Ethyl Ester Diisocyanate Research Articles

Synthesis, Degradation, and Cytotoxicity of Multiblock Poly(ε-caprolactone urethane)s Containing Gemini Quaternary Ammonium Cationic Groups

Novel cationic biodegradable multiblock poly(epsilon-caprolactone urethane)s that contain gemini quaternary ammonium side groups on the hard segments were developed. To obtain these polyurethanes, a new L-lysine-derivatized diamine containing gemini quaternary ammonium side groups (GA8) was first synthesized and characterized by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectra (NMR), mass spectrometry (MS), and high-resolution mass spectra (HRMS). Then a series of gemini poly(epsilon-caprolactone urethane)s were designed and prepared using L-lysine ethyl ester diisocyanate (LDI), poly(epsilon-caprolactone) (PCL) diols, 1,4-butandiol (BDO), and GA8 and were terminated by methoxyl-poly(ethylene glycol) (m-PEG). The obtained polyurethanes were fully characterized by (1)H NMR, gel permeation chromatograph (GPC), differential scanning calorimetry (DSC), FTIR, and water contact angle (WCA) measurement. The gemini polyurethane shows a rapid rate of hydrolytic and enzymatic degradation, as demonstrated by weight loss and polarizing light microscopy (PLM) observations. In vitro cytotoxicity analysis suggests that both the polyurethanes and their degradation products do not show significant inhibition effect against fibroblasts. Our work provides a new way to synthesize nontoxic and amphiphilic multiblock polyurethanes with rapid degradation rate, and these new materials could be good candidates as biodegradable carriers for drug and gene delivery.

Synthesis and characterization of biodegradable polyurethane based on poly(ε-caprolactone) and L-lysine ethyl ester diisocyanate

A biocompatible diisocyanate, lysine ethyl ester diisocyanate, was prepared. Afterwards, biodegradable polyurethane (PU) was synthesized by the stepgrowth polymerization of this diisocyanate with hydroxyl terminated poly(e-caprolactone) in the presence of 1,4-butanediol as a chain-extender. The resulting PU was characterized by GPC, IR and DSC measurements. Its mechanical strength was found to increase with increasing the hard segment content. The PU microfiber meshes with high porosity were obtained by solution electrospinning technique. Their degradation behavior in the PBS and enzymatic solution was also investigated.

Biofunctional rapid prototyping for tissue‐engineering applications: 3D bioplotting versus 3D printing

AbstractTwo important rapid‐prototyping technologies (3D Printing and 3D Bioplotting) were compared with respect to the computer‐aided design and free‐form fabrication of biodegradable polyurethane scaffolds meeting the demands of tissue‐engineering applications. Aliphatic polyurethanes were based on lysine ethyl ester diisocyanate and isophorone diisocyanate. Layer‐by‐layer construction of the scaffolds was performed by 3D Printing, that is, bonding together starch particles followed by infiltration and partial crosslinking of starch with lysine ethyl ester diisocyanate. Alternatively, the 3D Bioplotting process permitted three‐dimensional dispensing and reactive processing of oligoetherurethanes derived from isophorone diisocyanate, oligoethylene oxide, and glycerol. The scaffolds were characterized with X‐ray microtomography, scanning electron microscopy, and mechanical testing. Osteoblast‐like cells were seeded on such scaffolds to demonstrate their potential in tissue engineering. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 624–638, 2004