US3432300A - 6-hydroxy chromans used as stabilizing agents in a color photographic element - Google Patents

6-hydroxy chromans used as stabilizing agents in a color photographic element Download PDF

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US3432300A
US3432300A US452889A US3432300DA US3432300A US 3432300 A US3432300 A US 3432300A US 452889 A US452889 A US 452889A US 3432300D A US3432300D A US 3432300DA US 3432300 A US3432300 A US 3432300A
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dye
image
hydroxy
color
compound
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Gregory J Lestina
Warren A Reckhow
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • 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
    • 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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/24—Photosensitive materials characterised by the image-receiving section
    • G03C8/246—Non-macromolecular agents inhibiting image regression or formation of ghost images

Definitions

  • Dye stabilizing quantities of 6-hydroxy chroman characterized by having an alkyl group on one of the two positions ortho to the hydroxy, and hydrogen on the other ortho position, as well as on the meta position of the benzene ring of said compound are advantageously incorporated in hydrophilic colloid layers in which color photographic dye images are to be formed or to which ditfusible dye images are to be transferred so that the 6-hydroxy chroman is contiguous to the dye image that is to be stabilized.
  • Photographic elements containing the immediate 6-hydroxy chromans are processed without producing unwanted light absorption produced by the stabilizing agents outside of the invention and provide considerable improvement inthe light stability of the image dyes in the layer containing the stabilizing agent.
  • This invention relates to color photography and color photographic materials, and more particularly to improved color photographic materials containing new dye image stabilizing agents, new methods for improving the stabilities of image dyes in color photographic materials and new ballasted dye image stabilizing agents.
  • dye images by the chromogenic development of silver halide photographic materials involving the coupling reaction of oxidized primary aromatic amino developing agents with coupling compounds to form indophenol, indamine, azomethine, phenoxazine, phenazine, and similar dyes, is well known.
  • the subtractive color process of color formation is ordinarily used and the image dyes customarily formed are cyan, magenta, and yellow, which are the colors that are complementary to the primary colors red, green and blue, respectively.
  • phenolic couplers i.e., phenols and naphthols
  • pyrazolone or cyanoacetyl couplers are used to form the magenta dye image
  • acylacetamide or dibenzoylmethane couplers are used to form the yellow dye image.
  • the color-forming coupler may be applied in a developer solution or incorporated in the light-sensitive photographic emulsion layer or in another dye-image-forming layer, so that, during development, it is available to react with oxidized color developing agent formed as the result of latent image development.
  • the dye images formed in such processes are not indefinitely stable to ultraviolet radiation so that under rigorous viewing or display condition involving, for example, long periods of exposure to sunlight, or other ultraviolet radiant illumination, the dyes may fade, result ing in deterioration in the quality of the picture.
  • azomethine dyes to ultraviolet radiation have been achieved by the use of a variety of agents which can be added to the emulsion in processing, or more conveniently, in manufacture.
  • the need remains for further enhancement of the resistance of these dyes to actinic light and, indeed, this requirement is increasing as recent and continuing technological improvements in the durability of the photographic layers and supports are making practical the use of prints in exposed locations, indoors and out, which would have been unthinkable a few years ago.
  • the R groups on the above formula may be hydrogen or alkyl, particularly alkyl of from 1 to 18 carbon atoms.
  • R and R groups is an alkyl group, the other is hydrogen.
  • the alkyl groups can be straight, branched chain or cyclic.
  • the number of individual alkyl groups, and their respective size, is determined by the resistance to diffusion and the solubility characteristics required.
  • Cycloalkyl groups such as cyclohexyl, cyclopentyl, etc., are used as substituents, although the preferred substituents will be simple alkyl groups, e.g., methyl, isopropyl, t-butyl, t-octyl, n-octadecyl, etc., and one or more of these alkyl groups may be substituted, for example, with such groups as hydroxyl, halogen, carboxyl, carbalkoxy, acyloxy (e.g., acetoxy), sulfo, sulfonyloxy, amido (e.g., acetamido, ethylsulfonamido, benzamido, etc.), and an ether group, e.g., alkoxy (such as, methoxy, butoxy, dodecyloxy, etc.), aryloxy (such as, phenoxy, naphthoxy, etc.
  • Our stabilizing agents are used to advantage in improving the stability of the indophenol, indoaniline and azomethine image dyes such as those produced by chromogenic development.
  • Typical examples are the dyes derived from any of the commonly used cyan, magenta, and yellow-forming couplers, by coupling with any of the oxidized primary aromatic amine color developing agents used in color photographic processing.
  • Typical couplers may be found, for example, in the following U.S. patents:
  • our nondiffusible stabilizing agents are incorporated in the layer which will contain the final dye image. They can be used to advantage in any or all of the emulsion layers of a color film. They can be incorporated either alone or with couplers.
  • a useful method of dispersing our stabilizing compounds is that described for dispersing couplers in Mannes et al., U.S. Patent 2,304,939, issued Dec. 15, 1942; Jelley et al., U.S. Patent 2,322,027, issued June 15, 1943; etc., in Which high-boiling organic solvents are used to dissolve the material. Other applicable methods are described in Vittum et al., U.S. Patent 2,801,170, and
  • our stabilizing agents can be contained in the same dispersion with nondifiusing couplers, or in a separate dispersion, and the couplers can optionally be dispersed directly in the emulsion.
  • Highboiling solvents useful in dispersing the 6-hydroxy chromans of our invention include di-n-butylphthalate, benzylphthalate, triphenyl phosphate, tri-o-cresyl phosphate, diphenyl mono-p-tert-butylphenyl phosphate, monophenyl di-p-tert-butylphenyl phosphate, diphenyl mono-ochlorophenyl phosphate, monophenyl di-o-chlorophenyl phosphate, tri-p-tert-butylphenyl mono(5-tert-butyl-2 phenylphenyl)-phosphate, 2,4-di-n-amylphenol, 2,4-di-tamylphenol
  • the organic solvents include:
  • Low-boiling, substantially water-insoluble organic solvents such as methyl, ethyl, propyl, and butyl acetates, isopropyl acetate, ethyl propionate, sec-butyl alcohol, ethyl formate, butyl formate, nitromethane, nitroethane, carbon tetrachloride, chloroform, etc., and
  • Water-soluble organic solvents such as methyl isobutyl ketone, )9-ethoxyethyl acetate, fi-butoxy, tetrahydrofurfuryl adipate, Carbitol acetate (diethyleneglycol monocetate), methoxytriglycol acetate, methyl Cellosolve acetate, acetonyl acetone, diacetone alcohol, butyl Carbitol, butyl Cellosolve, methyl Carbitol, methyl Cellosolve, ethylene glycol, diethylene glycol, dipropylene glycol, acetone, methanol, ethanol, acetonitrile, dimethylformamide, dioxane, etc.
  • Carbitol acetate diethyleneglycol monocetate
  • methoxytriglycol acetate methoxytriglycol acetate
  • methyl Cellosolve acetate acetonyl acetone
  • diacetone alcohol butyl Carbit
  • Combinations of two or more of the new and improved dye-stabilizing agents of our invention may be used. These agents may also be used in combination with other addenda in the same dispersion, for example, other stabilizing agents, antistain agents, e.g., ball'asted hydroquinones, phenolic antioxidants, etc.
  • Other stabilizing agents e.g., antistain agents, e.g., ball'asted hydroquinones, phenolic antioxidants, etc.
  • the selection of the specific stabilizer compound and the concentration used in each layer of a multilayer film can be varied over a wide range, and will depend on the improvement in resistance to fading required for each of the image dyes in the respective layers.
  • any of the well known primary aromatic amino colorforming silver halide developing agents such as the phenylenediamines, e.g.,
  • N,N-diethyl-p-phenylenediamine hydrochloride N-monomethylp-phenylenediamine hydrochloride, N,Ndimethyl-p-phenylenediamine hydrochloride, 2-amino-5-diethy1aminotoluene hydrochloride, Z-amino-S-(N-ethyl-N-laurylamino)toluene, N-ethyl-N-fl-(methylsulfonamido)ethyl-3-methyl-4- aminoaniline sulfate, N-ethyl-N-(B-methylsulfonamidoethyl)-4-aminoaniline, 4-(N-ethyl-N-[i-hydroxyethyl)aminoaniline, etc.,
  • the p aminophenols and their substitution products where the amino group is unsubstituted may be used to develop photographic coatings containing our stabilizers.
  • Various other materials may be included in the developer solutions depending upon the particular requirements, for example, image-forming couplers, competing couplers, antifoggants, hardeners, an alkali metal sulfite, bisulfite, alkaline buffer salts, bromide, iodide, etc., and the thickening agents used in viscous developer compositions.
  • a typical developer solution is given in Example 1, but does not limit the invention.
  • Our stabilizers are incorporated in hydrophilic colloid layers intended for the preparation of photographic dye images, such as, a receiving sheet for receiving a diifusible transferred dye image or a dye-image forming layer containing a light-sensitive material such as silver halide (e.g., silver chloride, silver bromide, silver iodide, silver chlorobromide, silver chlorobromiodide, silver bromoiodide, etc.), ZnO, ZnS, CdS, CdSe, NiS, etc.
  • a light-sensitive material such as silver halide (e.g., silver chloride, silver bromide, silver iodide, silver chlorobromide, silver chlorobromiodide, silver bromoiodide, etc.), ZnO, ZnS, CdS, CdSe, NiS, etc.
  • Hydrophilic colloids used to advantage in the image layers include any of the hydrophilic colloids used in image-forming layers and in receiving layers, such as gelatin, and gelatin derivatives, casein and other proteinaceous colloids, hydrophilic cellulosic derivatives, e.g., carboxymethyl cellulose, lalgin-ates, synthetic resins, e.g., polyvinyl alcohol, copoly(ethyl-acrylate, acrylic acid) polyvinyl pyrrolidone, etc.
  • Some colloids used to advantage are polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in US.
  • Patent 2,286,215 a far hydrolyzed cellulose ester, such as cellulose acetate hydrolyzed to an acetyl content of 19-26%, as described in US. Patent 2,327,808, a water-soluble ethanolamine cellulose acetate as described in US. Patent 2,322,085, a polyacrylamide having a combined acrylamide content of 30-60% and a specific viscosity of 025-15 on an imidized polyacrylamide of like acrylamide content and viscosity as described in US. Patent 2,541,474, zein as described in US. Patent 2,563,791, a vinyl alcohol polymer containing urethane carboxylic acid groups of the type described in U.S.
  • Patent 2,768,154 or containing cyano-acetyl groups, such as the vinyl alcohol-vinyl cyano-acetate copolymer as described in US. Patent 2,808,331, or a polymeric material which results from polymerizing a protein or a saturated acylated protein with a monomer having a vinyl group as described in US. Patent 2,852,382.
  • cyano-acetyl groups such as the vinyl alcohol-vinyl cyano-acetate copolymer as described in US. Patent 2,808,331, or a polymeric material which results from polymerizing a protein or a saturated acylated protein with a monomer having a vinyl group as described in US. Patent 2,852,382.
  • the emulsions used in the photographic element of our invention can be chemically or optically sensitized.
  • the stabilizers of our invention may also be used to advantage in image-forming layers, either alone or with image-forming compounds other than silver halide, such as ZnO, ZnS, CdS, CdSe, NiS, etc., with binders such as gelatin, polyvinyl alcohol, etc.
  • image-forming compounds other than silver halide such as ZnO, ZnS, CdS, CdSe, NiS, etc.
  • binders such as gelatin, polyvinyl alcohol, etc.
  • Our stabilizing compounds are also used to advantage with mordants in dye-image receiving sheets for dye diffusion transfer processes such as are described in French Patent 75,676, dated June 19, 1961.
  • Mordant receiving sheets in which our compounds can be used to advantage are described in French Patent 1,361,293, dated Apr. 6, 1964.
  • the diifusible-image dyes are mordanted in such receiving scheets containing our stabilizer compounds, they exhibit marked improvement in light stability.
  • emulsions containing our stabilizer compounds are coated on photographic supports in the form of multilayer color photographic elements wherein at least three differently sensitized emulsion layers are coated over one another on the support.
  • the support is coated in succession with a red-sensitive layer, a green-sensitive layer, and a blue-sensitive layer either with or without a Carey Lea filter layer between the blue-sensitive and green-sensitive layers.
  • the three differently color sensitized layers may be arranged in any other order over one another that is desirable; however, the Carey Lea filter layer (i.e., yellow colloidal silver) would not be put over the blue-sensitive layer.
  • these light-sensitive layers are arranged on the same side of the support.
  • our stabilizing agents are used in quantities ranging from 0.25 mole to 20 moles of stabilizer per 1 mole of coupler used (or per 1 mole of dye produced).
  • the preferred range is from 1 mole to 5 moles of stabilizer per mole of coupler (or per mole of dye produced).
  • Example 1 Single layer gelatin silver bromoiodide coatings con taining magenta-image-forming coupler, 1-(2,4-dimethyl- 6-chlorophenyl) 3 ⁇ 3-[ot-(3-pentadecylphenoxy)butyrarnido] benzamido ⁇ -5-pyrazolone, and stabilizer compound in coupler solvent, tri-o-cresylphosphate, were made for our stabilizer compounds 1, 3, 4, 5, 6 and 7, respectively.
  • a control coating containing no stabilizer compound was also prepared. Each of these coatings contained 44 parts by weight of gelatin, 16 parts by weight of silver, 5 parts by weight of coupler, 2 parts by weight of stabilizer, and 5 parts by weight of coupler solvent. Strips of the above mentioned coatings were each given -second exposure on a 1B intensity scale sensitometer and processed to color negatives according to the following process:
  • Example 2 Single layer gelatin silver bromoiodide coatings containing an image-forming coupler and stabilizer compound No. 1 in coupler solvent, tri-o-cresylphosphate, were made using the couplers given in the following table, respectively. A control coating containing no stabilizer was made using each of the couplers, respectively. Each of these coatings contained 50 parts by weight of gelatin, 15 parts by weight of silver, and 5 parts by weight of coupler solvent. The amount of stabilizer compound No. 1 and the amount and identity of the particular couplers used in each of these coatings is given in the following Table II. In each of these coatings, the coupler and stabilizer compound were dispersed together in the coupler solvent.
  • TAB LE III Percent improvement in light stability of the image dyes relative to that of the image dye in the control Coating No.
  • the color developer solution used to develop this coating and its control contained 4-amino-3-methoxy-N ethyl-N-(B-hydroxyethyl) aniline in place of the p'phenylenediantine given in the developer solution of Example 1.
  • Example 3 A single layer gelatin silver bromoiodide coating containing 1 part by weight of stabilizer Compound No. '1 in a solvent mixture of 2 parts by weight of tri-o-cresylphosphate and 1 part by weight of 2,2'-methylenebis[6- l-rnethylcyclohexyl)-4-methylphenol] was made. This coating also contained 14 parts by weight of gelatin and 10 parts by weight of silver. A control coating containing no stabilizer compound was also prepared. These coatings demonstrate the utility of our stabilizer compounds in coatings containing no coupler.
  • Exposed samples of the above mentioned coatings were processed to color positives by developing them first in a black-and-white type developer, then reexposing the residual silver halide (i.e., positive image) and developing them in a color developer solution similar to that given in Example 1 above except that the solution also contained the magenta-image-forming coupler, 1-(2,4,6-trichlorophenyl)- 3-(4-nitroanilino)-5-pyrazolone.
  • the processed strips were then subjected to light fade exposures as described in Example 1.
  • the image dye in the coating containing our stabilizer compound exhibited a markedimprovement in light stability over that of the image dye in the control coating (i.e., containing no stabilizer compound).
  • the other stabilizers of our invention are prepared to advantage by a similar method using the appropriate intermediates.
  • Compond No. 2 was prepared by reacting t-butylhydroquinone with 2-methyl- 2,4-pentadiene
  • Compound No. 5 was prepared by reacting t-butylhydroquinone with Z-methyl-butadiene
  • Compound -No. 3 was prepared by reacting isopropylhydroquinone with 2-methyl-2,4-pentadiene
  • Compound No. 4 was prepared by reacting isopropylhydroquinone with 2,5-dimethyl-2,4-hexadiene
  • alkyl group on the position ortho to the hydroxy group of our stabilizer compounds may be either straight or branched chain, the branched chain groups such as, for example, t-butyl, isopropyl, t-octyl, are preferred.
  • our stabilizer compounds can be employed without producing adverse photographic effects on the emulsions of said couplers, and without becoming colored when coatings containing them are put through the processing solutions such as developers, fixing baths, bleaching baths, etc.
  • Our new and improved stabilizer compounds can be dispersed readily in image-forming layers either with or without coupler and without causing adverse effect on the coupler reactivity, and without causing interaction with either fresh or oxidized color developing agents.
  • a hydrophilic colloid layer containing a color photographic dye image said layer containing at least one 6-hydroxychroman dye-stabilizing compound, said compound having an alkyl group attached to one of the positions ortho to the 6-hydroxyl group of said compound and hydrogen atoms attached to the remaining two open positions ortho and meta to said hydroxyl group.
  • a hydrophilic colloid layer containing a color photographic dye image said layer containing at least one 6-hydroxychoman dye-stabilizing compound having the formula:
  • R and R each represents a member selected from the group consisting of the hydrogen atom and an alkyl group such that only one of the groups is an alkyl group; R R and R each represents a member selected from the class consisting of the hydrogen atom and an alkyl group.
  • a dye-image-forming silver halide emulsion layer comprising a film-forming hydrophilic colloid containing at least one 6-hydroxychroman dye-stabilizing compound, said compound having an alkyl group attached to one of the positions ortho to the 6-hydroxyl group of said compound and hydrogen atoms attached to the remaining two open positions ortho and meta to said hydroxyl group.
  • a dye-image-forming silver halide emulsion layer comprising a film-forming hydrophilic colloid containing at least one 6-hydroxychroman dye-stabilizing compound having the formula:
  • R and R each represents a member selected from the group consisting of the hydrogen atom and an alkyl group such that only one of the groups is an alkyl group; R R and R each represents a member selected from the class consisting of the hydrogen atom and an alkyl group.
  • a multilayer multicolor element containing silver halide emulsions and incorporated color-forming couplers the improvement comprising the incorporation of a 6-hydroxychroman dye-stabilizing agent in at least one of said layers, said dye-stabilizing agent having an alkyl group attached to one of the positions ortho to the 6-hydroxyl group of said agent and hydrogen atoms attached to the remaining two open positions ortho and meta to said hydroxyl group.
  • R and -R each represents a member selected from the group consisting of the hydrogen atom and an alkyl group such that only one of the groups is an alkyl group;
  • R R and R each represents a member selected from the class consisting of the hydrogen atom and an alkyl group.
  • an image-forming silver halide emulsion layer comprising the use of a 6-hydroxychroman dye-stabilizing agent, said dye-stabilizing agent having an alkyl group attached to one of the positions ortho to the 6-hydroxyl group of said agent and hydrogen atoms at tached to the remaining two open positions ortho and meta to said hydroxyl group.
  • R and R each represents a member selected from the group consisting of the hydrogen atom and an alkyl group such that only one of the groups is an alkyl group; R R and R each represents a member selected from the class consisting of the hydrogen atom and an alkyl group.

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US452889A 1965-05-03 1965-05-03 6-hydroxy chromans used as stabilizing agents in a color photographic element Expired - Lifetime US3432300A (en)

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DE2526468A1 (de) * 1975-06-13 1976-12-30 Agfa Gevaert Ag Farbphotographisches material
US4015990A (en) * 1974-07-09 1977-04-05 Mitsubishi Paper Mills, Ltd. Color photographic lightsensitive material
US4042394A (en) * 1973-05-07 1977-08-16 Eastman Kodak Company Photographic dye image stabilization
US4113495A (en) * 1976-06-11 1978-09-12 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material capable of providing stable color images
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US4761181A (en) * 1986-01-24 1988-08-02 Fuji Photo Film Co., Ltd. Method for stabilizing organic base substances to light
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EP0601836A2 (en) 1992-12-07 1994-06-15 Konica Corporation Silver halide light sensitive color photographic material
US5470985A (en) * 1993-07-27 1995-11-28 Konica Corporation Metal complex compound
US5478721A (en) * 1995-01-31 1995-12-26 Eastman Kodak Company Photographic elements containing emulsion stabilizers
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5534390A (en) * 1993-11-12 1996-07-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5545514A (en) * 1994-07-14 1996-08-13 Konica Corporation Silver halide light-sensitive color photographic material
US5576165A (en) * 1993-07-07 1996-11-19 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5672722A (en) * 1993-11-12 1997-09-30 Fuji Photo Film Co., Ltd. Color fade inhibitor
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent

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US4113495A (en) * 1976-06-11 1978-09-12 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material capable of providing stable color images
US4159910A (en) * 1976-08-09 1979-07-03 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing color image fading inhibitor
US4178184A (en) * 1976-10-23 1979-12-11 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye-fading inhibitors
US4138259A (en) * 1976-10-29 1979-02-06 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4174220A (en) * 1976-10-30 1979-11-13 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye fading inhibitors
US4207111A (en) * 1976-12-28 1980-06-10 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide color photographic materials
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US4713317A (en) * 1984-05-22 1987-12-15 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
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US4921317A (en) * 1984-07-16 1990-05-01 Fuji Photo Film Co., Ltd. Infrared absorbent comprising a metal complex compound containing two thiolato bidentate ligands
US4767697A (en) * 1985-01-21 1988-08-30 Fuji Photo Film Co., Ltd. Silver halide color photographic material
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US4741980A (en) * 1985-09-19 1988-05-03 Konishiroku Photo Industry Co., Ltd. Method for increasing color-fastness of organic coloring matter
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US4761181A (en) * 1986-01-24 1988-08-02 Fuji Photo Film Co., Ltd. Method for stabilizing organic base substances to light
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US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US5576165A (en) * 1993-07-07 1996-11-19 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5470985A (en) * 1993-07-27 1995-11-28 Konica Corporation Metal complex compound
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US5534390A (en) * 1993-11-12 1996-07-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
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US5705676A (en) * 1994-06-30 1998-01-06 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5545514A (en) * 1994-07-14 1996-08-13 Konica Corporation Silver halide light-sensitive color photographic material
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5478721A (en) * 1995-01-31 1995-12-26 Eastman Kodak Company Photographic elements containing emulsion stabilizers
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Also Published As

Publication number Publication date
BE680470A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) 1966-10-17
DE1547684A1 (de) 1970-02-26
GB1141812A (en) 1969-02-05

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