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Influence of Ozonized Soybean Oil as a Biobased Plasticizer on the Toughness of Polylactic Acid

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Abstract

This work aimed to study the mechanism of toughness improvement of polylactic acid (PLA) by using a biobased plasticizer. Ozonized soybean oil (OSBO), acting as a biobased plasticizer, was prepared by the ozonolysis reaction. The functional groups and chemical structure of OSBO were characterized by FTIR and NMR techniques, respectively. Plasticized PLA specimens were prepared by compounding using a corotating twin-screw extruder and sheet forming using a compression molding machine. The influences of OSBO contents, varying from 0 to 15 wt%, on PLA were evaluated via mechanical and thermal testing and morphological analysis. After the ozonolysis reaction, there was an increase in ester groups and the formation of hydroxyl groups in OSBO. With increasing OSBO content, it was found that elongation at break and impact strength tended to increase, whereas tensile strength decreased. The glass transition, crystallization and melting temperatures of PLA continuously decreased as a function of OSBO content. The presence of OSBO enhanced crystallization of PLA. OSBO at low content acted as a plasticizer for PLA, whereas OSBO at 15 wt% formed fine oil droplets acting as an impact absorber by energy dissipation.

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The raw/processed data required to reproduce these findings cannot be shared at this time as the data also forms part of an ongoing study.

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References

  1. Öz AT, Süfer Ö, ÇelebiSezer Y (2017) Poly(lactic acid) films in food packaging systems. Food Sci Nutr Technol 2:131. https://doi.org/10.23880/FSNT-16000131

    Article  Google Scholar 

  2. Jiménez L, Mena MJ, Prendiz J, Salas L, Vega-Baudrit J (2019) Polylactic acid (PLA) as a bioplastic and its possible applications in the food industry. J Food Sci Nutr 5:100048. https://doi.org/10.24966/FSN-1076/100048

    Article  Google Scholar 

  3. Zhao X, Hu H, Wang X, Yu X, Zhou W, Peng S (2020) Super tough poly(lactic acid) blends: a comprehensive review. RSC Adv 10:13316–13368. https://doi.org/10.1039/D0RA01801E

    Article  CAS  Google Scholar 

  4. Han L, Han C, Dong L (2013) Morphology and properties of the biosourced poly(lactic acid)/poly(ethylene oxide-b-amide-12) blends. Polym Compos 34:122–130. https://doi.org/10.1002/pc.22383

    Article  CAS  Google Scholar 

  5. Wang X, Zhuang Y, Dong L (2013) Study of biodegradable polylactide/poly(butylene carbonate) blend. J Appl Polym Sci 127:471–477. https://doi.org/10.1002/app.37735

    Article  CAS  Google Scholar 

  6. Pluta M, Piorkowska E (2015) Tough crystalline blends of polylactide with block copolymers of ethylene glycol and propylene glycol. Polym Test 46:79–87. https://doi.org/10.1016/j.polymertesting.2015.06.014

    Article  CAS  Google Scholar 

  7. Wang Y, Wei Z, Leng X, Shen K, Li Y (2016) Highly toughened polylactide with epoxidized polybutadiene by in-stu reactive compatibilization. Polym 92:74–83. https://doi.org/10.1016/j.polymer.2016.03.081

    Article  CAS  Google Scholar 

  8. Rashmi BJ, Prashantha K, Lacrampe M-F, Krawczak P (2015) Toughening of poly(lactic acid) without sacrificing stiffness and strength by melt-blending with polyamide 11 and selective localization of halloysite nanotubes. Express Polym Lett 9:721–735. https://doi.org/10.3144/expresspolymlett.2015.67

    Article  CAS  Google Scholar 

  9. Gigante V, Canesi I, Cinelli P, Coltelli MB, Lazzeri A (2019) Rubber toughening of polylactic acid (PLA) with poly(butylene adipate-co-terephthalate (PBAT): mechanical properties, fracture mechanics and analysis of ductile-to-brittle behavior while varying temperature and test speed. Eur Polym J 115:125–137. https://doi.org/10.1016/j.eurpolymj.2019.03.015

    Article  CAS  Google Scholar 

  10. Ge XG, George S, Law S, Sain M (2011) Mechanical properties and morphology of polylactide composites with acrylic impact modifier. J Macromol Sci B 50:2070–2083. https://doi.org/10.1080/00222348.2011.557585

    Article  CAS  Google Scholar 

  11. Meng B, Tao J, Deng JJ, Wu ZH, Yang MB (2011) Toughening of polylactide with higher loading of nano-titania particles coated by poly(ε-caprolactone). Mater Lett 65:729–732. https://doi.org/10.1016/j.matlet.2010.11.029

    Article  CAS  Google Scholar 

  12. Song X, Chen Y, Xu Y, Wang C (2014) Study on tough blends of polylactide and acrylic impact modifier. BioResources 9:1939–1952. https://doi.org/10.15376/biores.9.2.1939-1952

    Article  Google Scholar 

  13. Silverajah VSG, Ibrahim NA, Zainuddin N, Yunus WMZW, Hassan HA (2012) Mechanical, thermal and morphological properties of poly(lactic acid)/epoxidized palm olein blend. Molecules 17:11729–11747. https://doi.org/10.3390/molecules171011729

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Tanrattanakul V, Bunkaew P (2014) Effect of different plasticizers on the properties of bio-based thermoplastic elastomer containing poly(lactic acid) and natural rubber. Express Polym Lett 8:387–396. https://doi.org/10.3144/expresspolymlett.2014.43

    Article  CAS  Google Scholar 

  15. Avolio R, Castaldo R, Avella M, Cocca M, Gentile G, Fiori S, Errico ME (2018) PLA-based plasticized nanocomposites: effect of polymer/plasticizer/filler interactions on the time evolution of properties. Compos Part B-Eng 152:267–274. https://doi.org/10.1016/j.compositesb.2018.07.011

    Article  CAS  Google Scholar 

  16. Imre B, Pukánszky B (2013) Compatibilization in bio-based and biodegradable polymer blends. Eur Polym J 49:1215–1233. https://doi.org/10.1016/j.eurpolymj.2013.01.019

    Article  CAS  Google Scholar 

  17. Burgos N, Tolaguera D, Fiori S, Jiménez A (2014) Synthesis and characterization of lactic acid oligomers: evaluation of performance as poly(lactic acid) plasticizers. J Polym Environ 22:227–235. https://doi.org/10.1007/s10924-013-0628-5

    Article  CAS  Google Scholar 

  18. Martin O, Avérous L (2001) Poly(lactic acid): plasticization and properties of biodegradable multiphase systems. Polym 42:6209–6219. https://doi.org/10.1016/S0032-3861(01)00086-6

    Article  CAS  Google Scholar 

  19. Darie-Niţӑ RN, Vasile C, Irimia A, Lipşa R, Rȃpȃ M (2016) Evaluation of some eco-friendly plasticizers for PLA films processing. J Appl Polym Sci 133:43223–43233. https://doi.org/10.1002/app.43223

    Article  CAS  Google Scholar 

  20. Hassouna F, Raquez J-M, Addiego F, Dubois P, Toniazzo V, Ruch D (2011) New approach on the development of plasticized polylactide (PLA): Grafting of poly(ethylene glycol) (PEG) via reactive extrusion. Eur Polym J 47:2134–2144. https://doi.org/10.1016/j.eurpolymj.2011.08.001

    Article  CAS  Google Scholar 

  21. Hassouna F, Raquez J-M, Addiego F, Toniazzo V, Dubois P, Ruch D (2012) New development on plasticized poly(lactide): chemical grafting of citrate on PLA by reactive extrusion. Eur Polym J 48:404–415. https://doi.org/10.1016/j.eurpolymj.2011.12.001

    Article  CAS  Google Scholar 

  22. Shirai MA, Müller CMO, Grossmann MVE, Yamashita F (2015) Adipate and citrate esters as plasticizers for poly(lactic acid)/thermoplastic starch sheets. J Polym Environ 23:54–61. https://doi.org/10.1007/s10924-014-0680-9

    Article  CAS  Google Scholar 

  23. Avolio R, Castaldo R, Gentile G, Ambrogi V, Fiori S, Avella M, Cocca M, Errico ME (2015) Plasticization of poly(lactic acid) through blending with oligomers of lactic acid: effect of the physical aging on properties. Eur Polym J 66:533–542. https://doi.org/10.1016/j.eurpolymj.2015.02.040

    Article  CAS  Google Scholar 

  24. Erikson DR (1995) Practical handbook of soybean processing and utilization. AOCS Press, Illinois

    Google Scholar 

  25. Tran P, Graiver D, Narayan R (2005) Ozone-mediated polyol synthesis from soybean oil. J Am Oil Chem Soc 82:653–659. https://doi.org/10.1007/s11746-005-1124-z

    Article  CAS  Google Scholar 

  26. Garrison TF, Kessler MR (2016). In: Madbouly S, Zhang C, Kessler MR (eds) Bio-based plant oil polymers and composites. Elsevier, Oxford

    Google Scholar 

  27. Vasanthan N, Ly O (2009) Effect of microstructure on hydrolytic degradation studies of poly(l-lactic acid) by FTIR spectroscopy and differential scanning calorimetry. Polym Degrad Stabil 94:1364–1372. https://doi.org/10.1016/j.polymdegradstab.2009.05.015

    Article  CAS  Google Scholar 

  28. Uzuna H, Kaynak EG, Ibanoglu E, Ibanoglu S (2018) Chemical and structural variations in hazelnut and soybean oils after ozone treatments. Grasas Aceites 69:e253. https://doi.org/10.3989/gya.1098171

    Article  CAS  Google Scholar 

  29. Mahou R, Wandrey C (2012) Versatile route to synthesize heterobifunctional poly(ethylene glycol) of variable functionality for subsequent pegylation. Polym 4:561–589. https://doi.org/10.3390/polym4010561

    Article  CAS  Google Scholar 

  30. Wu M, Church DF, Mahier TJ, Barker SA, Pryor WA (1992) Separation and spectral data of the six isomeric ozonides from methyl oleate. Lipids 27:129–135. https://doi.org/10.1007/BF02535812

    Article  CAS  PubMed  Google Scholar 

  31. Soriano UN Jr, Migo VP, Matsumura M (2003) Functional group analysis during ozonation of sunflower oil methyl esters by FT-IR and NMR. Chem Phys Lipids 126:133–140. https://doi.org/10.1016/j.chemphyslip.2003.07.001

    Article  CAS  PubMed  Google Scholar 

  32. Al-Mulla EAJ, Ibrahim NAB, Shameli K, Ahmad MB, Yunus WMZW (2014) Effect of epoxidized palm oil on the mechanical and morphological properties of a PLA–PCL blend. Res Chem Intermed 40:689–698. https://doi.org/10.1007/s11164-012-0994-y

    Article  CAS  Google Scholar 

  33. Dai X, Xiong Z, Na H, Zhu J (2014) How does epoxidized soybean oil improve the toughness of microcrystalline cellulose filled polylactide acid composites? Compos Sci Technol 90:9–15. https://doi.org/10.1016/j.compscitech.2013.10.009

    Article  CAS  Google Scholar 

  34. Tee YB, Talib RA, Abdan K, Chin NL, Basha RK, Yunos KFM (2016) Comparative study of chemical, mechanical, thermal, and barrier properties of poly(lactic acid) plasticized with epoxidized soybean oil and epoxidized palm oil. BioResources 11:1518–1540. https://doi.org/10.15376/biores.11.1.1518-1540

    Article  Google Scholar 

  35. Ali F, Chang YW, Kang SC, Yoon JY (2009) Thermal, mechanical and rheological properties of poly(lactic acid)/epoxidized soybean oil blends. Polym Bull 62:91–98. https://doi.org/10.1007/s00289-008-1012-9

    Article  CAS  Google Scholar 

  36. Hachana N, Wongwanchai T, Chaochanchaikul K, Harnnarongchai W (2017) Influence of crosslinking agent and chain extender on properties of gamma-irradiated PLA. J Polym Environ 25:323–333. https://doi.org/10.1007/s10924-016-0812-5

    Article  CAS  Google Scholar 

  37. Tábi T, Sajó IE, Szabó F, Luyt AS, Kovács JG (2010) Crystalline structure of annealed polylactic acid and its relation to processing. Express Polym Lett 4:659–668. https://doi.org/10.3144/expresspolymlett.2010.80

    Article  CAS  Google Scholar 

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Acknowledgements

This research work was financially supported by Rajamangala University of Technology Phra Nakhon (RMUTP) [Grant No. 59110503/2]. The authors also are grateful to King Mongkut’s University of Technology Thonburi (KMUTT) for supporting ozone generator.

Funding

Financial support for the research was provided by Rajamangala University of Technology Phra Nakhon (RMUTP) [Grant No. 59110503/2].

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Authors and Affiliations

  1. Division of Industrial Materials Science, Faculty of Science and Technology, Rajamangala University of Technology Phra Nakhon, Bangkok, 10800, Thailand

    Kantima Chaochanchaikul

  2. Department of Materials and Production Technology Engineering, Faculty of Engineering, King Mongkut’s University of Technology North Bangkok, Bangkok, 10800, Thailand

    Pornlada Pongmuksuwan

Authors
  1. Kantima Chaochanchaikul
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  2. Pornlada Pongmuksuwan
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1. KC: Conceptualization, Methodology, Writing—Original Draft, Writing—Review & Editing. 2. PP: Methodology, Validation, Writing—Original Draft.

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Correspondence to Kantima Chaochanchaikul.

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Chaochanchaikul, K., Pongmuksuwan, P. Influence of Ozonized Soybean Oil as a Biobased Plasticizer on the Toughness of Polylactic Acid. J Polym Environ 30, 1095–1105 (2022). https://doi.org/10.1007/s10924-021-02264-6

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