Degradable poly(alkyl acrylates) with uniform insertion of ester bonds, comparing batch and semibatch copolymerizations

Degradable poly(alkyl acrylates) with uniform insertion of ester bonds, comparing batch and semibatch copolymerizations

Macromolecules

10.1021/acs.macromol.0c00207

https://doi.org/10.1021/acs.macromol.0c00207

Jean-Baptiste Lena, Alexander W. Jackson, Lohitha Rao Chennamaneni, Chiong Teck Wong, Freda Lim, Yosephine Andriani, Praveen Thoniyot, Alexander M. van Herk

12 May 2020

Lena, J.-B.; Jackson, A. W.; Chennamaneni, L. R.; Wong, C. T.; Lim, F.; Andriani, Y.; Thoniyot, P.; Herk, A. M. V., Degradable poly(alkyl acrylates) with uniform insertion of ester bonds, comparing batch and semibatch copolymerizations. Macromolecules 2020, DOI: 10.1021/acs.macromol.0c00207.

Poly(alkyl)acrylates are a major class of nonbiodegradable polymers which are difficult to recycle due to an all-carbon backbone. Introducing a certain number of ester bonds in the backbone via radical ring opening copolymerization of acrylates with 2-methylene-1,3 dioxepane (MDO) improves its degradability and may be promising for chemical recycling. The current work examines the influence of monomer addition profiles on the copolymerization of acrylates with MDO. We improved the homogeneity of the MDO insertion through a semibatch approach, which was demonstrated by the molecular weight distribution of fragments after alkali degradation. By detailed NMR analysis, we identified the incorporation of MDO ring retained units, formation of branches on acrylate units, and formation of branches on MDO ring open units as the key side reactions. Theoretical calculations showed that mainly kinetic factors influence the outcome of the polymerization.

PublisherCopyrights

This work was supported by the Industry Alignment Fund - Pre-Positioning Programme (IAF-PP) of Agency for Science, Technology and Research (A*STAR) (A1786a0030).

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Macromolecules, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.macromol.0c00207.

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