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Synthesis and photopolymerization kinetics of 2-phenyl-benzodioxole

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Abstract

In this paper, a new photocoinitiator for free radical photopolymerization, belonging to the benzodioxole (BDO) derivatives, was synthesized and characterized, and the effect of phenyl at the 2-position of BDO was estimated. The structure of PhBDO was characterized by elemental analysis, 1H NMR and 13C NMR. Laser flash photolysis (LFP) and an electron spin resonance spin trapping technique (ESR-ST) were used to study the photochemical mechanisms. The rate of decomposition (Rd) of PhBDO in acetonitrile was studied by UV-Vis spectroscopy and the photopolymerization kinetics were monitored by real time Fourier Transform near-IR (FT-IR). The FT-IR results showed that the concentration of PhBDO and BP functionalities of the acrylates and the light intensity affected the polymerization rate and the final conversion. The results showed that the BP/PhBDO system had the same hydrogen abstraction mechanism and reactivity as the BP/BDO system. Consequently, PhBDO could also be an effective coinitiator.

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Notes and References

  1. J. P. Fouassier, and J. Lalevée, Photoinitiators for polymer synthesis scope, reactivity and efficiency, Wiley, New York, 2012.

    Book  Google Scholar 

  2. B. George, and R. Dhamodharan, A study of the photopolymerization kinetics of methyl methacrylate using novel benzophenone initiators, Polym. Int., 2001, 50(8), 897–905.

    Article  CAS  Google Scholar 

  3. G. Yilmaz, B. Aydogan, G. Temel, N. Arsu, N. Moszner, and Y. Yagci, Thioxanthonefluorenes as visible light photoinitiators for free radical polymerization, Macromolecules, 2010, 43, 4520.

    Article  CAS  Google Scholar 

  4. A. Ledwith, J. A. Bosley, and M. D. Purbrick, Exciplex interactions in photoinitiator of polymerization by fluorenone-amine systems, J. Oil Colour Chem. Assoc., 1978, 61, 95.

    CAS  Google Scholar 

  5. J. V. Crivello, and K. Dietliker, Photoinitiators for free radical, cationic and anionic photopolymerization, Wiley, London, 2nd edn, 1998, vol. 3.

  6. B. R. Nayak, and L. J. Mathias, A novel photoinimer for the polymerization of acrylates and methacrylates, J. Polym. Sci., Part A: Polym. Chem., 2005, 43, 5661.

    Article  CAS  Google Scholar 

  7. S. Jauk, and R. Liska, Photoinitiators with functional groups, Macromol. Rapid Commun., 2005, 26, 1687–1692.

    Article  CAS  Google Scholar 

  8. N. Arsu, R. Stephen Davidson, and R. Holman, Factors affecting the photoyellowing which occurs during the photoinitiated polymerization of acrylates, J. Photochem. Photobiol., A, 1995, 87, 169–175.

    Article  CAS  Google Scholar 

  9. S. Shi, H. Gao, G. Wu, and J. Nie, Cyclic acetal as coinitiator for bimolecular photoinitiating systems, Polymer, 2007, 48, 2860–2865.

    Article  CAS  Google Scholar 

  10. S. Shi, and J. Nie, A natural component as coinitiator for unfilled dental resin composites, J. Biomed. Mater. Res., Part B, 2007, 82B, 44.

    Article  CAS  Google Scholar 

  11. S. Shi, and J. Nie, Investigation of 3,4-methylenedioxybenzene methoxyl methacrylate as coinitiator and comonomer for dental application, J. Biomed. Mater. Res., Part B, 2007, 82B, 487.

    Article  CAS  Google Scholar 

  12. S. Shi, P. Xiao, K. Wang, Y. Gong, and J. Nie, Influence of chemical structures of benzodioxole-based coinitiators on the properties of the unfilled dental resin, Acta Biomater., 2010, 6, 3067.

    Article  CAS  Google Scholar 

  13. K. Wang, D. Yang, M. Xiao, X. Chen, F. Lu, and J. Nie, Sesamin as a coinitiator for unfilled dental restorations, Acta Biomater., 2009, 5, 2508.

    Article  CAS  Google Scholar 

  14. J. Yang, and J. Nie, Influence of structure of benzodioxole derivatives on photoinitiation efficiency of benzophenone, Photochem. Photobiol. Sci., 2012, 11, 1377–1382.

    Article  CAS  Google Scholar 

  15. W. L. F. Armarego, and C. Chai, Purification of laboratory chemicals, Butterworth-Heinemann, Oxford, 6th edn, 2009.

    Google Scholar 

  16. M. Dossot, H. Obeid, X. Allonas, P. Jacques, J. P. Fouassier, and A. Merlin, Photopolymerization of acrylates in the presence of phenolic derivatives: Role of the photoinitiating system, J. Appl. Polym. Sci., 2004, 92, 1154–1164.

    Article  CAS  Google Scholar 

  17. C. Decker, and K. Moussa, Real-time kinetic study of laser-induced polymerization, Macromolecules, 1989, 22, 4455–4462.

    Article  CAS  Google Scholar 

  18. J. W. Stansburya, and S. H. Dickens, Determination of double bond conversion in dental resins by near infrared spectroscopy, Dent. Mater., 2001, 17, 71.

    Article  Google Scholar 

  19. F. Xu, J.-L. Yang, Y.-S. Gong, G.-P. Ma, and J. Nie, A fluorinated photoinitiator for surface oxygen inhibition resistance, Macromolecules, 2012, 45, 1158–1164.

    Article  CAS  Google Scholar 

  20. S. Jauk, and R. Liska, Photoinitiators with functional groups, 8, Macromol. Rapid Commun., 2005, 26, 1687–1692.

    Article  CAS  Google Scholar 

  21. A. Criqui, J. Lalevee, X. Allonas, J. P. Fouassier, Macromol. Chem. Phys., 2008, 209, 2223–2231.

    Article  CAS  Google Scholar 

  22. J. Yang, and J. Nie, Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator, Photochem. Photobiol. Sci., 2013, 12, 323–329. 323.

    Article  CAS  Google Scholar 

  23. A. Criqui, J. Lalevée, X. Allonas, J.-P. Fouassier, Electron spin resonance spin trapping technique: application to the cleavage process of photoinitiators, Macromol. Chem. Phys., 2008, 209, 2223–2231.

    Article  CAS  Google Scholar 

  24. J. F. Rabek, Mechanisms of photophysical processes and photochemical reactions in polymers, theory and applications, Wiley, New York, 1987.

    Google Scholar 

  25. G. A. O’Neil, M. B. Wisnudel, and J. M. Torkelson, A critical experimental examination of the gel effect in free radical polymerization: do entanglements cause autoacceleration, Macromolecules, 1996, 29, 7477–7490.

    Article  Google Scholar 

  26. X. Jiang, X. Luo, and J. Yin, Polymeric photoinitiators containing in-chain benzophenone and coinitiators amine: effect of the structure of coinitiator amine on photopolymerization, J. Photochem. Photobiol., A, 2005, 174, 165–170.

    Article  CAS  Google Scholar 

  27. C. Dizman, S. Ates, L. Torun, and Y. Yagci, Synthesis, characterization and photoinduced curing of polysulfones with (meth)acrylate functionalities, Beilstein J. Org. Chem., 2010, 6, 56.

    Article  Google Scholar 

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Correspondence to Xiaoqun Zhu.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c3pp50343g

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Wang, B., Yang, J., Nie, J. et al. Synthesis and photopolymerization kinetics of 2-phenyl-benzodioxole. Photochem Photobiol Sci 13, 651–659 (2014). https://doi.org/10.1039/c3pp50343g

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  • DOI: https://doi.org/10.1039/c3pp50343g

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