US3573050A - Color photographic layers comprising non-diffusible 5-hydroxycoumarans as stabilizing compounds - Google Patents

Color photographic layers comprising non-diffusible 5-hydroxycoumarans as stabilizing compounds Download PDF

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US3573050A
US3573050A US803080*A US3573050DA US3573050A US 3573050 A US3573050 A US 3573050A US 3573050D A US3573050D A US 3573050DA US 3573050 A US3573050 A US 3573050A
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dye
atoms
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Kent C Brannock
Gregory J Lestina
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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
    • 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

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  • Nondiffusible S-hydroxycoumaran stabilizer compounds which have either a substituted amino group or an alkoxy group substituted on the carbon atoms in the 2 position are advantageously incorporated in hydrophilic colloid layers of photographic elements in which color photographic dye images are to be stored for viewing.
  • the stabilizer compounds protect dye images against the fading effects of prolonged exposure to light.
  • This invention relates to photography, photographic materials including color photographic materials containing dye image stabilizing agents, and methods for improving the stabilities of dyes in photographic materials.
  • 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 conditions involving, for example, long periods of exposure to sunlight, or other ultraviolet radiant illumination, the dyes may fade, resulting in deterioration in the quality of the picture.
  • Another object of our invention is to provide novel image dye stabilizing agents which do not form highly Patented Mar. 30, 1971 colored oxidation products in the processing baths, e.g., bleach baths, etc., used in color photographic processing.
  • Another object of our invention is to provide novel color photographic image-forming layers comprising hydrophilic colloid film-forming binders containing finely particulate dispersions of solutions of our S-hydroxycoumaran stabilizing agents.
  • a further object is to provide novel dispersions of our S-hydroxycoumaran stabilizing agents which can be incorporated in silver halide emulsion layers without adverse emulsion effects.
  • hydrophilic colloid layers for the storage of dye images that are stabilized against the effects of prolonged exposure to light by the incorporation of a nondifiusible S-hydroxycoumaran, such as, a 2-amino-S-hydroxycoumaran and a 2-alkoxy-5-hydroxycoumaran.
  • Our stabilizing compounds are particularly advantageous for the stabilization of indophenol dye images, indoaniline dye images, azomethine dye images and azo dye images that are stored in hydrophilic colloid layers for viewing.
  • dye images are either formed as nondilfusible dye images in the hydrophilic colloid layer containing our stabilizer compound or are formed as diffusible dye images in another hydrophilic colloid layer and transferred to a receiving layer containing a hydrophilic colloid layer with our stabilizer compound.
  • Our invention provides valuable technical advances.
  • R represents hydrogen, an alkyl group, preferably an alkyl group having from 1 to 22 carbon atoms (e.g., methyl, ethyl, isopropyl, butyl, t-butyl, cyclohexyl, octyl, t-octyl, dodecyl, octadecyl, docosyl, etc.) and the atoms necessary to complete with R a fully hydrogenated hydrocarbon ring of 4 to 7 atoms, preferably 5 to 6 atoms in the ring (e.g., cyclobutane, cyclopentane, cyclohexane, cycloheptane, etc.); R represents an alkyl group having from 1 to 22 carbon atoms as described for R and the atoms necessary to complete with R a fully hydrogenated hydrocarbon ring of 4 to 7 atoms, preferably 5 to 6 atoms in the ring (e.g., cyclobutan
  • alkoxy group having from 1 to '22 carbon atoms as has been described for :R and the atoms necessary to complete with R, a 5, 6 or 7 membered carbocyclic ring such as, a cyclopentane ring (e.g., cyclopentane, methylcyclopentane, methoxycyclopentane, etc.), a cyclohexane ring (e.g., cyclohexane, ethylcyclohexane, ethoxycyclohexane, w-hydroxyhexylcyclohexane, etc.) and a cycloheptane ring (e.g., cycloheptane, ethylcycloheptane, rnethoxycycloheptane, w hydroxybutoxycycloheptane, etc.); Z represents a Rs N group or a OR group; R represents an alkyl group, preferably an alkyl
  • cyclobutyl cyclopentyl, cyclohexyl, 2-methylcyclohexyl, cycloheptyl, etc.
  • an aryl group such as, a phenyl (e.g., phenyl, p-tolyl, o-tolyl, o-ethylphenyl,
  • p-isopropylphenyl, etc. a naphthyl group, e.g., ot-naphthyl, 2-methyl-a-naphthyl, fl-naphthyl, etc.), a heterocyclic group having from 4 to 7 and preferably 5 to 6 atoms in the heterocyclic ring (e.g., pyridyl, quinolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, oxazolyl, benzoxazolyl, imidazolyl, benzimidazolyl, etc.), and the atoms necessary to complete with R a heterocyclic ring having from 4 to 7 atoms and preferably 5 to 6 atoms in the ring (e.g., piperidino, morpholino, thiamorpholino, pyrrolidinyl, etc.); and R represents an alkyl group having from 1 to 22 carbon
  • Our stabilizers are particularly eflicacious in protecting dyes produced by chromogenic development of any of the well-known 5-pyrazolone couplers used in photography for magenta dye formation.
  • Typical magenta dyes are those produced by color development of couplers described in U.S. patents, such as, 2,600,788, 2,725,292, 2,908,573, 3,006,759, 3,062,653, 3,152,896, 3,311,476 and Young U.S. application Ser. No. 458,455, filed May 24, 1965, now U.S. Pat. No. 3,419,391, which couplers are herein incorporated by reference.
  • Cyan dye-forming couplers of such U.S. patents as 2,474,293, 2,725,292, 2,895,826, 2,908,573 produce cyan dyes upon chromogenic development that are advantageously stabilized against light exposure by our stabilizing compounds.
  • Yellow dye-forming couplers of U.S. Pat. 2,908,573 produce yellow dyes that are made less subject to the fading effects of prolonged exposure to light by the presence of our stabilizing compounds.
  • Our stabilizing agents are incorporated alone or together with a color-forming coupler in a dye image-forming layer of a color photographic element.
  • a useful methd of dispersing our stabilizing compounds is that described for dispersing couplers in Mannes et al. U.S. Pat. 2,304,939, issued Dec. 15, 1942; Jelley et al. U.S. Pat. 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. Pat. 2,801,170, and Fierke et al. U.S. Pat. 2,801,171, both issued July 30, 1957, and Julian U.S. Pat. 2,949,360, issued Aug. 16, 1960, in which low-boiling or watersoluble organic solvents are used with high-boiling solvent.
  • our stabilizing agents can be contained in the same dispersion with nondifiusing couplers, or in a separate dispersion, and the couples can optionally be dispersed directly in the emulsion.
  • Highboiling solvents useful in dispersing the -hydroxycoumaran stabilizer compounds of our invention include di-nbutylphthalate, benzylphthalate, triphenyl phosphate, tri-ocresyl phosphate, diphenyl mono-p-tert-butylphenyl phosphate, monophenyl di-p-tert-butylphenyl phosphate, diphenyl mono-o-chlorophenyl phosphate, monophenyl dio-chlorophenyl phosphate, tri-p-tert-butylphenyl mono(5- tert-butyLZ-phenylphenyl)phosphate, 2,4 di n-amylphenol, 2,4-di-t-amylphenol,
  • 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, fi-ethoxyethyl acetate, tetrahydrofurfuryl adipate, Carbitol acetate (diethyleneglycol monoacetate), 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 monoacetate
  • methoxytriglycol acetate methoxytriglycol acetate
  • methyl Cellosolve acetate acetonyl acetone
  • diacetone alcohol butyl Carbitol, buty
  • 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 ino the same dispersion, for example, other stabilizing agents, antistain agents, e.g., ballasted hydroquinones,
  • 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 monomethyl p phenylenediamine hydrochloride, N,N dimethyl p phenylenediamine hydrochloride, 2 amino 5 diethylaminotoluene hydrochloride, 2 amino 5 (N-ethyl-N-laurylamino) toluene, N ethyl N B (methylsulfonamido)ethyl-3- methyl 4 aminoaniline sulfate, N ethyl N (5- methylsulfonamidoethyl) 4 aminoaniline, 4 (N- ethyl N ,6 hydroxyethyl)aminoaniline, etc., the paminophenols and their substitution products where the amino group is unsubstituted,
  • 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.
  • image-forming couplers competing couplers for example, image-forming couplers competing couplers, antifoggants, hardeners, an alkali metal sulfite, bisulfite, alkaline buffer salts, bromide, iodide, etc.
  • 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 storage of photographic dye images, such as, a receiving sheet for receiving a ditt'usible 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 chlorobromoiodide, silver bromoiodide, etc.), a light-sensitive diazo compound (as in diazo-type material), etc.
  • a light-sensitive material such as silver halide (e.g., silver chloride, silver bromide, silver iodide, silver chlorobromide, silver chlorobromoiodide, silver bromoiodide, etc.), a light-sensitive diazo compound (as in diazo-type material), 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, alginates, synthetic resins, e.g., polyvinyl alcohol, copoly(ethylacrylate, acrylic acid) polyvinyl pyrrolidone, etc.
  • Some colloids used to advantage are polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in U.S. Pat.
  • a far hydrolyzed cellulose ester such as cellulose acetate hydrolyzed to an acetyl content of 1926%, as described in U.S. Pat. 2,327,808, a water-soluble ethanolamine cellulose acetate as described in U.S. lPat. 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 U.S. Pat. 2,541,474, zein as described in U.S. Pat. 2,563,791, a vinyl alcohol polymer containing urethane carboxylic acid groups of the type described in U.S.
  • the emulsions used in the photographic element of our invention can be chemically or optically sensitized.
  • 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 Pat. 75,676, dlivr June 19, 1 961.
  • Mordant receiving sheets in which our compounds can be used to advantage are described in French Pat. 1,361,293, dlivr Apr. 6, 1964.
  • the dilfusible-image dyes are mordanted in such receiving sheets 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 Six single layer coatings are made on a paper support of gelatino silver halide emulsions containing 80 mg./ft. of magenta dye-forming coupler No. 6 of US. Pat. 3,062,653 (i.e., 1 (2 chloro-4,6-dimethylphenyl)-3- ⁇ 3- [a (3 pentadecylphenoxy)-butyramido]benzamido ⁇ -5- pyrazolone), 80 mg./ft. of coupler solvent tricresylphosphate, 320 mg./ft. of gelatin, and 160 mg./ft. of silver, and the amount of addenda indicated in Table I.
  • magenta dye-forming coupler No. 6 of US. Pat. 3,062,653 i.e., 1 (2 chloro-4,6-dimethylphenyl)-3- ⁇ 3- [a (3 pentadecylphenoxy)-butyramido]benzamido ⁇ -5-
  • Compound A is 7 t butyl 2,2 dimethyl 6 hydroxy- 4-isopropylchromanol (of French Pat. 1,478,141)
  • Compound B is 7 t butyl 2,2,4 trimethyl 6 hydroxychromanol (of French Pat. 1,478,141)
  • Compound X is 6 t butyl 2,2 dimethyl 5 hydroxy coumaran (of US. Pat. 2,535,058)
  • the coatings are exposed with a 1B intensity scale sensitometer and processed to color negatives using the following process.
  • magenta dye density of 1.2 is identified in each of the processed coatings which are then subjected to a 10 day northlight fading test (SANS, i.e., simulated average north sky light equivalent to 120,000 foot candle hours).
  • SANS 10 day northlight fading test
  • the magenta dye loss at the identified areas having an original density of 1.2 is determined and listed in Table 2.
  • EXAMPLE 2 Six single layer gelatinous coatings containing a pre formed magenta dye are made on a support.
  • the coatings have the following compositions:
  • the magenta dye is prepared by reacting the coupler, 1 (2 chloro 4,6 dimethylphenyl) 3 ⁇ 3 [a (3- pentadecylphenoxy)butyramido] benzamido ⁇ 5 pyrazolone dissolved in tricresyl phosphate with the oxidized form of color developing agent, N ethyl ,8 methanesulfnoamidoethyl 3 methyl 4 aminoaniline sulfate.
  • the coatings are subjected to SANS light fading test described in Example 1 but for 3 weeks.
  • the stabilizer and the loss in magenta dye density (from an area of the dye image having an original magenta dye density of 1.2) are listed in Table 3.
  • Example 2 is repeated using magenta dyes produced from the magenta coupler and the oxidized form of other well-known color developing agents including those disclosed herein previously. Similar results are obtained when Example. 2 is repeated using any of the other well-known magenta dyeforming couplers with the oxidized form of any of the well-known color-developing agents described herein previously.
  • EXAMPLE 3 Four single layer gelatinous silver halide emulsion coatings containing the magenta dye-forming coupler, 1-(2- chloro 4,6 dimethylphenyl) 3 ⁇ 3 [a (3 pentadecylyphenoxy)butyramido] benzamido ⁇ 5 pyrazolone are made on a paper support.
  • the gelatinous silver bromoiodide emulsion is prepared as described by Trivelli and Smith in the Photographic Journal, page 330, May 1939.
  • the coatings have the following compositions:
  • Coupler (identified above)50 mg./ft.
  • Stabilizer (as indicated in Table 5)equimolar to coupler Gelatin-440 IIlg./ft.
  • the coatings are dried and given /2 second exposure on a 1B intensity scale sensitometer, followed by color processing at 75 F. as follows:
  • the color developer is a conventional color developer solution containing benzyl alcohol, sodium sulfite, the color developing agent, N ethyl 3 methanesulfonamidoethyl 3 methyl 4 aminoaniline sulfate and an alkali to give a pH of about 10.
  • a conventional stop-fix bath containing sodium thiosulfate, sodium sulfite, acetic acid, boric acid and potassium alum is used for the stopfix step and for the hardening fix steps in the process.
  • a conventional alkali metal ferricyanide-bromide bleach bath is used, and a conventional aqueous citric acid stabilizer bath having a pH of 3.5 is used in the process.
  • An area having a magenta dye density of about 1.2 is identified on each processed coating before exposing them to a 3 weeks SANS fading test. The results are summarized in the following table.
  • Example 3 is repeated using magenta dye-forming S-pyrazolone couplers 1 through 12 of US. Pat. 2,600,788 in place of the coupler used in Example 3. The results are similar to those obtained in Example 3.
  • Example 3 is repeated using magenta dye-forming 5-pyrazolone couplers 6 through 9 of US. Pat. 2,908,573 in place of the coupler used in Example 3. The results are similar to those obtained in Example 3.
  • Example 3 is repeated using colored magenta dyeforming 5-pyrazolone couplers 1 through 5, 7 and 8 of US. Pat. 2,725,292, in place of the coupler used in Example 3.
  • the dye of the coupler remaining in the color processed layer as well as the magenta dye formed by coupler that coupled with oxidized color 10 developer during color processing are both stabilized against the destructive effects of prolonged exposure to light in the SANS fading test.
  • EXAMPLE 7 A gelatinous silver halide emulsion is prepared as described by Trivelli and Smith in The Photographic Jourrial, page 330, May 1939. One portion of this emulsion is coated as a control identified as coating No. 1 on a cellulose acetate film support. Coating No. 2 is made of another portion of the emulsion to which our stabilizing compound No. 4 is added so that it is coated at a rate of 10- mole (of stabilizer) per ft. Coating No. 3 is made of another portion of the emulsion to which our stabilizing compound N0. 4 is added so that it is coated at the same rate as stabilizing compound No. 4.
  • the coatings are given a sensitometric exposure and color developed in a conventional magenta color developing solution containing the color developing agent, 4-amino-N-ethyl-N- (fl-methanesulfonamidoethyl) m toluidine sesquisulfate monohydrate, an alkali, an alkali metal sulfite and the magenta dye-forming coupler, 1-(2,4,6-trichlorophenyl)- 3-(2,4-dichloroanilino)-5-pyrazolone (coupler No. 6 of US. Pat. 3,152,896).
  • the color developed coatings are then water washed, bleached in a conventional alkali metal ferricyanide-bromide bleach, fixed in a conventional alkali metal thiosulfate fixing bath washed and dried.
  • Our stabilizer compounds 4 and 7 in coatings 2 and 3 impart valuable protection to the magenta dye images as is illustrated by 3 weeks SA-NS test as described in Example 2.
  • Example 7 Similar results are obtained when Example 7 is repeated with other dye-stabilizing compounds of our invention and with other primary aromatic amine color developing agents and other magenta dye-forming couplers including couplers 1, 2, 3, 4, 5, 7 and 8 of US. Pat. 3,152,896 as well as other diffusible magenta dye-forming couplers well know in the art.
  • Our stabilizer compounds are advantageously incorporated in the receiving layer of image receiving sheets to stabilize the dye images transferred thereto.
  • image transfer dyes made from compounds I through XLVI of US. Pat. 3,227,551 and transferred to receiving layers containing our stabilizer compounds have improved stability to prolonged exposure to light.
  • dye images produced from dye developers such as those described in US. Pat. 3,404,002 and transferred to receiving layers containing our stabilizer compounds are found to fade less upon prolonged exposure to light than the same images transferred to a receiving layer containing none of our stabilizers.
  • the azo dye images produced in silver dyebleach elements containing our stabilizers are substantially more stable to prolonged exposure to light than images that are not so protected.
  • our stabilizers are advantageously incorporated in silver dye-bleach materials, such as those described in US. Patents 2,418,624, 2,420,630, 2,420,631, etc.
  • our stabilizing compounds are also advantageously incorporated in the azo dye image-forming layer of any of the diazo-type elements that are used for duplicating images.
  • our stabilizer compound is incorporated into the polymeric matrix layer containing the diazo salt(s) and coupler(s) where it advantageously protects the azo dye image produced upon development of the light image exposed layer.
  • R4 Ra wherein R R and R are as described previously, according to the procedure described in Brannock et al. US. Pat. 3,184,457 issued May 18, 1965, incorporated herein as part of this application by reference.
  • Compounds of Formula I in which Z represents an alkoxy group are advantageously prepared by reacting an enol ether compound of the formula:
  • a hydrophilic colloid layer containing a color photographic dye image said layer containing at least one nondiffusible S-hydroxycoumaran selected from the class consisting of a 2-amino-5-hydroxycoumaran and a 2- alkoxy-5-hydroxycoumaran.
  • a hydrophilic colloid layer containing a color photographic dye image said layer containing at least one nondiffusible 5-hydroxycoumaran selected from the class consisting of those have the formula:
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, and the necessary atoms to complete with R a fully hydrogenated hydrocarbon ring having from 4 to 7 atoms in the ring;
  • R represents a group selected from the class consisting of an alkyl group and the necessary atoms to complete with R a fully hydrogenated hydrocarbon ring having from 4 to 7 atoms in the ring;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an alkoxy group;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, an alkoxy group and the necessary atoms to complete with R a saturated ring fused with the phenol ring;
  • R represents a member selected from the class consisting of hydrogen, an
  • t-butylquinone 6-t-but0xy-2-methylquinone. 2-t-butyl-5-ethoxyquinone. 2-t-butyl-3-phenylquinone. 2-t-butyl-3-ethoxyquinone.
  • enamines of Formula II are advantageously prepared by the reaction of known secondary amines with known aliphatic aldehydes having at least one rat-hydrogen.
  • the enol ethers of Formula IV are derived from known aliphatic aldehydes having only one tat-hydrogen atom.
  • quinones of Formula III are well known in the art and are either available or prepared by well known methods.
  • Our hydrophilic colloid layers containing dye images such as, indophenol dye images, indoaniline dye images, azomethine dye images and azo dye images and a stabilizing amount of our nonalkyl-Z-alkoxy-S-hydroxycoumarans provide a valuable technical advance in color image re production because these images are substantially more N stable than the same images in layers containing no stabilizer or a prior art stabilizer.
  • R represents a group selected from the class consisting of an alkyl group, an aryl group, a heterocyclic group having from 4 to 7 atoms in the ring and the necessary atoms to complete with R a heterocyclic ring having from 4 to 7 atoms in the ring;
  • R represents a group selected from the class consisting of an alkyl group, an aryl group, a heterocyclic group having from 4 to 7 atoms in the ring and the necessary atoms to complete with R a heterocycic ring having from 4 to 7 atoms in the ring; and R represents an alkyl group.
  • a dye image-forming layer comprising a film-forming hydrophilic colloid layer containing at least one nonditfusible, S-hydroxycoumaran selected from the class consisting of a Z-amino-S-hydroxycoumaran and a 2-alkoxy- 5-hydr0xycoumaran.
  • a dye image-forming silver halide emulsion layer comprising a film-forming hydrophilic colloid layer containing at least one nondiffusible S-hydroxycoumaran selected from those having the formula:
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, and the necessary atoms to complete with R a fully hydrogenated hydrocarbon ring having from 4 to 7 atoms in the ring;
  • R represents a group selected from the class consisting of an alkyl group and the necessary atoms to complete with R a fully hydrogenated hydrocarbon ring having from 4 to 7 atoms in the ring;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an alkoXy group;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, an alkoxy group and the necessary atoms to complete with R a saturated ring fused with the phenol ring;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, an alkoxy group, a mononuclear aryl group and the necessary atoms to complete with R; a saturated ring fused with the phenol ring;
  • Z represents a
  • an element for color photography designed for dye image storage said element comprising a support layer and at least one hydrophilic colloid layer for said dye image
  • the improvement comprising the use of a hydrophilic colloid layer containing a stabilizing amount of a nondiffusible, S-hydroxycoumaran selected from the class consisting of a 2-amino-5-hydr0xycoumaran and a 2- alkoxy-S-hydroxycoumaran for the said dye image.

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052216A (en) * 1975-06-13 1977-10-04 Agfa-Gevaert, A.G. Color photographic material containing a hydroxyindane
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0242013A2 (en) 1986-01-20 1987-10-21 Konica Corporation Silver halide color photographic light-sensitive material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US4735893A (en) * 1984-06-08 1988-04-05 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4741980A (en) * 1985-09-19 1988-05-03 Konishiroku Photo Industry Co., Ltd. Method for increasing color-fastness of organic coloring matter
US4767697A (en) * 1985-01-21 1988-08-30 Fuji Photo Film Co., Ltd. Silver halide color photographic material
EP0601836A2 (en) 1992-12-07 1994-06-15 Konica Corporation Silver halide light sensitive color photographic material
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco 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
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5545514A (en) * 1994-07-14 1996-08-13 Konica Corporation Silver halide light-sensitive color photographic material
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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54101501U (enrdf_load_stackoverflow) * 1977-12-28 1979-07-17

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052216A (en) * 1975-06-13 1977-10-04 Agfa-Gevaert, A.G. Color photographic material containing a hydroxyindane
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
US4735893A (en) * 1984-06-08 1988-04-05 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4931382A (en) * 1984-06-08 1990-06-05 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4767697A (en) * 1985-01-21 1988-08-30 Fuji Photo Film Co., Ltd. Silver halide color photographic material
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
US4741980A (en) * 1985-09-19 1988-05-03 Konishiroku Photo Industry Co., Ltd. Method for increasing color-fastness of organic coloring matter
EP0242013A2 (en) 1986-01-20 1987-10-21 Konica Corporation Silver halide color photographic light-sensitive material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
EP0601836A2 (en) 1992-12-07 1994-06-15 Konica Corporation Silver halide light sensitive color photographic material
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
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5696289A (en) * 1994-06-30 1997-12-09 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5705676A (en) * 1994-06-30 1998-01-06 Minnesota Mining And Manufacturing Company Chromogenic leuco 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
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
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material

Also Published As

Publication number Publication date
BE746518A (enrdf_load_stackoverflow) 1970-07-31
GB1282706A (en) 1972-07-26
FR2037417A5 (enrdf_load_stackoverflow) 1970-12-31
DE2008376A1 (de) 1970-09-03
BR7017029D0 (pt) 1973-02-20
JPS496208B1 (enrdf_load_stackoverflow) 1974-02-13
CA946201A (en) 1974-04-30

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JPS5952421B2 (ja) 色素画像褪色防止剤を含有するカラ−写真材料