Triazine Monomers and Their Adhesion to Dentin

Abstract

A series of 4,6-dichloro-1,3,5-triazines [e.g., 2-allylamino-(ADT), diallylamino-(DADT), 2-N-p-allyloxyphenylamino-, 2-N-allyl-N-phenylamino-, and 2-N-allyl-N-p-tolylamino-4,6-dichloro-1,3,5-triazine] was synthesized and characterized by IR, NMR, and mass spectrometry. These monomers have chlorine atoms that can react with NH₂ or OH groups and double bonds capable of copolymerization. Aniline reacted readily with ADT and DADT, ethanol reacted with ADT, but acetone, H₂O, and DMF did not react with either triazine. It appears that ADT or DADT will react with dentinal collagen through NH₂ or OH groups in the peptide side-chains. An aprotic solvent should be used for ADT or DADT, but absolute dryness in clinical usage is not essential because of the slow hydrolysis of ADT and DADT. Stability of the N-di-substituted amino derivative (DADT) is greater than that of the mono-substituted compound (ADT), which may isomerize. ADT and methyl methacrylate were copolymerized at 37°C with amine-peroxide. ADT solutions enhanced the adhesive strength of restorative resin to dentin. Thus, monomers such as ADT and DADT appear to be promising dentin-bonding agents.

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