GB700734A - Improvements in sensitized photographic emulsions and in sensitizing dyes therefor - Google Patents

Improvements in sensitized photographic emulsions and in sensitizing dyes therefor

Info

Publication number
GB700734A
GB700734A GB4041/52A GB404152A GB700734A GB 700734 A GB700734 A GB 700734A GB 4041/52 A GB4041/52 A GB 4041/52A GB 404152 A GB404152 A GB 404152A GB 700734 A GB700734 A GB 700734A
Authority
GB
United Kingdom
Prior art keywords
thiazolone
dimethinemerocyanine
ethylthio
ethylbenzoxazole
benzylthio
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
GB4041/52A
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 GB700734A publication Critical patent/GB700734A/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
    • G03C1/22—Methine and polymethine dyes with an even number of CH groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

N-Dithiocarbo-n-octoxyglycine is prepared by adding an ethanol solution of n-octyl bromide to a solution of glycine and carbon disulphide in aqueous potassium hydroxide, heating, adding water, extracting with ether, and acidifying the aqueous layer. N-Dithiocarbo-n - hexoxyglycine, - n - heptoxyglycine, - n - decoxyglycine, - n - dodecoxyglycine, and g - phenylpropoxyglycine are similarly prepared.ALSO:Merocyanine dyes of the general formula <FORM:0700734/IV(c)/1> wherein R and R1 are alkyl or substituted alkyl, L is methine or substituted methine, n is 1 or 2, d is 1, 2, or 3, and Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing 5 or 6 atoms in the heterocyclic ring, are prepared, wherein d is 1, by condensing a compound of the general formula <FORM:0700734/IV(c)/2> with a cyclammonium quaternary salt of the general formula <FORM:0700734/IV(c)/3> wherein Y is an electronegative atom or group, e.g. Cl, Br, alkoxy, or -S-R2 (wherein R2 is alkyl or aryl) and X is an anion, and, wherein d is 2 or 3, by condensing a compound of the general formula II with a cyclammonium-quaternary salt of the general formula <FORM:0700734/IV(c)/4> wherein R3 is acyl, R4 is H or aryl, p is 1 or 2 and X is an anion [2-(3-Ethylbenzoxazole)]-[4-(2-ethylthio-5-thiazolone) ]-dimethinemerocyanine is prepared by refluxing 2-ethylthio-4-ethoxymethylene-5-thiazolone (obtained by heating together N-dithiocarbethoxyglycine, acetic anhydride, and ethyl orthoformate) with 2-methylbenzoxazole ethiodide, ethanol, and triethylamine. [2-(1-Ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-methylthiazoline) [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethyl-4-methylthiazole] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [4-(1-ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethyl-4-tolylthiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, (2-(1-ethyl-b -naphthathiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-methylthiazoline] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(1-ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethyl-4-methylthiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(1-ethylquinoline)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-2-benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - ethylbenzselenazole)] [4 - (2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - ethylbenzoxazole)] [4-(2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (1 - ethylpyridine)] [4 - (2 - benzylthio - 5 - thiazolone)]-dimethinemerocyanine, [4 - (1 - ethylquinoline)] [4 - (2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - methylthiazoline)] [4 - (2 - benzylthio-5-thiazolone)]-dimethinemerocyanine, [2 - (1 - ethyl - b - naphthathiazole)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [4-(1-methylpyridine)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [2-3-methylthiazolone)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylthiazoline)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(5-chloro-3-ethylbenzthiazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-n-[octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylthiazoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-dodecylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-hexylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-heptylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-#c-phenylpropylthio-5-thiazolone)]-dimethinemerocyanine, [2-(1-ethyl-b -naphthathiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-decylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-decylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-2-n-decylthio-5-thiazolone)]-b -ethyldimethinemerocyanine, [2-(3-ethylbenzselazole)] [4-(2-n-heptylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-tetramethinemerocyanine and [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-merocyanine are similarly prepared. Specifications 133,034, [Class 98(2)], 369,616, 408,991, 447,092, 500,611, 500,826, 541,510, 541,511, 541,512, 541,513, 541,514, 541,515 and 552,368, [all in Group XX], are referred to.
GB4041/52A 1951-02-17 1952-02-15 Improvements in sensitized photographic emulsions and in sensitizing dyes therefor Expired GB700734A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US211566A US2692829A (en) 1951-02-17 1951-02-17 Photographic emulsions sensitized with merocyanine dyes containing a 5(4)-thiazolone nucleus

Publications (1)

Publication Number Publication Date
GB700734A true GB700734A (en) 1953-12-09

Family

ID=22787448

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2229/52A Expired GB703520A (en) 1951-02-17 1952-01-28 Improvements in and relating to processes of making merocyanine dyes and to photographic silver halide emulsions containing them
GB4041/52A Expired GB700734A (en) 1951-02-17 1952-02-15 Improvements in sensitized photographic emulsions and in sensitizing dyes therefor

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2229/52A Expired GB703520A (en) 1951-02-17 1952-01-28 Improvements in and relating to processes of making merocyanine dyes and to photographic silver halide emulsions containing them

Country Status (4)

Country Link
US (1) US2692829A (en)
BE (2) BE509306A (en)
FR (2) FR1101164A (en)
GB (2) GB703520A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944901A (en) * 1957-01-18 1960-07-12 Eastman Kodak Co Multicontrast photographic emulsions

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2899430A (en) * 1959-08-11 Chxch
BE522770A (en) * 1952-09-15
US2886565A (en) * 1955-09-12 1959-05-12 Sperry Rand Corp Photographic sensitizing dyes derived from 2-alkyl-5, 6-dihydro-4-h-pyrano (3, 2d) thiazole
BE551713A (en) * 1955-10-12
BE560805A (en) * 1956-09-13
US3055952A (en) * 1957-10-09 1962-09-25 Du Pont Hydroxyl-terminated polymers
US3312570A (en) * 1961-05-29 1967-04-04 Monsanto Co Production of epitaxial films of semiconductor compound material
US3106466A (en) * 1961-06-14 1963-10-08 Horizons Inc Print-out photoprocess with merocyanine dyes
US3218204A (en) * 1962-07-13 1965-11-16 Monsanto Co Use of hydrogen halide as a carrier gas in forming ii-vi compound from a crude ii-vicompound
BE755812A (en) * 1969-09-05 1971-02-15 Fuji Photo Film Co Ltd MULTI-LAYER PHOTOSENSITIVE MATERIALS FOR COLOR PHOTOGRAPHY

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
DE873357C (en) * 1937-04-23 1953-04-13 Kodak Ag Process for sensitizing halogen silver emulsions
US2166736A (en) * 1937-04-23 1939-07-18 Eastman Kodak Co Photographic emulsion
US2282116A (en) * 1939-04-14 1942-05-05 Eastman Kodak Co Photographic element
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944901A (en) * 1957-01-18 1960-07-12 Eastman Kodak Co Multicontrast photographic emulsions

Also Published As

Publication number Publication date
FR1101164A (en) 1955-10-04
BE509307A (en)
BE509306A (en)
FR1099410A (en) 1955-09-05
US2692829A (en) 1954-10-26
GB703520A (en) 1954-02-03

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