Relationship between Composition and Environmental Degradation of Poly(isosorbide-co-diol oxalate) (PISOX) Copolyesters

• Published in: Environmental science & technology Vol. 58; no. 5; pp. 2293 - 2302
• Main Authors: Wang, Yue, van der Maas, Kevin, Weinland, Daniel H., Trijnes, Dio, van Putten, Robert-Jan, Tietema, Albert, Parsons, John R., de Rijke, Eva, Gruter, Gert-Jan M.
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 06.02.2024
• Subjects: Ambient temperature; Biodegradability; Biodegradation; Biodegradation, Environmental; Bioplastics; Carbon Dioxide; Carbon footprint; Cellulose; Composition; Degradability; Environmental degradation; Hydrolysis; Isosorbide - chemistry; Mineralization; Oxalates; Oxalic acid; Plastics; Polyester resins; Polyesters; Polyesters - chemistry; Polyesters - metabolism; Polymers; Soil; Soil temperature; Soils; Sustainable Systems; marine-degradable polyester; isosorbide; structure property relation; biobased; renewable; biodegradable plastic; oxalic acid; hydrolysis
• ISSN: 0013-936X; 1520-5851
• DOI: 10.1021/acs.est.2c09699

To reduce the global CO2 footprint of plastics, bio- and CO2-based feedstock are considered the most important design features for plastics. Oxalic acid from CO2 and isosorbide from biomass are interesting rigid building blocks for high T g polyesters. The biodegradability of a family of novel fully renewable (bio- and CO2-based) poly­(isosorbide-co-diol) oxalate (PISOX-diol) copolyesters was studied. We systematically investigated the effects of the composition on biodegradation at ambient temperature in soil for PISOX (co)­polyesters. Results show that the lag phase of PISOX (co)­polyester biodegradation varies from 0 to 7 weeks. All (co)­polyesters undergo over 80% mineralization within 180 days (faster than the cellulose reference) except one composition with the cyclic codiol 1,4-cyclohexanedimethanol (CHDM). Their relatively fast degradability is independent of the type of noncyclic codiol and results from facile nonenzymatic hydrolysis of oxalate ester bonds (especially oxalate isosorbide bonds), which mostly hydrolyzed completely within 180 days. On the other hand, partially replacing oxalate with terephthalate units enhances the polymer’s resistance to hydrolysis and its biodegradability in soil. Our study demonstrates the potential for tuning PISOX copolyester structures to design biodegradable plastics with improved thermal, mechanical, and barrier properties.