Dyestuffs containing polyalkyleneamine groups

摘要

N - decyl - N1,N1 - diethyl - 1,3 - propanediamine is prepared by reacting 1-bromodecane with an excess of N,N-diethyl-1,3-propanediamine. N - (2 - cyanoethyl) - N - decyl - N1,N1 - diethyl - 1,3 - propanediamine is prepared by refluxing N - decyl - N1,N1 - diethyl - 1,3 - propanediamine with acrylonitrile. N - (3 - aminopropyl) - N - decyl - N1,N1-diethyl -1,3-propanediamine is prepared by reducing N - (2 - cyanoethyl) - N - decyl - N1,N1-diethyl -1,3-propanediamine with lithium aluminium hydride. N1 - (3 - diethylaminopropyl) - N1 - decylsulphanilamide is prepared by condensing N-decyl - N1,N1 - diethyl - 1,3 - propanediamine with p-acetylaminobenzenesulphonyl chloride and hydrolysing the acetylamino group in the product with aqueous hydrochloric acid.ALSO:The invention comprises dyes which are insoluble in water at a pH above 7 and soluble at a pH below 7 of formula wherein M is an organic dyestuff residue, R1 and R11 are C1-C18 alkyl radicals, m is 2 or 3 and p and n are integers less than 6. The dyes are prepared by (a) diazotizing an amine containing a group of formula and coupling with a coupling component or by condensing the said amine with an organic dye containing a carboxylic or sulphonic acid or acid halide group or a group wherein X is a halogen atom. The dyes are used in photographic reproduction processes (cf. Specification 990,972). In examples: (1) N1 - (4 - decyl - 8 - ethyl -4,8 - diazadecyl)-sulphanilamid is diazotized and coupled with 4,41 - bis - o - acetoacetotoluidide to form a disazo dye; (2) equimolar amounts of 1-aminoanthraquinone and isophthaloyl chloride are condensed to give the mono-acid chloride which is further condensed with N-(3-aminopropyl)-N - decyl - N1,N1 - diethyl - 1,3 - propanediamine; (3) Alizarin Rubinol (C.I. 68215) is treated with phosphorus pentachloride to give the corresponding sulphonyl chloride which is condensed with N - (3 - aminopropyl) - N - decyl - N1,N1 - diethyl - 1,3 - propanediamine to give 11 - methyl - 4 - [2 - (4 - decyl - 8 - ethyl - 4,8 - diazadecylsulphamyl) - 4 - toluidinyl] - anthrapyridone; (4) quinacridone is treated with chlorosulphonic acid to give a bis-sulphonyl chloride derivative which is condensed with 2 mols. of N-(3-aminopropyl)-N-decyl-N1,N1-di -ethyl-1,3-propanediamine; (5) copper phthalocyanine is chloromethylated as described in Specification 586,340 or chlorosulphonated as described in Specification 515,637 and the product condensed with N-(3-aminopropyl)-N-decyl - N1,N1 - diethyl - 1,3 - propanediamine.