Non-Toxic, Green Polyhydroxyurethanes Synthesized From Abundant Glucose Sources

Area of Science:

• Polymer Chemistry
• Biomaterials Science
• Organic Synthesis

Background:

• Conventional polyurethanes often rely on toxic isocyanates, posing health and environmental risks.
• There is a growing demand for sustainable and biocompatible polymers derived from renewable resources.
• Non-isocyanate polyurethanes (NIPUs) offer a safer alternative but require efficient synthesis routes.

Purpose of the Study:

• To synthesize novel cyclic carbonate monomers from D-glucose.
• To develop a series of non-isocyanate polyhydroxyurethanes (NIPUs) using these monomers.
• To evaluate the physicochemical properties, biocompatibility, and degradability of the synthesized NIPUs.

Main Methods:

• Synthesis of a 6-membered mono-cyclic carbonate from D-glucose.
• Thiol-ene reaction to produce 6-membered bis-cyclic carbonates.
• Catalyst-free polymerization of bis-cyclic carbonates with various diamines to form NIPUs.
• Characterization using NMR, FTIR, HRMS, GPC, TGA, and DSC.

Main Results:

• Novel mono- and bis-cyclic carbonates were synthesized in good to excellent yields (65%-80%).
• Six NIPUs (NIPU1-NIPU6) were successfully prepared with molecular weights ranging from 7,500 to 160,000 g/mol.
• The NIPUs exhibited glass transition temperatures between -7°C and -21°C and degradation temperatures (Td,10%) between 195°C and 245°C.
• All synthesized NIPUs demonstrated enzymatic degradability and biocompatibility.

Conclusions:

• D-glucose derived cyclic carbonates are effective monomers for synthesizing NIPUs.
• The developed NIPUs are non-toxic, biocompatible, and enzymatically degradable.
• The presence of hydroxyl groups allows for further functionalization, making these polymers suitable for biomedical applications, coatings, and adhesives.