Abstract
The diacrylate reactive diluent was synthesized by reacting glycidyl methacrylate, piperazine, and cyclic ethylene chlorophosphate. The synthesized reactive diluent was utilized to formulate UV-curable wood coating. The weight fractions of reactive diluent were varied from 0 to 25% in coating formulation with constant photoinitiator concentration. The molecular structure of reactive flame retardant was evaluated by FTIR, mass spectroscopy, 31PNMR, and 1HNMR spectral analysis. The flame retardant behaviors of the cured film were evaluated from limiting oxygen index and UL-94 vertical burning test. Thermal stability was estimated from thermogravimetric analysis and differential scanning calorimetry. The effects of varying concentrations of reactive diluent on the viscosity of the formulation along with optical, mechanical, and chemical resistance properties of coatings were evaluated. The gel content, water absorption behavior, and stain resistance of coatings were also studied.
Similar content being viewed by others
References
Saxena, NK, Gupta, DR, “Development and Evaluation of Fire Retardant Coatings.” Fire Technol., 26 329–341 (1990)
Ravey, M, Pearce, EM, “Flexible Polyurethane Foam. I Thermal Decomposition of a Polyether-based, Water-Blown Commercial Type of Flexible Polyurethane Foam.” J. Appl. Polymer Sci., 63 47–74 (1997)
Sivriev, C, Abski, ZL, “Flame Retarded Rigid Polyurethane Foams by Chemical Modification with Phosphorus- and Nitrogen-Containing Polyols.” Eur. Polymer J., 30 509–514 (1994)
Guo, WJ, “Flame-Retardant Modification of UV-Curable Resins with Monomers Containing Bromine and Phosphorus.” J. Polymer Sci. Polymer Chem., 30 819–827 (1992)
Haim, D, Moshe, GA, “Reactive Flame Retardant as a Poly(propylene)-Sized Glass Adhesion Promoter.” Macromol. Mater. Eng., 291 913–916 (2006)
Luijk, P, Govers, HAJ, Eijkel, GB, Boon, JJ, “Thermal Degradation Characteristics of High Impact Polystyrene/Decabromodiphenylether/Antimony Oxide Studied by Derivative Thermogravimetry and Temperature Resolved Pyrolysis-Mass Spectrometry: Formation of Polybrominated Dibenzofurans, Antimony (Oxy) Bromides and Brominated Styrene Oligomers.” J. Anal. Appl. Pyrolysis, 20 303–319 (1991)
Gu, J, Dang, J, Y, Wu, Xie, C, Han, Y, “Flame-Retardant, Thermal, Mechanical and Dielectric Properties of Structural Non-Halogenated Epoxy Resin Composites.” Polymer-Plast. Technol. Eng., 51 1198–1203 (2012)
Gu, J, Zhang, G-C, Dong, S-L, Zhang, Q-Y, Kong, J, “Study on Preparation and fire-Retardant Mechanism Analysis of Intumescent Flame-Retardant Coatings.” Surf. Coat. Technol., 201 7835–7841 (2007)
Laoutid, F, Bonnaud, L, Alexandre, M, Lopez-Cuesta, JM, Dubois, PH, “New Prospects in Flame Retardant Polymer Materials: From Fundamentals to Nanocomposites.” Mater. Sci. Eng. R., 63 100–125 (2009)
Chen-Yang, YW, Chuang, JR, Yang, YC, Li, CY, Chiu, YS, “New UV-Curable Cyclotriphosphazenes as Fire-Retardant Coating Materials for Wood.” J. Appl. Polymer Sci., 69 115–122 (1998)
Randoux, T, Vanovervelt, JC, Van den Bergen, T, Camino, G, “Halogen-Free Flame Retardant Radiation Curable Coatings.” Prog. Org. Coat., 45 281–289 (2002)
Granzow, A, “Flame Retardation by Phosphorus Compounds.” Acc. Chem. Res., 11 177–183 (1978)
Zeytuncu, B, Kahraman, V, Yucel, O, “Synthesis and Characterization of Flame Retarding UV-Curable Boron Containing Hybrid Coatings”. Supplemental Proceedings. The Minerals M Materials Science. Wiley, pp. 613–617 2011
Yuan, H, Xing, W, Zhang, P, Song, L, Hu, Y, “Functionalization of Cotton with UV Cured Flame Retardant Coatings.” Ind. Eng. Chem. Res., 51 5394–5401 (2012)
Cheng, XE, Shi, W, “Synthesis and Thermal Properties of Silicon-Containing Epoxy Resin Used for UV-Curable Flame-Retardant Coatings.” J. Thermal Anal. Calorim., 103 303–310 (2011)
Maiti, S, Banerjee, S, Palit, SK, “Phosphorus-Containing Polymers.” Prog. Polymer Sci., 18 227–261 (1993)
Bakos, D, Kosik, M, Antos, K, Karolyova, M, Vyskocil, I, “The Role of Nitrogen in Nitrogen–Phosphorus Synergism.” Fire Mater., 6 10–12 (1982)
Pandya, HB, Bhagwat, MM, “Mechanistic Aspects of Phosphorus–Nitrogen Synergism in Cotton Flame Retardancy.” Text. Res. J., 51 5–8 (1981)
Zubkova, NS, Kachalina, TA, Tyuganova, MA, “Phosphorus–Nitrogen Synergism for Polycaproamide Materials.” Fibre Chem., 24 450–452 (1993)
Liu, YL, Hsiue, GH, Chiu, YS, Jeng, R, Perng, LH, “Phosphorus-Containing Epoxy for Flame Retardant I. Synthesis, Thermal, and Flame-Retardant Properties.” J. Appl. Polymer Sci., 61 613–621 (1996)
Hsiue, GH, Liu, YL, Tsiao, J, “Phosphorus-Containing Epoxy Resins for Flame Retardancy V: Synergistic Effect of Phosphorus-Silicon on Flame Retardancy.” J. Appl. Polymer Sci., 78 1–7 (2000)
Shieh, JY, Wang, CS, “Synthesis of Novel Flame Retardant Epoxy Hardeners and Properties of Cured Products.” Polymer, 42 7617–7625 (2001)
Li, Q, Jiang, P, Wei, P, “Synthesis, Characteristic, and Application of New Flame Retardant Containing Phosphorus, Nitrogen, and Silicon.” Polymer Eng. Sci., 46 344–350 (2006)
Dumler, R, Thoma, H, “Thermal Formation of Polybrominated Dibenzodioxins (PBDB) and Dibenzofurans (PBDF) from Bromine Containing Flame Retardants.” Chemosphere, 19 305–308 (1989)
Huang, ZG, Shi, WF, “UV Curing Behaviour of Hyperbranched Polyphosphate Acrylate/Di(hydroxylpropyl Methacrylate) Piperazine and Properties of the Cured Film.” Prog. Org. Coat., 59 312–317 (2007)
Chen, X, Hu, Y, Jiao, C, Song, L, “Thermal and UV-Curing Behavior of Phosphate Diacrylate Used for Flame Retardant Coatings.” Prog. Org. Coat., 59 318–323 (2007)
Chao, P, Li, Y, Gu, X, Han, D, Jia, X, Wang, M, Zhoub, T, Wang, T, “Novel Phosphorus–Nitrogen–Silicon Flame Retardants and Their Application in Cycloaliphatic Epoxy Systems.” Polymer Chem., 6 2977–2985 (2015)
Zhu, SW, Shi, WF, “Flame Retardance of UV Cured Epoxy Acrylate Blended with Different States of Phosphated Methacrylate.” Polymer Degrad. Stab., 82 435–439 (2003)
Ansari, BWH, Noori, S, Naqvi, AZ, “Interaction Between Zwitterionic Surfactants and Amphiphilic Drug: A Tensiometric Study.” Z. Phys. Chem., 227 441–458 (2013)
Chen, Xilei, Jiao, Chuanmei, “Thermal Degradation Characteristics of a Novel Flame Retardant Coating Using TG-IR Technique.” Polymer Degrad. Stab., 93 2222–2225 (2008)
Chen-Yang, YW, Lee, HF, Yuan, CY, “Flame-Retardant Phosphate and Cyclotriphosphazene-Containing Epoxy Resin: Synthesis and Properties.” Journal of polymer science: Part A: Polymer chemistry., 38 972–981 (2000)
Manfredi, LB, Fraga, AN, Vazquez, A, “Influence of the Network Structure and Void Content on Hygrothermal Stability of Resol Resin Modified with Epoxy-Amine.” J. Appl. Polymer Sci., 102 588–597 (2006)
Saijun, D, Nakason, C, Kaesaman, A, Klinpituksa, P, “Water Absorption and Mechanical Properties of Water-Swellable Natural Rubber.” Songkl. J. Sci. Technol., 31 561–565 (2009)
Huang, ZG, Shi, WF, “Synthesis and Properties of a Novel Hyperbranched Polyphosphate Acrylate Applied to UV Curable Flame Retardant Coatings.” Eur. Polymer J., 43 1302–1312 (2007)
Tathe, DS, Jagtap, RN, “Synthesis of Bio-based Polyurethane from Modified Prosopis juliflora Oil.” J. Am. Oil Chem. Soc., 90 1405–1413 (2013)
Cheng, X-E, Wenfang, S, “UV-Curing Behavior and Properties of Tri/di(acryloyloxyethyloxy) Phenyl Silane Used for Flame-Retardant Coatings.” Prog. Org. Coat., 69 252–259 (2010)
Gu, J, Guo, Y, Lv, Z, Geng, W, Zhang, Q, “Highly Thermally Conductive POSS-g-SiCp/UHMWPE Composites with Excellent Dielectric Properties and Thermal Stabilities.” Composites: Part A, 78 95–101 (2015)
Li, M, Zhong, Y, Wang, Z, Fischer, A, Ranft, F, Drummer, D, Wu, W, “Flame Retarding Mechanism of Polyamide 6 with Phosphorus–Nitrogen Flame Retardant and DOPO Derivatives.” J. Appl. Polymer Sci., (2016). doi:10.1002/APP.42932
Acknowledgments
The authors immensely like to thank UGC SAP-Green Tech Grant for providing the financial support and Institute of chemical technology for allowing us to do our research and Mr. Sunil S. Daddikar (Director, Unique UV & Light PVT. Ltd., Vasai. Mumbai) for providing UV curing facility.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lokhande, G., Chambhare, S. & Jagtap, R. Synthesis and properties of phosphate-based diacrylate reactive diluent applied to UV-curable flame-retardant wood coating. J Coat Technol Res 14, 255–266 (2017). https://doi.org/10.1007/s11998-016-9849-6
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11998-016-9849-6