Patent GB-971920-A (GB)
Title: New dyestuffs
IPC: C09B62/78
Filed: 1962-03-07
Abstract: The invention comprises dyestuffs of the general formula <FORM:0971920/C4-C5/1> wherein F denotes the radical of an organic dyestuff, Z is a direct bond or a bridge member, Y stands for O, S or NH, r represents a hydrogen atom or an organic substituent or R can be a substituent of a heterocyclic ring, in which the grouping <FORM:0971920/C4-C5/2> can also be included, X is the residue of an aliphatic, aromatic or hydroaromatic carboxylic acid an n is a whole number and process for the production thereof wherein dyestuffs or dyestuff intermediates which contain at least one grouping of the general formula <FORM:0971920/C4-C5/3> wherein R and Y have the same meanings as above are reacted with formaldehyde or a formaldehyde-yielding agent to give the corresponding methylol compound, esterifying this compound with an aliphatic, aromatic, or hydroaromatic carboxylic acid and in the case of a dyestuff intermediate, transforming the latter into the desired final dyestuff.  Starting material dyestuffs may be of the mono- and disazo, azo-methine, polymethine and anthraquinone dyestuffs, as well as their substitution and condensation products, oxazine and dioxazine, azine, thiazine, indigo, quinophthalone, acridine, thiazole, xanthene, nitro, nitroso and triphenyl methane dyestuffs as well as benzanthrone and dibenzathrone series dyes. Monoazo, polyazo and azomethine dyes containing metal-complex forming groupings may be employed in the form of metal complexes, e.g. copper, cobalt, chromium, iron and nickel complexes or the dyes may be metallized on the fibre. Phthalocyanines mentioned include cobalt, copper and nickel phthalocyanines as well as metal free phtholocyanines.  The dyes can be fixed on cellulose from an acid medium. Wool, silk, synthetic polyamide and polyurethane fibres are also dye or printed with the dyes in the usual manner.  Among the examples are described processes wherein the dyestuff p-sulphanilic acid --> 1-phenyl-5-pyrazolone-3-carboxylic acid amide is heated with paraformaldehyde and acetic acid and the product heated with acetic anhydride (1); p-sulphanilic acid --> 3-methyl-5-pyrazolone is treated with paraformaldehyde and acetic acid (2); the product obtained by reacting 2-sulpho-diethyl-amino-benzaldehyde with cyanoacetamide is reacted as described above (3); the product obtained by reacting 1-amino-4-bromo-anthraquinone - 2 - sulphonic acid and 4 - amino-benzoic amide is reacted with paraformaldehyde and glacial acetic acid (5); 1-phenyl-5-pyrazolone-3-carboxylic acid is reacted with paraformaldehyde and glacial acetic acid and the product coupled with diazotized p-sulphanilic acid (6); the dyestuff 4-amino-benzoic amide --> 1 - hydroxy - 8 - acetylamino naphthalene-3,6-disulphonic acid is reacted with paraformaldehyde and propionic acid (8); the product obtained by reacting 1,3,3-trimethyl-2-methyleneindoline -5-sulphonic acid and 1-phenyl-4-dimethylaminomethylene - pyrazolone - 3 - carboxylic acid is condensed with paraformaldehyde and glacial acetic acid (10); the 2: 1-chromium complex of 1-amino-2-hydroxy-benzene - 4 - sulphonic acid --> 1 - phenyl - 5 - pyrazolone - 3 - carboxylic amide is condensed with paraformaldehyde and glacial acetic acid (12); 1 - amino - 4 - (31 - ureidophenyl) - amino -anthraquinone-2-sulphonic acid is reacted with paraformaldehyde and glacial acetic acid whilst in other processes 3-amino-phenyl urea --> 1 - (41 - sulphophenyl) - 3 - methyl - 5 - pyrazolone and 4 - aminothiobenzamide --> 1-(41-sulphophenyl) - 3 - methyl - 5 - pyrazolone are employed as starting materials (13); and the 2: 1-chromium complex of 6-nitro-2-amino-1-hydroxybenzene - 4 - sulphonic acid --> 1-phenyl - 5 - pyrazolone - 3 - carboxyli amide is condensed with paraformaldehyde and glacial acetic acid.  Specifications 842,802, 875,712 and 900,950 are referred to.