US3700453A - Antistain agents comprising mixtures of secondary-alkylhydroquinones - Google Patents

Antistain agents comprising mixtures of secondary-alkylhydroquinones Download PDF

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US3700453A
US3700453A US17330A US3700453DA US3700453A US 3700453 A US3700453 A US 3700453A US 17330 A US17330 A US 17330A US 3700453D A US3700453D A US 3700453DA US 3700453 A US3700453 A US 3700453A
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antistain
agent
color
mixture
hydroquinone
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William F Knechel
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor

Definitions

  • color forming or coupler compounds combine with the development product of aromatic amino photographic developers to produce dyes.
  • 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. Pat. 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 US. Pat. 2,304,940, Dec. 15, 1942, and Jelley and Vittum US. Pat. 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.
  • the developing agent couples immediately with the color former whether a photographic image is present or not.
  • Aerial oxidation of the developer or oxidation by means 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 elfect is especially noticeable in materials halving couplers incorporated in the sensitive layers 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.
  • hydroquinone or certain of its derivations is well known in the prior are for the control of color fog or stain.
  • alkyl and di-alkyl hydroquinones available in the prior art have certain disadvantages however. Many are difiicult to synthesize requiring two to four steps; others have low molecular weights which allow them to wander between layers in a multilayer color photographic material, thereby causing undesirable side efliects; still others crystallize out during or after coating to give poor coating quality; and also some of the alkyl hydroquinones can be shown to undergo an oxidation reaction during coating operations, or during processing to give colored byproducts.
  • Another object of my invention is to provide novel liquid antioxidants which are advantageously incorporated as dispersions in aqueous hydrophilic colloid coating compositions without the use of a solvent.
  • a further object is to provide novel antistain agents which are not oxidized to colored by-products in aqueous hydrophilic colloid coating compositions before, during coating, or during processing.
  • Another object is to provide novel photographic ele ments containing at least one hydrophilic colloid layer containing a dispersion of our antistain agents.
  • my antistain agents which are mixtures of at least two secondary-alkylhydroquinones in which the secondary alkyl substit-uents have from 9 to 20 carbon atoms
  • the preparation of dispersions of my antistain agents in hydrophilic colloids and the use in multilayer multicolor photographic elements of coatings of hydrophilic colloid containing dispersions of my antistain agents.
  • My antistain agents are mixtures of at least two secondary-alkylhydroquinones which are monosubstituted and/or disubstituted hydroquinones in which the secondary-alkyl groups have from 9 to 20 carbon atoms, such as, a secondary nonyl group (e.g., l-methyloctyl, l-ethylheptyl, l-propylhexyl, l-butylamyl, etc.), a secondary decyl group (e.g., l-methylnonyl, l-ethyloctyl, l-propylheptyl, l-butylhexyl, etc.), a secondary-undecyl group (e.g., l-methyldecyl, l-ethylnonyl, l-propyloctyl, l-butylheptyl, l-pentylhexyl, etc.)
  • a secondaryoctadecyl group e.g., l-methylheptadecyl, l-ethylhexadecyl, l-propylpentadecyl, l-butyltetradecyl, l-amyltridecyl, l-hexyldodecyl, l-heptylundecyl, l-octyldecyl, etc.), a secondary-nonadecyl group (e.g., l-methylhexadecyl, l-ethylhexadecyl, l-propylpentadecyl, l-butyltetradecyl, l-amyltridecyl, l-hexyldodecyl, l-heptylundecyl, l-octyldecyl, etc.),
  • mixtures containing two different secondary-alkylhydroquinones usually there is in the range from 1% to 99% of one compound and in the range from 99% to 1% of the second compound.
  • a preferred range is from to 95% of one compound and from 95% to 5% of the second compound.
  • a large variety of mixtures of secondary-alkylhydroquinones are used to advantage according to my invention.
  • mixtures of 2-secondary-alkylhydroquinones in which the compounds differ in the number and/or arrangement (position isomers) of carbon atoms in the alkyl group are used to advantage
  • mixtures of 2,5-di-secondaryalkylhydroquinones in which the compounds differ in the number and/or arrangement of carbon atoms in the alkyl group on one or both, i.e., 2- and 5-position substituents are used to advantage
  • mixtures of (1) and (2) are used to advantage.
  • Preferred mixtures of my invention are mixtures of isomers of a 2-secondary-alkylhydroquinone, mixtures of isomers of a 2,5-di-secondary-alkylhydroquinone or mixtures of a 2-secondary-alkylhydroquinone (a single compound or mixture of two or more isomers) and a 2,S-di-secondary-alkylhydroquinone (a single compound or mixture of two or more isomers).
  • Such mixtures of isomers are advantageously made by reacting hydroquinone with the appropriate primary olefin(s) containing from 9 to carbon atoms in the presence of a Lewis Acid at elevated temperatures over an extended period of time so that isomeric forms of the primary olefin are formed and react with hydroquinone to produce at least one isomeric compound of the monosubstituted secondary-alkylhydroquinone and at least one isomeric compound of the disubstituted secondary-alkylhydroqninone compound in a single reaction step.
  • Lewis Acids are protons and sources of protons, such as acids, metal atoms which are able to form coordination systems with water or ammonia, sulfur from sulfur dioxide, sulfuric acid, sodium bisulfite, atoms and free radicals with incomplete electron shells, etc.
  • Lewis Acids are sulfuric acid, phosphoric acid, hydrochloric acid, sodium bisulfate, monosodium phosphate, zinc chloride, aluminum chloride, boron trifiuoride, benzene sulfonic acid, silica-alumina, Amberlite IR-12O (Rohm and Haas Co. trade name for an acidic ion exchange resin), etc. It is advantageous to heat a solvent solution of hydroquinone together with the Lewis Acid to distill any moisture from the mixture as an azcotrope and then add the primary olefin or primary olefins while raising the temperature of the reaction mixture to a temperature in the range of from about 130 C. to about 240 C. over an extended period of time.
  • the rate at which the olefin is added to the reaction mixture, the rate of heating and the reaction time are selected so as to produce the desired mixture of isomers in the final product.
  • the most advantageous reaction conditions will depend upon the particular mixture of isomers desired and are readily determined.
  • the reaction mixture is cooled, added to a suitable organic solvent such as ligroine; the Lewis Acid is removed by filtration or other appropriate means; the unreacted olefin is removed by distillation at reduced pressure and then the mixture of my secondaryalkylhydroquinones is distilled off at reduced pressure or separated from the residual reaction mixture by other appropriate means.
  • the hot mixture of my compounds is advantageously protected from air oxidation whenever possible during this procedure by keeping it under a nitrogen atmosphere.
  • one or more isomers are advantageously included of either or both the monoor di-substituted secondary-alkylhydroquinone.
  • Mixtures like Mixture 10 can have as many as seven isomers of the monosubstituted secondary-alkylhydroquinone and as many as27 isomers of the disubstituted secondaryalkylhydroquinone.
  • Mixtures like Mixture 12 for example, can have as many as nine isomers of the monosubstituted secondary-alkylhydroquinone and forty-five isomers of the disubstituted secondary-alkylhydroquinone.
  • My mixtures are eutectic mixtures (or nearly eutectic mixtures) in which the components produce minimum eutectic points, preferably below room temperature.
  • My mixtures of secondary-alkylhydroquinones are advantageously dispersed in any of the well-known photographic hydrophilic colloids, including gelatin, albumen, collodion, gum arabic, agar-agar, cellulose derivatives, e.g., alkyl esters of carboxylated cellulose, hydroxyethyl cellulose, synthetic resins, e.g., the amphoteric copolymers described by Claver et al. in US. Pat.
  • polyvinyl alcohol polyvinyl pyrrolidone, copolymers of an alkyl acrylate, an alkylcarbonylacetoxyalkylacrylate and either a sulfoalkylacrylate or acrylic acid, e.g., are described by Smith in US. Pat. 3,488,708, issued Jan. 6, 1970, particularly from line 28 in column 5 to line 8 in column 6, and others well known in the art.
  • My mixtures that are liquid at room temperature are readily dispersed without the need of a solvent.
  • My mixtures that are not liquid at room temperature are advantageously dispersed as a solution in (1) a high-boiling organic crystalloidal solvent, such as alkyl esters of phthalic acid, e.g., methyl phthalate, ethyl phthalate, prdpyl phthalate, n-butyl phthalate, di-n-butyl phthalate, n-amyl phthalate, isoamyl phthalate and dioctyl phthalate, and esters of phosphoric acid, e.g., triphenyl phosphate, tricresyl phosphate, diphenyl mono-p-tert, butyl phenyl phosphate or (2) lowboiling organic solvents, such as, lower alkyl acetates, ethyl propionate, sec.-butyl alcohol, methyl isobutyl ketone, ,B-ethoxyethyl acetate, methyl Cellosolv
  • Dispersions in hydrophilic colloids of my antistain agents( my mixtures) are characterized by not crystallizing when held at temperatures below room temperature before, during and after coating as a layer in a multilayer photographic element. This represents a valuable technical advance over the prior art antistain agents which do crystallize from dispersions in hydrophilic colloids while being held below room temperature prior to coating.
  • Dispersions of my antistain agents are further characterized by not producing discolorations that certain prior art antistain agents produce.
  • Dispersions of my antistain agents in hydrophilic colloids are advantageously coated in any of the layers of any of the multilayer multicolor photographic elements where antistain agents are used. For example, they are advantageously added to one or more of the light-sensitive layers and/ or in nonlight-sensitive layers coated over or between the light-sensitive layers. They are used in photographic elements that contain incorporated colorforming couplers in the light-sensitive emulsion layers or in multilayer multicolor photographic elements that do not contain incorporated color-forming couplers. The photographic elements are either of camera speed or elements such as are used for reflection color prints. The elements are coated on any of the usual support materials such as paper, other fibrous support, cellulose acetate or any of the synthetic polymers used for photographic film supports.
  • My antistain agents are dispersed in hydrophilic colloids in the range of from about 01% to about 90%, by weight, of dry hydrophilic colloid and, preferably, in
  • My antistain agents actively reduce the oxidized form of any of the primary aromatic amine color-developing agents (used in color processes) back to the developing agent or to a form that will not couple with color-forming coupler.
  • Hydrophilic colloid layers of my antistain agents coated between two light-sensitive layers are very effective in preventing oxidized color developing agent formed by development in one light-sensitive layer from wandering into the second layer and forming unwanted dye in the second layer.
  • the pure compounds used as antistain agents such as 2,5-di-n-d0decylhydroquinone required four steps in its synthesis and the pure 2-n-dodecylhydroquinone required two steps.
  • my invention only a one-step synthesis is required, and an antistain agent is obtained which is superior in its chemical and physical properties to any described in the prior art.
  • EXAMPLE 1 (A) Pure 2,S-di-n-dodecylhydroquinone (not of my in vention), designated as Antistain Agent X, is prepared as described in lines 48-68, column 8 of US. Pat. 2,728,659, Loria et al., using four reaction steps (M.P. 108l 10 C.)
  • the mixed isomers of secondary-dodecylhydroquinone are prepared using my invention as follows: In a 500-ml. 4-necked flask, in an oil bath, equipped with a stirrer, distillation head, dropping funnel and thermometer, are placed 55 g. (0.5 mole) of hydroquinone, 18 g. of a silica-alumina catalyst, and ml. of toluene. While stirring, the reaction mixture is heated in the oil bath, and the toluene-water azeotrope is removed. When about 75 ml. is collected, the pot temperature is about C. To the hot reaction mixture is added ml.
  • Antistain Agent X is described as being an improvement over the prior art in its resistance to oxidation. This example demonstrates that a mixture of isomers of similar structure is superior to Antistain Agent X in its resistance to oxidation.
  • Antistain Agent Y i.e., 2,5 -di-tertiaryoctylhydroquinone (outside my invention) is compared with Antistain Agent A prepared in Example 1(B).
  • Two dispersions are made as follows:
  • a solution is made of 40 g. of Antistain Agent Y in g. of tri-cresyl phosphate and this is dispersed in 1 l. of aqueous gelatin containing 8% gelatin;
  • EXAMPLE 3 Three paper-supported multilayer gelatinous silver halide coatings of the compositions illustrated below are exposed to a graduated-density test object, color developed, bleached, fixed, washed and dried.
  • Antistain Agents A and X are determined by measuring the amount of cyan dye formed in Layer 3 resulting from the interaction of oxidized color developer from Layer 1 with the coupler in Layer 3. The results are as follows:
  • the cyan-dye-forming coupler used in Layer 3 of Coating Nos. 1, 2 and 3 is a coupler of the type described in lines 39 through 54 in column 2 of Fierke et al., U.S. Pat. 2,801,171, issued July 30, 1957.
  • the yellow-dye-forming coupler used in Layer 1 of Coating Nos. 1, 2 and 3 is an a-pivalyl acetanilide coupler of the type described in column 5, line 20, all of column 6 and column 7 through line 4 of Weissberger and Kibler, U.S. Pat. 3,265,506, issued Aug. 9, 1966.
  • the silver halide emulsion used in Coating Nos. 1, 2 and 3 is a silver bromoiodide emulsion.
  • the color developer, bleach and fix solutions used in the immediate example have the composition indicated below:
  • Color developer solution Water to 1 l.
  • EXAMPLE 4 A dispersion is made by passing a mixture of 50 g. of Antistain Agent A and 60 g. of gelatin in 600 ml. of water through a colloid mill three times. This, when compared to dispersions of Example 1, is about 19% lighter in weight. The liquid antistain agent requires no additional solvent to make a good dispersion. In photographic tests, this dispersion is shown to be substantially identical to a similar dispersion in solvent.
  • Example 1(C) is repeated using equivalent amounts of collodion, agar-agar, hydroxyethyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and copoly(methylacrylatesodium 3 acryloyloxy-l-methylpropane-l-sulfonate-Z- acetoacetoxyethyl acrylate) in place of gelatin.
  • the superior characteristics of my Antistain Agent A over Antistain Agent X are again demonstrated.
  • EXAMPLE 5 Two multilayer color Elements X and A having a support coated in succession with a red-sensitized, gelatinous silver bromoiodide emulsion layer, a gelatin layer, a green-sensitized, gelatinous silver bromoiodide emulsion layer, a gelatin layer containing a bleachable yellowcolored dye and a blue-sensitive, gelatinous silver bromoiodide emulsion layer are made like the elements described in FIG. 2 in the drawing and in the specification on pages 1 and 2 of Mannes et al., U.S. Pat. 2,252,718, issued Aug. 19, 1941, except that the gelatin layers between the lightsensitive layers contain a dispersion of an antistain agent.
  • the antistain agent containing layers of Element X are coated with the dispersion of Antistain Agent X described in immediate Examples 1(A) and 1(C). Antistain Agent X is found to crystallize in the dispersion before coating, during the coating operation and after coating, resulting in coating imperfections and some product that is unusable.
  • the antistain agent containing layers of Element A or my invention are coated with the dispersion of Antistain Agent A described in immediate Examples 1(B) and 1(C). Antistain Agent A is found not to crystallize before, during or after coating Element A. Element A is free of coating defects and is a product that is superior to Element X.
  • Pieces of Element X and Element A are image exposed and processed as described in U.S. Pat. 2,252,718 from page 1, column 2, line 48 through page 2, line 73. Although processed Element X has c'yan dye stain in the magenta image layer, Element A is free of cyan dye stain.
  • EXAMPLE 6 Two multilayer color Elements Z and B like the element described in Example 2, column 7, line 56 through line 28 in column 8 of a Van Campen, U.S., Pat. 2,956,879, issued Oct. 18, 1960, having a support coated in succession with (1) a blue-sensitive gelatino-silver chlorobromide emulsion layer containing a yellow-dye-forming coupler and an antistain agent, (2) a gelatin layer, (3) a green-sensitized gelatino-silver chlorobromide emulsion layer containing an antistain agent, (4) a gelatin layer containing an ultraviolet-absorbing compound and an antistain agent and (5) a red-sensitized gelatino-silver bromoiodide emulsion layer containing an antistain agent.
  • Element Z a dispersion of Antistain Agent X, as described in immediate Examples 1(A) and 1(C), is used as the antistain agent in each of the layers containing an antistain agent. Crystallization of Antistain Agent X from the dispersion before, during and after coating Element Z results in coating defects and some product that cannot be used.
  • Element B is like .Element Z, except that a dispersion of Antistain Agent A,
  • Examples 2, 3, 5 and 6 are repeated using equivalent amounts of collodion, agar-agar, hydroxyethyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and copoly(methyl acrylate-sodium 3-acryloyloxy-l-methylpropane-l-sulfonate-2-acetoacetoxyethyl acrylate) in place of gelatin. Results similar to those shown in Examples 2, 3, 5 and 6, respectively, are obtained.
  • Antistain Agent B of my invention is a mixture of isomers of 2-secondary-nonylhydroquinone and of 2,5-di-secondary-nonylhydroquinone prepared by a procedure like that used to prepare Antistain Agent A described in Example 1(B), but by substituting :an equimolar amount of l-nonene in place of l-dodecene, and by using nitrobenzene as the solvent in place of toluene.
  • Antistain Agent C of my invention is a mixture of isomers of 2-secondary-hexadecylhydroquinone and of 2, S-di-secondary-hexadecylhydroquinone prepared by a procedure like that used to produce Antistain Agent A in Example 1(B) but by substituting an equimolar amount of l-hexadecene in place of 1-dodecene.
  • Antistain Agent B is substantially superior to pure 2-secondary-nonylhydroquinone and substantially superior to pure 2,5-di-sec ondary-nonylhydroquinone.
  • Antistain Agent C is substantially superior to pure 2-sec- 0ndary-hexadecylhydroquinone and is substantially superior to pure 2,5-di-secondary-hexadecylhydroquinone.
  • My antistain agents are valuable for incorporation in photographic hydrophilic colloid compositions because they are superior to antistain agents outside my invention.
  • dispersions of my antistain agents in hydrophilic colloid can be held prior to coating without crystallizing as do antistain agents outside my invention.
  • My antistain agents are eutectic mixtures (or nearly eutectic mixtures) which have low eutectic points, preferably below room temperature. Solutions of my antistain agents in conventional high-boiling solvents or conventional low-boiling solvents are advantageously dispersed in an aqueous hydrophilic colloid.
  • My liquid antistain agents are advantageously dispersed without solvent in an aqueous hydrophilic colloid.
  • My antistain agents do not form quinhydrone type dyes that some antistain agents outside my invention form.
  • the antistain agents of my invention are used very effectively in photographic elements to prevent the wandering of oxidized color developing agents into layers where they cause unwanted dye formation (from coupling reactions).
  • My antistain agents are easily made by a one-step chemical reaction, instead of the twoor four-step reaction required by prior art compounds.
  • a dispersion in a hydrophilic colloid of a photographic antistain agent that is a mixture of at least two secondary-alkylhydroquinones in which the secondaryalkyl substituents have from 9 to 20 carbon atoms, such that said dispersed antistain agent does not crystallize when held at temperatures below room temperature.
  • a dispersion in a hydrophilic colloid of a photo graphic antistain agent that is a mixture of at least two secondary-alkylhydroquinone isomers in which the secondary-alkyl substituents have from 9 to 20 carbon atoms, such that said dispersed antistain agent does not crystallize when held at temperatures below room temperature.
  • a dispersion in a hydrophilic colloid of a nondiffusible photographic antistain agent that is a mixture of secondary-dodecylhydroquinone isomers that does not crystallize when held at temperatures below room temperature.
  • a dispersion in a hydrophilic colloid of a nondiffusible photographic antistain agent that is a mixture of secondary-alkylhydroquinones containing:
  • a dispersion in gelatin of a nondilfusible, photographic antistain agent that is a mixture containing:
  • a multilayer color photographic element containing hydrophilic colloid layers containing diiferently sensitized silver halide emulsions in which the color images are formed during color processing by the reaction of an oxidized primary aromatic amine color developing agent with color-forming couplers, said element containing at least one hydrophilic colloid layer containing a dispersion of a non-ditfusible antistain agent, the improvement comprising the use of a nondilfusible antistain agent that is a mixture of at least two secondary-alkylhydroquinones in which the secondary-alkyl substituents have from 9 to 20 carbon atoms.
  • a multilayer color photographic element containing hydrophilic colloid layers containing differently sensitized silver halide emulsions in which the color images are formed during color processing by the reaction of an oxidized primary aromatic amine color developing agent With color-forming couplers, said element containing at least one hydrophilic colloid layer containing a dispersion of a nondiffusible antitstain agent, the improvement comprising the use of a nondiifusible antistain agent that is a mixture of at least two secondary-alkylhydroquinone isomers in which the secondary-alkyl substituents have from 9 to 20 carbon atoms.
  • a multilayer color photographic element containing hydrophilic colloid layers containing differently sensitized silver halide emulsions in which the color images are formed during color processing by the reaction of an oxidized primary aromatic amine color developing agent with color-forming couplers, said element containing at least one hydrophilic colloid layer containing a dispersion of a nonditfusible antistain agent, the improvement comprising the use of a nondilfusible antistain agent that is a mixture of at least two secondary-dedocylhydroquinones.
  • a multilayer color photographic element containing hydrophilic colloid layers containing differently sensitized silver halide emulsions in which the color images are formed during color processing by the reaction of an oxidized primary aromatic amine color developing agent with color-forming couplers, said element containing at least one hydrophilic colloid layer containing a dispersion of a nondiffusible antistain agent the improvement comprising the use of a nondiffusible antistain agent that is a mixture of secondary-dodecylhydroquinones containing:
  • a multilayer color photographic element containing hydrophilic colloid layers containing dilferently sensitized silver halide emulsions in which the color images are formed during color processing by the reaction of an oxidized primary aromatic amine color developing agent with color-forming couplers, said element containing at least one hydrophilic colloid layer containing a dispersion of a nondiifusible antistain agent, the improvement comprising the use of a nondiffusible antistain agent that is a isomeric mixture of at least two secondarydodecylhydroquinones.

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Cited By (14)

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Publication number Priority date Publication date Assignee Title
US3930863A (en) * 1973-04-13 1976-01-06 Fuji Photo Film Co., Ltd. Color photographic sensitive material
US3960570A (en) * 1973-02-09 1976-06-01 Fuji Photo Film Co., Ltd. Color photographic silver halide light-sensitive materials
US3982944A (en) * 1974-02-06 1976-09-28 Fuji Photo Film Co Ltd Antifoggant dispersion for color photographic materials
US4179293A (en) * 1977-08-09 1979-12-18 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4293641A (en) * 1979-04-27 1981-10-06 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
DE3308766A1 (de) * 1982-03-11 1983-09-22 Fuji Photo Film Co., Ltd., Minami Ashigara, Kanagawa Lichtempfindliches farbphotographisches material
US4485164A (en) * 1983-07-06 1984-11-27 Eastman Kodak Company Oxidants for reducing post-process D-min increase in positive redox dye-releasing image transfer systems
US4923787A (en) * 1988-04-21 1990-05-08 Eastman Kodak Company Photographic element containing scavenger for oxidized developing agent
US4927744A (en) * 1988-08-05 1990-05-22 Eastman Kodak Company Photographic element having solid particle dispersion oxidized developer scavenger
US4963466A (en) * 1986-07-31 1990-10-16 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material suitable for rapid processes comprising hydroquinone and an antifoggant
US5264332A (en) * 1990-10-08 1993-11-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5415988A (en) * 1992-11-25 1995-05-16 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US6255045B1 (en) 2000-03-13 2001-07-03 Eastman Kodak Company Color photographic element containing improved polymeric disulfonamidophenol for scavenging oxidized developer

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
US2732300A (en) * 1953-06-03 1956-01-24 Unsymmetrical dialkyl hydroquinone

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960570A (en) * 1973-02-09 1976-06-01 Fuji Photo Film Co., Ltd. Color photographic silver halide light-sensitive materials
US3930863A (en) * 1973-04-13 1976-01-06 Fuji Photo Film Co., Ltd. Color photographic sensitive material
US3982944A (en) * 1974-02-06 1976-09-28 Fuji Photo Film Co Ltd Antifoggant dispersion for color photographic materials
US4179293A (en) * 1977-08-09 1979-12-18 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4293641A (en) * 1979-04-27 1981-10-06 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
DE3308766A1 (de) * 1982-03-11 1983-09-22 Fuji Photo Film Co., Ltd., Minami Ashigara, Kanagawa Lichtempfindliches farbphotographisches material
US4485164A (en) * 1983-07-06 1984-11-27 Eastman Kodak Company Oxidants for reducing post-process D-min increase in positive redox dye-releasing image transfer systems
US4963466A (en) * 1986-07-31 1990-10-16 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material suitable for rapid processes comprising hydroquinone and an antifoggant
US4923787A (en) * 1988-04-21 1990-05-08 Eastman Kodak Company Photographic element containing scavenger for oxidized developing agent
US4927744A (en) * 1988-08-05 1990-05-22 Eastman Kodak Company Photographic element having solid particle dispersion oxidized developer scavenger
US5264332A (en) * 1990-10-08 1993-11-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US5415988A (en) * 1992-11-25 1995-05-16 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US6255045B1 (en) 2000-03-13 2001-07-03 Eastman Kodak Company Color photographic element containing improved polymeric disulfonamidophenol for scavenging oxidized developer

Also Published As

Publication number Publication date
CA929781A (en) 1973-07-10
GB1326484A (en) 1973-08-15
CH532799A (fr) 1973-01-15
BE763752A (fr) 1971-08-02
DE2110521A1 (de) 1971-09-09
FR2084069A5 (enrdf_load_stackoverflow) 1971-12-17
DE2110521B2 (de) 1977-01-20
JPS5112250B1 (enrdf_load_stackoverflow) 1976-04-17

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