Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization

A series of non-toxic biodegradable and biocompatible polyurethanes bearing p-aminobenzoate moieties are presented. The introduction of this attractive motif was carried out by the synthesis of a novel isocyanate. These biodegradable polymers were chemically and physically characterized by several techniques and methods including bioassay and water uptake measurements. The molecular weight of the soft segment (poly-ε-caprolactone, PCL) and hard segment crystallinity dictated the mechanical behavior and water uptake. The behavior of short PCL-based polyurethanes was elastomeric, whilst increasing the molecular weight of the soft segment led to plastic polyurethanes. Water uptake was hindered for long PCL due to the crystallization of the soft segment within the polyurethane matrix. Furthermore, two different types of chain extender, hydrolyzable and non-hydrolyzable, were also evaluated: polyurethanes based on hydrolyzable chain extenders reached higher molecular weights, thus leading to a better performance than their unhydrolyzable counterparts. The good cell adhesion and cytotoxicity results demonstrated the cell viability of human osteoblasts on the surfaces of these non-toxic biodegradable polyurethanes.

Alejandra Rubio Hernández-Sampelayo, Rodrigo Navarro, Dulce María González García1,2, Luis García-Fernández3, Rosa Ana Ramírez-Jiménez3, María Rosa Aguilar3 and Ángel Marcos-Fernández.

1 Instituto Politécnico Nacional, Escuela Superior de Ingeniería Química e Industrias Extractivas, UPALM-Zacatenco, Col Lindavista, Mexico City 07738, Mexico

2 Universidad de Guanajuato, Departamento de Química, Noria Alta s/n, Guanajuato 36050, Mexico

3 Biomedical Research Networking Center in the Subject Area of Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Avenida Monforte de Lemos 3–5, 28029 Madrid, Spain