JP2935149B2 - Silver halide photographic material - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silver halide photographic light-sensitive material, and more particularly, to a silver halide photographic light-sensitive material capable of stably forming a high-sensitivity, super-hard, negative image used in a photomechanical process. It is about.

[0002]

BACKGROUND OF THE INVENTION The addition of hydrazine compounds to silver halide photographic emulsions and developers is disclosed in U.S. Pat.
No. 727 (developing solution combining ascorbic acid and hydrazine) and 3,227,552 (hydrazine is used as an auxiliary developing agent for directly obtaining a positive color image), 3,386,831 (Containing β-monophenylhydrazide of an aliphatic carboxylic acid as a stabilizer for silver halide light-sensitive materials), 2,419,975, and Mees, "The Theory of Photographic process"
Third edition (1966), page 281 and the like.

[0003] Among them, in particular, US Patent No. 2,41
No. 9,975 discloses that a high contrast negative image is obtained by adding a hydrazine compound. That is, when a hydrazine compound is added to a silver chlorobromide emulsion and developed with a developer having a high pH such as 12.8, extremely hard photographic characteristics having a gamma (γ) exceeding 10 can be obtained.
Are listed.

However, a strong alkaline developer having a pH close to 13 is easily oxidized by air, is unstable, and cannot withstand long-term storage or use. The super-hard photographic characteristics with a gamma value exceeding 10 can be applied to the reproduction of continuous tone images using dot images useful for printing plate making or the reproduction of line drawings, regardless of whether they are negative images or positive images. Useful.

[0005] For this purpose, a silver chlorobromide emulsion having a silver chloride content of more than 50 mol%, preferably more than 75 mol%, has been conventionally used, and the effective concentration of sulfite ions has been extremely low (usually). (0.1 mol / l or less) was generally used (lith development).

[0006] However, in this method, the developer is extremely unstable due to low sulfite ions in the developer and cannot withstand storage for more than three days. Furthermore, all of these methods required the use of a silver chlorobromide emulsion having a relatively high silver chloride content, so that high sensitivity could not be obtained.

Accordingly, there has been a strong demand for obtaining ultra-high contrast photographic characteristics useful for reproducing halftone images and line drawings by using a high-sensitivity emulsion and a stable developer.

For this purpose, US Pat.
977, 4,224,401, 4,243,7
Nos. 39, 4,269,929 and 4,272,61
Nos. 4 and 4,323,643 and the like, a surface latent image type silver halide photographic light-sensitive material to which a specific acylhydrazine compound is added is used. There has been proposed a system for forming an extremely hard negative image by processing with a developer containing 15 mol / l or more and having good storage stability. This new image forming system is characterized in that conventional lithographic development can use only silver chlorobromide having a high silver chloride content, but can also use silver iodobromide or silver chloroiodobromide.

However, it is known that the acylhydrazine compounds used therein generate nitrogen gas during the developing process, and this gas collects in the film to form bubbles, which may damage a photographic image.

[0010] Therefore, for the purpose of reducing the generation of bubbles and at the same time lowering the production cost of the photosensitive material, a sufficient maximum density can be obtained with high contrast even with a small amount of addition, and uneven development and generation of sand fog (pepper fog) can be obtained. A silver halide photographic light-sensitive material containing a hydrazine compound which is hardly generated is disclosed in JP-A-62-1782.
46, 62-180361, 62-27524
7, and 63-253357.

However, when this photosensitive material is treated with a developing solution having increased activity due to aging fatigue, etc., nucleation and transmission development by the hydrazine compound is promoted, sensitivity is increased, halftone dots are sharply increased, and countless sand fog is caused. Was found to occur. Since this phenomenon occurs regardless of the type of hydrazine used, countermeasures have been required.

[0012]

SUMMARY OF THE INVENTION An object of the present invention is firstly to provide a silver halide photographic light-sensitive material capable of obtaining extremely hard contrast and high sensitivity photographic properties exceeding 10 with a stable developer. It is to provide.

A second object of the present invention is to provide a silver halide photographic light-sensitive material exhibiting ultra-high contrast photographic characteristics and generating less sand fog.

A third object of the present invention is to provide a silver halide photographic light-sensitive material which has an increased sensitivity and little increase in sand fog even when processed with a developing solution having increased activity due to fatigue with time.

[0015]

SUMMARY OF THE INVENTION The object of the present invention is to provide at least one photosensitive silver halide emulsion layer on a support, wherein the silver halide emulsion layer or another hydrophilic colloid layer has the following properties. A silver halide photographic light-sensitive material containing a compound represented by the following formula (3), characterized in that the silver halide emulsion layer contains at least one compound represented by the following formula (4): Achieved by photographic materials.

[0016]

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In the chemical formula 3, Ar represents an aryl group;
Is a group represented by -OR ₁ or -N, (R ₂₎ (R
Represents a group represented by ₃ ). R ₁ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted unsaturated heterocyclic group, or a substituted or unsubstituted aryl group. R ₂ , R ₃
Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted unsaturated heterocyclic group, or a substituted or unsubstituted pyridinium group. R ₂ and R ₃ may be linked to each other to form a ring. ]

[0018]

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In the formula, R ₄ , R ₅ and R ₆ may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or an alkylthio group. , R ₄ and R ₅ may together form a 5- or 6-membered ring. However, the total number of carbon atoms of R ₄ and R ₅ is 3 or more. R ₇ represents a hydroxy group or a mercapto group. ]

In formula 3, the aryl group represented by Ar is specifically a phenyl group or a naphthyl group which may have a substituent, and examples of the substituent include an alkyl group, Aryl group, hydroxyl group, halogen atom, alkoxy group, aryloxy group, alkenyl group, amino group, acylamino group, sulfonamide group, alkylideneamino group, ureido group, thiourea group, thioamide group, heterocyclic group, or a combination thereof And the like.

Further, Ar may have a ballast group commonly used in immobile photographic additives such as color couplers incorporated therein. The ballast group is a group having 8 or more carbon atoms which is relatively inert to photographic properties and can be selected from, for example, an alkyl group, an alkoxy group, a phenyl group, a phenoxy group and the like.

In Formula 3, R represents a group represented by —OR ₁ or a group represented by Formula 5.

[0023]

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R ₁ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted unsaturated heterocyclic group, or a substituted or unsubstituted aryl group.

R ₂ and R ₃ each independently represent a hydrogen atom,
It represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted unsaturated heterocyclic group, or a pyridinium group represented by Chemical formula 6. R ₂ and R ₃ may be linked to each other to form a ring.

[0026]

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R ₈ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted alkenyl group. R ₉ is a hydrogen atom,
Represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkoxy group. X ^- represents an anion.

Next, specific examples of the compound represented by Chemical formula 3 of the present invention will be given, but the scope of the present invention is not limited thereto.

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[0110]

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In the light-sensitive material of the present invention, the compound represented by Chemical formula 3 is preferably contained in a silver halide emulsion layer, but may be contained in another hydrophilic colloid layer.
Since the content of the compound of formula 3 of the present invention in the layer depends on the characteristics of the silver halide emulsion used, the chemical structure of the compound and the development conditions, the appropriate content may vary over a wide range. A range of about 10 ^{-6 to} 5 × 10 ^-2 moles per mole of silver in the silver halide emulsion is practically useful, more preferably a range of 10 ^-5 to 2 × 10 ^-2 moles.

The addition of a tetrazaindene compound to a silver halide photographic emulsion is a technique known to those skilled in the art as described in “Photochemistry” (Photo Kogyo Shuppan). Further, a technique of adding a hydroxytetrazaindene compound to a silver halide photographic emulsion containing a hydrazine compound is disclosed in JP-A-53-84714 and JP-A-6-1983.
4-65541.

However, when the hydrazine compounds disclosed in these publications are processed with a developing solution whose activity has been increased due to fatigue over time or the like, sensitivity is increased and sand fog is increased. I can't control it.

The hydrazine compound represented by Chemical Formula 3 of the present invention also includes 4-hydroxy-6-methyl-1,3,3a, 7 which has been conventionally added to a photosensitive emulsion in the photographic industry.
-With tetrazaindene, the effect of the present invention is hardly observed. That is, it was found that the problem with the fatigue developer can be overcome only by the combination of the compound of the formula 3 and the compound of the formula 4 of the present invention.

Specific examples of the compound represented by Chemical Formula 4 will be given, but the scope of the present invention is not limited thereto.

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[0124]

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In the light-sensitive material of the present invention, the compound represented by Chemical formula 4 is preferably contained in a silver halide emulsion layer, but may be contained in another hydrophilic colloid layer.
Since the content of the compound of formula 4 of the present invention in the layer depends on the characteristics of the silver halide emulsion used, the chemical structure of the compound and the development conditions, the appropriate content may vary over a wide range. A range of about 5 × 10 ^{-6 to} 5 × 10 ^-2 moles per mole of silver in the silver halide emulsion is practically useful, more preferably a range of 1 × 10 ^{-4 to} 3 × 10 ^-2 moles. Is good.

The silver halide emulsion used in the present invention is not particularly limited, and silver chlorobromide, silver chloroiodobromide, silver iodobromide, silver bromide and the like can be used. Alternatively, when silver chloroiodobromide is used, the content of silver iodide is preferably 5 mol% or less.

The form, crystal habit, size distribution and the like of the silver halide grains used in the present invention are not particularly limited, but those having an average grain size of 0.7 μm or less, particularly preferably 0.5 μm or less, are preferred. It is preferable that 90% or more of all the particles have a particle diameter in a range of ± 10% of the average particle diameter. The preparation method of the silver halide emulsion is normal mixing, reverse mixing,
Any of known methods such as simultaneous mixing may be used.

The emulsion after the physical ripening is desalted,
It is preferable that the coating is performed by adding a necessary additive, but the desalting treatment can be omitted.

The silver halide emulsion used in the present invention is:
Chemical sensitization can be performed by a known method. Examples of the sulfur sensitizer include thiosulfate, thiourea, allylisothiocyanate, cystine, rhodanine, and U.S. Pat. Nos. 1,574,944, 2,278,947, 2,410,689, Sulfur-containing compounds as described in JP-A Nos. 2,440,206, 3,187,458, 3,415,649, and 3,501,313 can be used. Along with sulfur sensitization, US Pat. Nos. 2,448,060 and 2,540,086
Nos. 2,556,245 and 2,566,263 can be used in combination with a sensitization method using a salt of a noble metal such as platinum palladium, iridium, rhodium or ruthenium. Further, a sensitization method using various gold compounds such as potassium chloroaurate and auric trichloride and a palladium compound such as palladium chloride can be used in combination.

In the light-sensitive material of the present invention, an overcoat layer, an intermediate layer, a backcoat layer, an undercoat layer and other hydrophilic colloid layers can be provided in addition to the light-sensitive emulsion layer. These layers may also contain a matting agent.

Gelatin is advantageously used as a binder or protective colloid which can be used in the emulsion layer, overcoat layer, intermediate layer, backcoat layer, etc. of the light-sensitive material of the present invention. Sex colloids can also be used. For example, gelatin derivatives, graft polymers of gelatin and other polymers, proteins such as albumin and casein; cellulose derivatives such as hydroxyethylcellulose, carboxymethylcellulose and cellulose sulfates; sugar derivatives such as sodium alginate and starch derivatives; polyvinyl alcohol; Various kinds of synthetic hydrophilic high-molecular substances such as homo- or copolymers such as partial acetal of polyvinyl alcohol, poly-N-vinylpyrrolidone, polyacrylic acid, polymethacrylic acid, polyacrylamide, and polyvinylimidazole can be used. As the gelatin, in addition to lime-processed gelatin, acid-processed gelatin or oxygen-processed gelatin as described in Bull.Soc.Sci.Phot.Japan, No. 16, P30 (1966) may be used. Hydrolyzate and oxygen decomposed product can also be used.

The photographic emulsion used in the present invention includes, for example, known stabilizers such as mercaptotetrazole, mercaptotriazole, benzotriazole and benzimidazole, antifoggants, polyalkylene oxides, thioether compounds, quaternary ammonium salt compounds and the like. Various development accelerators can be contained.

The photographic light-sensitive material of the present invention may contain an inorganic or organic hardener in the photographic emulsion layer and other hydrophilic colloid layers. For example, chromium salts (chromium alum, etc.), aldehydes (formaldehyde, glyoxal, etc.), N-methylol compounds, dioxane derivatives (2,3-dihydroxydioxane, etc.), active vinyl compounds, active halogen compounds (2,4-dichloro- 6-
Hydroxy-S-triazine, etc.) alone or in combination.

Further, the photographic emulsion layer or other hydrophilic colloid layer of the light-sensitive material prepared by using the present invention may contain a coating aid, an antistatic agent, an improvement in slipperiness, an emulsification dispersion, an adhesion prevention and an improvement in photographic characteristics (for example, Surfactants for various purposes such as development acceleration, high contrast, and sensitization. For example, nonionics such as saponins (steroids), alkylene oxide derivatives (polyethylene glycol, polyethylene glycol alkyl ethers, etc.), glycidol derivatives (alkenyl succinic acid polyglycerides, etc.), fatty acid esters of polyhydric alcohols, alkyl esters of sugars, etc. Anionic surfactant containing an acidic group such as a carboxyl group, a sulfo group, a phospho group, a sulfate group, a phosphate group, such as an alkyl carboxylate, an alkyl sulfate, an alkyl phosphate, etc. Agents; amphoteric surfactants such as amino acids, aminoalkyl sulfonic acids, aminoalkyl sulfates or phosphates; heterocyclic quaternary ammonium salts such as aliphatic or aromatic quaternary ammonium salts, pyridinium and imidazolium What cationic surfactant can be used.

The photographic light-sensitive material used in the present invention may contain a water-insoluble or hardly soluble synthetic polymer decomposition product in a photographic emulsion layer or another hydrophilic colloid layer for the purpose of improving dimensional stability and the like. For example, alkyl (meth) acrylate, alkoxyalkyl (meth) acrylate, glycidyl (meth) acrylate, (meth) acrylamide,
Vinyl acetate, acrylonitrile, olefins, styrene and the like alone or in combination, or acrylic acid,
A polymer having a combination of methacrylic acid, α, β-unsaturated dicarboxylic acid, hydroxyalkyl (meth) acrylate, styrene sulfonic acid and the like as a monomer component can be used.

As the photographic light-sensitive material used in the present invention, any support known to those skilled in the art can be used. Examples of the support include glass, cellulose acetate film, polyethylene terephthalate film, paper, baryta-coated paper, polyolefin (for example, polyethylene and polypropylene) laminated paper, polystyrene film, polycarbonate film, and metal plates such as aluminum. These supports may be subjected to corona treatment by a known method, or may be subjected to undercoating by a known method as necessary.

In order to obtain ultra-high contrast photographic characteristics using the silver halide light-sensitive material of the present invention, a conventional lith developer and a pH 13 described in US Pat. No. 2,419,975 can be used.
It is not necessary to use a highly alkaline developer close to the above, and a stable developer can be used. That is, the silver halide photographic light-sensitive material of the present invention can use a developer sufficiently containing (especially, 0.15 mol / l or more) a sulfite ion as a preservative, and has a pH of 9.5 or more. Especially 10.5-1
With the developer of 2.3, a negative image having a sufficiently high contrast can be obtained. There is no particular limitation on the developing agent, and dihydroxybenzenes, 3-pyrazolidones, aminophenols and the like can be used alone or in combination. Other developers include pH buffers such as alkali metal sulfites, carbonates, borates, and phosphates, bromides, iodides, and organic antifoggants (particularly preferably
(Nitroindazoles or benzotriazoles) or a development inhibitor or an antifoggant. Further, if necessary, a water softener, a dissolution aid, a color tone agent, a development accelerator, a surfactant, an antifoaming agent, a hardening agent, an antifouling agent for silver (eg, 2-mercaptobenzimidazole acids) of a film, etc. May be included. Specific examples of these additives are described in Research Disclosure 176 No. 1
7643 and the like.

In the present invention, a system may be employed in which a developing agent is incorporated in a photosensitive material and the photosensitive material is processed with an alkaline activator solution. (Japanese Unexamined Patent Publication Nos. 57-129436, 57-129433, 57-129434, and 5)
7-129435, U.S. Pat. No. 4,323,643). The treatment temperature is usually selected between 18 ° C and 50 ° C, but may be lower than 18 ° C or higher than 50 ° C. It is preferable to use an automatic developing machine for photographic processing. In the present invention, even if the total processing time from when the photosensitive material is put into the automatic developing machine to when it comes out is set to 60 seconds to 120 seconds, a photographic characteristic of a negative tone with a sufficiently high contrast can be obtained.

[0139]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is of course not limited by these descriptions.

Example 1 A cubic monodispersed silver iodobromide emulsion having an average particle diameter of 0.25 μm was prepared by pAg controlled double jet method, and desalted, washed with water and redissolved by flocculation method. The content of silver iodide was 1.5 mol%, and the average was distributed throughout the grains.

This emulsion was sulfur sensitized by a conventional method, and
-Phenyl-5-mercaptotetrazole was added, the mixture was divided, and the tetrazaindene compound of Formula 91 of the present invention was added at 5 × 10 ₋₄ mol / mol Ag.
The hydrazine compounds of the present invention and comparative examples shown in Table 1
10 ^-4 mol / mol Ag was added, and 2-hydroxy-
After adding 4,6-dichloro-1,3,5-triazine sodium salt and sodium dodecylbenzenesulfonate, the mixture was coated on a polyethylene terephthalate film with silver nitrate at 5 g / m @ 2 and gelatin at 3 g / m @ 2. As a protective layer, 1 g of gelatin, a surfactant, a matting agent, and a hardening agent were added thereto and applied, thereby preparing seven types of samples shown in Table 1. The hydrazine of the comparative example tested is shown below.

[0142]

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[0143]

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Each sample thus obtained was exposed and developed, and the sensitivity value was measured. A tungsten lamp was used for the exposure, and the sensitivity value was determined as an exposure amount necessary to obtain a transmission density of 3.0. Table 1 shows a relative value when the sensitivity value of a sample containing no hydrazine compound was set to 100. Indicated by Gamma was represented by tan θ of a linear portion having an optical density of 1.0 to 2.5. Development was performed with a developer having the following composition.
Developing at 30 ° C. for 30 seconds, fixing, washing and drying were performed.

Further, as a test for sand fog, each sample was forcibly developed with the same developer at 38 ° C. for 60 seconds, and the occurrence was examined. Table 1 shows the results. Sand fog was visually evaluated on a scale of 1 to 5, with 5 being the best and 1 being the worst quality. 5 and 4 are practical and 3 is poor, but practically available, and 2 and 1 are not practical.

Further, in order to test the characteristics when processing with a developing solution whose activity was increased due to fatigue with time, the following developing solutions were left in an open container for one week, and then each photosensitive material was exposed and developed in the same manner as above. Processed. The test and evaluation of sand fog were performed in the same manner as above.

<Developer> Hydroquinone 50.0 g N-methyl-p-aminophenol 1 / 2H ₂ SO ₄ 0.3 g Sodium hydroxide 18.0 g 5-Sulfosalicylic acid 55.0 g Potassium sulfite 110.0 g EDTA · 2Na 1 0.0 g Potassium bromide 10.0 g 5-Methylbenzotriazole 0.4 g 2-Mercaptophenimidazole-5-sulfonic acid 0.2 g 3- (5-Mercaptotetrasole) pentane sodium sulfonate 0.2 g Sodium toluene toluene sulfonate 8. Add 0 g water and adjust to pH 11.8 with 1 l potassium hydroxide.

[0148]

[Table 1]

From the results shown in Table 1, the photographic light-sensitive material of the present invention provided a harder image than the photographic light-sensitive material of Comparative Example.
The developer is less susceptible to sand fog and has increased activity due to fatigue with time, etc., and has improved sensitivity and increased sand fog.

Example 2 The emulsion prepared in Example 1 was mixed with the tetrazaindene compounds of the present invention and comparative examples shown in Table 2 at 8 × 10 ^-4 mol / mol A.
g was added thereto, and 5 × 10 ⁻⁴ mol / mol Ag of the present invention was added as a hydrazine compound. According to the method of Example 1, ten kinds of samples shown in Table 2 were prepared. The sample was exposed and developed in the same manner as in Example 1 to determine the sensitivity and gamma. The test and evaluation of sand fog were performed in the same manner as in Example 1. The tested tetrazaindene compound of the comparative example is shown below.

[0151]

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[0152]

[Table 2]

From the results shown in Table 2, the photographic light-sensitive material of the present invention can obtain a similar high sensitivity and high contrast image as compared with the photographic light-sensitive material of the comparative example, and can use a developing solution having increased activity due to aging fatigue and the like. , Sensitivity, and sand fog have also been improved.

[0154]

According to the combination of the hydrazine compound and the tetrazaindene compound of the present invention, rapid development using a stable developing solution having a high sulfite ion concentration provides extremely high contrast, high sensitivity, and low generation of sand fog. In addition, a silver halide light-sensitive material having improved sensitivity and increased sand fog can be obtained with a developing solution having increased activity due to aging fatigue and the like.

──────────────────────────────────────────────────続 き Continued on front page (58) Field surveyed (Int.Cl. ⁶ , DB name) G03C 1/34 G03C 1/06 501

Claims (1)

(57) [Claims] 1. A support having at least one light-sensitive silver halide emulsion layer on a support, wherein said silver halide emulsion layer or another hydrophilic colloid layer contains a compound represented by the following chemical formula 1. A silver halide photographic light-sensitive material, characterized in that the silver halide emulsion layer contains at least one compound represented by the following formula (2). Embedded image [In the formula 1, Ar represents an aryl group, and R represents -OR ₁
Represents a group represented by a group represented by or _{-N, (R 2) (R} 3). R ₁ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted unsaturated heterocyclic group, or a substituted or unsubstituted aryl group. R ₂ and R ₃ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted unsaturated heterocyclic group, or a substituted or unsubstituted pyridinium group. . R ₂ and R ₃ may be linked to each other to form a ring. ] In Chemical Formula 2, R _4, R _5, R _6, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, an alkylthio group, R ₄ And R ₅ may together form a 5- or 6-membered ring. However, the total number of carbon atoms of R ₄ and R ₅ is 3 or more. R ₇ represents a hydroxy group or a mercapto group. ]