Aromatic primary amines having sulfonyl-β-chloroethylamide group, N1-β-chloroethylsulfanilamide (1), 4-methyl-3-aminobenzenesulfonyl-β-chloroethyl-amide (2), 6-methyl-3-aminobenzenesulfonyl-β-chloroethylamide (3), 4-methoxy-3-aminobenzenesulfonyl-β-chloroethylamide (4), 6-ethoxy-3-aminobenzenesul-fonyl-β-chloroethylamide (5), and 4-amino-l-naphthalenesulfonyl-β-chloroethyl-amide (6) were synthesized, and a series of azo dyes were synthesized by use of each of these as a diazo component and acetyl-Hacid, acetyl-J acid, acetyl-γ acid, phenyl-J acid, phenyl-γ- acid, carbonyl-J acid, and di-J acid, as an azo component. Respectively, the dyes thus obtained were used for dyeing of cotton fibers by heating in the presence of alkali and the dyed colors, dyeing proper-ties, and f astnesses have been investigated. Each of these dyes combine with cotton fibers, and dyed cotton were fast to the extraction by pyridine and boiling tese with aqueous solution of citric acid or sodium carbonate. Dyed colors were in the range of orange-red-brown purple. Dyeing properties and fastness against washing depend much on its solubility, and easily soluble dyes showed better dyeing properties and fastness. Condensation of 3-hydroxy 2-naphthoic acid and (1), (4), and (5), respectively, in the presence of phosphorus trichloride gave Naphthol AS having active group After fixing of A on cotton by heating in the presence of alkali, and developing by treating with commercial salts we obtained dyed cotton lacking in clearness, and the wet-fastness was unsatisfactory due to the presence of residual uncombined dye. The results of naphthol dyeing of cotton by use of usual Naphthol AS as the grounder and (1), (4), and (5) as the developer were nearly the same as thore obtaned by the abovementioned way.
