Premium
Alternating poly(ester amide)s from succinic anhydride and α,ω‐amino alcohols: synthesis and thermal characterization
Author(s) -
Fey Thomas,
Hölscher Markus,
Keul Helmut,
Höcker Hartwig
Publication year - 2003
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.1354
Subject(s) - amide , succinic anhydride , polyamide , condensation polymer , polymer chemistry , chemistry , succinic acid , proton nmr , organic chemistry , polymer
Alternating poly(ester amide)s 6a – e from succinic anhydride and α,ω‐amino alcohols H 2 N—(CH 2 ) x —OH ( x = 2–6) 2a–e were obtained in two steps: α‐carboxyl‐ω‐hydroxy amides 3a–e were prepared from the starting materials in a highly selective reaction, followed by a polycondensation reaction. 1 H and 13 C NMR analyses of the poly(ester amide)s clearly reveal the alternating microstructure. The poly(ester amide)s with homologous α,ω‐amino alcohols H 2 N—(CH 2 ) x —OH ( x = 2–6) are semi‐crystalline materials, their melting points show the odd/even effect observed for [n]‐polyamides and [n]‐polyurethanes. Heating the poly(ester amide)s 6a–e yields the corresponding N ‐(hydroxyalkyl) imides 4a–e with no trace of cyclic ester amides. Theoretical calculations revealed that the cyclic ester amides 5a–e are clearly richer in energy than the isomeric N ‐(hydroxyalkyl) imides. These results show that cyclic ester amides can not be prepared from N ‐(hydroxyalkyl) imides by ring‐enlargement reactions. Copyright © 2003 Society of Chemical Industry