GB556266A - Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes - Google Patents

Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes

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Publication number
GB556266A
GB556266A GB12486/41A GB1248641A GB556266A GB 556266 A GB556266 A GB 556266A GB 12486/41 A GB12486/41 A GB 12486/41A GB 1248641 A GB1248641 A GB 1248641A GB 556266 A GB556266 A GB 556266A
Authority
GB
United Kingdom
Prior art keywords
ethyl
butadienyl
ethiodide
iodide
pyrrole
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
GB12486/41A
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 GB556266A publication Critical patent/GB556266A/en
Expired legal-status Critical Current

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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
    • C09B23/10—The polymethine chain containing 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
    • C09B23/0091—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

556,266. Polymethine dyes and intermediates. KODAK, Ltd. Sept. 26, 1941, No. 12486. Convention date, Oct. 18, 1940. Samples furnished. [Class 2 (iii)] [Also in Group XX] A compound of the general formula of Fig. 1 where R represents an alkyl or aryl radical, R<SP>1</SP> represents an alkyl radical, X represents an acid radical, and Z the non-metallic atoms necessary to complete a 5- or 6- membered heterocyclic nucleus is prepared by condensing a #-alkoxyacrolein acetal with a cyclammonium quaternary salt containing a methyl group in the α-position to the nitrogen atom and employing as the reaction medium substantially anhydrous acetic acid not containing more than 1 per cent. of water. From 1 ¢ to 3 molecular proportions of acrolein acetal may be used for each molecular proportion of cyclammonium quaternary salt. The cyclammonium quaternary salt may be a quinoline, benzoxazole, naphthoxazole, benzthiazole, naphthathiazole, benzselenazole, or thiazoline derivative. The reaction medium may be glacial acetic acid and the quaternary salt an iodide. 2-(4-Ethoxy- #<SP>1</SP>:<SP>3</SP>-butadienyl)-benzthiazoleethiodide is prepared by reacting 2-methylbenzthiazole ethiodide and #-ethoxyacrolein diethyl acetal in glacial acetic acid. 2-(4-Ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-benzoxazole ethiodide, 2-(4-etlaoxy-#<SP>1</SP>:<SP>3</SP>- butadienyl)-#-naphthathiazole ethiodide, 2-(4- ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-α-naphthoxazole ethiodide, 2-(4-ethoxy-# <SP>1</SP>:<SP>3</SP>-butadienyl)-#-naphthoxazole ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-quino line ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl)-benzselenazole ethiodide, 2-(4-ethoxy- #<SP>1</SP>: <SP>3</SP>-butadienyl). thiazoline ethiodide, 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>-butadienyl). benzthiazolepheniodide, and 2-(4-ethoxy-#<SP>1</SP>:<SP>3</SP>- butadienyl) 3:4 - - trimethylene benzthiazolium iodide are similarly prepared. Polymethine dyes are prepared by condensing a compound of the general formula shown in Fig. 1 with a cyclammonium alkyl quarternary salt containing a methyl group in the α or y position to the nitrogen atom. Pyridine or trialkylamines dissolved in acetic anhydride may be used as condensing agents. 3 : 3<SP>1</SP>- Diethylthiadicarbocyanine iodide is prepared by refluxing together 2 - (4 - ethoxy - # <SP>1</SP> : <SP>3</SP> - butadienyl) - benzthiazole ethiodide and 2 - methylbenzthiazole ethiodide in pyridine. 1<SP>1</SP>: 3- Diethyloxa - 2<SP>1</SP> - dicarbocyanine iodide is similarly prepared using as condensing agent acetic anhydride containing triethylamine. 1<SP>1</SP> : 3 - - Diethylthia - 2<SP>1</SP> dicarbocyanine iodide, 1<SP>1</SP> : 3 - diethylthia - 4<SP>1</SP> - dicarbocyanine iodide 3 : 3<SP>1</SP> - diethyl - 4 : 5 benzthiadicarbocyanine iodide, 3 : 3 - diethyl - 4 5 : 4<SP>1</SP>: 5<SP>1</SP> - dibenzthiadicarbocyanine iodide, 1 : : 1<SP>1</SP> - diethyl 2 : : 2<SP>1</SP>- dicarbocyanine iodide, 3 : 3<SP>1</SP> - diethyloxadi - carbocyanine iodide, 3 : 3<SP>1</SP> - . diethyloxathiadicarbonyanine isodide, 1<SP>1</SP> : 3 - diethyloxa - 4<SP>1</SP> - dicarbocyanine iodide, 3 3<SP>1</SP> - diethylselena - dicarbocyanine iodide, 3 : 3<SP>1</SP> - diethylselenathiadicarbocyanine iodide, 3 : 3<SP>1</SP>- diethyloxaselena dicarbocyanine iodide, and 3 - ethyl - 3<SP>1</SP> - methylthiathiazolino dicarbocyanine iodide are similarly prepared. Polymethine dyes may also be prepared by condensing the compounds of the general formula of Fig. 1 with a heterocyclic compound having a methylene group adjacent to a carbonyl group. 3 - - Ethyl - 5 - [(3 - - ethyl - 2 - benzthiazolyidene) - butenylidene] - rhodanine is prepared by condensing 2 - (4 - ethoxy - #<SP> 1</SP> : 3- butadienyl) - benzthiazole ethiodide with 3 - ethylrhodanine in the presence of triethylamine and acetic anhydride. The intermediate may also be condensed with 1 - phenyl - 3 - methyl - 5 -.pyrazolone or with 1 - ethyl - 3 - phenyl - 2 - thiohydantoin. Polymethine dyes may also be prepared by condensing the intermediates with primary or secondary aliphatic or aromatic amines. 2 - (4- Piper´dino - #<SP>1</SP> : <SP>3</SP> - butadienyl)- benzthiazole ethiodide is prepared by refluxing together 2 - (4 - ethoxy - #<SP>1</SP> : 3 - butadienyl)- benzthiazole ethiodide and piperidine in ethyl alcohol. The intermediate may also be condensed with aniline. Polymethine dyes may also be obtained by condensing the intermediates with N - alkyl or N - aryl pyrroles. Such dyes may be used as light-screening substances in the preparation of photographic elements, and are bleachable in alkaline developers. (3 - - Ethyl - 2 - benzthiazole) (1 - - heptyl - 2 : 5 - dimethyl - 3 - pyrrole) - tetramethinecyanine iodide is prepared by refluxing together 2 - (4 - ethoxy - #<SP>1</SP> : 3 - butadienyl) - benzthiazole ethiodide and 1 - heptyl - 2 : 5 - dimethylpyrrole in acetic anhydride. (3 - - Ethyl - 2 - benzoxazole) (1 - - heptyl - 2 : 5 - dimethyl - 3 pyrrole-, (3 - - ethyl - 2 - benzoxaozle) (1 - lauryl - 2 : : 5 - dimethyl 3 - - pyrrole) 3 - - ethyl - 2 - benzoxazole)- (1 - ethyl - 2 : : 5 - dimethyl - 3 - pyrrole)-, (1 - cetyl - 2 : 5 - dimethyl 3 - - pyrrole) 3 - - ethyl - 2 - benzoxazole)-, (1 ethyl - 2: 5 - dimethyl - 3 - pyrrole) - (3 - ethyl - 2 - α - naphthoxazole),- (3 - - ethyl - 2 - α - - naphthoxazole) - (1 lauryl - 2 : 5 - - dimethyl 3 - pyrrole)-, (1 - ethyl - 2 : 5 - dimethyl - 3 pyrrole) (1 - - ethyl - 2 - # - naphthoxazole)-, 1 - - ethyl - 2 5 - dimethyl - 3 pyrrole)- (1 - - ethyl 2 - quinoline)-, (3 - - ethyl - 2 - benzthia; zole)- (1 - ethyl - 2 : 5 - dimethyl - 3 pyrrole)-,. (3 - - ethyl - 2 - benzthiazole)- (2 : 5 dimethyl 1- phenyl 3 - - pyrrole)-, (1 - - ethyl - 2 : 5 - dimethyl- 3 - pyrrole) - (3 - - methyl - 2 thiazoline)-, and (3 - - ethyl - 2 - - benzselenazole) (1 - - ethyl - 2 : 5- dimethyl - 3 - pyrrole) tetramethine cyanines are similarly prepared. Samples have been furnished under Sect. 2 (5) of (a) 2<SP>1</SP> - (4 - methoxy - #<SP>1</SP> :<SP>3</SP> -butadienyl)- benzoxazole ethiodide (b) 2<SP>1</SP> - (4-piperidine - # <SP>1</SP>: <SP>3</SP> - butadienyl) - benzthiazole ethiodide: (c) 2<SP>1</SP> - (4 - anilino - #<SP>1</SP> : 3 - butadienyl) - benz - thiazole ethiodide : and (d) 2<SP>1</SP> - (4 - dibutylamino - # <SP>1</SP> : <SP>3</SP> - butadienyl) - benzoxazole ethoper - chlorate. Specification 551,331 is referred to.
GB12486/41A 1940-10-18 1941-09-26 Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes Expired GB556266A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US556266XA 1940-10-18 1940-10-18

Publications (1)

Publication Number Publication Date
GB556266A true GB556266A (en) 1943-09-28

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ID=21999109

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12486/41A Expired GB556266A (en) 1940-10-18 1941-09-26 Improvements in and relating to polymethine dye intermediates and to the production of polymethine dyes

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101726579A (en) * 2008-10-17 2010-06-09 深圳迈瑞生物医疗电子股份有限公司 Blood test reagent and method
CN101602762B (en) * 2008-06-10 2013-10-16 深圳迈瑞生物医疗电子股份有限公司 Asymmetric cyanine compound, preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101602762B (en) * 2008-06-10 2013-10-16 深圳迈瑞生物医疗电子股份有限公司 Asymmetric cyanine compound, preparation method and application thereof
CN101726579A (en) * 2008-10-17 2010-06-09 深圳迈瑞生物医疗电子股份有限公司 Blood test reagent and method
CN101726579B (en) * 2008-10-17 2014-06-18 深圳迈瑞生物医疗电子股份有限公司 Blood test reagent and method

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