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Issue 17, 2018
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Degradable high Tg sugar-derived polycarbonates from isosorbide and dihydroxyacetone

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Abstract

Polycarbonates from isosorbide and dihydroxyacetone (DHA) have been synthesised using organocatalytic step-growth polymerization of their corresponding diols and bis-carbonylimidazolide monomers. By the choice of the feed ratio and monomer activation, either isosorbide or ketal protected DHA, random and alternating poly(Iso-co-DHA) carbonates have been formed. Thermal properties by DSC and TGA were herein strongly correlated to the monomer composition. Dilution studies using 1H-NMR spectroscopy of a model compound DHA-diethyl carbonate in CD3CN and D2O highlighted the influence of α-substituents on the keto/hydrate equilibrium of DHA. Further kinetics studies in the pH* range of 4.7 to 9.6 serve to show the hydrolytic pH-profile of DHA-carbonates. The hydrolytic degradation of deprotected polymer pellets shows an increased degradation with increasing DHA content. Pellets with a random or alternating configuration show different characteristics in terms of mass loss and molecular weight loss profile over time.

Graphical abstract: Degradable high Tg sugar-derived polycarbonates from isosorbide and dihydroxyacetone

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Publication details

The article was received on 12 Feb 2018, accepted on 12 Mar 2018 and first published on 14 Mar 2018


Article type: Paper
DOI: 10.1039/C8PY00256H
Citation: Polym. Chem., 2018,9, 2238-2246
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    Degradable high Tg sugar-derived polycarbonates from isosorbide and dihydroxyacetone

    D. Hult, S. García-Gallego, T. Ingverud, O. C. J. Andrén and M. Malkoch, Polym. Chem., 2018, 9, 2238
    DOI: 10.1039/C8PY00256H

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