Recently, we developed a light-induced polymerization method based on the copper-catalyzed alkyne azide cycloaddition reaction (photo-CuAAC). Photo-CuAAC polymerizations have proven to be ideal for preparing polymers with high glass transition temperature,1 mainly due to the stiff triazole linkages that are the products of CuAAC reactions. In order to implement photo-CuAAC polymerizations for rapid curing and hydrolytic stability, the design of non-degradable monomers is essential. Herein, we evaluated the effects of monomer structures on the conversion and the rate of photo-CuAAC polymerization. Di-functional azides and tri-functional alkynes were synthesized with variability in core structures (linear, cyclic and aromatic) and backbone functionalities (carbamates and ethers). The polymerization kinetic was monitored via FTIR. Increases in polymerization rates and final conversion were observed as we reduced the stiffness of core structures and backbones. For example, when the core structure of azides was changed from methylenediphenylene to cyclohexane, the average initial polymerization rate increased from 33±6 to 60±6 % conversion per minutes, and the final conversion increased from 75±3% to 95±1% when curing at 50°C. In conclusion, we demonstrated that structural elements of monomers are crucial for controlling both the polymerization rate and the maximum conversion in photo-CuAAC polymerizations. 1. T. Gong, B. J. Adzima, N. H. Baker, and C. N. Bowman, Adv. Mater. 2013, 25, 2024-2028.

Optimizing photo-CuAAC polymerization kinetic for dental restorative materials

249th National Meeting (2015)

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