Synthesis and Biodegradation of Poly(l-lactide-co-β-propiolactone)

Abstract

Although the copolymerizations of l-lactide (LA) with seven- or six-membered ring lactones have been extensively studied, the copolymerizations of LA with four-membered ring lactones have scarcely been reported. In this work, we studied the copolymerization of LA with β-propiolactone (PL) and the properties of the obtained copolymers. The copolymerization of LA with PL was carried out using trifluoromethanesulfonic acid as a catalyst and methanol as an initiator to produce poly(LA-co-PL) with Mn of ~50,000 and PL-content of 6–67 mol %. The Tg values of the copolymers were rapidly lowered with increasing PL-contents. The Tm and ΔHm of the copolymers gradually decreased with increasing PL-contents, indicating their decreased crystallinity. Biodegradation test of the copolymers in compost demonstrated their improved biodegradability in comparison with the homopolymer of LA.

Metal Complexes in the Synthesis of Biodegradable Polymers: Achievements and Prospects

“…At present, it is used in industry as an initiator of the ring-opening polymerization of bis(2-ethylhexanoate)-tin (+2) [1,[6][7][8][9]. Other tin derivatives in the oxidation state (+2) have also been studied, but there are much fewer studies of this kind than there are works devoted to complexes based on other metals (Mg, Zn, Al) [10,11].…”

Assessing the Structural Heterogeneity of Isomeric Homo and Copolymers: an Approach Combining Ion Mobility Mass Spectrometry and Molecular Dynamics Simulations

“…Synthesis procedures are described in Supporting Information. 48 PEG samples used for IMS calibration were purchased from Sigma-Aldrich.…”

“…■ RESULTS AND DISCUSSION: PPL-B-PLA DIBLOCK COPOLYMERS Assessing the Sample Complexity by UPLC−ESI-MS. PPL-b-PLA diblock copolymers were prepared by successive ROP of β-propiolactone and lactide, as adapted from protocols developed by Nakayama et al 48 The methanol-initiated block thus corresponds to PPL, while the hydroxyl terminated moiety is PLA (Scheme 1). Two PPL-b-PLA samples with M n ∼ 1500 and 2100 g mol −1 were prepared.…”

Organocatalyzed ring-opening copolymerization of α-bromo-γ-butyrolactone with ε-caprolactone for the synthesis of functional aliphatic polyesters – pre-polymers for graft copolymerization

“…The organocatalyzed polymerization process could be more suitable to prepare biocompatible materials owing to its low toxicity. Organic Brønsted acids, e.g., sulfuric acid [14], carboxylic acid [15], trifluoromethanesulfonic acid (TfOH) [16,17], methanesulfonic acid (MSA) [18] and phosphoric acids [19] were found to be effective for the CROP of lactones. Although numerous investigations have been carried out, there still exist some shortcomings need to be overcome for the synthesis of aliphatic polyesters using organocatalysts.…”