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Issue 8, 2016
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Activated anionic ring-opening polymerization for the synthesis of reversibly cross-linkable poly(propylene oxide) based on furan/maleimide chemistry

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Abstract

The synthesis of cross-linkable random copolyethers of propylene oxide (PO) and furfuryl glycidyl ether (FGE) is first discussed. The anionic ring-opening polymerization and monomer activation methodology, based on the combination of tetraoctylammonium bromide and triisobutylaluminum, is used to perform the controlled synthesis of poly(propylene oxide-co-furfuryl glycidyl ether) copolymers with various compositions 95/5, 90/10, 75/25, 50/50, and 25/75 (PO/FGE mol%) and keeping the furfuryl moieties active. Copolymers with molar masses around 10 000 g mol−1 were obtained in short times. Subsequently, the furfuryl moieties were reacted with aromatic and aliphatic maleimide-based cross-linkers to perform Diels–Alder (DA) “click” reactions. Three-dimensional networks were obtained and their swelling ratio and insoluble fraction were determined. Glass transition temperature and retro-Diels–Alder (rDA) transition in the network were determined by differential scanning calorimetry analyses. Gel properties vary with the furan group amount in the initial copolymer and the cross-linker structure. The network disassembly at 110 °C was monitored by 1H NMR and quantitatively recorded by the re-appearance of the copolymer signals due to the rDA reaction. The solubility study showed that the gel was able to reform at 20 °C leading to reversible cross-linked polyethers.

Graphical abstract: Activated anionic ring-opening polymerization for the synthesis of reversibly cross-linkable poly(propylene oxide) based on furan/maleimide chemistry

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Publication details

The article was received on 04 Nov 2015, accepted on 18 Jan 2016 and first published on 19 Jan 2016


Article type: Paper
DOI: 10.1039/C5PY01778E
Polym. Chem., 2016,7, 1612-1622

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    Activated anionic ring-opening polymerization for the synthesis of reversibly cross-linkable poly(propylene oxide) based on furan/maleimide chemistry

    K. Roos, E. Dolci, S. Carlotti and S. Caillol, Polym. Chem., 2016, 7, 1612
    DOI: 10.1039/C5PY01778E

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