Abstract
A new silane-containing acrylic macromonomer, maleimidedoethoxybutoxydimethylsiloxy butyl acrylate (MEBDMSBA), based on maleic anhydride (MA), ethanolamine (EA), 1,4-butanediol (BDO), dichlorodimethylsilane (DCDMS), and acrylic acid (AA) has been synthesized for formulation of waterborne polyurethane (WPU). Also a series of new silane-containing WPU, methyl methacrylate (MMA), MEBDMSBA, and montmorillonite (MMT) with organically modified montmorillonite (OMMT) content (1.25 wt%) hybrid nanocomposites have been successfully prepared by the emulsion polymerization in the presence of a WPU dispersion, using ammonium peroxodisulfate (APS) as an initiator. The WPU dispersion has been synthesized by a polyaddition reaction of isophorone diisocyanate (IPDI) on polypropylene glycol (PPG-1000) and dimethylol propionic acid (DMPA) as chain extender. The monomer was characterized by Fourier transformer infrared spectroscopy (FTIR), elemental analysis, proton (1H NMR), and carbon (13C NMR) nuclear magnetic resonance spectroscopes, respectively. The nanocomposite emulsions were also characterized using Fourier transform infrared spectroscopy (FTIR) and laser light scattering. Thermal properties of the copolymers were studied using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The OMMT was characterized by FTIR and X-ray diffraction (XRD). The morphology of copolymers was investigated by scanning electron microscopy (SEM) and transition electron microscopy (TEM), and then the effects of silane concentrations on the water absorption ratio were examined. Results showed that OMMT could improve the properties of emulsion; in other words, the properties of nanocomposite emulsion were better when compared with those of the silane–acrylate emulsion.
Similar content being viewed by others
References
LeBaron, PC, Wang, Z, Pinnavaia, TJ, “Polymer-Layered Silicate Nanocomposites: On Overview.” J. Appl. Clay. Sci., 15 11–29 (1999)
Plueddemann, EP, Silane Coupling Agents. Plenum Press, New York, 1982
Plueddemann, EP, In: Ishida, H, Kumar, J (eds.) Molecular Characterization of Composite Interfaces, p. 13. Plenum Press, New York, 1985
Kim, JT, Lee, DY, Oh, TS, Lee, DH, “Characteristics of Nitrile-Butadiene Rubber Layered Silicate Nanocomposites with Silane Coupling Agent.” J. Appl. Polym. Sci., 89 2633–2640 (2003)
Hwang, JJ, Liu, HJ, “Influence of Organophilic Clay on the Morphology, Plasticizer-Maintaining Ability, Dimensional Stability, and Electrochemical Properties of Gel Polyacrylonitrile (PAN) Nanocomposite Electrolytes.” Macromolecules, 35 7314–7319 (2002)
Subramani, S, Lee, JM, Kim, JH, Cheong, IW, “One-Pack Cross-Linkable Waterborne Methyl Ethyl Ketoxime-Blocked Polyurethane/Clay Nanocomposite Dispersions.” Macromol. Res., 13 418–426 (2005)
Kim, BK, Seo, JW, Jeong, HM, “Morphology and Properties of Waterborne Polyurethane/Clay Nanocomposites.” Eur. Polym. J., 39 85–91 (2003)
Chen, TK, Tien, YI, Wei, KH, “Synthesis and Characterization of Novel Segmented Polyurethane/Clay Nanocomposites.” Polymer, 41 1345–1353 (2000)
Yanagisawa, T, Kuroda, K, Kato, C, “Organic Derivatives of Layered Polysilicates. II. Reaction of Magadiite and Kenyaite with Diphenylmethylchlorosilane.” Bull. Chem. Soc. Jpn., 61 3743–3745 (1998)
Ogawa, M, Okutomo, S, Kuroda, K, “Control of Interlayer Microstructures of a Layered Silicate by Surface Modification with Organochlorosilanes.” J. Am. Chem. Soc., 120 7361–7362 (1998)
Ogawa, M, Miyoshi, M, Kuroda, K, “Perfluoroalkylsilylation of the Interlayer Silanol Groups of a Layered Silicate, Magadiite.” Chem. Mater., 10 3787–3789 (1998)
Lee, S, Kim, J, “Surface Modification of Clay and its Effect on the Intercalation Behavior of the Polymer/Clay Nanocomposites.” J. Polym. Sci. Part B Polym. Phys., 42 2367–2372 (2004)
Herrera, NN, Letoffe, JM, Putaux, JL, David, L, Elodie, BL, “Aqueous Dispersions of Silane-Functionalized Laponite Clay Platelets. A First Step Towards the Elaboration of Water-Based Polymer/Clay Nanocomposites.” Langmuir, 20 1564–1571 (2004)
Oertel, G (ed.) Polyurethane Handbook, 3rd ed., Vol. 7. Munich: Hanser Publishers, 1993
Gorrasi, G, Tortora, M, Vittoria, V, “Synthesis and Physical Properties of Layered Silicates/Polyurethane Nanocomposites.” J. Polym. Sci. Part B Polym. Phys., 43 2454–2467 (2005)
Kim, DS, Kim, JT, Woo, WB, “Reaction Kinetics and Characteristics of Polyurethane/Clay Nanocomposites.” J. Appl. Polym. Sci., 96 1641–1647 (2005)
Solarski, S, Benali, S, Rochery, M, Devaux, E, Alexandre, M, Monteverde, F, “Synthesis of a Polyurethane/Clay Nanocomposite Used as Coating: Interactions Between the Counterions of Clay and the Isocyanate and Incidence on the Nanocomposite Structure.” J. Appl. Polym. Sci., 95 238–244 (2005)
Goda, H, Frank, CW, “Fluorescence Studies of the Hybrid Composite of Segmented-Polyurethane and Silica.” Chem. Mater., 13 2783–2787 (2001)
Tortora, M, Gorrasi, G, Vittoria, V, Galli, G, Ritrovati, S, Chiellini, E, “Structural Characterization and Transport Properties of Organically Modified Montmorillonite/Polyurethane Nanocomposites.” Polymer, 43 6147–6157 (2002)
Ma, J, Zhang, S, Qi, Z, “Synthesis and Characterization of Elastomeric Polyurethane/Clay Nanocomposites.” J. Appl. Polym. Sci., 82 1444–1448 (2001)
Subramani, S, Lee, JY, Cheong, IW, Kim, JH, “Crosslinked Aqueous Dispersion of Silylated Poly(Urethane–Urea)/Clay Nanocomposites.” Comp. Sci. Technol., 67 1561–1573 (2007)
Kim, ST, Kim, JB, Chung, CM, Ahn, KD, “Polymerization of N-(tert-Butyldimethylsilyloxy)maleimide and Applications of the Polymers as Resist Materials.” J. Appl. Polym. Sci., 66 2507–2516 (1997)
Lee, HT, Lin, LH, “Waterborne Polyurethane/Clay Nanocomposites: Novel Effects of the Clay and its Interlayer Ions on the Morphology and Physical and Electrical Properties.” Macromolecules, 39 6133–6141 (2006)
Feng, X, Zhong, A, Chen, D, “Preparation and Properties of Poly (silicone-co-acrylate)/Montmorillonite Nanocomposite Emulsion.” J. Appl. Polym. Sci., 101 3963–3970 (2006)
Kyriacos, D, GEM-Chem, E-mail: dk@GEM-Chem.net
Shaffie, A, Moustafa, AB, Mohamed, ES, Badran, AS, “The Course of Emulsion Polymerization of Vinyl Acetate using Redox Systems of different Oxidizing Agents.” J. Polym. Sci. Part A: Polym. Chem., 35 3141–3149 (1997)
Lambourne, R, Paint and Surface Coatings Theory and Practice. Horwood, E. (ed.) Market Cross House, Chichester, West Sussex, 1987
Moghbeli, MR, Tolue, S, “Acrylonitrile/Styrene/Acrylate Structural Rubber Latex Particles as Impact Modifier for SAN Copolymer.” Iranian Polym. J., 20 137–146 (2011)
Zhang, Y, Jin, Q, Zhao, J, Wu, C, Fan, Q, Wu, Q, “Facile Fabrication of pH-Sensitive Core–Shell Nanoparticles Based on HEC and PMAA via Template Polymerization.” Eur. Polym. J., 46 1425–1435 (2010)
Van den Brand, J, Blajiev, O, Beentjes, PCJ, Terryn, H, de Wit, JHW, “Interaction of Anhydride and Carboxylic Acid Compounds with Aluminum Oxide Surfaces Studied Using Infrared Reflection Absorption Spectroscopy.” Langmuir, 20 6308–6317 (2004)
Fedrizzi, L, Bianchi, A, Deflorian, F, Rossi, S, Bonora, PL, “Effect of Chemical Cleaning on the Corrosion Behaviour of Painted Aluminium Alloys.” Electrochim. Acta, 47 2159–2168 (2002)
Soer, WJ, Ming, W, Klumperman, B, Koning, C, Benthem, R, “Surfactant-Free Artificial Latexes from Modified Styrene–Maleic Anhydride (SMA) Copolymers.” Polymer, 47 7621–7627 (2006)
Shao-ming, F, Li-ming, Z, Li-jun, G, Dong-liang, L, Hai-bo, Z, ‘‘Preparation and Characterization of Nanocomposite Material Based on Polyurethane Acrylate Macromonomer.’’ Polym. Compos., 30 731–736 (2009)
Okamoto, Y, Hasegawa, Y, Yoshino, F, “Urethane/Acrylic Composite Polymer Emulsions.” Prog. Org. Coat., 29 175–182 (1996)
Naghash, JH, Abili, B, “Synthesis of a Silicone Containing Allylic Monomer and Its Uses in the Waterborne Polyurethane/Vinyl Acetate–Acrylic Hybrid Emulsion Copolymers.” Prog. Org. Coat., 69 486–494 (2010)
Acharya, H, Pramanik, M, Srivastava, S, Bhowmick, A, “Synthesis and Evaluation of High-Performance Ethylene–Propylene–Diene Terpolymer/Organoclay Nanoscale Composites.” J. Appl. Polym. Sci., 93 2429–2436 (2004)
Sadhu, S, Bhowmick, AK, “Preparation and Properties of Styrene-Butadiene Rubber Based Nanocomposites: The Influence of the Structural and Processing Parameters.” J. Appl. Polym. Sci., 92 698–709 (2004)
Tien, YI, Wei, KH, “High-Tensile-Property Layered Silicates/Polyurethane Nanocomposites by Using Reactive Silicates as Pseudo-Chain Extenders.” Macromolecules, 34 9045–9052 (2001)
Choi, WJ, Kim, SH, Kim, YJ, Kim, SC, “Synthesis of Chain-Extended Organifier and Properties of Polyurethane/Clay Nanocomposites.” Polymer, 45 6045–6057 (2004)
Kishore, K, Jena, K, Raju, KVSN, “Synthesis and Characterization of Hyperbranched Polyurethane–Urea/Silica Based Hybrid Coatings.” Ind. Eng. Chem. Res., 46 6408–6416 (2007)
Jiang, H, Zheng, Z, Song, W, Li, Z, Wang, X, “Alkoxysilane Functionalized Polyurethane/Polysiloxane Copolymers: Synthesis and the Effect of End-Capping Agent.” Polym. Bull., 59 53–63 (2007)
Crandi, S, Magistris, A, Mustarelli, P, Quartarone, E, Tomasi, C, Meda, L, “Synthesis and Characterization of SiO2–PEG Hybrid Materials.” J. Non-Cryst. Solids, 352 273–280 (2006)
Gabriela, B, Martina, M, Ana Maria, M, Jean-Michel, W, “Ternary Interpenetrating Networks of Polyurethane–Poly(methyl methacrylate)–Silica: Preparation by the Sol–Gel Process and Characterization of Films.” Eur. Polym. J., 42 2977–2986 (2006)
Xu, J, Shi, W, Pang, W, “Synthesis and Shape Memory Effects of Si–O–Si Cross-Linked Hybrid Polyurethanes.” Polymer, 47 457–465 (2006)
Zhang, L, Zeng, Z, Yang, J, Chen, Y, “Characterization and Properties of UV-Curable Polyurethane-Acrylate/Silica Hybrid Materials Prepared by the Sol–Gel Process.” Polym. Int., 53 1431–1435 (2004)
Naghash, JH, Karimzadeh, A, Massah, AR, “Synthesis and Properties of Styrene–Butylacrylate Emulsion Copolymers Modified by Silane Compounds.” J. Appl. Polym. Sci., 112 1037–1044 (2009)
Naghash, JH, Mallakpour, S, Forushani, YP, Uyanik, N, “A Study on Emulsion Copolymerization of α,ω-Diacrylate Poly(dimethylsiloxane) Containing Vinyl Ester of Versatic Acid/Vinyl Acetate.” Polymer (Korea), 32 95–102 (2008)
Naghash, JH, Karimzadeh, A, Momeni, AR, Massah, AR, Alian, H, “Preparation and Properties of Triethoxyvinylsilane-Modified Styrene-Butyl Acrylate Emulsion Copolymers.” Turk. J. Chem., 31 257–269 (2007)
Naghash, JH, Mallakpour, S, Mokhtarian, N, “Synthesis and Characterization of Silicone-Modified Vinyl Acetate–Acrylic Emulsion Copolymers.” Prog. Org. Coat., 55 375–381 (2006)
Naghash, JH, Mallakpour, S, Kayhan, N, “Synthesis and Characterization of Silicone Modified Acrylic Resin and Its Uses in the Emulsion Paints.” Iranian Polym. J., 14 211–222 (2005)
Qiang, R, Bibiao, J, Dongliang, Z, Qiang, Y, Jianbo, F, Yang, Y, Jianhai, C, “Studies on the Atom Transfer Radical Polymerization of a Maleimide AB* Monomer and Modification of the Halogen End Groups.” Eur. Polym. J., 41 2742–2752 (2005)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Javaheriannaghash, H., Ghazavi, N. Preparation and characterization of water-based polyurethane–acrylic hybrid nanocomposite emulsion based on a new silane-containing acrylic macromonomer. J Coat Technol Res 9, 323–336 (2012). https://doi.org/10.1007/s11998-011-9373-7
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11998-011-9373-7