Skip to main content

Advertisement

Log in

Preparation and characterization of water-based polyurethane–acrylic hybrid nanocomposite emulsion based on a new silane-containing acrylic macromonomer

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. LeBaron, PC, Wang, Z, Pinnavaia, TJ, “Polymer-Layered Silicate Nanocomposites: On Overview.” J. Appl. Clay. Sci., 15 11–29 (1999)

    Article  CAS  Google Scholar 

  2. Plueddemann, EP, Silane Coupling Agents. Plenum Press, New York, 1982

    Google Scholar 

  3. Plueddemann, EP, In: Ishida, H, Kumar, J (eds.) Molecular Characterization of Composite Interfaces, p. 13. Plenum Press, New York, 1985

  4. 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)

    Article  CAS  Google Scholar 

  5. 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)

    Article  CAS  Google Scholar 

  6. 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)

    Article  CAS  Google Scholar 

  7. Kim, BK, Seo, JW, Jeong, HM, “Morphology and Properties of Waterborne Polyurethane/Clay Nanocomposites.” Eur. Polym. J., 39 85–91 (2003)

    Article  CAS  Google Scholar 

  8. Chen, TK, Tien, YI, Wei, KH, “Synthesis and Characterization of Novel Segmented Polyurethane/Clay Nanocomposites.” Polymer, 41 1345–1353 (2000)

    Article  CAS  Google Scholar 

  9. 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)

    Article  Google Scholar 

  10. 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)

    Article  CAS  Google Scholar 

  11. Ogawa, M, Miyoshi, M, Kuroda, K, “Perfluoroalkylsilylation of the Interlayer Silanol Groups of a Layered Silicate, Magadiite.” Chem. Mater., 10 3787–3789 (1998)

    Article  CAS  Google Scholar 

  12. 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)

    Article  CAS  Google Scholar 

  13. 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)

    Article  CAS  Google Scholar 

  14. Oertel, G (ed.) Polyurethane Handbook, 3rd ed., Vol. 7. Munich: Hanser Publishers, 1993

  15. 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)

    Article  CAS  Google Scholar 

  16. Kim, DS, Kim, JT, Woo, WB, “Reaction Kinetics and Characteristics of Polyurethane/Clay Nanocomposites.” J. Appl. Polym. Sci., 96 1641–1647 (2005)

    Article  CAS  Google Scholar 

  17. 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)

    Article  CAS  Google Scholar 

  18. Goda, H, Frank, CW, “Fluorescence Studies of the Hybrid Composite of Segmented-Polyurethane and Silica.” Chem. Mater., 13 2783–2787 (2001)

    Article  CAS  Google Scholar 

  19. 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)

    Article  CAS  Google Scholar 

  20. Ma, J, Zhang, S, Qi, Z, “Synthesis and Characterization of Elastomeric Polyurethane/Clay Nanocomposites.” J. Appl. Polym. Sci., 82 1444–1448 (2001)

    Article  CAS  Google Scholar 

  21. 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)

    Article  CAS  Google Scholar 

  22. 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)

    Article  CAS  Google Scholar 

  23. 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)

    Article  CAS  Google Scholar 

  24. 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)

    Article  CAS  Google Scholar 

  25. Kyriacos, D, GEM-Chem, E-mail: dk@GEM-Chem.net

  26. 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)

    Article  CAS  Google Scholar 

  27. Lambourne, R, Paint and Surface Coatings Theory and Practice. Horwood, E. (ed.) Market Cross House, Chichester, West Sussex, 1987

  28. Moghbeli, MR, Tolue, S, “Acrylonitrile/Styrene/Acrylate Structural Rubber Latex Particles as Impact Modifier for SAN Copolymer.” Iranian Polym. J., 20 137–146 (2011)

    CAS  Google Scholar 

  29. 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)

    Article  CAS  Google Scholar 

  30. 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)

    Article  Google Scholar 

  31. 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)

    Article  CAS  Google Scholar 

  32. 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)

    Article  CAS  Google Scholar 

  33. 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)

    Article  Google Scholar 

  34. Okamoto, Y, Hasegawa, Y, Yoshino, F, “Urethane/Acrylic Composite Polymer Emulsions.” Prog. Org. Coat., 29 175–182 (1996)

    Article  CAS  Google Scholar 

  35. 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)

    Article  CAS  Google Scholar 

  36. 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)

    Article  CAS  Google Scholar 

  37. 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)

    Article  CAS  Google Scholar 

  38. Tien, YI, Wei, KH, “High-Tensile-Property Layered Silicates/Polyurethane Nanocomposites by Using Reactive Silicates as Pseudo-Chain Extenders.” Macromolecules, 34 9045–9052 (2001)

    Article  CAS  Google Scholar 

  39. Choi, WJ, Kim, SH, Kim, YJ, Kim, SC, “Synthesis of Chain-Extended Organifier and Properties of Polyurethane/Clay Nanocomposites.” Polymer, 45 6045–6057 (2004)

    Article  CAS  Google Scholar 

  40. 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)

    Article  Google Scholar 

  41. 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)

    Article  CAS  Google Scholar 

  42. 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)

    Article  Google Scholar 

  43. 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)

    Article  Google Scholar 

  44. Xu, J, Shi, W, Pang, W, “Synthesis and Shape Memory Effects of Si–O–Si Cross-Linked Hybrid Polyurethanes.” Polymer, 47 457–465 (2006)

    Article  CAS  Google Scholar 

  45. 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)

    Article  CAS  Google Scholar 

  46. 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)

    Article  CAS  Google Scholar 

  47. 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)

    CAS  Google Scholar 

  48. 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)

    CAS  Google Scholar 

  49. Naghash, JH, Mallakpour, S, Mokhtarian, N, “Synthesis and Characterization of Silicone-Modified Vinyl Acetate–Acrylic Emulsion Copolymers.” Prog. Org. Coat., 55 375–381 (2006)

    Article  CAS  Google Scholar 

  50. 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)

    CAS  Google Scholar 

  51. 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)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hamid Javaheriannaghash.

Rights and permissions

Reprints 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

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-011-9373-7

Keywords

Navigation