Verfahren zur Herstellung von Phthalocyaninfarbstoffen

The invention comprises dyes of the formula wherein A is a tetrazaporphin dye radical, X is -CH2-, -SO2- or -CO-, R is hydrogen or an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, Ar is a mononuclear radical of the benzene or naphthalene series, Y is an optionally N-substituted sulphonamide group or, when X is -SO2-, Y may also be an alkylsulphonylamino or a substituted or unsubstituted phenyl-sulphonylamino group and n is an integer from 1 to 8, the dyes being free from methylolamino groups. When Y is a sulphonamide group the N-substituents may be alkyl which may be substituted, for example by hydroxyl or sulphate ester, and in which the carbon chain may be interrupted by nitrogen, allyl, aralkyl, cycloalkyl or substituted or unsubstituted aryl, or the nitrogen may form a part of a hetercyclic ring. The dyes are made by reacting tetrazaporphin sulphonyl chlorides, carboxylic acid chlorides or chlormethyl compounds with (a) aminoaryl sulphonamides, (b) primary or secondary aromatic amines, sulphochlorinating the products and reacting them with primary or secondary amines, or (c) arylsulphonic acids containing a primary or secondary amino group, converting the products to sulphochlorides and condensing with primary or secondary amines, or by reacting tetrazaporphin sulphochlorides with primary or secondary arylamines substituted by alkylsulphonylamino or optionally substituted phenylsulphonylamino groups. Examples are given. The dyes dye or print cotton, regenerated cellulose materials, wool, silk and synthetic polyamide or polyurethane fibres. Those dyes containing groups reactive with textile materials containing hydroxyl groups dye and print cotton and regenerated cellulose in conjunction with an alkali treatment.