Synthesis, characterization and evaluation of novel, anti-bacterial monomers for dental and biomedical applications

Published

August 16, 2009

Author(s)

Joseph M. Antonucci, Bruce O. Fowler, Diana N. Zeiger, Nancy Lin, Sheng Lin-Gibson

Abstract

Although progress has been made in reducing polymerization shrinkage through resin and filler phase modifications, and in designing improved dental adhesion systems, composite fillings still fail clinically because of bacterial infiltration and secondary caries development. One approach to prevent the occurrence of recurrent caries is to use polymeric dental materials with biocidal properties. The objective of this study was to adapt the classical, facile, and versatile Menschutkin reaction (the addition reaction of tertiary amines with organo-halides) for the synthesis of free radical, thermosetting monomers having quaternary ammonium groups in their chemical structures. These reactive monomers would also have solubility parameters similar to common dental resins. Thus, these monomers are expected to be easily miscible with current dental resin systems, have low leachability due to their multiple vinyl groups, and most importantly, by virtue of their quaternary ammonium functionalities are expected to yield copolymers and composites that are anti-bacterial by contact.

Proceedings Title

238th ACS National Meeting & Exposition, Fall 2009, Division of Polymers Science

Conference Dates

August 16-20, 2009

Conference Location

Washington, DC, US

Conference Title

238th ACS National Meeting & Exposition, Fall 2009

Pub Type

Conferences

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Keywords

anti-bacterial, composites, dental polymers, Menschutkin reaction, polymerization, quaternary ammonium monomers, , Dentistry

Citation

Antonucci, J. , Fowler, B. , Zeiger, D. , Lin, N. and Lin-Gibson, S. (2009), Synthesis, characterization and evaluation of novel, anti-bacterial monomers for dental and biomedical applications, 238th ACS National Meeting & Exposition, Fall 2009, Division of Polymers Science , Washington, DC, US, [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=901947 (Accessed October 13, 2025)