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

Abstract

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.

Tough and biodegradable polyurethane-silica hybrids with a rapid sol-gel transition for bone repair

“…Polyurethane and hybrid confirmations Similar to previous studies 9,10 , PCL with two terminated hydroxyl groups at opposite ends, namely, PCL-diol, was used as the polyol to synthesize biodegradable PU. The diol groups were reacted with HDI, a diisocyanate, to produce urethane bonds between the PCL-diols and polyurethane 12,13 .…”

“…The developed PU was thermoplastic and biodegradable as a result of polymerization with polycaprolactone (PCL)-diol, hexamethylene diisocyanate (HDI), and (3-aminopropyl) triethoxysilane (APTES). PCL-diol and aliphatic HDI have been used to synthesize thermoplastic, biodegradable, and biocompatible PUs 9,10 . A thermoplastic polymer was required for the sol-gel process since polymers must exist in a sol state before forming covalent bonds with the silica network.…”

Tough and biodegradable polyurethane-silica hybrids with rapid sol-gel transition for bone repair

“…Similar to previous studies 9,10 , PCL with two terminated hydroxyl groups at opposite ends, namely PCLdiol, was used as the polyol to synthesize biodegradable PU. The diol groups were reacted with HDI, a diisocyanate, to produce urethane bonds between the PCL-diols and polyurethane 11,12 .…”

“…The developed PU was thermoplastic and biodegradable as a result of polymerization with polycaprolactone(PCL)-diol, hexamethylene diisocyanate (HDI), and (3-aminopropyl)triethoxysilane (APTES). PCL-diol and aliphatic HDI have been used to synthesize a thermoplastic, biodegradable, and biocompatible PU 9,10 . The introduction of (3-aminopropyl)triethoxysilane (APTES) during polymerization allowed for the functionalization of the PU with alkoxysilane groups, which enabled covalent bonding to the silica network.…”

The Current Status, Prospects, and Challenges of Shape Memory Polymers Application in Bone Tissue Engineering

“…Shape memory properties mainly include biocompatibility, biodegradation, and mechanical properties [ 41 ]. Many studies have shown that PCL has certain biocompatibility and degradability [ 23 , 42 ], in which the porous structure makes a specific contribution because appropriate pore size is conducive to the invasion and growth of cells and tissues into the scaffold, and finally, the completion of regeneration and repair. The size of molten salt or sugar particles directly determines the pore size of the porous structure in SMPs.…”