Skip to main content
Log in

Functional latex and thermoset latex films

  • Published:
JCT Research Aims and scope Submit manuscript

Abstract

We review advances in the design and development of functional latex particles that can be used to form crosslinked coatings. Our emphasis is on understanding fundamental principles, of the formation and aging of latex films, of crosslinking of polymer films, of the reaction mechanisms that lead to bond formation, and of the competition between bond formation and polymer diffusion in latex films. These principles form the basis for the design of modern coatings that combine high performance with environmental compliance.

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.

Similar content being viewed by others

References

  1. Bufkin, B.G. and Grawe, J.R., “Survey of the applications, Properties, and Technology of Crosslinking Emulsions: Part I,” Journal of Coatings Technology 50, No. 641, 41 (1978), (b) Grawe, J.R. and Bufkin, B.G., “Survey of the Applications, Properties, and Technology of Crosslinking Emulsions: Part II”, Journal of Coatings Technology 50, No. 643, 67 (1978); (c) Bufkin, B.G. and Grawe, J.R., “Survey of the Applications, Properties, and Technology of Crosslinking Emulsions: Part III”, Journal of Coatings Technology, 50, No. 644, 83 (1978); (d) Grawe, J.R. and Bufkin, B.G., “Survey of the Applications, Properties, and Technology of Crosslinking Emulsions: Part IV”, Journal of Coatings Technology, 50, No. 645, 70 (1978); (e) Bufkin, B.G. and Grawe, J.R., “Survey of the Applications, Properties, and Technology of Crosslinking Emulsions: Part V”, Journal of Coatings Technology, 50, No. 647, 65 (1978).

    CAS  Google Scholar 

  2. Gottlob, K., German Patent 254,672 (1912); (b) Gottlob, K., German Patent 255, 129 (1912).

  3. Luther, M. and Hueck, C. (to I.G. Farbenindustrie A.G.), Products of Latex Character and a Process for Producing the Same, U.S. Patent 1,864,078 (1931).

  4. Wicks, Z.W., Jr. Jones, F.N., and Pappas, S.P., “Film Formation, Components and Appearance,” Organic Coatings: Science and Technology, John Wiley and Sons, Inc., New York, pp. 83–119, 1992.

    Google Scholar 

  5. Lee, Do Ik, senior scientist Dow Chemical Co., Private communication 1999; (b) Thompson, S.J., The S/B Latex Story, Recollections of ‘Can Do’ at Dow, Dow Chemical Co. (1980).

  6. Watson, D., retired engineer, Rohm and Haas Co., Private communication, 1999.

  7. Miller, W., retired research scientist, UCAR Emulsion Systems, Union Carbide Corp., Private communication, 1999.

  8. Flory, P.J., Principles of Polymer Chemistry, Cornell University Press, London, pp. 359, 495–518, 1953.

    Google Scholar 

  9. Harkins, W.D., “A General Theory of the Mechanism of Emulsion Polymerization,” J. Am. Chem. Soc. 69, 1428–1444 (1947); (b) Smith, W.V. and Ewart, R.H., “Kinetics of Emulsion Polymerization,” J. Chem. Phys., 16 (6), 592–599 (1948).

    Article  CAS  Google Scholar 

  10. Dillion, R.E., Matheson, L.A., and Bradford, E.B., “Sintering of Synthetic Latex Particles,” J. Colloid Sci. 6, 108–117 (1951).

    Article  Google Scholar 

  11. Henson, W.A., Taber, D.A., and Bradford, E.B., Ind. Eng. Chem., 45, 735 (1953).

    Article  CAS  Google Scholar 

  12. Brown, G.L., “Formation of Films from Polymer Dispersions,” J. Polym. Sci., 22, 423–434 (1956).

    Article  CAS  Google Scholar 

  13. Vanderhoff, J.W., Tarkowski, H.L., Jenkins, M.C., and Bradford, E.B., “Theoretical Consideration of the Interfacial Forces Involved in the Coalescence of Latex Particles,” J. Macromol. Sci., Chem., 1(2), 361–397 (1966).

    CAS  Google Scholar 

  14. Sheetz, D.P., “Formation of Films by Drying of Latex,” J. Appl. Polym. Sci., 9, 3759–3773 (1965).

    Article  CAS  Google Scholar 

  15. Routh, A.F. and Russel, W.B., “Horizontal Drying Fronts in Evaporating Latex Films,” AICHE J., 44, 2088 (1998). (b) Routh, A.F. and Russel, W.B., “A Process Model for Altex Film Formation: Limiting Regmes for Individual Driving Forces,” Langmuir, 15 7762–7773 (1999).

    Article  CAS  Google Scholar 

  16. Voyutskii, S., Autohesion and Adhesion of High Polymers, Wiley-Interscience, New York, 1963.

    Google Scholar 

  17. Wang, Y., Kats, A., Juhué, D., Winnik, M.A., Shivers, R., and Dinsdale, C., “Freeze Fracture Studies of Latex Films Formed in the Absence and Presence of Surfactant,” Langmuir, 8, 1435–1442 (1992).

    Article  CAS  Google Scholar 

  18. Wang, Y., Juhué, D., Winnik, M.A., Leung, O.M., and Goh, M.C., “An Atomic Force Microscopy Study of Latex Film Formation,” Langmuir, 8, 760–762 (1992); (b) Goh, M.C., Juhué, D., Leung, O., Wang, Y., and Winnik, M.A., “Annealing Effects on the Surface Structure of Latex Films Studied by Atomic Force Microscopy,” Langmuir, 9, 1319–1322 (1993).

    Article  CAS  Google Scholar 

  19. Hahn, K., Ley, G., Schuller, H., and Oberthur, R., “On Particle Coalescence in Latex Films,” Colloid & Polym. Sci., 264, 1092–1096 (1986).

    Article  CAS  Google Scholar 

  20. Linné, M.A., Klein, A., Miller, G.A., and Sperling, L.H., “Film Formation from Latex: Hindered Initial Interdiffusion of Constrained Polystyrene Chains Characterized by Small-Angle Neutron Scattering,” J. Macromol. Sci., Phys., B27, 217–231 (1988); (b) Yoo, J.N., Sperling, L.H., Glinka, C.J., and Klein, A., “Characterization of Film Formation from Polystyrene Latex Particles via SANS. I. Moderate Molecular Weight,” Macromolecules, 23, 3962–3967 (1990).

    Article  Google Scholar 

  21. Zhao, C.L., Wang, Y., Hruska, Z., and Winnik, M.A., “Molecular Aspects of Latex Film Formation. An Energy Transfer Study,” Macromolecules, 23, 4082–4087 (1990).

    Article  CAS  Google Scholar 

  22. Rubinstein, M. and Colby, R., Polymer Physics, Oxford, New York, 2003.

    Google Scholar 

  23. Flory, P.J. and Rehner, J., “Statistical Mechanics of Crosslinked Polymer Networks,” Chem. Phys. 11, 521–526 (1943).

    Article  CAS  Google Scholar 

  24. Flory, P.J., “Statistical Mechanics of Swelling of Network Structures,” Chem. Phys., 18, 108–111 (1950).

    Article  CAS  Google Scholar 

  25. Mark, J.E. and Erman, B., Structure and Properties of Rubberlike Networks, Oxford University, 1995.

  26. Mark, J.E. and Erman, B., Rubberlike Elasticity: A Molecular Primer, Wiley-Interscience, 1988.

  27. Taylor, J.W. and Bassett D.R., in Technology of Waterborne Coatings, Glass, J.E. (Ed.), ACS Symposium Series 666, American Chemical Society, Washington, D.C., pp. 137–163 (1997).

    Google Scholar 

  28. Billingham, N.C., Molar Mass Measurements in Polymer Science, John Wiley and Sons Inc., New York, 1977.

    Google Scholar 

  29. Flory, P.J., “Molecular Size Distribution in Three-Dimensional Polymers. V. Post-Gelation Relationships,” J. Am. Chem. Soc., 62, 30–35 (1947).

    Article  Google Scholar 

  30. Reiser, A. and Pitts, E., “A Photographic Theory of Crosslinking Resins,” J. Photogr. Sci., 29, 187–191 (1981).

    CAS  Google Scholar 

  31. Reiser, A. and Pitts, E., “Characteristic Curve of Crosslinking Photoresists,” Photogr. Sci. and Eng. 20 (5), 225–229 (1976).

    CAS  Google Scholar 

  32. Miller, D.R. and Macosko, C.W., “Network Parameters for Crosslinking of Chains with Length and Site Distribution,” J. Polym. Sci: Part B: Polym. Phys., 26, 1–51 (1988).

    Article  CAS  Google Scholar 

  33. Bauer, D.R. and Budde, G.F., “Crosslinking Chemistry and Network Structure in High-Solids Acrylic-Melamine Coatings,” Ind. Eng. Chem, Prod. Res. Dev., 20, 674–679 (1981).

    Article  CAS  Google Scholar 

  34. Bauer, D.R. and Dickie, R.A., “Development and Application of Network Structure Models to Optimization of Bake Conditions for Thermoset Coatings,” Journal of Coatings Technology, 58, No. 738, 41 (1986).

    Google Scholar 

  35. Bauer, D.R., “How to Calculate Crosslink Structure in Coatings,” Journal of Coatings Technology, 60, No. 758, 53 (1988).

    CAS  Google Scholar 

  36. Joanicot, M., Wong, K., Maquet, J., Chevalier, Y., Pichot, C., Graillat, C., Lindner, P., Rios, L., and Cabane, B., “Ordering of Latex Particles During Film Formation,” Prog. Colloid Polym. Sci., 81, 175–183 (1990).

    Article  CAS  Google Scholar 

  37. Tzitzinou, A., Keddie, J.L., Guerts, J.M., Peters, A.C.I.A., and Satguru, R., “Film Formation of Latex Blends with Bimodal Size Distributions: Consideration of Particle Deformability and Continuity of the Dispersed Phase,” Macromolecules 33, 2695–2708 (2000).

    Article  CAS  Google Scholar 

  38. Roulstone, B.J., Wilkinson, M.C., Hearn, J., and Wilson, A.J., “Studies on Polymer Latex Films: I. A Study of Latex Film Morphology,” Polym. Int., 21, 87–94 (1991).

    Article  Google Scholar 

  39. Distler, D. and Kanig, G., “Fienstruktur von Polymeren aus Wässriger Dispersion,” Colloid Polym. Sci., 256, 1052–1060 (1978).

    Article  CAS  Google Scholar 

  40. Chevalier, Y., Pichot, C., Graillat, C., Joanicot, M., Wong, K., Maquet, J., Lindner, P., and Cabane, B., “Film Formation with Latex Particles,” Colloid Polym. Sci., 270, 806–821 (1992).

    Article  CAS  Google Scholar 

  41. Joanicot, M., Wong, K., Richard, J., Maquet, J., and Cabane, B., “Ripening of Cellular Films,” Macromolecules, 26, 3168–3175 (1993).

    Article  CAS  Google Scholar 

  42. Sperling, L.H., Klein, A., Sambasivam, M., and Kim, K.D., “Molecular Basis of Healing and Fracture at Polymer Interfaces,” Polym. Adv. Technol., 5, 453–472 (1993).

    Article  Google Scholar 

  43. Kim, K.D., Sperling, L.H., Klein, A., and Wignall, G.D., “Characterization of Film Formation from Direct Mini-Emulsified Polystyrene Latex Particles via SANS,” Macromolecules, 26, 4624–4631 (1993).

    Article  CAS  Google Scholar 

  44. Wool, R.P., Structure and Strength of Polymer Interfaces, Hanser Press, New York, 1995.

    Google Scholar 

  45. Mohammadi, N., Klein, A. and Sperling, L.H., “Polymer Chain Rupture and Fracture Behavior of Glassy Polystyrene. I,” Macromolecules, 26, 1019–1026 (1993).

    Article  CAS  Google Scholar 

  46. Kim, K.D., Sperling, L.H., Klein, A., and Hammouda, B., “Reptation Time, Temperature, and Cosurfactant Effects on the Molecular Interdiffusion Rate During Polystyrene Latex Film Formation,” Macromolecules, 27, 6841–6850 (1994).

    Article  CAS  Google Scholar 

  47. Sambasivam, M., Klein, A., and Sperling, L.H., “Energy-Consuming Micromechanisms in the Fracture of Glassy Polymers. 2: Effect of Molecular Weight on the Fracture of Polystyrene,” Macromolecules, 28, 152–159 (1995).

    Article  CAS  Google Scholar 

  48. Feng, J., Yekta, A., and Winnik, M.A., “Direct Non-Radiative Energy Transfer Across a Sharp Polymer Interface,” Chem. Phys. Lett., 260, 296–301 (1996).

    Article  Google Scholar 

  49. Liu, Y.S., Feng, J., and Winnik, M.A., “Study of Polymer Diffusion Across the Interface in Latex Films Through Direct Energy Transfer Experiments,” J. Chem. Phys., 101, 9096–9103 (1994).

    Article  CAS  Google Scholar 

  50. Farinha, J.P.S., Martinho, J.M.G., Yekta, A., and Winnik, M.A., “Direct Nonradiative Energy Transfer in Polymer Interphases: Fluorescence Decay Functions from Concentration Profiles Gen-erated by Fickian Diffusion,” Macromolecules, 28, 6084–6088 (1995).

    Article  CAS  Google Scholar 

  51. Boczar, E.M., Dionne, B.C., Fu, Z., Kirk, A.B., Lesko, P.M., and Koller, A.D., “Spectroscopic Studies of Polymer Interdiffusion During Film Formation,” Macromolecules, 26, 5772–5781 (1993).

    Article  CAS  Google Scholar 

  52. Wang, Y. and Winnik, M.A., “Energy Transfer Study of Polymer Diffusion in Melt-Pressed Films of Poly(methyl methacrylate),” Macromolecules, 26, 3147–3150 (1993).

    Article  CAS  Google Scholar 

  53. Winnik, M.A., Wang, Y., and Haley, F., “Latex Film Formation at the Molecular Level: The Effect of Coalescing Aids on Polymer Diffusion,” Journal of Coatings Technology, 64, No. 811, 51 (1992).

    CAS  Google Scholar 

  54. Juhué, D., Wang, Y., and Winnik, M.A., “Influence of a Coalescing Aid on Polymer Diffusion in Poly(butyl methacrylate) Latex Films,” Makromol. Chem., Rapid Commun., 14, 345–349 (1993).

    Article  Google Scholar 

  55. Kawaguchi, S., Odrobina, E., and Winnik, M.A., “Non-Ionic Surfactant Effects on Polymer Diffusion in Poly(n-butyl methacrylate) Latex Films,” Makromol. Chem., Rapid Commun., 16, 861–868 (1995).

    Article  CAS  Google Scholar 

  56. Feng, J., Pham, H., Stoeva, V., and Winnik, M.A., “Polymer Diffusion in Latex Films at Ambient Temperature,” J. Polym. Sci.: Part B: Polym. Phys., 36, 1129–1139 (1998).

    Article  CAS  Google Scholar 

  57. Kim, H.B. and Winnik, M.A., “Effect of Surface Acid Group Neutralization on Interdiffusion in Latex Films,” Macromolecules, 27, 1007–1012 (1994).

    Article  CAS  Google Scholar 

  58. Juhué, D. and Lang, J., “Film Formation from Dispersions of Core-Shell Latex Particles,” Macromolecules, 28, 1306–1308 (1995).

    Article  Google Scholar 

  59. Rharbi, Y., Boué, F., Joanicot, M., and Cabane, B., “Deformation of Cellular Polymeric Films,” Macromolecules, 29, 4346–4359 (1996).

    Article  Google Scholar 

  60. Kim, H.B. and Winnik, M.A., “Factors Affecting Interdiffusion Rates in Films Prepared from Latex Particles with a Surface Rich in Acid Groups and Their Salts,” Macromolecules, 28, 2033–2041 (1995).

    Article  CAS  Google Scholar 

  61. Taylor, J.W. and Klots, T., “Applied Approach to Film Formation: The Glass Temperature Evolution of Plasticized Latex Films,” Eur. Coat. J., 6, 38 (2002).

    Google Scholar 

  62. Taylor, J.W. and Klots, T., “An Applied Approach to Film Formation for Waterborne Coatings,” Proc. of the Twenty-Ninth International Waterborne, High-Solids, and Powder Coatings Symposium, New Orleans, LA, 181 (2002).

  63. Zosel, A. and Ley, G., “Influence of Crosslinking on Structure, Mechanical Properties, and Strength of Latex Films,” Macromolecules, 26, 2222–2227 (1993).

    Article  CAS  Google Scholar 

  64. Tamai, T., Pinenq, P., and Winnik, M.A., “Effect of Crosslinking on Polymer Diffusion in Poly(butyl methacrylate-co-butyl acrylate) Latex Forms,” Macromolecules, 32, 6102–6110 (1999).

    Article  CAS  Google Scholar 

  65. Winnik, M.A., “Interdiffusion and Crosslinking in Thermoset Latex Films,” Journal of Coatings Technology, 74, No. 925, 49 (2002).

    Google Scholar 

  66. Liu, R., Winnik, M.A., Di Stefano, F., and Venkatesan, J., “Interdiffusion vs. Crosslinking Rates in Isobutoxyacrylamide-Containing Latex Coatings,” Macromolecules, 34, 7306–7314 (2001).

    Article  CAS  Google Scholar 

  67. Aradian, A., Raphaël, E., and de Gennes, P.G., “Strengthening of a Polymer Interface: Interdiffusion and Crosslinking,” Macromolecules, 33, 9444–9451 (2000).

    Article  CAS  Google Scholar 

  68. Aradian, A., Raphaël, E., and de Gennes, P.G., “Interdiffusion and Crosslinking at Polymer Interfaces,” Macromolecules, 35, 4036–4043 (2002).

    Article  CAS  Google Scholar 

  69. Raphaël, E. and de Gennes, P.G., “Rubber-Rubber Adhesion with Connector Molecules,” J. Phys. Chem., 96, 4002–4007 (1992).

    Article  Google Scholar 

  70. Ahagon, A. and Gent, A., “Effect of Interfacial Bonding on the Strength of Adhesion,” J. Polym. Sci. Polym. Phys. Ed., 13, 1285–1300 (1995).

    Article  Google Scholar 

  71. Ji, H. and de Gennes, P.G., “Adhesion via Connector Molecules: The Many-Stitch Problem,” Macromolecules, 26, 520–525 (1993).

    Article  CAS  Google Scholar 

  72. Lake, G.J. and Thomas, A.G., “The Strength of Highly Elastic Materials,” Proc. R. Soc. London, Ser A., 300, 108–119 (1967).

    Article  CAS  Google Scholar 

  73. Taylor, J.W., Collins, M.J., and Clark, M.D., Waterborne Polymers Using Pendant Allyl Groups, U.S. Patent 5,539,073 (1996).

  74. Bassett, D.R. and Hamielec E.A., Emulsion Polymers and Emulsion Polymerization, ACS Symposium Series 165, American Chemical Society, Washington D.C., pp. 371–387 (1981).

    Google Scholar 

  75. Hoy, K.L., “Effect of Reaction Pathway on Emulsion Polymer Structure,” Journal of Coatings Technology, 51, No. 651, 27 (1979).

    CAS  Google Scholar 

  76. Feng, J., Odrobina, E., and Winnik, M.A., “Effect of Hard Polymer Filler Particles on Polymer Diffusion in a Low-Tg Latex Film,” Macromolecules, 31, 5290–5299 (1998); (b) Winnik, M.A. and Feng, J., “Latex Blends: An Approach to Zero-VOC Coatings,” Journal of Coatings Technology, 68, No. 852, 39 (1996).

    Article  CAS  Google Scholar 

  77. Eckersley, S.T. and Helmer, B.J., “Mechanistic Consideration of Particle Size Effects on Film Properties of Hard/Soft Latex Blends,” Journal of Coatings Technology, 69, No. 864, 97 (1997).

    CAS  Google Scholar 

  78. Winnik, M.A., Pinenq, P., Krüger, C., Zhang, J., and Yaneff, P.V., “Crosslinking vs. Interdiffusion Rates in Melamine-Formaldehyde Cured Latex Coatings: A Model for Waterborne Automotive Basecoat,” Journal of Coatings Technology, 71, No. 892, 47 (1999).

    CAS  Google Scholar 

  79. Bassett, D.R. and Sherwin, M.A., “Crosslinking Studies of Thermosetting Emulsion Polymers,” Waterborne and Higher Solids Coatings Symposium of the Southern Society of Coatings Technology, New Orleans, LA, February 1977.

  80. Hahn, K.G., Thermosetting Acrylic Latexes, U.S. Patent 4,812,491 (1989); (b) Kunz, B.L. and Hahn, K.G., Pigmented Low Cure Emulsion Polymers, U.S. Patent 4,981,883 (1991).

  81. Krishnan, S., Klein, A., El-Aasser, M.S., and Sudol, E.D., “Influence of a Chain Transfer Agent on the Crosslinking of Poly(n-butyl methacrylate-co-methylol Acrylamide) Latex Particles and Films,” Macromolecules, 36, 3511–3518 (2003).

    Article  CAS  Google Scholar 

  82. Rodgers, J.R., Organic Film Former Compositions of Self Sensitive Systems, U.S. Patent 3,308,078 (1965); (b) Rodgers, J.R., Coating Composition Comprising a Terpolymer, an Alkali Resin, and a Zirconyl-Fugitive Ligand Compound, U.S. Patent 3,320,196 (1965).

  83. Karsa, D.R., Additives for Water-Based Coatings, Royal Chemical Society, London, (1990); (b) Moles, P., MEL Chemical's Data Sheet 117 (2003).

    Google Scholar 

  84. “Polyfunctional Aziridines,” Cordova Chemical Co., Commercial Literature (1983).

  85. Trentini, M.C., Gerosa, P., and Carlson, V., “Formaldehyde-Free Waterborne Acrylic Wood Coatings,” Eur. Coat. J., 5, 362–367 (1995).

    Google Scholar 

  86. Nissihinbo Industries Literature (2002); (b) “Polycarbodiimide Crosslinkers,” Union Carbide Literature.

  87. Taylor, J.W., Monodispersed Multifunctional Carbodiimides, U.S. Patent 5,117,059 (1992); (b) Taylor, J.W., Emulsion and Crosslinkable Compositions Containing Polycarbodiimides, U.S. Patent 5,081,173 (1992); (c) Taylor, J.W., Surface Active Polycarbodiimides and Dispersions, U.S. Patent 5,047,588 (1991).

  88. Taylor, J.W., Surface Active Polycarbodiimides, U.S. Patent 4,820,863 (1989).

  89. Jacobs, J.M., Muijs, P.E., Steven van Es, J.G., and German, A.L.J., “Molecular Mass Control in Methacrylic Copolymer Latexes Containing Glycidyl Methacrylate,” Appl. Polym. Sci., 61, 9–19 (1996).

    Google Scholar 

  90. Taylor, J.W., Functional Latexes Resistant to Hydrolysis, International Patent Application (PCT), WO 17 698 A1 (1998); (b) Taylor, J.W., Functional Latexes Resistant to Hydrolysis, U.S. Patent 5,962,556 (1999).

  91. Tronc, F., Liu, R., Winnik, M.A., Eckersley, S.T., Rose, G.D., Weishun, J.M., and Meunier, D.M., “Epoxy-Functionalized, Low Glass-Transition Temperature Latex I. Synthesis, Characterization, and Polymer Interdiffusion,” J. Polym. Sci. Part A: Polym. Chem., 40, 2609–2625 (2002).

    Article  CAS  Google Scholar 

  92. Tronc, F., Chen, W., Winnik, M.A., Eckersley, S.T., Rose, G.D., Weishun, J.M., and Meunier, D.M., “Epoxy-Functionalized, Low Glass-Transition Temperature Latex II. Interdiffusion vs. Crosslinking in the Presence of a Diamine,” J. Polym. Sci. Part A: Polym. Chem., 40, 4098–4116 (2002).

    Article  CAS  Google Scholar 

  93. Nippon Shokubia Literature (1994).

  94. Murray, R.E., Eaton, R.F., Upshaw, T.A., Taylor, J.W., and Bassett, D.R., Process Utilizing Alkenyl Carboxylate Crosslinkers, U.S. Patent 5,412,038 (1995).

  95. Hubert, J.C., Venderbosch, R.A.M., Muizebelt, W.J., Klaasen, R.P., and Zabel, K.H., “Singlet Oxygen Drying of Alkyd Resins and Model Compounds,” Journal of Coatings Technology, 69, No. 869, 59 (1997); (b) Muizebelt, W.J., Donkerbroek, J.J., Nielen, M.W.F., Hussem, J.B., Biemond, M.E.F., Klaasen, R.P,, and Zabel, K.H., “Oxidative Crosslinking of Alkyd Resins Studied with Mass Spectrometry and NMR Using Model Compounds,” Journal of Coatings Technology, 70, No. 876, 83 (1998).

    CAS  Google Scholar 

  96. Tillson, H.C., Coating Compositions Comprising a Terpolymer of an Alkyl Acrylate, an Alkyl Methacrylate, and an Ester of a Unsaturated Alcohol with Methacrylic Acid, U.S. Patent 3,219,610 (1965).

  97. Heathley, F.H., Lovell, P.A., and McDonald, J., “NMR Studies of Free-Radical Polymerization and Copolymerization of Monomers and Polymers Containing Allyl Groups,” Eur. Polym. J., 29, No. 2/3, 255–268 (1993).

    Article  Google Scholar 

  98. Porter, N.A., Lehman, L.S., Weber, B.A., and Smith, K.J., “Unified Mechanism for Polyunsaturated Fatty Acid Autooxidation. Competition of Peroxy Radical Hydrogen Atom Abstraction, β-Scission, and Cyclization,” J. Am. Chem. Soc., 103, 6447–6455 (1981); (b) Porter, N.A. and Wujek, D.G., “Autooxidation of Polyunsaturated Fatty Acids, an Expanded Mechanistic Study,” J. Am. Chem. Soc., 106, 2626–2629 (1984); (c) Coyle, J.D., Introduction to Organic Photochemistry, John Wiley & Sons, Great Britain (1986).

    Article  CAS  Google Scholar 

  99. Brister, E.H., Smith, O.W., and Thames, S.F., “Castor Acrylated Monomer (CAM) in Vinyl-Acrylic Latexes,” Twenty-Sixth International Waterborne, High-Solids, and Powder Coatings Symposium, New Orleans, LA, 89 (1999); (b) King, C.L., Smith, O.W., and Thames, S.F., “Acrylic Properties Using CAM Monomer,” Proc. Twenty-Sixth International Waterborne, High-Solids, and Powder Coatings Symposium, New Orleans, LA, 100 (1999); (c) King, C.L., Smith, O.W., and Thames, S.F., “Oxidative Curing Profiles of CAM Based Acrylic Latexes,” Proc. Twenty-Seventh International Waterborne, High-Solids, and Powder Coatings Symposium, New Orleans, LA, 436 (2000); (d) King, C.L., Smith, O.W., and Thames, S.F., “Oxidative Curing Profiles of CAM Based Acrylic Latexes,”, Proc. Twenty-Eighth International Waterborne, High-Solids, and Powder Coatings Symposium, New Orleans, LA, 143 (2001); (e) Thames, S.F., Panjnani, K.G., and Fruchey, O.S., Latex Compositions Containing Ethylenically Unsaturated Esters of Long-Chain Alkenols, U.S. Patent 6,001,913 (1999); (f) Thames, S.F., Panjnani, K.G., and Fruchey, O.S., Latex Compositions Containing Ethylenically Unsaturated Esters of Fatty Acids and Applications Thereof, U.S. Patent 6,174,948 (2001); (g) Thames, S.F., Panjnani, K.G., Hariharan, R., and Wang, Z., Internally Plasticizing and Crosslinkable Monomers and Applications thereof, U.S. Patent 6,174,948 (2001).

  100. McGinniss, V.D., Seidewand, J.R., and Robert, J., Ultraviolet Curable Latexes, U.S. Patent, 4,107,013 (1978).

  101. Taylor, J.W., “A Study on the Chemistry of Alkylcarbodiimide Ethyl Methacrylates as Reactive Monomers for Acrylic and Vinyl Ester-based Latexes,” Proc. for XXIVth International Conference in Organic Coatings Science and Technology, Athens, Greece (1995); (b) Taylor, J.W., Collins, M.J., and Bassett, D.R., “A Study on the Chemistry of Alkylcarbodiimide Ethyl Methacrylates as Reactive Monomers for Acrylic and Vinyl Ester-based Latexes,” Prog. Org. Coat., 35, 215–221 (1999).

    Google Scholar 

  102. Padget, J.C., “Polymers for Water-Based Coatings—A Systematic Overview,” Journal of Coatings Technology, 66, No. 839, 89 (1994).

    CAS  Google Scholar 

  103. Mylonakis, S.G., Air Curable Latex, U.S. Patent 4,244,850 (1981).

  104. Wolfersberger, M.H., Schinder, F.J., Beckely, R.S., and Novak, R.W., Functionalized Multistage Polymers, U.S. Patent 5,306,744 (1994).

    Google Scholar 

  105. Bors, D.A., Air Curing Polymer Compositions, European Patent Application, 492 847 A2 (1991).

  106. Bors, D.A., Lavoie, A.C., and Emmons, W.D., Air Curing Compositions, U.S. Patent 5,484,849 (1996).

    Google Scholar 

  107. Pears, D.A. and Overbeek, G.C., Incorporation of Desired Groups into Polymer, the Polymer so Produced, and Composition Containing Them, European Patent Application, 442 653 A2 (1991).

  108. Taylor, J.W. and Collins, M.J., Waterborne Polymers with Pendant Crosslinkable Groups, International Patent Application (PCT), WO 32 424 A3 (1996).

  109. Del Rector, F., Blount, W.W., and Leonard, D.R., “Application of the Acetoacetyl Functionality in Thermoset Coatings,” Waterborne and Higher Solids Coatings Symposium, New Orleans, LA (1988).

  110. Geurink, P.A.J., van Dalen, L., van der Ven, L.G.J., and Lamping, R.R., “Analytical Aspects and Film Properties of Two-Pack Acetoacetate Functional Latexes,” Prog. Org. Coat., 27, 73–78 (1996).

    Article  Google Scholar 

  111. Feng, J., Pham, H., MacDonald, P., Winnik, M.A., Guerts, J., Zirkee, H., and van Es, S., German, A.L., “Formation and Cross-linking of Latex Films Through the Reaction of Acetoacetoxy Groups with Diamines Under Ambient Conditions,” Journal of Coatings Technology, 70, No. 881, 57 (1998); (b) Feng, J., “Molecular and Environmental Aspects of Latex Film Formation,” Ph.D. Thesis, University of Toronto, 1996.

    CAS  Google Scholar 

  112. Kyowa Hakko U.S.A., Literature bulletin DAA01 (1999).

  113. De Krom, A., Mulder, H., and Mestach, D., Wet Polymer on Nonabsorbing Substrates: Waterborne Acrylate Emulsions for Non-Absorbing Substates with Exceptional Removability, Farbe and Lack, 107, 97–105 (2001).

    Google Scholar 

  114. De Krom, A., Mulder, H., and Mestach, D., “New Developments in Waterborne Printing Inks for Non-Absorbing Substrates,” 6th Nurnburg Conference, 173–190 (2001).

  115. Buckmann, F., Overbeek, G.C., and Nabuurs, T., “Self-Crosslinking Surfactant Free Acrylic Dispersion for High Performance Coating Applications,” European Congress on Printing Inks, 701–708 (2001).

  116. Overbeek G.C. and Heuts M.P.J., Aqueous Coating Systems, U.S. Patent 4,988,762 (1991).

  117. Overbeek, G.C., Smak, W., Buckman, A.J.P., and Padget, J.C., Production of Aqueous Polymer Compositions, U.S. Patent, 5,859,112 (1999).

  118. Esser, R.J., Devona, J.E., Setzke, D.E., and Wagemans, L., “Waterbased Crosslinkable Surface Coatings,” Eur. Coat. J., 10, 732–733 (1998).

    Google Scholar 

  119. Taylor, J.W. and Collins, M.J., Stable Amino-Containing Polymer Latex Blends, U.S. Patent 5,998,543 (1999).

  120. Taylor, J.W. and Collins, M.J., Surfactant-Containing Acetoacetoxy-Functional and Enamine-Functional Polymers, U.S. Patent 6,028,155 (2000).

  121. Pham, H.H. and Winnik, M.A., “Synthesis, Characterization, and Stability of Carbodiimide Groups in Carbodiimide-Functionalized Latex Dispersions and Films,” J. Polym. Sci. Part A: Polym. Chem., 38, 855–869 (2000); (b) Pham, H.H., “Polymer Interdiffusion vs. Crosslinking in Carboxylic Acid-Carbodiimide Latex Films,” Ph.D. Thesis, University of Toronto, 1999.

    Article  CAS  Google Scholar 

  122. Pham, H.H. and Winnik, M.A., “Polymer Interdiffusion vs. Crosslinking in Carboxylic Acid-Carbodiimide Latex Films,” Macromolecules, 32, 7692–7695 (1999).

    Article  CAS  Google Scholar 

  123. Pham, H.H., Farinha, J.P.S., and Winnik, M.A., “Crosslink-ing, Miscibility, and Interface Structure in Blends of Poly(2-Ethylhexyl Methacrylate) Copolymers. An Energy Transfer Study,” Macromolecules, 33, 5850–5862 (2000); (b) Pham, H.H. and Winnik, M.A., “Film Formation from Blends of Carbodiimide and Carboxylic Acid-Functional Latex,” in Film Form-ation from Waterborne Dispersions, Provder, T. (Ed.), ACS Books, Washington, D.C., 2000.

    Article  CAS  Google Scholar 

  124. Guerts, J.M., “Latices with Intrinsic Crosslink Activity,” Ph.D. Thesis, Eindhoven University, 1998; (b) Guerts, J.M., van Es, J.J.G.S., and German, A.L., “Latexes with Intrinsic Crosslink Activity,” Prog. Org. Coat., 29, 107–115 (1996).

  125. Mohammed, S., Daniels, E.S., Sperling, L.H., Klein, A., and El-Aasser, M.S., “Isocyanate-Functionalized Latexes: Film Formation and Tensile Properties,” J. Appl. Polym. Sci., 66, 1869–1884 (1997).

    Article  CAS  Google Scholar 

  126. Hoy, K.L., “Estimating the Effectiveness of Latex Coalescing Aids,” Journal of Paint Technology, 45, No. 579, 51 (1973).

    CAS  Google Scholar 

  127. Toussanit, A., Wilde, M. De, Molenaar, F., and Mulvihill, J., “Calculation of Tg and MFFT Depression Due to Added Agents,” Prog. Org. Coat., 30, 179 (1997).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Taylor, J.W., Winnik, M.A. Functional latex and thermoset latex films. J Coat. Technol. Res. 1, 163–190 (2004). https://doi.org/10.1007/s11998-004-0011-5

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-004-0011-5

Keywords

Navigation