Amine-induced Polymerization of Aqueous HEMA/Aldehyde During Action as a Dentin Bonding Agent

Abstract

Aqueous mixtures of HEMA with glutaraldehyde or propionaldehyde polymerize by addition of catalytic amounts of amines or amino acids. The maximal reaction velocity of the transformation of HEMA/glutaraldehyde with glycine was obtained at pH 0.8. Kinetic data suggested a second-order reaction between glutaraldehyde and glycine, and solubility data suggested formation of a cross-linked polymer. A relatively high bond strength between dentin and resin composite was obtained by pre-treatment of dentin with Gluma (35% HEMA, 5% glutaraldehyde in water) adjusted to pH 1.0 with hydrochloric acid. It is proposed that on application of Gluma, amino-group-containing substances in dentin react with glutaraldehyde and start the formation of a HEMA polymer. This product may be cross-linked by an α,β-unsaturated glutaraldehyde aldol condensation product and may bond to dentin by aldehyde fixation to dentin proteins. Resin composite will bond to this product by copolymerization.

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