Preparation of bio-degradable polyurethane based on poly(1,3-propylene 3,6,9-trioxaundecanedioate) glycol

The bio-based poly(1,3-propylene 3,6,9-trioxaundecanedioate) glycol (PPTR) was prepared by the reaction between bio-based 1,3-propanediol (bio-PDO) and 3,6,9-trioxaundecanedioic acid. The as-synthesized PPTR combined with bio-PDO was reacted with 1,6-hexamethylene diisocyanate to get a bio-based polyurethane material (PPTR-PU). The PPTR-PU film has high tensile strength (17.9 MPa) and toughness (93.7 MJ/m(3)), and it can be degraded very fast under the existence of HCl and NaOH. The mass loss is 47.8% and 68.4% after 24 h of the degradation in HCl (pH 1) and NaOH (pH 13) solution, respectively. The porcine pancreatic lipase can accelerate the hydrolysis of the film under the physiological environment, leading to an approximately 50% mass loss after 20 d of the enzymatic degradation. The results from H-1 nuclear magnetic resonance, DSC, gel permeation chromatography, and FTIR measurements reveal that the PPTR-PU chains are degraded due to the hydrolysis of ester groups in the PPTR soft segments, leading to the decrease of molecular weights and the increasing degree of hydrogen bonding. The research highlights how to design and prepare the polyurethane material with fast degradable property from bio-based resources.

Automated summary

The bio-based polyurethane material (PPTR-PU) was successfully prepared by reacting bio-based 1,3-propanediol and 3,6,9-trioxaundecanedioic acid with 1,6-hexamethylene diisocyanate. The PPTR-PU film exhibited high tensile strength and toughness, and it underwent rapid degradation in the presence of HCl and NaOH. Porcine pancreatic lipase accelerated the enzymatic degradation of the film. Measurements revealed that the degradation of PPTR-PU occurred through the hydrolysis of ester groups, resulting in decreased molecular weights and increased hydrogen bonding.