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A new class of acrylated alkyds

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Abstract

A new class of acrylated alkyds resins has been developed using a modern controlled polymerization approach. The reactive relationship between acrylics and alkyds has been defined by difficulty and an inability to propagate to form suitable grafting during a free-radical-based process. A living free-radical process was employed to provide control of both location and blocks of monomers which were attached to the polyester backbone of the alkyd. Both acrylic monomers and blocks of different monomer were successfully polymerized with control. Although there was some side reaction at the pendent fatty acid unsaturation, overall, the system was well behaved with respect to control of blocks of sequential monomers and living characteristics of the free-radical polymerization. Demonstration of concept was achieved in both high solids and waterborne systems. Representative coating properties are also reported for model alkyd systems.

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References

  1. Wicks, Z, Jr, Jones, F, Pappas, SP, Organic Coatings Science and Technology, Vol. 2, p. 630. John Wiley and Sons, New York (1999)

    Google Scholar 

  2. Karandikar, VC, “Hybrid Polymers for High Performance Coatings.” Paintindia, 2 55–74 (2006)

    Google Scholar 

  3. Wang, ST, Schork, FJ, Poehlein, GW, Gooch, JW, “Emulsion and Miniemulsion Copolymerization of Acrylic Monomers in the Presence of Alkyd Resin.” J. Appl. Polym. Sci., 12 2069–2076 (1996)

    Article  Google Scholar 

  4. Nabuurs, T, Baijards, RA, German, AL, “Alkyd–Acrylic Hybrid Systems for Use as Binders in Waterborne Paints.” Prog. Org. Coat., 1–4 163–172 (1996)

    Article  Google Scholar 

  5. Wu, XQ, Schork, FJ, Gooch, JW, “Hybrid Miniemulsion Polymerization of Acrylic/Alkyd Systems and Characterization of the Resulting Polymers.” J. Polym. Sci., Part A: Polym. Chem., 22 4159–4168 (1999)

    Article  ADS  Google Scholar 

  6. Shoaf, GL, Stockl, RR, “Alkyd/Acrylic Hybrid Latexes with Enhanced Oxidative Curing.” Polym. React. Eng., 3 319–334 (2003)

    Article  CAS  Google Scholar 

  7. Tsavalas, JG, Luo, Y, Schork, FJ, “Grafting Mechanisms in Hybrid Miniemulsion Polymerization.” J. Appl. Polym. Sci., 11 1825–1836 (2003)

    Article  CAS  Google Scholar 

  8. Wang, C, Lin, G, Pae, J, Jones, FN, Ye, H, Shen, W, “Novel Synthesis of Carboxy-Functional Soybean Alkyd Resins for Water-Reducible Coatings.” J. Coat. Technol., 904 55–61 (2000)

    Article  Google Scholar 

  9. Hudda, L, Tsavalas, JG, Schork, FJ, “Simulation Studies on the Origin of the Limiting Conversion Phenomenon in Hybrid Miniemulsion Polymerization.” Polymer, 4 993–1001 (2005)

    Article  CAS  Google Scholar 

  10. Tsavalas, JG, Gooch, JW, Schork, FJ, “Water-Based Crosslinkable Coatings via Miniemulsion Polymerization of Acrylic Monomers in the Presence of Unsaturated Polyester Resin.” J. Appl. Polym. Sci., 7 916–927 (2000)

    Article  Google Scholar 

  11. Tsavalas, JG, Luo, Y, Hudda, L, Schork, FJ, “Limiting Conversion Phenomenon in Hybrid Miniemulsion Polymerization.” Polym. React. Eng., 3 277–304 (2003)

    Article  CAS  Google Scholar 

  12. Schork, FJ, Dong, H, Gooch, JW, Sinangil, MS, Tsavalas, JG, Wu, X, “Graft Copolymers for Water-Borne Coatings Applications via Hybrid Miniemulsion Polymerization.” DECHEMA Monographien 1998, 6th International Workshop on Polymer Reaction Engineering, pp. 355–363, 1998

  13. Schork, FJ, Tsavalas, J, “The Morphology of Alkyd/Acrylate Latexes Produced via Hybrid Miniemulsion Polymerization: Grafting Mechanisms.” Prog. Colloid Polym. Sci., 126–130 (2004)

  14. Shim, J, Park, D, Kim, H, “Synthesis and Evaluation of Water-Reducible Acrylic–Alkyd Resins with High Hydrolytic Stability.” Proceedings of the International Waterborne, High-Solids, and Powder Coatings Symposium, pp. 159–167, 1997

  15. Moad, G, Rizzardo, E, Thang, SH, “Living Radical Polymerization by the RAFT Process.” Aust. J. Chem., 6 379–410 (2005)

    Article  Google Scholar 

  16. Jagur-Grodzinski, J, Living and Controlled Polymerization: Synthesis, Characterization and Properties of the Respective Polymers and Copolymers, Vol. 1, p. 385. Nova Science Publishers, Inc., New York (2006)

    Google Scholar 

  17. Lai, JT, Filla, D, Shea, R, “Functional Polymers from Novel Carboxyl-Terminated Trithiocarbonates as Highly Efficient RAFT Agents.” Macromolecules, 18 6754–6756 (2002)

    Article  ADS  CAS  Google Scholar 

  18. Lai, JT, Shea, R, “Controlled Radical Polymerization by Carboxyl- and Hydroxyl-Terminated Dithiocarbamates and Xanthates.” J. Polym. Sci. Part A, 14 4298–4316 (2006)

    Article  CAS  Google Scholar 

  19. Zhang, Z, Zhu, X, Zhu, J, Cheng, Z, “Thermal Polymerization of Methyl(meth)acrylate via Reversible Addition-Fragmentation Chain Transfer (RAFT) Process.” Polymer, 20 6970–6977 (2006)

    Article  CAS  Google Scholar 

  20. Gao, J, Luo, Y, Wang, R, Li, B, Zhu, S, “Kinetics of Methyl Methacrylate and n-Butyl Acrylate Copolymerization Mediated by 2-Cyanoprop-2-yl dithiobenzoate as a RAFT Agent.” J. Polym. Sci. Part A, 14 3098–3111 (2007)

    Article  CAS  Google Scholar 

  21. Fan, D, He, J, Xu, J, Tang, W, Liu, Y, Yang, Y, “Synthesis of SAN-Containing Block Copolymers Using RAFT Polymerization.” J. Polym. Sci. Part A, 7 2260–2269 (2006)

    Article  CAS  Google Scholar 

  22. Krasia, TC, Patrickios, CS, “Amphiphilic Polymethacrylate Model Co-Networks: Synthesis by RAFT Radical Polymerization and Characterization of the Swelling Behavior.” Macromolecules, 7 2467–2473 (2006)

    Article  ADS  CAS  Google Scholar 

  23. Peklak, AD, Butte, A, Storti, G, Morbidelli, M, “Gel Effect in the Bulk Reversible Addition-Fragmentation Chain Transfer Polymerization of Methyl Methacrylate: Modeling and Experiments.” J. Polym. Sci. Part A, 3 1071–1085 (2006)

    Article  CAS  Google Scholar 

  24. Mellon, V, Rinaldi, D, Bourgeat-Lami, E, D’Agosto, F, “Block Copolymers of γ-Methacryloxypropyltrimethoxysilane and Methyl Methacrylate by RAFT Polymerization. A New Class of Polymeric Precursors for the Sol–Gel Process.” Macromolecules, 5 1591–1598 (2005)

    Article  ADS  CAS  Google Scholar 

  25. dos Santos, AM, Pohn, J, Lansalot, M, D’Agosto, F, “Combining Steric and Electrostatic Stabilization Using Hydrophilic MacroRAFT Agents in Ab Initio Emulsion Polymerization of Styrene.” Macromol. Rapid Commun., 12 1325–1332 (2007)

    Article  CAS  Google Scholar 

  26. Lowe, AB, Torres, M, Wang, R, “A Doubly Responsive Diblock Copolymer AB: RAFT Synthesis and Aqueous Solution Properties of Poly (N-isopropylacrylamide-block-4-vinylbenzoic acid).” J. Polym. Sci. Part A, 24 5864–5871 (2007)

    Article  CAS  Google Scholar 

  27. Cuervo-Rodriguez, R, Bordege, V, Sanchez-Chaves, M, Fernandez-Garcia, M, “Free-Radical Copolymerization of Ethyl α-Hydroxymethylacrylate with Methyl Methacrylate by Reversible Addition-Fragmentation Chain Transfer.” J. Polym. Sci. Part A, 19 5618–5629 (2006)

    Article  CAS  Google Scholar 

  28. Luo, Y, Liu, B, Wang, Z, Gao, J, Li, B, “Butyl Acrylate RAFT Polymerization in Miniemulsion.” J. Polym. Sci. Part A, 11 2304–2315 (2007)

    Article  CAS  Google Scholar 

  29. He, L, Read, ES, Armes, SP, Adams, DJ, “Direct Synthesis of Controlled-Structure Primary Amine-Based Methacrylic Polymers by Living Radical Polymerization.” Macromolecules (Washington, DC, United States), 13 4429–4438 (2007)

    ADS  Google Scholar 

  30. Guo, T, Tang, D, Song, M, Zhang, B, “Copolymerizations of Butyl Methacrylate and Fluorinated Methacrylates via RAFT Miniemulsion Polymerization.” J. Polym. Sci. Part A, 22 5067–5075 (2007)

    Article  CAS  Google Scholar 

  31. Nejad, EH, Castignolles, P, Gilbert, RG, Guillaneuf, Y, “Synthesis of Methacrylate Derivatives Oligomers by Dithiobenzoate-RAFT-Mediated Polymerization.” J. Polym. Sci. Part A, 6 2277–2289 (2008)

    Article  CAS  Google Scholar 

  32. Perrier, S, Barner-Kowollik, C, Quinn, JF, Vana, P, Davis, TP, “The Origin of Inhibition Effects in the Reversible Addition Fragmentation Chain Transfer Polymerization of Methyl Acrylate.” Macromolecules, 22 8300–8306 (2002)

    Article  ADS  CAS  Google Scholar 

  33. Moad, G, Chiefari, J, Chong, YK, Krstina, J, Mayadunne, RTA, Postma, A, Rizzardo, E, Thang, SH, “Living Free Radical Polymerization with Reversible Addition-Fragmentation Chain Transfer (The Life of RAFT).” Polym. Int., 9 993–1001 (2000)

    Article  Google Scholar 

  34. Prescott, SW, Ballard, MJ, Rizzardo, E, Gilbert, RG, “RAFT in Emulsion Polymerization: What Makes it Different?” Aust. J. Chem., 6 & 7 415–424 (2002)

    Article  Google Scholar 

  35. Patton, DL, Advincula, RC, “A Versatile Synthetic Route to Macromonomers via RAFT Polymerization.” Macromolecules, 25 8674–8683 (2006)

    Article  ADS  CAS  Google Scholar 

  36. Gemici, H, Legge, TM, Whittaker, M, Monteiro, MJ, Perrier, S, “Original Approach to Multiblock Copolymers via Reversible Addition-Fragmentation Chain Transfer Polymerization.” J. Polym. Sci. Part A, 11 2334–2340 (2007)

    Article  CAS  Google Scholar 

  37. Lopez, RG, Boisson, C, D’Agosto, F, Spitz, R, Boisson, F, Gigmes, D, Bertin, D, “New Functional Polyolefins: Towards a Bridge Between Catalytic and RAFT Polymerizations?” Macromol. Rapid Commun., 3 173–181 (2006)

    Article  CAS  Google Scholar 

  38. Boyer, C, Bulmus, V, Liu, J, Davis, TP, Stenzel, MH, Barner-Kowollik, C, “Well-Defined Protein−Polymer Conjugates via In Situ RAFT Polymerization.” J. Am. Chem. Soc., 22 7145–7154 (2007)

    Article  CAS  Google Scholar 

  39. Dziczkowski, J, “Advances in Acrylic-Alkyd Hybrid Synthesis and Characterization,” Doctoral Dissertation, The University of Akron (2008). Retrieved from http://drc.ohiolink.edu/handle/2374.OX/103718

  40. Tsvetkova, B, Tencheva, J, Peikov, P, “Esterification of 7-Theophyllineacetic Acid with Diethylene Glycol Monomethyl Ether.” Acta Pharm. (Zagreb, Croatia), 2 251–257 (2006)

    Google Scholar 

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Acknowledgments

The authors would like to express their gratitude to P&G for their financial support of this research. We wish to thank The Goodyear Corporation for donation of the NMR instrument in this study. Special thanks are warranted to the Mass Spectrometry Center at the University of Akron for their assistance with SEC.

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  1. Department of Polymer Engineering, University of Akron, Akron, OH, 44325, USA

    Jamie Dziczkowski & Mark D. Soucek

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  1. Jamie Dziczkowski
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Correspondence to Mark D. Soucek.

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Dziczkowski, J., Soucek, M.D. A new class of acrylated alkyds. J Coat Technol Res 7, 587–602 (2010). https://doi.org/10.1007/s11998-009-9237-6

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