Segmented poly(ether–ester–amide)s based on poly(l,l-lactide) macromers

Segmented poly(ether–ester–amide)s (PEEAs) were obtained from sebacoyl chloride (SEB), α,ω-hydroxyl terminated poly(l,l-lactide) (PLLA) or PLLA–PEG–PLLA macromers and the hydrophilic diamines 4,7,10-trioxa-1,13-tridecanediamine (1) and 3,6,9,12,15-pentoxa-1,17-heptadecanediamine (2) or diamide–diamines derived from 1 and 2 by inserting Gly-Phe or Gly-Val-Phe sequences. The molar ratio macromer/SEB/diamine was 1/2/1. The PEEAs were characterized by i.r. and 1H n.m.r spectroscopy and S.E.C. They are soluble in polar organic solvents and insoluble in water, but show equilibrium water absorptions up to 21.0% by wt. All PEEAs are semicrystalline, as shown by d.s.c. and WAXS techniques, with Tms ranging from 110 to 135°C. D.s.c. and d.m.t.a. showed a single Tg in the temperature range 31–53°C. Evidence of microphase separation was obtained only for aminoacids containing PEEAs by t.e.m.. Biocompatibily was assessed for selected polymers checking the viability and growth of Caco-2 cells on polymer films.