Patent GB-742112-A (GB)
Title: Improvements in the preparation of cyanine and styryl dyestuffs
IPC: C09B23/16
Filed: 1952-10-23
Abstract: Anhydro - 2 - methyl - 3 - o  - sulpho - n - butyl-benzthiazolium hydroxide is prepared by heating together 2-methylbenzthiazole and butane-sultone.  Anhydro - 2 - methylmercapto - 3 - o -sulpho - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 1 - o  - sulpho - n - butylquinolinium hydroxide, anhydro - 2 - methyl - 3-o  - sulpho - n - butylbenzselenazolium hydroxide, anhydro - 2 - methyl - 3 - o  - sulpho - n - butyl - 5-methoxybenzselenazolium hydroxide, anhydro-2 : 5 : 6 - trimethyl - 3 - o  - sulpho - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 3-g  - sulpho: g  - methyl - n - butylbenzthiazolium hydroxide, anhydro - 2 - methyl - 3 - o  - sulpho-n - butyl - 5 - chlorobenzthiazolium hydroxide, and anhydro - 2 - methyl - 3 - o  - sulpho - n - propyl - 5 - chlorobenzthiazolium hydroxide are similarly prepared.  Anhydro - 2 - b  - N - methylanilinovinyl - 3-o  - sulpho - n - butylbenzthiazolium hydroxide is prepared by adding methyldiphenylformamidine to a suspension of anhydro-2-methyl-3-o -sulpho-n-butylbenzthiazolium hydroxide in methanol and ethanol, and heating.  Specification 654,690, [Group IV (c)], is referred to.ALSO:Cyanine and styryl dyes in which at least one heterocyclic nitrogen atom carries a sulpho-alkyl group as the sole substituent are prepared by reacting an alkane sultone containing at least three carbon atoms with a heterocyclic base having in the a- or g -position to the nitrogen atom of the heterocyclic ring or alkyl, thioalkyl, b -alkyl thiovinyl, b -halogenovinyl, b -(N-methylanilino)-vinyl, or b -acylanilidovinyl substituent, including similar substituents in which the vinyl groups are substituted by alkyl, aralkyl or aryl groups, and treating the reaction product by a method known to be capable of converting the heterocyclic nitrogen base into a cyanine or styryl dye. Mono-, tri-, and penta-methine and rhodacyanine dyes and styryl dyes are referred to. Anhydro-11-ethyl-3-o -Sulpho-n-butylthia-21 cyanine hydroxide is prepared either by heating together 1-ethyl-2-methylmercaptoquinolinium methosulphate, anhydro-2-methyl-3-o -sulpho - n - butylbenzthiozolium hydroxide, absolute ethanol, and triethylamine, or by heating together 1-ethylquinaldinium, p-toluene sulphonate, anhydro-2-methylmercapto - 3 - o -sulpho-n-butylbenzthiazolium hydroxide, absolute ethanol, and triethylamine. Anhydro-11-ethyl-61-methyl-3-o -sulpho-n-butylthia - 21 - cyanine hydroxide, anhydro-31-methyl-1-o -sulpho-n-butylquina-2-thiocyanine hydroxide, anhydro-3-ethyl-31-o -sulpho-n-butylthiacarbocyanine hydroxide, anhydro-3-ethyl - 31 - o -sulpho-n-butylthiaselenacarbocyanine hydroxide, anhydro-31-ethyl-41-(N : N1 dimethylbenzimidazolylidenei-51keto-41 : 51 - dihydro-3-o -sulpho-n-butylthiazolothia - cyanine hydroxide, anhydro-31 : 9-diethyl-51 : 61-dimethyl-3-o -sulpho-n-butyl - thiacarbocyanine hydroxide, anhydro-31 : 9-diethyl-51 : 61-dimethyl-3-o -sulpho-n-butyl - thiacar - oxythiaselenacarbocyanine hydroxide, anhydro-2-p-dimethylaminostyryl-3- o  -sulpho-n-butyl - 5 : 6 - dimethylbenzthiazolium hydroxide, anhydro-11-ethyl-3-g -sulpho:g -methyl-n-butyl thia-21-cyanine hydroxide, anhydro-3-ethyl-31-g -sulpho : g  - methyl - n - propyl - 9 - ethylselenethia - carbocyanine hydroxide, anhydro-3 : 31-di-o -sulpho - n - butyl- 5 : 51-diphenyl-9-ethyloxacarbocyanine hydroxide, anhydro-3-ethyl-5:51-dichloro - 31 - o -sulpho-n-butyl-9-ethylthiacarbocyanine hydroxide, and anhydro-3:31-di-o -sulpho-n-propyl-5 : 51 - dichloro - 9 - ethylthiacarbocyanine hydroxide are similarly prepared. Specification 654,690 is referred to.