GB604600A - Alicyclicdioxybenzthiazole (and selenazole) carbocyanine dyestuffs and a process of preparing the same - Google Patents

Alicyclicdioxybenzthiazole (and selenazole) carbocyanine dyestuffs and a process of preparing the same

Info

Publication number
GB604600A
GB604600A GB20941/45A GB2094145A GB604600A GB 604600 A GB604600 A GB 604600A GB 20941/45 A GB20941/45 A GB 20941/45A GB 2094145 A GB2094145 A GB 2094145A GB 604600 A GB604600 A GB 604600A
Authority
GB
United Kingdom
Prior art keywords
prepared
iodide
diethyl
ethyl
ethiodide
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
GB20941/45A
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB604600A publication Critical patent/GB604600A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines

Abstract

Cyanine dyes have the general formula Cyanine dyes have the general formula <FORM:0604600/IV(b)/1> wherein R represents the methlene groups to complete a cyclopentylidene or cyclohexylidene ring, R1 and R2 are alkyl groups, Y represents S or Se, X represents an acid radical, and Z represents the atoms to complete a nitrogenous heterocyclic ring which heterocyclic ring may be substituted by alkyl, aryl (e.g. phenyl, naphthyl, or anthranyl), a hydrogenated ring system similar to that completed by R, alkoxy, or alkyl dioxy. The dyes are prepared by condensing quaternary ammonium salts of thiazoles and selenazoles containing an alicyclic dioxy ring with ethyl orthoformate or with 2 - (b - acetanilidovinyl) - 5 : 6 - methylenedioxybenzthiazole ethiodide, 2 - (b - acetanilidovinyl - 5 : 6 - cyclohexylidenedioxybenzthiazole ethiodide, or the corresponding seleno derivatives. 3 : 31-diethyl-5 : 6 : 51 : 61-dicyclohexylidenedioxybenzthiacarbocyanine iodide is prepared by reacting 2-methyl-5 : 6-cyclohexylidenedioxybenzthiazole ethyl p-toluenesulphonate with ethyl orthoformate in the presence of pyridine and triethylamine, and adding aqueous potassium iodide to the hot n-propyl alcohol solution of the product. 3 : 31-Diethyl-5 : 6 : 51 : 61-dicyclopentylidenedioxybenzthiacarbocyanine iodide is similarly prepared. 3 : 31-Diethyl-5 : 6-cyclohexylidenedioxy - 51 : 61 - methylenedioxybenzthiacarbocyanine iodide is prepared by refluxing together 2 - (b - acetanilidovinyl) - 5 : 6 - methylenedioxybenzthiazole ethiodide, 2-methyl-5 : 6-cyclohexylidenedioxybenzthiazole ethyl - p - toluenesulphonate, pyridine, and triethylamine. 3 : 31-Diethyl -5 : 6-cyclohexylidenedioxy-51 : 61-methylenedioxybenzthiabenzselenacarbocyanine iodide, 3 : 31-diethyl-5 : 6-cyclohexylidenedioxy-61 : 71-benzbenzthiacarbocyanine iodide, and 3 : 31-diethyl-5 : 6-cyclohexylidenedioxy-51 : 61-dimethoxybenzthiacarbocyanine iodide are similarly prepared. Alicyclic-dioxybenzenes are prepared by reacting catechol with cyclic ketones. Cyclohexylidenediozybenzene is prepared by treating a solution of catechol in hot anhydrous cyclohexanone with excess phosphoric anhydride. Cyclopentylidenedioxybenzene is similarly prepared. 1 : 2 - Dinitro - 4 : 5 - cyclohexylidenedioxybenzene is prepared by treating cyclohexylidenedioxybenzene with a mixture of glacial acetic and fuming nitric acids. 1 : 2-Dinitro-4 : 5-cyclopentylidenedioxybenzene is similarly prepared. 2 : 21-Dinitro-5 : 6 : 51 : 61-di-(cyclohexylidenedioxybenzene) disulphide is prepared by adding a fused mixture of sodium sulphide and sulphur to a boiling ethyl alcohol solution of 1 : 2-dinitro4 : 5 - cyclohexylidenedioxybenzene. 2 : 21 - Dinitro-5 : 6 : 51 : 61-di-(pentylidenedioxybenzene) disulphide is similarly prepared. 2 - Methyl - 5 : 6 - cyclohexylidenedioxybenzthiazole is prepared by adding zinc dust to a heated mixture of 1 : 2-dinitro-4 : 5-cyclohexylidenedioxybenzene disulphide, acetic anhydride, acetic acid, and acetyl chloride. 2-Methyl-5 : 6-cyclopentylidenedioxybenzthiazole and 2-methyl-5 : 6 - methylenedioxybenzselenazole are similarly prepared. The ethyl p-toluenesulphonates are prepared in the usual manner. 2 - (b - Acetanilidovinyl) - 5 : 6 - methylenedioxybenzthiazole ethiodide is prepared by heating together 2 - methyl - 5 : 6 - methylenedioxybenzthiazole ethiodide, diphenylformamidine and acetic anhydride. 2-(b -Acetanilidovinyl)-5 : 6 - cyclohexylidenebenzthiazole ethiodide is similarly prepared.ALSO:Cyanine dyes have the general formula <FORM:0604600/IV (c)/1> wherein R represents the methylene groups to complete a cyclopentylidene or cyclohexylidene ring, R1 and R2 are alkyl groups, Y represents S or Se, X represents an acid radical, and Z represents the atoms to complete a nitrogenous heterocyclic ring, which heterocyclic ring may be substituted by alkyl, aryl (e.g. phenyl, naphthyl, or anthranyl), a hydrogenated ring system similar to that completed by R, alkoxy, or alkyl dioxy. The dyes are prepared by condensing quaternary ammonium salts of thiazoles and selenazoles containing an alicyclic dioxy ring with ethyl orthoformate or with 2 - (b - acetanilidovinyl) - 5 : 6 - methylenedioxybenzthiazole ethiodide, 2 - (b - acetanilidovinyl - 5 : 6 - cyclohexylidenedioxybenzthiazole ethiodide, or the corresponding seleno derivatives. 3 : 31 - Diethyl - 5 : 6 : 51 : 61 - di - cyclohexylidenedioxybenzthiacarbocyanine iodide is prepared by reacting 2-methyl-5 : 6-cyclohexylidenedioxybenzthiazole ethyl p-toluenesulphonate with ethyl orthoformate in the presence of pyridine and triethylamine, and adding aqueous potassium iodide to the hot n-propyl alcohol solution of the product. 3 : 31 - Diethyl - 5 : 6 : 51 : 61 - dicyclopentylidene-dioxybenzthiacarbocyanine iodide is similarly prepared. 3 : 31 - Diethyl-5 : 6-cyclohexylidene-dioxy - 51 : 61 - methylenedioxybenzthiacarbocyanine iodide is prepared by refluxing together 2 - (acetanilidovinyl) - 5 : 6 - methylenedioxy - benzthiazole ethiodide, 2 - methyl - 5 : 6 - cyclohexylidenedioxybenzthiazole ethyl - p - toluenesulphonate, pyridine, and triethylamine 3 : 31-Diethyl- 5 : 6-cyclohexylidenedioxy-51 : 61 - methylenedioxybenzthiabenzselenacarbocyanine iodide, 3 : 31-diethyl-5 : 6-cyclohexylidenedioxy-61 : 71-benzbenzthiacarbocyanine iodide, and 3 : 31-diethyl-5 : 6-cyclohexylidenedioxy-61 : 71\h - benzbenzthiacarbocyanine iodide, and 3 : 31 - di - ethyl - 5 : 6 - cyclohexylidenedioxy - 51 : 61 - dimethoxybenzthiacarbocyanine iodide are similarly prepared.
GB20941/45A 1944-08-16 1945-08-14 Alicyclicdioxybenzthiazole (and selenazole) carbocyanine dyestuffs and a process of preparing the same Expired GB604600A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US54978944A 1944-08-16 1944-08-16

Publications (1)

Publication Number Publication Date
GB604600A true GB604600A (en) 1948-07-07

Family

ID=24194390

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20941/45A Expired GB604600A (en) 1944-08-16 1945-08-14 Alicyclicdioxybenzthiazole (and selenazole) carbocyanine dyestuffs and a process of preparing the same

Country Status (2)

Country Link
US (1) US2429574A (en)
GB (1) GB604600A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0521632A1 (en) * 1991-06-26 1993-01-07 Konica Corporation Silver halide photographic materials
JP2877579B2 (en) * 1991-08-26 1999-03-31 コニカ株式会社 Silver halide color photographic materials

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2334711A (en) * 1943-11-23 Ctanine dyestdff intermediates
US2126078A (en) * 1932-04-26 1938-08-09 Agfa Ansco Corp Sensitizing photographic emulsion

Also Published As

Publication number Publication date
US2429574A (en) 1947-10-21

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