Synthesis and properties of polyamides derived from anhydro- and dianhydroalditols

Authors

  • Joachim Thiem,

    Corresponding author
    1. Institut für Organische Chemie, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, Federal Republic of Germany
    • Institut für Organische Chemie, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, Federal Republic of Germany
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  • Frank Bachmann

    1. Institut für Organische Chemie, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, Federal Republic of Germany
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Abstract

The three isomeric 1,4:3,6-dianhydroalditols with D-gluco- (2), D-manno- (11) and L-ido (17) configuration and both 1,4-anhydroalditols with threo (22) and erythro (27) configuration were efficiently transformed into the corresponding diamino derivatives. Interfacial polycondensation of these chiral heterocyclic diamines with purchasable aromatic and aliphatic carboxylic acid chlorides gave polyamides 35 and 36a–f, 37, 38 and 39a–d. The polymers were characterized using IR and 1H/13C NMR spectroscopy. Number-average molecular weights were obtained from gel-permeation chromatography to be n ≈ 5000–25000 corresponding to a number-average degree of polymerization up to n ≈ 100. Inherent viscosities were measured, and differential scanning calorimetry gave information on the thermal properties of the polymers.

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