Preparation of urethane substituted diacetylene monomers and polymers.

摘要

Synthesis of urethane substituted diacetylenes of the formula R-NHOCO(CH2)4-C IDENTICAL C-C IDENTICAL C-(CH2) nOCONH-R where n is an integer of from 1 to 20, R=CH3(CH2) m(COOCH2) p, C6H5(CH2) m(COOCH2) p, C6H11 (CH2) m (COOCH2) p, or C10H7-(CH2) m(COOCH2 p, where m is an integer of from 0 to 11 and p is 0 or 1. The compounds are free of impurities resulting from dehydration of diols of the formula HO-(CH2) nC IDENTICAL C-C IDENTICAL C-(CH2)-OH. The compounds are produced by first reacting an isocyanate of the formula R-NCO with an alcohol of the formula HC IDENTICAL C-(CH2) n-OH, then oxidatively coupling the resulting urethane substituted monoacetylenic compound in the presence of an amine-basic copper salt complex, preferably by bubbling oxygen through the solution. The diaceylenes are polymerized to form the polydiacetylenes. Also disclosed are the monomers and polymers produced.