Facile synthesis of a novel bio-based methacrylate monomer derived from tung oil and its application for solvent-free thermosetting coatings

Man, Limin; Hu, Yang; Feng, Yajuan; Zhang, Chaoqun; Yuan, Teng; Yang, Zhuohong

doi:10.1016/j.indcrop.2019.03.047

Cited by 39 publications

(21 citation statements)

References 46 publications

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“…The FT-IR spectrum of IPDI-HEA is shown in Figure S2 . In the spectrum of RSO, the characteristic peak at 3008 cm −1 was derived from the stretching vibration band of =C–H [ 38 ]. The peak occurred at 2931 cm −1 and 2854 cm −1 , which arose from the C–H asymmetric stretch vibration in methylene and methyl group stretching on the chain, the strong peak at 1744 cm −1 was ascribed to the C=O groups of triglyceride [ 10 ].…”

Section: Resultsmentioning

confidence: 99%

Rubber Seed Oil-Based UV-Curable Polyurethane Acrylate Resins for Digital Light Processing (DLP) 3D Printing

et al. 2021

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Novel UV-curable polyurethane acrylate (PUA) resins were developed from rubber seed oil (RSO). Firstly, hydroxylated rubber seed oil (HRSO) was prepared via an alcoholysis reaction of RSO with glycerol, and then HRSO was reacted with isophorone diisocyanate (IPDI) and hydroxyethyl acrylate (HEA) to produce the RSO-based PUA (RSO-PUA) oligomer. FT-IR and 1H NMR spectra collectively revealed that the obtained RSO-PUA was successfully synthesized, and the calculated C=C functionality of oligomer was 2.27 per fatty acid. Subsequently, a series of UV-curable resins were prepared and their ultimate properties, as well as UV-curing kinetics, were investigated. Notably, the UV-cured materials with 40% trimethylolpropane triacrylate (TMPTA) displayed a tensile strength of 11.7 MPa, an adhesion of 2 grade, a pencil hardness of 3H, a flexibility of 2 mm, and a glass transition temperature up to 109.4 °C. Finally, the optimal resin was used for digital light processing (DLP) 3D printing. The critical exposure energy of RSO-PUA (15.20 mJ/cm2) was lower than a commercial resin. In general, this work offered a simple method to prepare woody plant oil-based high-performance PUA resins that could be applied in the 3D printing industry.

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Section: Resultsmentioning

confidence: 99%

Rubber Seed Oil-Based UV-Curable Polyurethane Acrylate Resins for Digital Light Processing (DLP) 3D Printing

et al. 2021

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“…In fact, due to the possible formation of stable conjugated radical intermediates, tung oil can be homo- and copolymerized, in a strategy that was first described in the late 1960s and again in the early 1980s [ 121 ]. The most recent contributions consider a prior chemical modification of tung oil with acrylic and methacrylic moieties, leading to materials of superior thermal and mechanical properties, which are readily cured by UV light [ 122 , 123 ]. A more original strategy called upon the copolymerization reaction of crude tung oil and furfuryl methacrylate under inert atmosphere, initiated by benzoyl peroxide, and the final networks were obtained in a second step based on the Diels–Alder click reaction between pendant furan moieties and residual conjugated double bonds of tung oil, which was performed under high pressure and high temperature [ 124 ].…”

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

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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“…In fact, due to the possible formation of stable conjugated radical intermediates, tung oil can be homo-and copolymerized, in a strategy that was first described in the late 1960s and again in the early 1980s [45]. The most recent contributions consider a prior chemical modification of tung oil with acrylic and methacrylic moieties, leading to materials of superior thermal and mechanical properties, readily cured by UV light [46,47]. A more original strategy called upon the copolymerization reaction of crude tung oil and furfuryl methacrylate under inert atmosphere, initiated by benzoyl peroxide, and the final networks were obtained in a second step based on the Diels-Alder click reaction between pendant furan moieties and residual conjugated double bonds of tung oil, which was performed under high pressure and high temperature [48].…”

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 “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.

show abstract

Facile synthesis of a novel bio-based methacrylate monomer derived from tung oil and its application for solvent-free thermosetting coatings

Cited by 39 publications

References 46 publications

Rubber Seed Oil-Based UV-Curable Polyurethane Acrylate Resins for Digital Light Processing (DLP) 3D Printing

Rubber Seed Oil-Based UV-Curable Polyurethane Acrylate Resins for Digital Light Processing (DLP) 3D Printing

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

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