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Issue 22, 2017
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A thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization

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Abstract

The present work is dedicated to the design of novel sulfur-substituted cyclic carbonates from thioglycerol, fatty acids and sugar derivatives. In this methodology, a sulfur atom is inserted in the β position of 5-membered ring cyclic carbonates via a two-step synthesis including the thiol–ene coupling of thioglycerol on fatty acid derivatives, followed by a transcarbonation. A similar strategy was adopted to prepare glycolipid-based cyclic carbonates in order to bring biodegradability to the final poly(hydroxyurethane)s. The so-formed monomers were characterized by NMR spectroscopies, HPLC and DSC. The enhanced reactivity of sulfur-substituted cyclic carbonates was demonstrated through a 1H NMR spectroscopy kinetic study of a model reaction with hexylamine. Fatty acid- and glycolipid-based sulfur-substituted bis-cyclic carbonates were then polymerized with diamines in a solvent using a catalyst-free process. FTIR, NMR, SEC, DSC and TGA were performed to investigate the PHUs’ chemical structure, molar masses and thermal properties. Finally, the so-formed PHUs were post-functionalized by sulfonation with m-CPBA taking advantage of thioether functions. The impact of the chemical modification was mostly studied on the polymer solubility and thermal stability.

Graphical abstract: A thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization

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Publication details

The article was received on 02 Apr 2017, accepted on 01 May 2017 and first published on 01 May 2017


Article type: Paper
DOI: 10.1039/C7PY00556C
Citation: Polym. Chem., 2017,8, 3438-3447
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    A thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization

    O. Lamarzelle, G. Hibert, S. Lecommandoux, E. Grau and H. Cramail, Polym. Chem., 2017, 8, 3438
    DOI: 10.1039/C7PY00556C

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