GB885814A - Water-soluble dyestuffs containing unsaturated carboxylic acid residues - Google Patents

Abstract

The invention comprises water-soluble organic dyes which contain at least one group imparting solubility in water and the residue of an a ,b -unsaturated aliphatic carboxylic acid which has three carbon atoms and is bound to an aromatic nucleus through an amino bridge of formula <FORM:0885814/IV (c)/1> where n is an integer, preferably 1. The dyes may be made by conventional methods by condensation or by diazotisation and coupling of appropriate components or by acylation of appropriate dyes. Indicated are stilbene, acid phthalocyanine, acid anthraquinone, oxazine and especially mono- and poly-azo dyes which may be metallized, copper, cobalt and chromium complexes being mentioned. Indicated unsaturated residues are CH2­CH-CO, which may contain an a - or b -negative substituent such as a halogen atom, HC-C-CO and especially -N(C(n-1)H(2n-1)CO-C(X)=CH-X where n is an integer, preferably 1, and one X is H and the other H or Cl. Indicated water-solubilising groups are sulphonamide, which may be acylated, methylsulphonyl, carboxy or sulphonic acid. Other substituents indicated are halogen, nitro, acylamino, alkyl and alkoxy. Indicative of starting dyes to be acylated are amino-azo-dyes obtained by hydrolysing acylamino-azo or reducing nitro-azo dyes, dyes made by coupling diazotised aromatic amines with acylatable coupling components such as 1-amino-3-alkyl-and -acylamino-benzenes, b -ketocarboxylic acid arylides, m- or p-aminophenyl-5-pyrazolone and aminonaphthol sulphonic acids, 1-amino-4-(31-or 41 - aminophenylamino) - anthraquinone - 2 - sulphonic acid, 1-amino-4-(41-aminophenylamino)-anthraquinone-2, 21-di- and 2,31,8-tri-sulphonic acids, 1,5-dihydroxy-4,8-diaminoanthraquinone-2-sulphonic acid, 1,4-diaminoanthraquinone-2-sulphonic acid, 8-amino-1-acrylaminoanthraquinone, aminodibenzanthrone sulphonic acid ands dyes obtained by the partial amidation of 1 mol proportion of a tri- or tetra-sulphonic acid chloride of an anthraquinone or phthalocyanine dye with 1 mol proportion of an aromatic diamine, or a monoacyl derivative thereof, with subsequent hydrolysis of unreacted sulphonic acid chloride groups, and the acylamino group, if present. The dyes are used especially to colour polyhydroxylated fibrous materials, e.g. regenerated cellulose, cotton and linen, and are preferably used in conjunction with a treatment with an alkali and heat. The dyes also colour nitrogenous materials, e.g. leather, silk, wool and superpolyamide and -urethane fibres, from a weakly alkaline to acid bath. Examples are provided of the preparation of the dyes and their use in colouring processes various shades of red, blue, yellow and green being obtained.