Cardanol-based oligomers with “hard core, flexible shell” structures: from synthesis to UV curing applications

Ren, Lei; Zhu, Guigang; Li, Zhiquan; Liu, Xiaoya; Chen, Zhigang; Ariyasivam, Sharonie

doi:10.1039/c5gc00366k

Cited by 49 publications

(27 citation statements)

References 26 publications

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“…The peak at around 0.9 ppm corresponded to the terminal methyl protons of the alkyl chains . After cardanol was modified by acryloyl chloride, the acrylate proton peaks of CH 2 ═CH― appeared at 5.91, 6.31, and 6.53 ppm in Figure B . Compared to the spectra of cardanol Figure A and CA Figure B, the final product was confirmed by the appearance of the methylene protons of the epoxy groups at 2.9 to 3.1 ppm and the disappearance of proton peaks at 5.46 ppm.…”

Section: Resultsmentioning

confidence: 89%

“…36 After cardanol was modified by acryloyl chloride, the acrylate proton peaks of CH 2 ═CHappeared at 5.91, 6.31, and 6.53 ppm in Figure 2B. 22 Compared to the spectra of cardanol Figure 2A and CA Figure 2B, the final product was confirmed by the appearance of the methylene protons of the epoxy groups at 2.9 to 3.1 ppm and the disappearance of proton peaks at 5.46 ppm. The changed chemical shift of the peaks at 1.4 to 2.3 ppm also supports successful oxidation.…”

Section: Synthesis and Characterization Of Ecamentioning

confidence: 92%

“…Photoinduced curing technology which possessed superior properties including high speed, fast production rate at ambient temperature, low energy consumption, less environmental damage, and free of volatile organic compounds, has a wide range of applications in coatings, adhesives, inks, dental composites, and composites . Therefore, incorporating photoinduced curing technology into renewable materials will provide a promising “green + green” strategy to current organic coating industry …”

Section: Introductionmentioning

confidence: 99%

“…20,21 Therefore, incorporating photoinduced curing technology into renewable materials will provide a promising "green + green" strategy to current organic coating industry. 22 2 | EXPERIMENTAL…”

mentioning

confidence: 99%

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Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Shang

Wang

et al. 2018

Polymers for Advanced Techs

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A novel kind of biobased monomer, epoxidized cardanol‐based acrylate (ECA), was successfully synthesized from cardanol via acrylation and epoxidization. The chemical structure was confirmed by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance. Then, the ECA was employed to produce UV‐curable films and coatings copolymerized with castor oil‐based polyurethane acrylate. Compared to coatings from petroleum‐based diluent hydroxyethyl acrylate‐based castor oil‐based polyurethane acrylate resins, ECA‐based biomaterials exhibited a little inferior dilution ability but overcome the drawback of high volumetric shrinkage with a special lower value. Moreover, ultimate properties of the UV‐cured biomaterials such as thermal, mechanical, coating, swelling, and hydrophobic properties were investigated. The UV‐curing behavior was investigated using real‐time IR, and the overall double bond conversion was more than 90%. This biobased UV‐curable cardanol‐based diluent shows a promise in “green + green” materials technologies.

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Section: Resultsmentioning

confidence: 89%

Section: Synthesis and Characterization Of Ecamentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Shang

Wang

et al. 2018

Polymers for Advanced Techs

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“…However, bio‐based epoxy resins are often crystalline solids . Some notable liquid systems that have been recently reported are based on furfural derivatives, terpenes, gallic acid, and cardanol derivatives …”

Section: Introductionmentioning

confidence: 99%

Structure–property relationships of a bio‐based reactive diluent in a bio‐based epoxy resin

Maiorana

Liang

Manas‐Zloczower

et al. 2016

J of Applied Polymer Sci

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ABSTRACT:: The monofunctional glycidyl ether of eugenol (GE) was used as a reactive diluent for the diglycidyl ether of diphenolate n-pentyl ester (DGEDP-Pe). Viscosities of GE and DGEDP-Pe are 25 mPa.s and 11 Pa.s, respectively. Compositions GE/DGEDP-Pe epoxy resins with 5, 10, 15, 20, and 30 wt % GE were analyzed for viscosity reductions and, subsequently, cured with isophorone diamine. The glassy modulus of cured GE/DGEDP-Pe epoxy resins remained between 2000 and 3000 MPa. The glass transition temperature decreased linearly, from 92 8C for neat DGEDP-Pe, with progressively higher loadings of GE to 53 8C at the highest GE loading of 30 wt %. The thermal stability decreased as GE loading increased with a maximum of 30 8C loss in the onset of degradation at 5 wt % mass loss. The role of GE as a reactive diluent is discussed and a range of loadings was determined to be suitable for a vacuum infusion epoxy resin system.

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Functionalization of styrene–butadiene rubber with meta‐pentadecenyl phenol for better processing: A multifunctional additive and renewable resource

Mahata

Prabhavale

Samantarai

et al. 2017

J of Applied Polymer Sci

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Meta‐pentadecenyl phenol, a nonisoprenoid phenolic lipid, is a renewable agricultural resource and also a byproduct of the cashew industry; it is popularly known as cardanol. This study throws light on the grafting of cardanol, which has been established as a multifunctional additive for natural rubber, onto the main‐chain backbone of styrene–butadiene rubber (SBR), a synthetic polymer used to imbibe the multifunctional properties of the former, such as those of a plasticizer, curing promoter, process aid, and antioxidant, into the latter. The grafting was carried out in the solution stage on a trial basis with a peroxide catalyst, and all of the grafting parameters were optimized with a Taguchi methodology. The grafting of cardanol onto the SBR backbone was successfully confirmed by UV–visible spectroscopy, Fourier transform infrared spectroscopy, and NMR analysis. Thermal analysis of the cardanol‐grafted styrene–butadiene rubber (C‐g‐SBR) revealed a higher thermal stability and better plasticizing effect than that those found in the virgin SBR. The rheological properties of the grafted rubber indicated the improvement of the pseudo‐plastic (shear‐thinning) nature compared to that in gum SBR. The unfilled C‐g‐SBR vulcanizates exhibited physicomechanical properties comparable to 5‐phr processing‐oil‐containing SBR [oil‐plasticized styrene–butadiene rubber (OPSBR)] vulcanizates. The carbon‐black‐filled C‐g‐SBR vulcanizates exhibited improved plasticization, a faster curing rate, easy processability, and better physicomechanical properties compared to the 5‐phr OPSBR vulcanizates. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45150.

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Cardanol-based oligomers with “hard core, flexible shell” structures: from synthesis to UV curing applications

Abstract: UV cured polymers based on cardanol exhibit excellent mechanical properties due to the unique “hard core, flexible shell” structures of the hyperbranched renewable oligomers.

Cited by 49 publications

References 26 publications

Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Renewable epoxidized cardanol‐based acrylate as a reactive diluent for UV‐curable resins

Structure–property relationships of a bio‐based reactive diluent in a bio‐based epoxy resin

Functionalization of styrene–butadiene rubber with meta‐pentadecenyl phenol for better processing: A multifunctional additive and renewable resource

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