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Degradable Poly(ether-ester-urethane)s Based on Well-Defined Aliphatic Diurethane Diisocyanate with Excellent Shape Recovery Properties at Body Temperature for Biomedical Application

1
College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, China
2
Shandong Academy of Pharmaceutical Sciences, Shandong Provincial Key Laboratory of Biomedical Polymer, Jinan 250101, China
3
Success Bio-tech Co., Ltd., Jinan 250101, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Polymers 2019, 11(6), 1002; https://doi.org/10.3390/polym11061002
Received: 29 April 2019 / Revised: 28 May 2019 / Accepted: 3 June 2019 / Published: 5 June 2019
(This article belongs to the Special Issue Functional Polyurethanes – In Memory of Prof. József Karger-Kocsis)
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Abstract

The aim of this study is to offer a new class of degradable shape-memory poly(ether-ester-urethane)s (SMPEEUs) based on poly(ether-ester) (PECL) and well-defined aliphatic diurethane diisocyanate (HBH) for further biomedical application. The prepolymers of PECLs were synthesized through bulk ring-opening polymerization using ε-caprolactone as the monomer and poly(ethylene glycol) as the initiator. By chain extension of PECL with HBH, SMPEEUs with varying PEG content were prepared. The chemical structures of the prepolymers and products were characterized by GPC, 1H NMR, and FT-IR, and the effect of PEG content on the physicochemical properties (especially the shape recovery properties) of SMPEEUs was studied. The microsphase-separated structures of the SMPEEUs were demonstrated by DSC and XRD. The SMPEEU films exhibited good tensile properties with the strain at a break of 483%–956% and an ultimate stress of 23.1–9.0 MPa. Hydrolytic degradation in vitro studies indicated that the time of the SMPEEU films becoming fragments was 4–12 weeks and the introduction of PEG facilitates the degradation rate of the films. The shape memory properties studies found that SMPEEU films with a PEG content of 23.4 wt % displayed excellent recovery properties with a recovery ratio of 99.8% and a recovery time of 3.9 s at body temperature. In addition, the relative growth rates of the SMPEEU films were greater than 75% after incubation for 72 h, indicating good cytocompatibility in vitro. The SMPEEUs, which possess not only satisfactory tensile properties, degradability, nontoxic degradation products, and cytocompatibility, but also excellent shape recovery properties at body temperature, promised to be an excellent candidate for medical device applications. View Full-Text
Keywords: poly(ether-ester-urethane)s; poly(ethylene glycol); well-defined hard segments; degradability; shape memory behavior poly(ether-ester-urethane)s; poly(ethylene glycol); well-defined hard segments; degradability; shape memory behavior
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Xiao, M.; Zhang, N.; Zhuang, J.; Sun, Y.; Ren, F.; Zhang, W.; Hou, Z. Degradable Poly(ether-ester-urethane)s Based on Well-Defined Aliphatic Diurethane Diisocyanate with Excellent Shape Recovery Properties at Body Temperature for Biomedical Application. Polymers 2019, 11, 1002.

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