GB631025A - Production of monocyclic aromatic tri-isocyanates - Google Patents

Abstract

Benzene 1 : 3 : 5 - tricarbonimides (triisocyanates) which may be substituted in the 2-position by an alkyl, alkoxy or aryloxy group are applied to cellulose which is then heat treated. Chemical reaction occurs which modifies the surface properties of the cellulosic material. Specified substituents in the 2-position are methyl-, ethyl-, methoxy and phenoxy.ALSO:Monocyclic aromatic tricarbonimides (isocyanates) are prepared by passing phosgene into a suspension of a trihydrochloride of a compound of the formula <FORM:0631025/IV (b)/1> where R is hydrogen, an alkyl group or an alkoxy or aryloxy group, in an organic volatile diluent inert to the reactants and to the characteristic radicals of the reaction products, at a temperature not less than about 90 DEG C., preferably at 90-130 DEG C., while removing the hydrogen chloride liberated. The reaction should be performed in the absence of moisture. The products may be separated and purified by distillation, which is facilitated by using a solvent having a boiling point not exceeding 160 DEG C. Suitable solvents are hydrocarbons, halogenated hydrocarbons or ethers, e.g. toluene, xylene, ligroin, tetrachloroethane orthochlorotoluene, anisole, dioxane, monochlorobenzene or mixtures of these with, e.g. ethylene dichloride or benzene. Hydrochlorides of amino-aryl chloro carboxyamides and aryl trichlorocarbamides are formed as intermediate products. The products react with alcohols for form urethanes with water to give amines and with ammonia or amines to give aryl ureas or aryl alkyl ureas. They may be used to modify the surface properties of cellulose textiles. In examples there is described the treatment with phosgene of monochlorobenzene solutions of (1) 1 : 3 : 5-triaminobenzene trihydrochloride; (2) 2 : 4 : 6-triaminotoluene trihydrochloride; (3) 2 : 4 : 6-triaminoethylbenzene trihydrochloride; (4) 2 : 4 : 6-triaminoanisole trihydrochloride, and (5) 2 : 4 : 6-triamino - 1 - phenoxybenzene trihydrochloride giving in each case the corresponding tricarbonimide. Aromatic triurethanes.-Treatment of the tricarbonimides produced according to examples 1-4 with absolute alcohol gives the corresponding triurethanes. Aromatic tricarbamides.-Treatment of the tricarbonimides produced according to the examples with dry ammonia or amines in ether gives the corresponding tricarbamides. 2 : 4 : 6 - Triamino-anisole hydrochloride is produced by catalytic reduction of trinitro anisole with hydrogen in the presence of Raney nickel. Specification 625,350 is referred to.