Synthesis and photopolymerization of trifunctional methacrylates and their application as dental monomers.
1,1,1-Tris[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]ethane (THMPE) and tris[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]methane (THMPM) were synthesized and evaluated as base monomers in a dental composite system. The photopolymerization reactivity of the trifunctional methacrylates was similar to that of conventional 2,2-bis[4-(2'-hydroxy-3'-methacryloyloxy-propoxy)phenyl]propane (bis-GMA). Of the three monomers (THMPE, THMPM, and bis-GMA), THMPE has the greatest molecular volume, and its composite showed the lowest photopolymerization shrinkage of the composites derived from the three monomers. The water-solubility values for the light-activated composite resins formulated with THMPE and THMPM were much lower than that for a control bis-GMA composite. The trimethacrylates were not leached out into water from their corresponding photo-cured composites whereas the difunctional bis-GMA was eluted from its composite. The water sorption and flexural strength of the composite resins based on THMPE and THMPM were comparable to those of the bis-GMA composite. THMPE is promising for application as a photocurable dental monomer because of its good polymerization reactivity along with relatively low curing shrinkage and water-solubility of its photo-cured composite.
Chung
Chan-Moon
CM
Department of Chemistry, Yonsei University, Wonju, Kangwon-do 220-710, Korea. cmchung@dragon.yonsei.ac.kr
Kim
Min-Sung
MS
Kim
Joong-Gon
JG
Jang
Doo-Ok
DO
D003188:Composite Resins / Q000737:chemistry*; D003764:Dental Materials / Q000737:chemistry*; D008027:Light; D008422:Materials Testing; D008689:Methacrylates / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D008970:Molecular Weight; D011108:Polymers / Q000737:chemistry; D014867:Water / Q000737:chemistry
D003188:Composite Resins; D003764:Dental Materials; D008689:Methacrylates; D011108:Polymers; D014867:Water