IN WHICH X1 AND X2 ARE EQUAL OR DIFFERENT AND REPRESENT A HYDROGEN ATOM, A LOWER ALKYL OR ALKOXY GROUP HAVING 1-4 CARBON ATOMS OR A HALOGEN ATOM, PREFERABLY A CHLORINE OR BROMINE ATOM, AND R REPRESENTS A HYDROGEN OR HALOGEN ATOM, PREFERABLY, A CHLORINE OR BROMINE ATOM, A METHYL, ETHYL, METHOXY OR ETHOXY GROUP. THEY MAY BE PREPARED BY REACTING BENZENESULFOCHLORIDES OF THE GENERAL FORMULA
(A,X1,X2-PHENYL)-SO2-CL
WITH 5-AMINO-BENZIMIDAZOLONES OF THE GENERAL FORMULA
2-(O=),5-NH2,R-BENZIMIDAZOLINE
IN WHICH FORMULAE A REPRESENTS A NITRO OR ACETYLAMINO GROUP AND X1, X2 AND R ARE DEFINED AS ABOVE, AND HYDROLYSING THE ACETYL GROUP IN THE PRODUCTS THUS OBTAINED OR REDUCING THE NITRO GROUP TO THE AMINO GROUP. THESE 5 - (AMINOBENZENESULFONYLAMINO) - BENZIMIDAZOLONES CAN BE COUPLED IN THEIR DIAZOTIZED FORM WITH N-ACETOACETYLAMINO COMPOUNDS OF THE BENZENE-, DIPHENYLAND BENZIMIDAZOLONE SERIES TO MONO AND DISAZO PIGMENTS WHICH ARE DISTINGUISHED BY EXCELLENT PROPERTIES OF FASTNESS AND VERY PURE AND BRILLIANT SHADES.
WHEREIN X1 AND X2 MAY BE IDENTICAL OR DIFFERENT AND REPRESENT A HYDROGEN ATOM, A LOWER ALKYL OR ALKOXY GROUP HAVING PREFERABLY 1 TO 4 CARBON ATOMS, OR A HALOGEN ATOM PERFERABLY A CHLORINE OR BROMINE ATOM, AND R IS A HYDROGEN OR HALOGEN ATOM, METHOXY OR ETHOXY GROUP, N REPATOM, A METHYL, ETHYL, METHOXY OR ETHOXY GROUP, N REPRESENTS THE NUMBERS 1 OR 2 AND A AN OPTIONALLY SUBSTITUTED RADICAL, PREFERABLY OF THE BENZENE, NAPHTHALENE OR BENZIMIDAZOLONE SERIES OF N=1, AND OF THE BENZENE OR DIPHENYL SERIES IF N=2. THESE DYESTUFFS MAY BE USED FOR DYEING OR PRINTING LACQUERS, POLYMERS OR TEXTILE MATERIALS, THEY SHOW A GOOD FASTNESS TO LIGHT, TO WEATHER AND TO MIGRATION. FURTHERMORE, THEY ARE FAST TO HEAT, HAVE A HIGH TINCORIAL STRENGTH TO THE INFLUENCE OF CHEMICAL PRODUCTS, ESPECIALLY SOLVENTS, ACIDS AND ALKALIS.
Abstract:
1,2,4-TRIAMINO BENZENES ARE OBTAINED IN HIGH YIELD AND PURITY BY CATALYTIC HYDROGENATION OF 2,4-DINITRO ANILINES IN WATER CONTAINING AT LEAST ONE MOLAR EQUIVALENT OF A MONO- OR DI-CARBOXYLIC ACID. The products are known and useful as intermediates for dyes and biocides.