Patent GB-529454-A (GB)
Title: Manufacture and use of azo dyes
IPC: C09B31/04
Filed: 1939-05-24
Abstract: 529,454. Dyes ; dyeing cellulose derivatives ELLIS, G. H., OLPIN, H. C., and WRIGHT. J. May 24, 1939, No. 15410. [Classes 2 (ii): 2 (iii) and 15 (ii)] Azo dyes suitable for the coloration of materials made of or containing cellulose esters or ethers are obtained by coupling with an aromatic amine capable of coupling in p-position to a substituted amino group, a diazotized aminoazo compound (including a tetrazotized diaminoazo compound obtainable by reduction of a nitro group in the diazo component), such compound containing a benzene nucleus carrying a primary amino group, an azo group in p-position thereto and an acidylamino group. Specified aminoazo compounds are aryl-azoamilines carrying an acidylamino group in the aniline nucleus and obtainable by coupling a diazotized arylamine, e.g. aniline, toluidines, anisidines, phenetidines, 1-naphthylamine and their halogen and/or nitro derivatives, with an acidylaminoaniline coupling in p-position to the free amino group, e.g. monoacetyl or monobenzoyl-1:3-phenylenediamine, 2- or 3-amino-4- acetylaminotoluene, 2-amino-4-acetylaminoanisole or -phenetole, 2-amino-4-acetylamino-1- #-hydroxyethoxybenzene or 3-acetylmethylaminoaniline. Specified final coupling components are N-ethyl-#-hydroxyethyl-aniline, N-di- (#-hydroxyethyl)-aniline, N-ethyl-#-hydroxyethyl-m-toluidine, N-di-(#-hydroxyethyl)-mtoluidine, N-dimethyl- or diethyl-m-toluidine N-alkyl (including hydroxyalkyl) derivatives'of 1-naphthylamine and its nuclear substitution products capable of coupling in the 4-position, and the 3-methyl-6-methoxy-, 3:6-dimethoxy- and 3:6-dimethyl-derivatives of N-diethylaniline The dyes may be produced on textile materials made of or containing a cellulose ester or ether by incorporating the aminoazo component in the material, diazotizing and coupling. Alternatively, filaments, straws, films and the like may be formed from solution of the cellulose esters or ethers in which the dyes are incorporated. Examples relate to the production of the dyestuff, 4-nitroaniline# 2-amino-4-acetylaminoanisole # N-di-(#-hydroxyetlyl)-m-toluidine or N-dimethyl-m-toluidine, (1) on a cellulose acetate fabric by impregnating with an aqueous soap and turkey red oil dispersion of the aminoazo component, diazotizing on the material and developing with an aqueous turkey red oil dispersion of the coupling component; the dyeing is readily dischargeable with zinc formaldehydesulphoxylate; (2) on a mixed cellulose acetate-viscose fabric, with simultaneous dyeing of the viscose fibres, by treatment in a bath containing the aminoazo component and Diazo brilliant scarlet BAL, diazotizing on the material and developing with an aqueous turkey red oil dispersion of the coupling component ; (3) in substance by diazotizing the aminoazo component with nitrosylsulphuric acid, adding sulphamic acid and coupling in sodium acetate solution the product may be incorporated in a cellulose acetate spinning solution. 3-Methyl-6-methoxy-, 3:6-dimethoxy- and 3:6 - dimethyl N - - diethylanilines are obtained by ethylation of 3-methyl-6-methoxyaniline, 3:6-dimethoxyaniline and p-xylidine respectively. 2- Amino-4-acetylaminophenetole is obtained by reducing the nitro group in the product of nitration of 4-acetylaminophenetole. 2 Amino - 4 - acetylamino - # - hydroxyethoxybenzene is obtained by reducing the nitro group in the product of reaction of #- chloroethyl alcohol with 2-nitro-4-acetylaminophenol. 1 - Amino 3 - acetylmethylaminobenzene is obtained by reducing the nitro group in N - acetyl - N - methyl - 3 - nitroaniline. Specifications 506,740 and 523,287 are referred to.