GB671346A - Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them - Google Patents

Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them

Info

Publication number
GB671346A
GB671346A GB102649A GB102649A GB671346A GB 671346 A GB671346 A GB 671346A GB 102649 A GB102649 A GB 102649A GB 102649 A GB102649 A GB 102649A GB 671346 A GB671346 A GB 671346A
Authority
GB
United Kingdom
Prior art keywords
thiazolidone
methylene
phenyl
prepared
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB102649A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to GB102649A priority Critical patent/GB671346A/en
Publication of GB671346A publication Critical patent/GB671346A/en
Expired legal-status Critical Current

Links

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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A methine dye of the general formula <FORM:0671346/IV (c)/1> wherein Z represents the atoms necessary to complete the nucleus of a benzthiazole, benzselenazole, a - or b -naphthathiazole, quinoline, thiazoline, thiazole, or 3 : 3-dimethylindolenine, R is alkyl (or where Z completes a benzthiazole or thiazoline nucleus, alkyl or aryl), R2 is aryl, n is 0 or 1, and X is a halogen atom, is prepared by condensing a halogeno ester of the general formula X-CH2-CO-O-R1 wherein R1 is alkyl or aryl, with a compound of the general formula <FORM:0671346/IV (c)/2> 2 - [(2 - Benzthiazolyl ethiodide) - methylene]-3 - phenyl - 4 - thiazolidone is prepared by heating together 2-(2-anilino-2-thioethylidene)-3-ethylbenzthiazoline and ethyl bromoacetate, dissolving the product in hot methanol, and adding aqueous potassium iodide. The corresponding ethochloride is prepared by using ethyl chloracetate, or by treating the ethiodide with silver chloride. 2-[(2-b -Naphthathiazolyl ethobromide) - methylene] - 3 - phenyl - 4 - thiazolidone and the corresponding ethochloride, 2 - [(2 - quinolyl ethoperchlorate) - methylene] - 3-phenyl - 4 - thiazolidone, 2 - [(2 - benzselenazolyl ethiodide) - methylene] - 3 - phenyl - 4 - thiazolidone, 2 - {[2 - (4 - methylthiazolyl) - ethiodide]-methylene} - 3 - phenyl - 4 - thiazolidone, and 2-[(4 - quinolyl ethoperchlorate) - methylene] - 3-phenyl-4-thiazolidone are similarly prepared. A dye of the general formula <FORM:0671346/IV (c)/3> wherein R6 and R7 each represent an alkyl group, is prepared by condensing a dye of the first general formula with a p-dialkylaminobenzaldehyde. 2 - [(Benthiazolyl ethochloride) - methylene]-5- p - dimethylaminobenzylidene - 3 - phenyl - 4-thiazolidone is prepared by refluxing together 2- [(2 - benzthiazolyl ethochloride) - methylene] - 3 - phenyl - 4 - thiazolidone and p-dimethylaminobenzaldehyde in ethanol containing piperidine. 5-p-Dimethylaminobenzylidene - 2 - [(2 - b - naphthathiazolyl ethochloride)-methylene] - 3 - phenyl - 4 - thiazolidone is similarly prepared. Dyes are also prepared by condensing dyes of the first general formula with alkyl orthoformates. In examples, 2-[(2-benzthiazolyl ethobromide) - methylene] - 3 - phenyl - 4-thiazolidone and ethyl orthoformate are refluxed together in pyridine, and a concentrated solution of the product is treated with aqueous potassium iodide, and 2-[(2-b -naphthathiazolyl ethobromide) - methylene] - 3 - phenyl - 4-thiazolidone and ethyl orthoformate are refluxed together in pyridine containing triethylamine, and a concentrated solution of the product is treated with aqueous potassium iodide. Specifications 533,238, 546,705, 551,331, 551,824, 566,010, 618,073, 646,896, 646,900, 647,542 and 649,725 are referred to.
GB102649A 1949-01-13 1949-01-13 Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them Expired GB671346A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB102649A GB671346A (en) 1949-01-13 1949-01-13 Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB102649A GB671346A (en) 1949-01-13 1949-01-13 Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them

Publications (1)

Publication Number Publication Date
GB671346A true GB671346A (en) 1952-04-30

Family

ID=9714849

Family Applications (1)

Application Number Title Priority Date Filing Date
GB102649A Expired GB671346A (en) 1949-01-13 1949-01-13 Process for preparing methin dyes containing a 3-aryl-4-thiazolidone nucleus and photographic emulsions containing them

Country Status (1)

Country Link
GB (1) GB671346A (en)

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