Chemical Science symposium 2023: Chemistry of polymers

Methods of polylactide copolymer synthesis by generating tetraphenylethane inifer groups in the PLA structure Mateusz Grabowski , Melania Bednarek, Bartłomiej Kost Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Poland One of the methods of modification of polylactide (PLA), a bio-derived polymer of increasing importance, is the introduction of other chemical structures into the PLA chain. This can be achieved in different ways, one of which is copolymerization. Block copolymers can be synthesized by various methods nevertheless each of the methods used thus far have certain limitations, so new methods are being sought and developed to replace or simplify existing ones. In this work, we present the synthesis of copolymers of polylactide and selected poly(vinyl monomers) (PVM) using tetraphenylethane (TPE) “inifer” groups. TPE groups were generated in PLA-based polymer via different approaches, the starting point of which was the appropriate functionalization of 4-hydroxybenzophenone (HBP). Coupling of HBP moieties (present in low molecular weight HBP derivative or in PLA chain) under UV irradiation generated TPE groups which were able to dissociate forming radicals under moderate heating and consequently, initiate polymerization of the vinyl monomer according to Figure 1. By applying developed by us approaches, the following PLA-based copolymers could be obtained: 1. Triblock PLA-PVM-PLA copolymer: By the initiation of lactide polymerization with HBP derivative and next coupling. 2. Multiblock ...PLA-PVM-PLA-PVM…copolymer: By the synthesis of TPE containing diol, next coupled with PLA diol using diisocyanate. 3. PLA-based network containing reversible TPE groups with the possibility of introducing PVM sequences: By copolymerization of lactide with an epoxy compound containing HBP group and next coupling.

Fig 1. Synthesis of block copolymers PLA-PVM-PLA using TPE inifer. Acknowledgement: The study was performed within Grant NCN 2018/31/B/ST8/01969. References 1. M. Grabowski, B. Kost, P. Kubisa, M. Bednarek, Polymers, 14 (2022), 1529. 2. Grabowski M.; Kost B.; Bodzioch A.; Bednarek M. Int. J. Mol. Sci. (2023), 24, 19.

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