Synthesis of functionalizable and biodegradable polymers via ring‐opening polymerization of 5‐benzyloxy‐trimethylene carbonate and ε‐caprolactone

Abstract

The biomedical applications of poly(e-caprolactone) (PCL) were limited for its high hydrophobicity and crystallinity. In this study, we copolymerized CL with amorphous 5-hydroxyl-trimethylene carbonate (HTMC) to solve the problem. The 5-benzyloxy-trimethylene carbonate (BTMC) was synthesized to copolymerize with CL, then hydrogenolyzed to obtain hydroxyl pendant groups. A serial of copolymers with different BTMC molar ratio were synthesized and their chemical structures and thermal properties were thoroughly studied with NMR, FT-IR, GPC, XRD, DSC, and TGA. Finally we examined the water contact angle of the copolymers. DSC and XRD results showed that the PCL segments in the copolymers crystallized below 16.8%. BTMC molar content and the crystallinity of the copolymers increased after hydrolysis. With the introduced hydroxyl pendant groups, the deprotected copolymers improved their hydrophilic property significantly, and the copolymer with 9.3% HTMC molar content had static water contact angle as low as 36.5 .

Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies

“…This family of compounds was synthesized for polymer applications. − They are also intermediates to prepare molecules of biological interest. − …”

Synthesis, characterization and reactivity of a six-membered cyclic glycerol carbonate bearing a free hydroxyl group

“…The deprotection of the diols and their conversion into cyclic carbonates yield the desired monomers. [9][10][11] When molecules containing two 1,3-diol moieties are used six-membered bis(cyclic carbonates) can be obtained. 12,13 However, it is possible to convert into a cyclic carbonate only one of the 1,3-diol moieties leaving the other for further modification.…”