Patent GB-951471-A (GB)
Title: New metal complex azo compounds
Inventor: ANDREW HERBERT FRANCIS
IPC: C09B62/012
Filed: 1961-05-26
Abstract: The invention comprises metal complexes of the compounds of the formula <FORM:0951471/C3/1> wherein A stands for an aromatic radical, M stands for a divalent radical of the naphthalene series containing a metallizable group in ortho position to the azo group marked (2); m stands for 0 or 1, E is the radical of a coupling component which, when m stands for 0, contains a hydroxyl group in ortho position to the azo group marked (2), n stands for 1 or 2, R stands for a hydrogen atom or an alkyl group having up to 6 carbon atoms and Z stands for an acyl radical which contains a reactive group, as defined below, or for a heterocyclic radical which contains 2 or 3 nitrogen atoms in the heterocyclic nucleus and which carries on at least one carbon atom in ortho position to a nitrogen atom of the nucleus, a halogen atom or a labile group.  By the term "reactive group" is meant a group by means of which the dye can react with the fibre to form a covalent bond.  By the term "labile atom or group" is meant an atom or group which is replaced by hydroxyl on subjecting the dyestuff to a treatment with boiling, dilute aqueous alkali.  Of particular interest are the complexes of the general formula <FORM:0951471/C3/2> where Z1 stands for a halogeno-s-triazine radical, A1 stands for a sulphophenyl radical, B stands for a 1 : 2-naphthylene radical and p stands for 1 or 2; of the general formula <FORM:0951471/C3/3> wherein A2 represents a benzene or naphthalene radical having 1-3 sulphonic acid groups, Q stands for a hydrogen atom or sulphonic acid group, V stands for a methyl or carboxylic group, P1 stands for a benzene nucleus and Z1 for a halogeno-s-triazine radical; and of the formula <FORM:0951471/C3/4> wherein B1 stands for a 1 : 2-naphthylene radical, A1 stands for a sulphophenyl radical, V stands for a methyl or carboxylic acid group, P1 stands for a benzene nucleus and Z1 for a halogeno-s-triazine radical.  Acyl radicals specified include the radicals of a :b -unsaturated aliphatic carboxylic acids, e.g. acrylic, a -chloroacrylic, propiolic, maleic and mono- and dichloromaleic acids especially radicals of such halogenated aliphatic acids as chloracetic acid, b -chloro-, b -bromo- and a ,b -dichloropropionic acids.  Substituents which may be present s-triazinyl or pyrimidyl radicals in the dyes include bromine or chlorine atoms, sulphonic acid, thiocyano, sulphophenoxy, sulphophenylthio, nitrosulphophenoxy, disulphophenoxy, sulphonaphthoxy groups, groups of the formula <FORM:0951471/C3/5> where Y represents the atoms necessary to form a 5- or 6-membered heterocyclic ring, quaternary ammonium or pyridinium groups, groups of the formula <FORM:0951471/C3/6> where R3 and R4 may be the same or different and each represents a hydrogen atom or alkyl, aryl or aralkyl group, cyano, amino- and substituted amino, e.g. di-(b -hydroxyethyl) amino, disulphophenylamino, alkoxy, aryloxy and phenyl thio groups.  The dyes are obtained by reacting appropriate metallized dyes containing an amino group with an appropriate acid halide or anhydride or heterocyclic compounds containing two or more halogen atoms in ortho positions to the nitrogen atoms or by reacting an appropriate dye containing a heterocyclic ring containing two chlorine or bromine atoms in such a manner as to replace one or both halogen atoms with other labile groups.  The dyes are used for colouring wool, silk and polyamide fibres, cotton and other natural or regenerated cellulose materials and are preferably applied in conjunction with an acid binding agent. The dyes employed as starting materials are prepared by conventional diazotisation and coupling procedures.  Examples are furnished. Specification 388,322 is referred to.