GB211772A - Manufacture of acylacetyl-compounds - Google Patents

Abstract

Diacylacetyldiamino compounds are prepared by heating together, advantageously in the presence of a solvent or diluent at least two molecular proportions of an acylacetic ester and one of a diamine of the general formula NH2-Y-NH2, where Y is an aryl or diaryl residue or a residue of a diaryl compound of the general formula <FORM:0211772/2/1> wherein A and A1 are the same or different aryl residues or substituted aryl residues united by Z which may be O, S, -CH2-, -CO-, -NH-, -NH.CO-, -N=N-, <FORM:0211772/2/2> or the like. As diluents may be used benzene hydrocarbons, chlorobenzene, nitrobenzene, naphthalene, or a large excess of the acylacetic ester to be used for the reaction; the acylacetic esters specified are acetoacetic ester and its homologues and analogues such as benzoylacetic ester; diamines which may be used are the arylenediamines such as phenylene and naphthalene diamines, diamines of the anthracene series, diaryldiamines such as benzidine, tolidine, dianisidine, dichlorbenzidine, nitrobenzidine, nitrotolidine, thioaniline, diamino-diphenylether, diamino-ditolylmethane, diamino-benzophenone, diamino-di-phenylamine, aminobenzoylphenylenediamine, diamino-azobenzene, diamino-azoxybenzene, diamino-diphenylurea, and aminophenol-ethyleneether. The production of diaceto-acetylbenzidine in the absence of a solvent or diluent is excluded. In examples the production of the following compounds is described, chlorobenzene, nitrobenzene, solvent naphtha, or an excess of acetoacetic ester being employed as diluent:-diacetoacetyl derivatives of p-phenylene diamine, benzidine, o-tolidine, dianisidine, 4 : 41-diaminobenzophenone, and 4 : 41-diamino-azobenzene; also dibenzoylacetyl-o-tolidine. The properties are also tabulated of dibenzoylacetyl-benzidine and the diacetoacetyl compounds of 1 : 4-, 1 : 5-, and 2 : 6-naphthylene diamines, 2 : 21- and 3 : 31-dichlorbenzidine, 4 : 41-diamino-3 : 31-dichlorodiphenylmethane, 4 : 41-diamino-3 : 31-ditolylmethane, 4 : 41-diamino-azoxybenzene, 4 : 41-diamino-3 : 31-azotoluene, 4 : 41-diamino-diphenylurea.ALSO:The diacylacetyl-diamino compounds obtained from diamines and an acylacetic ester such as acetoacetic ester or benzoylacetic ester have a substantive character and when fixed upon the fibre yield fast shades when developed with diazo compounds.