title: Synthesis of radiopaque cyclophosphazene monomers, properties of bulk polymers and their application to composite resin.
abstract: A series of studies was conducted on the synthesis of polyfunctional cyclophosphazene monomers having radiopacity and a polymerization group in the same molecule, and their properties and applicability to composite resin were examined. Using octachlorocyclotetraphosphazene, P4N4Cl8 (4PNC), monomers were synthesized by replacing the 1-4 of chlorine (Cl) with p-bromophenol (BrC6H4OH, BrPh), and replacing the residual number of Cl, 7-4, with 2-hydroxyethyl methacrylate [CH2:C(CH3)COOCH2CH2OH](HEMA), so as to obtain four kinds of transparent monomer having radiopacity and a polymerization group in the same molecule. We then analyzed these monomers and examined their physical properties after bulk-polymerization. Next, we prepared an organic composite filler using 4PN-(BrPh)3-(EMA)5 monomer, which showed comparatively good radiopacity, to produce a new experimental radiopaque composite resin. Although radiopacity improved in accordance with the increase in the number of BrPh molecules replaced, the mechanical properties of the polymer became poorer. Similarly it was proved that the radiopacity of composite resin made with 4PN-(BrPh)3-(EMA)5 monomer was equivalent or even superior, compared with the radiopacity of the front tooth. Consequently, it was shown that these synthesized monomers can be applied to visible light-cured radiopaque composite resin.
authors.affiliation: Department of Dental Materials, Nihon University School of Dentistry, Tokyo, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Anzai
authors.forename: M
authors.initials: M
authors.lastname: Kobori
authors.forename: K
authors.initials: K
authors.lastname: Yoshihashi
authors.forename: H
authors.initials: H
authors.lastname: Kikuchi
authors.forename: H
authors.initials: H
authors.lastname: Hirose
authors.forename: M
authors.initials: M
authors.lastname: Nishiyama
mesh_terms: D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry; D003188:Composite Resins / Q000138:chemical synthesis* / Q000737:chemistry; D003287:Contrast Media; D003764:Dental Materials / Q000138:chemical synthesis* / Q000737:chemistry; D006244:Hardness; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D010753:Phosphoranes / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D013055:Spectrophotometry, Infrared; D013314:Stress, Mechanical
chemical_list: D003188:Composite Resins; D003287:Contrast Media; D003764:Dental Materials; D008689:Methacrylates; D009943:Organophosphorus Compounds; D010636:Phenols; D010753:Phosphoranes; D011108:Polymers; C074235:cyclophosphazene monomer; C074539:Palfique Light; C022606:octachlorocyclotetraphosphazene; D017438:Bisphenol A-Glycidyl Methacrylate; C005044:hydroxyethyl methacrylate; C032037:4-bromophenol