Heavy metal complexes of azo dyestuffs containing a 2-amino-3-hydroxypyridine as coupling component

Abstract

The heavy metal complexes of azo dyestuffs of formula ##STR1## where B is hydrogen, chloro or bromo and D is the residue of a diazo component of the benzene or naphthalene series that contains an hydroxyl, carboxyl or amino group in the position ortho to the azo group, are useful to dye substrates, notably wool, in level green and blue shades having good resistance to acid, alkali, light and rubbing.

We claim: 
     
       1. The copper, nickel, chromium or cobalt complex of a compound of formula ##STR39## in which B is chloro, bromo or hydrogen; D is phenyl or naphthyl that contains, in the position ortho to the azo bridge, hydroxyl, amino or carboxyl, and where said phenyl is further unsubstituted or substituted by chloro, bromo, methyl, nitro, cyano, methylsulphonyl, trifluoromethyl, carbomethoxy, carboethoxy, hydroxyethylsulphonyl, chloroethylsulphonyl, sulfonamido, N-methylsulphonamido, N,N-dimethylsulphonamido, N,N-diethylsulphonamido, N,N-di(hydroxyethyl)sulfonamido, N-phenylsulfonamido, methoxy, sulfophenylazo, sulfonaphthylazo phenylazo, acetylamino, acetyl, CONH 2 , tosylamino, or a fibre-reactive acylamino group where fibre-reactive acyl is selected from the group consisting of chloroacetyl, bromoacetyl, β-chloropropionyl, β-bromopropionyl, α,β-dichloropropionyl, α,β-dibromopropionyl, chloromaleyl, acrylyl, β-chloroacrylyl, β-bromoacrylyl, α-chloroacrylyl, α-bromoacrylyl, α,β-dichloroacrylyl, α,β-dibromoacrylyl, trichloroacrylyl, chlorocrotonyl and propiolyl, and where   said naphthyl is further unsubstituted or substituted by sulfo, sulfonamido, nitro, acetylamino or sulfophenylazo.   
     
     
       2. A complex according to claim 1 in which D is phenyl or substituted phenyl. .Iadd. 3. The copper, nickel, chromium or cobalt complex of a compound of the formula ##STR40## in which B is chloro, bromo or hydrogen; and D is phenyl which is substituted in the ortho-position to the azo bridge by hydroxy, methylsulfonylamino, p-tolysulfonylamino, carboxy or sulfo and which is further unsubstituted or substituted by nitro, chloro, sulfonamido, NH 2  --, sulfo, 1,2-dibromopropionylamino, chloroacetylamino, 3'-sulfophenylazo, methyl, 2-(3'-sulfophenyl)-4-chloro-(1,3,5)-triazinylamino, N-phenylsulfonamido, 
     
     
        or methylsulfonyl. .Iaddend. .Iadd. 4.  The 1:1-copper complex according to claim 3, of a compound of the formula ##STR41## 
     
     
        .Iaddend..Iadd. 5.  The 1:1-copper complex according to claim 3, of a compound of the formula ##STR42## 
     
     
        .Iaddend..Iadd. 6.  The 1:1-copper complex according to claim 3, of a compound of the formula ##STR43## .Iaddend.