GB702247A - Oxonol dyes and photographic silver halide emulsions containing them - Google Patents

Oxonol dyes and photographic silver halide emulsions containing them

Info

Publication number
GB702247A
GB702247A GB11260/52A GB1126052A GB702247A GB 702247 A GB702247 A GB 702247A GB 11260/52 A GB11260/52 A GB 11260/52A GB 1126052 A GB1126052 A GB 1126052A GB 702247 A GB702247 A GB 702247A
Authority
GB
United Kingdom
Prior art keywords
thiazolone
prepared
methineoxonol
ethylthio
octylthio
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
GB11260/52A
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.)
Kodak Ltd
Original Assignee
Kodak Ltd
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 Kodak Ltd filed Critical Kodak Ltd
Publication of GB702247A publication Critical patent/GB702247A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

Abstract

N-Thiocarbo-n-tetradecoxyglycine is prepared by adding powdered potassium hydroxide to a solution of tetradecanol in carbon disulphide, adding the dried product to methanol, adding ethyl bromide, warming, diluting with water, refluxing the product with glycine, KOH, ethanol, and water, and acidifying. The corresponding ethyl, isopropyl, n-butyl, n- and tertamyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl; and g -phenyl-n-propyl compounds are similarly prepared. N-Dithiocarbo-n-octoxyglycine is prepared by shaking together glycine, carbon disulphide, and aqueous KOH, adding an ethanol solution of n-octylamine and heating, adding water, and acidifying. N-Dithiocarbo-n-dodecoxyglycine is similarly prepared. 2-Ethylthio-5-thiazolone is prepared by heating together N-dithiocarbethoxyglycine and acetic anhydride. 2-n-Octylthio-4-ethoxymethylene-5-thiazolone is prepared by heating together N-dithiocarbo-n-octoxyglycine, acetic anhydride, and ethyl orthoformate.ALSO:Oxonol dyes of the general formula <FORM:0702247/IV (c)/1> wherein R is alkyl, L a methine group, and Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing 5 or 6 atoms in the heterocyclic ring, are prepared by condensing a 2-alkylthio-5-thiazolone of the general formula <FORM:0702247/IV (c)/2> with a 4-ethoxymethylene compound of the general formula <FORM:0702247/IV (c)/3> wherein R2 is H or alkyl. The reaction may be effected in the presence of a basic condensing agent (e.g. triethylamine), with or without an inert solvent, and preferably with heating. [4-(2-Benzylthio-5-thiazolone)] [4-(2-phenyl-5-oxazolone)]-methine-oxonol is prepared by heating together 2-benzylthio-5-thiazolone, 4-ethoxymethylene-2-phenyl-5-oxazolone, ethanol, and triethylamine, diluting with water, and acidifying. [4-(2-n-Octylthio-5-thiazolone)] [4-(2-phenyl-5-oxazolone)]-methineoxonol, [4-(2-n-Octylthio-5-thiazolone)] [4-(2-acetamino-5-thiazolone)]-methineoxonol, and [4-(2-ethylthio-5-thiazolone)] [4-(2-n-octylthio-5-thiazolone)]-methylmethineoxonol are similarly prepared. [4-(2-Ethylthio-5-thiazolone)] [4-(2-n-tetradecylthio-5-thiazolone)]-methineoxonol is prepared by heating together N-dithiocarbo-n-tetradecoxyglycine, acetic anhydride, and ethyl orthoformate, removing volatile liquids under vacuum, adding 2-ethylthio-5-thiazolone, ethanol and triethylamine, heating, diluting with water, and acidifying. [4-(2-Ethylthio-5-thiazolone)] [4-(2-n-octylthio-5-thiazolone)]-methineoxonol and [4-(3-ethylthio-5-thiazolone)] [4-(2-n-dodecylthio-5-thiazolone)]-methineoxonol are similarly prepared. The preparation of bis-4-(2-ethylthio-5-thiazolone)-methineoxonol and bis-4-(2-benzylthio-5-thiazolone)-methineoxonol also is referred to. Specifications 689,025 and 700,734 are referred to.
GB11260/52A 1951-05-05 1952-05-05 Oxonol dyes and photographic silver halide emulsions containing them Expired GB702247A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US224714A US2691581A (en) 1951-05-05 1951-05-05 Photographic emulsions sensitized with oxonol dyes containing a 5(4)-thiazolone nucleus

Publications (1)

Publication Number Publication Date
GB702247A true GB702247A (en) 1954-01-13

Family

ID=22841854

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11260/52A Expired GB702247A (en) 1951-05-05 1952-05-05 Oxonol dyes and photographic silver halide emulsions containing them

Country Status (4)

Country Link
US (1) US2691581A (en)
BE (1) BE511167A (en)
FR (1) FR1078930A (en)
GB (1) GB702247A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE560452A (en) * 1956-08-30
US2965486A (en) * 1958-06-02 1960-12-20 Eastman Kodak Co Polymethine sensitizing dyes and photographic emulsions
GB939675A (en) * 1958-10-24 1963-10-16 Gevaert Photo Prod Nv New dyes and the production thereof
US3540888A (en) * 1967-11-30 1970-11-17 Eastman Kodak Co Photographic silver halide emulsions containing dyes having a 5-alkoxycarbonyl - 2,4 - dioxo-1-aryl-6-thioxopiperidene moiety

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2353164A (en) * 1944-07-11 Dyestuffs and dyestuff
FR810104A (en) * 1935-08-16 1937-03-15 Ilford Ltd Improvements to dyeing materials
US2177402A (en) * 1935-11-15 1939-10-24 Eastman Kodak Co Dye from thiazolones
US2166736A (en) * 1937-04-23 1939-07-18 Eastman Kodak Co Photographic emulsion
DE873357C (en) * 1937-04-23 1953-04-13 Kodak Ag Process for sensitizing halogen silver emulsions
US2241238A (en) * 1939-04-29 1941-05-06 Eastman Kodak Co Sensitizing methine dyes and process for preparing them
GB534140A (en) * 1939-05-25 1941-02-28 Kodak Ltd Improvements in and relating to photographic emulsions and layers, and the manufacture of dyes for use therein and intermediates for such manufacture
BE442515A (en) * 1940-07-30
US2320654A (en) * 1940-08-08 1943-06-01 Riester Oskar Sensitization of photographic emulsions
US2656353A (en) * 1950-12-29 1953-10-20 Eastman Kodak Co Sensitizing dyes containing a 2-thio-2, 5 (3, 4)-thiazoledione nucleus

Also Published As

Publication number Publication date
FR1078930A (en) 1954-11-24
US2691581A (en) 1954-10-12
BE511167A (en)

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