GB757361A - New monoazo dyestuffs of the benzene-azo-benzene series - Google Patents

Abstract

N - n - Hexyl - N - b - hydroxyethyl - m - trifluoromethylaniline sulphonic acid ester is made by sulphating the corresponding b -hydroxyethyl compound, e.g. with chloro-sulphonic acid in ethylene dichloride, the b -hydroxyethyl compound being made either by reacting N-b -hydroxyethyl - m - trifluoromethylaniline with n-hexyl bromide or by treating N-n-hexyl-m-trifluoromethylaniline with ethylene chlorhydrin in the presence of acid binding agents. N - b - Hydroxyethyl- and -n - hexyl - m - tri - fluoromethylaniline are made by treating m-aminobenzotrifluoride with ethylene chlorhydrin and n-hexyl bromide respectively. 3 - Chloro - 4 - aminobenzonitrile and 2 - amino - 5-cyanobenzotrifluoride are obtained by reducing the corresponding nitro compounds. The products are dyestuff intermediates (see Group IV (c)). Specification 756,079 is referred to.ALSO:The invention comprises dyestuffs which in the form of their free acids are of formula:- <FORM:0757361/IV(c)/1> where X is halogen or a trifluoromethyl group, #U is H or halogen, z is H or halogen or a methyl or trifluoromethyl group, R1 is - CH2CH2CSO3H or - CH2CH2CH2OSO3H and R2 is an alkyl group of 1-6 C atoms or a b - phenyl - or - phenyloxy - ethyl group whose phenyl nuclei may be substituted except with sulphonic or carboxylic acid groups. They may be made either by sulphating, e.g. with sulphuric acid, or with chlorosulphonic acid in ethylene dichlorides, the corresponding dyestuffs in which R1 is - CH2CH2OH or - CH2CH2CH2OH or by diazotizing the appropriate p - aminobenzonitrile and coupling with the desired end component. Dyestuffs in which R1 is a hydroxy - ethyl or - propyl group are made by diazotizing and coupling the appropriate p - aminobenzonitrile with the necessary end component. The dyestuffs dye cellulose acetate rayon and polyamides, e.g. nylon, in orange to red shades. In examples the amines used for diazotization are 2 - chloro - and 3, 5 - dichloro - 4 - aminobenzonitrile and 2 - amino - 5 - cyano - benzotrifluoride, and the coupling components are N - n - hexyl - N - b - hydroxyethyl aniline and m - trifluoro - methyl - aniline sulphonic acid esters, N - b - hydroxyethyl - N - b 1 - phenylethyl - m - toluidine, - b 1 - phenoxyethyl - m - chloroaniline and - b 1 - (p - chlorophenoxyethyl) - aniline - sulphuric acid esters and N - ethyl - N - g - hydroxypropyl aniline the use of the last component necessitating sulphation. Specification 756,079 is referred to.