Patent GB-778262-A (GB)
Title: Improvements relating to monoazo dyestuffs containing heavy metal and their use
IPC: C09B45/14
Filed: 1955-04-20
Abstract: 2 - Aminobenzene - 1 - sulphonic acid glyceride (21 - carboxy - and 51 - chloro - 21 - carboxy - phenylamides) and (51 - methyl - 31 - sulpho - 21 - hydroxyphenylamide) and 4 - chloro - 2 - aminobenzene - 1 - sulphonic acid-(21-carboxyphenylamide) are made by the B<\>echamp reduction of the corresponding nitro-compounds which are obtained by condensing appropriate 2-nitrobenzene sulphonyl chlorides with 2-amino-benzoic acids or 2-amino-4-methyl - phenol - 6 - sulphonic acid.  The products are diazo components in the preparation of dyestuffs (vide Group IV (c)].ALSO:The invention comprises heavy metal complexes of dyestuffs of formula <FORM:0778262/IV(b)/1> where A is a benzene residue containing the SO2NHD group in o-position to N2, B is the residue of an azo component containing OH o to N2 and D is an alkyl or aryl radicle containing a group taking part in the metal complex formation. They are made by coupling an appropriate diazotized o-sulphonamidoaniline in an alkaline medium, optionally in the presence of tertiary nitrogen bases, with the desired azo component and metallizing the product.  When D is an alkyl group it is advantageous if the carbon atom attached to N is also attached to COOH as e.g. in aminoacetic acid.  When D is an aryl residue the group forming metal complexes may be COOH or phenolic OH and it should be in the o-position to the NH group as in e.g. anthranilic acid, 2 - naphthylamine-3-carboxylic acids and o-amino - phenols. The benzene rings of the o - aminobenzene sulphonic acid radicle and of the aromatic residue of the sulphonamide group may be substituted by e.g. halogen, alkyl, alkoxy, acylamino, sulphonic acid and substituted sulphonyl groups such as sulphonamide and alkyl and aralkyl sulphonyl groups.  Azo components indicated and specified are acylacetic acid arylamides, 5 - pyrazolones, 2, 4 - dihydroxyquinolines, 4 - alkylphenols, 2 - naphthols with a free 1 - position and 1 1 naphthols with a free 2 - position and the 4 - position of which is occupied or marked preferred being 1 - phenyl - 3 - methyl - 5 - pyrazolones, naphthols and their sulphonic acids. Metallization is effected in known fashion chromium, cobalt and copper complexes being mentioned for wool dyeing and nickel and iron complexes for incorporation in lacquers.  The dyestuffs dye polypeptide fibres e.g. wool, silk, Lanital and superpoly-amides and - urethanes and leather and may be used to colour lacquers.  Chromium complexes containing a sulphonic acid group dye wool from a strong acid bath.  The complexes which do not contain sulphonic acid groups dye from a neutral to weakly acid bath.  In examples illustrating the preparation of the dyestuffs and their use in dyeing wool in red, green, brown and yellow tints the diazo components are 2 - aminobenzene - 1 - sulphonic acid glycinide, - (21 - carboxy 1 and 51 - chloro - 21 - carboxy - phenylamides and - (21 - hydroxy - and 51 - methyl - 31 - sulpho - 21 - hydroxy - phenylamides, and 4 - chloro -, - methyl - and - methylsulphonyl - 2 - aminobenzene - 1 - sulphonic acid - (21 - carboxy - phenylamides), the azo components are 1 - phenyl - 3 - methyl - 5 - pyrazolone and its 31 - sulpho - sulphonamido -, - chloro- and 21, 51 - dichloro - 41 - sulpho - derivatives, 1, - (41 - sulphophenyl) - 3 - carboxy - 5 - pyrazolone, 4 - acetyl - and - methyl - 1 - naphthol - 8 -, 1 - naphthol - 4 - and - 5 - mono - and 2 - naphthol - 6 - mono - and - 3, 6 - and 6, 8 - di-sulphonic acids and 2 - naphthol and its 6 - sulphonic acid methylamide the metals chosen being chromium, cobalt and copper.