Abstract
A series of UV-curable isophorone diisocyanate-based poly(ester-urethane)methacrylate (IPEUMA) oligomers were synthesized by a two-step polymerization process. The amount of isophorone diisocyanate was varied during the synthesis. The effects of NCO:OH ratio and HEMA on the structural and physicochemical properties of UV-cured IPEUMAs were investigated. As the NCO:OH ratio increased, the tensile strength and thermal stability increased, whereas the elongation and hydrolytic degradation of the film decreased. The higher strength and thermal stability for higher NCO:OH ratio may be due to the increase in intermolecular hydrogen bonding in the UV-cured film. UV-cured IPEUMA films also show excellent chemical and solvent resistance.
Similar content being viewed by others
References
Dzunuzovic, E, Tasic, S, Bozic, B, Babic, D, Dunjic, B, “UV-Curable Hyperbranched Urethane Acrylate Oligomers Containing Soybean Fatty Acids.” Prog. Org. Coat., 52 (2) 136–143 (2005)
Jian, Z, Yong, H, Ming, X, Jun, N, “Preparation and Properties of Dual-Cure Polyurethane Acrylate.” Prog. Org. Coat., 66 (1) 35–39 (2009)
Yong, H, Zhou, M, Wu, B, Jian, Z, Jun, N, “Synthesis and Properties of Novel Polyurethane Acrylate Containing 3(2-Hydroxyethyl) Isocyanurate Segment.” Prog. Org. Coat., 67 (3) 264–268 (2010)
Gloeckner, P, Jung, T, Struck, S, Studer, K, Radiation Curing: Coatings and Printing Inks, Technical Basics, Applications and Trouble Shooting. Hannover, Vincentz Network, 2008
Wang, X, Soucek, M, “Investigation of Non-isocyanate Urethane Dimethacrylate Reactive Diluents for UV-Curable Polyurethane Coatings.” Prog. Org. Coat., 76 (7) 1057–1067 (2013)
Srivastava, A, Agarwal, D, Mistry, S, Singh, J, “UV Curable Polyurethane Acrylate Coatings for Metal Surfaces.” Pigment Resin Technol., 37 (4) 217–223 (2008)
Koleske, JV, Radiation Curing of Coatings. ASTM International, West Conshohocken, PA, 2002
Rengasamy, S, Mannari, V, “Development of Soy-Based UV-Curable Acrylate Oligomers and Study of Their Film Properties.” Prog. Org. Coat., 76 (1) 78–85 (2013)
Dzunuzovic, ES, Tasic, SV, Bozic, BR, Dzunuzovic, JV, Dunjica, BM, Jeremica, KB, “Mechanical and Thermal Properties of UV Cured Mixtures of Linear and Hyperbranched Urethane Acrylates.” Prog. Org. Coat., 74 (1) 158–164 (2012)
Shi, R, Zhang, X, Dai, J, “Synthesis of TDI-Polyurethane/Polyacrylate Composite Emulsion by Solvent-Free Method and Performances of the Latex Film.” J. Macromol. Sci. Part A, 50 (3) 350–357 (2013)
Meledyn, M, Paszkiewicz, R, Masiulanis, B, “Synthesis and Properties of UV-Curable Poly(imide-urethane) Acrylates.” J. Appl. Polym. Sci., 91 (2) 971–980 (2004)
Hwang, HD, Kim, HJ, “Enhanced Thermal and Surface Properties of Waterborne UV-Curable Polycarbonate-Based Polyurethane (Meth)acrylate Dispersion by Incorporation of Polydimethylsiloxane.” React. Funct. Polym., 71 (6) 655–665 (2011)
Bai, C, Zhang, X, Jiabing, JD, “Synthesis and Characterization of a New UV Cross-Linkable Waterborne Siloxane-Polyurethane Dispersion.” J. Macromol. Sci. Part A: Pure Appl. Chem., 44 (11) 1203–1208 (2007)
Xu, J, Rong, X, Chi, T, Wang, M, Wang, Y, Dongya, Y, Qiu, F, “Preparation, Characterization of UV-Curable Waterborne Polyurethane Acrylate and the Application in Metal Iron Surface Protection.” J. Appl. Polym. Sci., 130 (5) 3142–3152 (2013)
Seo, Jongchul, Jang, ES, Song, JH, Choi, S, Khan, SB, Han, H, “Preparation and Properties of Poly(urethane-acrylate) Films for Ultraviolet-Curable Coatings.” J. Appl. Polym. Sci., 118 (4) 2454–2460 (2010)
Umare, SS, Chandure, AS, “Synthesis, Characterization and Biodegradation Studies of Poly(ester-Urethanes)s.” Chem. Eng. J., 142 (1) 65–77 (2008)
Bhusari, GS, Umare, SS, Chandure, AS, “Synthesis, Characterization and Biodegradation Studies of Poly(ester-urethanes)s.” Emerg. Mater. Res., 3 (2) 91–100 (2013)
Wang, F, Hu, JQ, Tu, WP, “Study on Microstructure of UV-Curable Polyurethane Acrylate Films.” Prog. Org. Coat., 62 (3) 245–250 (2008)
Yoo, H, Lee, Y, Kwon, J, Kim, H, “Comparison of the Properties of UV-Cured Polyurethane Acrylates Containing Different Diisocyanates and Low Molecular Weight Diols.” Fiber Polym., 2 (3) 122–128 (2001)
Flory, PJ, “Statistical Mechanics of Swelling of Network Structures.” J. Chem. Phys., 18 (1) 108–111 (1950)
Bristow, GM, Watson, WF, “Cohesive Energy Densities of Polymers. Part 1. Cohesive Energy Densities of Rubbers by Swelling Measurements.” Trans. Faraday. Soc., 54 1731 (1958)
Brandrup, J, Immergent, EH, Polymer Handbook. Wiley Interscience, New York, 1967
Xu, H, Qiu, F, Wang, Y, Wu, W, Yang, D, Guo, Q, “UV-Curable Waterborne Polyurethane-Acrylate: Preparation, Characterization and Properties.” Prog. Org. Coat., 73 (1) 47–53 (2013)
Mondal, S, Martin, D, “Hydrolytic Degradation of Segmented Polyurethane Copolymers for Biomedical Applications.” Polym. Degrad. Stab., 97 (8) 1553–1561 (2012)
Deka, H, Karak, N, “Bio-Based Hyperbranched Polyurethanes for Surface Coating Applications.” Prog. Org. Coat., 66 (3) 192–198 (2009)
Barlkani, M, Hepburn, C, “Determination of Crosslink Density by Swelling in the Castable Polyurethane Elastomer Based on 1/4-Cyclohexane Diisocyanate and para-Phenylene Diisocyanate.” Iranian J. Polym. Sci. Technol., 1 1–5 (1992)
Cunha, F, Melo, D, Veronese, V, Forte, M, “Study of Castor Oil Polyurethane-Poly(methyl methacrylate) Semi-Interpenetrating Polymer Network (SIPN) Reaction Parameters Using a 23 Factorial Experimental Design.” Mater. Res., 7 (4) 539–543 (2004)
Peruzzo, PJ, Anbinder, PS, Pardini, OR, Carlos, CA, Leite, CA, Galembeck, F, Amalvy, JI, “Polyurethane/Acrylate Hybrids: Effects of the Acrylic Content and Thermal Treatment on the Polymer Properties.” J. Appl. Polym. Sci., 116 (5) 2694–2705 (2010)
Athawale, V, Kulkarni, M, “Preparation and Properties of Urethane/Acrylate Composite by Emulsion Polymerization Technique.” Prog. Org. Coat., 65 (3) 392–400 (2009)
Sultana, M, Mahmood, Zia, K, Bhatti, H, Jamil, T, Hussain, R, Zuber, M, “Modification of Cellulosic Fiber with Polyurethane Acrylate Copolymers. Part I: Physicochemical Properties.” Carbohydr. Polym., 87 (1) 397–404 (2012)
Huang, S, Lai, J, “Structure-Tensile Properties of Polyurethanes.” Eur. Polym. J., 33 (10) 1563–1567 (1997)
Kim, BK, Lee, KH, Kim, HD, “Preparation and Properties of UV-Curable Polyurethane Acrylates.” J. Appl. Polym. Sci., 60 (6) 799–805 (1996)
Xu, H, Qiu, F, Wang, Y, Yang, D, Wu, WZ, Chen, Z, “Preparation, Mechanical Properties of Waterborne Polyurethane and Crosslinked Polyurethane-Acrylate Composite.” J. Appl. Polym. Sci., 124 (2) 958–968 (2012)
Hojabri, L, Jose, J, Leao, AL, Bouzidi, L, Narine, S, “Synthesis and Physical Properties of Lipid-Based Poly(ester-urethane)s I: Effect of Varying Polyester Segment Length.” Polymer, 53 (17) 3762–3771 (2012)
Chattopadhayay, DK, Webster, DC, “Thermal Stability and Flame Retardancy of Polyurethanes.” Prog. Polym. Sci., 34 (10) 1068–1133 (2009)
Leung, LM, Koberstein, JT, “DSC Annealing Study of Microphase Separation and Multiple Endothermic Behaviors in Polyether-Based Polyurethane Block Copolymers.” Macromole., 19 (3) 706–713 (1986)
Oprea, S, “Synthesis and Characterization of Polyurethane Urea Acrylates: Effects of the Hard Segments Structure.” J. Appl. Polym. Sci., 105 (5) 509–2515 (2007)
Tale, NV, Jagtap, RN, Tathe, DS, “An Efficient Approach for the Synthesis of Thermoset Polyurethane Acrylate Polymer and its Film Properties.” Des. Monomers Polym., 17 (2) 147–155 (2014)
Corcuera, MA, Rueda, L, Fernandez d’Arlas, B, Arbelaiz, A, Marieta, C, Mondragon, I, Eceiza, A, “Microstructure and Properties of Polyurethanes Derived from Castor Oil.” Polym. Degrad. Stab., 95 (11) 2175–2184 (2010)
Hsieh, T, Hsieh, K, Simon, G, Tiu, C, “Interpenetrating Polymer Networks of 2-Hydroxyethyl Methacrylate Terminated Polyurethanes and Polyurethanes.” Polymer, 40 (11) 3153–3163 (1999)
Kim, Y, Kim, S, “Effect of Chemical Structure on the Biodegradation of Polyurethanes Under Composting Conditions.” Polym. Degrad. Stab., 62 (2) 343–352 (1998)
Hong, JH, Jeon, HJ, Yoo, JH, Yu, WR, Youk, JH, “Synthesis and Characterization of Biodegradable Poly(ε-caprolactone-co-butyrolactone)s Based Polyurethane.” Polym. Degrad. Stab., 92 (7) 1186–1192 (2007)
Ki, HC, Park, OO, “Synthesis, Characterization and Biodegradability of the Biodegradable Aliphatic–Aromatic Random co-Polyesters.” Polymer, 42 (5) 1849–1861 (2001)
Acknowledgments
One of the authors Ganesh S. Bhusari is thankful to the Director, VNIT, Nagpur (India) for awarding a research fellowship.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bhusari, G.S., Umare, S.S. & Chandure, A.S. Effects of NCO:OH ratio and HEMA on the physicochemical properties of photocurable poly(ester-urethane)methacrylates. J Coat Technol Res 12, 571–585 (2015). https://doi.org/10.1007/s11998-014-9635-2
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11998-014-9635-2