Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polyme
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ARTICLE
POLYMER SCIENCE
https://doi.org/10.1007/s10118-020-2415-9 Chinese J. Polym. Sci.
Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing Na Zhao†, Xin-Xin Cao†, Jin-Feng Shi, and Zhi-Bo Li* Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department, College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Electronic Supplementary Information Abstract Development of degradable polyester elastomers plays an important role in the applications of soft mateirals. Noncrystalline polymenthides (PMs) from menthol derived lactone monomers are excellent soft segments for preparing degradable polyester elastomers. By using cyclic trimeric phosphazene base (CTPB) as an organocatalyst, we successfully synthesized PMs with different molecular weights (8.2 kDa to 100.7 kDa) in high yields via ring-opening polymerization (ROP) of menthide. When a CTPB/urea binary catalytic system was adopted, the polymerizations proceeded in a more controlled manner. Using glycerol as initiator, star shaped PMs with well-defined structure were synthesized and subsequently end-capped by acrylate. UV irradiation of the terminal acrylate groups in the star-shaped PMs resulted in formation of chemically cross-linked polyester elastomers without heat or other stimuli. The obtained polyester elastomers exhibit matched modulus (3.8−5.5 MPa), tensile strength (0.56−0.68 MPa), and strain at break (280%−320%) with soft body tissues, displaying great potential in biomedical applications. Keywords Polyester elastomer; Cyclic trimeric phosphazene base; Ring-opening polymerization; Menthide, Biobased polyester Citation: Zhao, N.; Cao, X. X.; Shi, J. F.; Li, Z. B. Preparation of degradable polymenthide and its elastomers from biobased menthide via organocatalyzed ring-opening polymerization and UV curing. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-020-2415-9
INTRODUCTION In recent years, degradable polymeric materials from renewable biomass have gained considerable attention in materials science.[1−4] They could reduce our dependence on fossil fuels and mitigate the adverse environmental effects of white pollution. Various renewable biomass, including terpenes, fatty acids, plant oils, etc., has been widely explored in designing elastomers.[5−7] Among the bio-based elastomers that may be considered, biodegradable polyester elastomers have undergone fast growth in recent years for their good biocompatibility and mechanical properties in tissue engineering and other biomedical applications.[8−10] Polyesters are innately biologically degradable due to the ester bonds subject to hydrolysis and/or enzymatic catalyzed degradation in vivo, which is crucial for their applications in tissue engineering.[8,10] Polyester elastomers are polyesters that have an elastic region over a large strain or have the ability to recover its initial
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