Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
  • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
  • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
  • G03C7/30523—Phenols or naphtols couplers
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/32—Colour coupling substances
  • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/32—Colour coupling substances
  • G03C7/34—Couplers containing phenols
  • G03C7/344—Naphtholic couplers

Definitions

• This invention relates to a cyan dye-forming coupler and, more specifically, to a silver halide light-sensitive color photographic material, which contains a 1-naphthol-type cyan dye-forming coupler having in its second-position an orthoalkoxyphenylcarbamoyl group and fourth-position an aliphaticoxy group, an aryloxy group or a heterocyclicoxy group.
• a color image is formed by imagewise exposing a silver halide light-sensitive color photographic material and undergoing color development in which a dye image is formed by the reaction of a dye-forming coupler with a paraphenylenediamine-type color developing agent.
• phenol type and naphthol type compounds are representative and, among them, naphthol-type compounds are used in color negative films for their photographic characteristics showing sufficient light absorption in the long wavelength region and high coupling reactivity.
• 2-arylcarbamoyl-1-naphthol-type couplers disclosed in U.S. Patent No.3,488,193 have an advantage that color density is not tend to decrease when processed with a fatigued bleaching solution, however, they have disadvantages that the maximum absorption wavelength shifts to short wavelength side in high color density area and color reproduction property is poor.
• 2-arylcarbamoyl-1-naphthol type cyan couplers disclosed in Japanese Patent Publication No.62-837475(1987), have an advantage that the maximum absorption wavelength does not shift remarkably to short wavelength side, however, the cyan couplers have a disadvantage that, in conventional color nega type developing, the maximum absorption wavelength becomes often the wavelength of not less than 700nm.
• a preferable wavelength range is within the range of 685nm to 700nm, so that the maximum wavelength is longer than the preferable wavelength and color reproduction is poor.
• Japanese Patent Publication No.5-40891(1993) discloses naphthol-type compounds, in which the aryl group at 2-position is substituted by a branched alkoxyl group, whereby shift of the maximum absorption wavelength was unsatisfactorily improved, however, there was still a problem that fog increases when the light-sensitive color photographic material containing this type of coupler is stored before exposure under high temperature and high humidity conditions.
• the first object of the present invention is to provide a silver halide color photographic light-sensitive material, which is capable of producing a dye image of enhanced sensitivity and improved image quality by employing a 1-naphthol-type cyan dye-forming coupler.
• the second object of the present invention is to provide a silver halide color photographic light-sensitive material comprising a 1-naphthol-type cyan dye-forming coupler which is capable of forming a cyan dye image having a favorable spectral absorption property and, especially, having a favorable maximum absorption wavelength
• the third object of the present invention is to provide a silver halide color photographic light-sensitive material which comprises a 1-naphthol-type cyan dye-forming coupler where the density loss of the cyan dye produced therefrom is reduced even when it is processed with a fatigued bleaching solution.
• the fourth object of the present invention is to provide a silver halide light-sensitive color photographic material having improved storage stability before exposure.
• R1 and R2 straight-chained, branched or cyclic alkyl group, an alkenyl group and an alkynyl group, which may have a substituent, can be mentioned.
• the aliphatic group represented by R includes preferably, those having 4 to 20 carbon atom such as, for example, butyl group, iso-butyl group, pentyl group, neo-pentyl group, isopentyl group, hexyl group, cyclohexyl group, octyl group, 2-ethylhexyl group, decyl group, dodecyl group, 2-methyloctyl group, 2-butyloctyl group, 2-hexyldecyl group, 5,7-dimethyloctyl group, 3,5,5-trimethylhexyl group and hexadecyl group.
• the aliphatic group represented by R2 includes preferably an alkyl group having 1-20 carbon atoms such as, for example, methyl group, ethyl group, propyl group, iso-propyl group and those mentioned concerning R1.
• the total number of carbon atoms contained in R1 and R2 is 8 or more, and it is preferably to 10 to 32 and, more preferably, at least one of them is a branched alkyl group.
• R3 represents a substituent including, for example, an aliphatic group, an aryl group, a halogen atom, a hydroxyl group, an amino group, a carbonamide group, a sulfonamido group, a ureido group, an acyloxy group, an aliphaticoxy group, an aliphatic thio group, an aryl thio group and a sulfamoylamino group.
• aliphatic group represented by R in Formula 1 a straight-chained, branched or cyclic alkyl group having 1 to 30 carbon atoms and a substituted alkyl group are preferable and, a substituted alkyl group having 2 to 30 carbon atoms is more preferable.
• substituted or unsubstituted phenyl or naphthyl group is preferable.
• a substituted phenyl group having 6 to 30 carbon atoms is especially preferable.
• substituent of the substituted phenyl group for example, those groups mentioned as the substituent for the substituted alkyl group for R can be mentioned.
• a five-member or six-member heterocyclic ring containing therein at least one hetero atom selected from nitrogen, oxygen and sulfur, or a fused ring formed from the above-mentioned five-member or six-member heterocyclic ring and another aromatic ring or a heterocyclic ring is preferable, and these fused rings may be substituted by a proper substituent, such as those mentioned as the substituent for the substituted alkyl group represented by R.
• R an aliphatic group or an aryl group is preferable.
• compounds represented by Formula(l) especially preferable compound can be presented by Formula 3. wherein R4, R5, R6 and R7 independently represent a straight-chained or branched alkyl group, provided that the total number of carbon atoms contained in R4 through R6 is 6 through 28; R' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
• substituent for the substituted alkyl group or the substituted phenyl group represented by R' those groups mentioned as the examples of the substituent for the substituted alkyl group in the aliphatic group as R can be mentioned.
• the aliphatic group represented by Q1 and Q2 is straight-chained , branched or cyclic alkyl, alkenyl or alkynyl group, and the aliphatic group may have a substituent.
• an alkyl group having 4 to 20 carbon atoms is preferable, and the alkyl group preferable includes, for example, butyl group, iso-butyl group, pentyl group, neo-pentyl group, iso-pentyl group, hexyl group cyclohexyl group, octyl group, 2-ethylhexyl group, decyl group, dodecyl group ,2-methyloctyl group, 2-butyloctyl group, 2-hexyldecyl group, 5,7-di-methyloctyl group, 3,5,5-trimethylhexyl group and hexadecyl group.
• an alkyl group having 2 to 20 carbon atoms is preferable and, more preferably, a branched or a cyclic alkyl group having 4 to 20 carbon atoms, including, for example, sec-butyl group, tert-butyl group, 1,1,3,3-tetramethylbutyl group, cyclopentyl group, cyclohexyl group, 1-ethyl-1-methylpropyl group, 1-ethyl-1-methylpentyl group, 1-hexyl-1-methylnonyl group, bicyclooctyl group, admantyl group.
• the total number of carbon atoms contained in Q1 and Q2 is 8 or more, and it is preferably to 10 to 32.
• Q3 represents a substituent
• a substituent preferable includes, for example, an aliphatic group, an aryl group, a halogen atom, a hydroxyl group, an amino group, a carbonamide group, a sulfonamido group, a ureido group, an acyloxy group, an aliphatic oxy group, an aliphatic thio group, an aryl thio group and a sulfamoylamino group.
• aliphatic group represented by Q in Formula 2 a straight-chained, branched or cyclicalkyl group having 1 to 30 carbon atoms and a substituted alkyl group are preferable and, especially, a substituted alkyl group having 2 to 30 carbon atoms is preferable.
• substituted or unsubstituted phenyl or naphthyl group is preferable.
• a substituted phenyl group having 6 to 30 carbon atoms is especially preferable.
• substituent of the substituted phenyl group for example, those groups mentioned as the substituent for the substituted alkyl group for Q can be mentioned,
• a five-member or six-member heterocyclic ring having therein at least one hetero atom selected from nitrogen, oxygen and sulfur, or a fused ring formed from the five-member or six-member heterocyclic ring and another aromatic ring or a heterocyclic ring is preferable, and these fused rings may be substituted by a substituent, such as those mentioned as the substituent for the substituted alkyl group represented by Q.
• an aliphatic group or an aryl group is more preferable.
• Q4 represents a straight-chain, branched or cyclicalkyl group such as those mentioned above as the examples of Q1
• Q5 represents a tertiary alkyl group having 4 to 20 carbon atoms such as tert-butyl group, tert-amyl group, 1,1,3,3-tetramethylbutyl group, 1-ethyl-1-methylpentyl group, 1-hexyl-1-methylnonyl group, bicyclooctyl group and adamantyl group or a five member or six-member cyclicalkyl group such as cyclohexyl group
• Q' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
• aryl group represented by R11 or R12 for example, a phenyl group and a naphthyl group can be mentioned.
• Preferable number of the substituent is preferable to be 1 to 5, provided that when there are two or more of substituents, they may be either same or different.
• Preferable substituent on R11 are a halogen atom, an alkylsulfonyl group and a cyano group.
• R12 is one represented by Formula B; wherein, J represents an oxygen atom or a sulfur atom; k represents an integer of 0 to 4; 1 represents zero or one, provided that when k is two or more, the plural number of R14, may be either same or different; R13 represents an alkylene group, R14 represents a substituent.
• substituent represented by R14 for example, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxy group, an acyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, an acyl group, an acylamino group, a sulfonamido group, a carbamoyl group and a sulfamoyl group.
• the elimination group represented X11 for example, a halogen atom, an aryloxy group, a carbamoyloxy group, a carbamoylmethoxy group, an acyloxy group, a sulfonamido group and a succinicimido group can be mentioned.
• R21, R22 and R23 independently represent a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group and, among these groups, the alkyl group is preferable.
• substituents mentioned above may have a substituent and such substituent includes, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an acylamino group, a sulfonamido group, an alkylthio group, an arylthio group, a halogen atom, a heterocyclic group, a sulfonyl group, a sulfinyl group, a phosphonyl group, an acyl group, a carbamoyl group, a sulfamoyl group, a cyano group, an alkoxy group, an aryloxy group, a heterocyclicoxy group, a siloxy group, an acyloxy group, a carbamoylalkoxy group, an amino group, an alkylamino group an imido group, a ureido group, a sulfamoylamino group, an al
• Compound I-1 can be synthesized according to the following scheme.
• Compound I-2 can be synthesized according to the following scheme.
• Compound II-6 can be synthesized according to the following scheme.
• Compound II-10 is synthesized according to the following scheme.
• the cyan dye-forming coupler represented by the above-mentioned Formula 1 or 2 is incorporated in at least one red-sensitive silver halide emulsion layer.
• the cyan dye-forming couplers represented by the formulae 1 and 6 or formulas 2 and 6 can be used in the optional proportion, however, preferably, within a molar ratio of 1/1 to 1/10.
• the cyan dye-forming couplers represented by the Formulae 1, 2 and 6 may be used in the quantity of 1x10 ⁇ 3 to 8x10 ⁇ 1 mol and, more preferably, 1x10 ⁇ to 8x10 ⁇ 1 mol per a mol of silver halide.
• Amount of the compound represented by the Formula A-1 is preferably 0.01 to 10 g and, more preferably, 0.1 to 3.0 g per one gram of the cyan dye-forming coupler represented by Formulas 1, 2 or 6. Moreover the compound represented by the Formula A-1 may be used either one kind or two or more kinds in combination.
• a high-speed rotary mixer such as a colloid mill or a ultra-sonic homogenizer
• this may be incorporated into the emulsion, either directly or after it being is set, cut and washed with water.
• the compound represented by Formulas 1, 2, 6 or A-1 may be incorporated in the silver halide emulsion layer either separately after separately dissolving in the high boiling-point solvent and dispersing in the above-mentioned method, or at a time. Furthermore, concerning the compounds represented by Formulas 1, 2, 6 or A-1 it is preferable that compounds are dissolved, and dispersed altogether and incorporated in the silver halide emulsion layer.
• silver halide emulsion used in the light-sensitive material of the present invention any kind of silver halide emulsion which is known in the art can optionally be employed.
• the emulsion may undergo a conventional chemical sensitization, and can be spectrally sensitized with a conventional sensitizing dye, to make the emulsion sensitive to any pre-designed spectral region.
• the silver halide emulsion can comprise one or more kinds of photographic additives such as an anti-foggant, a stabilizer, etc.
• photographic additives such as an anti-foggant, a stabilizer, etc.
• the binder for the emulsion it is preferable to use gelatin.
• the silver halide emulsion layer and other hydrophilic colloidal layer may be hardened and can comprise a plasticizer and a dispersion containing a polymer which is insoluble or sparsely soluble in water.
• a coupler is used in the silver halide emulsion layer of the color photographic light-sensitive material.
• a colored coupler having a function as a color compensator, a competing coupler, a compound which is, upon reaction with an oxidation product of a color developing agent capable of splitting off a photographically useful fragment such as a development accelerator, a bleach accelerator, a developing agent, a solvent for the silver halide, a color toning agent, a hardener, a fogging agent, an anti-foggant, a chemical sensitizer, a spectral sensitizer, a desensitizing agent.
• the support for example, paper laminated with a polymer such as polyethylene, a polyethyleneterephthalate film, a baryta paper and a cellullose triacetate may be used.
• a polymer such as polyethylene, a polyethyleneterephthalate film, a baryta paper and a cellullose triacetate
• color photographic process which is generally known in the art may be applied.
• the present invention can be applied to any type of silver halide light-sensitive materials known in the art, including negative-type color films, color papers and reversal-type color films.
• the amount of addition of the additive in the silver halide light-sensitive photographic material is given, unless defined otherwise, in terms of weight (g) a square meter of the light-sensitive material. Concerning the amount of silver halide and colloidal silver, they are expressed in terms of equivalent amount of silver.
• UV-1 UV Absorbent
• CC-1 Colored coupler
• CM-1 Colored coupler
• Ole-1 High boiling-point solvent
• Second Layer Intermediate Layer (IL-1)
• UV absorbent 0.01
• High boiling-point solvent Ole-1
• Twelfth Layer Second Protective Layer (PRO-2)
• Respective layers contain, in addition to those components mentioned above, a coating aid Su-2, a dispersion aid Su-3, gelatin hardeners H-1 and H-2, and anti foggants AF-1 and AF-2.
• Silver halide emulsions used in this example are as follows.
• Distribution of width(%) (standard deviation/average grain size) x 100
• Ammonium ferric(III) ethylenediaminetetracetic acid 100 g Diammonium ethylenediaminetetracetic acid 10.0 g Ammonium bromide 150.0 g Acetic acid 10 ml
• This solution has the same composition as "Bleach Solution A” except that 2.5 g of sodium hydrosulfite was added to a liter of the above-mentioned "Bleaching Solution A”.
• maximum absorption means the maximum absorption wavelength(nm) of a sample at a portion of which density measured with red light is 1.0, when it is processed with "processing A”.
• Density difference in Tables 1 and 2 represents numeral values of the 100-times-multiplied ratio of the maximum densities of the respective samples measured with red light between when it is processed with "processing A" and "Processing B".
• the term "storage preservation property before exposure” represents density differences in the fog in the red-sensitive layer of the samples, one of which is placed under atomospheric conditions at 55°C and 65% R.H. for three days and, thereafter subjected to exposure and developing process with "Processing A” and another which does not undergo such experiment.
• the samples containing the cyan dye-forming coupler according to the present invention have enhanced sensitivity, favorable maximum absorption wavelength, reduced density difference even when it is processed with a fatigue bleaching solution and improved storage preservation property before exposure.
• Sample 2-1 was prepared in the same manner as in Sample 1 of Example 1, except for the following items 1 through 3.
• Samples 2-2 through 2-5 were prepared in the same manner as in Sample 2-1, except that the coupler C-B employed in 3rd and 4th layers of Sample 1 was replaced with the same mols of the coupler shown in Table 3, respectively.
• Comparative Sample 2-1 in which Comparative dye-forming coupler C-B and high boiling-point solvent Oil-1 are used, have good optical absorption, however, density change in the processing with the fatigue bleaching solution and fogging in the storage before exposure are large.

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Citations (42)

• 1995
  • 1995-06-29 EP EP95304580A patent/EP0690344A1/de not_active Withdrawn

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