Semi-aromatic polyesters based on a carbohydrate-derived rigid diol for engineering plastics

Area of Science:

• Polymer Chemistry
• Materials Science
• Carbohydrate Chemistry

Background:

• Polyesters are versatile polymers with diverse applications.
• Developing novel monomers from renewable resources is crucial for sustainable polymer production.
• Isohexide derivatives offer unique structural features for polymer synthesis.

Purpose of the Study:

• To synthesize novel carbohydrate-based polyesters using extended isoidide (XII).
• To investigate the properties of polyesters derived from XII and aromatic dicarboxylic acids.
• To evaluate the potential of XII as a monomer for high-performance engineering polymers.

Main Methods:

• Melt polymerization of isoidide-2,5-dimethanol (XII) with dimethyl terephthalate (TA) and dimethyl furan-2,5-dicarboxylate (FDCA).
• Solid-state post-condensation (SSPC) to achieve high molecular weight polymers.
• Nuclear Magnetic Resonance (NMR) spectroscopy to confirm stereochemical integrity.
• Thermal analysis (DSC, TGA) to determine glass transition temperature (Tg), melting temperature (Tm), and thermal stability.

Main Results:

• Successfully synthesized semi-crystalline prepolymers and high molecular weight polyesters (Mn up to 30 kg/mol).
• Preservation of the stereochemical configuration of XII during polymerization confirmed by NMR.
• Polyesters exhibited excellent thermal stability up to 380°C.
• High glass transition temperatures (Tg: 105°C for TA, 94°C for FDCA) and melting temperatures (Tm: 284°C for TA, 250°C for FDCA).

Conclusions:

• Extended isoidide (XII) is a promising renewable diol for synthesizing high-performance, semi-aromatic polyesters.
• The developed polymerization and post-condensation methods are industrially relevant.
• The resulting polyesters possess desirable thermal and mechanical properties for engineering applications.