Isosorbide and Tricyclodecanedimethanol for the Synthesis of Amorphous and High T_g Partially Biobased Copolyesters

Abstract

The synthesis and properties of amorphous poly-(tricyclodecanedimethylene-co-isosorbide terephthalate) (PTIT) with the isosorbide (IS) content ranging from 0 to 68 mol % relative to the total diol amount were investigated. Surprisingly, it was found that isosorbide enhanced the polycondensation kinetics and acted as a temporary chain linker. Polymerization kinetics improvement maximum was observed when the isosorbide content was around 9 mol %. It was also found that higher molar masses were achieved when the isosorbide molar content was increased (number-average molar mass, M n , around 16,000 g mol −1 ). The glass transition temperature linearly increased of 0.7 °C per mol% of isosorbide for each molar percent of isosorbide included in the polyester. The T g values of the polyesters could be adjusted between 115 and 163 °C, depending on the isosorbide content. Their mechanical properties were investigated, and ductile properties were achieved up to 57 mol % of isosorbide. These properties are coupled with a very high heat deflection temperature (HDT).

Bio-based copolyesters involving 1,4:3,6-dianhydrohexitols and sebacic acid: 2,6-pyridinedicarboxylic acid as platforms for high gas barrier food packaging

“…Besides, their molecular rigidity and chirality made them popular as platforms for developing new bio-based polymers with high glass transition temperature and/or special optical properties in the past decades. [6][7][8] Also, their non-toxicity allows them to be used in food packaging and bio-medical devices. 7,8 Particularly, the large scale production of high purity isosorbide (POLYSORB s ) by Roquette further facilitates the development of low carbon footprint polymers based on this molecule such as polyesters, polycarbonates and thermoplastic polyurethanes (TPUs).…”

“…13 In addition, the properties can be readily tuned by varying the monomer type and the sequence of incorporation. 6 Succinic acid (SA) is one of the most popular short-chain aliphatic bio-based diacid, and its derivative succinyl dichloride (C4) has already shown potential for the preparation of high T g polyesters with IS or IM. 7,8 Besides, some rigid cyclic monomers, such as 2,5-furandicarboxylic acid (FDCA25) and vanillin, have also been used as bio-based cyclic building blocks.…”

Synthesis of potentially biobased poly(hexamethylene sebacate) via reactive extrusion

“…A second reactor was used to optimize the polycondensation step. It was a 7.5 L stainless steel batch reactor equipped with a mechanical stirrer with torque measurement, a distillation column, a vacuum line and a nitrogen gas inlet [29,30]. The reactor was charged with 10 mol of sebacic acid and 10 mol of hexanediol (~2.8 kg of final polyester).…”

Highly Bio‐Based Unsaturated Polyester Resins with Improved Performance by Incorporating Isosorbide into the Polyester Prepolymer

“…[ 44–46 ] It has been reported that incorporation of ISO units into a polymer backbone leads to improvements on toughness, biodegradability, biocompatibility, and thermal stability. [ 47–50 ] Especially, isosorbide has been tried to incorporate into a variety of UPs to improve mechanical performance of the resultant UPRs. [ 51–53 ]…”

“…[44][45][46] It has been reported that incorporation of ISO units into a polymer backbone leads to improvements on toughness, biodegradability, biocompatibility, and thermal stability. [47][48][49][50] Especially, isosorbide has been tried to incorporate into a variety of UPs to improve mechanical performance of the resultant UPRs. [51][52][53] Itaconic acid (IA) possesses a multifunctional structure with 𝛼,𝛽-unsaturated double bond and two carboxyl groups, thus was considered to be highly flexible for the UPR chemistry.…”