Patent GB-787582-A (GB)
Title: Manufacture of water-insoluble monoazo-dyestuffs of the tetrazole series
IPC: C09B29/033
Filed: 1954-09-28
Abstract: Tetrazoles of formula: <FORM:0787582/IV (b)/1> where one X is an aminophenyl residue which may be substituted and the other X is an alkyl, aryl, aralkyl or cycloalkyl residue are made by reacting an imide-chloride obtainable from acylaminonitrobenzenes with hydrazoic acid, or by coupling diazotized aminonitro-benzenes with N,N1-diacyl-hydrazines and subsequently reducing the nitro-compounds so obtained. Tetrazoles obtained in the examples are 1-(31-nitro-41-ethoxyphenyl) - 5 - methyl - and 1 - benzyl-5 - (21 - nitrophenyl) - 1,2,3,4 tetrazoles and the corresponding amino compounds.  Diazoamino compounds obtained from the above aminotetrazoles by conventional methods are also described, e.g. 1-phenyl-5-(21-aminophenyl) is diazotized and coupled with 1-methylamino-2-carboxybenzene-4-sulphonic acid. For a full list of the described tetrazoles see Group IV (c).ALSO:The invention comprises dyestuffs of formula <FORM:0787582/IV (b)/1> where X is an alkyl, aryl, aralkyl or cycloalkyl residue, R is the residue of an aromatic or heterocyclic o-hydroxycarboxylic acid arylide or acylacetic acid arylide, A is a tetrazole residue of formula <FORM:0787582/IV (b)/2> nucleus a may contain substituents and the components are free from groups imparting solubility in water such as SO3H and COOH groups.  The dyestuffs are made by coupling in substance, on the fibre or on a subtratum suitable for colour lakes, a diazo-compound of an amine of formula <FORM:0787582/IV (b)/3> where one X is an aminophenyl radicle, optionally substituted, and the other is an alkyl, aryl, aralkyl or cycloalkyl residue with the appropriate coupling component.  Indicated as coupling components are arylides of 2-naphthol-3-, 2-hydroxyanthracene-3-, 3-hydroxy-diphenylene oxide-2-, 2-hydroxycarbazole-3- and 5 - hydroxy - 1,2,11,21 - benzocarbazole - 4 carboxylic acids, acetoacetic acid and terephthaloyl-bis-acetic acid. Diazo-components may be used as stabilized compounds, e.g. as the zinc chloride double salt, diazoamino-compounds or antidiazotates. The dyestuffs dye vegetable and regenerated cellulose, acetyl-cellulose, polyamide and polyurethane fibres and colour films of cellulose ethers and esters and plastic masses.  In examples, and a Table, which illustrate the preparation of the dyestuffs and their use in conventional dyeing and colouring processes the effective diazo components, sometimes used as diazoamino-compounds or antidiazotates are derived from 1 - (41 - amino -, 31 - amino - 21 - and - 41, methyl and -21,41- and -41,61-dimethyl-, 31-amino-41-methoxy- and -ethoxy-, 41-amino-21,51-dimethoxy- and -diethoxy-, 41-amino-31-methyl - 61 - methoxy - and - 21 - methyl - 51-methoxy-, 41-amino-31-chloro-, 41-amino-21 methyl- and -methoxy-51-chloro- and 21-amino-41,51 - dichloro - phenyl) - 5 - methyl - 1,2,3,4-, 1 - (31 - amino - 41 - ethoxy -, 41 - amino - 21,51-diethoxy- and 21-amino-41,51-dimethyl-phenyl)-5 - ethyl - 1,2,3,4 -, 1 - (41 - amino -, 31 - amino-41- and -51-ethoxy- and 41-amino-21,51-dimethoxy- and diethoxy-phenyl)-5-n-propyl-1,2,3,4-, 1-(41-amino-, 31-amino-41-methoxy-and -ethoxy-, 41-amino-21,51-dimethoxy- and -diethoxy - phenyl) - 5 - cyclohexyl - 1,2,3,4 -, 1-methyl - 5 - (31 - amino -, 31 - amino - 41-methyl-, -ethoxy- and -methoxy-, 21-amino-51-chlorophenyl) - 1,2,3,4 -, 1 - ethyl - 5 - (41-aminophenyl) - 1,2,3,4 -, 1 - n - butyl - 5 - (31-amino - 41 - ethoxy - and - methoxy - phenyl)-1,2,3,4 -, 1 - cyclohexyl - 5 - (31 - amino - 41-methoxyphenyl) - 1,2,3,4 -, 1 - phenyl - 5 - (21-amino -, 21 - amino - 41 - methyl -, 31 - amino-41 - methoxy - and - ethoxy - and - 61 - chlorophenyl) - 1,2,3,4 -, 1 - (41 - amino - 21,51 - di-ethoxyphenyl) - 5 - phenyl - and -benzyl-1,2,3,4 - 1 - (31 - amino - 41 - ethoxyphenyl) - 5-(41 - methyl - and - chloro - and 31 - methoxyphenyl) - 1,2,3,4 -, 1 - (41 - chloro - and - methylphenyl) - 5 - (21 - aminophenyl) - 1,2,3,4 -, 1 -(21-methoxy- and 41-ethoxy-phenyl)-5-(31-amino-41 - methoxyphenyl) - 1,2,3,4 - and 1 - benzyl-5 - (21 - aminophenyl) - 1,2,3,4 - tetrazoles the arylides being 1-(2,31-hydroxynaphthoylamino) - 2 - methyl - methoxy - and - ethoxy-, - 2 - methyl - 4 - chloro - and - methoxy -, -2,5-dimethoxy-4-, and -2,4-dimethoxy-5-chloro-2-methoxy-5-chloro-, -4-chloro- and -methoxy-and 2 - methoxy - 4 - chloro - 5 - methylbenzenes, 21,31 - hydroxynaphthoylaminobenzene and -1- and -2-naphthalenes, 1-(61-bromo - 21, 31 - hydroxynaphthoylamino)-2 - methoxybenzene, 2 - (21,31-hydroxynaphthoylamino) - 3 - methoxy - diphenylene oxide, 1 - (21 - hydroxyanthracene - 31 - carboylamino)-2-methylbenzene, 1-(51-hydroxy-11,21,111, 211-benzocarbazole - 41 - carboylamino) - 4 - methoxybenzene, 1-(31-hydroxydiphenylene oxide-21 - carboylamino) - 2,5 - dimethoxybenzene, 4,411 - bis - (211,311 - hydroxynaphthoylamino)-3,31 - dimethyldiphenyl, 1 - (21 - hydroxycarbazole - 31 - carboylamino) - 4 - chlorobenzene, terephthaloyl - bis - (1 - acetylamino - 3 - chloro-4,6 - dimethoxy, and 1 - acetylamino - 2 - methoxy - 4 - chloro - 5 - methyl - benzenes) and 1 - aceto - acetylamino - 2,5 - dimethoxy - 4 - chlorobenzenes, fibres of cotton, acetate-rayon, polyamides and acetyl-cellulose being dyed in red, brown or yellow shades and a polyvinyl chloride composition being coloured red.ALSO:Dyestuffs of formula: <FORM:0787582/IV (a)/1> where X is an alkyl, aryl, aralkyl or cycloalkyl residue, R is the residue of an aromatic or heterocyclic o-hydroxycarboxylic acid arylide or acylacetic acid arylide, A is a tetrazole residue of formula: <FORM:0787582/IV (a)/2> nucleus a may contain substituents and the components are free from groups imparting solubility in water such as sulphonic and carboxylic acid groups, are stated to colour plastic masses.  In Example (6) the dyestuff 1-(31-amino - 41 - ethoxyphenyl) - 5 - cyclohexyl1,2,3,4 - tetrazole -\sY 1 - 1 - (21,31 - hydroxynaphthoylamino) - 2,5 - dimethoxy - 4 - chlorobenzene is added to a mixture of a vinyl chloride polymerization product, d-n-butyl phthalate and titanium dioxide which is then heated and kneaded to yield a red rubber-like mass.