Patent GB-927713-A (GB)
Title: New anthraquinone vat dyestuffs and process for their manufacture
IPC: C09B1/467
Filed: 1961-03-01
Abstract: 3-aminobenzene-sulphonic acid-N:g -(N1:N1-bis-hydroxyethyl)-aminopropylamide is made by reducing 3-nitrobenzene-sulphonic acid-N:g -[N1:N1-bis-(hydroxyethyl)] - aminopropylamide which is obtained by condensing m-nitro-benzene-sulphochloride with N:N-bis-(hydroxyethyl)-propylene-diamine-(1:3).  Specification 902,364 is referred to.ALSO:The invention comprises vat dyes which contain a 1:3:5-triazine residue linked through amino groups either directly or via benzoylamino groups to the nuclei of two identical or different anthraquinone radicals and at least one sulphonic acid -N-(sulphatoalkyl)-amide group having at least 3 carbon atoms between the sulphate group and the amide nitrogen atom the alkyl chain being uninterrupted or interrupted by an oxygen, sulphur or nitrogen atom. The sulphonamide group or groups may be attached directly to the anthraquinone nucleus or to a phenyl group attached directly or via an amino group to the triazine ring. Anthraquinone radicals specified are the unsubstituted radical or those substituted by acyl, acylamino or amino and the acedianthrone radical.  Dyes preferred are those of the formula <FORM:0927713/IV(a)/1> in which m, n and p are each 1 or 2, A1 and A2 are anthraquinone radicals and R is an alkylene chain of 4 or 5 carbon atoms, and examples of these are given.  Other dyes specified fall within the above formula but R has 3 carbon atoms or is interrupted by an amino, methylamino or b -sulphato ethylamino group and/or the sulphonamide nitrogen is substituted by methyl. Further dyes specified are of the formulae <FORM:0927713/IV(a)/2> The dyes are made by sulphating the corresponding dyes containing sulphonic acid -N-(hydroxyalkyl)amide groups.  The dyes dye and print textile materials of natural or regenerated cellulose and it is stated that in the dyebath or on the fibre under the influence of alkali the sulphate radical is probably split off with the formation of a heterocyclic ring with the sulphonamide nitrogen atom and an insoluble compound is formed.  The hydroxy compounds corresponding to dyes of Formula I above where m=n=1 and p=1 are made by condensing a hydroxyalkylamine with the appropriate dyestuff sulphochloride which may be made for example by treating a 2-phenyl-4:6-dichloro-triazine sulphochloride with 2 mols. of an aminoanthraquinone.  Hydroxy compounds where m=n=1 and p=2 are made by condensing a bis-(anthraquinonylamino)-chloro-triazine with an aminobenzenesulphon-N-(hydroxyalkyl)-amide.  Hydroxy compounds where m=n=2 and p=2 are made by condensing a di-acid halide of a bis(carboxyphenylamino)-chloro-triazine with 2 mols. of an aminoanthraquinone and then with an amino-benzene-sulphon-N-(hydroxyalkyl)amide.  The hydroxy compound corresponding to the dye of Formula II above is made by condensing the bis-acid chloride of 2:4-bis-(41-carboxyphenylamino)-6-chloro-1:3:5-triazine with 2 mols. of 1-amino-5-nitro-anthraquinone and then with aniline, reducing the nitro groups, condensing with the dichloride of p-sulphobenzoic acid and reacting the product with 4-aminobutanol.  The hydroxy compound corresponding to the dye of Formula III is made by condensing 1 - nitro - anthraquinone - 6- sulpho - chloride with 4-amino-butanol, reducing the nitro group and condensing 2 mols. of the product with 2-phenyl-4:6-dichloro-1:3:5-triazine.  Specification 902,364 is referred to.