Patent GB-830847-A (GB)
Title: New water-soluble colouring matters containing a n-substituted sulphonamide group
IPC: C09B62/54
Filed: 1957-11-01
Abstract: 4 - Aminobenzene - sulphon - N - (gamma - chloro - beta - hydroxypropyl) - amide hyrdochloride is made by reacting acetanilide-4-sulphonyl chloride with 3-chloro-2-hydroxypropyl-amine hydrochloride to give 4-acetamidobenzene - sulphon - N - (gamma - chloro - beta - hydroxypropyl) - amide, which is hydrolysed.  4 - Aminobenzene - sulphon - N - (gamma - chlorobeta - hydroxypropyl) - amide hydrobromide is made in an analogous manner.  3 - Aminobenzene - sulphon - N - (gamma - chloro - beta - hydroxypropyl) - amide hydrochloride is made by reacting nitrobenzene-3-sulphonyl chloride with 3-chloro-2-hydroxy-propylamine hydrochloride to obtain 3-nitro-benzene - sulphon - N - (gamma - chloro - beta - hydroxypropyl)-amide which is reduced.  3 - Aminobenzene - sulphon - N - (gamma - chloro - beta - hydroxypropyl) - anilide is made by reacting 3-nitrobenzene-sulphon-anilide with epichlorhydrin to give 3-nitrobenzene-sulphon-N - (gamma - chloro - beta - hydroxypropyl) - ani-lide which is then reduced.  2 - Naphthol - 6 - sulphon - N - (gamma - chloro - beta - hydroxypropyl) - amide is made by reacting 2 - hydroxy - 6 - chlorosulphonyl - 1 - naphthoic acid with 3-chloro-2-hydroxy-propyl-amine hydrochloride to give 2-hydroxy-6-(N-gamma - chloro - beta - hydroxypropyl) - sulph-amyl-1-naphthoic acid which is boiled with hydrochloric acid and acetone to remove the carboxy group.  Specifications 515,637 and 712,771 are referred to.ALSO:The invention comprises water-soluble colouring matters containing at least one sulphamyl group in which the nitrogen atom carries at least one substituent of the formula <FORM:0830847/IV(c)/1> where X is chlorine or bromine, the colouring matters also containing at least one sulphonic acid or carboxylic acid group. The colouring matters specified are dyestuffs of the azo, anthraquinone and phthalocyanine series.  The colouring matters may be made by treating a dyestuff containing at least 2 sulphon-chloride groups with a primary or secondary amine containing at least one 3-chloro- or -bromo-2-hydroxy-propyl group attached to the nitrogen atom so that at least one of the sulphonchloride groups is converted to a sulphamyl group of the type specified and at least one is hydrolysed to sulphonic acid. Colouring matters of the azo or polyazo series may be made by using anilines, aminophenols, naphthylamines, aminonaphthols, naphthols, phenols, and pyrazolones containing the above described sulphamyl groups as diazo components and/or coupling components in the conventional coupling reactions, and where the dyestuffs obtained contain o:o1-dihydroxyazo or o-hydroxycarboxy groups, they may be treated with agents yielding metal to form the metal derivatives.  The colouring matters dye or print protein fibres such as wool and silk and synthetic fibres such as nylon and polyacrylonitrile by conventional methods such as from hot neutral or weakly acid baths, and cellulose fibres such as cotton, viscose rayon and linen in conjunction with a treatment with an alkali.  Examples are given.  Specifications 515,637 and 712,771 are referred to.