Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles 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 in position 2
  • C07D277/82—Nitrogen 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
  • G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
  • G03C1/355—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
  • Y10S430/13—Antibronze agent or process

Definitions

• This invention relates to improvements in the production of photographic images, especially images on paper supports prepared from silver halide emulsions.
• Silver halide emulsions are frequently subject to image degradation during processing, that is, during development, fixing, washing, toning, or other treatment and during the moist heat to which they are subjected on drying, as when prints are subjected to ferrotyping or hot-type glazing. This degradation of the image frequently manifests itself as plumming or bronzing of the image.
• o-phenylene, o-naphthylene, etc. which may be which can be represented by the following general formula:
• D represents an arylene group, e. g. o-phenylene, o-naphthylene, etc., which may be unsubstituted or substituted, for example, with an alkyl (e. g. methyl, ethyl, etc.) and/or alkoxyl (e. g. methoxy, ethoxy, etc.) group
• R represents an alkyl group, e. g. methyl, ethyl, etc.
• R1 represents an acyl group, e. g. acetyl, propionyl, etc. can be hydrolyzed in alkaline media to give hydrolysates which not only are effective antiplumming agents, but which, upon prolonged standing, develop only a faint yellow colour and show no increase in desensitizing properties.
• an object of our invention to provide a means for preventing image degradation in an exposed silver halide emulsion. Still another object is to provide new chemical compounds. Another object is to provide a method for making these new compounds. Another object is to provide photographic silver halide emulsions containing these new compounds. Other objects will become apparent from a consideration of the following examples and description.
• the present invention provides a method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing one or more of the steps of developing, fixing, washing and drying an exposed silver halide emulsion in the presence of one or more compounds represented by the following general formula:
• D represents an arylene group, e. g.
• alkyl e. g. methyl, ethyl, etc.
• alkoxyl e. g. methoxy, ethoxy, etc.
• R represents an alkyl group, e. g. methyl, ethyl, etc.
• R2 represents a hydrogen atom or a metallic atom, such as a sodium atom, potassium atom orother alkali metal atom.
• Example 8 2-a-mercaptobutyramidobenzthiazOZe Z-aminobenzthiazole (7.5 g.) was dissolved in dioxane (50 cc.) by warming, quinoline (6.5 g.) was added, and stirring rapidly, aacetylthio butyryl chloride (9.0 g.) dripped in over 10 minutes at 25 C. Quinoline hydrochloride separated rapidly. After completed addition the mixture was stirred for 2 hours and poured into water (250 00.). A thick yellow oil was precipitated. It was taken up in chloroform and the solvent distilled oil.
• the residual oil was dissolved in ethanol (50 cc.) and a solution of sodium hydroxide (6.0 g.) in water (250 cc.) added at 25 C. After 2 minutes water (250 cc.) was added, the liquor clarified by ether extraction and the required thiol precipitated as a semisolid with dilute hydrochloric acid. This was washed by decantation, redissolved in 0.5N-sodium hydroxide, clarified by ether extraction and precipitated as a hard solid by acidification. It was collected, washed with water and air dried. From benzene it formed cream needles, M. P. 142-146 C.
• Example 8 The a-acetylthiobutyryl chloride used in Example 8 was prepared as shown in the following example:
• Example 9.a-Acetylbutyrylchloride a-Acetylthiobutyric acid (73 g.) was treated at 2025 C. with thionyl chloride (67.4 g.), stood overnight, excess thionyl chloride distilled off at 6065 C. under reduced pressure (20 mm.) and the oil distilled from the steam bath at '70- 72 C./9 mm.
• Example 9 The a-acetylthiobutyric acid used in Example 9 was prepared as shown in the following example:
• Example 10 -a-Acetylthiobutyric acid a-Mercaptobutyric acid (52 g.) was placed in a 250 cc. B-necked flask fitted with stirrer and dropping funnel and acetic anhydride (75 cc.) run in over 10 minutes at room temperature. It was stirred for minutes, then the solvent removed under reduced pressure on the steam bath. The oil was then fractionated, collected at 100 150 C./8 mm. then redistilled and collected (37 g.) at 143-149" C./8 mm.
• the method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula:
• R represents an alkyl group
• R2 represents a member selected from the group consistingof a hydrogen atom and an alkali metal atom
• D represents an arylene group
• the method of preventing image degradation of an exposed silver halide emulsion during processing which comprises performing at least one of the steps of developing, fixing, washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those represented by the following general formula;
• R represents an alkyl group containing from 1 to 2 carbon atoms
• R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
• D represents a phenylene group
• R represents an alkyl group containing from 1 to 2 carbon atoms
• R2 represents a member selected from the group consisting of a hydragon atom and'an alkalirmetal-atom
• D represents a-phenylene group
• R represents an alkyl group
• R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
• D represents anary-lene group.
• R. represents an alkyl group containing from '1' to 2 carbon atoms
• R2 represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom
• D repre'sents'a phenylene group
• R2 represents a member selected from the group consisting of a hydrogen atom and D represents an arylene group.
• R2 represents a member selected from the group consisting of a hydrogen atom and Drepresents an arylene group.
• a photographic silver halide emulsion containingjrom 2.5 grams per unit to 25 grams per unit of silver halide formed from 1000 grams of silvernitrate of acompound selected from the group consisting of 2-a-mercaptopropionamidobenzthiazole, '2-'o.-mercaptopropionamido-6- ethoxybenzthiazole, 2-a-mercaptopropionamido- 6-methoxybenzthiazo1e, 6 Ch 1QI0-2-a-II1BICaptO propionamidobenzthiazole, "zfa mercaptobutyramidob'enz'thiazole, and alkali metal salts of said compounds.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (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)

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Cited By (5)

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Citations (4)

• 0
  • BE BE510333D patent/BE510333A/xx unknown
• 1951
  • 1951-03-30 GB GB7421/51A patent/GB708065A/en not_active Expired
  • 1951-10-25 US US253206A patent/US2657136A/en not_active Expired - Lifetime
• 1952
  • 1952-03-29 FR FR1057981D patent/FR1057981A/fr not_active Expired

Patent Citations (4)

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