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

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...

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Published inEnvironmental 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
LanguageEnglish
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
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Abstract 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.
AbstractList 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.
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 Tg 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.
To reduce the global CO 2 footprint of plastics, bio- and CO 2 -based feedstock are considered the most important design features for plastics. Oxalic acid from CO 2 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 CO 2 -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. This work shows the potential for tuning the composition of biodegradable PISOX copolyesters, for optimizing the resulting properties (thermal-, mechanical-, barrier-, hydrolysis-, and biodegradability) to target certain applications, such as polymer coating of controlled-release fertilizers, films, and rigids for packaging, 3D printing, etc.
To reduce the global CO footprint of plastics, bio- and CO -based feedstock are considered the most important design features for plastics. Oxalic acid from CO and isosorbide from biomass are interesting rigid building blocks for high polyesters. The biodegradability of a family of novel fully renewable (bio- and CO -based) poly(isosorbide- -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.
Author de Rijke, Eva
Wang, Yue
Tietema, Albert
Weinland, Daniel H.
van der Maas, Kevin
Parsons, John R.
Gruter, Gert-Jan M.
Trijnes, Dio
van Putten, Robert-Jan
AuthorAffiliation van‘t Hoff Institute for Molecular Sciences (HIMS)
University of Amsterdam
Avantium Support BV
Institute for Biodiversity and Ecosystem Dynamics (IBED)
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Keywords marine-degradable polyester
isosorbide
structure property relation
biobased
renewable
biodegradable plastic
oxalic acid
hydrolysis
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Snippet 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...
To reduce the global CO footprint of plastics, bio- and CO -based feedstock are considered the most important design features for plastics. Oxalic acid from CO...
To reduce the global CO 2 footprint of plastics, bio- and CO 2 -based feedstock are considered the most important design features for plastics. Oxalic acid...
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StartPage 2293
SubjectTerms 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
Title Relationship between Composition and Environmental Degradation of Poly(isosorbide-co-diol oxalate) (PISOX) Copolyesters
URI http://dx.doi.org/10.1021/acs.est.2c09699
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