Synthesis and properties of polyurethanes derived from diaminodianhydroalditols

Authors

  • Joachim Thiem,

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Orléans-Ring 23, D-4400 Münster, FRG
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Orléans-Ring 23, D-4400 Münster, FRG
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  • Harald Lüders

    1. Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, FRG
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Abstract

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 M̄n ≈ 3000 corresponding to an average degree of polymerisation P̄n ≈ 20. Inherent viscosities were measured, and 1H NMR spectroscopy as well as DSC gave informations about the molecular structure and some polymer properties.

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