Patent GB-983888-A (GB)
Title: Improvements relating to peridinium azo dyestuffs and their use
IPC: C09B29/36
Filed: 1962-08-24
Abstract: 1,2,3 - Trimethyl - 1,2 - dihydro - 2 - hydroxy-perimidine is obtained by reacting 2-methyl-perimidine with methyl iodide to obtain 2,3-dimethyl-perimidinium iodide, treating an aqueous solution of the latter with sodium hydroxide to obtain 1,2-dimethylperimidine, reacting the latter with dimethyl sulphate to obtain trimethyl-peridinium metho-sulphate, reacting the latter in aqueous solution with potassium iodide and treating an aqueous solution of the product with sodium hydroxide to obtain 1,2,3-trimethyl - 1,2 - dihydro - 2 - hydroxy - perimidine.  1,2 - dimethyl - 3 - ethylperimidinium methosulphate or 1,2 - dimethyl - 3 - ethyl - 1,2 - dihydro - 2 - hydroxy - perimidine are obtained in similar processes using diethyl sulphate.  1,3 - dimethyl - 2 - ethyl - perimidinium methosulphate and 1,3 - dimethyl - 2 - ethyl - 1,2 - dihydro - 2 - hydroxy - perimidine are similarly obtained using 2-ethyl perimidine as starting material.ALSO:The invention comprises basic azo dyestuffs of the general formula <FORM:0983888/C4-C5/1> wherein R represents the radical of a diazo component, containing no groups which dissociate acid, each of R1 and R111 represents an alkyl radical having 1-4 carbon atoms, R11 represents hydrogen or an alkyl radical having 1-4 carbon atoms and X represents an anion and processes for the preparation thereof comprising (a) coupling carbinols of the formula <FORM:0983888/C4-C5/2> with diazonium compounds to form azo dyes and reacting the latter with acids to form salts; (b) reacting azo dyes of the formula <FORM:0983888/C4-C5/3> with an ester of the formula R111-X where X represents the radical of a strong acid or (c) heating azo dyes of the formula <FORM:0983888/C4-C5/4> with aliphatic carboxylic acids having 1-4 carbon atoms or their anhydrides.  The dyes are employed in dyeing wool and fibres of polymers and copolymers of acrylonitrile.  The radical R may be derived from diazotizable primary amines of the homo- and heterocyclic aromatic series, e.g. 3-aminoindazole, 3-aminopyrazole, 5-amino, 1,2,4-triazole, 2-aminotriazole, 2-aminobenzthiazole, 2-amino-1,3,4-thiadiazole which may be substituted with alkyl, aryl, alkoxy, acylamino, alkyl- or aryl-sulphonyl, sulphamyl or nitro groups or halogens. Preferred diazo components are of the benzene series and these may contain substituents such as halogens, cyano, alkyl, aralkyl, alkoxy, aryloxy groups, alkylated, aralkylated, arylated and acylated amino groups, carboxylic and sulphonic acid ester and amide groups which may be further substituted at the nitrogen atom or phenylazo groups with the phenyl group optionally substituted.  The products may be converted to double salts by reaction, e.g. with zinc chloride.  Alkylating agents specified include methyliodide, dimethyl sulphate, p-toluene sulphonic methyl ester and the corresponding ethyl, n-propyl or n-butyl derivatives. Perimidine starting materials specified include 1, 2, 3-trimethyl-1,2-dihydro-2-hydroxy-; 1,3-diethyl-2-methyl-1,2-dihydro-2-hydroxy and 1-ethyl-2-methyl-perimidines. Examples in which many alternative starting materials are specified, are furnished.