GB900172A - New bis-sulphinic acid compounds - Google Patents

Abstract

The invention comprises bis-sulphinic acids of the general formula HO2S-R-SO2H and salts thereof, wherein R represents a saturated cyclo aliphatic hydrocarbon radical containing five or six carbon atoms, the two sulphinic groups being attached to different carbon atoms, or a saturated aliphatic hydrocarbon radical containing 4-18 carbon atoms, the two sulphinic groups being separated by a straight chain of at least 4 carbon atoms. They may be prepared by reduction of the corresponding sulphonyl chlorides, which may be obtained by chlorination of the corresponding sulphonic acids or alkyl bis-isothiouronium salts. The reduction is preferably effected with sodium sulphite yielding the sodium salts of the sulphinic acids which may be isolated as such or converted into less soluble salts; acidification yields the free acids. Examples describe the preparation of (1) 1:4-butane bis-sulphinic acid using magnesium or sodium sulphite yielding the magnesium or sodium sulphinate which is acidified to liberate the free acid; the zinc sulphinate is prepared from the sodium salt and zinc chloride; in like manner there are prepared (5) 1:5-pentane bis sulphinic acid and its sodium and zinc salts and (6) 1:10-decane bis-sulphinic acid, (7) 2-methyl butane-1:4-di-sulphinic acid, (8) 2:5-hexane bis-sulphinic acid, (10) 1:4-cyclohexane bis-sulphinic acid, (11) 1:12-dodecane bis-sulphinic acid and (12) 1:18-octadecane bis-sulphinic acid and their sodium salts. Numerous other values for R are exemplified. The compounds react with formaldehyde to yield the corresponding hydroxy methyl sulphones; thus (9), the bis-sulphinic acid of (1) is reacted with aqueous formaldehyde to yield the bis 1:4-(hydroxy methyl sulphone) butane. These sulphones may be used in treating textiles (see Group IV(c)). The a :o -bis sulphonyl chlorides of decane, dodecane and octadecane are prepared by reacting the corresponding dibromo-alkane with ethanolic thiourea, isolating the resulting isothiouronium bromide and reacting it in aqueous solution with chlorine. 2-Methylbutane-1:4-bis-sulphonyl chloride is prepared by reacting the corresponding dibromo compound with alkyl halide and an alkali metal sulphite and treating the resulting sodium sulphonate with PCl5.ALSO:Textile fabrics are rendered wrinkleresistant by treatment with hydroxy methyl sulphones obtained by reacting formaldehyde with a bi-sulphinic acid of the general formula HO2S-R-SO2H wherein R is a saturated cyclo aliphatic hydrocarbon containing 5 or 6 carbon atoms, the sulphinic groups being attached to different carbon atoms, or a saturated aliphatic hydrocarbon radical containing 4-18 carbon atoms, the two sulphinic groups being separated by a straight chain of at least 4 carbon atoms. In Example (9), cotton fabric is padded in an aqueous bath containing 1 : 4-butane bis(hydroxy methyl sulphone) and MgCl2, and then dried and heat-cured. Numerous other values for R are exemplified. The preparation of the compounds is described (see Group IV(b)).