US3859100A - Silver halide photographic material containing a hydroxyazaidene and a carboxyl substituted 1,2-dithiolane as stabilizing combination - Google Patents

Silver halide photographic material containing a hydroxyazaidene and a carboxyl substituted 1,2-dithiolane as stabilizing combination Download PDF

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Publication number
US3859100A
US3859100A US344399A US34439973A US3859100A US 3859100 A US3859100 A US 3859100A US 344399 A US344399 A US 344399A US 34439973 A US34439973 A US 34439973A US 3859100 A US3859100 A US 3859100A
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photographic material
compound
silver halide
group
photographic
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US344399A
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Inventor
Susumu Kondo
Tadao Sakai
Reiichi Ohi
Mitsunori Sugiyama
Mitsuo Numata
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium

Definitions

  • ABSTRACT A silver halide emulsion layer in a photographic material which contains at least one triazaindene, tetrazaindene or a pentazaindene having at least one hydroxy group and at least one compound having 21 L2- dithiolane or a l,2-dithiane ring exhibits lower fogging but substantially no reduction in desirable photographic characteristics.
  • anti-fogging agents are, in general, called anti-fogging agents among those skilled in the art and, in some cases, are referred to as stabilizing agents.”
  • stabilizing agents have the common property of lowering the fogging of photographic emulsions but, at the same time, possess the defect of reducing photographic sensitivity or other photographic characteristics, e.g., gamma. Accordingly, the anti-fogging agents have so far been used with some unavoidable loss of sensitivity. Therefore, a method to lower the fogging alone while maintaining the inherent photographic sensitivity has been eagerly sought.
  • a primary object of the present invention is to provide a silver halide photographic light-sensitive material wherein fogging is sufficiently lowered without a reduction in sensitivity.
  • Another object of the invention is to provide a silver halide photographic light-sensitive material wherein the increase in fogging during storage is lowered.
  • a further object of the invention is to provide a silver halide photographic light-sensitive material undergoing less variations in sensitivity or gamma value during storage.
  • the present invention relates to a photographic material comprising a support having thereon a silver halide emulsion layer containing at least one compound having a l,2-dithiolane ring or a 1,2-dithiane ring (hereinafter referred to as "compound A) and at least one of triazaindenes, tetrazaindenes or pentazaindencs.
  • compound B which have at least one hydroxy group (hereinafter referred to as compound B).
  • X represents a divalent (hydrocarbon) rcsidue having 1 6 carbon atoms
  • R represents a carboxylic acid group, a carboxylic acid salt group, a carboxylic acid ester group. or a carboxylic acid amide group
  • m represents 2 or 3.
  • n represents 0 or 1.
  • X in general formula (I) there are methylene, ethylene, propylene, hutylene. hexylene, etc.
  • carboxylic acid salts there are alkali metal salts (e.g., sodium salts, potassium salts, etc.), alkaline earth metal salts (e.g., calcium salts, barium salts, etc.), ammonium salts, amine salts (e.g., methylamine salts, ethylamine salts, ethanolamine salts, etc.) and the like.
  • alkali metal salts e.g., sodium salts, potassium salts, etc.
  • alkaline earth metal salts e.g., calcium salts, barium salts, etc.
  • ammonium salts e.g., sodium salts, potassium salts, etc.
  • alkaline earth metal salts e.g., calcium salts, barium salts, etc.
  • ammonium salts e.g., ammonium salts
  • amine salts e.g., methylamine salts, ethylamine salts, ethanolamine salts, etc.
  • Examples of preferred carboxylic acid esters are esters with 'a C C alkyl group or a phenyl group, and the like.
  • Examples of preferred carboxylic acid amides are carboxylic acid amide and carboxylic acid amide substituted by a C C alkyl group or by a phenyl group. and the like.
  • Compound A used in the invention is structurally characterized by containing a dithiolane ring or a dithiane ring, and exerts the action of lowering fogging of silver halides due to this structural feature. Therefore, compound A used in the invention is not particularly limited to that represented by the foregoing general formula (I). and any compound having a dithiolane or a dithiane ring may be used.
  • the compounds represented by the foregoing general formula (I) may be synthesized according to known processes, e.g., described in "Journal of the American Chemical Society," 76, pp. 1,828 1832 (1954).
  • These compounds may further contain substituents in addition to the hydroxy group, and such are included within the terms triazaindcnes, tetrazaindenes and pentazaindenes in the specification and claims.
  • substituents there are illustrated a halogen, an alkyl group having 1 17 carbon atoms, an aralkyl group, an aryl group, an alkoxy group having I 18 carbon atoms, a carboxyl group.
  • an alkoxycarbonyl group having 1 18 carbon atoms, an aminocarbonyl group, a cyano group, a group forming a hydrocarbon ring together with the adjacent carbon atoms See for example, compounds 8-1 2, 8-14, where a saturated ring is formed; the adjacent carbon atoms are bicinal carbon atoms which form the azaindene ring), and the like.
  • any special substituent(s) on the azaindene ring other than the hydroxy group is rather immaterial and any substituent(s) excepting those such as a nitro group or mercapto group which adversely affect the photographic properties, such as sensitivity and fog, of the light-sensitive emulsion can be present. All such substituted azaindenes are to be construed as within the scope of the present invention.
  • Compound B is characterized by containing an azaindene ring having at least one hydroxy group, and may contain substituents other than are described above.
  • Compound B may be synthesized according to known processes, e.g.. described in "Chemical and Pharmaceutical Bulletin, 6, pp. 583 586 (1958), or ibid., 10, pp. 612 620 (I962).
  • Typical useful examples of compound 8 are as follows.
  • compound (A) and compound (B) H added vary depending upon the presence of additives B 0H 3 to the emulsion, such as a sensitizing agent. In general. greater amounts of a sensitizing agent causes higher fog 13502000 N 40 density, thus, greater amounts of the compounds are needed. In general. compound (A) is suitably added in x an amount of from about 0.0005 g to about 5 g and N compound (B) from about 0.005 to about g. per 1 0NH2 mol of silver halide contained in the emulsion. Prefera- B-11 OH bly.
  • compound (A) is added in an amount of from ,N about 0.005 to 0.5 g, compound (B) from about 0.05 13502000 to 5 g. same basis as above.
  • the optimal amount can be J determined by the preliminary test well known by those 50 skilled in the art, i.e.. a series of runs, wherein the N amount of the compounds is varied.
  • B42 OH As will be appreciated by one skilled in the art.
  • one A can use one or more different compounds (A) in combination with one or more different compounds (8 In H this case of course, the total amount of the different ⁇ N compounds suitably falls within the ranges recited above.
  • CH3 N These compounds are added to a silver halide emul- N sion advantageously as a solution.
  • a silver halide photographic light-sensitive material is produced via the following steps; l prepa- Nx ration and weighing of starting materials for the pro- H duction of emulsion; (2) emulsification; (3) first ripening or physical ripening; (4) removal of water-soluble N N salts; (5 second ripening or chemical ripening; and (6) coming of the emulsion. (For example, see Making and Coating Photographic Emulsions, pp. 17 22, issued by Focal Press Co.)
  • compound (A) and compound (B) may effectively be added to an emulsion during production of the silver halide emulsion (i.e., in the above-described steps (1) to or immediately before coating the emulsion.
  • a particularly prefered stage of the addition is between the second ripening step and the coating step.
  • any of the ,known ones such as silver chloride, silver bromide, silver chlorobromide, silver bromoiodide, silver chloroiodide, silver chlorobromoiodide and the like can be used.
  • halogen conversion-type silver halide grains as described in British Pat. No. 635,841 may also be used effectively.
  • any hydrophilic colloid applied to usual silver halide emulsions may be used.
  • gelatin, albumin, gum arabic, agaragar, cellulose derivatives (e.g., carboxycellulose alkyl esters, hydroxyethyl cellulose, carboxymethylhydroxyethyl cellulose, etc.), synthetic resins (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, etc.), and the like are merely a small sampling of those hydrophilic colloids which can be used in the present invention.
  • the generally used ratio of silver halide binder is l 2 about from 0.1 to 20.
  • a preferred particle size for the silver halide is from about 0.05. to about 5 microns. Neither of these ranges are limitative, and they can be varied in a manner known to the art.
  • group 1 elements such as rubidium, cesium, copper, silver, gold, etc.
  • group 1] elements such as magnesium, strontium, zinc, cadmium, mercury, etc.
  • group Vlll elements such as iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, irid- ,ium, platinum, etc., in order to adjust the photographic characteristics of the emulsion.
  • the photographic emulsion can be subjected to chemical ripening with active gelatin or with the use of a sulfur compound in a manner as described in U.S. Pat. Nos. 1,574,944; 1,623,499 or 2,410,689.
  • the photographic emulsion can be chemically sensitized with gold salts such as are described in U.S. Pat. No. 2,399,083; with reducing agents such as the stannous salts described in U.S. Pat. No. 2,487,850; reducing agents such as the polyamines described in U.S. Pat. No. 2,52l,925; with bis(beta-aminoethyl)sulfides and the water-solublesalts thereof described in U.S. Pat. No. 2,521,926; with compounds containing a labile selenium atom as described in U.S. Pat. Nos.
  • 3,297,446; 3,297,447 and 3,442,653 can be sensitized by the addition of polyalkylene glycols as described in U.S. Pat. Nos. 2,423,549 and 2,441,389; or with various derivatives of alkylene oxides as described in U.S. Pat. No. 2,240,472 and British Pat. No. 443,559.
  • the above-described photographic emulsion may, of course, be spectrally sensitized with a cyanine or merocyanine dye.
  • hydrophilic colloid used in the photographic light-sensitive material of the invention is advantageously hardened by the generally used hardeners of the aldehyde series, methylol series, 1,4-dioxane series,
  • indazolone series, etc. can advantageously be used.
  • all of the cyan dye-forming couplers of the phenol series, naphthol series, etc. can advantageously be used. These couplers may contain a coupling-off group at the active carbon atom positioned at the coupling cite. Those couplers rendered nondiffusible with a ballast group are prefered. With respect to these couplers, a great number of ballasted compounds are well known.
  • dye-forming couplers can be dispersed in a hydrophilic colloid in any known manner. They can advantageously be dispersed with the use of a coupler solvent as described in U.S. Pat. No. 2,322,027, etc.
  • the photographic light-sensitive material of the invention can contain aplasticizer such as glycerin, a coating aid such as saponin, polyethylene glycol monolauryl ether, etc., a lubricating agent such as a silicone resin, paraffin, etc., a matting agent such as starch, titanium dioxide, a silicate, etc., a water-soluble azo dye, polymethine dye, diphenylmethane dye, etc., a brightening agent of the stylbine series, triazine series, oxazole series, coumarin series, etc., antistatic agents such as the ionic polymers described in U.S. Pat. No. 2,861,056, and antioxidants such as hydroquinone derivatives, ascorbic acid, etc.
  • aplasticizer such as glycerin
  • a coating aid such as saponin, polyethylene glycol monolauryl ether, etc.
  • a lubricating agent such as a silicone resin, paraffin, etc.
  • the photographic light-sensitive material of the invention can contain ultraviolet ray-absorbing agents such as Michlers diketone sulfonic acid, benzotriazole, etc., or may contain colloidal silver, carbon black or the like to prevent static marks.
  • ultraviolet ray-absorbing agents such as Michlers diketone sulfonic acid, benzotriazole, etc.
  • cellulose ester films such as cellulose nitrate. cellulose acetate, etc.
  • polyester films such as polyethylene terephthalatefilms, etc., polyvinyl chloride films, polystyrene films, polycarbonate films, baryta paper and albisulfite, bromide, iodide, etc. of an alkali metal.
  • Other useful black-and-white developing agents are described, for example, in The Theory of the Photographic Process, 3rd Edition, pp. 278 331, issued by MacMillan Co.
  • Color developers as are commonly used in the art can also be used in the present invention, i.e., any alkaline aqueous solution containing a color-developing agent.
  • a color-developing agent all known dye-forming aromatic primary.
  • amine developers such as phenylenediamines (e.g., N,N-diethyl-p-phenylene-diamine, N-
  • N-ethyl-N- sion was divided into three equal portions, one ofwhich hydroxyethyl-2-methyl-p-phenylenediamine, Nethylwas used as a control and to the remaining two of which beta-N-methanesulfonamidoethyl-3-methyl-4- were added, respectively, the compounds described in aminoaniline, N,N-diethyl-2-methyl-p- Table 1.
  • Each ofthe thus obtained three emulsions was phenylenediamine, and the sulfonates, hydrochlorides applied to a triacetate cellulose film support in a coated and sulfites thereof, etc.) can be used.
  • the color develsilver amount of 2.5-X 10 mol/m then dried.
  • oper may further contain generally used additives such
  • the thus prepared samples were subjected to sensias a sulfite, carbonatebisulfite, bromide or iodide of an me ry in a known m e to mp r Ihc sensitivity. alkali metal, benzyl alcohol and the lik gamma value and fog density of each sample.
  • Develop- 0 As other processing solutions, e.g., a bleaching solumehl was Conducted at Q C for 3 mlhulcs 115mg tion, a fixing solution, a stabilizing solution, etc., ones P having the following chmphslhhhknown in the art may advantageously be used.
  • processing solutions may be used in combinations of N Mcthy
  • Ableaching solution contains a silver oxidizing agent(s), e.g., water-soluble Aftehdeveloplhehh each the samples "hferricyanides, a 'simple water-soluble ferric, cupric or mersed m a hpp bath at 20 C lzpercehf "101d b l i Salt d Complex Salts f an lk li metal d 25 aqueous solution) for seconds, washed for l minute polyvalent cations with an organic acid.
  • a silver oxidizing agent(s) e.g., water-soluble Aftehdeveloplhehh each the samples "hferricyanides, a 'simple water-soluble ferric, cupric or mersed m a hpp bath at 20 C lzpercehf "101d b l i Salt d Complex Salts f an lk li metal d 25 aqueous solution) for seconds, washed for
  • Typical examwith a Fuhhlhg which h 111 h 8 minutes ples of the polyvalent cations are ferric ions, cobaltic u ng a fixing solution having the following composiions, cupric ions, etc.
  • a fixing solution contains a silver hal- 30 ide solvent(s) for example, a water-soluble thiosulfate,
  • Anhydrous 15 g contains, of course, a stabilizer such as formaldehyde, gorichacild i: g otas auni l, g citr c acid, etc. Specific examples of these compounds Sodium mum m g 3T0 illustrated on U.S. Pat. NO. 3,582,322. Water to make l liter.
  • EXAMPLE 2 A silver halide gelatin photographic emulsion (containing 0.06 mol silver per 100 g) comprising silver excellent preservability is shown,
  • EXAMPLE 3 chlorobromide containing 25 mol percent chlorine sub- 5
  • a silver halide gelatin photographic emulsion (conjected to second ripening with the use of sulfur comtaining 0.08 mol silver per 100 g) comprising silver bropound and gold salt was prepared in the same manner moiodide'containing 1.8 mol percent iodide was preas in Example 1. pared by conducting second ripening with the use of After the completion of ripening, the resulting emulthe sulfur compound and gold salt in the same manner sion was divided into 4 equal portions. One of them was as m EXamPle 1 and adding 0.4 g.
  • Example 1 The thus prepared samples were subjected to sensi- Each ofthe Samples was subficted to f l y tometry in a known manner to compare the sensitivity, a known manner compdfe the sensltlvltygamma gamma value and fog density of each Sample Develop value and fog dens ty, sub ected to development at mem was conducted at for 2 minutes using a 20C for 10 minutes in a developer having the following veloper having the following Composition composition, and subsequently processed in the same manner as in Example 1.
  • Each of the resulting coating solutions was applied to a cellulose triacetate film support in a coated silver amount of 9.8 X l0" mol/m then dried.
  • the thus prepared samples were subjected to sensitometry in a known mannerto compare sensitivity, gamma and fog density.
  • the samples were processed through the pro cessing baths of color development, stopfixing, bleaching and fixing selected from among the processing steps amylphenoxy)butylamido[-acetanilide(dibutyl phthalate solution) was added thereto to prepare coating solutions (6.5 g of yellow coupler per 100 g of emulsion was added).
  • the resulting coating solutions were applied to the same paper support as was used in Example 0 2 in a coated silver amount of 5.9 X 10"" mol/m then dried.
  • Thethus prepared samples were subjected to sensitometry in a known manner to compare sensitivity, gamma and fog density.
  • the samples were processed according to processing step B for color photographic paper described in Example 2 in US. Pat. No. 3,582,322.
  • Example 5 An incubation test was conducted in the same manner as in Example l. The results obtained are shown in Table 5. It can be seen that in this case also fogging alone can be lowered by the combined use of compound A and compound B while maintaining the sensitivity and gamma value, and the photographic characteristics upon storage are extremely stable.
  • a photographic material comprising a support having thereon a silver halide emulsion layer containing (1) at least one of a triazaindene, a tetrazaindene' or a pentazaindene having at least one hydroxy group wherein X represents an alkylene group having 1-6 carbon atoms, R represents a carboxylic acid group, a carboxylic acid salt group, a carboxylic acid ester group,
  • n Oor l
  • a photographic material as described in claim 1 where said compound is and said azaindene is 13.
  • a photographic material as described in claim 1 where said compound is and said azaindene is N N CH3 N 14.
  • a photographic material as described in claim I and said azaindene is where said compound is C OII

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  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US344399A 1972-03-29 1973-03-23 Silver halide photographic material containing a hydroxyazaidene and a carboxyl substituted 1,2-dithiolane as stabilizing combination Expired - Lifetime US3859100A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4210716A (en) * 1979-01-31 1980-07-01 E. I. Du Pont De Nemours And Company Silver halide emulsion containing tetrathiocino diisothiazoles as antifoggers
US4272613A (en) * 1979-05-18 1981-06-09 Fuji Photo Film Co., Ltd. Color photographic process
WO1982001260A1 (en) * 1980-10-02 1982-04-15 Minnesota Mining & Mfg Chemically sensitized silver halide photographic emulsions and color photographic elements containing said emulsions
US4729946A (en) * 1984-02-01 1988-03-08 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US5219721A (en) * 1992-04-16 1993-06-15 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
EP0599199A1 (en) * 1992-11-19 1994-06-01 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic disulfides and sulfinates
EP0566074A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Photographic silver halide emulsions precipitated in the presence of organic dichalcogenides.
US5482825A (en) * 1994-12-23 1996-01-09 Eastman Kodak Company Silver halide emulsions containing fused dihydropyrimidines

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58126526A (ja) * 1981-12-19 1983-07-28 Konishiroku Photo Ind Co Ltd ハロゲン化銀乳剤の製造方法およびハロゲン化銀写真感光材料
EP0617320A3 (en) * 1993-03-22 1995-02-01 Eastman Kodak Co Tabular grain emulsions containing anti-stars and stabilizers.

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2728668A (en) * 1952-12-05 1955-12-27 Du Pont Photographic emulsions containing a 1,2-dithiolane
US2948614A (en) * 1957-07-11 1960-08-09 Stabilized photographic silver halede
US3128186A (en) * 1960-07-15 1964-04-07 Gen Foods Corp Stabilized photographic silver halide emulsions
US3732104A (en) * 1969-11-03 1973-05-08 Agfa Gevaert Nv Silver halide emulsions containing azaindene and amide stabilizing agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE549178A (en, 2012) * 1955-07-05
BE624418A (en, 2012) * 1961-11-06
US3563754A (en) * 1966-11-23 1971-02-16 Eastman Kodak Co Photographic process

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2728668A (en) * 1952-12-05 1955-12-27 Du Pont Photographic emulsions containing a 1,2-dithiolane
US2948614A (en) * 1957-07-11 1960-08-09 Stabilized photographic silver halede
US3128186A (en) * 1960-07-15 1964-04-07 Gen Foods Corp Stabilized photographic silver halide emulsions
US3732104A (en) * 1969-11-03 1973-05-08 Agfa Gevaert Nv Silver halide emulsions containing azaindene and amide stabilizing agents

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4210716A (en) * 1979-01-31 1980-07-01 E. I. Du Pont De Nemours And Company Silver halide emulsion containing tetrathiocino diisothiazoles as antifoggers
US4272613A (en) * 1979-05-18 1981-06-09 Fuji Photo Film Co., Ltd. Color photographic process
WO1982001260A1 (en) * 1980-10-02 1982-04-15 Minnesota Mining & Mfg Chemically sensitized silver halide photographic emulsions and color photographic elements containing said emulsions
US4729946A (en) * 1984-02-01 1988-03-08 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US5219721A (en) * 1992-04-16 1993-06-15 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
EP0566080A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Photographic silver halide emulsions sensitized in the presence of organic dichalcogenides.
EP0566074A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Photographic silver halide emulsions precipitated in the presence of organic dichalcogenides.
EP0599199A1 (en) * 1992-11-19 1994-06-01 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic disulfides and sulfinates
US5482825A (en) * 1994-12-23 1996-01-09 Eastman Kodak Company Silver halide emulsions containing fused dihydropyrimidines

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GB1365671A (en) 1974-09-04
JPS4898819A (en, 2012) 1973-12-14
DE2315758A1 (de) 1973-10-04
JPS5125339B2 (en, 2012) 1976-07-30

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