Divinylglycol, a Glycerol-Based Monomer: Valorization, Properties, and Applications

TL;DR

This paper explores the polymerization potential of divinylglycol, a glycerol derivative, demonstrating its reactivity and versatility in creating new bio-based polymers through various polymerization methods.

Contribution

It introduces divinylglycol as a novel bio-sourced monomer and investigates its polymerization behavior, expanding options for glycerol-based bio-refinery valorization.

Findings

DVG double bonds are more reactive than hydroxyl groups.

Successful synthesis of diverse polymers from DVG.

DVG can form epoxy-amine networks via oxidation.

Abstract

In the context of the development of bio-refineries, glycerol and its derivatives are co-products of the oleochemistry for which new valorization routes must be found. In this study, the polymerizability of divinylglycol (DVG), a symmetrical C-6 glycerol derivative which bears a vicinal diol and two vinyl functions was studied. The reactivity of the hydroxyl and vinyl functions of DVG through polycondensation and polyaddition reactions was investigated. In a first step, the synthesis of polyesters was carried out by reaction of DVG with various biosourced diesters. In a second route, DVG was polymerized through its vinyl functions by ADMET and thiol-ene addition. Finally, three-dimensional epoxy-amine networks were prepared from a series of diamines and bis-epoxidized DVG, the latter being prepared by oxidation of the DVG double bonds. These different polymerization reactions showed that DVG double bonds were more reactive than the alcohol ones and that a panel of original polymers could be obtained from this bio-sourced synthon.