Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications
Abstract Alcoholysis is a promising approach for upcycling postconsumer polylactide (PLA) products into valuable constituents. In addition, an alcohol-acidolysis of PLA by multifunctional 2,2-bis(hydroxymethyl)propionic acid (DMPA) produces lactate oligomers with hydroxyl and carboxylic acid termina...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-02-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-29496-x |
| _version_ | 1811165970727698432 |
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| author | Bunthoeun Nim Sosna Sri Rahayu Kamonchanok Thananukul Chorney Eang Mantana Opaprakasit Atitsa Petchsuk Chariya Kaewsaneha Duangporn Polpanich Pakorn Opaprakasit |
| author_facet | Bunthoeun Nim Sosna Sri Rahayu Kamonchanok Thananukul Chorney Eang Mantana Opaprakasit Atitsa Petchsuk Chariya Kaewsaneha Duangporn Polpanich Pakorn Opaprakasit |
| author_sort | Bunthoeun Nim |
| collection | DOAJ |
| description | Abstract Alcoholysis is a promising approach for upcycling postconsumer polylactide (PLA) products into valuable constituents. In addition, an alcohol-acidolysis of PLA by multifunctional 2,2-bis(hydroxymethyl)propionic acid (DMPA) produces lactate oligomers with hydroxyl and carboxylic acid terminals. In this work, a process for sizing down commercial PLA resin to optimum medium-sized lactate oligomers is developed at a lower cost than a bottom-up synthesis from its monomer. The microwave-assisted reaction is conveniently conducted at 220–240 °C and pressure lower than 100 psi. The PLA resin was completely converted via alcohol-acidolysis reaction, with a product purification yield as high as 93%. The resulting products are characterized by FTIR, 2D-NMR, 1H-NMR, GPC, DSC, and XRD spectroscopy. The effects of PLA: DMPA feed ratios and the incorporation of 1,4-butanediol (BDO) on the structures, properties, and particle formability of the alcohol-acidolyzed products are examined. The products from a ratio of 12:1, which possessed optimum size and structures, are used to synthesize PLA-based polyurethane (PUD) by reacting with 1,6-diisocyanatohexane (HDI). The resulting PUD is employed in encapsulating lavender essential oil (LO). Without using any surfactant, stable LO-loaded nanoparticles are prepared due to the copolymer’s self-stabilizability from its carboxylate groups. The effect of the polymer: LO feed ratio (1.25–3.75: 1) on the physicochemical properties of the resulting nanoparticles, e.g., colloidal stability (zeta potential > -60 mV), hydrodynamic size (300–500 nm), encapsulation efficiency (80–88%), and in vitro release, are investigated. The LO-loaded nanoparticles show non-toxicity to fibroblast cells, with an IC50 value higher than 2000 µg/mL. The products from this process have high potential as drug encapsulation templates in biomedical applications. |
| first_indexed | 2024-04-10T15:44:48Z |
| format | Article |
| id | doaj.art-f8a3c5612afd4976b796502e100510cc |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-10T15:44:48Z |
| publishDate | 2023-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-f8a3c5612afd4976b796502e100510cc2023-02-12T12:11:52ZengNature PortfolioScientific Reports2045-23222023-02-0113112010.1038/s41598-023-29496-xSizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applicationsBunthoeun Nim0Sosna Sri Rahayu1Kamonchanok Thananukul2Chorney Eang3Mantana Opaprakasit4Atitsa Petchsuk5Chariya Kaewsaneha6Duangporn Polpanich7Pakorn Opaprakasit8School of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversitySchool of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversitySchool of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversitySchool of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversityDepartment of Materials Science, Faculty of Science, Chulalongkorn UniversityNational Metal and Materials Technology Center (MTEC), National Science and Technology Development Agency (NSTDA), Thailand Science ParkSchool of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversityNational Nanotechnology Center (NANOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science ParkSchool of Integrated Science and Innovation, Sirindhorn International Institute of Technology (SIIT), Thammasat UniversityAbstract Alcoholysis is a promising approach for upcycling postconsumer polylactide (PLA) products into valuable constituents. In addition, an alcohol-acidolysis of PLA by multifunctional 2,2-bis(hydroxymethyl)propionic acid (DMPA) produces lactate oligomers with hydroxyl and carboxylic acid terminals. In this work, a process for sizing down commercial PLA resin to optimum medium-sized lactate oligomers is developed at a lower cost than a bottom-up synthesis from its monomer. The microwave-assisted reaction is conveniently conducted at 220–240 °C and pressure lower than 100 psi. The PLA resin was completely converted via alcohol-acidolysis reaction, with a product purification yield as high as 93%. The resulting products are characterized by FTIR, 2D-NMR, 1H-NMR, GPC, DSC, and XRD spectroscopy. The effects of PLA: DMPA feed ratios and the incorporation of 1,4-butanediol (BDO) on the structures, properties, and particle formability of the alcohol-acidolyzed products are examined. The products from a ratio of 12:1, which possessed optimum size and structures, are used to synthesize PLA-based polyurethane (PUD) by reacting with 1,6-diisocyanatohexane (HDI). The resulting PUD is employed in encapsulating lavender essential oil (LO). Without using any surfactant, stable LO-loaded nanoparticles are prepared due to the copolymer’s self-stabilizability from its carboxylate groups. The effect of the polymer: LO feed ratio (1.25–3.75: 1) on the physicochemical properties of the resulting nanoparticles, e.g., colloidal stability (zeta potential > -60 mV), hydrodynamic size (300–500 nm), encapsulation efficiency (80–88%), and in vitro release, are investigated. The LO-loaded nanoparticles show non-toxicity to fibroblast cells, with an IC50 value higher than 2000 µg/mL. The products from this process have high potential as drug encapsulation templates in biomedical applications.https://doi.org/10.1038/s41598-023-29496-x |
| spellingShingle | Bunthoeun Nim Sosna Sri Rahayu Kamonchanok Thananukul Chorney Eang Mantana Opaprakasit Atitsa Petchsuk Chariya Kaewsaneha Duangporn Polpanich Pakorn Opaprakasit Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications Scientific Reports |
| title | Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications |
| title_full | Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications |
| title_fullStr | Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications |
| title_full_unstemmed | Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications |
| title_short | Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications |
| title_sort | sizing down and functionalizing polylactide pla resin for synthesis of pla based polyurethanes for use in biomedical applications |
| url | https://doi.org/10.1038/s41598-023-29496-x |
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