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New acid BisGMA analogs for dental adhesive applications with antimicrobial activity
Violeta Melinte1, Tinca Buruiana1, Andreea Chibac1
1Polyaddition and Photochemistry Department, Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania.
Objective:
To achieve bisphenol A glycerolate dimethacrylate (BisGMA) analogs with reduced viscosity to be used in the formulation of dental adhesives containing biocidal components.
Methods:
A series of low-viscosity BisGMA derivatives (η: 39-12Pas) modified with 30, 60 and, respectively 80mol% carboxylic acid units were synthesized and characterized. Hydrogen bonding interactions in our monomers, the photopolymerization behavior and implicitly the conversion degree (DC) for some experimental adhesive formulations containing acid-modified BisGMA, commercial BisGMA (only in F1-F3), triethyleneglycol dimethacrylate and 2-hydroxyethyl methacrylate were examined by FTIR spectroscopy. The water effects on the photocrosslinked networks together with the flexural strength/modulus were also investigated. The adhesive penetration into the dentin surface was surveyed by SEM analysis, and the antimicrobial activity triggered by the incorporation of 0.5wt% AgNO3, 10wt% zinc methacrylate or 1wt% triclosan methacrylate in selected adhesive formulations on the growth of Streptococcus mutans and Candida albicans strains was evidenced.
Results:
The contribution of the hydrogen bonding interactions was found to be lower in BisGMA derivatives than in non-modified BisGMA, and the DC varied between 56.5 (F6) and 83.7% (F1) compared with a control formulation based on BisGMA:TEGDMA (DC=58.2%). The flexural strength and flexural modulus varied in the range 33.7MPa (F6)-54.4MPa (F8)MPa and 0.64 (F6)-1.43 (F8)GPa, respectively. SEM observation of adhesive-dentin interface revealed the formation of resin tags for the carboxyl-containing adhesive, while for the control adhesive they are hardly formed. Also, the microorganism development was inhibited, the proposed materials displaying antimicrobial activity.
Significance:
The experimental formulations based on carboxyl-functionalized BisGMA exhibit a similar or even improved behavior over control sample, suggesting their potential applicability as antimicrobial dental adhesives.
