Classifications

• • 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
• • 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
  • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
  • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
  • Y10S516/06—Protein or carboxylic compound containing

Definitions

• This invention relates to color photography and particularly to a method for efiiciently incorporating a substantially non-diffusible color coupler into a silver halide emulsion layer and to obtain a stable photographic dye by reacting the incorporated coupled with oxidized color developing agent.
• Colo-r photographic processes in which coloring materials such as couplers are incorporated into a light-sensitive photographic layer are well known. Generally they involve the coupling of a color-forming compound with a primary aromatic amino developing agent to form a colored image.
• the elementary color photographic element (its. the stored unexposed photographic element) comprises a support and a plurality of sensitized silver halide emulsion layers applied thereto; each emulsion layer, in turn, containing many dispersed droplets or particles consisting essentially of a coupler wholly or part- 1y dissolved in a high boiling water-insoluble coupler solvent or possibly encapsulated in a polymeric or wax-like material (French Pats. 2,017,718, 1,555,663 and U.S. Pat. 2,772,163).
• liquid high-boiling coupler solvent of the formula wherein R is individually defined at each occurrence as an alkyl group having 3-15 carbon atoms, including straight or branched chain alkyl groups and preferably having 5-8 carbon atoms; and n is individually defined at each occurrence as 0-4 and preferably 1-4.
• Hydrophobic liquid coupler solvents within the above class include the esters of a 1,4-dihydric cyclohexanol, a 1,3-dihydric cyclohexanol and the corresponding 1,3- and 1,4-hydroxy-lower alkylene derivatives exemplified in the following formulae R"o0-0--((3H,).u
• R and R" are individually defined at each occurrence as an alkyl group as defined in Formula I above and n and m are individually defined as 0-2, preferably as l-2.
• Permanent Coupler Solven is defined as a liquid cyclohexanecontaining ester of the type defined in Formulae I-III above which is retained in the coupler solvent droplets dispersed within the silver halide emulsion layer of the color photographic element.
• Low-Boiling Auxiliary Solvent as used herein is intended to define low-boiling organic solvents having a water miscibility not exceeding about 6.5 parts/ parts of water and a boiling point range of about 76-205 C. Suitable auxiliary solvents of this type are listed, for instance, in Julian U.S. Patent 2,949,360.
• Permanent coupler solvents within the present invention are more specifically described in the following table relative to Formulae II and HI.
• Another useful synthesis involves reacting 1,4 or 1,3 cyclohexane dialkanol with an excess of an alkanoic acid of from 6-13 carbon atoms in the presence of a platinum or zinc catalyst. The resulting product is then stripped under reduced pressure, neutralized with dilute sodium hydroxide solution, filtered, decanted, and the neutralized product dried and molecularly distilled to obtain the desired ester product.
• Ballasted non-difiusible cyan dye-forming couplers suitable for use in the present invention are exemplified or suggested in U.S. Pats. 2,373,293; 2,423,730; 2,801,171; 2,895,826; 2,908,573; 3,046,129; 3,516,831; 3,311,476; 3,253,294; 3,458,315; 3,227,550; 3,476,563; 3,458,315; 3,419,390 and 3,034,892.
• DIR Development-Inhibitor-Releasing
• An effective amount for non-ditfusible couplers of the above type can range from about 5-200 mg./ft. per emulsion layer of coated material, a concentration of 10-50 mg./ft. being generally satisfactory.
• DIR coupler is utilized in addition to 2- and/or 4-equivalent dye-forming couplers, it is found that about 5-30 mole percent of the former (i.e. DIR coupler) is adequate.
• Color photographic elements within the scope of the present invention are preferably multilayered and usefully contain one or more of the following components:
• Typical supports include cellulose acetate film, polystyrene film, polyethylene film, polypropylene film, polylethylene terephthalate film, etc.
• Typical suitable silver halide emulsions include silver chloride, silver bromide, silver chlorobromide, silver bromoiodide, silver chlorobromoiodide, and silver chloroiodide emulsions.
• gelatin spacer layers can also be included between the light-sensitive emulsion layers and also a Carey-Lea filter layer; spacer layers of this type can optionally contain removable additives to further improve dye stability and improve color separation and
• D An ordinary protective gelatin overcoat layer.
• a light-sensitive gelatino silver halide emulsion is prepared by dissolving 20 grams of 2-[u-(2,4-di-tert amylphenoxy)-acetamido]-4,6-dichloro 5 methylphenol (ref. US. Pat. 2,423,730) in 10 grams of di-n-butylphthalate in the presence of 30 ml. isopropylacetate as an auxiliary solvent. The resulting solution is poured into a mixture of 181 gm. of a 10% aqueous gelatin solution in the presence of an alkyl naphthylene sulfonate sodium salt as surfactant. The mixture is emulsified in a colloid The cyan image (neutral density 1.5) is then tested for.
• Example IA is repeated using quinitol di(2-ethyl hexoate (Permanent Solvent No. 5) as the high-boiling coupler solvent.
• the loss in density of the cyan record is reported in Table III as test strip T-2.
• This film is exposed on an Eastman Model 1B sensitometer processed in the usual manner and tested for cyan dye stability at 77 C. (40% Relative Humidity) for 1 week and the density loss to red light is determined for a neutral image having a density of 1.5.
• a method for incorporating a photographic colorforming coupler in a hydrophilic colloid which comprises dissolving said coupler in an organic solvent and dispersing the resulting solution in said colloid; the improvement which comprises using as said organic solvent a solvent system containing a liquid ester of the formula wherein R is individually defined at each occurrence as an alkyl group having 3-15 carbon atoms; and n is individually defined at each occurrence as 0-4.
• coupler is a phenolicor wnaphtholic-cyan dye-forming coupler compound.
• a method for incorporating a member selected from the group consisting of a phenolic cyan dye-forming coupler compound into a hydrophilic colloid which comprises dissolving said coupler in an organic solvent and dispersing the resulting solution in said colloid, the improvement which comprises using as said organic solvent a solvent system containing (1) a liquid ester of the formulae wherein R' and R" are individually defined at each occurrence as an alkyl group of 5-8 carbon atoms; and n and m are individually defined as 0-2; and (2) a lowboiling auxiliary solvent.
• R and R" are branched alkyl groups of 5-8 carbon atoms and n and m are defined as 0-1.
• a method for incorporating a photographic colorforming coupler in a hydrophilic colloid which comprises dissolving said coupler in an organic solvent and dispersing the resulting solution in said colloid; the improvement which comprises initially dissolving a phenolic cyan dyeforming coupler in a solvent system containing 1,4-cyclohexyl di rnethylene-bis(Z-ethylhexanoate) and a low-boiling auxiliary solvent having minimal miscibility in water.
• a light-sensitive photographic silver halide emulsion containing finely divided particles comprising a member selected from the group consisting of a 5pyrazolone magenta dye-forming coupler, and a l-H-pyrazolo [3,2- c]s-triazole magenta dye-forming coupler compound, together with a liquid coupler solvent of the formulae (CH2)mOCOR" wherein R and R' are individually defined at each occurrence as an alkyl group of 5-8 carbon atoms; and n and m are individually defined as 1-2.
• a light-sensitive photographic silver halide emulsion containing finely divided particles comprising a member selected from the group consisting of an acetoacetanilide yellow dye-forming coupler and a benzoylacetanilide yellow dye-forming coupler compound; together with a liquid coupler solvent of the formulae (CH2)mOCO-R" wherein R and R are individually defined at each occurrence as an alkyl group of 58 carbon atoms; and n and m are individually defined as l-2.
• R are branched alkyl groups of 5-8 carbon atoms and n and m are defined as l.
• Coupler is a S-pyrazolone magenta dye-forming coupler; R and R are branched alkyl groups of 58 carbon atoms; and n and m are defined as l.
• the coupler is an acetoacetanilide yellow dye-forming coupler in which the non-0x0 carbon atom of the aceto group is a tertiary carbon atom; R and R are branched alkyl groups of 58 carbon atoms; and n and m are defined as 1.
• liquid substantially water-immiscible ester is 1,4-cyclohexyl diethylenebis(2-ethylhexanoate).
• liquid substantially water-immiscible ester is 1,4-cyclohexy1 diethylene-bis (Z-methylhexanoate) 20.
• liquid substantially water-immiscible ester is 1,4-cyclohexyl dimethylene-bis Z-ethylhexanoate) 21.
• liquid substantially water-immiscible ester is 1,4-cyclohexyl dimethylene-bis (Z-methylhexanoate 22.
• a color photographic element comprising a support layer and at least one light-sensitive silver halide emulsion layer having finely divided particles incorporated therein containing at least one color photographic dye producing coupler compound together with a coupler solvent of the formula wherein R is individually defined at each occurrence as an alkyl group having 3-15 carbon atoms; and n is individually defined at each occurrence as 0-4.
• a color photographic element comprising a support layer and at least one light-sensitive silver halide emulsion layer having finely divided particles incorporated therein containing at least one color photographic coupler compound and a liquid coupler solvent of the formulae wherein R and :R' are individually defined at each occurrence as an alkyl group of 58 carbon atoms; and n and m are individually defined as 1-2.
• a color photographic element of claim 26 wherein the coupler compound is a phenolic cyan dye-forming coupler compound or an a-naphtholic cyan dye-forming coupler compound.
• a color photographic element of claim 26 wherein the coupler compound is a 5-pyrazolone magenta dyeforming coupler or a 1 H pyrazolo [3,2-c1-s-triazole magenta dye-forming coupler compound.
• a color photographic element of claim 26 wherein the coupler compound is an acetoacetanilideor a benzoylacetanilide-yellow dye-forming coupler compound.
• a color photographic element of claim 26 wherein the coupler is an acetoacetanilide yellow dye-forming coupler in which the non-0x0 carbon atom of the aceto group is a tertiary carbon atom; R and R" are individually defined as branched alkyl groups of 5-8 carbon atoms; and n and m are defined as l.
• a color photographic element of claim 23 wherein the liquid substantially water-immiscible ester is 1,4-cyclohexyldiethylene-bis- (Z-ethylhexanoate) 34.
• a color photographic element of claim 23 wherein the liquid substantially water-immiscible ester is 1,4-cyclohexyldiethylene-bis- (Z-methylhexano ate) l0 35.
• a color photographic element of claim 23 wherein the liquid substantially water-immiscible ester is 1,4-cyclohexylene dimethyl-bis-(Z-ethylhexanoate) 36.
• the liquid substantially water-immiscible ester is 1,4-cyclohexyldimethylene-bis (Z-methylhexanoate)

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Publications (1)

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Family Applications (1)

Country Status (6)

Cited By (9)

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• 1972
  • 1972-05-25 US US00256658A patent/US3748141A/en not_active Expired - Lifetime
• 1973
  • 1973-04-16 CA CA168,821A patent/CA1006031A/en not_active Expired
  • 1973-05-24 GB GB2484173A patent/GB1422986A/en not_active Expired
  • 1973-05-25 BE BE131563A patent/BE800080A/xx not_active IP Right Cessation
  • 1973-05-25 FR FR7319029A patent/FR2185811B1/fr not_active Expired
  • 1973-05-25 JP JP5785773A patent/JPS561616B2/ja not_active Expired

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