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
Conference Title: 238th ACS National Meeting & Exposition, Fall 2009
Pub Type: Conferences
anti-bacterial, composites, dental polymers, Menschutkin reaction, polymerization, quaternary ammonium monomers