RNA-Inspired and Accelerated Degradation of Polylactide in Seawater

Abstract

Marine plastic pollution is a worldwide challenge making advances in the field of biodegradable polymer materials necessary. Polylactide (PLA) is a promising biodegradable polymer used in various applications; however, it has a very slow seawater degradability. Herein, we present the first library of PLA derivatives with incorporated “breaking points” to vary the speed of degradation in artificial seawater from years to weeks. Inspired by the fast hydrolysis of ribonucleic acid (RNA) by intramolecular transesterification, we installed phosphoester breaking points with similar hydroxyethoxy side groups into the PLA backbone to accelerate chain scission. Sequence-controlled anionic ring-opening copolymerization of lactide and a cyclic phosphate allowed PLA to be prepared with controlled distances of the breaking points along the backbone. This general concept could be translated to other slowly degrading polymers and thereby be able to prevent additional marine pollution in the future.

Hydrophobic Biodegradable Hyperbranched Copolymers with Excellent Marine Diatom Resistance

“…53 The prepared OLLA has unit lengths of 20 on average in which the ester bonds are easily hydrolyzed to −OH and −COOH under alkaline conditions, enabling the copolymer to degrade faster. 54 This is further confirmed by the ATR-FTIR spectra of degradation products (Figure S9), the disappeared band at 1760 cm −1 (C�O), and the new band at 3150−3450 cm −1 (−COOH and −OH) in the spectrum of h-LLA 22 , while there are no obvious changes in the degradation products of PIBOA, indicating the fast hydrolysis of OLLA units in the h-LLA x copolymers. With the increase of −OH at the chain end of OLLA and the additional −OH supplied by the alkaline hydrolysis of ester groups of IBOA units, the hydrophilicity of h-LLA x copolymer-coated surface increases, resulting in an accelerated degradation process.…”

Synthesis and Biodegradability of Poly(ester-urethane)s via the Thiol-Michael Polyaddition of Dianhydro Sugar-Based Diacrylates

“…The urgent need to resolve microplastic-based pollution is prompting polymer chemists to synthesize new types of biodegradable polymer and plastic. − In particular, polymer designs based on carbohydrates including 1,4:3,6-dianhydrohexitol as the carbon resource are attracting interest from both industrial and academic fields, and 1,4:3,6-dianhydroglucitol (isosorbide (IS))-containing polycarbonate, poly­(ester-thioether), and furane-containing polyester have already been reported. − In pioneering research on the biodegradation of these IS-containing polymeric materials, polyesters containing IS and 1,4:3,6-dianhydromannitol isomannide (IM) showed excellent biodegradability even though they had relatively high glass-transition temperature ( T g ) values (between −10 and 75 °C). , Unfortunately, the polycarbonate did not show any biodegradation in the activated sludge. , Furthermore, while 1,4:3,6-dianhydrohexitol-based polymeric design has been recently studied, the biodegradation of 1,4:3,6-dianhydrohexitol-based polyurethanes has not been reported to the best of our knowledge.…”

RNA-inspired intramolecular transesterification accelerates the hydrolysis of polyethylene-like polyphosphoesters

“…Herein, we present an RNA-inspired degradation unit that was installed into an aliphatic polymer backbone and controls the backbone scission by an intramolecular transesterification similar to RNA-hydrolysis but also allows the functionalization of the polymers, similar to recent studies in polylactide. 6 The stability and degradation profiles of natural polymers are perfectly adjusted to their tasks. Deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) are polyphosphodiesters that are negatively charged at physiological pH.…”

“…Herein, we present an RNA-inspired degradation unit that was installed into an aliphatic polymer backbone and controlled the backbone scission by an intramolecular transesterification similar to RNA-hydrolysis, similar to recent studies in polylactide. 6 Further, the pendant hydroxyl groups allowed the functionalization of the polymers. 6 …”