Synthesis of a tung oil–rosin adduct via the diels–alder reaction: Its reaction mechanism and properties in an ultraviolet‐curable adhesive

Wu, Jianbing; Zhang, Tong; Ma, Guozhang; Li, Ping; Ling, Lixia; Wang, Qianqian

doi:10.1002/app.39495

Cited by 17 publications

(5 citation statements)

References 26 publications

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“…Plant oils have the features of environmentally benign, abundance, biodegradability, and triglyceride structures; thus, they have been used as an ideal substitute to prepare bio-based prepolymers for UV-curable coatings [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Plant-oil-based epoxy acrylate (EA) is one of the common UV-curable prepolymers, which is usually prepared through the ring-opening reaction of epoxidized plant oils with acrylic acid (AA) or its derivatives.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

Tang

Zhang

et al. 2020

Polymers

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Novel oil-based epoxy acrylate (EA)-like prepolymers were synthesized via the ring-opening reaction of epoxidized plant oils with a new unsaturated carboxyl acid precursor (MAAMA) synthesized by reacting maleic anhydride (MA) with methallyl alcohol (MAA). Since the employed epoxidized oils including epoxidized soybean oil (ESO), epoxidized rubber seed oil (ERSO), and epoxidized wilsoniana seed oil (EWSO) possessed epoxy values of 7.34–4.38%, the obtained epoxy acrylate (EA)-like prepolymers (MMESO, MMERSO, and MMEWSO) indicated a C=C functionality of 7.81–4.40 per triglyceride. Furthermore, effects of the C=C functionality and the addition of hydroxyethyl methacrylate (HEMA) diluent on the ultimate properties of the resulting UV-cured EA-like materials were investigated and compared with those of commercially available acrylated ESO (AESO) resins. As the C=C functionality increased, the storage modulus at 25 °C (E’25), glass transition temperature (Tg), 5% weight–loss temperature (T5), tensile strength and modulus (σ and E), and hardness of the coating for both the pure EA and EA/HEMA resins increased significantly as well. These properties indicated similar trends when comparing the EA materials with 30% of HEMA with those pure EA materials. Specially, although ERSO had a clearly lower epoxy value that ESO, both the UV-cured pure MMERSO and MMERSO/HEMA materials showed much better E’25, Tg, σ, and E than their AESO counterparts, indicating that the MAAMA modification of epoxidized plant oils was much more effective than the modification of acrylic acid to achieve high-performance oil-based epoxy acrylate resins.

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Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

Tang

Zhang

et al. 2020

Polymers

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“…Resin synthesis was performed by acrylation of TO via Diels-Alder (DA) reaction and the successful reaction was confirmed by ATR-FTIR. In Figure 1a, the FTIR spectrum of TO showed a shoulder peak at 3012 cm −1 (Figure 1b) and a strong signal at 996 cm −1 corresponding to the trans-trans conjugated double bonds, and a weak peak at 964 cm −1 arising from the cis double bonds (Figure 1a) [39]. The sharp signal at 1742 cm −1 was attributed to ester-carbonyl stretching.…”

Section: Resultsmentioning

confidence: 97%

Hydrophobic Shape-Memory Biocomposites from Tung-Oil-Based Bioresin and Onion-Skin-Derived Nanocellulose Networks

et al. 2020

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The fabrication of smart biocomposites from sustainable resources that could replace today’s petroleum-derived polymer materials is a growing field of research. Here, we report preparation of novel biocomposites using nanocellulose networks extracted from food residue (onion skin) and a vegetable oil-based bioresin. The resin was synthesized via the Diels-Alder reaction between furfuryl methacrylate and tung oil at various ratios of the components. The onion-skin-extracted cellulose nanofiber and cellulose nanocrystal networks were then impregnated with the resins yielding biocomposites that exhibited improved mechanical strength and higher storage modulus values. The properties of the resins, as well as biocomposites, were affected by the resin compositions. A 190–240-fold increase in mechanical strength was observed in the cellulose nanofiber (CNF) and cellulose nanocrystal (CNC)-reinforced biocomposites with low furfuryl methacrylate content. The biocomposites exhibited interesting shape-memory behavior with 80–96% shape recovery being observed after 7 creep cycles.

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“…Some studies have shown that the unique ring structure of rosin can reduce the stress generated in the curing process of buffer film and smoothens the surface of the buffer film after curing. Wu et al [80] used the above-mentioned characteristics to modify TO with rosin. After hydroquinone was added into the container, D-A reaction occurred between TO and rosin in different proportions to obtain a TO Figure 5: Synthesis and theoretical structure of HG-MAT and PG-MAT [76] rosin D-A product, as shown in Fig.…”

Section: Modification Of To By Other Dienophile D-a Addition Reactionsmentioning

confidence: 99%

Research Progress of Tung Oil/UV Photocomposite Curing Material

Zhao¹,

Xiao²,

Li³

et al. 2023

Journal of Renewable Materials

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Tung oil (TO)/ultraviolet (UV) photo-composite curing material possesses the characteristics of low curing temperature, low material shrinkage and low environmental pollution. Accordingly, this material must be developed and utilized with the conjugated double bonds contained in the long chain of the main structure (α-tung acid) molecules in the refined TO. The aforementioned material can be chemically modified using a variety of chemical methods to develop a new TO-based UV photocurable material due to its unique chemical properties. This work reviews the research progress of TO/UV photo-composite curing materials in recent years. Firstly, the chemical structure and application of TO and UV Photocatalysis Technology were briefly introduced. Secondly, the research status of novel TO/UV photo-composite curing materials developed by the Diels-Alder reaction was discussed. The method and curing effect of the UV curing system constructed by other chemically modified TO were also discussed. Thereafter, the application of TO in industrial production is introduced from four directions: the application of TO in biodiesel, the application in synthetic resin, the application in self-healing coating and microcapsules and other applications. Finally, the research and application prospects of TO/UV photo-composite curing materials were presented.

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Synthesis of a tung oil–rosin adduct via the diels–alder reaction: Its reaction mechanism and properties in an ultraviolet‐curable adhesive

Cited by 17 publications

References 26 publications

Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

Hydrophobic Shape-Memory Biocomposites from Tung-Oil-Based Bioresin and Onion-Skin-Derived Nanocellulose Networks

Research Progress of Tung Oil/UV Photocomposite Curing Material

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