Patent GB-930612-A (GB)
Title: New dyestuffs containing carboxylic ester groups
Inventor: LODGE FRANK
IPC: C09B62/515
Filed: 1959-10-12
Abstract: 3-Nitro- 4-chlorobenzeneb -acetoxyethyl sulphone is obtained by acetylating the product obtained by reacting the sodium salt of 3-nitro-4-chlorobenzenesulphinic acid with ethylene chlorohydrin. 2-Nitrodiphenylamine- 4-sulphon- N-(b -hydroxyethyl) amide is obtained by reacting 3 - nitro - 4chlorobenzenesulphone-N- (b -hydroxyethyl) amide with aniline. 2-Amino-6-(b -hydroxyethylsulphonyl) benzthiazole is obtained by reacting bromine with a solution of 4-(b -hydroxyethyl sulphonyl) aniline and potassium thio-cyanate and boiling the product with aqueous hydrochloric acid.ALSO:The invention comprises dyestuffs of the azo (including metallized azo), anthraquinone and o-nitrodiphenylamine series which are free from carboxylic acid groups which do not form part of a metal complex system and from sulphonic acid groups which dyestuffs are characterized by the presence, attached to a carbon atom of the dyestuff, of a group of the formula <FORM:0930612/IV(a)/1> wherein R stands for a hydrogen atom or an alkyl, substituted alkyl, cycloalkyl, aralkyl, aryl or substituted aryl radical, R1, R2 and R3 independently stand for hydrogen or for lower alkyl groups, n stands for 2 or preferably 1, and Y stands for a hydrocarbon or substituted hydrocarbon radical.  The term "lower alkyl" is used to denote alkyl radicals containing from 1 to 4 carbon atoms.  The dyestuffs are produced by reacting appropriate dyestuffs containing a group of the formula <FORM:0930612/IV(a)/2> with a monobasic carboxylic acid of the formula Y.  COOH or a derivative thereof which may be used as an acylating agent, e.g. the anhydride or acid halide, or by reacting together dyestuff intermediates containing a group of the formula <FORM:0930612/IV(a)/3> by methods known to be capable of converting dyestuff intermediates into dyestuffs.  Ampng the many starting materials specified for the production of azo dyes are amino phenols substituted with 4-b - hydroxyethyl sulphonyl, sulphonamido, nitro, chloro, methoxy and methyl groups, anthranilic acid, amino naphthols, p-nitraniline and 2-amino-6-(b -hydroxyethyl sulphonyl) benzthiazole for use as diazo components, p-coupling amines of the benzene or naphthalene series, pyrazolones, acetoacetanilides, phenols and naphthols for use as coupling components substituted with such substituents as cyanoethyl, sulphonamido, methoxy, acetyl, carbethoxyamino, sulphone, nitro, chloro and trifluoromethyl groups.  Among the starting materials specified for the production of anthraquinone dyes are such products as those obtained by condensing 1-amino-4-bromo with 3 or 4-b -hydroxyethyl sulphonyl aniline or b -hydroxyethyl sulphonyl aniline. Nitro dyes specified for use as starting material include condensation products obtained from 4-chloro-3-nitrophenyl-b -hydroxyethyl sulphone or 4-chloro-3-nitrobenzene sulphon-b -hydroxyethyl amide with a primary aromatic amine of the benzene series, e.g. aniline, a toluidine, an anisidine, an aminodiphenyl, a carbon-amidoaniline, an alkyl sulphonylaniline, a halogenated aniline or a phenylene diamine.  Acylating agents specified include such compounds as acetic, butyric, acrylic, crotonic, benzoic, methoxy-, nitro-, and chlorobenzoic acid, monodi- and trichlor-acetic acids and acetoacetic acids and various anhydrides and acid halides derived from such acids.  Metals which may be used in the metal complex dyes include, manganese, vanadium, iron, nickel, copper, zinc, chromium and cobalt and suitable metal yielding agents are specified.  Many examples are furnished.  The dyes are particularly suitable for dyeing wool, silk and synthetic polyamide fibres.