Synthesis of biodegradable polyurethanes chain-extended with (2S)-bis(2-hydroxypropyl) 2-aminopentane dioate


AKSOY E. A. , TAŞKOR G., GÜLTEKİNOĞLU M. , KARA F., ULUBAYRAM K.

JOURNAL OF APPLIED POLYMER SCIENCE, vol.135, no.5, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 135 Issue: 5
  • Publication Date: 2018
  • Doi Number: 10.1002/app.45764
  • Title of Journal : JOURNAL OF APPLIED POLYMER SCIENCE
  • Keywords: biocompatibility, degradation, polyurethanes, IN-VITRO DEGRADATION, SEGMENTED POLYURETHANES, BIOMEDICAL APPLICATIONS, MECHANICAL-PROPERTIES, HIGH-PERFORMANCE, URETERAL STENTS, ANTIBACTERIAL, ELASTOMERS, SCAFFOLDS, BRUSHES

Abstract

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, (2S)-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 C11H21NO6 (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 degrees C (PU) to -50 degrees 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. (C) 2017 Wiley Periodicals, Inc.