GB793532A - New monoazo dyestuffs and process for making them - Google Patents

Abstract

The invention comprises dyestuffs, preferably of the pyrazolone series, which contain a group of formula <FORM:0793532/IV (b)/1> where X is H or a hydrocarbon radicle, B is a b - or a -haloalkyl residue and when X is a hydrocarbon radicle there must be present a group imparting solubility in water, advantageously an SO3H group. Advantageously the halogen atom is in the a -position of the alkyl residue. X may be an aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicle. Further specified substituents for the dyestuffs are COOH, SO3H, SONH2, MeSO2, NO2, halogen, acylamino, alkyl and alkoxy groups. A preferred series of dyestuffs has the formula <FORM:0793532/IV (b)/2> where R and R1 are benzene residues and one X is H and the other an -SO2-NHCOCH2Cl group. The dyestuffs may be made by acylating a sulphonamide group of an appropriate dyestuff using as acylating agent a halide or anhydride of an aliphatic halogen-carboxylic acid such as a - and b -chloro-propionic acid chloride, bromacetyl bromide and chloracetyl chloride and the corresponding anhydrides. The acylation is effected in conventional fashion in the presence of diluents and acid-binding agents and preferably with an excess of acylating agent. The starting dyestuffs may be made by conventional methods. Specified diazo components are aniline-2-, -3- and -4-sulphonamides and sulphon-methyl-, -ethyl-, -butyl-, -hexyl- and -phenyl-amides, 4-methyl-aniline-2- and -3- sulphonamides, 2-methoxy-aniline-3-, -4- and -5-sulphonamides, 2 - naphthylamine - 6 - sulphonamide, aniline, o-, m- and p-chloranilines, 2,5-dichloroaniline, nitranilines, toluidines, aniline-3-and -4-methyl sulphones and sulphonic acids and 1 - amino - 2 - naphthol - 4 - sulphonic acid. Specified coupling components are 2-amino- and -hydroxy - naphthalene - 6 - sulphonamide, 1 - (a - naphthyl) - 3 - methyl - 5 - pyrazolone, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21-, -31-and -41-sulphonamide and sulphonmethylamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - chloro - 51 - sulphonamide, 1 - phenyl -, -(21-, 31- and 41-chloro- and 41-nitro-phenyl)-3-methyl - 5 - pyrazolones, 1 - phenyl - 3 - methyl - 5-pyrazolone-31- and -41-sulphonic acids and 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid. The dyestuffs dye leather, silk, wool and super-poly-amides and -urethanes from weakly acid to weakly alkaline baths. Examples are provided illustrating the preparation of dyestuffs from certain of the above specified components and their use in dyeing wool in orange or yellow shades.