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(11) | EP 0 690 344 A1 |
| (12) | EUROPEAN PATENT APPLICATION |
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| (54) | Silver halide color photographic light-sensitive material |
| (57) A silver halide color photographic light-sensitive material comprising a support
and provided thereon, a blue-sensitive, a green-sensitive and a red-sensitive silver
halide emulsion layer, wherein at least one of said red-sensitive silver halide emulsion
layer comprises at least one compound represented by Formula 1 or Formula 2:
wherein R₁ and R₂ independently, and Q₁ and Q₂ independently represent an aliphatic group, provided that the total number of carbon atoms contained in R₁ and R₂ and in Q₁ and Q₂ is 8 or more; R₃ and Q₃ independently represent a substituent; n and m are each 0 or 1 and R and Q independently an aliphatic group, and aryl group or a heterocyclic group. |
Field of the Invention
[0001] 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.
Background of the Invention
[0002] Heretofore, 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.
[0003] In this photographic process, color reproduction by subtractive color system is generally employed and yellow, magenta and cyan dye images are produced.
[0004] As for cyan dye-forming coupler, 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.
[0005] Heretofore, naphthol type compounds, of which second-position is substituted by a carbamoyl group have been used. However, there has been a problem that color density tends to be reduced when this type of cyan dye is processed with a fatigued bleach solution.
[0006] On the other hand, 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.
[0007] For the purpose of improving the above-mentioned disadvantages, 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. Recently, although there have been a demand for a silver halide color photographic material having high sensitivity, the color forming property of the above-mentioned cyan couplers are not sufficient. Furthermore, 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.
Summary of the Invention
[0008] 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.
[0009] 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
[0010] 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.
[0011] The fourth object of the present invention is to provide a silver halide light-sensitive color photographic material having improved storage stability before exposure.
[0012] The above-mentioned objects of the present invention have been attained by the following items.
Item 1: A silver halide color photographic light-sensitive material comprising a support
and provided thereon, a blue-sensitive silver halide emulsion layer, a green-sensitive
silver halide emulsion layer and a red-sensitive silver halide emulsion layer, wherein
said red-sensitive silver halide emulsion layer comprises a compound represented by
Formula 1 or Formula 2:
wherein R₁ and R₂ independently represent an aliphatic group, provided that the
total number of carbon atoms contained in R₁ and R₂ is 8 or more; R₃ represents a
substituent; n is 0 or 1 and R represents an aliphatic group, an aryl group or a heterocyclic
group;
wherein Q₁ and Q₂ independently represent an aliphatic group, provided that the
total number of carbon atoms contained in Q₁ and Q₂ is 8 or more; Q₃ represents a
substituent; m represents 0 or 1; Q represents an aliphatic group, an aryl group or
a heterocyclic group.
Item 2: The silver halide color photographic light-sensitive material of item 1, wherein
said red-sensitive silver halide emulsion layer further comprises a compound represented
by Formula 6:
wherein R₁₁ represents an aryl group or a heterocyclic group; R₁₂ represents an
alkyl group or an aryl group, provided that R₁₂ may form a group capable of forming
a dimer or an oligomer with R₁₁ or R₁₂; X₁₁ represents a hydrogen atom or a group
capable of splitting off upon reaction with an oxidation product of a color developing
agent.
Item 3: The silver halide color photographic light-sensitive material of item 1, wherein
said red-sensitive silver halide emulsion layer further comprises a compound represented
by Formula A-1:
wherein R₂₁, R₂₂ and R₂₃ independently represent a hydrogen atom, an alkyl group,
a cycloalkyl group or an aryl group.
Item 4: The silver halide color photographic light-sensitive material of item 1, wherein
said -O-Q of said Formula 2 represents an aliphaticoxy group, a heterocyclicoxy group
or a
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl
group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl
group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl
group, m is an integer of 0 to 1; RB represents a hydrogen atom, an alkyl group, an
alkoxyl group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, a
nitro group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl
group, an arylsulfonyl group, a formyl group, an acylamino group, an aryloxycarbonyl
group, n is an integer of 0 to 1.
Item 5: The silver halide color photographic light-sensitive material of item 1, wherein
the compound represented by said Formula 1 is represented 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
R₇ 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.
Item 6: The silver halide color photographic light-sensitive material of item 1, wherein
the compound represented by Formula 2 is represented by Formula 4:
wherein Q₄ represents a straight-chain, branched or cyclic alkyl group; Q₅ represents
a tertiary alkyl group having 4 to 20 carbon atoms or a five member or six-member
cyclic alkyl group; Q' represents a substituted alkyl group having 2 to 30 carbon
atoms or a substituted phenyl group having 6 to 30 carbon atoms.
Item 7: The silver halide color photographic light-sensitive material of item 6, wherein
said -O-Q' of said Formula 4 represents an aliphaticoxy group, a heterocyclicoxy group
or a
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl
group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl
group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl
group, m is an integer of 0 to 1; RB represents an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylamino
group, an arylamino group, a nitro group, a hydroxyalkyl group, a carbamoyl group,
a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an
acylamino group, an aryloxycarbonyl group, n is an integer of 0 to 1.
Item 8: The silver halide color photographic light-sensitive material of item 2, wherein the compound represented by Formula 1 or Formula 2 and the compound represented by Formula 6 are contained in a molar ratio of 1:1 to 1:10.
Item 9. The silver halide color photographic light-sensitive material of item 1, wherein said compound represented by Formula 1 or Formula 2 is contained in an amount of 1 × 10⁻³ mol to 8 × 10⁻¹mol per mol of silver halide.
Item 10: The silver halide color photographic light-sensitive material of item 1, wherein said compound represented by Formula 1 or Formula 2 is contained in an amount of 1 × 10⁻ mol to 8 × 10⁻¹mol per mol of silver halide.
[0013] Herein below, the cyan dye-forming coupler represented by Formula 1 will be described in detail.
[0014] As for the aliphatic group represented by 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.
[0015] 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.
[0016] 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.
[0017] 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.
[0018] As for the 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. As for the substituent for the substituted alkyl group, for example, a carboxyl group, an aliphaticoxy carbonyl group, an aliphatic oxy group, an aryl oxy group, an aliphatic thio group, an aryl thio group, a sulfonyl group, an acyl group, a carbamoyl group, a sulfamoyl group, an acylamino group, a sulfonamido group, a halogen atom, a ureido group, a urethane group, an acyloxy group, a cabamoyloxy group, a hydroxyl group, an aryl-group, a heterocyclic group, a cyano group, a nitro group, an amino group, an oxalyl group and an oxamide group can be mentioned.
[0019] As for the aryl group for R, substituted or unsubstituted phenyl or naphthyl group is preferable. And, a substituted phenyl group having 6 to 30 carbon atoms is especially preferable. As for the substituent of the substituted phenyl group, for example, those groups mentioned as the substituent for the substituted alkyl group for R can be mentioned.
[0020] As for the heterocyclic group for R, 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.
[0021] As R, an aliphatic group or an aryl group is preferable. Among 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.
[0022] As for the example of the 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.
[0024] 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. As for the aliphatic group represented by Q₁, 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. As for the aliphatic group represented by Q₂, 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.
[0025] Q₃ represents a substituent, and 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.
[0026] As for the 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. As for the substituent for the substituted alkyl group, for example, a carboxyl group, an aliphaticoxycarbonyl group, an aliphaticoxy group, an aryloxy group, an aliphaticthio group, an arylthio group, a sulfonyl group, an acyl group, a carbamoyl group, a sulfamoyl group, an acylamino group, a sulfonamido group, a halogen atom, a ureido group, a urethane group, an acyloxy group, a cabamoyloxy group, a hydroxyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, an amino group, an oxalyl group and an oxamide group can be mentioned.
[0027] As for the aryl group for Q, substituted or unsubstituted phenyl or naphthyl group is preferable. And, a substituted phenyl group having 6 to 30 carbon atoms is especially preferable. As for the substituent of the substituted phenyl group, for example, those groups mentioned as the substituent for the substituted alkyl group for Q can be mentioned,
[0028] As for the heterocyclic group for Q, 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.
[0030] Among compounds represented by Formula 2, especially preferable example, one represented by Formula 4 can be mentioned:
wherein 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.
[0031] As for the examples of the substituent for the substituted alkyl group or the substituted phenyl group represented by Q', those groups mentioned above as the substituent for the substituted alkyl group in the aliphatic group represented by Q in Formula 2 can be mentioned.
[0032] Hereunder, compounds represented by the above-mentioned Formulae 6 and A-1 will be described in detail.
[0033] As for the aryl group represented by R₁₁ or R₁₂, for example, a phenyl group and a naphthyl group can be mentioned.
[0034] As for the substituent for the groups represented by R₁₁ or R₁₂, for example, a halogen atom, a nitro group, a cyano group, an alkyl group, an aryl group, an amino group, a hydroxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxysulfonyl group, an aryloxysulfonyl group, a carbamoyl group, a sulfamoyl group, an acyloxy group, a carbonamido group and sulfonamido group can be mentioned.
[0035] 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.
[0037] Preferable group as 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. As for the 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.
[0038] As for 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.
[0039] As for the more specific examples, those disclosed in U.S. Patent Nos.3,476,563 and 3,749,735; Japanese Patent Publication O.P.I. Publication No.47-37425(1972), Japanese Patent Publication No. 48-36894(1973); Japanese Patent O.P.I. Publication Nos.50-10135(1975), 50-117422(1975), 50-130441(1975), 51-108841(1976), 50-120334(1975), 52-18315(1977) and 53-105226(1978), can be mentioned.
[0040] 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.
[0041] Those groups 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 alkoxycarbonylamino group, an aryloxycarbonylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group and a carboxy group can be mentioned.
[0043] Hereinbelow, representative examples represented by the above-mentioned Formulae 6 and A-1 are shown, however, the scope of the present invention shall not be limited by them.
[0044] As for other specific examples of the phenol-type coupler having a ureido group, than those given above, for example, those disclosed in Japanese Patent O.P.I. Publication Nos.56-65134(1981), 57-204543(1982), 57-204544(1982), 57-204545(1982). 58-33249(1983), 58-33253(1983), 58-98731(1983), 58-118643(1983), 58-179838(1983), 58-187928(1983), 59-65844(1984), 59-71051(1984), 59-86048(1984), 59-105644(1984), 59-111643(1984), 59-111644(1984), 59-131939(1984), 59-165058(1984), 59-177558(1984), 59-180559(1984), 59-198455(1984), 60-35731(1985), 60-37557(1985), 60-49335(1985), 60-49336(1985), 60-50533(1985), 60-91355(1985), 60-107649(2984), 60-107650(1985) and 61-2757(1986) can be mentioned.
[0045] Herein below, synthetic examples of the cyan dye-forming coupler represented by Formula 1 are given.
Synthesis Example 1-1(Synthesis of Compound I-1)
[0047] 22 g of p-hydroquinone and 77 g of 2-ethylhexyl bromide were dissolved in 150 ml of ethanol. Next, 300 ml of ethanol solution, in which 29 g of potassium hydroxide was dissolved, was added and underwent reaction for ten hours under reflux. After filtrating off the precipitated potassium bromide the solution was condensed and extracted the reaction product by adding ethyl acetate and water, to collect an organic phase. After condensing this 40.5 g of 1,4-di-(2-ethylhexyloxy)benzene(A) in the form of a colorless oil(), was obtained by vacuum distillation ( a temperature range of 200 to 203 °C, a pressure condition is 3 mmHg).
[0048] 80 ml of chloroform was added to 27 g of (A), and to this 10 g of 65% nitric acid was added dropwise while cooling down the solution at 0 to 3°C. While maintaining cooling, the solution was stirred for one hour and, then, water was added to wash an organic phase. After washing with 5% sodium hydrogencarbonate and water, the organic phase was condensed and dried, to obtain 30.6 g of 2,5-di-(2-ethylhexyloxy)nitrobenzene(B) in the form of a yellowish oil. This was used in the next step without refinement.
[0049] 29 g of (B) was dissolved in 30 ml of methanol and 120 ml of ethyl acetate and, to this 3 g of 5% wet Pd/C catalyst was added to underwent catalytic hydrogenation for ten hours under ordinary temperature and ordinary pressure. After completion of the reaction, the catalyst was filtered out and, by condensing and drying the filtered solution, 26 g of 2,5-di-(2-ethylhexyloxy)aniline(C) in the form of a thin-brownish oil was obtained. This was used in the next step without refinement.
[0050] 250 g of 1,4-dihydroxy-2-naphthoic acid was added to 1.9 1 of N,N-dimethylformamide and, to this, an aqueous alkaline solution consisting of 103 g of sodium hydroxide and 154 ml of water was added, under nitrogen gas flow. While maintaining the inner temperature at 30°C, 172 g of 1-fluoro-4-nitrobenzene was added taking 10 minutes and stirred for two hours at the inner temperature of 45°C. The mixture was, then poured into 1.5 Kg of ice and 250 ml of concentrated hydrochloric acid, and then, solidified crude crystals were filtrated. This was further recrystallized in acetonitrile, to obtain 315 g of 1-hydroxy-4-(4-nitrophenoxy)-2-naphthoic acid (D) in the form of pale yellowish crystals
[0051] 250 g of (D) and 87 g of phenol were added to 1.5 liter of chloroform and, then, after 119 g of phosphorous oxychloride was added dropwise, temperature was raised up to reflux temperature and, then under reflux 250 ml of N,N-dimethylformamide was added drowise taking about two hours and the mixture was further stirred for five hours under reflux. After leaving the reaction mixture overnight, it was condensed until the volume of the reaction mixture became about 700 ml and then 21 of methanol was added to this, precipitated crystal were filtrated to obtain 235 g of 1-hydroxy-4-(4-nitrophenoxy)-2-naphthoic acid phenyl (E) in the form of pale yellowish needle crystals.
[0052] 21 g of (E) and 20 g of (c) were added to 100 ml of mesitylene and the mixture was stirred for two hours at the inner temperature at 150 to 160°C. After completion of the reaction, while maintaining heating mesitylene and phenol were distilled out under reduced pressure. After cooling down the reaction mixture to 50 to 60°C, 100 ml of 2: 1 mixed solution of ethyl acetate and methanol was added and after cooling with ice, precipitated crystal were filtrated, to obtain 20 g of 1-hydroxy-4-(4-nitrophenoxy)-N-[2,5-di-(2-ethylhexyloxy)phenyl]-2-naphthamide(F) in the form of pale yellow crystals.
[0053] 17 g of (F) was dissolved in 170 ml of ethylacetate ,to this 3 g of 5% wet Pd/C catalyst was added to undergo catalytic hydrogenation for seven hours under room temperature and atmospheric pressure. After completion of the reaction, the catalyst was filtrated and, by condensing and drying the filtered solution, 16 g of 1-hydroxy-4-(4-aminophenoxy)-N-[2,5-di-(2-ethylhexyloxy)phenyl]-2-naphthamide(G) was obtained in the form of brownish oil.
[0054] 4 g of (G) and 0.7 g of succinic acid anhydride were added and dissolved in 40 ml of ethyl acetate, and under reflux the solution was stirred for one hour. After completion of the reaction, water was added and extracted with ethyl acetate and the collected organic phase was condensed after washing. By refining the crude product was refined by the use of silica gel chromatography(n-hexane-ethyl acetate eluate).
[0056] Result of Elementary Analysis
Formula: C₄₃H₅₄N₂O₈
| C(%) | H(%) | N(%) | |
| Calculation: | 71.05 | 7.49 | 3.85 |
| Experimental | 71.02 | 7.53 | 3.83 |
Synthesis Example: 1-2 (Synthesis of Compound I-2)
[0058] 53 g of 1,4-di-hydroxy-2-naphthoic acid was dissolved in one liter of N,N-dimethylformamide and thereto an aqueous alkaline solution consisting of 22 g of sodium hydroxide and 33 g of water was added dropwise under nitrogen gas flow. After stirring for 30 minutes, a solution consisting of 51 g of N-(2-methoxyethyl)-2-bromoacetamide and 200 ml of N,N-dimethylformamide were added dropwise and reacted for four hours under inner temperature condition at 42 to 44°C. Then this was poured into 400 g of ice and 85 ml of water and precipitated crystals were taken by filtration. Further, by recrystalizing with acetonitrile, 61 g of 1-hydroxy-4-(2-methoxyethylcarbamoylmethoxy)-2-naphthoic acid(H) was obtained in the form of pale greenish cotton-like crystals.
[0059] 3 g of (H) and 3.3 g of (C), which was synthesized in I-1 above, were dissolved in 70 ml of warmed dioxane and, thereto, a solution consisting of 2.1 g of 1,3-dicyclohexylcarbodimide and 20 ml of dioxane was added. Agitate the solution for one hour under inner temperature at 50°C and, after precipitated 1,3-dicylohexylurea by filtration was separated, the filtered solution was condensed. By refining the obtained reaction mixture by silica gel column chromatography(with n-hexaneethyl acetate type eluate), 3.8 g of Compound I-2 was obtained in the form of white crystals.
[0060] Result of Elementary Analysis
Formula: C₃₈H₅₄N₂O₇
| C(%) | O(%) | N(%) | |
| Calculation: | 70.13 | 8.36 | 4.30 |
| Experiment: | 70.12 | 8.39 | 4.32 |
[0061] Synthesis examples of the cyan dye-forming coupler represented by Formula 2 of the present invention are illustrated below:
Synthesis Example: 2-1 (Synthesis of Compound II-6)
[0063] 20 g of 4-(1,1,3,3-tetramethylbutyl)phenol was dissolved in 100 ml of N,N-dimethylformamide and after 15 g of isobutyl bromide to this, 18 g of potassium carbonate(K2C03) was added and stirred for eight hours under inner temperature at 80°C. After completion of the reaction, water was added to the reaction mixture, extracted with ethyl acetate and the organic phase washed with a saturated aqueous sodium chloride solution. Condensing and drying the product and then by refining it by silica gel column chromatography, to obtain 18 g of 4- isobutyloxy-(1,1,3,3-tetramethylbutyl)benzene (I) in the form of colorless oil.
[0064] 8 g of (I) was dissolved in 50 ml Of chloroform and to this 5.5 ml of 61% nitric acid was added dropwise. This was stirred for two hours under inner temperature at 40°C. After completion of the reaction, water was added to separate the organic phase and washed with water. Condensing and drying the organic phase and, then, by refining it by silica gel column chromatography with n-hexane-ethyl acetate eluate, to obtain 9 g of 2-isobutyloxy-5-(1,1,3,3-tetramethylbutyl)nitrobenzene (J) in the form of yellowish oil.
[0065] 8 g of (J) was dissolved in 50 ml of methanol and , to this, 1 g of 5% wet Pd/C catalyst was added, to undergo contact hydrogenation for three hours under room temperature and atmosheric pressure. After completion of the reaction, the catalyst was filtrated out and the filtered solution was condensed and dried to obtain 7 g of 2-isobutyloxy-5-(1,1,3,3-tetramethylbutyl)aniline (K) in the form of brownish oil.
[0066] 4 g of (E)(cf. Synthesis Example I-1) and 3 g of (K) were added into 20 ml of mesitylene and this was stirred for three hours under inner temperature at 150 to 160°C. After completion of the reaction and, while keeping heating, mesitylene and phenol were distilled off. After cooling down the reaction mixture to 50 - 60°C, 30 ml of 2:1 mixed solvent of ethyl acetate and methanol was added. After cooling down the reaction mixture with ice, precipitated crystals were filtered and 4.8 g of 1-hydroxy-4-(4-nitrophenoxy)-N-[2-isobutyloxy-5-(1,1.3,3-tetramethylbutyl)phenyl]-2-naphthamide (L) was obtained in the form of pale yellowish crystals.
[0067] 4 g of (L) was dissolved in 50 ml of ethyl acetate and , to this, 0.5 g of 5% wet Pd/C catalyst was added, to undergo contact hydrogenation for eight hours under room temperature and atmospheric pressure. After completion of the reaction the catalyst was filtrated out and the filtered solution was condensed and dried to obtain 3.8 g of 1-hydroxy-4-(4-aminophenoxy)-N-[2-isobutyloxy-5-(1,1,3,3-tetramethylbutyl)phenyl]-2-naphthoamide (M) in the form of pale brownish solid.
[0068] 3 g of (M) and 0.6 g of succinic acid anhydride were added to 30 ml of ethyl acetate and stirred under reflux for one and half hours. After completion of the reaction water was added and extracted with ethyl acetate. After washing with water the collected organic phase was condensed by refining the crude product, by silica gel column chromatography with n-hexane-ethyl acetate type eluate, 2.1 g Compound II-6 was obtained in the form of white crystals.
[0069] Result of Elementary Analysis:
Chemical Formula: C₃₉H₄₆N₂O₇
| C(%) | H (%) | N(%) | |
| Calculation: | 71.54 | 7.08 | 4.28 |
| Experiment: | 71.51 | 7.10 | 4.27 |
Synthesis Example 2-2(Synthesis of Compound II-10)
[0071] 3 g of (H) and 2.7 g of (K)(cf. Synthesis Example 2-1 above) were dissolved in 70 ml of dioxane and, to this, 2.1 g of 1,3-dicyclohexylcarbodiimide and 20 ml of dioxane were added. The solution was stirred at inner temperature of 50 °C for one and a half hours. After filtrating off the precipitated 1,3-dicyclohexylurea, the reaction mixture solution was filtered and the filtered solution was condensed, and the crude product was obtained. The crude product was refined by silica gel column chromatography with n-hexaneethyl acetate type eluate, 3.2 g of Compound II-10 was obtained in the form of white crystals.
[0072] Result of Elementary Analysis:
Chemical Formula: C₃₄H₄₆N₂O₆
| C(%) | H (%) | N(%) | |
| Calculation: | 70.56 | 8.01 | 4.84 |
| Experiment: | 70.54 | 8.04 | 4.83 |
[0073] In the present invention, 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.
[0074] 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.
[0075] 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.
[0076] In order to incorporate compound represented by Formulas 1, 2, 6 or A-1 used in the present invention in a silver halide emulsion layer, it is possible to apply a method, in which the above-mentioned compound or compoundes are first dissolved in a conventionally known high boiling-point solvent, such as dibutyl phthalate, tricresyl phosphate or combination of the high boiling-point solvent and a low boiling-point solvent such as butyl acetate, ethyl acetate, either singly or in combination, respectively. Then the coupler solution is mixed with an aqueous solution containing gelatin and a surface active agent. Subsequently, after the solution is subject to emulsification, using 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.
[0077] 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.
[0078] As for 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.
[0079] 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.
[0080] The silver halide emulsion can comprise one or more kinds of photographic additives such as an anti-foggant, a stabilizer, etc. As for the binder for the emulsion, it is preferable to use gelatin.
[0081] 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.
[0082] It is also possible to use 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.
[0083] As for 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.
[0084] In order to obtain a dye image using the light-sensitive material of the present invention, color photographic process which is generally known in the art may be applied.
[0085] 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.
Examples
[0086] Hereinbelow the present invention is further explained with reference to working examples, however, the scope of the present invention is not limited by them.
[0087] In all of the following examples, 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.
Example 1
[0088] On a triacetylcellullose film support, respective layers, the components of which are given below, are provided in order to prepare a multi-layer silver halide light-sensitive color photographic material (Sample No.1).
First Layer: Anti-Halation Layer (HC-1)
[0089]
| Black colloidal silver | 0.20 |
| UV Absorbent (UV-1) | 0.20 |
| Colored coupler (CC-1) | 0.05 |
| Colored coupler (CM-1) | 0.05 |
| High boiling-point solvent (Oil-1) | 0.20 |
| Gelatin | 1.5 |
Second Layer: Intermediate Layer (IL-1)
Third Layer: Low red light-sensitive silver halide emulsion layer (RL)
Fourth Layer: High red light-sensitive silver halide emulsion layer (RH)
Fifth Layer: Intermediate Layer (IL-2)
Sixth Layer: Low green light-sensitive silver halide emulsion layer (GL)
Seventh Layer: High green light-sensitive silver halide emulsion layer (GH)
Eighth Layer: Yellow Filter Layer (YC)
[0096]
| Yellow colloidal silver | 0.1 |
| Anti-dye staining agent (SC-1) | 0.1 |
| High boiling-point organic solvent (Oil-3) | 0.1 |
| Gelatin | 0.8 |
Ninth Layer: Low blue light-sensitive silver halide emulsion layer (BL)
Tenth Layer: High blue light-sensitive silver halide emulsion layer (BH)
Eleventh Layer: First protective layer (PRO-1)
Twelfth Layer: Second Protective Layer (PRO-2)
[0100]
| Surface active agent (Su-1) | 0.005 |
| Alkali-soluble matting agent (Average grain size: 2 µm) | 0.05 |
| Polymethylmethacrylate (Average grain diameter: 3 µm) | 0.05 |
| Lubricant (WAX-1) | 0.04 |
| Gelatin | 0.6 |
[0101] 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.
[0102] Silver halide emulsions used in this example are as follows.
Em-1: an emulsion containing core/shell-type mono-disperse silver halide grains, of which average grain size, average silver iodide content and dispersion of width are 0.46 µm, 7.0 mol% and 14%, respectively.
Em-2: an emulsion containing core/shell-type mono-disperse silver halide grains, of which average grain size, average silver iodide content and dispersion of width are 0.30 µm, 2.0 mol% and 14%, respectively.
Em-3: an emulsion containing core/shell-type mono-disperse silver halide grains, of which average grain size, average silver iodide content and dispersion of width are 0.81 µm, 7.0 mol% and 14%, respectively.
Em-4: an emulsion containing core/shell-type mono-disperse silver halide grains, of which average grain size, average silver iodide content and dispersion of width are 0.95 µm, 8.0 mol% and 14%, respectively.
[0103] In the above, distribution of width is expressed in the following equation:
H-1
H-2
[(CH₂=CHSO₂CH₂)₃CCH₂SO₂(CH₂)₂]₂N(CH₂)₂SO₃K
[0104] Next, in Sample No.1 above, cyan dye-forming couplers C-A and C-B, which are incorporated in the third and the fourth silver halide emulsion layers, were replaced by equivalent molar amount of Comparative couplers RC-1, RC-2 and RC-3 and the cyan dye-forming couplers according to the present invention as shown in Table-1.
[0105] Thus prepared samples were subjected to exposure with white light for 1/100 second through an optical wedge and, thereafter processed according to 'Processing A" and "Processing B"
Processing Steps (at 38°C)
[0106]
| Processing Step | Time |
| Color Development | 3'15'' |
| Bleaching | 6'30'' |
| Washing | 3'15'' |
| Fixing | 6'30'' |
| Washing | 3'15'' |
| Stabilizing | 1'30'' |
| Drying |
[0107] Ingredients of the processing solutions used in the respective processes are as follows; provided that in "Processing A", "Bleaching Solution A" and in "Processing B", "Bleaching Solution B" were used, respectively.
<Color Developing Solution>
<Bleaching Solution A>
[0110]
| Ammonium ferric(III) ethylenediaminetetracetic acid | 100 g |
| Diammonium ethylenediaminetetracetic acid | 10.0 g |
| Ammonium bromide | 150.0 g |
| Acetic acid | 10 ml |
[0111] Add water to make the total volume 1 liter and adjusted pH of the solution at 6.0 with ammonia water.
<Bleaching Solution B>
[0112] 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".
<Fixing Solution>
[0114] Add water to make the total volume one liter and adjusted pH of the solution at 6.0 with acetic acid
<Stabilizing Solution>
[0117] With respect to the thus obtained dye images produced in Samples 1 through 30 according to the above-mentioned color developing steps, sensitivities of the red-sensitive layer of the Samples were measured using an optical densitometer type PDA-65, a product of Konica Corporation. The sensitivity was obtained in terms of a reciprocal of exposure necessary to give the minimum density plus 0.1 and expressed as relative values as shown in Table 1, in which sensitivity of Sample 1 was normalized as 100.
[0118] The term "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".
[0119] The term "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".
[0120] 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.
[0122] As obvious from Tables 1 and 2, it is understood that 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.
Example 2
[0123] Sample 2-1 was prepared in the same manner as in Sample 1 of Example 1, except for the following items 1 through 3.
Item 1: 1.0 (g) of Cyan dye forming coupler (C-A) employed in 3rd layer of Sample 1 is replaced with 0.7 (g) of Cyan dye forming coupler (C-B).
Item 2: 0.25 (g) of Cyan dye forming coupler (C-A) and 0.05 (g) of Cyan dye forming coupler (C-B) employed in Sample 1 were replaced with 0.20 of Cyan dye forming coupler (C-B).
Item 3: DIR compound (D-2) employed in 9th layer of Sample 1 was replaced with DIR compound (D-2A).
[0124] 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.
[0125] The above-mentioned Samples 2-1 through 2-5 were evaluated by the same method disclosed on pages 51 and 52.
[0126] As obvious from the results shown in Table 3, it is understood that Samples No.2-2 through 2-5, which are according to the present invention, have enhanced sensitivity, excellent processing stability without shift of the absorption wavelength in the high density portion of the image and improved storage preservation property before exposure.
[0127] On the other hand, 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.
1. A silver halide color photographic light-sensitive material comprising a support and
provided thereon, a blue-sensitive silver halide emulsion layer, a green-sensitive
silver halide emulsion layer and a red-sensitive silver halide emulsion layer, wherein
said red-sensitive silver halide emulsion layer comprises a compound represented by
Formula 1 or Formula 2:
wherein R₁ and R₂ independently represent an aliphatic group, provided that the total number of carbon atoms contained in R₁ and R₂ is 8 or more; R₃ represents a substituent; n is 0 or 1 and R represents an aliphatic group, an aryl group or a heterocyclic group;
wherein Q₁ and Q₂ independently represent an aliphatic group, provided that the total number of carbon atoms contained in Q₁ and Q₂ is 8 or more; Q₃ represents a substituent; m represents 0 or 1; Q represents an aliphatic group, an aryl group or a heterocyclic group.
wherein R₁ and R₂ independently represent an aliphatic group, provided that the total number of carbon atoms contained in R₁ and R₂ is 8 or more; R₃ represents a substituent; n is 0 or 1 and R represents an aliphatic group, an aryl group or a heterocyclic group;
wherein Q₁ and Q₂ independently represent an aliphatic group, provided that the total number of carbon atoms contained in Q₁ and Q₂ is 8 or more; Q₃ represents a substituent; m represents 0 or 1; Q represents an aliphatic group, an aryl group or a heterocyclic group.
2. The silver halide color photographic light-sensitive material of claim 1, wherein
said red-sensitive silver halide emulsion layer further comprises a compound represented
by Formula 6:
wherein R₁₁ represents an aryl group or a heterocyclic group; R₁₂ represents an alkyl group or an aryl group, provided that R₁₂ may form a group capable of forming a dimer or an oligomer with R₁₁ or R₁₂; X₁₁ represents a hydrogen atom or a group capable of splitting off upon reaction with an oxidation product of a color developing agent.
wherein R₁₁ represents an aryl group or a heterocyclic group; R₁₂ represents an alkyl group or an aryl group, provided that R₁₂ may form a group capable of forming a dimer or an oligomer with R₁₁ or R₁₂; X₁₁ represents a hydrogen atom or a group capable of splitting off upon reaction with an oxidation product of a color developing agent.
3. The silver halide color photographic light-sensitive material of claim 1, wherein
said red-sensitive silver halide emulsion layer further comprises a compound represented
by Formula A-1:
wherein R₂₁, R₂₂ and R₂₃ independently represent a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group.
wherein R₂₁, R₂₂ and R₂₃ independently represent a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group.
4. The silver halide color photographic light-sensitive material of claim 1, wherein
said -O-Q of said Formula 2 represents an aliphaticoxy group, a heterocyclicoxy group
or a
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, m is an integer of 0 to 1; RB represents a hydrogen atom, an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, a nitro group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an aryloxycarbonyl group, n is an integer of 0 to 1.
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, m is an integer of 0 to 1; RB represents a hydrogen atom, an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, a nitro group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an aryloxycarbonyl group, n is an integer of 0 to 1.
5. The silver halide color photographic light-sensitive material of claim 1, wherein
the compound represented by said Formula 1 is represented 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 R₇ 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.
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 R₇ 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.
6. The silver halide color photographic light-sensitive material of claim 1, wherein
the compound represented by Formula 2 is represented by Formula 4:
wherein Q₄ represents a straight-chain, branched or cyclic alkyl group; Q₅ represents a tertiary alkyl group having 4 to 20 carbon atoms or a five member or six-member cyclic alkyl group; Q' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
wherein Q₄ represents a straight-chain, branched or cyclic alkyl group; Q₅ represents a tertiary alkyl group having 4 to 20 carbon atoms or a five member or six-member cyclic alkyl group; Q' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
7. The silver halide color photographic light-sensitive material of claim 6, wherein
said -O-Q' of said Formula 4 represents an aliphaticoxy group, a heterocyclicoxy group
or a
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, m is an integer of 0 to 1; RB represents an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, a nitro group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an aryloxycarbonyl group, n is an integer of 0 to 1.
wherein RA represents an alkyl group, a nitro group, an amino group, an alkoxyl group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, m is an integer of 0 to 1; RB represents an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, a nitro group, a hydroxyalkyl group, a carbamoyl group, a carboxyl group, an alkylsulfonyl group, an arylsulfonyl group, a formyl group, an acylamino group, an aryloxycarbonyl group, n is an integer of 0 to 1.
8. The silver halide color photographic light-sensitive material of claim 2, wherein
the compound represented by Formula 1 or Formula 2 and the compound represented by
Formula 6 are contained in a molar ratio of 1:1 to 1:10.
9. The silver halide color photographic light-sensitive material of claim 1, wherein
said compound represented by Formula 1 or Formula 2 is contained in an amount of 1
× 10⁻³ mol to 8 × 10⁻¹mol per mol of silver halide.
10. The silver halide color photographic light-sensitive material of claim 1, wherein
said compound represented by Formula 1 or Formula 2 is contained in an amount of 1
× 10⁻ mol to 8 × 10⁻¹mol per mol of silver halide.