Triazine monomers and their adhesion to dentin

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 degrees 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.