Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols
Vanillin, as a promising aromatic aldehyde, possesses worthy structural and bioactive properties useful in the design of novel sustainable polymeric materials. Its versatility and structural similarity to terephthalic acid (TPA) can lead to materials with properties similar to conventional poly(ethy...
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MDPI AG
2022-08-01
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| Series: | International Journal of Molecular Sciences |
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| author | Lesly Dasilva Wandji Djouonkep Alain Pierre Tchameni Naomie Beolle Songwe Selabi Arnaud Kamdem Tamo Ingo Doench Zhengzai Cheng Mario Gauthier Binqiang Xie Anayancy Osorio-Madrazo |
| author_facet | Lesly Dasilva Wandji Djouonkep Alain Pierre Tchameni Naomie Beolle Songwe Selabi Arnaud Kamdem Tamo Ingo Doench Zhengzai Cheng Mario Gauthier Binqiang Xie Anayancy Osorio-Madrazo |
| author_sort | Lesly Dasilva Wandji Djouonkep |
| collection | DOAJ |
| description | Vanillin, as a promising aromatic aldehyde, possesses worthy structural and bioactive properties useful in the design of novel sustainable polymeric materials. Its versatility and structural similarity to terephthalic acid (TPA) can lead to materials with properties similar to conventional poly(ethylene terephthalate) (PET). In this perspective, a symmetrical dimethylated dialkoxydivanillic diester monomer (DEMV) derived from vanillin was synthesized via a direct-coupling method. Then, a series of poly(ether-ester)s were synthesized via melt-polymerization incorporating mixtures of phenyl/phenyloxy diols (with hydroxyl side-chains in the 1,2-, 1,3- and 1,4-positions) and a cyclic diol, 1,4-cyclohexanedimethanol (CHDM). The polymers obtained had high molecular weights (<i>M</i><sub>w</sub> = 5.3–7.9 × 10<sup>4</sup> g.mol<sup>−1</sup>) and polydispersity index (Đ) values of 1.54–2.88. Thermal analysis showed the polymers are semi-crystalline materials with melting temperatures of 204–240 °C, and tunable glass transition temperatures (T<sub>g</sub>) of 98–120 °C. Their 5% decomposition temperature (T<sub>d,5%</sub>) varied from 430–315 °C, which endows the polymers with a broad processing window, owing to their rigid phenyl rings and trans-CHDM groups. These poly(ether-ester)s displayed remarkable impact strength and satisfactory gas barrier properties, due to the insertion of the cyclic alkyl chain moieties. Ultimately, the synergistic influence of the ester and ether bonds provided better control over the behavior and mechanism of in vitro degradation under passive and enzymatic incubation for 90 days. Regarding the morphology, scanning electron microscopy (SEM) imaging confirmed considerable surface degradation in the polymer matrices of both polymer series, with weight losses reaching up to 35% in enzymatic degradation, which demonstrates the significant influence of ether bonds for biodegradation. |
| first_indexed | 2024-03-09T04:21:25Z |
| format | Article |
| id | doaj.art-e596d553e7c148ec92419829051c3aec |
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| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T04:21:25Z |
| publishDate | 2022-08-01 |
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| spelling | doaj.art-e596d553e7c148ec92419829051c3aec2023-12-03T13:47:37ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-08-012316896710.3390/ijms23168967Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether DiolsLesly Dasilva Wandji Djouonkep0Alain Pierre Tchameni1Naomie Beolle Songwe Selabi2Arnaud Kamdem Tamo3Ingo Doench4Zhengzai Cheng5Mario Gauthier6Binqiang Xie7Anayancy Osorio-Madrazo8College of Petroleum Engineering, Applied Chemistry in Oil and Gas Fields, Yangtze University, Jingzhou 434000, ChinaCollege of Petroleum Engineering, Applied Chemistry in Oil and Gas Fields, Yangtze University, Jingzhou 434000, ChinaInstitute of Advanced Materials and Nanotechnology, Wuhan University of Science and Technology, Wuhan 430081, ChinaLaboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, GermanyLaboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, GermanyInstitute of Fine Organic Chemistry and New Organic Materials, Wuhan University of Science and Technology, Wuhan 430081, ChinaDepartment of Chemistry, Institute for Polymer Research, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1, CanadaCollege of Petroleum Engineering, Applied Chemistry in Oil and Gas Fields, Yangtze University, Jingzhou 434000, ChinaLaboratory for Bioinspired Materials—BMBT, Institute of Microsystems Engineering—IMTEK, University of Freiburg, 79110 Freiburg, GermanyVanillin, as a promising aromatic aldehyde, possesses worthy structural and bioactive properties useful in the design of novel sustainable polymeric materials. Its versatility and structural similarity to terephthalic acid (TPA) can lead to materials with properties similar to conventional poly(ethylene terephthalate) (PET). In this perspective, a symmetrical dimethylated dialkoxydivanillic diester monomer (DEMV) derived from vanillin was synthesized via a direct-coupling method. Then, a series of poly(ether-ester)s were synthesized via melt-polymerization incorporating mixtures of phenyl/phenyloxy diols (with hydroxyl side-chains in the 1,2-, 1,3- and 1,4-positions) and a cyclic diol, 1,4-cyclohexanedimethanol (CHDM). The polymers obtained had high molecular weights (<i>M</i><sub>w</sub> = 5.3–7.9 × 10<sup>4</sup> g.mol<sup>−1</sup>) and polydispersity index (Đ) values of 1.54–2.88. Thermal analysis showed the polymers are semi-crystalline materials with melting temperatures of 204–240 °C, and tunable glass transition temperatures (T<sub>g</sub>) of 98–120 °C. Their 5% decomposition temperature (T<sub>d,5%</sub>) varied from 430–315 °C, which endows the polymers with a broad processing window, owing to their rigid phenyl rings and trans-CHDM groups. These poly(ether-ester)s displayed remarkable impact strength and satisfactory gas barrier properties, due to the insertion of the cyclic alkyl chain moieties. Ultimately, the synergistic influence of the ester and ether bonds provided better control over the behavior and mechanism of in vitro degradation under passive and enzymatic incubation for 90 days. Regarding the morphology, scanning electron microscopy (SEM) imaging confirmed considerable surface degradation in the polymer matrices of both polymer series, with weight losses reaching up to 35% in enzymatic degradation, which demonstrates the significant influence of ether bonds for biodegradation.https://www.mdpi.com/1422-0067/23/16/8967bio-based poly(ether-ester)smechanical propertiesgas barrier properties(bio)degradation |
| spellingShingle | Lesly Dasilva Wandji Djouonkep Alain Pierre Tchameni Naomie Beolle Songwe Selabi Arnaud Kamdem Tamo Ingo Doench Zhengzai Cheng Mario Gauthier Binqiang Xie Anayancy Osorio-Madrazo Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols International Journal of Molecular Sciences bio-based poly(ether-ester)s mechanical properties gas barrier properties (bio)degradation |
| title | Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols |
| title_full | Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols |
| title_fullStr | Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols |
| title_full_unstemmed | Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols |
| title_short | Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols |
| title_sort | bio based degradable poly ether ester s from melt polymerization of aromatic ester and ether diols |
| topic | bio-based poly(ether-ester)s mechanical properties gas barrier properties (bio)degradation |
| url | https://www.mdpi.com/1422-0067/23/16/8967 |
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