Patent GB-735654-A (GB)
Title: 5-nitro thiazoleazo-n:n-substituted aniline compounds
IPC: C09B29/033
Filed: 1952-12-19
Abstract: The invention comprises azo dyes of the formula <FORM:0735654/IV (c)/1> where R is C1-C10 alkyl, C5-C6 alkoxyalkyl or alkoxyhydroxyalkyl, C2-C5 hydroxyalkyl, C2 -C4 sulphoalkyl, cyanoalkyl, sulphatoalkyl, phosphatoalkyl, phosphonoalkyl (the last four having 2-5 carbon atoms in the alkyl groups), b -nitroethyl, C2-C4 alkenyl, or -(CH2)m-COOR2, where m is 1-3 and R2 is C1-C4 alkyl; R1 is phenyl, chlorophenyl, xenyl or pyridyl; X is hydrogen, C1-C6 alkyl, cyano, trifluoromethyl or phenyl (optionally substituted by nitro, chlorine, bromine, fluorine, or C1-C4 alkyl); Z and Z1 are C1-C4 alkyl, C1-C4 alkoxy, chlorine, bromine, fluorine or -NH-CO-Y (Y is C1-C3 alkyl), and n and n1 are 0-2.  These dyes are made by diazotizing a 2 - amino - 4 - X - 5 - nitrothiazole and coupling with the appropriate substituted aniline.  The dyes give violet or blue shades on cellulose esters, polyethylene terephthalate, modified acrylonitrile, nylon, wool and silk.  Examples show the preparation of dyes from the following components, diazotization being effected with a solution of nitrosyl sulphuric acid in acetic and propionic acids; the coupling component is also dissolved in an acetic-propionic acid mixture, both solutions being substantially free from water. Diazo components: 2-amino-5-nitrothiazole and its derivatives substituted in the 4-position by methyl, ethyl, n-butyl, n-hexyl, trifluoromethyl, cyano, phenyl, tolyl, butylphenyl, bromophenyl, chlorophenyl, fluorophenyl and nitrophenyl.  Coupling components: substituted diphenylamines: N-(b -hydroxyethyl)-3 - methyl, N - (b  : g  - dihydroxypropyl) - 3 - methyl, N - (b  : g  - dihydroxypropyl) - 2 - methoxy - 5 - chloro, N - (b  : g  - dihydroxypropyl) - 3 - chloro, N - (b  : g  - dihydroxypropyl) - 41 - phenyl, N - (b  - hydroxyethyl), N - (b  : g  - dihydroxypropyl), N - (b  - hydroxyethyl) - 3 - bromo, N - (b  - hydroxyethyl) - 3 - methoxy, N - (g  - hydroxypropyl), N - (d  - hydroxybutyl), N - (b  : g  - dihydroxypropyl) - 41 - phenyl - 3 - chloro, N - (b  - hydroxyethyl) - 3 - acetamino, N - ethyl, N - isopropyl - 3 - methyl, N - n - decyl - 3 - chloro, N - (b  - methoxyethyl), N - (b  - propoxyethyl), N - (d  : e  - dihydroxyamyl) - 3 - methyl, N - (b  - cyanoethyl), N - (b  - sulphatoethyl), N - (g  - sulphatopropyl), N - (b  - phosphatoethyl) - 3 - methyl, N - (b  - phosphonoethyl), N - (d - phosphonobutyl), N - vinyl, N - vinyl - 41 - phenyl, N - methallyl, N - carbomethoxymethyl, N - carbethoxymethyl, N - (b  - carbomethoxyethyl) - 3 - chloro, N - (g  - carbomethoxypropyl), N - (g  - carbobutoxypropyl), N - (b  - carbomethoxyethyl) - 41 - phenyl, N - (b  - sulphoethyl); substituted N - pyridyl - anilines: N - (b  : g  - dihydroxypropyl) - N - (2 - pyridyl) - m - toluidine, N - (b  - hydroxyethyl) - N - (2 - pyridyl) - m - toluidine, N - (b  - hydroxyethyl) - N - (2 - pyridyl) - m - chloroaniline, N - (b  : g  - dihydroxypropyl) - N - (2 - pyridyl) - m - chloroaniline, N - (b  - hydroxyethyl) - N - (2 - pyridyl) - cresidine, N - (g  - cyanopropyl) - N - (2 - pyridyl) - aniline, N - vinyl - N - (2 - pyridyl) - aniline and N - (b  - sulphoethyl) - N - (2 - pyridyl) - aniline. Many other suitable components are mentioned.  The dyes may be applied to textile materials in aqueous dispersion together with sodium lignin sulphonate, turkey red oil, soap or oleyl glyceryl sulphate.ALSO:The Specification contains the subject matter of the parent Specification concerning the preparation of certain 2-amino-4-substituted thiazoles and their 5-nitro derivatives.  It is also stated that 2-amino-4-alkylthiazoles in which the alkyl group has 1-6 carbon atoms can be prepared from 1-chloro-2-alkanones and thiourea and then nitrated in the 5-position. 2-Amino-4-methyl-thiazole is mentioned.