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

Asma Saadaoui (1, 2, 3) , Raouf Medimagh (1) , Sylvain Marque (4) , Damien Prim (4) , Saber Chatti (2) , Hervé Casabianca (2) , Mongia Said Zina (3)

1 LR02INRAP10 - Laboratoire des Substances Naturelles
2 ISA-PNBS - Produits naturels et biosourcés - Natural & Bio-based Products
3 FST - Faculté des Sciences Mathématiques, Physiques et Naturelles de Tunis
4 ILV - Institut Lavoisier de Versailles

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 degrees 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.

Mots clés: 1-4:3-6-Dianhydrohexitols; Isosorbide; biosourced; AB monomers; semicrystalline; poly(ether)esters

Domaines: Polymères

Asma Saadaoui, Raouf Medimagh, Sylvain Marque, Damien Prim, Saber Chatti, et al.. New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide, and Isoidide. Designed Monomers and Polymers, 2017, 20 (1), pp.221-233. ⟨10.1080/15685551.2016.1239175⟩. ⟨hal-01519089⟩