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 1 H 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 T m s ranging from 110 to 135°C. D.s.c. and d.m.t.a. showed a single T g 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.