Stereoisomeric effects in thermo-remendable polymer networks based on diels-alder crosslink reactions

J. Canadell Ayats, H.R. Fischer, G. With, de, R.A.T.M. Benthem, van

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Abstract

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 1H 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.
Original languageEnglish
Pages (from-to)3456-3467
Number of pages12
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume48
Issue number15
DOIs
Publication statusPublished - 2010

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Polymers
Maleimides
Stereoisomerism
Isomerization
Nuclear magnetic resonance spectroscopy
Differential scanning calorimetry
Hot Temperature
Temperature
furan
maleimide

Cite this

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title = "Stereoisomeric effects in thermo-remendable polymer networks based on diels-alder crosslink reactions",
abstract = "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 1H 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.",
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Stereoisomeric effects in thermo-remendable polymer networks based on diels-alder crosslink reactions. / Canadell Ayats, J.; Fischer, H.R.; With, de, G.; Benthem, van, R.A.T.M.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 48, No. 15, 2010, p. 3456-3467.

Research output: Contribution to journalArticleAcademicpeer-review

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AU - Canadell Ayats, J.

AU - Fischer, H.R.

AU - With, de, G.

AU - Benthem, van, R.A.T.M.

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AB - 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 1H 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.

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