Fully Isohexide-Based Polyesters: Synthesis, Characterization, and Structure-Properties Relations

Jing Wu; Pieter Eduard; Lidia Jasińska-Walc; Artur Różański; Bart A. J. Noordover; Daan S. Van Es; Cor E. Koning

Fully Isohexide-Based Polyesters: Synthesis, Characterization, and Structure-Properties Relations

Abstract

Here we present a novel series of biobasedpolyesters solely based on renewable isohexide building blocks,synthesized via melt polymerization. The recently developedisoidide dicarboxylic acid (IIDCA) was polymerized with rigidrenewable diols such as isosorbide (IS), isomannide (IM),isoidide (II), and the novel 2,5-methylene-extended isoididedimethanol (IIDML). Both IIDCA and IIDML weredeveloped to increase the reactivity of the isohexide buildingblock, while retaining rigidity and hence the beneficial effectson Tg. Compared to the parent isohexides, IIDML showed amarkedly higher reactivity, resulting in three to four timeshigher weight-average molecular weight (Mw) values of thesynthesized polyesters. The molecular structure of the novel polyesters was analyzed by 1H, 13C and 2D-COSY NMR techniques,confirming that the stereoconfigurations of the isohexide moieties were preserved under the applied polymerization conditions.The II/IS-based polyesters have high Tg values noted of 70 and 85 °C, respectively, while the IIDML-based polyester has a lowerTg of approximately 45 °C, yet with an higher degree of crystallinity than the parent isohexide-based polyesters. A systematicstudy on structure-thermal properties relations comparing these novel polyesters with, e.g., aliphatic polyesters reveals that, whenincorporated into polyesters, both IIDCA and IIDML are able to increase the Tg by approximately 70 °C, which is comparable tothe parent isohexides. Given the enhanced reactivity, high thermal stability and the retained ability to increase the Tg, IIDML is apromising renewable building block for performance polymers.

Authors (7)

Jing Wu
- Wageningen University and Research Center .
Pieter Eduard
- Wageningen University and Research Center .
Lidia Jasińska-Walc dr hab. inż.
Artur Różański
- PAN Centre of Molecular and Macromolecular Studies
Bart A. J. Noordover
- Eindhoven University of Technology .
Daan S. Van Es
- Wageningen University and Research Center .
Cor E. Koning
- Eindhoven University of Technology .

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Category:: Articles
Type:: artykuł w czasopiśmie wyróżnionym w JCR
Published in:: MACROMOLECULES no. 46, edition 2, pages 384 - 394,
ISSN: 0024-9297
Language:: English
Publication year:: 2013
Bibliographic description:: Wu J., Eduard P., Jasińska-Walc L., Różański A., Noordover B., Van Es D., Koning C.: Fully Isohexide-Based Polyesters: Synthesis, Characterization, and Structure-Properties Relations// MACROMOLECULES. -Vol. 46, iss. 2 (2013), s.384-394
Verified by:: Gdańsk University of Technology