Journal of Dental Research, Vol 65, 1402-1405, Copyright © 1986 by International & American Associations for Dental Research Online Journals
Triazine monomers and their adhesion to dentin
C. H. Lee, X. Q. Liu and X. Q. Gong
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.
