US3926632A - Photographic silver halide lith material - Google Patents

Photographic silver halide lith material Download PDF

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Publication number
US3926632A
US3926632A US279795A US27979572A US3926632A US 3926632 A US3926632 A US 3926632A US 279795 A US279795 A US 279795A US 27979572 A US27979572 A US 27979572A US 3926632 A US3926632 A US 3926632A
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Prior art keywords
alkylene
water
compound
stands
arylene
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US279795A
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Emiel Alexander Hofman
Jules Robert Berendsen
Robert Joseph Pollet
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Agfa Gevaert NV
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Agfa Gevaert NV
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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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/15—Lithographic emulsion

Definitions

  • ABSTRACT A method is provided of producing high contrast images by development at a temperature above 30C of an exposed photographic light-sensitive lith-material comprising a support having thereon at least one light sensitive silver halide emulsion, which comprises at least 50 mole percent of silver chloride and at least 5 mole percent of silver bromide, wherein the said material comprises a disulphide compound of the formula:
  • Lith emulsions which are widely used for line and screen photography, have a chracteristic curve with a short toe and high gamma and produce sharply defined images with high density extending to the edges of lines and dots.
  • lith emulsions are preferably developed in lith -type developers they can also be developed in conventional highcontrast developers such as a Metolhydroquinone developer, or a developer composition of the kind described in copending U.S. application Ser. No. 426,134 filed Dec. 19, 1973, which is acontinuation of U.S. application Ser. No. 226,232 filed Feb. 14, 1972 Development of exposed photographic silver halide materials including lith materials normally occurs at ambient temperature (about 20C). Whereas, in careful tray processing the development time is of minor importance, it is desirable in machine processing to reduce the time of processing, which can be done by carrying out processing at elevated temperatures, say above 30C.
  • each of'A, and A represents alkylene, preferably C C; alkylene which may be substituted e.g. by alkyl and aryl, arylene e.g. phenylene which may be substituted e.g. by alkyl, alkoxy, halogen or a water-solubilizing group e.g. sulpho and carboxyl in acid or salt form, or a bivalent heterocyclic group, and
  • each of X and Y represents a water-solubilizing group e.g. sulpho and carboxyl in acid or salt form or a substituent carrying such water-solubilizing group, the said substituent forming a bridging group between the water-solubilizing group and A, or A and may be a saturated or unsaturated aliphatic group, e.g. alkyleneoxy, alkyleneoxycarbonyl, vinylene, alkyleneoxycarbonylvinyl, alkylenecarbamoyl, alkylene sulphamoyl, alkylene amino and alkylene acylamino; an aromatic group e.g. phenylene, phenylene carbamoyl, phenylene sulphamoyl and phenylene acylamino; or a heterocyclic group eg benziniidazolylene.
  • a water-solubilizing group e.g. sulpho and carboxyl in acid or salt form
  • the lith emulsions used according to the present invention are high contrast fine grain silver halide emulsions which contain at least about 50 mole percent of silver chloride and at least about 5 mole percent of silver bromide. If desired, the silver halide can also contain a small amount of silver iodide; this amount is less than about 5 mole percent and preferably less than 1 mole percent. Y Y Y
  • the present invention thus provides a method of developing at a temperature above 30C an exposed lith type of silver halide material ,-.of the kind described above that comprises a disulphide compound corresponding to the above general formula.
  • a hydroquinone developer having a high content of alkali sulphite e.g. a Metol-hydroquinone developer or a developer of the kinddescribed in the cognate co-pending U.S. application Ser. No. 426,134 filed Dec. 19, 1973, which is a continuation of U.S. application Ser. No. 226,232 filed Feb. 14, 1972 may also be used.
  • the fog produced by development at temperatures above 30C is substantially reduced by means of the disulphide compounds corresponding to the above general formula.
  • the developer described in the cognate co-pending Applications 4646/71 and 1282/72, which is suitable for lith-development comprises a p-dihydroxybenzene developing agent, preferably hydroquinone, an amount of sulphite ions of at least 5 g per litre, and a nitroindazole or nitrobenzimidazole corresponding to one of the following general formulae:
  • an aliphatic, aromatiteor heterocyclic disulphide compound carrying at least one water-solubilizing group in acid or salt form, e.g. a sulpho group or carboxyl group, especially a disulphide compound which corresponds to the following eneral formula:
  • Y is a nitro substituent in the 5'- er -iosition of the indazole nucleus
  • X is hydrogen or a sulpho reap in salt form
  • R is hydrogen or a C -C alLyl group
  • X is a sulpho group in salt farm
  • Y is nitro
  • n is a positive integer l, 2 or 3. the said developer being substantially free from any auxiliary developing agent that shows a superadditive developing effect with the said p-dihydroxybenzene developing agent.
  • disulphide compounds for use according to the present invention are:
  • Compound 5 can be prepared as described in J. Org. Chem. 27 (1972 2840.
  • Compound 6 can be prepared as described in US. Pat. No. 3,057,725
  • Compound 8 can be prepared as described in Org. Syn. Coll. Vol. II, 580 (1943).
  • Compound 9 can be prepared as described in J. Am. Chem. Soc. 57 (1935) 45.
  • the disodium salt was suspended in 1000 m1 of dimethyl formamide whereupon 122 g (1 mole) of propane sultone were added. The mixture was heated for 2 hours at 120C with stirring and then partially concentrated by evaporation under reduced pressure. The precipitate formed was washed repeatedly with ether and then with acetone whereupon it was dried till constant weight.
  • This compound was prepared in a similar way as compound 13 starting from 71.6 g (0.2 mole) ofcompound 5 and using 48.8 g (0.4 mole) of propane sultone. Yield: 112 g (87 Melting point: 150C.
  • the p-nitrophenol potassium salt was suspended in 1200 ml of dimethyl formamide whereupon 122. g (1 mole) of propane sultone were added. The mixture was stirred and heated for 6 hours at 160C whereupon it was concentrated by evaporation, stirred with ether and dried.
  • step b 149.5 g (0.5 mole) of the compound prepared in step a) were dissolved in 2 litres of water whereupon ml of Raney Nickel were added. The nitro compound was reduced under a hydrogen pressure of 1500 psi at 80C. The Raney nickel was filtered off and the filtrate concentrated to a volume of 100 ml. The precipitate formed was filtered off by suction and washed with ice-water.
  • the mixture was left standing overnight and then acidified to pH 1 by means of concentrated hydrochloric acid whereupon it was heated for 4 hours on a boiling water-bath.
  • the precipitate of sulphur was filtered off and the filtrate was neutralized and concentrated to a volume of 100 ml.
  • the precipitate was filtered off by suction and purified by continuous extraction with methanol.
  • the mixture was cooled to 40C whereupon 80 ml of carbon disulphide were added dropwise with stirring. The temperature was gradually raised and kept for 5 hours at 9095C.
  • the mixture was stirred for 1' hour and the precipitate formed was filtered off and washed with cold water.
  • the amount of disulphide compound used in the lithmaterials in accordance with the present invention may vary within wide limits and depends on the particular compound involved. They are preferably used in amounts comprised between about 5 and about 1000 mg per mole of silver halide.
  • the silver halides can be dispersed. in the common hydrophilic colloids such as gelatin, casein, zein, polyvinyl alcohol, carboxymethyl cellulose, alginic acid etc. gelatin, however, being preferred.
  • common hydrophilic colloids such as gelatin, casein, zein, polyvinyl alcohol, carboxymethyl cellulose, alginic acid etc. gelatin, however, being preferred.
  • the silver halide emulsions may be chemically sensitized by effecting the ripening in the presence of small amounts of sulphur containing compounds such as allyl thiocyanate, allyl thiourea, sodium thiosulphate etc.
  • the emulsions may also be sensitized by means of reductors for instance tin compounds as described in our British Pat. Specification No. 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium compounds.
  • reductors for instance tin compounds as described in our British Pat. Specification No. 789,823
  • noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium compounds.
  • these three types of chemical sensitizers may be used simultaneously.
  • the emulsions may be used without being spectrally sensitized; however, it is advantageous to spectrally sensitize them according to methods well known in the art to make them ortho-sensitized or panchromatically sensitized.
  • 'Spet'ral sensitizers that can be used are e.g.,
  • the silver halide emulsion of the high-contrast photographic elements according to the present invention may also contain conventional addenda for example, plasticizers, coating aids, fog-inhibiting or emulsion stabilizing'compounds e.g. cadmium salts, and hardeners such as aldehyde hardeners, e.g., formaldehyde, mucochloric acid, glutaraldehyde bis(sodium hydrogen sulphite), maleic dialdehyde, aziridines, dioxan derivatives, and oxypolysaccharides.
  • plasticizers e.g., plasticizers, coating aids, fog-inhibiting or emulsion stabilizing'compounds e.g. cadmium salts
  • hardeners such as aldehyde hardeners, e.g., formaldehyde, mucochloric acid, glutaraldehyde bis(sodium hydrogen sulphite), maleic dial
  • lith-type silver halide materials of the present invention preferably occurs in the presence of polyoxyethylene compounds, which may be present either in the lith-material or in the developing solution or in both.
  • polyoxyethylene compounds include any polymeric compound comprising a polyethylene oxide chain e.g. polyethylene glycol having a molecular weight of 1500 or more and other ethylene oxide compounds as described amongst others in the United Kingdom Patent specification Nos. 600,058 871,801 920,637 940,051 945,340 949,643
  • the lith-emulsion and/or lith-developer may further contain onium and polyonium compounds, preferably of the ammonium, phosphonium and sulphonium type or mixtures thereof.
  • onium compounds are e.g. dodecyl-trimethyl.
  • ammonium p-toluene sulphonate nonyl pyridinium perchlorate, l-m-nitrobenzylquinolinium chloride, l-dodecylpyridinium chloride, N,N'-tetramethylene-bispyridinium chloride, N,N- hexadecamethylene-bispyridinium perchlorate, nnonyl dimethyl sulphonium p-toluene sulphonate, tetramethylene bistriethyl phosphonium bromide, lauryl triethyl phosphonium bromide, onium salts of polyoxyalkylenes e. g.
  • polyoxyalkylene bispyridinium salts etc.
  • suitable onium compounds can be found in U.S. Pat. Nos. 2,271,662 2,271,263 2,275,727 2,288,226 9.944,898 2,944,900 and
  • the silver halide emulsions of use according to the invention may be coated on a wide variety of supports. Hydrophilic colloid layers may be coated on one or both sides of the support, if desired.
  • Typical supports are cellulose nitrate film, cellulose ester film, polyvinyl acetal film, polystyrene film, poly(ethylene terephthalate) film, and related films of resinous material, as well as glass, paper, metal and the like.
  • Supports such as paper, which are coated with a-olefin polymers, particularly polymers of a-olefins containing two or more carbon atoms, as exemplified by polyethylene, polypropylene, ethylenebutene copolymers and the like may also be employed.
  • a-olefin polymers particularly polymers of a-olefins containing two or more carbon atoms, as exemplified by polyethylene, polypropylene, ethylenebutene copolymers and the like may also be employed.
  • EXAMPLE 1 A fine-grain silver halide emulsion of the lith-type containing 75 mole percent of silver chloride and 25 mole percent of silver bromide was prepared in the.
  • the emulsion speed was not affected to a noteworthy extent.
  • EXAMPLE 3 An emulsion of the type described in example 1 was divided into several aliquot portions. To each of these portions, except one, a disulphide compound was added as listed in the table below in the amount given.
  • Example 2 After coating on a support as described in Example 1 the materials were stored for 36 hours at 57C and 34 percent relative humidity.
  • each of A, and A represents an alkylene group
  • X and Y represents a water-solubilizing group in acid or salt form, or a substituent carrying a water-solubilizing group, said substituent forming a bridging group between the water-solubilizing group and A, and A selected from a saturated or unsaturated aliphatic group, an aromatic group and a benzimidazolylene group.
  • each of A, and A stands for phenylene and each of X and Y stands for a water-solubilizing group in acid or salt form. 4. Method according to claim 1, wherein the said disulphide compound has the fiormula:
  • each of A, and A stands for C,C alkylene and each of X and Y stands for a substituent carrying a water-solubilizing group in acid or salt form, the said substituent being a bridging benzimidazolylene, alkylene carbamoyl, alkylene sulphamoyl, arylene carbamoyl, arylene sulphamoyl, alkylene amino, alkylene acylamino or arylene acylamino group between the water-solubilizing group and the alkylene groups represented by A, and A 5.
  • the said disulphide compound has the formula:
  • each of A, and A is a phenylene group and each of X and Y stands for a substituent carrying a watersolubilizing group in acid or salt form, the said substituent being a bridging alkyleneoxy, alkyleneoxycarbonyl, vinylene, alkyleneoxycarbonylvinyl, alkylene carbamoyl, alkylene sulphamoyl, arylene carbamoyl, arylene sylphamoyl, alkylene acylamino or arylene acylamino group between the water-solubilizing group and the phenylene groups represented by A, and A 6.
  • Method according to claim 1 wherein the said disulphide compound is present in the silver halide emulsion in an amount comprised between 5 mg. and 1000 mg per mole of silver halide.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
US279795A 1971-09-13 1972-08-11 Photographic silver halide lith material Expired - Lifetime US3926632A (en)

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GB4256271A GB1383640A (en) 1971-09-13 1971-09-13 Light-sensitive silver halide elements

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JP (1) JPS4838137A (de)
BE (1) BE788685A (de)
DE (1) DE2244916A1 (de)
FR (1) FR2152993B1 (de)
GB (1) GB1383640A (de)

Cited By (5)

* 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
US4699873A (en) * 1985-01-29 1987-10-13 Fuji Photo Film Co., Ltd. Negative 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
US5418127A (en) * 1993-05-28 1995-05-23 Eastman Kodak Company Water-soluble disulfides in silver halide emulsions
US6764814B2 (en) 2001-02-13 2004-07-20 Eastman Kodak Company Photographic developing composition and use thereof in the development of a photographic element

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2564158B2 (ja) * 1988-01-11 1996-12-18 コニカ株式会社 高コントラストな画像形成方法
US5328820A (en) * 1992-11-19 1994-07-12 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic disulfides and sulfinates
JPH07120865A (ja) * 1993-10-21 1995-05-12 Konica Corp ハロゲン化銀写真感光材料
US7282602B2 (en) * 2004-09-21 2007-10-16 Bionumerik Pharmaceuticals, Inc. Medicinal disulfide salts

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3043696A (en) * 1959-09-04 1962-07-10 Eastman Kodak Co Substituted disulfides as antifoggants for silver halide emulsions
US3057725A (en) * 1959-07-17 1962-10-09 Eastman Kodak Co Substituted disulfides as antifoggants for silver halide emulsions
US3062654A (en) * 1959-07-17 1962-11-06 Eastman Kodak Co Stabilization of photographic silver halide emulsions
US3226232A (en) * 1963-05-16 1965-12-28 Gen Aniline & Film Corp Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid
US3397986A (en) * 1964-12-29 1968-08-20 Eastman Kodak Co Photographic emulsion stabilized with bis (p-acylamidophenyl) disulfides
US3447925A (en) * 1965-10-23 1969-06-03 Gaf Corp Anti-fogging and anti-plumming disulfide compound for use in silver halide photographs
US3573914A (en) * 1966-10-03 1971-04-06 Eastman Kodak Co Photographic developer composition containing carbonyl bisulfite amine condensation product and free amine
US3615488A (en) * 1970-03-18 1971-10-26 Eastman Kodak Co Photographic processing composition and process comprising cysteine and an aldehyde bisulfite
US3615527A (en) * 1968-06-29 1971-10-26 Fuji Photo Film Co Ltd Photographic light-sensitive material and development process comprising a development accelerator
US3640715A (en) * 1968-12-23 1972-02-08 Agfa Gevaert Ag Photographic silver halide emulsion containing as a sensitizer bio-quarternary salts of bis-aminoalkyl-disulfides
US3647469A (en) * 1968-12-23 1972-03-07 Agfa Gevaert Ag Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057725A (en) * 1959-07-17 1962-10-09 Eastman Kodak Co Substituted disulfides as antifoggants for silver halide emulsions
US3062654A (en) * 1959-07-17 1962-11-06 Eastman Kodak Co Stabilization of photographic silver halide emulsions
US3043696A (en) * 1959-09-04 1962-07-10 Eastman Kodak Co Substituted disulfides as antifoggants for silver halide emulsions
US3226232A (en) * 1963-05-16 1965-12-28 Gen Aniline & Film Corp Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid
US3397986A (en) * 1964-12-29 1968-08-20 Eastman Kodak Co Photographic emulsion stabilized with bis (p-acylamidophenyl) disulfides
US3447925A (en) * 1965-10-23 1969-06-03 Gaf Corp Anti-fogging and anti-plumming disulfide compound for use in silver halide photographs
US3573914A (en) * 1966-10-03 1971-04-06 Eastman Kodak Co Photographic developer composition containing carbonyl bisulfite amine condensation product and free amine
US3615527A (en) * 1968-06-29 1971-10-26 Fuji Photo Film Co Ltd Photographic light-sensitive material and development process comprising a development accelerator
US3640715A (en) * 1968-12-23 1972-02-08 Agfa Gevaert Ag Photographic silver halide emulsion containing as a sensitizer bio-quarternary salts of bis-aminoalkyl-disulfides
US3647469A (en) * 1968-12-23 1972-03-07 Agfa Gevaert Ag Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions
US3615488A (en) * 1970-03-18 1971-10-26 Eastman Kodak Co Photographic processing composition and process comprising cysteine and an aldehyde bisulfite

Cited By (7)

* 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
US4699873A (en) * 1985-01-29 1987-10-13 Fuji Photo Film Co., Ltd. Negative 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
US5418127A (en) * 1993-05-28 1995-05-23 Eastman Kodak Company Water-soluble disulfides in silver halide emulsions
US6764814B2 (en) 2001-02-13 2004-07-20 Eastman Kodak Company Photographic developing composition and use thereof in the development of a photographic element
US20040197716A1 (en) * 2001-02-13 2004-10-07 Magee Paul M. Photographic developing composition and use thereof in the development of a photographic element
US6927021B2 (en) 2001-02-13 2005-08-09 Eastman Kodak Company Photographic developing composition and use thereof in the development of a photographic element

Also Published As

Publication number Publication date
JPS4838137A (de) 1973-06-05
FR2152993A1 (de) 1973-04-27
FR2152993B1 (de) 1980-07-25
DE2244916A1 (de) 1973-03-22
BE788685A (nl) 1973-03-12
GB1383640A (en) 1974-02-12

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