GB399583A - The manufacture of dyestuffs containing sulphur - Google Patents

Abstract

Dyes of the thiazine-quinone type are prepared by condensing an arylenethiazthionium chloride with an aromatic compound containing in the molecule in addition to the primary or secondary amino group at least one -SO2NH-group, either the sulphur or the nitrogen atom of this group being attached to the aryl radicle, subjecting this product to alkali reduction and condensing the resulting o-aminomercaptan with an arylquinone (cf. Specification 265,641, [Class 2 (iii), Dyes &c.]). The introduction of the -SO2NH- group into the arylamino substituent attached to the thiazine nucleus results in an easy solubility in the sodium sulphide bath and in dyes of fast bright shades. In an example the condensation product of 3-methyl-5-chloro-1.2-phenylenethiazthionium with p-aminodiphenyl-p<1>-sulphanilide according to the process of Specification 265,498, [Class 2 (iii), Dyes &c.], the product saponified and converted to the zinc mercaptide and condensed with chloranil to give a bright greenish-blue vat dye. A table gives the properties of the corresponding dyes derived by replacing p-aminodiphenyl-p<1>-sulphanilide by the following amines :--4 - aminophenylsulphanilide, N - (b -naphthyl)-3-aminophenylsulphonamide, N-(4<1>-aminophenyl) - benzenesulphonamide, N - (4<1>-aminodiphenyl)-benzene- and 4-chlorbenzenesulphonamides, N - 2 - (4<1>-aminodiphenyl)-benzenesulphonamide, p - aminodiphenyl - p<1> - (3<11>-chloro- and 2<11>-methoxy-sulphanilides), 4-aminodiphenylether - 2 - sulphanilide, 2 - aminonaphthalene-7-sulphanilide (all dyeing blue shades). Sulphanilido derivatives specified above are prepared as follows:--p<1>-nitrobenzenesulphochloride is condensed with aniline and the corresponding m-derivative with b -naphthylamine followed by reduction to give 4-aminophenylsulphanilide and N-(b -naphthyl)-3-aminophenylsulphonamide respectively; p-nitrodiphenyl-p<1>-sulphochloride is condensed with aniline, m-chloraniline, and o-anisidine followed by reduction to give the sulphanilide, 3<11>-chlorsulphanilide and 2<11>-methoxysulphanilides of 4<1>-aminodiphenyl; benzenesulphochloride is condensed with p-nitraniline followed by reduction to give N-(4<1>-aminodiphenyl)-benzenesulphonamide, and with 4-acetylamino-2<1>-aminodiphenyl followed by saponification to give N-2-(4<1>-aminodiphenyl)-benzenesulphonamide, 4-nitrodiphenylether-2-sulphochloride is condensed with aniline and reduced to give 4-aminodiphenylether-2-sulphanilide, and 2-acetylaminonaphthalene-7-sulphochloride with aniline followed by saponification to give 2-aminonaphthalene - 7 - sulphanilide. Azobenzene is condensed with benzene- and p-chlorbenzene-sulphinic acids, the products reduced to hydrazo derivatives and converted to N-p<1>-aminodiphenyl-benzene and 4-chlorbenzene sulphonamides respectively in known manner.