Polyurethanes. I. The solution polymerization of diisocyanates with ethylene glycol

Contrary to statements in the literature, it was found that useful polyurethanes could be prepared by the reaction of a diisocyanate with ethylene glycol. In this investigation m-phenylene diisocyanate, p-phenylene diisocyanate, 2, 4-toluene diisocyanate, methylene bis(4-phenyl isocyanate), durene diisocyanate, biphenylene diisocyanate, bis(4-isocyanatophenyl) sulfone, 4,4′-diisocyanatodiphenyl ether, 3,3′-dimethyl-4,4′-biphenylene diisocyanate, and 1,5-naphthalene diisocyanate reacted with ethylene glycol in solution to give the corresponding polyurethanes. The reaction of methylene bis(4-phenyl isocyanate) with ethylene glycol in dimethyl sulfoxide/4-methylpentanone-2 (50/50) gave a high molecular weight, linear polyurethane that could be solvent-cast into films and dry-spun into fibers. These films and fibers showed properties similar to those of existing commercial films and fibers.