Synthesis and characterization of novel renewable tung oil-based UV-curable active monomers and bio-based copolymers

Liang, Bin; Kuang, Shaojie; Huang, Jiajian; Man, Limin; Yang, Zhuohong; Yuan, Teng

doi:10.1016/j.porgcoat.2019.01.007

Cited by 43 publications

(22 citation statements)

References 31 publications

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“…The FT-IR spectra of ERSO, MMERSO, EWSO, and MMEWSO are depicted in Figure S2 . In the MAAMA spectrum, the strong absorption bands around 2500–3400 cm −1 , 1643 cm −1 , and 816 cm −1 were attributed to the characteristic peaks of carboxyl groups, C=C extensional vibration, and C=C bend vibration, respectively [ 45 ]. In the spectra of ESO, ERSO, and EWSO, the peaks at 823 cm −1 related to epoxy groups were observed [ 23 ].…”

Section: Resultsmentioning

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: Resultsmentioning

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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“…The second degradation stage occurred between 340 and 460 • C mainly due to the molecular chain decomposition and carbonization of the cross-linked polymers. In addition, as shown in Table 3, when the grafting number increased, the values of T 10% , T 50% , and char yield also increased, indicating that the vegetable oil-based prepolymers with a higher grafting number had a higher double bond density, and it was easier to obtain a higher cross-linking density, thereby improving the thermal stability of the films [36]. Overall, all cured films had excellent thermal stability, indicating that they could be used at high temperatures.…”

Section: Thermal Stabilitymentioning

confidence: 93%

“…Each CoO molecule contained 4.36 double bonds. In the 1 H NMR spectrum of ACoO, the peaks at H a (6.30-6.50 ppm), H b (6.10-6.20 ppm), and H c (5.75-5.90 ppm) corresponded to the three double bond protons on the acrylate groups, respectively (Scheme 2) [36]. The ratio of peak areas was about 1:1:1.…”

Section: Structure Analysis Of Vegetable Oil-based Acrylate Prepolymersmentioning

confidence: 98%

“…In addition, it can be seen from Figure 3a that all films only had one tanδ peak, indicating that the formulated systems had good compatibility between the different components. In order to further study the thermo-mechanical properties of the films, the cross-linking density (v e ) of the films can be calculated by the following formula [18,36]:…”

Section: Dynamic Mechanical Analysis (Dma)mentioning

confidence: 99%

“…In this study, the vegetable oil-based prepolymers with a higher number of acrylate grafting hada higher double bond density,so it was easier to obtain a higher cross-linking density, so their storage modulus was increased. In addition, it can be seen from Figure 3athat all films only had one tanδ peak, indicating that the formulated systems had good compatibility between the different components.In order to further study the thermo-mechanical properties of the films, the cross-linking density (ve) of the films canbe calculated by the following formula [18,36]…”

Section: Dynamic Mechanical Analysis (Dma)mentioning

confidence: 99%

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One-Step Synthesis of Novel Renewable Vegetable Oil-Based Acrylate Prepolymers and Their Application in UV-Curable Coatings

Lin

Zhang

et al. 2020

Polymers

Self Cite

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With the rapid development of social economy, problems such as volatile organic compound (VOC) pollution and the excessive consumption of global petroleum resources have become increasingly prominent. People are beginning to realize that these problems not only affect the ecological environment, but also hinder the development of the organic polymer material industry based on raw fossil materials. Therefore, the modification and application of bio-based materials are of theoretical and practical significance. In this study, a series of vegetable oil-based acrylate prepolymers were synthesized by one-step acrylation using palm oil, olive oil, peanut oil, rapeseed oil, corn oil, canola oil, and grapeseed oil as raw materials, and the effect of different double bond contents on the product structure and grafting rate was investigated. Furthermore, the as-prepared vegetable oil-based acrylate prepolymers, polyurethane acrylate (PUA-2665), trimethylolpropane triacrylate (TMPTA), and photoinitiator (PI-1173) were mixed thoroughly to prepare ultraviolet (UV)-curable films. The effect of different grafting numbers on the properties of these films was investigated. The results showed that as the degree of unsaturation increased, the acrylate grafting number and the cross-linking density increased, although the acrylation (grafting reaction) rate decreased. The reason was mainly because increasing the double bond content could accelerate the reaction rate, while the grafted acrylic groups had a steric hindrance effect to prevent the adjacent double bonds from participating in the reaction. Furthermore, the increase in grafting number brought about the increase in the structural functionality of prepolymers and the cross-linking density of cured films, which led to the enhancement in the thermal (glass transition temperature) and mechanical (tensile strength, Young’s modulus) properties of the cured films.

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Preparation and properties of green UV‐curable itaconic acid cross‐linked modified waterborne polyurethane coating

Dong

Ren

Duan

et al. 2021

J of Applied Polymer Sci

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Waterborne polyurethane (WPU) coating, as a kind of green product, can replace solvent polyurethane coating, but its application in the field of coating is limited since its defects such as slow curing efficiency, low strength, and water resistance. In this study, a trifunctional itaconic acid-based crosslinking agent (IHA) was synthesized from itaconic acid and hydroxyethyl acrylate. A series of green UV-curable WPU coatings were prepared by introducing IHA into WPU prepolymer in different proportions (2.5 $ 10 wt.%). IHA posed as crosslinking agent in WPU, which can not only enhance strength, but also accelerate curing rate in WPU coatings. The results demonstrated that the gel content and hydrophobic angle of the modified WPU coating (WPU-IHA) are increased by 25.6% and 34.8 , respectively, indicating a good water resistance.Most notably, due to the increase of crosslinking degree and the decrease of chain mobility, the UV-curable WPU coating shows excellent mechanical properties with 21.9 MPa in tensile strength and a pencil hardness of 5H, which is substantially higher than that of pure WPU coatings. Therefore, the IHA shows great potential to substitute petroleum-based crosslinking agents in the preparation of environmentally friendly UV-curable WPU coatings with high strength and good surface scratch hardness.

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Synthesis and characterization of novel renewable tung oil-based UV-curable active monomers and bio-based copolymers

Cited by 43 publications

References 31 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

One-Step Synthesis of Novel Renewable Vegetable Oil-Based Acrylate Prepolymers and Their Application in UV-Curable Coatings

Preparation and properties of green UV‐curable itaconic acid cross‐linked modified waterborne polyurethane coating

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