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
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3924—Heterocyclic
  • G03C7/39268—Heterocyclic the nucleus containing only oxygen as hetero atoms
• • 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
  • G03C7/407—Development processes or agents therefor
  • G03C7/413—Developers

Definitions

• This invention relates to color photography and particularly to a method for preventing the formation of color fog or stain in photographic emulsions.
• color-forming or coupler compounds'combine with the develop ment product of aromatic amino photographic develop- ;ers to produce dyes is well known.
• the color formers or couplers may be added directly to the emulsion layers or may be incorporated in the developing solution as described in Fischer U. S. Patent 1,102,028, granted June 30, 1914, or they may be incorporated in a Water-permeable medium which is insoluble in the carrier for the sensitive silver salt as described in Mannes and Godowsky U. S. Patent 2,304,940, December 15, 1942, and Jelley and Vittum U. S. Patent 2,322,027, granted June 15, 1943.
• a difiiculty frequently encountered in these processes is the formation of color fog or stain.
• dye fog is frequently formed in the emulsion layer. This is because the developing agent has been oxidized to some extent by the action of the air and the oxidized developer tends to couple with the color-forming compound at places in the photographic material where no silver image is produced. It is well known that in these processes the dye should be formed only where the silver halide is reduced to metallic silver, thereby oxidizing the developing agent to a form which couples with the color former. Once the developing agent is oxidized, it couples immediately with the color former whether a photographic image is present or not.
• Aerial oxidation of the developer or oxidation by means of other than the photographic image therefore converts the developer to a form which will immediately react with the color former to produce a color fog or stain.
• This efiect is especially noticeable in materials having couplers incorporated in the sensitive layer since there is no coupler in the developing solution to react with any developing agent which is oxidized by the action of the air. Fog or stain arising from these causes is not readily controlled by the same procedures used to control silver fog.
• a further object is to provide antistain agents which may be dissolved in organic solvents and which are non-difiusing in the colloid of the photographic layer in which they are incorporated.
• a further object is to provide antistain agents which are strong enough reducing agents to react rapidly with oxidized color developer.
• a further object is to provide water-soluble, non-diifusing ascorbic acid esters.
• a further object is to provide antistain agents which do not form highly colored oxidation products when the material containing them is put through an oxidizing bath.
• the sulfonated esters e. g., Compounds 4, 5 and 6, were prepared by heating the ascorbic acid ester, e. g., ascorbyl-6-palmitate, with the appropriate acid anhydride, e. g., o-sulfobenzoic anhydride, fl-sulfopropionic anhydride, or B-sulfostearic anhydride.
• ascorbic acid ester e. g., ascorbyl-6-palmitate
• acid anhydride e. g., o-sulfobenzoic anhydride, fl-sulfopropionic anhydride, or B-sulfostearic anhydride.
• the carboxyl-solubilized esters e. g., Compounds 7 and 8 were prepared by reacting the ascorbic acid ester, e. g., ascorbyl-6-palmitate, with the appropriate acid anhydride, e. g., phthalic anhydride or succinic anhydride, in the presence of a trace of zinc chloride.
• ascorbic acid ester e. g., ascorbyl-6-palmitate
• the appropriate acid anhydride e. g., phthalic anhydride or succinic anhydride
• organic solvent-soluble antistain agents of our invention are useful, in general, with emulsions containing couplers incorporated in the manner described in Mannes and Godowsky U. S. Patent 2,304,940 or Jelley and Vittum U. S. Patent 2,322,027.
• alkali-soluble antistain agents of our invention are useful, in general, with emulsions containing couplers incorporated in the manner described in Fischer U. S. Patent 1,102,028.
• Couplers such as those described in Weissberger U. S. Patent 2,298,443 and Salminen and Weissberger U. S. Patent 2,423,730, when incorporated in emulsions, produce dyes upon color development which are prone to fading by the action of visible or ultraviolet light, when known antistain agents such as 2,5-di-tert. octyl hydroquinone are used in the emulsion layer. These are the yellow and cyan dyes.
• the magenta dyes such as those formed from couplers described in Loria, Weissberger and Vittum U. S. Patent 2,600,788 are relatively little affected by the known antistain agents upon the action of light.
• a quantity of the antistain agent was dissolved with 0.5 g. of coupler in 1.5 cc. of dibutylphthalate.
• the resulting mixture was passed through 'a colloid mill three times, and to the resulting dispersion, 32 cc.
• Two check coatings were made: One containing no antistain agent, and one containing 5 mg. per square foot of 2,5-di-tert. octyl hydroquinone.
• the film strips were exposed on an Eastman I-b Sensitometer using a silver wedge varying in density from 0 Water to 1 liter.
• the antistain agents of our invention may also be used in non-senitive overcoating or filter layers, such as a colloidal silver interlayer of multilayer photographic material.
• the antistain agents of our invention are used in the emulsion or other layer in quantities ranging from 0.07 gram to 4.3 grams per liter of emulsion or gelatin solution. These values are, however, merely illustrative.
• the antistain agents of our invention may be incorporated in a processing solution such as a prebath, first developer bath, or color-forming developer used with color film which is developed with a primary aromatic amino developing agent.
• Our materials are particularly useful with color-forming emulsions coated on paper supports where it is especially important to reduce the minimum or fog densities. This applies both to negative developed paper and to reversal paper as well as to transparency materials.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent an ascorbic acid ester having the formula -OH Lin where X is selected from the class consisting of hydroxyl and -OCOR radicals, R is selected from the class consisting of alkyl radicals, aryl radicals, sulfonated alkyl radicals, sulfonated aryl radicals, carboxylated alkyl radicals and carboxylated aryl radicals, and R is selected from the class consisting of alkyl radicals containing from 7 to 18 carbon atoms, aralkyl radicals containing from 7 to 30 carbon atoms, and mononuclear aryl radicals, and the enediol esters of said compounds.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent an ascorbic acid ester having the formula i l-OH La HOB HsOCOR in which R is an alkyl group containing from 7 to 18 carbon atoms.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent an ascorbic acid ester having the formula:
• R is a sulfonated alkyl group and R is an alkyl group of from 7 to 18 carbon atoms.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent an ascorbic acid ester of an aliphatic acid containing from 7 to 18 carbon atoms.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent 6-1-ascorbyl laurate.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent 6-d-isoascorbyl palmitate.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diifusing coupler compound and as an antistain agent ascorbyl 6-palmitate S-o-sulfobenzoate.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing coupler compound and as an antistain agent ascorbyl 6-palmitate 5-,3-sulfopropionate.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and as an antistain agent ascorbyl 6-palmitate S-fi-sulfostearate.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound and a completely esterified ascorbic acid ester as an anti-stain agent.
• a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing coupler compound and ascorbyl-2,3,5-triacetate-6-palmitate as an anti-stain agent.

Landscapes

• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

Family

ID=23526566

Family Applications (1)

Country Status (4)

Cited By (6)

Families Citing this family (1)

Citations (3)

• 0
  • BE BE532579D patent/BE532579A/xx unknown
• 1953
  • 1953-10-16 US US386672A patent/US2728661A/en not_active Expired - Lifetime
• 1954
  • 1954-10-15 FR FR1112594D patent/FR1112594A/fr not_active Expired
  • 1954-10-18 GB GB29997/54A patent/GB759000A/en not_active Expired

Patent Citations (3)

Also Published As

Similar Documents