GB646137A - Improvements in and relating to the sensitising of photographic emulsions and to thepreparation of dyestuffs therefor - Google Patents

Improvements in and relating to the sensitising of photographic emulsions and to thepreparation of dyestuffs therefor

Info

Publication number
GB646137A
GB646137A GB11832/47A GB1183247A GB646137A GB 646137 A GB646137 A GB 646137A GB 11832/47 A GB11832/47 A GB 11832/47A GB 1183247 A GB1183247 A GB 1183247A GB 646137 A GB646137 A GB 646137A
Authority
GB
United Kingdom
Prior art keywords
ethyl
reaction product
methyl
thio
sulphate
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
GB11832/47A
Inventor
Andre Emile Van Dormael
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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 Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Publication of GB646137A publication Critical patent/GB646137A/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
    • G03C1/26—Polymethine chain forming part of a 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
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/0025—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through an oxygen atom
    • 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
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • C09B23/0083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring the heteroring being rhodanine in the chain

Landscapes

  • 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)
  • Thiazole And Isothizaole Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

Abstract

Dyes of the general formula IV, wherein Y is O or S, L is an unsubstituted or substituted methine group (the several L's not necessarily having the same significance), d is 1 or 2, n is 1, 2 or 3, R and R1 are alkyl or substituted alkyl, R11 is unsubstituted or substituted alkyl or aryl, Z and Z1 are the non-metallic atoms to complete a 5- or 6-membered heterocyclic nucleus, which may have a fused-on arylene nucleus, A is substituted OH group, and X is an acid radical, are prepared by reacting a dye of formula V or a quaternary salt thereof with an intermediate of formula III. In examples, dyes are prepared by refluxing together in ethyl alcohol containing triethylamine (1) the reaction product of 5-(N1-methylbenzthiazolylidene - 21) - 2 - thio - 3 - methyl - 4-ketotetrahydrothiazole and methyl p-toluenesulphonate, and 2 - (b - methoxy : b - methyl-vinyl) <FORM:0646137/IV (c)/1> <FORM:0646137/IV (c)/2> <FORM:0646137/IV (c)/3> - benzthiazole ethyl methyl sulphate; (2) the reaction product of 5-(N1-ethylbenzthiazolylidene - 21 - ethylidene) - 2 - thio - 3 - ethyl-4 - keto - tetrahydrothiazole and dimethyl sulphate and the intermediate of (1); (3) the reaction product of 5-(N1-ethylbenzthiazolylidene - 21) - b - phenylethylidene) - 2 - thio - 3-allyl - 4 - ketotetrahydrothiazole and dimethyl sulphate, and 2 - (b - ethoxy : b - methylvinyl) - benzselenazole diethyl sulphate; and (4) the reaction product of 5-(N1-methylquinolylidene - 21) - 2 - thio - 3 - ethyl - 4-ketotetrahydrothiazole and dimethyl sulphate, and the intermediate of (1); and by refluxing in acetic anhydride containing triethylamine (5) the reaction product of 5-(N1-methylbenzthiazolylidene - 21) - 2 - thio - 3 - ethyl - 4-ketotetrahydroxazole and dimethyl sulphate, and the intermediate of (1). Samples have been furnished under Sect. 2 (5) of dyes obtained by reacting together (1) 3-ethyl-5-(N1-methylbenzthiazolylidene - 21) - rhodanine, 2 - acetylmethylene - N - ethyl - 2 : 3 - dihydrobenzthiazole, and methyl p-toluene sulphonate; (2) the reaction product of 3-ethyl-5-(N1-ethylbenzthiazolylidene - 21) - D - butadienylidenerhodanine and dimethylsulphate, and 2-(b -methoxy : b - methylvinyl) - benzthiazole ethyl methylsulphate, and (3) the reaction product of 3-ethyl-5-(N1-methylquinolylidene-41)-rhodanine and dimethyl sulphate, and 2-(b -methoxy : b - methylvinyl) - benzthiazole ethyl methyl sulphate, the dye being precipitated in each case with aqueous KBr solution. Specification 633,824 is referred to.
GB11832/47A 1955-09-13 1947-05-02 Improvements in and relating to the sensitising of photographic emulsions and to thepreparation of dyestuffs therefor Expired GB646137A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE837674X 1955-09-13

Publications (1)

Publication Number Publication Date
GB646137A true GB646137A (en) 1950-11-15

Family

ID=3881885

Family Applications (2)

Application Number Title Priority Date Filing Date
GB11832/47A Expired GB646137A (en) 1955-09-13 1947-05-02 Improvements in and relating to the sensitising of photographic emulsions and to thepreparation of dyestuffs therefor
GB27867/56A Expired GB837674A (en) 1955-09-13 1956-09-12 Improvements in or relating to the sensitization of photographic emulsions

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB27867/56A Expired GB837674A (en) 1955-09-13 1956-09-12 Improvements in or relating to the sensitization of photographic emulsions

Country Status (4)

Country Link
BE (1) BE541245A (en)
DE (1) DE1024800B (en)
FR (1) FR1156729A (en)
GB (2) GB646137A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5034303A (en) * 1989-06-16 1991-07-23 Eastman Kodak Company Infrared absorbing trinuclear cyanine dyes for dye-donor element used in laser-induced thermal dye transfer

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3507649A (en) * 1967-01-31 1970-04-21 Lee C Hensley Sensitized photoconductive zinc oxide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918308C (en) * 1944-03-18 1954-09-23 Agfa Ag Fuer Photofabrikation Process for sensitizing halogen silver emulsions, especially chlorine and bromide silver emulsions for photographic papers, with the aid of merocyanines
DE832393C (en) * 1947-05-02 1952-02-25 Gevaert Photo Prod Nv Methods for sensitizing or supersensitizing photographic emulsions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5034303A (en) * 1989-06-16 1991-07-23 Eastman Kodak Company Infrared absorbing trinuclear cyanine dyes for dye-donor element used in laser-induced thermal dye transfer

Also Published As

Publication number Publication date
GB837674A (en) 1960-06-15
FR1156729A (en) 1958-05-20
DE1024800B (en) 1958-02-20
BE541245A (en)

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