Patent GB-957445-A (GB)
Title: New azo dyestuffs containing substituted piperazine groups
Inventor: MCKAY WILLIAM BYRES
IPC: C09B62/006
Filed: 1961-04-10
Abstract: The invention comprises azo dyes which are represented by the formula <FORM:0957445/C3/1> wherein A represents a mono- or bicyclic aryl radical which may contain substituents, E represents a substituted or unsubstituted naphthylene radical and Y represents an acyl radical which contains a reactive group or Y represents 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 said nucleus a reactive halogen atom or a reactive group. The terms " reactive or labile halogen atom " and " reactive or labile group " denote halogen atoms or groups respectively which are capable of reacting with hydroxy groups present in cellulose textile materials whereby the dyestuffs containing such atoms or groups become attached to the cellulose textile material through formation of covaltent bond. The dyes may be made by condensing a compound of the formula Y-halogen with an azo dye as defined above where Y is H or by conventional processes of diazotization and coupling.  Examples of acyl radicals containing a reactive group are radicals of a :b -unsaturated aliphatic carboxylic acids, e.g. acrylic, a -chloroacrylic, propionic, maleic, mono- and di-chloromaleic acids and chloracetic, b -chloro- and b -bromo-propionic and a :b -dichloropropionic acids.  Examples of heterocyclic radicals represented by Y are 1 : 3 : 5-triazine, pyridazine and pyrimidine radicals containing bromine or chlorine atoms, sulphonic acid groups, thiocyano, negatively substituted aryloxy and arylthio groups, e.g. sulphophenoxy, sulphophenylthio, nitrosulphophenoxy, disulphophenoxy and sulphonaphthoxy groups, groups of the formula <FORM:0957445/C3/2> where Z represents the group of atoms necessary to form a 5- or 6-membered heterocyclic ring, optionally substituted or forming part of a fused ring system, or quaternary ammonium or pyridinium groups or groups of the formula <FORM:0957445/C3/3> where R1 and R2 represent alkyl, cycloalkyl, aryl or aralkyl groups or R1 and R2 form with the nitrogen atom a 5- or 6-membered ring or containing groups of the formula <FORM:0957445/C3/4> where R3 and R4 represent H, or alkyl, aryl or aralkyl groups.  Where Y is a 1 : 3 : 5-triazine or pyrimidine ring carrying only 1 reactive halogen the ring may carry additional substituents, e.g. cyano, amino and substituted amino groups, alkyl, aryl, alkoxy, aryloxy groups and the corresponding thio groups. Preferably, Y represents a dichloro, 5-cyanodichloro- or trichloropyrimidyl group or a chloro- or dichlorotriazinyl group. Radical E may be a hydroxy or sulphonaphthylene, hydroxy - sulpho- or -disulphonaphthylene or hydroxy - chloro - sulphonaphthylene radical. Preferred dyes are of the formula <FORM:0957445/C3/5> where n=2 or 3; of the formula <FORM:0957445/C3/6> where P represents the group <FORM:0957445/C3/7> attached to the naphthalene ring in the 2- or 3-position and A1 represents a sulphonated aryl radical; and of the metal complexes of azo dyes of the formula <FORM:0957445/C3/8> where X is a metallizable group attached to A in ortho position to the azo group.  Metals specified include nickel, cobalt, chromium and copper. Metallizable groups specified include hydroxy, carboxy, methoxy and carboxymethoxy. The dyes colour wool, silk and polyamide textile materials and in particular cellulosic materials, e.g. cotton, viscose, rayon and linen preferably the dyeing being carried out in conjunction with a treatment with an acid binding agent. Specification 797,946 is referred to.