Preparation of antibacterial and radio-opaque dental resin with new polymerizable quaternary ammonium monomer.
OBJECTIVE
A new polymerizable quaternary ammonium monomer (IPhene) with iodine anion was synthesized and incorporated into Bis-GMA/TEGDMA (50/50, wt/wt) to prepare antibacterial and radio-opaque dental resin.


METHODS
IPhene was synthesized through a 2-steps reaction route, and its structure was confirmed by FT-IR and (1)H-NMR spectra. IPhene was incorporated into Bis-GMA/TEGDMA (50/50, wt/wt) with a series of mass fraction (from 10 wt.% to 40 wt.%). Degree of monomer conversion (DC) was determined by FT-IR analysis. Polymerization shrinkage was determined according to the variation of density before and after polymerization. The flexural strength, modulus of elasticity, and fracture energy were measured using a three-point bending set up. Radiograph was taken to evaluate the radio-opacity of the polymer. A single-species biofilm model with Streptococcus mutans (S. mutans) as the tests organism was used to evaluate the antibacterial activity of the polymer. Bis-GMA/TEGDMA resin system without IPhene was used as a control group.


RESULTS
FT-IR and (1)H-NMR spectra of IPhene revealed that IPhene was the same as the designed structure. ANOVA analysis showed that when mass fraction of IPhene was more than 10 wt.%, the obtained resin formulation had lower DC, polymerization shrinkage, FS, and FM than control resin (p<0.05). Polymers with 20 wt.% and 30 wt.% IPhene had higher fracture energies than control polymer (p<0.05). IPhene containing samples had higher radio-opacity than control group (p<0.05), and radio-opacity of IPhene containing sample increased with the increasing of IPhene mass fraction (p<0.05). Only polymers with 30 wt.% and 40 wt.% of IPhene showed antibacterial activity (p<0.05).


CONCLUSIONS
IPhene could endow dental resin with both antibacterial and radio-opaque activity when IPhene reached 30 wt.% or more. Though sample with 30 wt.% of IPhene had lower FS and FM than control group, its lower volumetric shrinkage, higher fracture energy, higher radio-opacity, and antibacterial activity still made it having potential to be used in dentistry.
Department of Biomaterials Science, Institute of Dentistry and Biocity Turku Biomaterial Research Program, University of Turku, Lemminkäisenkatu 2, Turku 20520, Finland; Turku Clinical Biomaterials Centre-TCBC, University of Turku, Itäinen Pitkäkatu 4 B, Turku FI-20520, Finland; College of Materials Science and Engineering, South China University of Technology, Guangzhou 510641, China. Electronic address: hejin@utu.fi.
Jingwei
J
He
Institute of Dentistry, University of Turku, Turku 20520, Finland.
Eva
E
Söderling
Department of Biomaterials Science, Institute of Dentistry and Biocity Turku Biomaterial Research Program, University of Turku, Lemminkäisenkatu 2, Turku 20520, Finland; Turku Clinical Biomaterials Centre-TCBC, University of Turku, Itäinen Pitkäkatu 4 B, Turku FI-20520, Finland; Institute of Dentistry, University of Turku, Turku 20520, Finland.
Lippo V J
LV
Lassila
Department of Biomaterials Science, Institute of Dentistry and Biocity Turku Biomaterial Research Program, University of Turku, Lemminkäisenkatu 2, Turku 20520, Finland; Turku Clinical Biomaterials Centre-TCBC, University of Turku, Itäinen Pitkäkatu 4 B, Turku FI-20520, Finland; Institute of Dentistry, University of Turku, Turku 20520, Finland; City of Turku Welfare Division, Oral Health Care, Turku 20101, Finland.
Pekka K
PK
Vallittu
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D018441:Biofilms; D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry; D055119:Elastic Modulus; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing; D011092:Polyethylene Glycols / Q000737:chemistry; D058105:Polymerization; D011109:Polymethacrylic Acids / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012117:Resins, Synthetic / Q000138:chemical synthesis*; D017550:Spectroscopy, Fourier Transform Infrared; D013295:Streptococcus mutans / Q000187:drug effects; D013718:Tensile Strength
D000900:Anti-Bacterial Agents; D011109:Polymethacrylic Acids; D000644:Quaternary Ammonium Compounds; D012117:Resins, Synthetic; C020946:triethylene glycol dimethacrylate; D011092:Polyethylene Glycols; D017438:Bisphenol A-Glycidyl Methacrylate
Antibacterial activity; Dental resin; Double bond conversion; Mechanical property; Polymerization shrinkage; Radio-opacity; Synthesis