Synthesis, characterization, shrinkage and curing kinetics of a new low-shrinkage urethane dimethacrylate monomer for dental applications.
OBJECTIVE
The aim of the study was to synthesize and characterize an isophorone-based urethane dimethacrylate (IP-UDMA) resin-monomer and to investigate its shrinkage and curing kinetics.


METHODS
The IP-UDMA monomer was synthesized through the reaction of polyethylene glycol 400 and isophorone diisocyanate followed by reacting with HEMA to terminate it with methacrylate end groups. The reaction was followed using a standard back titration method and FTIR spectroscopy. The final product was purified and characterized using FTIR, (1)H NMR, elemental analysis and refractive index measurement. The shrinkage-strain of the specimens photopolymerized at circa 700mW/cm(2) was measured using the bonded-disk technique at 23, 35, and 45 degrees C. Initial shrinkage-strain-rates were obtained by numerical differentiation of shrinkage-strain data with respect to time. Degree-of-conversion of the specimens was measured using FTIR spectroscopy. The thermal curing kinetics of the monomer were also studied by differential scanning calorimetry (DSC).


RESULTS
The characterization methods confirmed the suggested reaction route and the synthesized monomer. A low shrinkage-strain of about 4% was obtained for the new monomer. The results showed that the shrinkage-strain-rate of the monomer followed the autocatalytic model of Kamal and Sourour [Kamal MR, Sourour S. Kinetic and thermal characterization of thermoset cure. Polym Eng Sci 1973;13(1):59-64], which is used to describe the reaction kinetics of thermoset resins. The model parameters were calculated by linearization of the equation.


CONCLUSIONS
The model prediction was in a good agreement with the experimental data. The properties of the new monomer compare favorably with properties of the commercially available resins.
Atai
Mohammad
M
Iran Polymer and Petrochemical Institute (IPPI), Tehran, Iran. m.atai@ippi.ac.ir
Ahmadi
Mehdi
M
Babanzadeh
Samal
S
Watts
David C
DC
D000180:Acrylic Resins / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D000704:Analysis of Variance; D002152:Calorimetry, Differential Scanning; D018772:Dental Marginal Adaptation; D003764:Dental Materials / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D003799:Dental Stress Analysis; D006358:Hot Temperature; D007700:Kinetics; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing; D008689:Methacrylates / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D044367:Phase Transition; D011140:Polyurethanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D012212:Rheology; D017550:Spectroscopy, Fourier Transform Infrared; D014783:Viscosity
D000180:Acrylic Resins; D003764:Dental Materials; D008689:Methacrylates; D011140:Polyurethanes; C041293:isophorone polyurethane; C097103:polyurethane dimethacrylate