Patent GB-849772-A (GB)
Title: s-triazine derivatives
Inventor: ATKINSON JOHN REGINALD
IPC: D06P3/66
Filed: 1956-12-21
Abstract: The invention comprises compounds containing at least one s-triazine nucleus to at least one carbon atom of which is attached a sulphonic acid group in the form of its alkali metal or alkaline earth metal (including magnesium) salt.  They may be prepared by reacting the corresponding halogen derivatives with a metal salt of sulphurous acid, preferably in aqueous solution. All or part of the halogen may be replaced.  It is also possible to replace one halogen atom by sulphonate and a second by hydroxyl.  The reaction medium is preferably neutralised to pH 6-8 before isolating the product which may be effected by adding an alkali or alkaline earth metal salt to precipitate the corresponding sulphonate.  Heating the products with acid liberates sulphur dioxide while with aqueous alkalis or alkali/hypochlorite mixtures, all or part of the sulphonate is replaced by hydroxyl.  The halogenated starting materials may contain organic substituents attached to triazine ring carbon through nitrogen, oxygen or sulphur.  Such compounds may be p  obtained by treating a halogenated triaziane with an amine, alcohol, phenol or mercaptan.  Starting materials prepared in Examples are: (10) the sodium salt of (4, 6-dichloro-s-triazinylamino)-benzene-3-sulphonic acid; from metanilic acid and cyanuric chloride; in (19) this is converted with sodium hydrogen sulphide to the disodium salt of (4, 6-dimercapto-s-trazinylamino)-benzene-3-sulphonic acid, which is further reacted with sodium hydroxide/sodium hypochlorite mixture to give the trisodium salt of (4-sulpho-6-hydroxy-s-triazinylamino)- benzene-3-sulphonic acid; in (18) the reaction product of cyanauric chloride and sodium sulphite is reacted with sodium metanilate to give (4, 6-disulpho-s-triazinylamino)-benzene-3-sulphonic acid trisodium salt.  Specification 707,557 is referred to.ALSO:The invention comprises dyestuffs containing at least one s-triazine nucleus to at least one carbon atom of which is attached a sulphonic acid group in the form of its alkali metal or alkaline-earth metal (including magnesium) salt.  They may be prepared by reacting the corresponding halogen compounds with a metal salt of sulphurous acid, preferably in aqueous solution. All or part of the halogen may be replaced.  It is also possible to replace one halogen atom by sulphonate and a second by hydroxyl and to convert the sulphonate group to a hydroxyl group.  The reaction medium is preferably neutralized to pH 6-8 before isolating the product, which may be effected by adding an alkali or alkaline-earth metal salt to precipitate the corresponding sulphonate.  Heating the products with acid liberates SO2, while with aqueous alkalis or alkali/hypochlorite mixtures, all or part of the sulphonate is replaced by hydroxyl.  The halogenated starting materials may contain organic substituents attached to triazine ring carbon through nitrogen, oxygen or sulphur. Such compounds may be obtained by treating a halogenated triazine with an amine, alcohol, phenol or mercaptan.  The products may contain anthraquinone, azo, nitro, naphthalene and phthalocyanine residues, examples being provided.  The preparation of some of the starting materials is also described.  In examples, the dyes are applied by padding or printing to cotton, viscose rayon, nylon and silk.  An acid-binding agent is preferably used before, with or after the dye.  The dyed fabric may be steamed.  Compounds of the invention containing two or more sulphonate groups attached to the triazine ring may be used to attach to cellulose products chemically related thereto, such as starch.  In Example 46 cotton limbric is impregnated with a starch solution, dried and treated with an aqueous sodium bicarbonate solution of trisodium (4, 6-disulpho-s-triazinylamino)-benzene-3-sulphonate, dried and baked to give a stiffened fabric resistant to boiling soap treatment. In Example 47, the starch, bicarbonate and sulphonate are applied together to the cotton.  In Example 50 a cotton cloth is impregnated with a sodium bicarbonate solution of trisodium (4, 6-disulpho-s-triazinylamino)-benzene-3-sulphonate, baked, washed and dried to give a fabric resistant to soiling.  The products may be used to treat textiles dyed or printed with dyes containing amino- or mono-substituted amino groups to increase fastness to washing.  In Example 45 silk, wool or polyacrylonitrile fabric dyed with tetramino anthraquinone is padded with an aqueous solution containing trisodium (4, 6-disulpho -striazinylamino) -benzene -3- sulphonate, dried and acid-steamed; viscose rayon and cotton dyed with a direct dye are treated similarly.  In Example 49 a viscose rayon fabric is impregnated with a sodium carbonate solution of trisodium (4, 6-disulpho -striazinylamino)-benzene -3- sulphonate, dried, printed with a thickened paste comprising the dyestuff composition of Example 2 of Specification 707,557, lactic acid and di(2, 21-hydroxyethyl) sulphide, steamed, acetic acid rinsed, water rinsed, boiled in aqueous soap solution and dried.