EP0286850B1 - Method for preventing an organic colored substance from fading by light, stabilized colored compositions and photographic elements and materials - Google Patents

Method for preventing an organic colored substance from fading by light, stabilized colored compositions and photographic elements and materials Download PDF

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Publication number
EP0286850B1
EP0286850B1 EP19880104072 EP88104072A EP0286850B1 EP 0286850 B1 EP0286850 B1 EP 0286850B1 EP 19880104072 EP19880104072 EP 19880104072 EP 88104072 A EP88104072 A EP 88104072A EP 0286850 B1 EP0286850 B1 EP 0286850B1
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Prior art keywords
dye
coupler
colored substance
compound
group
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German (de)
English (en)
French (fr)
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EP0286850A1 (en
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Yutaka Kaneko
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Konica Minolta Inc
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Konica Minolta Inc
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392Additives
    • G03C7/39208Organic compounds
    • G03C7/3924Heterocyclic
    • G03C7/39268Heterocyclic the nucleus containing only oxygen as hetero atoms

Definitions

  • the present invention relates to a method for preventing an organic colored substance from fading by light.
  • organic colored substances generally tend to fade by exposure to light.
  • a number of studies to prevent such fading by light of organic colored substances have been making progress in the fields of, e.g., printing ink, pigments for fibers and color photography.
  • the present invention can be very advantageously used for the purpose of preventing such colored substances from fading by light.
  • the term 'light' used herein implies electromagnetic waves in the range of from 300 nm to 800 nm, including ultraviolet rays of less than about 400 nm, visible rays of from about 400 nm to about 700 nm, and infrared rays of from about 700 nm to about 800 nm.
  • Japanese Patent Publication Open to Public Inspection hereinafter referred to as Japanese Patent O.P.I. Publication
  • Japanese Patent O.P.I. Publication Nos. 134326/1974 and 134327/1974
  • the use of hydroquinone derivatives in Japanese Patent Examined Publication No. 27534/1977
  • Japanese Patent O.P.I. Publication No. 14751/1977 Japanese Patent O.P.I. Publication No. 14751/1977 and U.S. Patent No.
  • British Patent No. 1,451,000 proposes the improvement of the stability of an organic colored substance against light by use of an azomethine quenching compound whose absorption spectrum peak is in a longer wave length region than that of the colored substance.
  • the proposal is disadvantageous in respect that the azomethine quenching compound itself is colored, thus largely affecting the hue of the colored substance.
  • the use of a metallic complex for preventing a polymer from being deteriorated by light is described in J. Polym. Sci., Polym. Chem. Ed., Vol. 12, p. 993 (1974), and J. Polym. Sci., Polym. Lett. Ed., Vol. 13, p.71 (1975).
  • the above objects or the present invention can be accomplished by having an organic colored substance which has at least one absorption maximum in the spectral region of 300 nm to 800 nm when dissolved in methanol be present together with at least one compound having the following Formula (I): wherein R is a substituent, and n is an integer of 0 to 6, provided that where n is 2 or more, the plurality of Rs may be either the same or different from each other and that they may be combined with each other to form a ring.
  • Formula (I) wherein R is a substituent, and n is an integer of 0 to 6, provided that where n is 2 or more, the plurality of Rs may be either the same or different from each other and that they may be combined with each other to form a ring.
  • the substituent represented by the R of the above Formula (I) is not particularly restricted, but typical examples thereof include alkyl aryl, anilino, acylamino, sulfonamido, alkylthio, arylthio, alkenyl and cycloalkyl groups, and in addition, other examples thereof include halogen atoms, cycloalkenyl, alkinyl, heterocyclic, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, hydroxyl, alkoxy, cycloalkoxy, aryloxy, heterocyclic oxy, siloxy, acyloxy, carbamoyloxy, amino, alkylamino, imido, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alk
  • the alkyl group represented by R is preferably one having from 1 to 32 carbon atoms and may be either a straight-chain group or a branched-chain group.
  • the aryl group represented by R is preferably a phenyl group.
  • the acylamino group represented by R is, e.g., an alkylcarbonylamino group or arylcarbonylamino group.
  • the sulfonamido group represented by R is, e.g., an alkylsulfonylamino group or arylsulfonylamino group.
  • the alkyl constituent and the aryl constituent in the alkylthio and arylthio groups, respectively, represented by R include the above-mentioned alkyl and aryl groups represented by R.
  • the alkenyl group represented by R is preferably one having from 2 to 32 carbon atoms, and the cycloalkyl group is preferably one having from 3 to 12 carbon atoms, and more particularly from 5 to 7 carbon atoms.
  • the alkenyl group may be either straight-chain or branched-chain.
  • the cycloalkenyl group represented by R is preferably one having from 3 to 12 carbon atoms, and more preferably from 5 to 7 carbon atoms.
  • the sulfonyl group represented by R is, e.g., an alkylsulfonyl group or arylsulfonyl group.
  • the sulfinyl group is, e.g., an alkylsulfinyl group or arylsulfinyl group.
  • the phosphonyl group is, e.g., an alkylphosphonyl group, an alkoxyphosphonyl group, an aryloxyphosphonyl group or an arylphosphonyl group.
  • the acyl group is, e.g., an alkylcarbonyl group or an arylcarbonyl group.
  • the carbamoyl group is, e.g., an alkylcarbamoyl group or an arylcarbamoyl group.
  • the sulfamoyl group is an alkylsulfamoyl group or an arylsulfamoyl group.
  • the acyloxy group is, e.g., an alkylcarbonyloxy group or an arylcarbonyloxy group.
  • the ureido group is, e.g., an alkylureido group or arylureido group.
  • the sulfamoylamino group is, e.g., an alkylsulfamoylamino group or an arylsulfamoylamino group.
  • the heterocyclic group is preferably a 5- to 7-member heterocyclic group, such as a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group or a 2-benzothiazolyl group.
  • the heterocyclic oxy group is preferably one having a 5- to 7-member heterocyclic ring, such as a 3,4,5,6-tetrahydropyranyl-2-oxy group or 1-phenyltetrazolo-5-oxy group.
  • the heterocyclic thio group is preferably a 5- to 7-member heterocyclic thio group such as a 2-pyridylthio group, a 2-benzothiazolylthio group or 2,4-diphenoxy-1,3,5-triazolo-6-thio group.
  • the siloxy group is, e.g., a trimethylsiloxy group, triethylsiloxy group or dimethylbutylsiloxy group.
  • the imido group is, e.g., a succinemido group, a 3-heptadecylsuccinimido group, phthalimido group or glutarimido group.
  • the spiro compound residue is, e.g., a spiro[3.3]heptane-1-yl.
  • the cross-linked hydrocarbon compound residue is, e.g., a bicyclo[2.2.1]heptane-1-yl, tricyclo[3.3.1.1 3'7 ]decane-1-yl or 7,7-dimethyl-bicyclo[2.2.1]heptane-1-yl.
  • the amount of the compound of this invention to be used is preferably from 5 to 400 mole % based on the organic colored substance to be used in this invention, and more preferably from 10 to 300 mole %.
  • the term 'colored substances' to be used in this invention implies those materials whose color is visible to the human eye in sunlight, and, generally, organic materials which, in a methanol solution, have at least one absorption maximum in a spectral region of from 300 nm to 800 nm.
  • the organic colored substances usable in this invention includes all dyes belonging to groups classified according to their dyeing nature; examples are; water-soluble dyes such as basic dyes, acid dyes, direct dyes, solubilized vat dyes, mordant dyes; water-insoluble dyes such as sulfur dyes, vat dyes, solvent dyes, disperse dyes, azoic dyes, oxidation dyes; and reactive dyes.
  • the organic colored substance to be used in this invention also includes all image-forming dyes known in the prior art such as, a dye formed by the oxidative coupling reaction between a dye-forming coupler for use in the photographic field and a color developing agent, a dye formed by the oxidation of a DRR (dye releasing redox) compound, a dye released or formed by the reaction of the oxidation product of a color developing agent with a DDR diffusable dye releasing coupler, a dye formed from an amidrazon compound, a dye developer and a dye for use in the silver dye bleach process.
  • image-forming dyes known in the prior art such as, a dye formed by the oxidative coupling reaction between a dye-forming coupler for use in the photographic field and a color developing agent, a dye formed by the oxidation of a DRR (dye releasing redox) compound, a dye released or formed by the reaction of the oxidation product of a color developing agent with a DDR diffusable dye releasing
  • (I-10) A dye formed by the oxidation of a DRR compound as described in, e.g., U.S.B351,673, U.S. Patent Nos. 3,932,381, 3,928,312, 3,931,144, 3,954,476, 3,929,760, 3,942,987, 3,932,380, 4,013,635 and 4,013,633, Japanese Patent O.P.I. Publication Nos. 113624/1976, 109928/1976, 104343/1976, 4819/1977 and 149328/1978, Research Disclosure Nos. 15157 (1976), 13024 (1975).
  • Yellow dyes including azo dyes such as Direct Fast Yellow GC (C.I. 29000), Crysophenine (C.I. 24895), benzoquinone-type dyes such as Indigo Golden Yellow IGK (C.I. 59101), Indigosol Yellow 2GB (C.I. 61726), Algosol Yellow GCA-CF (C.I. 67301), Indanthrene Yellow GF (C.I. 68420), Mikethrene Yellow GC (C.I. 67300), Indathrene Yellow 4GK (C.I.
  • anthraquinone-type dyes polycyclic-type solubilized vat dyes and other vat dyes; magenta dyes including azo dyes such as Sumilight Supra Rubinol B (C.I. 29225), Benzo Brilliant Keranin B (C.I. 15080), indigoid-type dyes such as Indigosol Brilliant Pink IR (C.I. 73361), Indigosol Violet 15R (C.I. 59321), Indigosol Red Violet IRRL (C.I. 59316), Indanthrene Red Violet RRK (C.I. 67895), Mikethrene Brilliant Violet BBK (C.I.
  • vat dyes comprised of benzoquinone-type and anthraquinone-type compounds; and cyan dyes including azo dyes such as Direct Sky Blue 6B (C.I. 24410), Direct Brilliant Blue 2B (C.I. 22610), Sumilight Supra Blue G (C.I. 34200), phthalocyanine dyes such as Sumilight Supra Turquoise Blue G (C.I. 74140), Indanthrene Turquoise Blue 5G (C.I. 69845), Indanthrene Blue GCD (C.I. 73066), Indigosol 04G (C.I. 73046) and Anthrasol Green IB (C.I. 59826).
  • azo dyes such as Direct Sky Blue 6B (C.I. 24410), Direct Brilliant Blue 2B (C.I. 22610), Sumilight Supra Blue G (C.I. 34200), phthalocyanine dyes such as Sumilight Supra Turquoise Blue G (C.I. 74140
  • the dye-forming couplers which are to form the dyes of (I-14) include the yellow, magenta and cyan dye-forming-type couplers. These couplers may be of either the so-called 4-equivalent type as described in, e.g., U.S. Patent Nos. 3,277,155 and 3,458,315 or the 2-equivalent type wherein the carbon atom in the coupling position is substituted by a substituent (split-off group) that can split off at the time of the coupling reaction.
  • yellow dye-forming coupler examples include benzoylacetanilide-type couplers and pivaloylacetanilide-type couplers.
  • magenta dye-forming coupler examples include 5-pyrazolone-type couplers, pyrazolotriazole-type couplers, imidazopyrazole-type couplers, pyrazolopyrazole-type couplers, pyrazolotetrazole-type couplers, pyrazolinobenzimidazole-type couplers and indazolone-type couplers.
  • examples of the cyan dye-forming coupler include phenol-type couplers, naphthol-type couplers and pyrazoloquinazolone-type couplers.
  • yellow couplers capable of forming the yellow dyes of (I-14):
  • These yellow couplers include those compounds described in, e.g., West German OLS Patent Nos. 2,057,941 and 2,163,812, Japanese Patent O.P.I. Publication Nos. 26133/1972, 29432/1973, 65321/1975, 3631/1976, 50734/1976, 102636/1976, 66835/1973, 94432/1973, 1229/1974 and 10736/1974, and Japanese Patent Examined Publication Nos. 33410/1976 and 25733/1977, and can be synthesized according to those methods as described in these publications.
  • magenta couplers capable of forming the magenta dyes of (I-14):
  • magenta couplers include those compounds described in, e.g., U.S. Patent No. 3,684,514, British Patent No. 1,183,515, Japanese Patent Examined Publication Nos. 6031/1965, 6035/1965, 15754/1969, 40757/1970 and 19032/1971, Japanese Patent O.P.I. Publication Nos. 13041/1975, 129035/1978, 37646/1976 and 62454/1980, U.S. Patent No. 3,725,067, British Patent Nos. 1,252,418 and 1,334,515, Japanese Patent O.P.I. Publication Nos.
  • the cyan couplers for forming the cyan dyes of (I-14), although not specially restricted, are desirably phenol-type cyan couplers.
  • cyan couplers capable of forming the cyan dyes of (I-14):
  • These cyan couplers include those compounds described in, e.g., U.S. Patent Nos. 2,423,730 and 2,801,171, Japanese Patent O.P.I. Publication Nos. 112038/1975, 134644/1975, 109630/1978, 55380/1979, 65134/1981, 80045/1981, 155538/1982, 204545/1982, 98731/1983 and 31953/1984, and may be synthesized in accordance with those methods as described in these publications.
  • dyes are formed from them by reaction with the oxidation product of a color developing agent.
  • the above color developing agent includes aminophenols and phenylenediamines, and these color developing agents may be used in admixture.
  • the following Formula (II) is representative of suitable aminophenols.
  • the aminophenol can also used in the form of a complex with a mineral acid, for example, H2SO4, HCl, HN3, or a hydrate of the complex, for example, 3 2 H2SO4.H2O.
  • R1 is as alkyl or alkoxy group or halogen atom
  • m is an integer of 0 to 4
  • R2 and R3 each represents hydrogen, an alkyl group (e.g., methyl, ethyl, propyl and butyl) or a substituted alkyl group. (e.g., an alkoxy alkyl, hydroxy alkyl or alkylsulfonamino alkyl group).
  • the following Formula (III) is representative of suitable phenylenediamines.
  • the phenylenediamine can also used in the form of a complex with a mineral acid for example, H2SO4, HC , HNO3, or a hydrate of the complex for example, 3 2 H2SO4.H2O.
  • R4 is an alkyl or alkoxy group or a halogen atom, and is an integer of 0 to 4;
  • R5 represents hydrogen or -SO3X (wherein, X represents an alkali metal atom.);
  • R6 and R7 each represents hydrogen an alkyl group (e.g., methyl, ethyl, propyl, butyl and octyl), or a substituted alkyl group (e.g., a hydroxyalkyl group, a alkoxyalkyl group, and an alkyl sulfonylamino alkyl group.
  • the developing agents D-1 - D-8 can also be used in the form of a complex with a mineral acid, for example H2SO4, HCl, HNO3, or a hydrate of the complex, for example, 3 2 H2SO4.H2O.
  • a mineral acid for example H2SO4, HCl, HNO3, or a hydrate of the complex, for example, 3 2 H2SO4.H2O.
  • Compounds suitably usable as the organic colored substance of this invention include anthraquinone, quinoneimine, azo, methine, azomethine, polymethine, indoamine, indophenol and formazan dyes.
  • the organic colored substances more suitably usable in this invention are methine, polymethine, indoamine and indophenol dyes, and those compounds having the following group:
  • the phenyl group is an unsubstituted phenyl group or a phenyl group which is substituted by, e.g., an alkyl group, alkoxy group, a halogen atom or an amino group.
  • those dyes usable as the organic colored substance are the foregoing dyes of (I-14), and most preferably, the dyes of (I-14) which are formed by the reaction between those pyrazolotriazole-type magenta dye-forming couplers given in M-5, M-6, M-7, M-8, M-9, M-10, M-12, M-13 and M-14 and those phenylenediamine color developing agents given in D-1 through D-8.
  • the compound of this invention in the state of reducing the fading of an organic colored substance by light, no restrictions are put on the condition of the presence of the compound together with the colored substance.
  • the compound may be dissolved uniformly along with the organic colored substance in one and the same solvent, or it may also be mordanted along with the organic colored substance in one and the same mordant.
  • the compound of this invention or the organic colored substance may be impregnated into a solid-solution or semi-solid-solution layer of the organic colored substance or the compound of this invention.
  • a specially preferred method is such that, in accordance with those methods as described in U.S. Patent Nos. 2,332,027, 2,801,170, 2,801,171, 2,272,191 and 2,304,940, the compound of this invention and organic colored substance are dissolved into a high-boiling solvent, if necessary, in combination with a low-boiling solvent, and the solution is then added to and dispersed into a hydrophilic colloid solution, for example a gelatine solution; and the resulting liquid is then coated on a substrate and dried.
  • a hydrophilic colloid solution for example a gelatine solution
  • hydroquinone derivatives may be used in combination, and in this case, two or more kinds of the compound of this invention may also be mixed to be used.
  • Another particularly preferred method is such that, in accordance with those methods as described in U.S. Patent Nos. 2,322,027, 2,801,170, 2,801,171, 2,272,191 and 2,304,940, the compound used in accordance with this invention and a precursor of an organic colored substance such as a dye-forming coupler a DDR compounds, or a DDR couplers are dissolved into a high-boiling solvent, if necessary, in combination with a low-boiling solvent, the solution is then added to and dispersed into a hydrophilic colloid solution, and the resulting liquid is then coated on a substrate and dried, and after that, the precursor of the organic colored substance is converted into an organic colored substance.
  • hydroquinone derivatives, ultraviolet absorbing agents or known agents for preventing the fading of dye images may be used in combination, and in this case, two or more kinds of the compounds may also be mixed to be used.
  • One or two or more kinds of the compound usable in accordance with this invention, precursors of organic colored substance such as dye-forming couplers, DRR compounds and DDR couplers, and, if necessary hydroquinone derivatives, ultraviolet absorbing agents or known agents, e.g., for preventing the fading of dye images, are simultaneously dissolved into a high-boiling solvent such as an organic acid amide, carbamate, ester, ketone, hydrocarbon or urea derivative; particularly, dibutyl phthalate, tricresyl phosphate, di-iso-octyl azelate, dibutyl sebacate, trihexyl phosphate, decalin, N,N-diethylcaprylamide, N,N-diethyllaurylamide, pentadecyl-phenyl ether or fluoroparaffin, if necessary, in combination with a low boiling solvent such as ethyl
  • a high-boiling solvent such as an organic
  • both the colored substance precursor and the compound of this invention may be present in any of or some of the hydrophilic colloid layers of the photographic color material. These materials may also be present in both a light-sensitive element and a non-light-sensitive element.
  • the colored substance and the compound of this invention are incorporated in such a non-light-sensitive element, such as the dye-image receiving element to be used in a photographic diffusion transfer film unit, it is desirable that these be mordanted. Accordingly, in such application, the compound used in accordance with this invention is preferred to be in such a molecular form as can be retained in the mordant layer of the image-receiving element so as not to move away from the colored substance to be stabilized.
  • the silver halide emulsion thereof is one prepared generally by dispersing silver halide grains into a hydrophilic colloid.
  • Suitable silver halides include silver chloride, silver bromide, silver iodide, silver chlorobromide, silver iodobromide, silver chloroiodobromide, and mixtures of these silver halides.
  • silver halide emulsions in order to be sensitized to desired spectral wavelength regions, may be optically sensitized by using various sensitizing dyes. These silver halide emulsions may also be chemically sensitized in the usual manner in the photographic field.
  • a compound known as an antifoggant or stabilizer to the photographic field for the purpose of preventing fogging of and/or stabilizing the characteristics of the color photographic material during its manufacturing process, storage or photographic processing.
  • various photographic additives such as hardening agents, plasticizers, brightening agents, antistatic agents and coating aids, may be added alone or in combination of two or more kinds of them.
  • a color photographic material to which this invention is to be applied may be either a coupler-in-emulsion-type color photographic material containing dye-forming couplers or a coupler-in-developer-type color photographic material to be processed in a dye-forming-coupler-containing developer.
  • the above-mentioned coupler-in-emulsion-type color photographic material containing dye-forming couplers may be processed in the usual manner, whereby a color image is obtained.
  • the principal processes in this instance are color developing, bleaching and fixing and, if necessary, washing, stabilizing, and the like processes. Of these processes, two or more processes may take place in a monobath such as in the bleach-fix process.
  • the color developing takes place usually in an alkaline solution containing an aromatic primary amine developing agent.
  • aromatic primary amine developing agents are Exemplified Developing Agents D-1 through D-6 which have been disclosed hereinabove.
  • the processing of the photographic material takes place automatically inside the light-sensitive material.
  • the developing agent is contained in a rupturable container.
  • developing agents usable, in addition to the foregoing D-1 through D-6 are N-methylaminophenol, 1-phenyl-3-pyrazolidone, 1-phenyl-4,4-dimethyl-3-pyrazolidone, 1-phenyl-4-methyl-hydroxymethyl-3-pyrazolidone and 3-methoxy-N,N-diethyl-p-phenylenediamine.
  • the color photographic materials can be various color light-sensitive photographic materials such as color positive film, color photographic paper, color negative film, color reversal film, color diffusion transfer film units and color photographic materials for the silver dye bleach process.
  • a magenta dye (the absorption maximum of it in its methanol solution: 538 nm) having the following structural formula: was dissolved into 4 ml of trioctyl phosphate and 8 ml of ethyl acetate, and this solution was then emulsifiedly dispersed into 10 ml of an aqueous 10% gelatin solution containing 2 ml of an aqueous 0.5 % sodium dodecylbenzene sulfonate solution.
  • this emulsifiedly dispersed liquid was mixed with 300 ml of an aqueous 5% gelatin solution, and the mixture was then coated on a both-side-polyethylene-laminated paper support, whereby a sample was obtained.
  • This sample was designated as Sample No.1.
  • Samples No.2 and No.3 were prepared by coating in the same manner as in Sample No.1 except that comparative compounds having the following structural formulas (a) and (b) were added each in a quantity of 0.5 g in place of the above compound in preparing the emulsifiedly dispersed liquid.
  • Example 2 15 different samples (No. 16 through No. 30) were prepared in quite the same manner as in Example 1 except that the magenta dye of Example 1 was replaced by a magenta dye having the following structural formula (the absorption maximum of it in its methanol solution: 536 nm). Each of the obtained samples was exposed over a period of 150 hours to the light of a xenon fadeometer to thereby examine the light resistance of each sample. The results are shown in Table 2.
  • the samples which use the antifading agents of the present invention show more excellent light-fading-preventive effect than do the comparative samples which use metallic complex compounds of the prior art, and the samples of the invention show little or no change of color to dark brown, and their satisfactory color remained intact even after the light resistance test.
  • Samples No.32 and No.33 were prepared by coating in the same manner as in the above except that 24 g each of Comparative Compounds (c) and (d) having the following structural formulas were added, respectively, in preparing the above emulsifiedly dispersed liquid.
  • the faded degree of each sample is given in terms of the change in the density of the portion that had had an initial density of 1.0 before being subjected to the fading test.
  • the antifading agents according to this invention have more excellent light-fading-preventive effect than do the conventional organic antifading agents.
  • the antifading agents of this invention have a large light-fading-preventive effect also on the cyan color-formed dye.
  • a thermally developable light-sensitive element was prepared by using the following materials: Gelatin ... A mixture of limed gelatin for photographic use and phenylcarbamoylated gelatin (Type 17819PC, produced by Ruthlow Co.) mixed in the ratio by weight of 2 : 1. PVP ... Polyvinyl pyrrolidone (K-30) Solid thermal solvent ... p-butoxybenzamide Liquid thermal solvent .. 1,2,4-butane-triol Color developing agent ... A mixture of the following color developing agent A and B mixed in the molar ratio of 7 : 3. Organic silver salt ... 5-methylbenzotriazole silver salt Light-sensitive silver halide . The same silver halide as described in the example of Japanese Patent Application No. 254257/1986 was used. The above numerical values are in g/m2, provided, however, that the organic silver salt and light-sensitive AgX are in silver equivalence.
  • thermally developable light-sensitive element was subjected to 4000 CMS exposure by being exposed through a step wedge and a green filter to a tungsten light, and then it was superposed on each of the above thermally developed-image receiving elements with their coated surfaces brought into contact with each other, and the unit was preheated for 4 seconds at 100°C, and then heated under pressure (thermally developed) at 150°C for 90 seconds.
  • the preheating and the heating under pressure were performed by using a thermal developing apparatus as shown in Figure 1 of Japanese Patent O.P.I. Publication No. 153651/1986.
  • magenta color image was obtained on the surface of the image-receiving element. This magenta color image was examined with respect to its photographic characteristics and its stability against light. The results are also given in Table 6.
  • the maximum reflection density and the minum reflection density of the magenta color image of each sample were measured with a green light by using a SAKURA Densitometer PDA-65 (manufactured by Konishiroku Photo Industry Co., Ltd.).
  • the dye density residual rate (%) of each magenta color image was examined in the manner that each magenta image-having sample was exposed over periods of 5 days and of 10 days to the light of a xenon fadeometer (SUGA Tester WE-6X-HC).
  • the absorption maximum of the formed magenta image in its methanol solution was 528 nm.
  • the antifading agent of this invention even when used in a thermally developable light-sensitive material, is excellently effective in preventing the dye image of the light-sensitive material from fading. Also, by using the antifading agent of this invention and the ultraviolet absorbing agent in combination, the antifading effect can be further improved.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP19880104072 1987-03-18 1988-03-15 Method for preventing an organic colored substance from fading by light, stabilized colored compositions and photographic elements and materials Expired - Lifetime EP0286850B1 (en)

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JP62065411A JPH0697333B2 (ja) 1987-03-18 1987-03-18 有機着色物質の光褪色防止方法
JP65411/87 1987-03-18

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EP0286850B1 true EP0286850B1 (en) 1993-05-19

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EP1984564A4 (en) 2006-02-03 2013-04-03 Nanopaper Llc FUNCTIONALIZATION OF PAPER COMPONENTS

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BE705617A (ja) * 1966-11-30 1968-03-01
JPS54136581A (en) * 1978-04-14 1979-10-23 Fuji Photo Film Co Ltd Stabilizing method for organic basic substance to light
JPS5833247A (ja) * 1981-08-21 1983-02-26 Konishiroku Photo Ind Co Ltd 画像の変褪色防止方法

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JPS63229454A (ja) 1988-09-26
JPH0697333B2 (ja) 1994-11-30

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