title: Photopolymerizable phosphate acrylates as comonomers in dental adhesives with or without triclosan monomer units.
abstract: Phosphate diacrylates (CO-DAP, TMP-DAP) based on castor oil or trimethylolpropane were synthesized and evaluated in dental adhesive formulations in comparison with 3-acryloyloxy-2-hydroxypropyl methacrylate phosphate (AMP-P). In an attempt to promote antibacterial activity, another photopolymerizable monomer (TCS-UMA) containing 5-chloro-2-(2,4-dichlorophenoxy)phenol moiety (triclosan) was prepared and incorporated in adhesive resins. Each of these monomers had a molecular structure confirmed by spectral methods. The photopolymerization rates for monomers (0.063-0.088s(-1)) were lower than those determined in the monomer combinations (0.116-0.158s(-1)) incorporating phosphate diacrylate (11wt.%), BisGMA (33wt.%), TEGDMA (10wt.%), UDMA (10wt.%) and HEMA (15wt.%), the degree of conversion varying between 63.4 and 74.5%. The formed copolymers showed high values for water sorption (18.65-57.02μg/mm(3)) and water solubility (3.51-13.38μg/mm(3)), and the contact angle was dependent on the presence of CO-DAP (θF1: 66.67°), TMP-DAP (θF2: 55.05°) or AMP-P (θF3: 52.90°) in the photocrosslinked specimens compared to the sample without phosphate monomer (θF4: 82.14°). The scanning electron microscopy image of the dentin-resin composite interface after applying our F1 formulation (pH: 4.1) and its light-curing for 20s supports the evidence of the formation of the hybrid layer with the tooth structure created by self-etching approach, with no gaps or cracks in the adhesive. A comparative analysis of the adhesion achieved with commercial adhesive systems (Single Bond Universal, C-Bond) rather indicates similarities than differences between them. The addition of triclosan methacrylate (1wt.%) into the formulation inhibited the bacterial growth of the Streptococcus mutans and Escherichia coli in the direct contact area due to the covalently linked antibacterial monomer.
authors.affiliation: Petru Poni Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi, Romania.
authors.forename: Violeta
authors.initials: V
authors.lastname: Melinte
authors.forename: Tinca
authors.initials: T
authors.lastname: Buruiana
authors.forename: Horia
authors.initials: H
authors.lastname: Aldea
authors.forename: Simona
authors.initials: S
authors.lastname: Matiut
authors.forename: Mihaela
authors.initials: M
authors.lastname: Silion
authors.forename: Emil C
authors.initials: EC
authors.lastname: Buruiana
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D003188:Composite Resins / Q000737:chemistry; D003738:Dental Cements / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010710:Phosphates / Q000138:chemical synthesis / Q000737:chemistry*; D058105:Polymerization / Q000528:radiation effects*; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D013052:Spectrometry, X-Ray Emission; D017550:Spectroscopy, Fourier Transform Infrared; D013295:Streptococcus mutans / Q000187:drug effects; D014260:Triclosan / Q000737:chemistry* / Q000494:pharmacology; D014867:Water / Q000737:chemistry
chemical_list: D000179:Acrylates; D000900:Anti-Bacterial Agents; D003188:Composite Resins; D003738:Dental Cements; D010710:Phosphates; D014867:Water; D014260:Triclosan
keywords: Antibacterial effect; Dental materials; Phosphate acrylates; Photopolymerization