Issue 34, 2019

3D printable non-isocyanate polyurethanes with tunable material properties

Abstract

Green chemistry-based non-isocyanate polyurethanes (NIPU) are synthesized and 3D-printed via rapid, projection photopolymerization into compliant mechanisms of 3D structure with spatially-localized material properties. Trimethylolpropane allyl ether-cyclic carbonate is used to couple the unique properties of two types of reaction chemistry: (1) primary diamine-cyclic carbonate ring-opening conjugation for supplanting conventional isocyanate-polyol reactions in creating urethane groups, with the additional advantage of enabling modular segment interchangeability within the diurethane prepolymers; and (2) thiol–ene (click) conjugation for non-telechelic, low monodispersity, quasi-crystalline-capable, and alternating step-growth co-photopolymerization. Fourier transform infrared spectroscopy is used to monitor the functional group transformation in reactions, and to confirm these process-associated molecular products. The extent of how these processes utilize molecular tunability to affect material properties were investigated through measurement-based comparison of the various polymer compositions: frequency-related dynamic mechanical analysis, tension-related elastic-deformation mechanical analysis, and material swelling analysis. Stained murine myoblasts cultured on NIPU slabs were evaluated via fluorescent microscopy for “green-chemistry” affects on cytocompatibility and cell adhesion to assess potential biofouling resistance. 3D multi-material structures with micro-features were printed, thus demonstrating the capability to spatially pattern different NIPU materials in a controlled manner and build compliant mechanisms.

Graphical abstract: 3D printable non-isocyanate polyurethanes with tunable material properties

Supplementary files

Article information

Article type
Paper
Submitted
06 יול 2019
Accepted
16 יול 2019
First published
19 יול 2019

Polym. Chem., 2019,10, 4665-4674

Author version available

3D printable non-isocyanate polyurethanes with tunable material properties

J. J. Warner, P. Wang, W. M. Mellor, H. H. Hwang, J. H. Park, S. Pyo and S. Chen, Polym. Chem., 2019, 10, 4665 DOI: 10.1039/C9PY00999J

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