacetone alcohol, butyl Carbitol, butyl Cellosolve, methyl Carbitol, methyl Cellosolve, ethylene glycol diethylene glycol and dipropylene glycol. Certain of these water-soluble solvents, e. g., Carbitol acetate, butyl Cellosolve, have high flash points, and therefore reduce the fire hazard during removal from the emulsion. The water-soluble solvents are removed from the emulsion by washing with water.
  • the coupler is dissolved in a solvent or solvent mixture of such composition that the ratio of coupler to high boiling organic solvent will be one part of coupler to less than one part of high boiling solvent.
  • the solvent will always contain low boiling organic solvent, which is removed during preparation of the emulsion coating, and may contain high boiling organic solvent in the proper ratio, or may be entirely free of high boiling solvent, in which case a solventfree" coupler dispersion is obtained in the final coating. It is usually desirable, however, to have some high boiling organic solvent in the final coating.
  • a suitable ratio of coupler to high boiling organic solvent would be 8 grams of coupler to 4 cc. of high boiling solvent, or a ratio of 19/2.
  • the solvent mixture preferably contains ethyl acetate as the low boiling solvent and di-n-butyl phthalate as the high boiling solvent, although other mixtures and ratios varying within the scope expressed above may obviously be employed.
  • Alkanol B sodium triisopropylnaphthalene sulfonate
  • the dispersion was set up on a chill plate at 40 F., noodled and air dried at 78 C. and 50% relative humidity. Total dry weight of the dispersion was 18.5 grams and it falls persed in gelatin into particles of less than 0.5 mg with no apparent crystals.
  • EXAMPLE 2 100 grams of the coupler used in Example 1 was dissolved in 250 cc. of ethyl acetate at a reflux temperature of ethyl acetate. This solution was poured into a solution containing 800 cc. of gelatin solution and 100 cc. of 5% Alkanol B solution and then milled 5 times in a colloid mill. 50 cc. of water was used to rinse the mill. The dispersion was set up on a chilled plate at 40 F., noodled and air dried at 78 C. and 50% relative humidity. Total weight of the dispersion was 193 grams.
  • EXAMPLE 3 Eight grams of the coupler used in Examples 1 and 2 grams of dioctyl hydroquinone were dissolved in 25 cc. of ethyl acetate at the reflux temperature of ethyl acetate. This solution was poured into a solution containing 136 cc. of 10% gelatin solution and 16 cc. of 5% Alkanol B solution and was then milled 5 times in a colloid mill. Fifty cc. of water was used to rinse the mill.
  • antistain agents such as 2,5-diisooctyl hydroquinone and 2,5-di-n-octyl hydroquinone, and ultra-violet light absorbers such as 5-o-sulfobenzal-3- pheuyl-Z-phcnylimino-4-thiazolidone, may be dispersed in gelatin by our method.
  • a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic dcvelopment, in a solvent including at least a solvent selected from the class consisting of water-soluble organic solvents for the color-forming compound having a solubility of at least 2 parts of solvent in 100 parts of water and a boiling point above about 125 C., and low-boiling water-insoluble organic solvents for the color-forming compound having a boiling point below about 125 C.
  • the method of incorporating a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including at least a low-boiling water-insoluble organic solvent for the colorforming compound having a boiling point below about 125 C. and a solubility of from .08 to 33 parts of solvent in parts of water, and less than about one part per part of color-forming compound of a substantially water-insoluble, low molecular weight, organic crystalloidal solvent for the color-forming compound, said crystalloidal solvent having a boiling point above about 175 C.
  • the method of incorporating a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including a water-soluble organic solvent for the color-forming compound having a solubility of at least 2 parts of solvent in 100 parts of water and a boiling point above about C., and less than about one part per part of color-forming compound of a substantially water-insoluble, low molecular weight, organic crystalloidal solvent for the color-forming compound, said crystalloidal solvent having a boiling point above about C.
  • the method of incorporating a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including at least ethyl acetate and less than about one part per part of colorforming compound of an alkyl ester of phthalic acid in which the alkyl group contains less than 6 carbon atoms, dispersing the solution in aqueous gelatin, chilling and setting the gelatin dispersion, removing at least 90% of the water and substantially all of said ethyl acetate from the dispersion to form a dry dispersion and mixing the dry color-former dispersion with a gelatino-silver halide emulsion.
  • the method of incorporating a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including at least ethyl acetate and less than about one part per part of colorforming compound of di-n-butyl phthalate, dispersing the solution in aqueous gelatin, chilling and setting the gelatin dispersion, removing at least 90% of the water and substantially all of said ethyl acetate from the dispersion to form a dry dispersion and mixing the dry color-former dispersion with a gelatino-silver halide emulsion.
  • the method of incorporating a color former in a. gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including at least ethyl acetate and less than about one part per part of colorforming compound of di-n-butyl phthalate, dispersing the solution in aqueous gelatin, chilling and setting the gelatin dispersion, removing at least 90% of the water and substantially all of said ethyl acetate from the dispersion by air drying to form a dry dispersion and mixing the dry color-former dispersion with a gelatinosilver halide emulsion.
  • the method of incorporating a color former in a gelatino-silver halide emulsion which comprises dissolving a color-forming compound capable of reacting with a primary aromatic amino developing agent on photographic development, in a solvent including about three parts of ethyl acetate and about one-half part ppr part of color-forming compound of di-n-butyl phthalate, dispersing the solution in aqueous gelatin, chilling and setting the gelatin dispersion, removing at least of the water and substantially all of said ethyl acetate from the dispersion by air drying to form a dry dispersion and mixing the dry color-former dispersion with a gelatinosilver halide emulsion.

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  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US476561A 1954-12-20 1954-12-20 Photographic color former dispersions Expired - Lifetime US2801171A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE543745D BE543745A (fr) 1954-12-20
US476561A US2801171A (en) 1954-12-20 1954-12-20 Photographic color former dispersions
GB31990/55A GB791219A (en) 1954-12-20 1955-11-09 Method of making dispersions of colour couplers for use in light-sensitive silver salt emulsions
DEE11699A DE1003586B (de) 1954-12-20 1955-12-17 Verfahren zum Einlagern von Bestandteilen in Gelatine-Halogensilber-Emulsionen, insbesondere fuer farbenphotographische Zwecke, wie Farbbildnern
FR1148474D FR1148474A (fr) 1954-12-20 1955-12-19 Procédé pour l'incorporation de coupleurs chromogènes aux émulsions photographiques

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GB (1) GB791219A (fr)

Cited By (63)

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US3660101A (en) * 1965-06-21 1972-05-02 Eastman Kodak Co Photographic materials and processes
US3816121A (en) * 1971-09-04 1974-06-11 Fuji Photo Film Co Ltd Direct positive photographic material containing a color coupler under one micron in size and fogged silver halide grains with substantially no internal sensitivity having absorbed on the surface a desensitizing dye containing a solubilizing group
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EP0228914A2 (fr) 1985-12-28 1987-07-15 Konica Corporation Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière
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US4885234A (en) * 1988-09-29 1989-12-05 Eastman Kodak Company Photographic materials containing stable cyan coupler formulations
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EP0435334A2 (fr) 1989-12-29 1991-07-03 Fuji Photo Film Co., Ltd. Produit photographique couleur à l'halogénure d'argent contenant un coupleur cyan coloré en jaune
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EP0452984A1 (fr) 1985-09-25 1991-10-23 Fuji Photo Film Co., Ltd. Procédé de traitement d'un matériau photographique à l'halogénure d'argent pour un emploi photographique
EP0452886A2 (fr) 1990-04-17 1991-10-23 Fuji Photo Film Co., Ltd. Méthode de traitement d'un produit photographique couleur à l'halogénure d'argent
EP0476327A1 (fr) 1990-08-20 1992-03-25 Fuji Photo Film Co., Ltd. Produit de pellicule photographique retenant des informations et procédé de production d'épreuve en couleurs
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Also Published As

Publication number Publication date
BE543745A (fr)
DE1003586B (de) 1957-02-28
FR1148474A (fr) 1957-12-10
GB791219A (en) 1958-02-26

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