Synthesis of glycerol-based biopolyesters as toughness enhancers for polylactic acid bioplastic through reactive extrusion

ACS Omega

Volumn 1, Issue 6, 2016, Pages 1284-1295

  Valerio, Oscar ^a,b   Pin, Jean Mathieu ^b   Misra, Manjusri ^a,b   Mohanty, Amar K ^a,b  

^a UNIVERSITY OF GUELPH   (Canada)

^b UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85027224895     PISSN: None     EISSN: 24701343     Source Type: Journal    
DOI: 10.1021/acsomega.6b00325     Document Type: Article

References (45)

1. Södergard, A.; Stolt, M. Industrial production of high molecular weight poly (lactic acid). In Poly(lactic acid): Synthesis, Structures, Properties, Processing, and Applications; Auras, R. A., Lim, L.-T., Selke, S. E. M., Tsuji, H., Eds.; John Wiley & Sons, Inc., 2010; pp 27−41.
2. Anderson, K. S.; Schreck, K. M.; Hillmyer, M. A. Toughening polylactide. Polym. Rev. 2008, 48, 85−108.
3. Kfoury, G.; Raquez, J.-M.; Hassouna, F.; Odent, J.; Toniazzo, V.; Ruch, D.; Dubois, P. Recent advances in high performance poly(lactide): From “green” plasticization to super-tough materials via (reactive) compounding. Front. Chem. 2013, 1, 1−46.
4. Liu, H.; Zhang, J. Research Progress in Toughening Modification of Poly(lactic acid). J. Polym. Sci., Part B: Polym. Phys. 2011, 49, 1051− 1083.
5. Nagarajan, V.; Mohanty, A. K.; Misra, M. Perspective on Polylactic Acid (PLA) based Sustainable Materials for Durable Applications: Focus on Toughness and Heat Resistance. ACS Sustainable Chem. Eng. 2016, 4, 2899−2916.
6. Ciriminna, R.; Pina, C. D.; Rossi, M.; Pagliaro, M. Understanding the glycerol market. Eur. J. Lipid Sci. Technol. 2014, 116, 1432−1439.
7. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F. Improved utilisation of renewable resources: New important derivatives of glycerol. Green Chem. 2008, 10, 13−30.
8. Sheldon, R. A. Green and sustainable manufacture of chemicals from biomass: State of the art. Green Chem. 2014, 16, 950−963.
9. Agach, M.; Delbaere, S.; Marinkovic, S.; Estrine, B.; Nardello-Rataj, V. Characterization, stability and ecotoxic properties of readily biodegradable branched oligoesters based on bio-sourced succinic acid and glycerol. Polym. Degrad. Stab. 2012, 97, 1956−1963.
10. Agach, M.; Delbaere, S.; Marinkovic, S.; Estrine, B.; Nardello-Rataj, V. Synthesis, characterization, biodegradability and surfactant properties of bio-sourced lauroyl poly(glycerol-succinate)oligoesters. Colloids Surf., A 2013, 419, 263−273.
11. Agach, M.; Marinkovic, S.; Estrine, B.; Nardello-Rataj, V. Acyl Poly(glycerol-succinic acid)oligoesters: Synthesis, Physicochemical and Functional Properties, and Biodegradability. J. Surfactants Deterg. 2016, 19, 933−941.
12. Sarkar, A.; Santra, S.; Kundu, S. K.; Hajra, A.; Zyryanov, G. V.; Chupakhin, O. N.; Charushin, V. N.; Majee, A. A decade update on solvent and catalyst-free neat organic reactions: A step forward towards sustainability. Green Chem. 2016, 18, 4475−4525.
13. Tang, S. L. Y.; Smith, R. L.; Poliakoff, M. Principles of green chemistry: Productively. Green Chem. 2005, 7, 761.
14. Gu, L.; Li, Y.; Cheng, S. Modification of Poly(L-lactide) by Poly(glycerol-sebacate). J. Funct. Polym. 2008, 21, 343−348.
15. Coativy, G.; Misra, M.; Mohanty, A. K. Microwave Synthesis and Melt Blending of Glycerol Based Toughening Agent with Poly(lactic acid). ACS Sustainable Chem. Eng. 2016, 4, 2142−2149.
16. Valerio, O.; Horvath, T.; Pond, C.; Misra, M.; Mohanty, A. Improved utilization of crude glycerol from biodiesel industries: Synthesis and characterization of sustainable biobased polyesters. Ind. Crops Prod. 2015, 78, 141−147.
17. Wyatt, V. T. Lewis Acid-Catalyzed Synthesis of Hyperbranched Polymers Based on Glycerol and Diacids in Toluene. J. Am. Oil Chem. Soc. 2011, 89, 313−319.
18. Stumbe, J.-F.; Bruchmann, B. Hyperbranched polyesters based on adipic acid and glycerol. Macromol. Rapid Commun. 2004, 25, 921− 924.
19. Maliger, R.; Halley, P. J.; Cooper-White, J. J. Poly(glycerol-sebacate)bioelastomers-kinetics of step-growth reactions using Fourier transform (FT)-Raman spectroscopy. J. Appl. Polym. Sci. 2013, 127, 3980−3986.
20. Odian, G. Step Polymerization. In Principles of Polymerization, 4th ed.; Wiley-Interscience: New York, 2004; pp 39−197.
21. Medeiros, E. S.; Offeman, R. D.; Klamczynski, A. P.; Glenn, G. M.; Mattoso, L. H. C.; Orts, W. J. Synthesis, Characterization and Nanocomposite Formation of Poly(glycerol succinate-co-maleate) with Nanocrystalline Cellulose. J. Polym. Environ. 2014, 22, 219−226.
22. Tang, J.; Zhang, Z.; Song, Z.; Chen, L.; Hou, X.; Yao, K. Synthesis and characterization of elastic aliphatic polyesters from sebacic acid, glycol and glycerol. Eur. Polym. J. 2006, 42, 3360−3366.
23. Kfoury, G.; Hassouna, F.; Raquez, J.-M.; Toniazzo, V.; Ruch, D.; Dubois, P. Tunable and Durable Toughening of Polylactide Materials via Reactive Extrusion. Macromol. Mater. Eng. 2014, 299, 583−595.
24. He, Y.-S.; Zeng, J.-B.; Liu, G.-C.; Li, Q.-T.; Wang, Y.-Z. Supertough poly(L-lactide)/crosslinked polyurethane blends with tunable impact toughness. RSC Adv. 2014, 4, 12857.
25. Liu, H.; Song, W.; Chen, F.; Guo, L.; Zhang, J. Interaction of Microstructure and Interfacial Adhesion on Impact Performance of Polylactide (PLA) Ternary Blends. Macromolecules 2011, 44, 1513− 1522.
26. Yu, R.-L.; Zhang, L.-S; Feng, Y.-H.; Zhang, R.-Y.; Zhu, J. Improvement in toughness of polylactide by melt blending with biobased poly(ester)urethane. Chin. J. Polym. Sci. 2014, 32, 1099−1110.
27. Zhang, L.; Xiong, Z.; Shams, S. S.; Yu, R.; Huang, J.; Zhang, R.; Zhu, J. Free radical competitions in polylactide/bio-based thermoplastic polyurethane/free radical initiator ternary blends and their final properties. Polymer 2015, 64, 69−75.
28. Dorgan, J. R.; Janzen, J.; Clayton, M. P.; Hait, S. B.; Knauss, D. M. Melt rheology of variable L-content poly(lactic acid). J. Rheol. 2005, 49, 607.
29. Nouri, S.; Dubois, C.; Lafleur, P. G. Synthesis and characterization of polylactides with different branched architectures. J. Polym. Sci., Part B: Polym. Phys. 2015, 53, 522−531.
30. Perkins, W. G. Polymer toughness and impact resistance. Polym. Eng. Sci. 1999, 39, 2445−2460.
31. Lin, Y.; Zhang, K.-Y.; Dong, Z.-M.; Dong, L.-S.; Li, Y.-S. Study of hydrogen-bonded blend of polylactide with biodegradable hyperbranched poly(ester amide). Macromolecules 2007, 40, 6257−6267.
32. Liu, G.-C.; He, Y.-S.; Zeng, J.-B.; Li, Q.-T.; Wang, Y.-Z. Fully biobased and supertough polylactide-based thermoplastic vulcanizates fabricated by peroxide-induced dynamic vulcanization and interfacial compatibilization. Biomacromolecules 2014, 15, 4260−4271.
33. Wojcieszak, R.; Santarelli, F.; Paul, S.; Dumeignil, F.; Cavani, F.; Goncalves, R. V. Recent developments in maleic acid synthesis from bio-based chemicals. Sustainable Chem. Processes 2015, 3, 1−11.
34. Kfoury, G.; Raquez, J.-M.; Hassouna, F.; Leclere, P.; Toniazzo, V.; Ruch, D.; Dubois, P. Toughening of poly(lactide) using polyethylene glycol methyl ether acrylate: Reactive versus physical blending. Polym. Eng. Sci. 2015, 55, 1408−1419.
35. Bhardwaj, R.; Mohanty, A. K. Modification of brittle polylactide by novel hyperbranched polymer-based nanostructures. Biomacromolecules 2007, 8, 2476−2484.
36. Nerkar, M.; Ramsay, J. A.; Ramsay, B. A.; Kontopoulou, M. Dramatic Improvements in Strain Hardening and Crystallization Kinetics of PLA by Simple Reactive Modification in the Melt State. Macromol. Mater. Eng. 2014, 299, 1419−1424.
37. Chen, Y.; Yuan, D.; Xu, C. Dynamically Vulcanized Biobased Polylactide/Natural Rubber Blend Material with Continuous Cross-Linked Rubber Phase. ACS Appl. Mater. Interfaces 2014, 6, 3811−3816.
38. Fang, H.; Jiang, F.; Wu, Q.; Ding, Y.; Wang, Z. Supertough Polylactide Materials Prepared through in Situ Reactive Blending with PEG-Based Diacrylate Monomer. ACS Appl. Mater. Interfaces 2014, 6, 13552−13563.
39. Lu, X.; Wei, X.; Huang, J.; Yang, L.; Zhang, G.; He, G.; Wang, M.; Qu, J. Supertoughened Poly(lactic acid)/Polyurethane Blend Material by in Situ Reactive Interfacial Compatibilization via Dynamic Vulcanization. Ind. Eng. Chem. Res. 2014, 53, 17386−17393.
40. Anderson, K. S.; Lim, S. H.; Hillmyer, M. A. Toughening of polylactide by melt blending with linear low-density polyethylene. J. Appl. Polym. Sci. 2003, 89, 3757−3768.
41. Spinella, S.; Cai, J.; Samuel, C.; Zhu, J.; McCallum, S. A.; Habibi, Y.; Raquez, J.-M.; Dubois, P.; Gross, R. A. Polylactide/Poly(ωhydroxytetradecanoic acid) Reactive Blending: A Green Renewable Approach to Improving Polylactide Properties. Biomacromolecules 2015, 16, 1818−1826.
42. Li, Y.; Cook, W. D.; Moorhoff, C.; Huang, W.-C.; Chen, Q.-Z. Synthesis, characterization and properties of biocompatible poly-(glycerol sebacate) pre-polymer and gel. Polym. Int. 2013, 62, 534− 547.
43. d'Arcy, R.; Burke, J.; Tirelli, N. Branched polyesters: Preparative strategies and applications. Adv. Drug Delivery Rev. 2016, DOI: 10.1016/j.addr.2016.05.005.
44. Ruellan, A.; Guinault, A.; Sollogoub, C.; Ducruet, V.; Domenek, S. Solubility factors as screening tools of biodegradable toughening agents of polylactide. J. Appl. Polym. Sci. 2015, 132, 42476 (1−11).
45. 3 strategy: Recent advances in description and control of fine topology. Polym. Chem. 2016, 7, 3643−3663.