Patent GB-830446-A (GB)
Title: Process for the preparation of oxidation dyestuffs on textile fibres
Inventor: SUREAU ROBERT FREDERIC MICHEL
IPC: D06P1/32
Filed: 1956-09-19
Abstract: Phenyl-glycine derivatives, for use in the manufacture of oxidation dyestuffs on the fibre (see Group IV (c)), and of the formula <FORM:0830446/IV (b)/1> wherein Z is H or a monovalent cation, Y1 is H or -CH2CO2Z, Y2 is H, alkyl or -CH2CO2Z and Y3 is H, alkyl, aryl or -CH2CO2Z, the benzene nucleus A, if desired, being further substituted by an amino, alkyl or alkoxy group, are obtained by the following methods: (a) the action of aliphatic-mono-halogenated carboxylic acids on diamines, triamines and tetramines of the benzene series, on arylaminophenylamines, alkylaminophenylamines and dialkyl-aminophenylamines, or on acylaminophenylamines with subsequent hydrolysis of the acylamino groups, or on nitrophenylamines with subsequent reduction of the nitro groups; (b) the action of esters or amides of aliphatic-monohalogenated carboxylic acids on the amines of (a) with subsequent hydrolysis of the ester or amide groups; and (c) the condensation of the amines of (a) with aliphatic aldehydes and hydrocyanic acid so as to form nitriles which are then hydrolysed to carboxylic acids.  In examples the preparation of the following derivatives is described :-(1) p-phenylaminophenylglycine; (3) sodium 3 : 4-diaminophenylglycinate; (4) N-(4-aminophenyl)-iminodiacetic acid; (6) N-(4-phenylaminophenyl)-iminodiacetic acid; (8) 3-methoxy-4-aminophenyl glycine; (9) 4-amino-3-methylphenyl glycine;; (10) 4-amino-2-methylphenyl glycine; and (11) 4-dimethylamino-phenylglycine hydrochloride.ALSO:Oxidation dyestuffs are formed on textile fibres by oxidizing thereon a compound of the formula <FORM:0830446/IV(c)/1> wherein Z is H or a monovalent cation, Y1 is H or -CH2CO2Z, Y2 is H, alkyl or -CH2CO2Z and Y3 is H, alkyl, aryl or -CH2CO2Z, the nucleus A, if desired, being substituted in any of the other positions by an amino, alkyl or alkoxy group.  The process may be applied to the dyeing or printing of natural or synthetic fibres, e.g. fibres of natural or regenerated cellulose, wool, silk, cellulose ethers or esters, superpolyamides, superpolyesters, polyvinyl chloride and other substituted vinylidene derivatives.  The compounds can be applied together with, or side-by-side with, sulphuric esters of leuco vat dyestuffs or azoic combinations.  Oxidizing agents, e.g. chlorates, chromates, dichromates, nitrites and peroxides, may be applied together with or subsequently to the compound.  Oxidation catalysts, such as cerium, osmium, vanadium and copper derivatives and also ferrocyanides, may also be employed.  Development is preferably effected by the action of an acid, applied for example from a bath or as a vapour mixed with steam or air. Alternatively, an acid liberating substance such as ammonium salts, organic amides and esters and sulphonates may be applied to the fibre, a subsequent treatment with moist hot air or with neutral or acid steam liberating the acid.  Mixtures of the phenylglycine compounds with other compounds known to yield oxidation dyestuffs may be employed.  The printing pastes or baths may contain solvents, wetting and hygroscopic agents, buffers and premature oxidation inhibitors.  Numerous examples of the printing of cotton fabrics are given.