Patent GB-988972-A (GB)
Title: Monoazo dyestuffs, their metal complex compounds, and a process for their production
IPC: C07D513/04
Filed: 1963-05-27
Abstract: Compounds of formula <FORM:0988972/C2/1> wherein A and B are hydrogen, alkyl, alkoxy, halogen, sulphonic acid, sulphamyl, nitro or acetylamino substituents and R1 is an alkyl, phenyl, carboxymethyl, carbamyl or ethoxycarbonylmethyl substituent are prepared by ring-closing compounds of formula <FORM:0988972/C2/2> In Example (6) 2,5,7-trimethyl-pyrazolo-[1,5-b]-[1,2,4] - benzothiadiazine - 1,1 - dioxide is prepared by condensing diketene with phenol, adding 3,5-dimethyl-2-aminobenzene sulphonic acid hydrazide to the mixture, recovering the 1-(21 - amino - 31,51-dimethyl-phenylsulphonyl)-3-methyl - 5 - pyrazolone and heating this with a mixture of methanol and hydrochloric acid to effect ring closure.  In Example (7) 2-methyl-pyrazolo - [1,5 - b] - [1,2,4] - benzothiadiazine-1,1-dioxide is prepared by condensing 2-nitrobenzene-sulphonic acid hydrazide with ethyl acetoacetate, hydrogenating the nitro compound in aqueous methanol with a nickel catalyst to give 1 - (o - aminophenylsulphonyl) - 3 - methyl - 5 - pyrazolone and ring-closing this by heating in aqueous hydrochloric acid.ALSO:The invention comprises azo dyes of formula <FORM:0988972/C4-C5/1> wherein R is the radical of a diazo component having X in O-position to the azo bridge, A and B which are the same or different are hydrogen or halogen atoms or nitro, acylamino, alkyl, alkoxy, carboxylic acid, sulphonic acid, sulphonamide and sulphone groups, R1 is a hydrogen atom or an alkyl, aryl, carboxymethyl, carboxylic acid amide or alkoxycarbonylmethyl group and X is a group capable of forming a metal complex or an atom or grouping which can be converted to a group of this type under metallizing conditions (i.e. hydrogen or chlorine atom or a hydroxyl, alkoxy, sulphonic or carboxylic acid group); and the metal complexes of these dyes.  The dyes are prepared by coupling appropriate diazonium compounds with pyrazolo-[1,5,b]-[1,2,4]-benzothiadizine-1, 1-dioxides.  The metal complexes are prepared by known methods in substance or on the fibre (see Division D1), the specified metals being copper, cobalt, chromium and nickel.  The unmetallized dyes may be used to colour polyester and cellulose triacetate materials and the metallized dyes to colour wool in orange, red, violet and brown shades. Examples describe the preparation of the dyes.ALSO:Metal complexes of azo dyes of formula <FORM:0988972/D1-D2/1> wherein R is the radical of a diazo component having X in o-position to the azo bridge, A and B which are the same or different are hydrogen or halogen atoms or nitro, acylamino, alkyl, alkoxy, carboxylic acid, sulphonic acid, sulphonamide and sulphone groups, R1 is a hydrogen atom or an alkyl, aryl, carboxymethyl, carboxylic acid amide or alkoxycarbonylmethyl group and X is a metallisable group or an atom or group convertible thereto under metallising conditions are formed on the fibre by the usual processes.  Specified metallising agents are salts of copper, chromium, cobalt and nickel.  In Example (3) wool is dyed from an aqueous acidic bath at 100 DEG C. with the dye of formula <FORM:0988972/D1-D2/2> potassium dichromate solution is added to the bath and the heating continued for 45 minutes.  A bluishbordeaux shade is obtained. Further chromed dyeings on wool are specified in Examples 3 and 5.