US3801330A - Photographic silver halide recording material - Google Patents

Photographic silver halide recording material Download PDF

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Publication number
US3801330A
US3801330A US00210120A US3801330DA US3801330A US 3801330 A US3801330 A US 3801330A US 00210120 A US00210120 A US 00210120A US 3801330D A US3801330D A US 3801330DA US 3801330 A US3801330 A US 3801330A
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United States
Prior art keywords
silver halide
material according
photosensitive material
pyrazolidin
agent
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US00210120A
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English (en)
Inventor
R Ceulemans
E Brinckman
F Heugebaert
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Agfa Gevaert NV
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Agfa Gevaert NV
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • 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
    • G03C1/43—Processing agents or their precursors, not covered by groups G03C1/07 - G03C1/42

Definitions

  • mercaptans such as thiosalicylic acid and 1-phenyl5- mercaptotetrazole have been proposed. These mercaptans appear to react with the residual silver halide and form a much less light-sensitive silver salt than the original silver halide.
  • photosensitive silver halide recording materials are used in a dry pro cessing comprising a heat-development of a latent silver image by means of a reducing agent suited for the heat development of photoexposed silver halide whereupon the produced silver images are stabilized'by means of a heterocyclic sulphur compound correspondingto the following general'formula or the mutemeric thiol structure thereof:
  • Particularly suited stabilizing agents are those having the structural formulae mentioned in the following Table.
  • H Can be prepared, e.g. according to /N ⁇ Ber. 5 (1872), 240.
  • N-allylethylenediamine prepared as described in .I. Am. Chem. Soc. 67 (1945) 158 l and 80 ml of methylcellosolve 36.5 g (0.48 mole) of carbon disulphide were added dropwise with stirring at 50C. A white precipitate formed. On boiling the reaction mixture is dissolved while hydrogensulphide evolved. The solution was cooled at C and the precipitate filtered with suction. Yield 50.9 g. Melting point 8788C.
  • These stabilizing agents may be used as separate compounds or in admixture. They may be used in the photosensitive layer containing the silver halide or in an adjacent layer from which they can come in effective contact with the silver halide during the coating or heat-development step.
  • Preferred developing agents for reducing exposed silver halide with the aid of heat are pyrazolidin-3-one derivatives that have reducing properties.
  • Other developing agents suited for the purpose are, e.g., aromatic polyhydroxy compounds and their reducing derivatives such as hydroquinone, pyrogallol, resorcinol, 2,3-dihydroxy-naphthalene and pyrocatechol, aromatic hydroxy-amino compounds and their reducing derivatives such as p-aminophenol hydrochloride, p-methylaminophenol sulphate, p-hydroxyphenylglycin and 8- hydroxyl ,2,3 ,4-tetrahydroquinoline; aromatic polyamino compounds and their reducing derivatives such as p-phenylene-diamine and 4,4-diaminodiphenylamine; 3-aminopyrazoline derivatives that have reducing properties such as l-phenyl-3- aminopyrazoline.
  • Pyrazolidin-3-one developing agents that are particularly suited for use according to the present invention correspond to the following general formula:
  • R represents an aryl group including a substituted aryl group e.g. phenyl, a-naphthyl or ,B-napthyl including substituted aryl e.g. substituted by alkyl such as methyl, aralkyl such as benzyl, alkoxy such as methoxy, amino, dialkylamino, halogen such as bromine and chlorine, hydroxyalkyl, hydroxy or acetamido, or a heterocyclic group, R represents hydrogen or an acyl group e.g. an acetyl group,
  • each of R R and R represents hydrogen, an alkyl group including a substituted alkyl group, or an aryl group including a substituted aryl group, and
  • R represents hydrogen, an alkyl group preferably comprising at most 4 C-atoms, an alkoxy group preferably comprising at most 4 C-atoms, an aralkoxy group, an aryloxy group, or an aryl group including a substituted aryl group.
  • R can be benzothiazolyl or an aryl group of the benzene or the naphthalene series, either substituted or not.
  • the R R R and R are preferably hydrogen atoms or alkyl groups containing from 1 to 4 carbon atoms or aryl groups such as phenyl or naphthyl, either substituted or not.
  • an auxiliary developing agent may be used.
  • l-p-hydroxyphenyl-4,4-dim ethyl-pyrazolidin-B-one 24.
  • l-phenyl-4,4-dihydroxymethyl-pyrazolidin-3 -one 33 l-phenyl-4,4-dimethyl-S-methoxy-pyrazolidin- 3 -one 34.
  • l-phenyl-4,4-dimethyl-S-ethoxy-pyrazolidin-3-one 3 5 l-phenyl-4,4-dimethyl-5 -n-propoxy'-pyrazoliding i l-phenyl-4,4-dimethyl-5isopropoxy-pyrazoliding i l-phenyl-4,4-dimethyl-5-benzyloxy-pyrazolidinis?
  • l-aryl-pyrazolidin-B-one compounds of use according to the present invention can be prepared according to techniques known in the art, e.g. as described in the United States Patent Specifications 3,330,839 of Jozef Frans Willems, Albert Lucien Foot and Raymond Albert Roosen, issued July 1 1, 1967 and US Pat. No. 2,772,982 of Vincent C. Vesce, issued Dec. 4, 1956.
  • the silver halide emulsion layers suited for heat development by means of a pyrazolidin-3-one developing agent may contain an alkaline substance as described in'the United Kingdom Patent Specification 930,572 mentioned above, but have not to contain such substance to yield a photographic silver image as described in the United Kingdom Patent Specification 1,001,702 mentioned above.
  • a pyrazolidin-3-one is used in alkaline medium in combination with, e.g. hydroquinone as an auxiliary developing agent, less of the pyrazolidin-S-one is necessary to maintain high development activity and thus silver images can be produced with a minimum of heat energy.
  • An alkaline substance may be advantageous for accelerating the development of the latent image and such substance is therefore either present in the silver halide emulsion layer or in an adjacent layer from which on heating it can penetrate into the silver halide emulsion layer containing the pyrazolidin-3-one developing agent.
  • the alkaline substances which may be employed in the sensitive materials together with the developing agents, include inorganic substances that when dissolved in water can yield a pH above 7 such as sodium hydroxide, sodium carbonate, sodium metaborate, sodium sulphite and organic alkaline substances such as aliphatic amines, e.g. ethanolamine and ethylenediamine or heterocyclic amines, e.g. morpholine and quaternary ammonium bases.
  • Additional ingredients which may be present in the light-sensitive silver halide emulsion layer or in a layer wherefrom they can come in effective contact with the silver halide, are substances having a plurality of aliphatic ether and/or hydroxyl groups such as are present in polymers containing oxyalkylene e.g. oxyethylene groups, and aliphatic polyols of which glycerol and the non-reducing oligosaccharides, e.g. sucrose and raffinose, are particularly useful for enhancing the development activity.
  • the lightsensitive material may contain likewise a compound or compounds liberating water on heating, e.g. salts that contain a high amount of crystal water and can easily set free a certain amount thereof as e.g. sodium carbonate-lO-water or that contain a high amount of water in adsorbed or absorbed state as present, e.g., in a clathrate structure, or simply contain water associated with a hygroscopic compound, e.g. glycerol or polyethylene glycols.
  • a compound or compounds liberating water on heating e.g. salts that contain a high amount of crystal water and can easily set free a certain amount thereof as e.g. sodium carbonate-lO-water or that contain a high amount of water in adsorbed or absorbed state as present, e.g., in a clathrate structure, or simply contain water associated with a hygroscopic compound, e.g. glycerol or polyethylene glycols.
  • the recording layer having a pH of 7 or less preferably contains from 0.1 mole to 2 moles of pyrazolidin-3-one developing agent per mole of silver halide.
  • auxiliary developing agents such as those containing ascorbic acid may be used in amounts of 30-100 g per mole of silver halide and the aromatic polyhydroxy developing agents such as hydroquinone in the range of 15 to g per mole of silver halide.
  • the saccharides and polymeric oxyalkylene compounds may be used in amounts ranging from 30 to 600 g per mole of silver halide.
  • the post-exposure stabilizing agent of the above general formulae (1) or (ll) is preferably used in a range of molar ratios of 1:2 to 2:1 with respect to the silver ha] ide.
  • photosensitive silver halide Any kind of photosensitive silver halide may be used in a recording material according to the present invention, but for reason of light-sensitive and development speed preference is given to silver bromide and silver chlorobromide emulsions.
  • the photosensitive coating composition may be applied to a paper support or film support. It may be advantageous to use a paper base having a thin foil of aluminium laminated thereto in order to have a better heat conductance in the heat-development step.
  • the heat-development of the silver halide recording materials may proceed in the range of to 200C.
  • Application of heat may be carried out in different ways, e.g. by contact with a hot substance or body such as a hot plate or rollers, by high-frequency electric field heating, Joule effect heating, or by means of a hot gas stream.
  • the development may also proceed by infra-red radiation absorbed by suitable substances present in heatconductive contact with the silver halide.
  • the silver halide emulsion layer is used, e.g., in combination with a carbon-black-containing layer from which it is separated by means of a heat-conductive white pigment layer containing, e.g., zinc oxide or titanium dioxide.
  • the exposure to infrared radiation is then carried out preferably through the rearside of the recording material.
  • EXAMPLE 1 A photographic paper support of 90 glsq.m was coated at a coverage of 75 g per sq.m with a following mixture for forming a heat-developable photosensitive silver 6 aqueous gelatin solution 200 g polyoxyethylene glycol (average molecular weight: 30 g 200) imidazolidin-Z-thione as a post-exposure stabilizing l6 g agent ethanol 240 g lphenyl-pyrazolidin-3-one l g 4 aqueous formaldehyde solution l0 ml aqueous saponinc solution 3 ml a gelatino-silver chlorobromide emulsion (50 mole 500 g percent bromide) containing 0.45 mole of silver halide per kg (average particle size of silver halide grains: 0.4 nm) The pH of the coating mixture was 5.8
  • the photosensitive layer was exposed through a microfilm halftone print in a commercial microfilm enlarging copying apparatus, and developed by heating it for 5 sec. at 140C in contact with a hot plate.
  • the obtained image had a maximum optical density of 0.62 and a minimum optical density of 0.10. It showed no background colouration after a several days exposure to daylight.
  • EXAMPLE 2 A photographic paper support of 90 g/sq.m was coated at a coverage of 100 g per sq.m with a following mixture for forming a heat-developable photosensitive silver halide recording layer:
  • the photosensitive layer was exposed in contact with a transparent halftone original.
  • the development proceeded by heating the image-wise exposed material for 7 sec. at 130C by conveying it between a pair of hot rollers.
  • the obtained image had a maximum density of 0.93 and a minimum density of 0.08 and proved to be stable under overall daylight exposure for several weeks.
  • EXAM PLE 7 A photographic paper support of 90 g/sq.m was coated at a coverage of g per sq.m with a following mixture for forming a heat-developable photosensitive silver halide recording layer:
  • EXAMPLE 8 A photographic paper support of g/sq.m was coated at a coverage of 132 g per sq.m with a following mixture for forming a heat-developable photosensitive silver halide recording layer:
  • aqueous gelatin solution 220 ml fi-methyl-tetrahydro-l,3-thiazine-2-thione 20 g ethanol 240 ml l-phenyI-pyrazolidin-3-0nc 10 g 4 aqueous formaldehyde solution 10 ml 12 aqueous saponine solution 3 ml a gelatino-silvcr chloro-bromide emulsion (50 mole 300 g bromide) containing 0.55 mole of silver halide per kg (average particle size of silver halide grains: 0.4 nm) 25 aqueous ethanolamine solution
  • the pH of the coating mixture was 8.0
  • the obtained image had a maximum density of 0.91 and a minimum density of 0.09. It proved to be stable under normal daylight conditions.
  • EXAMPLE 9 A photographic paper support of 90 g/sq.m was coated at a coverage of g per sq.m with a following mixture for forming a heat-developable photosensitive silver halide recording layer:
  • the dispersion obtained was adjusted to a pH of 8 by addition of 1N sodium hydroxide whereupon 340 g of a mixed galatino-silver chlorobromoiodide emulsion (approximately 55/42.5/2.5 percent) were added containing 0.49 mole of silver halide per kg (the silver halide grains sizing 0.4 nm on the average).
  • the photosensitive material was exposed through a transparent halftone original and developed by heating said material for 5 sec at 140C in contact with a hot plate. A visible image was obtained with a maximum density of 0.54 and a minimum density of 0.10. It proved to be stable under normal daylight conditions.
  • EXAMPLES l4 EXAMPLE A photographic paper support of 90 g/sq.m was coated at a coverage of 125 g per sq.m with the following mixture for forming a heat-developable photosensitive silver halide recording layer:
  • aqueous gelatin solution 350 g polyoxyethylene glycol (molecular weight: ca. 200) 18 g imidazoline-Z-thione 9.7 g ethanol 80 g l-phenyl-pyrazolidin-3-one 8 g 2-hydrazino-6-sulpho-benzothiazole 18 g 4 aqueous formaldehyde solution 10 ml 3 ml 12 aqueous saponine solution a gelatino-silver chlorobromide emulsion (50 mole 210 g percent bromide) containing 0.52 mole of silver halide per kg (average particle size of silver halide grains 0.4 nm) The pH of the coating mixture was 5.5.
  • the photosensitive material was exposed through a transparent halftone original and developed by heating said material for 2 sec at 140C in contact with a hot plate.
  • the obtained greyish-blue image had a maximum density of 0.85 and a minimum density of 0.15. it proved to be stable under normal daylight conditions.
  • a photosensitive heat-developable recording material comprising a support bearing at least one recording layer containing photosensitive silver halide, a reducing agent for heat-developing exposed silver halide and including a post-exposure stabilizing agent which is in effective contact with the silver halide during heat-development, the improvement wherein said stabilizing agent corresponds to the following general formula or the tautomeric thiol form thereof:
  • X represents sulphur or a -NR- group, wherein R represents hydrogen or a C -C alkyl, allyl, a B-hydroxyethyl, or phenyl group, and
  • R represents an aryl group or a heterocyclic group
  • R represents hydrogen or an acyl group
  • each of R R and R represents hydrogen, an alkyl group or an aryl group and may be similar or different, and
  • R represents hydrogen, an alkyl group, an alkoxy group, an aralkoxy group, an aryloxy group or an aryl group.
  • a photosensitive material wherein said alkaline compound is sodium formate, sodium acetate, ammonium acetate, sodium benzoate, tetramethylguanidine, aminoguanidine hydrogen carbonate, trichloroacetic acid guanidine salt, 4-amino- 2,6-dimethyl-pyrimidine, or an addition complex compound of diethylamine and 2,2-bis(4-hydroxy-2,3,5,6- tetrachlorophenyl)-propane.
  • said alkaline compound is sodium formate, sodium acetate, ammonium acetate, sodium benzoate, tetramethylguanidine, aminoguanidine hydrogen carbonate, trichloroacetic acid guanidine salt, 4-amino- 2,6-dimethyl-pyrimidine, or an addition complex compound of diethylamine and 2,2-bis(4-hydroxy-2,3,5,6- tetrachlorophenyl)-propane.
  • a process for the production of silver images which comprises information-wise exposing to electromagnetic radiation a photosensitive recording material comprising a support bearing at least one recording layer containing photosensitive silver halide, a reducing agent for heat-developing exposed silver halide and including in effective contact with the silver halide during heat-development, a post-exposure stabilizing agent corresponding to the following general formula or the tautomeric thiol form thereof:
  • X represents sulphur or a -NR- group, wherein R represents hydrogen or a C,-C alkyl, allyl, a B-hydroxyethyl, or phenyl group, and

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US00210120A 1970-12-21 1971-12-20 Photographic silver halide recording material Expired - Lifetime US3801330A (en)

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GB6063370A GB1367459A (en) 1970-12-21 1970-12-21 Photographic recording material

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US (1) US3801330A (enExample)
BE (1) BE776583A (enExample)
DE (1) DE2162714A1 (enExample)
FR (1) FR2119508A5 (enExample)
GB (1) GB1367459A (enExample)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036650A (en) * 1974-08-27 1977-07-19 Canon Kabushiki Kaisha Heat developable photosensitive material containing compounds of sulfur
US4138265A (en) * 1977-06-27 1979-02-06 Eastman Kodak Company Antifoggants in certain photographic and photothermographic materials that include silver salts of 3-amino-1,2,4-mercaptotriazole
US4168980A (en) * 1977-08-19 1979-09-25 Eastman Kodak Company Heat developable photographic material and process
US4237213A (en) * 1976-01-30 1980-12-02 Canon Kabushiki Kaisha Image forming method
US4273844A (en) * 1976-01-26 1981-06-16 Canon Kabushiki Kaisha Heat-developable photosensitive member for forming electrostatic printing masters
US4336316A (en) * 1974-10-07 1982-06-22 Fuji Photo Film Co., Ltd. Image forming method
US4678735A (en) * 1984-09-11 1987-07-07 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material with development inhibitor releaser
US4859580A (en) * 1985-02-18 1989-08-22 Fuji Photo Film Co., Ltd. Heat developable photosensitive material
US5491050A (en) * 1993-03-22 1996-02-13 Eastman Kodak Company Method of processing originating photographic elements containing tabular silver chloride grains bounded by (100) faces
US5635328A (en) * 1993-08-21 1997-06-03 Konica Corporation Light-sensitive lithographic printing plate utilizing o-quinone diazide light-sensitive layer containing cyclic clathrate compound
US6037115A (en) * 1996-05-22 2000-03-14 Eastman Kodak Company Photothermographic and thermographic films containing low levels of formate to prevent fog
EP1271233A1 (en) * 2001-06-20 2003-01-02 Eastman Kodak Company A speed addendum for photographic emulsions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0143424B1 (en) 1983-11-25 1990-06-27 Fuji Photo Film Co., Ltd. Heat-developable light-sensitive materials
JPS6325644A (ja) * 1986-07-18 1988-02-03 Konica Corp 現像処理条件変化に対応できるハロゲン化銀写真感光材料

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036650A (en) * 1974-08-27 1977-07-19 Canon Kabushiki Kaisha Heat developable photosensitive material containing compounds of sulfur
US4336316A (en) * 1974-10-07 1982-06-22 Fuji Photo Film Co., Ltd. Image forming method
US4273844A (en) * 1976-01-26 1981-06-16 Canon Kabushiki Kaisha Heat-developable photosensitive member for forming electrostatic printing masters
US4237213A (en) * 1976-01-30 1980-12-02 Canon Kabushiki Kaisha Image forming method
US4138265A (en) * 1977-06-27 1979-02-06 Eastman Kodak Company Antifoggants in certain photographic and photothermographic materials that include silver salts of 3-amino-1,2,4-mercaptotriazole
US4168980A (en) * 1977-08-19 1979-09-25 Eastman Kodak Company Heat developable photographic material and process
US4678735A (en) * 1984-09-11 1987-07-07 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material with development inhibitor releaser
US4859580A (en) * 1985-02-18 1989-08-22 Fuji Photo Film Co., Ltd. Heat developable photosensitive material
US5491050A (en) * 1993-03-22 1996-02-13 Eastman Kodak Company Method of processing originating photographic elements containing tabular silver chloride grains bounded by (100) faces
US5635328A (en) * 1993-08-21 1997-06-03 Konica Corporation Light-sensitive lithographic printing plate utilizing o-quinone diazide light-sensitive layer containing cyclic clathrate compound
US6037115A (en) * 1996-05-22 2000-03-14 Eastman Kodak Company Photothermographic and thermographic films containing low levels of formate to prevent fog
EP1271233A1 (en) * 2001-06-20 2003-01-02 Eastman Kodak Company A speed addendum for photographic emulsions
US6514682B1 (en) 2001-06-20 2003-02-04 Eastman Kodak Company Speed addendum for photographic emulsions

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FR2119508A5 (enExample) 1972-08-04
GB1367459A (en) 1974-09-18
DE2162714A1 (de) 1972-07-06
BE776583A (nl) 1972-06-13

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