The cationic polymerization of tung oil and its fatty-acid methyl ester

Lacerda, Talita M.; Gandini, Alessandro

doi:10.1016/j.indcrop.2020.112886

Cited by 19 publications

(18 citation statements)

References 29 publications

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“…In all cases, no detailed mechanisms for the processes were put forward and most studies were carried out in an atmospheric environment and called upon the use of high temperatures for the final setting phase, so that, inevitably, free radicals also intervened in the network formation. Given the lack of information on the cationic polymerization mechanism of tung oil, an investigation on this process was conducted using trifluoroacetic acid (TFA) as initiator, room temperature, and an inert atmosphere [ 132 ], and although some insight could be gathered from the tung oil polymerization, the rapid formation of crosslinked materials hindered a deeper understanding of the mechanistic and structural issues. The methyl ester of α-eleostearic acid was therefore selected to mimic tung oil in this context because its cationic polymerization proceeded without leading to crosslinked products, thus allowing its progress to be followed in a homogeneous medium, notably by NMR spectroscopy [ 132 ].…”

Section: The Case Of Tung Oil: An Old Ally For Original Materialsmentioning

confidence: 99%

“…Given the lack of information on the cationic polymerization mechanism of tung oil, an investigation on this process was conducted using trifluoroacetic acid (TFA) as initiator, room temperature, and an inert atmosphere [ 132 ], and although some insight could be gathered from the tung oil polymerization, the rapid formation of crosslinked materials hindered a deeper understanding of the mechanistic and structural issues. The methyl ester of α-eleostearic acid was therefore selected to mimic tung oil in this context because its cationic polymerization proceeded without leading to crosslinked products, thus allowing its progress to be followed in a homogeneous medium, notably by NMR spectroscopy [ 132 ]. The idea evolved into a more complex system, based on the cationic copolymerization of furfuryl alcohol with tung oil, in order to combine the high intrinsic flexibility of the crosslinked tung oil polymers with the stiffness of the furfuryl alcohol resin, leading to fully biobased crosslinked materials with a tunable glass transition temperature [ 133 ].…”

Section: The Case Of Tung Oil: An Old Ally For Original Materialsmentioning

confidence: 99%

“…Reproduced with permission from Ref. [ 132 ]. Copyright International Journal of Biological Macromolecules 2020.…”

Section: Figurementioning

confidence: 99%

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The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

et al. 2021

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This paper provides an overview of the recent progress in research and development dealing with polymers derived from plant oils. It highlights the widening interest in novel approaches to the synthesis, characterization, and properties of these materials from renewable resources and emphasizes their growing impact on sustainable macromolecular science and technology. The monomers used include unmodified triglycerides, their fatty acids or the corresponding esters, and chemically modified triglycerides and fatty acid esters. Comonomers include styrene, divinylbenzene, acrylics, furan derivatives, epoxides, etc. The synthetic pathways adopted for the preparation of these materials are very varied, going from traditional free radical and cationic polymerizations to polycondensation reactions, as well as metatheses and Diels–Alder syntheses. In addition to this general appraisal, the specific topic of the use of tung oil as a source of original polymers, copolymers, and (nano)composites is discussed in greater detail in terms of mechanisms, structures, properties, and possible applications.

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Section: The Case Of Tung Oil: An Old Ally For Original Materialsmentioning

confidence: 99%

Section: The Case Of Tung Oil: An Old Ally For Original Materialsmentioning

confidence: 99%

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The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

et al. 2021

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“…Given the lack of information on the cationic polymerization mechanism of tung oil, an investigation on this process was conducted using trifluoroacetic acid (TFA) as initiator, room temperature and inert atmosphere, and although some insight could be gathered from the tung oil polymerization, the rapid formation of crosslinked materials hindered a deeper understanding of the mechanistic and structural issues. The methyl ester of α-eleostearic acid was therefore selected to mimic tung oil in this context because its cationic polymerization proceeded without leading to crosslinked products, thus allowing its progress to be followed in a homogeneous medium, notably by NMR spectroscopy [49]. The idea evolved into a more complex system, based on the cationic copolymerization of furfuryl alcohol with tung oil, in order to combine the high intrinsic flexibility of the crosslinked tung oil polymers with the stiffness of the furfuryl alcohol resin, leading to fully biobased crosslinked materials with a tunable glass transition temperature [50].…”

Section: The Case Of Tung Oil: An Old Ally For Original Materialsmentioning

confidence: 99%

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

Gandini¹,

Lacerda²

2020

The First International Conference on &Amp;ldquo;Green” Polymer Materials 2020

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This paper provides an overview of the recent progress in research and development dealing with polymers derived from plant oils. It highlights the widening interest in novel approaches to the synthesis, characterization and properties of these materials from renewable resources and emphasizes their growing impact in sustainable macromolecular science and technology. The monomers used include unmodified triglycerides, their fatty acids or the corresponding esters, and chemically modified triglycerides and fatty acid esters. Comonomers include styrene, divinylbenzene, acrylics, furan derivatives, epoxides, etc. The synthetic pathways adopted for the preparation of these materials are very varied, going from traditional free radical and cationic polymerizations to polycondensation reactions, as well as metatheses and Diels–Alder syntheses. In addition to this general appraisal, the specific topic of the use of tung oil as a source of original polymers, copolymers and nanocomposites is discussed in greater details in terms of mechanisms, structures, properties and possible applications.

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“…Again, the authors reported the utilization of high temperatures and UV irradiation to achieve high conversions. The lack of available information and experimental evidences about the mechanisms involved in the cationic polymerization of tung oil motivated a systematic study, using trifluoroacetic acid as initiator under a nitrogen atmosphere (Lacerda and Gandini 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Furfuryl alcohol/tung oil matrix-based composites reinforced with bacterial cellulose fibres

et al. 2021

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Polymeric materials have drastically changed the society in the last century. However, their non-renewable origin, together with their indiscriminate use and disposal, resulted in a huge accumulation of waste in the environment and raised a wide discussion about the emission of greenhouse gases, which must be considerably reduced to minimize global warming. Thus, the establishment of a consolidated production of polymers prioritizing the use of renewable sources of raw materials became a hot research topic. Vegetable oils are protagonists of this initiative, and their carbon–carbon double bonds are convenient reactive sites for chain growth polymerization reactions. However, typical vegetable oil-based homopolymers often do not display competitive thermo-mechanical properties, and the preparation of the corresponding copolymers and composites is therefore an interesting alternative strategy. Herein, the preparation of composites based on a tung oil/furfuryl alcohol co-continuous network reinforced with bacterial cellulose fibers is described. For this purpose, the cellulose nanofibers were suspended in furfuryl alcohol, and different amounts of the ensuing suspension were mixed with tung oil in the presence of trifluoroacetic acid as cationic initiator. Fourier-transform infrared spectroscopy analysis of all samples indicated the association of both tung oil and furfuryl alcohol in the final materials, with peaks belonging to cellulose superposed at the fingerprint regions of composites. Differential scanning calorimetry and thermogravimetry demonstrated an interesting relationship between the composition and the corresponding thermal properties, and the morphology of the materials was assessed by scanning electron microscopy (SEM), which revealed a homogeneous distribution of cellulosic fibers at lower concentrations. The results gathered here contribute to the development of original macromolecular materials exclusively based on the renewable platform.

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The cationic polymerization of tung oil and its fatty-acid methyl ester

Cited by 19 publications

References 29 publications

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

Furfuryl alcohol/tung oil matrix-based composites reinforced with bacterial cellulose fibres

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