Synthesis and properties of polyamides derived from anhydro‐ and dianhydroalditols

Abstract

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 1 H/ 13 C NMR spectroscopy. Number‐average molecular weights were obtained from gel‐permeation chromatography to be M̄ n ≈ 5000–25000 corresponding to a number‐average degree of polymerization up to P̄ n ≈ 100. Inherent viscosities were measured, and differential scanning calorimetry gave information on the thermal properties of the polymers.