Patent GB-190515763-A (GB)
Title: Improvements in the Manufacture and Production of Intermediate Compounds and of Colouring Matters containing Sulphur.
Inventor: JOHNSON JAMES YATE
Filed: 1905-08-01
Granted: 1906-04-05
Abstract: 15,763. Johnson, J. Y., [Badische Anilin & Soda Fabrik]. Aug. 1. Dyes, artificial; ; thio derivatives of quinones and hydroquinones. - Thio derivatives of p-quinones, hydroquinones, or their derivatives are produced by acting on the corresponding p-quinones with sulphurizing-agente, with or without the addition of oxidizing-agents. The bodies so produced are condensed with a monoalkylated p-diamine thiosulphonic acid, or an unsymmetrically dialkylated p-diamine thiosulphonic acid, or with a corresponding mercaptan, or disulphide, with or without subsequent oxidation. In a modification, dyes are produced directly by the interaction of a p-quinone, or a derivative thereof, a sulphurizing-agent, and one of the p-diamine derivatives specified above with or without subsequent oxidation. Sulphurizing-agents which can be employed are thiosulphuric acid, monothio acids such as thioacetic acid, trithiocarbonic acid, xanthogenic acid, sulphocyanic acid, alkali sulphides, sulphuretted hydrogen, &c. or any agent containing the group - SH. The quinone compounds mentioned as suitable include quinone and its halogen derivatives, such as mono- or dichlorquinone, or chloranil. The reaction is represented by the general equation- The hydroquinone derivatives so produced can be converted into quinone derivatives by subsequent or simultaneous oxidation, and the resulting quinone derivatives can be again sulphurized. When quinones are treated simultaneously with sulphurizing- and oxidizing-agents, polythio derivatives are produced directly. The thio derivatives can be converted by reduction or saponification into mercaptans, and these are converted readily into mono- or di-sulphides. The use of tritbiocarbonic acid as sulphurizing-agent yields such sulphides directly. In examples are produced mono-, di-, or tetra-tbiosulphonic acids of hydroquinone, quinone, and their 2 : 5- or 2 : 6-dichlor derivatives, benzoylhydroquinone mercaptan, and hydroquinone xanthogenate. The condensation with the above-mentioned alkylated p-diamines takes place in alkaline solution, yielding, after subsequent oxidation if necessary, dyes which dye cotton from sodium sulphide solution blue to blue-green shades. When thio derivatives containing the group - SÀSO3H are employed, and the condensation is carried on at a low temperature, and in dilute alkaline solution, intermediate dyes are obtained containing the group - SÀSO3H and suitable for dyeing wool. Further treatment converts these dyes into the dyes described above. In examples, dyes are produced from dimethyl-pphenylenediamine thiosulphonic acid, and hydroquinone monothiosulphonic acid, 2 : 6-dichlorh3-droquinone mono- or dithiosulphonic acid, and 2 : 6 - dichlorhydroquinonemercaptan. In other examples, dyes are produced directly from chloranil, dimethyl-p-phenylenediamine thiosulphonic acid, and sodium sulphide ; from 2 : 5- or 2 : 6- dichlorquinone, chloranil, or benzoquinone, dimethyl-p-phenylenediamine thiosulphonic acid, and sodium thiosulphate, and from similar mixtures.