Aromatic diisocyano-diisothiocyano-and isocyano-isothiocyano-compounds and polymers obtained therefrom, and the preparation of such compounds and polymers

摘要

Polyurethanes and polythiourethanes are obtained by condensation of polyhydroxy bodies such as polyhydric alcohols, polyalkylene glycols, and polyesters or mixed polyesterpolyesteramides with aromatic compounds containing two groups of the formula -N=C=X, in which X, which may be the same or different in each of the said groups, is oxygen or sulphur, attached to two nuclear carbon atoms, each of the nuclear carbon atoms in ortho positions to the -N=C=X groups being attached by a C-C linkage to an organic radical (see Group IV (b)). In examples: (1) durene diisocyanate is reacted with 1.4-butanediol, (2) durene diisothiocyanate is reacted with 1.10-decanediol, (3) durene diisocyanate is reacted with a polyester produced from adipic acid and a mixture of ethylene and propylene glycols.ALSO:The invention comprises aromatic compounds containing two groups of the formula -N = C = X, in which X, which may be the same or different in each of the said groups, is oxygen or sulphur, attached to two nuclear carbon atoms, each of the nuclear carbon atoms in ortho positions to the -N = C = X groups being attached by a C-C linkage to an organic radical. The products may be used to prepare polymers (see Group IV (a)). They may be made (1) from the corresponding amines and phosgene or thiophosgene; (2) the di-isothiocyanates may be obtained from the corresponding amines, carbon bisulphide, ammonium hydroxide and lead nitrate; (3) the mixed isocyano-isothiocyano compounds may be made by heating the di-isothiocyanates with mercurous oxide. In examples, the following substances are made by reacting the corresponding diamines with phosgene or thiophosgene in chlorbenzene in presence of hydrogen chloride: durene di-isocyanate, durene di-isothiocyanate, prehnitene di-isocyanate, isodurene di-isocyanate, mesitylene diisocyanate, mesitylene di-isothiocyanate, 1.4-dimethyl - 2.3 - di-isocyanobenzene, 1.2 - diisocyano - 3 - methyl - 5.6.7.8 - tetrahydronaphthalene, 1.4 - dimethyl - 2.3 - di - isocyanonaphthalene, 3.5.31.51 - tetramethyl - 4.41 - di isocyanodiphenyl, bis -(2 - isocyano - 3 - methyl-phenyl) methane. The products may be reacted with ethyl, isopropyl, allyl, tert.-butyl, or decyl alcohols to give carbamates.