Novel Sulfur-Containing Polyurethanes using 5-(Chloromethyl)Furfural as a Renewable Building Block

Area of Science:

• Polymer Chemistry
• Materials Science
• Green Chemistry

Background:

• The demand for sustainable polymeric materials drives research into biomass-derived molecular platforms.
• 5-(chloromethyl)furfural (CMF) is a key biomass precursor for novel monomers and chemicals.
• Developing efficient synthesis routes for biomass-derived polymers is crucial for industrial applications.

Purpose of the Study:

• To synthesize novel biomass-derived diols from CMF.
• To create new polyurethanes using these diols and assess their properties.
• To explore the chemical degradation of synthesized polyurethanes for recycling.

Main Methods:

• Synthesis of novel biomass-derived diols via reaction of CMF with dithiols, followed by reduction.
• Polyurethane synthesis through polyaddition of diols with diisocyanates catalyzed by an organic base.
• Characterization of polymer properties including molecular weight, glass transition temperature, and degradation temperature.
• Synthesis of a nearly fully biomass-derived polymer via Curtius rearrangement and chemical degradation studies.

Main Results:

• Novel biomass-derived diols were synthesized in very good yields.
• Twelve new polyurethanes were successfully synthesized with varying molecular weights (1.7–57.7 kDa).
• The polyurethanes exhibited high degradation temperatures (Td5% > 170 °C) and glass transition temperatures ranging from 22 to 120 °C.
• A nearly fully biomass-derived polymer was synthesized, and its chemical degradation was investigated.

Conclusions:

• Efficient synthesis of biomass-derived diols and novel polyurethanes is achievable from CMF.
• The synthesized polyurethanes possess favorable thermal properties suitable for various applications.
• The study highlights the potential for developing sustainable polymers with pathways for chemical recycling.