New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide, and Isoidide

Asma Saadaoui; Raouf Medimagh; Sylvain Marque; Damien Prim; Saber Chatti; Herve Casabianca; Mongia Said Zina

doi:10.1080/15685551.2016.1239175

New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide, and Isoidide

Des Monomers Polym. 2016 Oct 23;20(1):221-233. doi: 10.1080/15685551.2016.1239175. eCollection 2017.

Authors

Asma Saadaoui^{1

2

3}, Raouf Medimagh¹, Sylvain Marque⁴, Damien Prim⁴, Saber Chatti³, Herve Casabianca³, Mongia Said Zina²

Affiliations

¹ Laboratoire des Substances Naturelles (LR10INRAP02), Institut National de Recherche et d'Analyse Physico-chimique (INRAP), Ariana, Tunisia.
² Faculté des Sciences de, Université de Tunis El Manar, Tunis, Tunisia.
³ Institut des Sciences Analytiques, UMR5280, CNRS, Université de Lyon 1, ENS-Lyon, Villeurbanne, France.
⁴ Institut Lavoisier de Versailles (ILV) UMR CNRS 8180, Université de Versailles-St-Quentin (UVSQ), Versailles Cedex, France.

Abstract

In the present work, we propose the synthesis of a new family of sugar derived 1,4:3,6-dianhydrohexitol based AA/AB-type monomers. Unprecedented diacids based on Isomannide and Isoidide were elaborated with high yields and showed interestingly high melting point ranges (240-375 °C). Optimization of reaction conditions (temperature, time of reaction, and reactant ratios) has been investigated to synthesize the key intermediate of a set of AB monomers with acid, ester, and acid chloride functionalities. Isosorbide based ether benzoic acid AB monomer was polymerized and characterized by NMR and DSC techniques. The results show a semicrystalline behavior of the obtained polymer thanks to the controlled stereoregular arrangement of the AB starting monomer.

Keywords: 1,4:3,6-Dianhydrohexitols; AB monomers; Isosorbide; biosourced; poly(ether)esters; semicrystalline.