GB629106A - Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes - Google Patents

Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes

Info

Publication number
GB629106A
GB629106A GB553246A GB553246A GB629106A GB 629106 A GB629106 A GB 629106A GB 553246 A GB553246 A GB 553246A GB 553246 A GB553246 A GB 553246A GB 629106 A GB629106 A GB 629106A
Authority
GB
United Kingdom
Prior art keywords
ethyl
ethylbenzthiazole
ethylquinoline
dyes
dianiloisopropylidene
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
GB553246A
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.)
BARBARA SEATON WINTON
Kodak Ltd
Original Assignee
BARBARA SEATON WINTON
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 BARBARA SEATON WINTON, Kodak Ltd filed Critical BARBARA SEATON WINTON
Priority to GB553246A priority Critical patent/GB629106A/en
Publication of GB629106A publication Critical patent/GB629106A/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
    • C09B23/12—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being branched "branched" means that the substituent on the polymethine chain forms a new conjugated system, e.g. most trinuclear cyanine dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

A heterocyclic ternary nitrogen base having a dianiloisopropylidene group in the a - or g -position to the ternary nitrogen atom is prepared by condensing a compound of the formula Ar1-N=CH-OR1, wherein Ar1 is an unsubstituted or substituted phenyl group and R1 is an alkyl, substituted alkyl, or unsaturated aliphatic group, with a heterocyclic ternary nitrogen base having a methylene or aniloethylidene group attached to the carbon atom in the a - or g -position to the ternary nitrogen atom, by heating together in the presence of a water-binding agent, e.g. zinc chloride. Numerous methylene and aniloethylidene bases are specified. 3 - Ethyl - 2 - dianiloisopropylidenebenzthiazoline is prepared by heating together 3-ethyl-2-methylenebenzthiazoline or 3-ethyl-2-aniloethylidenebenzthiazoline, ethylisoformanilide, and zinc chloride. 5-Chloro-3-ethyl-2-aniloisopropylidenebenzthiazoline, 3 - ethyl - 2 - dianiloisopropylidene - 6 : 7 - benzbenzthiazoline, 3 - ethyl - 2 - dianiloisopropylidenebenzselenazoline, 4 -methyl - 3 - ethyl - 2 - dianiloisopropylidene - D 4 - thiazoline, 3 - methyl - 2 - dianiloisopropylidenethiazolidine, 3 - ethyl - 2 - aniloisopropylidenethiazolidine, 1 - ethyl - 4 - dianiloisopropylidene - 1 : 4 - dihydroquinoline, 1 - ethyl - 2- dianiloisopropylidene - 1 : 2 - dihydroquinoline, and 3 - ethyl - 2 - dianiloisopropylidenebenzoxazoline are similarly prepared.ALSO:Polymethine dyes are prepared by condensing a heterocyclic ternary nitrogen base having a dianiloisopropylidene group in the a - or g -position to the ternary nitrogen atom with a quaternary salt of a heterocyclic nitrogen compound having a methyl group in the a - or g -position to the quaternary nitrogen atom by heating together in presence of a condensing agent, the time and temperature of heating being sufficient to cause one molecular proportion of the base to combine with two molecular proportions of the quaternary salt to give a dye of probable general formula P1(R2)=C(CH=P2(R3)X)2, wherein P1(R2) and P2(R3) represent the residues of heterocyclic nitrogen compounds connected in the a - or g -position to the N atoms to which the groups R2 and R3 are attached, (R2 and R3 being alkyl, aralkyl, or aryl groups) and X represents an anion. [Bis - 2 - (3 - ethylbenzthiazole)] [a : b 1 - dimethine - 21 - (31 - ethylbenzthiazole)] - trimethinecyanine di-iodide is prepared by heating together 3 - ethyl - 2 - dianiloisopropylidenebenzthiazoline and 2-methylbenzthiazole ethiodide in pyridine. Dyes may be similarly obtained in which the three nuclei are 2-(3-ethyl-6 : 7-benzbenzthiazole), 2 - (5 - chloro - 3 - ethylbenzthiazole), 2 - (3 - ethylbenzselenazole), 2 - (4 - methyl - 3-ethylthiazole), 2 - (3 - methyl - D 2 - thiazoline), 2 - (3 - ethyl - D 2 - thiazoline), 2 - (1 - ethylquinoline) and 4-(1-ethylquinoline). Dyes may also be similarly obtained in which one nucleus is 4-(1-ethylquinoline) and the other two 2-(1-ethylquinoline) or 2-(3-ethyl-D 2-thiazoline), or one 2-(3-ethylbenzthiazole) and the other two 4 - (1 - ethylquinoline), 2 - (1 - ethylquinoline), 2 - (3 - ethylbenzoxazole), 2 - (3 - ethylbenzselenazole), or 5 - (3 - ethylrhodanine), or one 2 - (3 - ethylbenzselenazole) and the other two 2 - (1 - ethylquinoline), 2 - (3 - ethylbenzoxazole), 2 - (3 - ethylbenzthiazole), 2 - (3 - ethyl-6 : 7 - benzbenzthiazole), 2 - (1 : 3 : 3 - trimethylindolenine), 5 - (3 - ethylrhodanine), or 5 - (4 - keto - 2 - thio - 3 - ethyltetrahydro-oxazole), or one 2 - (4 - methyl - 3 - ethylthiazole) and the other two 2-(3-ethylbenzthiazole), 2 - (3 - ethylbenzselenazole), 5 - (3-ethylrhodanine), or 5 - (4 - keto - 2 - thio - 3-ethyltetrahydro-oxazole), or one 2-(3-ethyl-D 2-thiazoline) and the other two 2-(3-ethylbenzthiazole), 4 - (1 - ethylquinoline), or 5-(4 - keto - 2 - thio - 3 -ethyltetrahydrooxazole),-or one 2 - (5 - chloro - 3 - ethylbenzthiazole) and the other two 5-(3-ethylrhodanine), 5-1) - phenyl - 3 - ethyl - 2 - thiohydantoin), or 5 - (2 - diphenylamino - 4 - keto - D 2 - thiazoline) Specifications 408,272, [Group XX], 408,273, 561,172, 585,707, 629,122 and 629,123 are referred to.
GB553246A 1946-02-22 1946-02-22 Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes Expired GB629106A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB553246A GB629106A (en) 1946-02-22 1946-02-22 Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB553246A GB629106A (en) 1946-02-22 1946-02-22 Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes

Publications (1)

Publication Number Publication Date
GB629106A true GB629106A (en) 1949-09-13

Family

ID=9797978

Family Applications (1)

Application Number Title Priority Date Filing Date
GB553246A Expired GB629106A (en) 1946-02-22 1946-02-22 Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes

Country Status (1)

Country Link
GB (1) GB629106A (en)

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