GB453431A - Improvements in the manufacture and production of condensation products - Google Patents

Abstract

Coloured products are obtained by condensing a butadiene dioxide (1 mol.) with an unsulphonated aromatic or heterocyclic compound (2 mols.) containing reactive hydrogen and, if the resulting product is not coloured, introducing the azo group by coupling in substance or on the fibre with diazo compounds or, if a diazotizable amino group is present, diazotizing and coupling in substance or on the fibre with unsulphonated coupling components. The azo group may also, if desired, be similarly introduced into the coloured condensation products. Specified butadiene dioxides are, besides butadiene dioxide itself (obtainable by splitting off hydrogen chloride from 1 : 4-dichlor-2 : 3-dihydroxybutane), the dioxides similarly obtainable from the corresponding dichlordihydroxy compounds from isoprene, piperylene and 2 : 3-dimethylbutadiene. Specified aromatic or heterocyclic compounds containing reactive hydrogen are aniline, methylaniline, ethylaniline, n - butylaniline, cyclohexylaniline, benzylaniline, diphenylamine, 1-amino-4-acetylaminobenzene, 1-amino-4-nitrobenzene, naphthylamines, phenols, naphthols, aminopyrazolones, aminopyridines, hydroxyquinolines, aminoazo compounds and aminoanthraquinones. The products are suitable for dyeing acetate artificial silk from aqueous suspensions or for colouring cellulose esters or ethers in general or lacquers prepared therefrom; they may also be rolled into solid cellulose esters or ethers, preferably after addition of softening agents. The following examples are specified: (1) the condensation product from butadiene dioxide (1 mol.) and aniline (2 mols.) is dissolved p in dilute hydrochloric acid and coupled with diazotized p-nitraniline; the product dyes acetate artificial silk brilliant yellow; the aniline may be replaced by toluidines, e.g. m-toluidine, xylidines, aminophenols, aminonaphthols or aminopyridines; (2) butadiene dioxide (1 mol.) is condensed with p-aminoazobenzene or 4-amino-3 : 4<1>-dimethylazobenzene (2 mols.); the aqueous suspensions obtained by dissolving the products in acetone and pouring into water dye acetate artificial silk very powerful lemon yellow; (3) butadiene dioxide (1 mol.) is condensed with a -aminoanthraquinone (2 mols.); the product dyes acetate artificial silk orange from a soapy dispersion; (4) the product obtained by condensing butadiene dioxide (1 mol.) with phenol, 8 - hydroxyquinoline or 8 - aminoquinoline (2 mols.) in presence of a little solid potassium hydroxide is coupled with a diazotized aromatic amine; (5) the condensation product from butadiene dioxide (1 mol.) and 1-amino-4-acetylaminobenzene (2 mols.) is saponified and the product is diazotized and coupled with b -naphthol (2 mols.); the product dyes acetate artificial silk copper red.