Non-Isocyanate Polythiourethanes (NIPTUs) from Cyclodithiocarbonate Telechelic Polyethers

Abstract : Commercially available poly(propylene glycol) (PPG) and poly(tetrahydrofuran diglycidyl ether) (PTG) alpha,omega-end-capped with epoxide functions have been chemically modified into alpha,omega-bis(cyclodithiocarbonate) (DTC) telechelic analogues. The neat stoichiometric reaction of PPG/PTG-Epoxide(2) with CS2 and LiBr enabled to prepare up to 300 g of the corresponding PPG/PTG-DTC2 functional polyethers. The subsequent one-pot, one-step aminolysis of the cyclodithiocarbonate end-groups of the polyethers using di- or polyamines, namely triethylene glycol diamine (Jeffamine EDR-148) and/or polyethylenimine (Lupasol), smoothly afforded the poly(mercaptothiourethane)/polyethers, as non-isocyanate polythiourethanes (NIPTUs) featuring pendant primary thiol groups. Ultimate cross-linking of the NIPTUs upon oxidation with MnO2 or through the Michael reaction of the pendant thiol functions with di- or triacrylates, afforded cured NIPTU materials. Detailed macromolecular and thermomechanical characterizations of the (cross-linked) polymer materials, including NMR, FTIR, and Raman spectroscopies, MALDI-ToF mass spectrometry, DSC analyses, and tensile and rheology tests, are reported.
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Submitted on : Wednesday, September 4, 2019 - 1:18:36 PM
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Elise Vanbiervliet, Stephane Fouquay, Guillaume Michaud, Frederic Simon, Jean-Francois Carpentier, et al.. Non-Isocyanate Polythiourethanes (NIPTUs) from Cyclodithiocarbonate Telechelic Polyethers. Macromolecules, American Chemical Society, 2019, 52 (15), pp.5838-5849. ⟨10.1021/acs.macromol.9b00695⟩. ⟨hal-02278419⟩



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