Abstract
Migration stability and biocompatibility are the crucial features for a photoinitiator or coinitiator used in UV curable formulations, especially when the cured product is in direct contact with food or human skin. To reduce the migration issues and increase the biocompatibility, a polymerizable one-component photoinitiator, 1-(1,3-benzodioxol-5-yloxy)-3-(4-benzoylphenoxy)propan-2-yl acrylate (BDOBPAc), based on sesamol and benzophenone has been synthesized. The photopolymerization induced by BDOBPAc was monitored by real-time infrared spectroscopy. The rate of decomposition and the migration stability of photoinitiators were studied by UV-Vis spectroscopy. The results showed that BDOBPAc is an effective free radical photoinitiator with good migration stability, which has great potential to be widely used in the food packing or biomedical fields.
Similar content being viewed by others
Notes and references
J. P. Fouassier and J. Lalevée, Photoinitiators for Polymer Synthesis Scope, Reactivity and Efficiency, Wiley, New York, 2012.
Y. Yagci, S. Jockusch, N. J. Turro, Macromolecules, 2010, 43, 6245.
C. Decker, Polym. Int., 1998, 45, 133.
C. Decker, Prog. Polym. Sci., 1996, 21, 593.
W. Schnabel, Polymers and light, Wiley, New York, 2007.
R. S. Davidson, Exploring the Science, Technology and Applications of UV and EB Curing, SITA Technology Ltd., London, 1999.
K. Dietliker, Chemistry and Technology of UV and EB Formulations for Coatings, Inks and Paints, SITA Technology Ltd, London, 1991.
S. P. Pappas, UV Curing Science and Technology, Technology Marketing Corp., Norwalk, CT, 1978.
J. F. Rabek, Mechanisms of Photophysical Processes and Photochemical Reactions in Polymers, Theory and Applications, Wiley, New York, 1987.
J. P. Fouassier, Photoinitiation, Photopolymerization and Photocuring, Hanser Verlag, Munich, 1995.
B. R. Nayak, L. J. Mathias, J. Polym. Sci., Part A: Polym. Chem., 2005, 43, 5661.
S. Jauk, R. Liska, Macromol. Rapid Commun., 2005, 26, 1687.
T. Corrales, F. Catalina, C. Peinado, N. S. Allen, J. Polym. Sci., Part A: Polym. Chem., 2003, 159, 103.
R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2004, 42, 2285.
G. Ullrich, B. Ganster, U. Salz, N. Moszner, R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2006, 44, 1686.
P. Xiao, Y. Wang, M. Dai, S. Shi, G. Wu, J. Nie, Polym. Eng. Sci., 2008, 48, 884.
E. Meneguzzo, M. Visconti, D. Badoneand G. L. Bassi, US patent,6,492,514, 2002.
R. S. Davidson, The role of amines in UV-curing, in Radiation Curing in Polymer Science and Technology: Polymerisation Mechanisms, ed. J. P. Fouassier and J. F. Rabek, Elsevier Applied Science, London, 1993, vol. III.
M. A. Tehfe, M. El-Roz, J. Lalevée, F. Morlet-Savary, B. Graff, J. P. Fouassier, Eur. Polym. J., 2012, 48, 956.
K. Studer, C. Decker, E. Beck, R. Schwalm, Prog. Org. Coat., 2003, 48, 92.
K. Weisburger, A. B. Russfield, F. Hamburger, J. H. Weisburger, E. Boger, C. G. Van Dongen, K. C. Chu, Environ. Pathol. Toxicol., 1978, 28, 325.
E. Asmussen, Oper. Dent., 1985, 10, 61.
W. N. Albrecht, Scand. J. Work, Environ. Health, 1988, 14, 209.
P. D. Josephy, D. H. Evans, A. Parikh, F. P. Guengerich, Chem. Res. Toxicol., 1998, 11, 70.
S. S. Ana, A. Catarina, C. Isabel, M. C. José, P. Sarah, S. Catherine, P. L. Perfecto, J. Agric. Food Chem., 2009, 57, 9516.
S. Shi, H. Gao, G. Wu, J. Nie, Polymer, 2007, 48, 2860.
S. Shi, J. Nie, J. Biomed. Mater. Res., Part B, 2007, 82B, 44.
K. Wang, D. Yang, M. Xiao, X. Chen, F. Lu, J. Nie, Acta Biomater., 2009, 5, 2508.
J. Yang, F. Xu, S. Shi, J. Nie, Photochem. Photobiol. Sci., 2012, 11, 1377.
J. Yang, F. Xu, S. Shi, J. Nie, Photochem. Photobiol. Sci., 2013, 12, 323.
W. L. F. Armarego and C. L. L. Christina, Purification of Laboratory Chemicals, 6th edn, 2009.
J. W. Stansburya, S. H. Dickens, Dent. Mater., 2001, 17, 71.
G. A. O’Neil, M. B. Wisnudel, J. M. Torkelson, Macromolecules, 1996, 29, 7477.
B. W. Brooks, Proc. R. Soc. London, Ser. A, 1977, 357, 183.
X. Jiang, X. Luo, J. Yin, J. Photochem. Photobiol., A, 2005, 174, 165.
C. Dizman, S. Ates, L. Torun, Y. Yagci, Beilstein J. Org. Chem., 2010, 6, 56.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yang, J., Tang, R., Shi, S. et al. Synthesis and characterization of polymerizable one-component photoinitiator based on sesamol. Photochem Photobiol Sci 12, 923–929 (2013). https://doi.org/10.1039/c3pp00003f
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c3pp00003f