Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters
The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin‐derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable...
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| Published in | ChemSusChem Vol. 11; no. 15; pp. 2529 - 2539 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
09.08.2018
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1864-5631 1864-564X 1864-564X |
| DOI | 10.1002/cssc.201801059 |
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| Abstract | The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin‐derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co‐monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5‐furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel‐permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum‐based polyesters currently employed in the plastics industry, specifically for applications in which high‐temperature stability is essential to ensure overall system integrity.
Think BG: Bisguaiacol (BG), a lignin‐derived bisphenol analogue, is treated with different activated diacids to investigate the effect of the co‐monomer structures on the physical properties of the products. The polymers show glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. These new polyesters hold promise for use as renewable and biodegradable alternatives to petroleum‐based polyesters. |
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| AbstractList | The utilization of wood-derived building blocks (xylochemicals) to replace fossil-based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin-derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co-monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5-furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1 H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel-permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass-transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum-based polyesters currently employed in the plastics industry, specifically for applications in which high-temperature stability is essential to ensure overall system integrity.The utilization of wood-derived building blocks (xylochemicals) to replace fossil-based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin-derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co-monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5-furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1 H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel-permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass-transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum-based polyesters currently employed in the plastics industry, specifically for applications in which high-temperature stability is essential to ensure overall system integrity. The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin‐derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co‐monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5‐furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel‐permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum‐based polyesters currently employed in the plastics industry, specifically for applications in which high‐temperature stability is essential to ensure overall system integrity. The utilization of wood-derived building blocks (xylochemicals) to replace fossil-based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin-derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co-monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5-furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel-permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass-transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum-based polyesters currently employed in the plastics industry, specifically for applications in which high-temperature stability is essential to ensure overall system integrity. The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin‐derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co‐monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5‐furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1 H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel‐permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum‐based polyesters currently employed in the plastics industry, specifically for applications in which high‐temperature stability is essential to ensure overall system integrity. The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science. Here, we demonstrate that bisguaiacol (BG), a lignin‐derived bisphenol analogue, can be used to prepare biobased polyesters with remarkable thermal properties. BG was treated with different activated diacids to investigate the effect of co‐monomer structures on the physical properties of the products. Namely, derivatives of adipic acid, succinic acid, and 2,5‐furandicarboxylic acid were used. Moreover, a terephthalic acid derivative was used for comparison purposes. The products were characterized by 1H NMR spectroscopy, attenuated total reflectance FTIR spectroscopy, gel‐permeation chromatography, thermogravimetric analysis, and differential scanning calorimetry to assess their structural and thermal properties in detail. The polymers showed glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. Furthermore, the susceptibility of the polyester to enzymatic hydrolysis was investigated to assess the potential for further surface functionalization and/or recycling and biodegradation. Indeed, hydrolysis with two different enzymes from the bacteria Thermobifida cellulosilytica led to the release of monomers, as quantified by HPLC. The results of this study indicate that our new polyesters represent promising renewable and biodegradable alternatives to petroleum‐based polyesters currently employed in the plastics industry, specifically for applications in which high‐temperature stability is essential to ensure overall system integrity. Think BG: Bisguaiacol (BG), a lignin‐derived bisphenol analogue, is treated with different activated diacids to investigate the effect of the co‐monomer structures on the physical properties of the products. The polymers show glass‐transition temperatures ranging up to 160 °C and thermal stabilities in excess of 300 °C. These new polyesters hold promise for use as renewable and biodegradable alternatives to petroleum‐based polyesters. |
| Author | Fischer, Isabel Biundo, Antonino Curia, Silvio Stanzione, Joseph F. Braunschmid, Verena Gübitz, Georg M. |
| Author_xml | – sequence: 1 givenname: Silvio orcidid: 0000-0003-3386-7199 surname: Curia fullname: Curia, Silvio email: curia@rowan.edu organization: Rowan University – sequence: 2 givenname: Antonino surname: Biundo fullname: Biundo, Antonino organization: Austrian Centre of Industrial Biotechnology (ACIB) – sequence: 3 givenname: Isabel surname: Fischer fullname: Fischer, Isabel organization: Austrian Centre of Industrial Biotechnology (ACIB) – sequence: 4 givenname: Verena surname: Braunschmid fullname: Braunschmid, Verena organization: Austrian Centre of Industrial Biotechnology (ACIB) – sequence: 5 givenname: Georg M. surname: Gübitz fullname: Gübitz, Georg M. organization: University of Natural Resources and Life Sciences (BOKU) – sequence: 6 givenname: Joseph F. orcidid: 0000-0003-0464-835X surname: Stanzione fullname: Stanzione, Joseph F. email: stanzione@rowan.edu organization: Rowan University |
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| Keywords | renewable resources building blocks polymers polyesters xylochemicals |
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| Snippet | The utilization of wood‐derived building blocks (xylochemicals) to replace fossil‐based precursors is an attractive research subject of modern polymer science.... The utilization of wood-derived building blocks (xylochemicals) to replace fossil-based precursors is an attractive research subject of modern polymer science.... |
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| SubjectTerms | Acids Biodegradability Biodegradation building blocks Differential scanning calorimetry Fourier transforms High performance liquid chromatography Hydrolysis Monomers NMR spectroscopy Physical properties Plastics industry Polyester resins Polyesters Polymers Reflectance renewable resources Spectrum analysis Succinic acid Terephthalic acid Thermodynamic properties Thermogravimetric analysis Thermoplastic resins xylochemicals |
| Title | Towards Sustainable High‐Performance Thermoplastics: Synthesis, Characterization, and Enzymatic Hydrolysis of Bisguaiacol‐Based Polyesters |
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