Synthesis of a novel UV-curable prepolymer hexanediol diglycidyl ether diacrylate and its cured film tensile property

Abstract

A novel UV-curable prepolymer hexanediol diglycidyl ether diacrylate (HDGEA) was synthesized by utilizing hexanediol diglycidyl ether (HDGE) and acrylic acid (AA) as starting materials, N, N-dimethylbenzylamine as catalyst and p-hydroxyanisole as inhibitor. The optimal synthetic conditions were that the concentration of N, N-dimethylbenzylamine was 0.80 wt% of reactants, the concentration of p-hydroxyanisole was 0.3 wt% of reactants, the reaction temperature was 90–110 °C, and the molar ratio of HDGE to AA was 1: 2.2. Meanwhile, 1-hydroxycyclohexyl phenyl ketone of a UV-curing initiator was added to the synthesized HDGEA to prepare a kind of UV-curing coating. The mechanical properties of the UV-cured films were determined, giving 31.87 MPa of tensile strength, 871.88 MPa of Young’s modulus and 6.77% of elongation at tear.

Keywords

hexanediol diglycidyl ether diacrylate / synthesis / acrylic acid / UV-curable prepolymer / film

References

[1] Shirai M. Reworkable UV Curing Materials[J]. Prog. Org. Coat, 2007, 58: 158-165.

[2] sangermano M., lak N., Malucelli G., . UV-curing and Characterization of Polymer-clay Nanocoatings by Dispersion of Acrylate-funtionalized Organoclays[J]. Prog. Org. Coat, 2008, 61: 89-94.

[3] Dietliker K., Crivello J. V. Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints[M], 1991 London SITA Technology Ltd. 1-9.

[4] Davidson R. S. Exploring the Science Technology and Application of UV and EB Curing[M], 1999 London SITA Technology Ltd. 5-12.

[5] Takimoto Y. Radiation Curing in Polymer Science and Technology[M], 1993 London Elsevier 26-29.

[6] Decker C., Moussa K. Kinetic Study of Light-induced Polymerization by Real-time UV and IR Spectroscopy[J]. J. Polym. Sci., Polym. Chem., 1993, 30(5): 913-928.

[7] Pappas S. P. UV-curing Science and Technology[M], 1992 New York Plenum Press 64-71.

[8] Crivello J. V., Ortiz R. A. Synthesis of Epoxy Monomers that Undergo Synergistic Photopolymerization by A Radical- induced Cationic Mechanism[J]. J. Polym. Chem., 2001, 39(20): 3 578-3 592.

[9] Decker C., Thi Viet T. N., Thi H. P. Photoinitiated Cationic Polymerization of Epoxides[J]. Polym. Int., 2001, 50(9): 986-997.

[10] Kumar V., Bhardwaj Y. K., Goel N. K., . Coating Characteristics of Electron Beam Cured Bisphenol A Diglycidyl Ether Diacrylate-co-aliphatic Urethane Diacrylate Resins[J]. Surf Coat Technol., 2008, 202(21): 5 202-5 209.

[11] Park Y.-J., Lim D.-H., Kim H.-J., . UV- and Thermal-curing Behaviors of Dual-curable Adhesives Based on Epoxy Acrylate Oligomers[J]. Int. J. Adhes., 2009, 29: 710-717.

[12] Crivello J. V., Ortiz R. A. Design and Synthesis of Highly Reactive Photopolymerizable Epoxy Monomers[J]. J. Polym. Sci. Polym. Chem., 2001, 39(14): 2 385-2 395.

[13] Sangermano M., Malucelli G., Morel F., . Cationic Photopolymerization of Vinyl Ether Systems[J]. Eur. Polym. J., 1999, 35(4): 639-645.

[14] Decker C., Bianchi C., Decker D., . Photoinitiated Polymerization of Vinyl Ether-based Systems[J]. Prog. Org. Coat, 2001, 42(3): 253-266.

[15] Zheng Y. C., Wei W. J., Chen F. Study on Synthesis and UV-curing Behaviors of ADGDE[J]. Thermosetting Resin, 2003, 18(1): 14-17.

[16] Wei W. J., Zheng Y. C., Lu G. Synthesis and Characteristics of Acrylate Epoxy Oligomer Used for Light-curing[J]. Chemical World, 2002, 12: 638-640.

[17] Huang B. W., Huang B. F., Du G. P., . Synthesis of a Novel UV-curable Prepolymer Polypropyleneglycol Diglycidyl Ether Diacrylate[J]. Journal of Wuhan University of Technology- Mater. Sci.Ed., 2008, 23(4): 495-498.

[18] Sperling L. H., Mishra V. Polymer Materials Encyclopedia[M], 1996 New York CRC Press 3 252-3 276.

[19] ASTM D882-91. The Method for Tensile Properties of Thin Plastic Sheeting[S]. Agencies of the Department of Defense, 1993