Acido-alcoholyzed Products of Polylactide (PLA) and Their Use in Enhancing Mechanical Properties, Hydrophilicity, and Cell Compatibility of PLA Nanofibers for Tissue Engineering Applications

Main Article Content

Pattara Somnuake
Atitsa Petchsuk
Mantana Opaprakasit
Pakorn Opaprakasit

Abstract

Alcoholysis and acidolysis effectively transesterify polylactide (PLA) resin into small or medium-sized lactate oligomers with tunable hydrophilicity. The products can then be used to prepare various functional materials. This work employed 2, 2-bis(hydroxymethyl) propionic acid (DMPA) to generate small-sized PLA oligomers with carboxylic and hydroxyl terminals. The chemical structures and compositions of the acido-alcoholyzed PLA (aPLA) were analyzed by proton nuclear magnetic resonance (1H-NMR) and Fourier transform infrared (FTIR) spectroscopy. The optimum product was blended with PLA resin and fabricated into electrospun nanofibers to increase their mechanical properties, hydrophilicity, and biocompatibility. The surface morphology, chemical structures, crystallinity, and properties of the PLA/aPLA blends were characterized by scanning electron microscopy (SEM), FTIR, X-ray diffraction (XRD) spectroscopy, water contact angle (WCA) measurements, tensile tests, and biocompatibility tests. Nanofibers with a ragged surface morphology and a 900-1500 nm size range were generated. The fibers showed higher crystallinity due to the enhanced crystallization induction by the acid and hydroxyl chain ends. Incorporating aPLA increased the elongation at break and the toughness of the fiber mats due to the plasticizing effect and the higher compatibility of aPLA in the PLA matrix. The hydrophilicity of the fiber mats also improved due to the higher contents of the polar end groups, leading to high water absorption in a short time. The cell compatibility results confirmed that the fibers containing 20% aPLAs were suitable for incubating L929 fibroblast cells, which was reflected in the higher adhesion and growth on the cells on the fiber mats within 7 days. The materials have high potential for use in tissue engineering scaffolding and biomedical applications.

Article Details

How to Cite
Somnuake, P., Petchsuk, A., Opaprakasit, M., & Opaprakasit, P. (2026). Acido-alcoholyzed Products of Polylactide (PLA) and Their Use in Enhancing Mechanical Properties, Hydrophilicity, and Cell Compatibility of PLA Nanofibers for Tissue Engineering Applications. CURRENT APPLIED SCIENCE AND TECHNOLOGY, e0268047. https://doi.org/10.55003/cast.2026.268047
Section
Original Research Articles

References

Benhabbour, S. R., Sheardown, H., & Adronov, A. (2008). Cell adhesion and proliferation on hydrophilic dendritically modified surfaces. Biomaterials, 29(31), 4177-4186.

Bhardwaj, N., & Kundu, S. C. (2010). Electrospinning: a fascinating fiber fabrication technique. Biotechnology Advances, 28(3), 325-347.

Casasola, R., Thomas, N. L., Trybala, A., & Georgiadou, S. (2014). Electrospun poly lactic acid (PLA) fibres: Effect of different solvent systems on fibre morphology and diameter. Polymer, 55(18), 4728-4737. https://doi.org/10.1016/j.polymer.2014.06.032

Chen, H.-M., Du, X.-C., Yang, A.-S., Yang, J.-H., Huang, T., Zhang, N., Yang, W., Wang, Y., & Zhang, C.-L. (2014). Effect of graphene oxides on thermal degradation and crystallization behavior of poly(l-lactide). RSC Advances, 4(7), 3443-3456. https://doi.org/10.1039/c3ra45480k

Deitzel, J. M., Kleinmeyer, J., Harris, D., & Tan, N. B. (2001). The effect of processing variables on the morphology of electrospun nanofibers and textiles. Polymer, 42(1), 261-272.

Drelich, J., Chibowski, E., Meng, D. D., & Terpilowski, K. (2011). Hydrophilic and superhydrophilic surfaces and materials. Soft Matter, 7(21), 9804-9828. https://doi.org/10.1039/C1SM05849E

Fuensanta, M., Khoshnood, A., & Martín-Martínez, J. M. (2020). Structure–properties relationship in waterborne poly (urethane-urea)s synthesized with dimethylolpropionic acid (DMPA) internal emulsifier added before, during, and after prepolymer formation. Polymers, 12(11), Article 2478. https://doi.org/10.3390/polym12112478

Ganesan, P., Vanaki, S. M., Thoo, K., & Chin, W. (2016). Air-side heat transfer characteristics of hydrophobic and super-hydrophobic fin surfaces in heat exchangers: A review. International Communications in Heat and Mass Transfer, 74, 27-35.

Haider, A., Haider, S., & Kang, I.-K. (2018). A comprehensive review summarizing the effect of electrospinning parameters and potential applications of nanofibers in biomedical and biotechnology. Arabian Journal of Chemistry, 11(8), 1165-1188. https://doi.org/10.1016/j.arabjc.2015.11.015

Hortos, M., Vinas, M., Espino, S., & Bou, J. J. (2019). Influence of temperature on high molecular weight poly(lactic acid) stereocomplex formation. Express Polymer Letters, 13(2), 123-134. https://doi.org/10.3144/expresspolymlett.2019.12

Huang, C., & Thomas, N. L. (2018). Fabricating porous poly(lactic acid) fibres via electrospinning. European Polymer Journal, 99, 464-476. https://doi.org/10.1016/j.eurpolymj.2017.12.025

Kim, H. H., Kim, M. J., Ryu, S. J., Ki, C. S., & Park, Y. H. (2016). Effect of fiber diameter on surface morphology, mechanical property, and cell behavior of electrospun poly(ε-caprolactone) mat. Fibers and Polymers, 17(7), 1033-1042. https://doi.org/10.1007/s12221-016-6350-x

Lee, K.-M., Park, H., Kim, J., & Chun, D.-M. (2019). Fabrication of a superhydrophobic surface using a fused deposition modeling (FDM) 3D printer with poly lactic acid (PLA) filament and dip coating with silica nanoparticles. Applied Surface Science, 467-468, 979-991. https://doi.org/10.1016/j.apsusc.2018.10.205

Lim, J. Y., Shaughnessy, M. C., Zhou, Z., Noh, H., Vogler, E. A., & Donahue, H. J. (2008). Surface energy effects on osteoblast spatial growth and mineralization. Biomaterials, 29(12), 1776-1784.

López-Fonseca, R., Duque-Ingunza, I., De Rivas, B., Arnaiz, S., & Gutiérrez-Ortiz, J. (2010). Chemical recycling of post-consumer PET wastes by glycolysis in the presence of metal salts. Polymer Degradation and Stability, 95(6), 1022-1028.

Lv, T., Li, J., Liu, L., Huang, S., Li, H., & Jiang, S. (2023). Effects of molecular weight on stereocomplex and crystallization of PLLA/PDLA blends. Polymer, 283, Article 126259. https://doi.org/10.1016/j.polymer.2023.126259

Ma, Z., Hu, Y., Jiang, G., Hou, J., Liu, R., Lu, Y., & Liu, C. (2012). Spontaneous generation of germline characteristics in mouse fibrosarcoma cells. Scientific Reports, 2(1), Article 743. https://doi.org/10.1038/srep00743

Nakayama, Y., Ohmori, T., Tanaka, R., Shiono, T., & Shirahama, H. (2014). Synthesis and properties of polylactide-based poly(ester-urethane)s with ionic groups. Journal of the Japan Institute of Energy, 93(9), 921-925.

Nim, B., Opaprakasit, M., Petchsuk, A., & Opaprakasit, P. (2020). Microwave-assisted chemical recycling of polylactide (PLA) by alcoholysis with various diols. Polymer Degradation and Stability, 181, Article 109363. https://doi.org/10.1016/j.polymdegradstab.2020.109363

Nim, B., & Opaprakasit, P. (2021). Quantitative analyses of products from chemical recycling of polylactide (PLA) by alcoholysis with various alcohols and their applications as healable lactide-based polyurethanes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 255, Article 119684. https://doi.org/10.1016/j.saa.2021.119684

Nim, B., Rahayu, S. S., Thananukul, K., Eang, C., Opaprakasit, M., Petchsuk, A., Kaewsaneha, C., Polpanich, D., & Opaprakasit, P. (2023). Sizing down and functionalizing polylactide (PLA) resin for synthesis of PLA-based polyurethanes for use in biomedical applications. Scientific Reports, 13(1), Article 2284. https://doi.org/10.1038/s41598-023-29496-x

Opaprakasit, P., Opaprakasit, M., & Tangboriboonrat, P. (2007). Crystallization of polylactide and its stereocomplex investigated by two-dimensional Fourier transform infrared correlation spectroscopy employing carbonyl overtones. Applied Spectroscopy, 61(12), 1352-1358.

Palak, H., Güler, E., Nofar, M., & Kayaoğlu, B. K. (2022). Effects of D-lactide content and molecular weight on the morphological, thermal, and mechanical properties of electrospun nanofiber polylactide mats. Journal of Industrial Textiles, 51(2_suppl), 3030S-3056S. https://doi.org/10.1177/15280837221090260

Pang, X., Zhuang, X., Tang, Z., & Chen, X. (2010). Polylactic acid (PLA): research, development and industrialization. Biotechnology Journal, 5(11), 1125-1136. https://doi.org/10.1002/biot.201000135

Petchsuk, A., Buchatip, S., Supmak, W., Opaprakasit, M., & Opaprakasit, P. (2014). Preparation and properties of multi-branched poly (D-lactide) derived from polyglycidol and its stereocomplex blends. Express Polymer Letters, 8(10), 779-789. https://doi.org/10.3144/expresspolymlett.2014.80

Phattarateera, S., & Pattamaprom, C. (2020). The effect of different acrylic-based rubbers on the crystallization behavior of PLA/PDLA stereocomplex. Journal of Polymers and the Environment, 28(6), 1592-1600. https://doi.org/10.1007/s10924-020-01707-w

Pollard, J. W., & Walker, J. M. (1997). Basic cell culture protocols. 2nd Ed. Human Press.

Promnil, S., Numpaisal, P.-O., & Ruksakulpiwat, Y. (2021). Effect of molecular weight on mechanical properties of electrospun poly (lactic acid) fibers for meniscus tissue engineering scaffold. Materials Today: Proceedings, 47(Part 12), 3496-3499. https://doi.org/10.1016/j.matpr.2021.03.504

Pruchniewski, M., Strojny-Cieślak, B., Nakielski, P., Zawadzka, K., Urbańska, K., Rybak, D., Zakrzewska, A., Grodzik, M., & Sawosz, E. (2025). Electrospun poly-(L-lactide) scaffold enriched with GO-AuNPs nanocomposite stimulates skin tissue reconstruction via enhanced cell adhesion and controlled growth factors release. Materials and Design, 251, Article 113713. https://doi.org/10.1016/j.matdes.2025.113713

Sappayasan, M. (2019). Biocomposite scaffolds based on polylactide and chitin/chitosan from fungi extract for tissue engineering applications. [Master of Engineering thesis, Thammasat University]. TU Digital Collections. https://digital.library.tu.ac.th/tu_dc/ frontend/Info/item/dc:175891

Shafrin, E. G., & Zisman, W. A. (1960). Constitutive relations in the wetting of low energy surfaces and the theory of the retraction method of preparing monolayers. The Journal of Physical Chemistry, 64(5), 519-524. https://doi.org/10.1021/j100834a002

Sinha, V., Patel, M. R., & Patel, J. V. (2010). PET waste management by chemical recycling: a review. Journal of Polymers and the Environment, 18(1), 8-25.

Somnuake, P. (2021). Electrospun nanofibers of polylactide (PLA) stereocomplex with super-hydrophobic surfaces for potential use in facial mask and biomedical applications. [Master of Engineering thesis, Thammasat University]. TU Digital Collections. https://digital.library.tu.ac.th/tu_dc/frontend/Info/item/dc:272969

Somnuake, P., Petchsuk, A., Opaprakasit, M., & Opaprakasit, P. (2024a). Sizing down of polylactide (PLA) by 2,2-bis(hydroxymethyl)propionic acid for toughening and enhancing the hydrophilicity of PLA cast films. In The 6th International Conference on Smart Materials and Nanotechnology (SMARTMAT2024), Chiangmai.

Somnuake, P., Puttawong, P., & Wacharawichanant, S. (2024b). Morphology and properties of poly (lactic acid)/ethylene propylene diene monomer blends with micro-cellulose fibers from paper pulp. Advances in Science and Technology, 150, 3-10. https://doi.org/10.4028/p-D4crNi

Van Tam, J. K., Uto, K., Ebara, M., Pagliari, S., Forte, G., & Aoyagi, T. (2012). Mesenchymal stem cell adhesion but not plasticity is affected by high substrate stiffness. Science and Technology of Advanced Materials, 13(6), Article 064205. https://doi.org/10.1088/1468-6996/13/6/064205

Wacharawichanant, S., Wimonsupakit, N., & Kuhaudomlap, S. (2018). Comparison of morphology and mechanical properties of polyoxymethylene/cellulose and poly(lactic acid)/cellulose composites. Materials Science Forum, 916, 19-23. https://doi.org/10.4028/www.scientific.net/MSF.916.19

Wang, D. K., Varanasi, S., Fredericks, P. M., Hill, D. J., Symons, A. L., Whittaker, A. K., & Rasoul, F. (2013). FT‐IR characterization and hydrolysis of PLA‐PEG‐PLA based copolyester hydrogels with short PLA segments and a cytocompatibility study. Journal of Polymer Science Part A: Polymer Chemistry, 51(24), 5163-5176.

Wang, F., Liang, C., Zhang, Y., & Zhang, X. (2017). Defrosting performance of superhydrophobic fin-tube heat exchanger. Applied Thermal Engineering, 113, 229-237.

Weiss, L., & Blumenson, L. E. (1967). Dynamic adhesion and separation of cells in vitro II. Interactions of cells with hydrophilic and hydrophobic surfaces. Journal of cellular Physiology, 70(1), 23-32.

Zhang, J., Duan, Y., Sato, H., Tsuji, H., Noda, I., Yan, S., & Ozaki, Y. (2005). Crystal modifications and thermal behavior of poly (L-lactic acid) revealed by infrared spectroscopy. Macromolecules, 38(19), 8012-8021.