New Surface-active Comonomer for Adhesive Bonding

Abstract

Previous studies have indicated that chemical and physical characteristics of aromatic amines can be influenced by the nature of their substituents. The experimental question examined in the present study relates to the effects of replacing specific hydrogen atoms with methyl groups in a surface-active comonomer utilized in adhesive bonding protocols. N-2-propionic acid-N-3-(2-hydroxy-l-methacryloxy)propyl-3,5-dimethylaniline sodium salt (N35A) was synthesized by an addition reaction of glycidyl methacrylate with the sodium salt of N-(3,5-dimethylphenyl)alanine, which was formed by alkaline hydrolysis of ethyl-N-(3,5-dimethylphenyl)alanate that was prepared by condensation of ethyl-2-bromopropionate with 3,5-dimethylaniline. 1H and 13C NMR spectra and analysis by mass spectroscopy were consistent with N35A after it had been recrystallized from acetone. Color stability and adhesion-promoting capability of N35A were compared with those of N-2-acetic acid-N-3-(2-hydroxy-l-methacryloxy)propyl-4-methylanaline sodium salt (Na-NTG-GMA), the latter being widely used in commercial bonding formulations. Both N35A and Na-NTG-GMA polymerized within a few minutes at 23°C when dissolved in aliquots from a stock solution containing benzene 85 wt%, ethanol 14 wt%, and benzoyl peroxide 1.0 wt%; but with each at 0.018 molal concentration, the N35A suspension was more color-stable than that of the Na-NTG-GMA. In the protocol used, shear bond strengths of a hybrid composite to human dentin with N35A were 30.2 MPa, SD = 7.5 MPa, and with Na-NTG-GMA, 29.7 MPa, SD = 11.8 MPa (n = 7 each; t test, p = 0.93).