Patent GB-805217-A (GB)
Title: Improvements in or relating to chromium and cobalt complex compounds of monoazo dyestuffs of the benzene-azo-naphthalene series
IPC: C09B45/14
Filed: 1957-02-22
Abstract: The invention comprises the chromium and cobalt complex compounds of monoazo dyes which in their metal-free state are of formula: <FORM:0805217/IV (c)/1> wherein X is a hydroxy or methoxy group and R is a phenyl radical or an amino group in which one or two hydrogen atoms may be substituted by alkyl, cycloalkyl, aralkyl or aryl radicals, which may also carry further substituents, and two alkyl groups may be cyclically combined by a simple carbon linkage or through an oxygen atom and wherein the nucleus A and the naphthalene nucleus may be further substituted.  The metallized monoazo dyes are prepared by coupling 1 mol. of the diazo compound of a suitably substituted 1-amino-2-hydroxy- or -methoxy-benzene, preferably in an alkaline medium, with 1 mol. of 2-naphthol-3-carboxylic acid which may be substituted and treating the monazo compound with a chromium- or cobalt-yielding agent.  The metallization may be carried out in aqueous or organic, e.g. formamide, medium, or in a concentrated aqueous solution of an alkali metal salt of an aliphatic monocarboxylic acid having less than 4 carbon atoms. Specified chromium compounds are chromic fluoride or sulphate or formate or acetate, chromic potassium or ammonium sulphate and sodium or potassium chromate or bichromate.  When using chromates a strongly caustic alkaline medium which also contains reducing substances is preferred.  Specified cobalt compounds are cobaltous formate or acetate or sulphate and cobalt hydroxide or carbonate.  A substance which forms soluble metal complexes, e.g. tartaric, citric or lactic acids, may be used when working in an aqueous alkaline medium.  The metallized dyes are soluble in organic solvents, e.g. acetone, dimethylformamide, and tetrahydrofuran, and may be used for dyeing synthetic fibres spun from solvent solution and pigmenting plastics and lacquers, yielding bordeaux-red and violet to blue shades.  In examples, monoazo dyes are prepared from the following components and chromium or cobalt complexes thereof prepared; diazo components: 2-aminophenol-4-sulphonic acid-methylamide or -amylamide or -dimethylamide or -diethylamide or -(31-methoxy)-propylamide or -(21-hydroxy)-propylamide or -(21-hydroxy-ethyl)-amide or -di-(21-hydroxyethyl)-amide, or -cyclohexylamide or -benzylamide or -morpholide or -piperidide or -(11 or 21)-naphthylamide or -phenylamide or -(21- or 41-methyl)-phenylamide or -(21-methoxy)-phenylamide or -(21 : 51-dichloro) - phenylamide or - (41 - chloro - 2 : 51-dimethoxy) - phenylamide, 2 - amino - 6 - nitrophenyl - 4 - sulphonamide, 2 - amino - 1 - methoxybenzene - 4 - sulphonamide, 2 - aminophenol - 5 - sulphonic acid - phenylamide, 2 - amino - 4 - chlorophenol - 5 - sulphonic acid - phenylamide, 2 - amino - 1 - hydroxy - 4 - methoxy - benzene - 5 - sulphonic acid - (21-chloro) - phenylamide, 2 - amino - 1 - hydroxy-4 - methylbenzene - 5 - sulphonic acid - (41 - methoxy) - phenylamide, 2 - amino - 1 - hydroxy - 4 - chlorobenzene - 5 - sulphonic acid-N - ethyl - N - phenylamide and 2 - amino - 1 - hydroxy - 6 - acetylamino - 4 - phenylsulphonylbenzene; coupling components: 2-hydroxy-3-naphthoic acid, 2-hydroxy-6-chloro- or -bromo- or -methyl-3-naphthoic acid and 2-hydroxy-7-methoxy-3-naphthoic acid.