Degradable high Tg sugar-derived polycarbonates from isosorbide and dihydroxyacetone

Authors
García Gallego, SandraUniversity of Alcalá Author; Hult, Daniel; Ingverud, Tobias; Andrén, Oliver C. J.; Malkoch, Michael
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/35559
DOI: 10.1039/C8PY00256H
ISSN: 1759-9954
Date
2018-03-12
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Bibliographic citation
Polymer chemistry, 2018, v.9, n.17, p. 2238-2246
Keywords
Polycarbonates
isosorbide
dihydroxyacetone
step-growth polymerization
imidazol
Project
info:eu-repo/grantAgreement/Swedish Research Council/VR/2011-5358/2010-435/2015-04779/Knut and Alice Wallenberg Foundation/KAW/2012-0196/H2020/Marie Sklodowska-Curie/655649.
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© Royal Society of Chemistry, 2018
Access rights
info:eu-repo/semantics/openAccess
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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 alfa-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.
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