Patent GB-922403-A (GB)
Title: Triazine dyes and process of producing same
IPC: D06P3/60
Filed: 1959-10-26
Abstract: 1-(21:41- diamino-61- triazinyl) amino-8-hydroxynaphthalene-3:6- disulphonic acid sodium salt and the corresponding 1-N-methyl derivative are made by reacting 2:4-diamino-6-chloro-triazine with 1-amino- or 1-methylamino- 8-hydroxy-naphthalene 3:6-disulphonic acid.  4-(21:41-diamino- 61-triazinyl) amino-aniline is made by hydrolysing the corresponding 1-N-acetyl derivative obtained by condensing 2:4-diamino-6-chloro-triazine with 4-aminoacetanilide. 1-m- (21:41- diamino- 61-triazinyl) aminophenyl-3-methylpyrazolone is made by reacting 1-maminophenyl- 3-methylpyrazolone with 2:4-diamino-6-chlorotriazine.  2:4- bis(methoxymethylamino)- 6-chlorotriazine is made by heating with methanol and oxalic acid a solution containing 2:4-bis(methylolamino)- 6-chlorotriazine obtained by heating 2:4-diamino-6-chloro-triazine with paraformaldehyde dissolved in aqueous methanol containing triethanolamine and sodium hydroxide and adjusted to pH 8-1 with formic acid.ALSO:The invention comprises compounds of the formula <FORM:0922403/IV(a)/1> in which at least one of A and B is the residue of a dyestuff or leuco dye-forming molecule substituted by at least one water-solublizing acidic group and by an amino group or groups through which it is linked to the triazine ring or rings, n is a positive integer which is one when B is the same as A, at least one of B and C is hydroxymethylamino, bis(hydroxymethyl)amino, alkoxymethylamino or bis-(alkoxymethyl)amino and B is the same as C when it is not the same as A.  Dyestuff and leuco-compound residues specified for A are those of the mono-, dis-, tris- and tetrakis-azo, stilbene-azo, anthraquinone, phthalocyanine, xanthene, acridine and azine series and leuco compounds of anthraquinone dyes.  The compounds of the above formula are made by heating in aqueous solution a dyestuff having at least one water-solubilizing acidic group and at least one amino group having a replaceable hydrogen atom (a) with a 2-chloro-4:6-diamino-1:3:5-triazine or a 2:4-dichloro-6-amino-1:3:5-triazine having on each amino group at least one hydroxymethyl or alkoxymethyl group, or (b) with 2-chloro-4:6-diamino-1:3:5-triazine or 2:4-dichloro-6-amino-1:3:5-triazine and heating the product with formaldehyde in an aqueous alkaline medium.  The compounds may also be made by heating 2-chloro-4:6-diamino-1:3:5-triazine or 2:4-dichloro-6-amino-1:3:5-triazine (a) with an amino substituted coupling component and then coupling this with a diazo component, or (b) with an acylamino arylamine and then hydrolysing off the acyl group, diazotizing the product and coupling with a coupling component, at least one of the coupling component and the diazo component or acylamino arylamine containing at least one acidic, water-solubilizing group, and then heating the azo-dyes obtained with formaldehyde in aqueous alkali.  The compounds containing alkoxymethyl groups can also be made by reacting the corresponding methylol compounds with an alcohol in an aqueous acid medium. Examples are given.  The dyes dye, pad or print cellulosic fibres such as cotton, viscose rayon, acetate rayon and cuprammonium rayon and blends thereof or blends of these fibres with nylon, glycol polyterephthalate or polyacrylonitrile and are fixed to the fibre by a heat curing treatment, preferably in the presence of an acid catalyst such as magnesium chloride, zinc chloride or isopropylamine hydrochloride.  In examples, (1) and (4), dyes of the above formula in an ammonium sulphate-sulphuric acid aqueous solution or in an aqueous solution containing sodium chloride, isopropylamine hydrochlorides and trimethylol melamine is applied to cotton which is dried and then cured at 350 DEG F.