Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

The readily accessible 1,4:3,6‐dianhydroalditols with D‐gluco‐ ( 1 ), L‐ido‐ ( 5 ) and D‐mannoconfigurations ( 6 ) were efficiently transformed into the 2,5‐diamino‐1,4:3,6‐dianhydro‐2,5‐dideoxyalditols with D‐gluco‐ ( 10 ), D‐manno‐ ( 13 ), and L‐ido‐configuration ( 16 ). Interfacial polycondensation of these chiral heterocyclic diamines as well as ethylene‐ and tetramethylene diamine with the bis(chloroformate) 3 derived from 1,4:3,6‐dianhydro‐D‐sorbitol gave the polyurethanes 17 to 21 . Their number‐average molecular weights were determined to be M̄ n ≈ 3000 corresponding to an average degree of polymerisation P̄ n ≈ 20. Inherent viscosities were measured, and 1 H NMR spectroscopy as well as DSC gave informations about the molecular structure and some polymer properties.