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    Characterization of Acid-neutralizing Basic Monomers in Co-solvent Systems by NMR

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    Issue Date
    2014
    Author
    Laurence, Jennifer S.
    Nelson, Benjamin Nels
    Ye, Qiang
    Park, Jonggu
    Spencer, Paulette
    Publisher
    Taylor & Francis
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    Metabolic activity of the oral microbiota leads to acidification of the microenvironment and promotes demineralization of tooth structure at the margin of composite restorations. The pathogenic impact of the biofilm at the margin of the composite restoration could be reduced by engineering novel dentin adhesives that neutralize the acidic micro-environment. Integrating basic moieties into methacrylate derivatives has the potential to buffer against acid-induced degradation, and we are investigating basic monomers for this purpose. These monomers must be compatible with existing formulations, which are hydrophobic and marginally miscible with water. As such, cosolvent systems may be required to enable analysis of monomer function and chemical properties. Here we present an approach for examining the neutralizing capacity of basic methacrylate monomers in a water/ethanol co-solvent system using NMR spectroscopy. NMR is an excellent tool for monitoring the impact of co-solvent effects on pKa and buffering capacity of basic monomers because chemical shift is extremely sensitive to small changes that most other methods cannot detect. Because lactic acid (LA) is produced by oral bacteria and is prevalent in this microenvironment, LA was used to analyze the effectiveness of basic monomers to neutralize acid. The 13C chemical shift of the carbonyl in lactic acid was monitored as a function of ethanol and monomer concentration and each was correlated with pH to determine the functional buffering range. This study shows that the buffering capacity of even very poorly water-soluble monomers can be analyzed using NMR.
    Description
    This is an Accepted Manuscript of an article published by Taylor & Francis in International Journal of Polymeric Materials and Polymeric Biomaterials in 2010, available online: http://www.tandfonline.com/10.1080/00914037.2013.845192
    URI
    http://hdl.handle.net/1808/24494
    DOI
    https://doi.org/10.1080/00914037.2013.845192
    Collections
    • Pharmaceutical Chemistry Scholarly Works [287]
    Citation
    Laurence, J. S., Nelson, B. N., Ye, Q., Park, J., & Spencer, P. (2014). Characterization of Acid-neutralizing Basic Monomers in Co-solvent Systems by NMR. International Journal of Polymeric Materials, 63(7), 361–367. http://doi.org/10.1080/00914037.2013.845192

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    785-864-8983
    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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