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UV curable, liquid diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol

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Abstract

Novel, liquid cycloaliphatic diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol have been synthesized for use in ultraviolet (UV)- and electron beam (EB)-cured coatings, inks, and adhesives. Diacrylate monomers prepared from this unique diol, and containing less than 15 wt% trans-1,4-cyclohexanedimethanol diacrylate, are liquid at room temperature and readily soluble in other acrylate monomers and oligomers (in contrast to diacrylates prepared from 1,4-cyclohexanedimethanol, which are solid). More importantly, UV-cured coatings based on (cis,trans)-1,3/1,4-cyclohexanedimethanol diacrylates (1,3/1,4-CHDMDA) show superior hardness, scratch resistance, and chemical resistance as compared to common diacrylate monomers used in the UV coating industry such as tripropylene glycol diacrylate, hexanediol diacrylate, dipropylene glycol diacrylate, and propoxylated neopentyl glycol diacrylate. Thus, this new monomer appears to be a promising material for enhancing the performance of radiation-cured coatings, inks, and adhesives applied to a variety of substrates, including plastic, paper, wood, metal, and glass. This paper will summarize the synthesis of liquid diacrylates from (cis,trans)-1,3/1,4-cyclohexanedimethanol, as well as the performance properties of the corresponding UV-cured coatings.

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Acknowledgments

Special thanks go to Heqi Pan for helping with synthesis, Ben Schaefer for helping with property testing of the UV-cured coatings, John Bledsoe for GC analysis of the diacrylates, Don Robinson for recording NMR spectra, and Phil Gaarenstrom and Susanne Chambers for providing GPC data. In addition, the authors are grateful to Scott Bis, Paul Popa, Rodolfo Bayona, and Paul Foley for helpful discussions. Finally, The Dow Chemical Company is appreciated for supporting the external publication of this research.

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Authors and Affiliations

  1. Core R&D, The Dow Chemical Company, Midland, MI, 48674, USA

    Kiran K. Baikerikar, Michael L. Tulchinsky & John Argyropoulos

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  1. Kiran K. Baikerikar
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  2. Michael L. Tulchinsky
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  3. John Argyropoulos
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Correspondence to Kiran K. Baikerikar.

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Baikerikar, K.K., Tulchinsky, M.L. & Argyropoulos, J. UV curable, liquid diacrylate monomers based on (cis,trans)-1,3/1,4-cyclohexanedimethanol. J Coat Technol Res 7, 175–188 (2010). https://doi.org/10.1007/s11998-009-9185-1

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  • DOI: https://doi.org/10.1007/s11998-009-9185-1

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