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A study of acetoacetoxyethyl methacrylate hydrolysis in acrylic latex polymers as a function of pH

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Abstract

Acetoacetoxyethyl methacrylate (AAEM) is an ambient crosslinking monomer that, when incorporated into architectural coatings binders, provides coatings with improved hardness, scrub, stain, and dirt pick-up resistance. This study details the use of NMR spectroscopy to explore the hydrolysis profile of AAEM as a function of pH, type of neutralizer, and glass transition temperature of the binder. We have determined that AAEM has a hydrolysis profile that is independent of latex polymer pH relevant to coatings (pH 7–10). Lower T g latex polymers enable the diffusion of ammonia into the binder nanoparticles converting a larger amount of the acetoacetoxy moiety to the enamine form; this approach also allows for measuring the distribution of enamine and AAEM form in the latex polymer particle. The consequence of these findings is that AAEM may be utilized at a lower pH than previously envisioned without consequence to the hydrolysis profile of the acetoacetoxy functionality.

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Acknowledgments

Special thanks are extended to Arlene Pratt and Cynthia Leslie for their assistance in the synthesis and experimental setup of this study.

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Author notes

  1. Wayne Devonport

    Present address: Arkema Inc., 410 Gregson Drive, Cary, NC, 27511, USA

Authors and Affiliations

  1. The Dow Chemical Company, 727 Norristown Road, Spring House, PA, 19477, USA

    Kebede Beshah & Wayne Devonport

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  1. Kebede Beshah
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  2. Wayne Devonport
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Correspondence to Kebede Beshah.

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Beshah, K., Devonport, W. A study of acetoacetoxyethyl methacrylate hydrolysis in acrylic latex polymers as a function of pH. J Coat Technol Res 10, 821–828 (2013). https://doi.org/10.1007/s11998-013-9512-4

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  • DOI: https://doi.org/10.1007/s11998-013-9512-4

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