Terpene and dextran renewable resources for the synthesis of amphiphilic biopolymers

Marie-Hélène Alvès (1) , Jean-François Tranchant (2) , Emilie Gombart (2) , Gilles Sagorin (3) , Sylvain Caillol (4) , Laurent Billon (1) , Maud Save (5, 1)

1 IPREM - Institut pluridisciplinaire de recherche sur l'environnement et les matériaux
2 Parfums et Cosmétiques
3 DRT - Dax
4 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
5 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

The present work shows the synthesis of amphiphilic polymers based on the hydrophilic dextran and the hydrophobic terpenes as renewable resources. The first step concerns the synthesis of functional terpene molecules by thiol-ene addition chemistry involving amino- or carboxylic acid thiols and dihydromyrcenol terpene. The terpene modified polysaccharides were subsequently synthesized by coupling the functional terpenes with dextran. A reductive amination step produced terpene end-modified dextran with 94 % of functionalization while the esterification step produced three terpene grafted dextrans with a number of terpene units per dextran of 1, 5 and 10. The amphiphilic renewable grafted polymers were tested as emulsifiers for the stabilization of liquid miniemulsion of terpene droplets dispersed in an aqueous phase. The average hydrodynamic diameter of the stable droplets was observed at ca. 330 nm.

Keywords: renewable resources; polysaccharide; terpene; thiol-ene chemistry

Domains: Chemical Sciences; Polymers

Marie-Hélène Alvès, Jean-François Tranchant, Emilie Gombart, Gilles Sagorin, Sylvain Caillol, et al.. Terpene and dextran renewable resources for the synthesis of amphiphilic biopolymers. Biomacromolecules, 2014, 15, pp.242-251. ⟨10.1021/bm401521f⟩. ⟨hal-01097130⟩