Stereoisomeric effects in thermo-remendable polymer networks based on diels-alder crosslink reactions
article
This study describes the synthesis, the spectroscopic, and the thermal characterization of linear and crosslinked polymers as well as a number of corresponding model compounds, containing Diels-Alder adducts derived from furan and maleimide groups. The thermal reversibility (rDA, DA) of structurally varied model compounds, polymeric and network structures were studied by differential scanning calorimetry, where possible in combination with <sup>1</sup>H NMR spectroscopy. It was established that the endo and exo DA stereoisomers show significantly different thermal responses: the rDA of the endo DA-adducts typically takes place at 20-40 K lower temperatures than that of the corresponding exo DA-adducts in all cases, with the exception of some aromatic maleimides. Although In situ isomerization was observed to a limited extent and only In some cases, this effect is not expected to influence the thermoremendability of DA-crosslinked networks being dependent on two separate stereoisomeric rDA steps.
Topics
Diels-Alder cycloadditionDiels-Alder polymersDifferential scanning calorimetryFuransMaleimidesStereoisomersThermoremendableCross-link reactionsCross-linked networksCross-linked polymersDiels-Alder AdductsH NMR spectroscopyModel compoundNetwork structuresPolymer networksThermal characterizationThermal responseThermal reversibilityCalorimetersIsomersNuclear magnetic resonance spectroscopyStereochemistry
TNO Identifier
408451
ISSN
0887624X
Source
Journal of Polymer Science, Pt.A: Polymer Chemistry, 48(15), pp. 3456-3467.
Pages
3456-3467
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