US EPA

7450811 

Journal Article 

Development of highly reactive mono-(meth)acrylates as reactive diluents for dimethacrylate-based dental resin systems 

Lu, H; Stansbury, JW; Nie, J; Berchtold, KA; Bowman, CN 

2005 

Yes 

Biomaterials
ISSN: 0142-9612
EISSN: 1878-5905 

26 

12 

1329-1336 

English 

15482820 

10.1016/j.biomaterials.2004.04.041 

WOS:000225760100001 

Reactive diluents such as triethyleneglycol-dimethacrylate (TEGDMA) have been widely used with bisphenol-A-glycidyl-dimethacrylate (Bis-GMA) to achieve restorative resins with appropriate viscosity and higher conversion. However, additional water sorption and polymerization shrinkage were also introduced. The aim of this work is to investigate whether the cure and material properties can be improved in dental resins containing novel mono-(meth)acrylates as reactive diluents so that these Bis-GMA-based copolymers have reduced polymerization shrinkage but higher overall double bond conversion. Several ultra-high-reactivity mono-(meth)acrylates that contain secondary functionalities have been synthesized and investigated. The polymerization rate and double bond conversion were monitored using photo-FTIR. Polymerization shrinkage, dynamic mechanical analysis, and flexural strength were characterized. Compared with the Bis-GMA/TEGDMA control, the Bis-GMA/mono-methacrylate systems studied showed higher final conversions, faster curing rates, and decreased polymerization shrinkage. Our optimum system Bis-GMA/morpholine carbamate methacrylate achieved 86% final conversion (vs. 65%), a polymerization rate 3.5 times faster, and a 30% reduction in polymerization volumetric shrinkage. These results indicate that certain highly reactive, novel mono-(meth)acrylates possess very promising potential to replace TEGDMA as reactive diluents and can readily be applied to develop superior dental resins. 

Dental resins; Photopolymerization; Reactive diluent; Volumetric shrinkage; Bending strength; Fourier transform infrared spectroscopy; Polymerization; Sorption; Synthesis (chemical); Viscosity; Reactive diluents; Water sorption; Resins; acrylic acid derivative; acrylic acid resin; copolymer; diluent; methacrylic acid; methacrylic acid derivative; morpholine derivative; resin; article; comparative study; material coating; polymerization; priority journal; Bisphenol A-Glycidyl Methacrylate; Dental Materials; Elasticity; Hardness; Kinetics; Materials Testing; Molecular Conformation; Photochemistry; Polyethylene Glycols; Polymethacrylic Acids; Tensile Strength; Ultraviolet Rays