Patent GB-642171-A (GB)
Title: Manufacture of metallisable monoazo dyestuffs and dyeings therewith
IPC: C09B45/16
Filed: 1947-12-19
Abstract: Amines of the general formula <FORM:0642171/IV (b)/1> wherein Y represents a sulphonic acid group, an arylsulphonyl radical of the benzene series or a lower alkylsulphonyl radical of at most four carbon atoms, and wherein the nucleus A may carry further simple substituents) are manufactured by condensing 4-chloro-3-nitrobenzenesulphochloride with an aminosalicylic acid (e.g. 3- or 5-amino-2-hydroxybenzoic acid or mixtures thereof, 5-amino-3-methyl-, 5-methyl- or 5-chloro-3-amino-, 5-amino-3-sulpho- or 5-sulpho-3-amino-2-hydroxybenzoic acid) in an aqueous medium at 60-70 DEG  C. in the presence of an acid-binding agent, heating an aqueous solution of the product with sodium sulphite to replace the chlorine atom by a sulphonic acid group, or with an alkyl or aryl sulphinate (e.g. sodium methyl-, ethyl-, propyl-, butyl- or benzene-sulphinate or potassium p-toluenesulphinate or p-chlorobenzenesulphinate) to replace the chlorine atom by an alkyl or aryl sulphonyl group, and finally reducing the nitrogroup, e.g. with iron and hydrochloric acid.ALSO:Metallizable monoazo dyestuffs are manufactured by diazotizing an amine of the general formula <FORM:0642171/IV (c)/1> (wherein Y represents a sulphonic acid group, an arylsulphonyl radical of the benzene series or a lower alkylsulphonyl radical of at most four carbon atoms, and wherein the nucleus A may carry further simple substituents) and coupling with an aminonaphtholsulphonic acid of the general formula <FORM:0642171/IV (c)/2> (wherein R represents hydrogen or an alkyl or aryl radical which may contain substituents, and Z represents hydrogen or a sulphonic acid group).  The products are suitable for chrome printing on cotton, and for dyeing animal fibres from an acid bath, preferably with after-chroming, giving bluish-red to reddish-violet tints. Examples illustrate the use of the following components: diazo components: 2-aminobenzene-1-sulphonic acid-4-4-sulphonic acid phenylamide - 41 - hydroxy - 51 - carboxylic acid and its 31-methyl-derivative, and -21-hydroxy-31-carboxylic acid and its 51-methyl and 51-chloro-derivatives, 2-aminobenzene-1-phenylsulphonyl-4-sulphonic acid phenylamide-41-hydroxy-31-carboxylic acid and its 51-sulphonic acid, 2 - aminobenzene - 1 - (41 - tolylsulphonyl)-, -1-(41-tert.-butylphenylsulphonyl-and -1-(41-chlorophenylsulphonyl)-4-sulphonic acid phenylamide - 311 - carboxy - 411 - hydroxy-511-sulphonic acid, 2-aminobenzene-1-n-butylsulphonyl-4-sulphonic acid phenylamide-41-hydroxy-31-carboxylic acid and its 51-sulphonic acid, and 2-aminobenzene-1-ethyl- and-methylsulphonyl - 4 - sulphonic acid phenylamide - 41-hydroxy - 31 - carboxylic acid; coupling components: 2 : 8 : 6-acid and its N-methyl-, -ethyl-, -phenyl-, -o : p-dimethylphenyl-, -o -aminoethyl-, -p-tolyl-, -p-chlorophenyl- and -p-methoxyphenyl-derivatives, and 2 : 8 : 3 : 6-acid and its N-o -aminoethyl- and -b -hydroxyethyl-derivatives. Reference is made to the acetylation, with acetic anhydride, of the dyestuff 2-aminobenzene - 1 - sulphonic acid-4-sulphonic acid phenylamide - 51 - methyl - 21 - hydroxy-31-carboxylic acid --> 2 - o  - aminoethylamino-8-naphthol-6-sulphonic acid.