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Synthesis of biodegradable polyurethanes chain‐extended with (2 S )‐bis(2‐hydroxypropyl) 2‐aminopentane dioate
Author(s) -
Aksoy Eda Ayse,
Taskor Gulce,
Gultekinoglu Merve,
Kara Filiz,
Ulubayram Kezban
Publication year - 2018
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.45764
Subject(s) - materials science , polycaprolactone , polymer , hexamethylene diisocyanate , polymer chemistry , radius of gyration , biodegradation , biocompatibility , polyester , diol , fourier transform infrared spectroscopy , chemical engineering , organic chemistry , polyurethane , chemistry , composite material , engineering , metallurgy
Polyurethanes (PUs) are the most widely used polymers because of their biocompatibility, tunable mechanical properties, and chemical versatility. In this study, a two‐step condensation polymerization of polycaprolactone diol and hexamethylene diisocyanate was carried out, and a glutamic acid ester derivative, (2 S )‐bis(2‐hydroxypropyl) 2‐aminopentane dioate (HPAP), was used as a new chain extender to accelerate the biodegradation properties of PU. HPAP was synthesized by the Fischer esterification of l ‐glutamic acid. The chemical structure of HPAP was confirmed by high‐resolution mass spectroscopy and m/z (EI) was found to be 264.1447 [calculated value = 264.1443 for C 11 H 21 NO 6 (M + )]. The Berry plot of static light‐scattering measurements showed that PU–HPAP had a weight‐average molecular weight and radius of gyration of 33,100 g/mol and 1420 nm, respectively. The presence of HPAP in the PU structure facilitated hydrogen bonding between the polymer chains and increased the glass‐transition temperature from −56 °C (PU) to −50 °C (PU–HPAP). PU–HPAP showed the highest hydrophilicity and surface free energy among all of samples, and this accelerated the in vitro biodegradation period via surface erosion. In addition, PU–HPAP did not show any cytotoxic effects on the L929 cells. A new biodegradable and biocompatible PU–HPAP was obtained as candidate for tissue engineering applications. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135 , 45764.