The Synthesis of New Type II Polymeric Photoinitiator (thioxantone) via Atom Transfer Radical Polymerization and Their Curing and Migration Studies
- 11 Downloads
Polymeric photoinitiators are widely used in ultraviolet (UV)-curable printing inks because of their low migration behavior. In this study, a new phenylphosphine oxide-polystyrene-thioxanthone (PPO-PSt-TX) polymeric photoinitiator was synthesized. Bis[(4-hydroxy)phenyl]phenyl phosphine oxide (BHPPO) that was synthesized by Grignard technique, was functionalized with 2-bromopropionyl bromide (atom transfer radical polymerization (ATRP) initiator) and then used in styrene polymerization. The bromine end-capped polystyrene was then reacted with 2-thioxanthone-thioacetic acid and final polymeric photoinitiator PPO-PSt-TX was obtained. Proton nuclear magnetic resonance (1H NMR), attenuated total reflectance- Fourier transform infrared spectroscopy (ATR-FTIR), gel permeation chromatography (GPC) and ultraviolet-visible spectroscopy (UV-Vis) confirmed the obtained structure. The curing characteristic of PPO-PSt-TX was compared with a standard flexographic printing varnish formulation containing thioxanthone (TX). The photopolymerization kinetics were determined by photo differential scanning calorimetry (Photo-DSC). The conversion of methylmethacrylate polymerization by using macrophotoinitiator is 78%. The migration behavior of PPO-PSt-TX was identified with liquid chromatography-mass spectrometry (LC-MS). It was shown that PPOPSt- TX macro photoinitiator is suitable for flexographic varnish and the migration level of photoinitiator is reduced by using polymeric photoinitiator.
Keywordspolymeric photoinitiator photopolymerization thioxanthone migration flexographic varnish
Unable to display preview. Download preview PDF.
This work was supported by Marmara University, Commission of Scientific Research Project (M.U.BAPKO) under grant FEN-CDRP- 120514-0163. The authors would like to thank Prof.Dr. Duygu Avcı for their valuable help in photo DSC studies.
- (1).K. Dietliker, Chemistry & Technology of UV & EB Formulation for Coatings, Inks & Paints, SITA Technology Ltd., London, 1991.Google Scholar
- (2).M. K. Mishra, Y. Yagci, Handbook of Radical Vinyl Polymerization, Marcel Dekker Inc., New York, 1998.Google Scholar
- (3).S. P. Pappas, UV Curing Science and Technolgy, Technology Marketing Corp., Norwalk, 1978.Google Scholar
- (4).J. P. Fouassier, Photoinitiation, Photopolymerization and Photocuring, Hanser Verlag, Munich, 1995.Google Scholar
- (5).R. S. Davidson, Exploring the Science, Technology and Applications of UV and EB Curing, SITA Technology Ltd., London, 1999.Google Scholar
- (15).M. A. Lago, A. Rodriguez-Bernaldo de Quiroz, R. Sendon, J. Bustos, and M. T. Nieto, Perfecto Paseiro, Photoinitiators: A Food Safety Review Food Additives & Contaminants: Part A, 32, 5 (2015).Google Scholar
- (16).J. Sutter, V. Dudler, and R. Meuwly, Packaging Materials 8. Printing Inks for Food Packaging Composition and Properties of Printing Inks, ILSI-EUROPE, Belgium, 2011.Google Scholar
- (25).L. Tiantian, S. Zhilong, X. Hongjie, J. Xuesong, M. Xiaodong, and Y. Jie, Chin. Chem. Lett., 43, 46 (2017).Google Scholar
- (38).D. J. Riley, Ph. D. Thesis, Synthesis and Characterization of Phosphorus Containing Polycarylene ether)s, Virgina Polytechnic Institute, 1997.Google Scholar
- (41).BS 4321: 1969 Methods of test for printing inks (resistance of prints to various physical and chemical agents)_Status: Superseded, Withdrawn (1969).Google Scholar
- (43).I. Clemente, M. Aznar, C. Nerín, and O. Bosetti, Food Addit. Contam. Part A, 33, 703 (2016).Google Scholar