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Journal of Coatings Technology and Research

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08-08-2018

Synthesis and properties of UV-curable cardanol-based acrylate oligomers with cyclotriphosphazene core

Authors: Yan Yuan, Miao Chen, Qiaohua Zhou, Ren Liu

Published in: Journal of Coatings Technology and Research | Issue 1/2019

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Abstract

Multiarm cardanol-based oligomers with a cyclotriphosphazene core were prepared through a nucleophilic substitution reaction; the structures of oligomers were fully characterized and confirmed through Fourier transfer infrared spectrometry, ¹H nuclear magnetic resonance (NMR), ³¹P NMR, and gel permeation chromatography. The designed multiarm bio-based acrylates (AECC) were successfully prepared by epoxidizing the unsaturated aliphatic chain of cardanol segments with m-chloroperoxybenzoic acid and acrylating epoxy groups. The synthesized oligomers contain rigid phosphazene/benzene rings as “hard cores” and long aliphatic chains as “flexible shells.” Compared with commercial hyperbranched polyurethane acrylate (CN2302) and acrylated epoxidized soybean oil, cured AECC coatings and films exhibited not only greater hardness, excellent adhesion, higher glass transition temperatures, and excellent mechanical properties but also good thermal stability and biodegradability. We successfully obtained a high-performance UV-curing resin that has a high biorenewable material content and can meet basic daily requirements.

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Okada, H, Tokunaga, T, Liu, X, Takayanagi, S, Matsushima, A, Shimohigashi, Y, “Direct Evidence Revealing Structural Elements Essential for the High Binding Ability of Bisphenol A to Human Estrogen-Related Receptor-γ.” Environ. Health Perspect., 116 (1) 32–38 (2008)CrossRef

De, B, Gupta, K, Mandal, M, Karak, N, “Biodegradable Hyperbranched Epoxy from Castor Oil-Based Hyperbranched Polyester Polyol.” ACS Sustain. Chem. Eng., 2 (3) 445–453 (2013)CrossRef

Du, X, Li, L, Li, J, Yang, C, Frenkel, N, Welle, A, Heissler, S, Nefedov, A, Grunze, M, Levkin, PA, “UV-Triggered Dopamine Polymerization: Control of Polymerization, Surface Coating, and Photopatterning.” Adv. Mater., 26 (47) 8029–8033 (2014)CrossRef

Çanak, TÇ, Kaya, K, Serhatlı, IE, “Boron Containing UV-Curable Epoxy Acrylate Coatings.” Prog. Org. Coat., 77 (11) 1911–1918 (2014)CrossRef

Ng, F, Bonnet, L, David, G, Caillol, S, “Novel Biobased and Food Contact Epoxy Coatings for Glass Toughening Applications.” Prog. Org. Coat., 109 1–8 (2017)CrossRef

Darroman, E, Durand, N, Boutevin, B, Caillol, S, “New Cardanol/Sucrose Epoxy Blends for Biobased Coatings.” Prog. Org. Coat., 83 47–54 (2015)CrossRef

Darroman, E, Durand, N, Boutevin, B, Caillol, S, “Improved Cardanol Derived Epoxy Coatings.” Prog. Org. Coat., 91 9–16 (2016)CrossRef

Huang, K, Zhang, P, Zhang, J, Li, S, Li, M, Xia, J, Zhou, Y, “Preparation of Biobased Epoxies Using Tung Oil Fatty Acid-Derived C21 Diacid and C22 Triacid and Study of Epoxy Properties.” Green Chem., 15 (9) 2466–2475 (2013)CrossRef

Balachandran, VS, Jadhav, SR, Vemula, PK, John, G, “Recent Advances in Cardanol Chemistry in a Nutshell: From a Nut to Nanomaterials.” Chem. Soc. Rev., 42 (2) 427–438 (2013)CrossRef

10.

Shibata, M, Itakura, Y, Watanabe, H, “Bio-based Thermosetting Resins Composed of Cardanol Novolac and Bismaleimide.” Polym. J., 45 (7) 758–765 (2013)CrossRef

11.

Liu, Y, Wang, J, Xu, S, “Synthesis and Curing Kinetics of Cardanol-Based Curing Agents for Epoxy Resin by In Situ Depolymerization of Paraformaldehyde.” J. Polym. Sci. Part A Polym. Chem., 52 (4) 472–480 (2014)CrossRef

12.

Liu, R, Zhang, X, Zhu, J, Liu, X, Wang, Z, Yan, J, “UV-Curable Coatings from Multiarmed Cardanol-Based Acrylate Oligomers.” ACS Sustain. Chem. Eng., 3 (7) 1313–1320 (2015)CrossRef

13.

Lomonaco, D, Santiago, GMP, Ferreira, YS, Arriaga, ÂMC, Mazzetto, SE, Mele, G, Vasapollo, G, “Study of Technical CNSL and Its Main Components as New Green Larvicides.” Green Chem., 11 (1) 31–33 (2009)CrossRef

14.

Voirin, C, Caillol, S, Sadavarte, NV, Tawade, BV, Boutevin, B, Wadgaonkar, PP, “Functionalization of Cardanol: Towards Biobased Polymers and Additives.” Polym. Chem., 5 (9) 3142–3162 (2014)CrossRef

15.

Bai, W, Xiao, X, Chen, Q, Xu, Y, Zheng, S, Lin, J, “Synthesis and Characterization of Cross-Linked Polymer from Cardanol by Solvent-Free Grinding Polymerization.” Prog. Org. Coat., 75 (3) 184–189 (2012)CrossRef

16.

Bloise, E, Becerra-Herrera, M, Mele, G, Sayago, A, Carbone, L, D’Accolti, L, Mazzetto, SE, Vasapollo, G, “Sustainable Preparation of Cardanol-Based Nanocarriers with Embedded Natural Phenolic Compounds.” ACS Sustain. Chem. Eng., 2 (5) 1299–1304 (2014)CrossRef

17.

Uslu, A, Yeşilot, S, “Chiral Configurations in Cyclophosphazene Chemistry.” Coord. Chem. Rev., 291 (48) 28–67 (2015)CrossRef

18.

Liu, R, Zhu, G, Li, Z, Liu, X, Chen, Z, Ariyasivam, S, “Cardanol-Based Oligomers with “Hard Core, Flexible Shell” Structures: from Synthesis to UV Curing Applications.” Green Chem., 17 (6) 3319–3325 (2015)CrossRef

19.

Köhler, J, Kühl, S, Keul, H, Möller, M, Pich, A, “Synthesis and Characterization of Polyamine-Based Cyclophosphazene Hybrid Microspheres.” J. Polym. Sci. Part A Polym. Chem., 52 (4) 527–536 (2014)CrossRef

20.

Tian, Z, Chen, C, Allcock, HR, “New Mixed-Substituent Fluorophosphazene High Polymers and Small Molecule Cyclophosphazene Models: Synthesis, Characterization, and Structure Property Correlations.” Macromolecules, 48 (5) 1483–1492 (2015)CrossRef

21.

Shan, X, Song, L, Xing, W, Hu, Y, Lo, S, “Effect of Nickel-Containing Layered Double Hydroxides and Cyclophosphazene Compound on the Thermal Stability and Flame Retardancy of Poly (Lactic Acid).” Ind. Eng. Chem. Res., 51 (40) 13037–13045 (2012)CrossRef

22.

Austin, PE, Riding, GH, Allcock, HR, “Improved Method for the Synthesis of Poly(Organophosphazenes) and Hindered Cyclophosphazenes.” Macromolecules, 16 (5) 719–722 (1983)CrossRef

23.

Beşli, S, Coles, SJ, Davies, DB, Erkovan, AO, Hursthouse, MB, Kılıç, A, “Stable P–N Bridged Cyclophosphazenes with a Spiro or Ansa Arrangement.” Inorg. Chem., 47 (12) 5042–5044 (2008)CrossRef

24.

Muralidharan, K, Omotowa, BA, Twamley, B, Piekarski, C, “High Energy Density Materials from Azido Cyclophosphazenes.” Chem. Commun., 37 (41) 5193 (2005)CrossRef

25.

Davies, DB, Clayton, TA, Eaton, RE, Shaw, RA, Egan, A, Hursthouse, MB, Sykara, GD, Porwolik-Czomperlik, I, Siwy, M, Brandt, K, “Chiral Configurations of Cyclophosphazenes.” J. Am. Chem. Soc., 122 (50) 12447–12457 (2000)CrossRef

26.

Kumar, D, Singh, N, Elias, AJ, Malik, P, Allen, CW, “Reactions of Alkyne-and Butadiyne-Derived Fluorinated Cyclophosphazenes with Diiron and Dimolybdenum Carbonyls.” Inorg. Chem., 53 (19) 10674–10684 (2014)CrossRef

27.

Zlatanić, A, Lava, C, Zhang, W, Petrović, ZS, “Effect of Structure on Properties of Polyols and Polyurethanes Based on Different Vegetable Oils.” J. Polym. Sci. Part B Polym. Phys., 42 (5) 809–819 (2004)CrossRef

28.

Watanabe, H, Fujimoto, A, Takahara, A, “Manipulation of Surface Properties: The Use of Nanomembrane as a Nanometre-Thick Decal.” Soft Matter, 7 (5) 1856–1860 (2011)CrossRef

29.

Sileika, TS, Barrett, DG, Zhang, R, Lau, KHA, Messersmith, PB, “Colorless Multifunctional Coatings Inspired by Polyphenols Found in Tea, Chocolate, and Wine.” Angew. Chem. Int. Edit., 52 (41) 10766–10770 (2013)CrossRef

30.

Sung, C, Hearn, K, Reid, DK, Vidyasagar, A, Lutkenhaus, JL, “A Comparison of Thermal Transitions in Dip- and Spray-Assisted Layer-by-Layer Assemblies.” Langmuir, 29 (28) 8907–8913 (2013)CrossRef

31.

Gao, R, Hu, L, Chen, M, Wu, L, “Controllable Fabrication and Photoelectrochemical Property of Multilayer Tantalum Nitride Hollow Sphere-Nanofilms.” Small, 10 (15) 3038–3044 (2014)CrossRef

32.

Callow, JA, Callow, ME, “Trends in the Development of Environmentally Friendly Fouling-Resistant Marine Coatings.” Nat. Commun., 2 244 (2011)CrossRef

Title: Synthesis and properties of UV-curable cardanol-based acrylate oligomers with cyclotriphosphazene core
Authors: Yan Yuan
Miao Chen
Qiaohua Zhou
Ren Liu
Publication date: 08-08-2018
Publisher: Springer US
Published in: Journal of Coatings Technology and Research / Issue 1/2019
Print ISSN: 1547-0091
Electronic ISSN: 1935-3804
DOI: https://doi.org/10.1007/s11998-018-0112-1

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