GB475423A - Manufacture of new monoazo dyestuffs - Google Patents

Abstract

Monoazo dyes are made by diazotizing an amine of the general formula <FORM:0475423/IV/1> where R = an alkyl group having 10--20 carbon atoms, R1 = acidyl (e.g. acetyl, benzoyl or arylsulphonyl) and R2 = phenylene or a homologue or substitution product thereof, and coupling with a naphthol sulphonic acid, an aminonaphthol sulphonic acid or an N-substituted derivative thereof or an arylpyrazolone sulphonic or carboxylic acid. They dye wool in various shades fast to milling and washing. In examples dyes from the following components are described: diazo components: 1-N-dodecyl-N - acetyl-, benzoyl - or p - toluenesulphonyl - amino - 4 - aminobenzene, 1 - N - dodecyl - N - acetylamino - 4 - amino - 2 - methylbenzene, 1 - N - cetyl - N - acetylamino - 4 - aminobenzene; coupling components; N-acetyl H, J or K acid, 1-naphthol-3 : 6-disulphonic acid, 1 - (4<1> - sulphophenyl) - 3 - methyl - 5 - pyrazolone, 1 - (2<1> : 5<1> - dichloro - 4<1> - sulphophenyl - 3 - methyl - 5 - pyrazolone, 2 : 8 : 6 - acid (alkaline coupled), 1 - (4<1> - sulphophenyl) - 5 - pyrazolone - 3 - carboxylic acid, N - b - hydroxyethyl - 2 : 8 : 6 - acid. Specifications 424,354, p 438,129, and 450,564 are referred to. The diazo components may be made by acidylation of the appropriate secondary amine, nitration and reduction. Thus 1-N-dodecyl-N - acetylamino - 4 - aminobenzene is made by acetylating N-dodecylaniline, nitrating in glacial acetic and strong sulphuric acids and reducing. 1 - N - dodecyl - N - benzoylamino - 4 - aminobenzene is made by deacetylating 4 - nitro - 1 - N - dodecyl - N - acetylaminobenzene (see above), treating with benzoyl chloride in toluene and reducing. The secondary amines may be made by condensing an aromatic amine with a long-chain alcohol in presence of the amine hydrochloride.