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New Tricarboxylate Plasticizers for Use in Polylactic Acid: Synthesis, Thermal Behavior, Mechanical Properties and Durability

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Abstract

We report the use of novel biobased plasticizers prepared starting from citric acid (CA) in polylactic acid (PLA). Citric acid based plasticizers are well-known softeners for PLA, with citrate esters as the most commonly used class. However, citrate esters are known to leach out of the plastic material over time. This problem is currently addressed by acetylating the tertiary hydroxyl group of citric acid via complex and environmentally polluting processes. An alternative strategy consists in the reductive removal of the tertiary hydroxyl group, resulting in propane-1,2,3-tricarboxylic acid. Derivatizing this compound leads to novel plasticizers which have not been tested in PLA yet. Here, different esters of propane-1,2,3-tricarboxylic acid were synthesized and blended in PLA. Their influence on the thermal (Tg and Tm) and the mechanical properties (Young’s modulus, stress and strain) of PLA along with their migration out of the material were compared to those of commercially available citric acid based plasticizers. Our results show that similar or better results were obtained with these new PLA plasticizers.

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Acknowledgements

This project has received funding from VLAIO (HBC.2019.2387), in a collaborative project between Citribel and KULeuven. Wouter Stuyck is grateful to the FWO for his SB PhD fellowship (1SC1519N). F.D.P., D.D.V. and M.D. acknowledge the Research Foundation—Flanders (FWO) for financial support through SBO grant S001819N. The computational resources and services used in this work were provided by the VSC (Flemish Supercomputing Center), funded by the Research Foundation—Flanders (FWO) and the Flemish Government. J.V. acknowledges the Research Foundation—Flanders (FWO) for a junior postdoctoral mandate (Project No. 12E6423N). The authors would like the thank A. Vananroye, C. Poisson and V. Jeroen for performing training in using the various tools used in this work.

Funding

Agentschap Innoveren en Ondernemen, HBC.2019.2387, Fonds Wetenschappelijk Onderzoek, S001819N, 12E6423N, S001819N, 1SC1519N.

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Authors and Affiliations

  1. Center for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), K.U. Leuven, Louvain, Flanders, Belgium

    Anthony De Bruyne, Galahad O’Rourke, Wouter Stuyck, Jarne Leinders & Dirk De Vos

  2. Soft Matter, Rheology and Technology (SMaRT), K.U. Leuven, Louvain, Flanders, Belgium

    Kenneth Cerdán Gómez & Peter Van Puyvelde

  3. Eenheid Algemene Chemie (ALGC), Vrije Universiteit Brussel (VUB), Pleinlaan 2, 1050, Brussels, Belgium

    Mats Denayer & Frank De Proft

  4. Center for Molecular Modeling (CMM), Ghent University, Technologiepark-Zwijnaarde 46, 9052, Zwijnaarde, Belgium

    Jelle Vekeman

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  1. Anthony De Bruyne
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Contributions

A.D.B wrote the main manuscript text and obtained the larger part of the results. K.C provided results regarding the mechanical properties (Table 5 + suppl. info.) and reviewed the manuscript. G.R. provided/helped with TGA measurements (Table 6 + suppl. info.). M.D., J.V. and F.P provided results regarding Computational methods (Figure 3). W.S. supervised research and reviewed the manuscript. J.L. provided/helped with DSC results. D.D.V and P.V.P provided intellectual input, techniques used in this work (TGA, DSC, NMR, etc.), supervised research and reviewed the manuscript.

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De Bruyne, A., Gómez, K.C., O’Rourke, G. et al. New Tricarboxylate Plasticizers for Use in Polylactic Acid: Synthesis, Thermal Behavior, Mechanical Properties and Durability. J Polym Environ (2024). https://doi.org/10.1007/s10924-024-03254-0

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