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Synthesis of poly(ester amide)s composed of lactic acid and glycolic acid units by the bulk polycondensation of metal halide salts
Author(s) -
Murase Sara K.,
Puiggalí Jordi
Publication year - 2016
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.43197
Subject(s) - condensation polymer , glycolic acid , copolymer , polymer chemistry , polymerization , amide , chemistry , monomer , materials science , lactic acid , organic chemistry , polymer , biology , bacteria , genetics
Thermal polycondensation of the potassium salt of N ‐methylchloroacetyl‐6‐aminohexanoic acid (LAHK) was found to be effective in the preparation of a new poly(ester amide) based on lactic acid units with a high yield and a moderate molecular weight. The reaction started in the solid state and proceeded through the formation of potassium chloride salt as the driving force. The use of a monomer having an amide linkage diminished the secondary reactions previously found in the synthesis of polylactide from 2‐halogenopropionates. The polymerization of potassium salt of N ‐chloroacetyl‐6‐aminohexanoic acid (GAHK) took place in a similar temperature range as that of the 2‐chloropropionyl derivative; in this way, it was possible to conduct the copolymerization processes. The polymerization kinetics of LAHK and its mixture with GAHK was studied by Fourier transform infrared spectroscopy. The bulk polycondensation reaction was faster for GAHK than for LAHK, but the kinetic differences were not significant enough to prevent copolymerization at a temperature close to 160°C. Therefore, new degradable materials with tuned properties according to the glycolic acid/lactic acid content were obtained. 1 H‐NMR spectroscopy was useful for following the time evolution of the copolymerization process and for determining the final composition. Calorimetric data showed that all of the samples were thermally stable and that decreases in the melting temperature and enthalpy were observed at intermediate compositions. The existence of an eutectic point became proof that effective copolymerization was achieved in the thermal polycondensation process. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133 , 43197.