Skip to Main content Skip to Navigation
Journal articles

α,ω-Di(glycerol carbonate) telechelic polyesters and polyolefins as precursors to polyhydroxyurethanes: an isocyanate-free approach

Abstract : α,ω-Di(glycerol carbonate) telechelic poly(propylene glycol) (PPG), poly(ethylene glycol) (PEG), poly(ester ether) (PEE), and poly(butadiene) (PBD) have been synthesized through chemical modification of the corresponding α,ω-dihydroxy telechelic polymers (PPG-OH2, PEG-OH2, PEE-OH2 and PBD-OH2, respectively). Tosylation of the polymer diols with 4-tosylmethyl-1,3-dioxolan-2-one (GC-OTs) afforded, in high yields, the desired PPG, PEG, PEE and PBD end-capped at both termini with a five-membered ring cyclic glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one, GC). The GC-functionalization of the polymers at both chain-ends has been confirmed by NMR (1H, 13C, 1D and 2D) and FTIR spectroscopies. Using PPG-GC2 to demonstrate the concept, the corresponding polyhydroxyurethanes (PHUs/non-isocyanate polyurethanes (NIPUs)) have been subsequently prepared following a non-isocyanate method upon ring-opening catalyst-free polyaddition of the PPG-GC2 with JEFFAMINEs (Mn = 230-2000 g mol−1). The effect of various additives introduced during the polyaddition reaction has been studied at different temperatures. In particular, addition of LiBr (5 mol%) to the reaction medium was found to slightly promote the cyclocarbonate/amine reaction. The polymerization process was supported by FTIR and SEC analyses.
Document type :
Journal articles
Complete list of metadatas

Cited literature [13 references]  Display  Hide  Download

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01067261
Contributor : Muriel Cadieu <>
Submitted on : Tuesday, September 23, 2014 - 1:42:25 PM
Last modification on : Thursday, March 5, 2020 - 2:02:19 PM
Long-term archiving on: : Wednesday, December 24, 2014 - 8:54:05 PM

File

I_I_-Di_glycerol_carbonate_tel...
Files produced by the author(s)

Identifiers

Citation

Liana Annunziata, Abdou K. Diallo, Stéphane Fouquay, Guillaume Michaud, Frédéric Simon, et al.. α,ω-Di(glycerol carbonate) telechelic polyesters and polyolefins as precursors to polyhydroxyurethanes: an isocyanate-free approach. Green Chemistry, Royal Society of Chemistry, 2014, 16 (4), pp.1947-1956. ⟨10.1039/C3GC41821A⟩. ⟨hal-01067261⟩

Share

Metrics

Record views

350

Files downloads

843