Abstract
The efficiency of free radical polymerization by photoinitiating systems based on two Astrazon orange cyanine dyes was shown to be directly related to the isomerization process of the dye in the excited states. The impact of resin viscosity on photopolymerization reactions was measured and related to the overall radical quantum yields. The quantum yields were calculated according to the photocyclic behaviour of the initiating systems based on the Astrazon orange dyes. These dyes are characterized by a viscosity dependent photophysics, which leads to an isomerization-diffusion-controlled photopolymerization. Besides this demonstration, Astrazon orange dyes appeared to be very good candidates for free radical photopolymerization in the visible, presenting high absorption coefficient, low cost and good sensitivity.
Similar content being viewed by others
Notes and references
J. G. Drobny, Radiation technology for polymers, CRC Press, Bocan Raton, 2010.
R. Schwalm, UV coatings; basics, recent developments and new applications, Elsevier, Amsterdam, 2007.
X. Allonas, C. Croutxe-Barghorn, J. P. Fouassier, J. Lalevée, J. P. Malval and F. Morlet-Savary, in Lasers in Chemistry. Influencing Matter, M. Lackner, WILEY, Weinheim, 2008, vol. 2.
X. Allonas, C. Croutxé-Barghorn, K. W. Bögl, N. Helle and G. A. Schreiber, in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, 2012.
F. K. Bruder, R. Hagen, T. Rölle, M. S. Weiser, T. Fäcke, Angew. Chem., Int. Ed., 2011, 20, 4552.
A. Ibrahim, L. di Stefano, O. Tarzi, H. Tar, C. Ley, X. Allonas, Photochem. Photobiol., 2013, 89, 1283.
A. Ibrahim, X. Allonas, C. Ley, K. Kawamura, H. Berneth, F.-K. Bruder, T. Fäcke, R. Hagen, D. Hönel, T. Rölle, G. Walze, M. S. Weiser, Chem. - Eur. J., 2014, 20, 15102.
H. Tar, D. Sevinc Esen, M. Aydin, C. Ley, N. Arsu, X. Allonas, Macromolecules, 2013, 46, 3266.
C. Ley, J. Christmann, A. Ibrahim, L. H. di Stefano, X. Allonas, Beilstein J. Org. Chem., 2014, 10, 936.
K. Kawamura, J. Schmitt, M. Barnet, H. Salmi, C. Ley, X. Allonas, Chem. - Eur. J., 2013, 19, 12853.
K. Kawamura, C. Ley, J. Schmitt, M. Barnet, X. Allonas, J. Polym. Sci., Part A: Polym. Chem., 2013, 51, 4325–4330.
A. V. Metelisa, V. Lokshin, J. C. Micheau, A. Samt, R. Guglielmetti, V. I. Minkin, Phys. Chem. Chem. Phys., 2002, 4, 4340.
J. Hobley, V. Malatesta, R. Millini, L. Montanari, W. O. Neil Parker, Phys. Chem. Chem. Phys., 1999, 1, 3259.
J. Kabatc, B. Jedrzejewska, J. Paczkowski, J. Appl. Polym. Sci., 2006, 99, 207.
J. Kabatc, M. Pietrzak, J. Paczkowski, J. Chem. Soc., Perkin Trans. 2, 2002, 287.
J. Kabatc, B. Jedrzejewska, J. Packowski, J. Polym. Sci., Part A: Polym. Chem., 2000, 38, 2365.
J. Kabatc, Polymer, 2010, 51, 5028.
M. Sokmen, A. Ozkan, J. Photochem. Photobiol., A, 2002, 147, 77.
H. Kellet, J. Soc. Dyers Colour., 1968, 84, 257.
Y. Dattner, O. Yadid-Pecht, Sensors, 2010, 10, 5014.
C. Ley, P. Bordat, L. H. di Stefano, L. Remongin, A. Ibrahim, P. Jacques, X. Allonas, Phys. Chem. Chem. Phys., 2015, 17, 5982.
C. Decker, K. Moussa, Macromolecules, 1989, 22, 4455.
A. Ibrahim, V. Maurin, C. Ley, X. Allonas, C. Croutxe-Barghorn, F. Jasinski, Eur. Polym. J., 2012, 48, 1475.
O. I. Tarzi, X. Allonas, C. Ley, J. P. Fouassier, J. Polym. Sci., Part A: Polym. Chem., 2010, 48, 2594.
A. Ibrahim, B. El Fouhaili, A. Chan Yong, C. Ley, X. Allonas, C. Carré, Can. J. Chem., 2015, 93, 1.
J. Bañuelos Prieto, F. López Arbeloa, V. Martínez Martínez, T. Arbeola López, F. Amat-Guerri, M. Liras, I. López Arbeloa, Chem. Phys. Lett., 2004, 385, 29.
S. Suzuki, X. Allonas, J.-P. Fouassier, T. Urano, S. Takahara, T. Yamaoka, J. Photochem. Photobiol., A, 2006, 181, 60.
A. Ibrahim, C. Ley, X. Allonas, O. I. Tarzi, A. Chan Yong, C. Carré, R. Chevallier, Photochem. Photobiol. Sci., 2012, 11, 1682.
A. Ibrahim, X. Allonas, C. Ley, B. El Fouhaili, C. Carré, J. Photopolym. Sci. Technol., 2014, 27, 517.
D. Rehm, A. Weller, Isr. J. Chem., 1970, 8, 259.
B. Dellinger, M. Kasha, Chem. Phys. Lett., 1976, 38, 9.
Y. P. Sun, J. Saltiel, N. S. Park, E. A. Horburg, D. H. Waldeck, J. Phys. Chem., 1991, 95, 10336.
M. G. Neumann, I. A. Pastre, C. M. Previtali, J. Photochem. Photobiol., A, 1991, 61, 91.
J. Jakubiak, X. Allonas, J. P. Fouassier, A. Sionkowska, E. Andrzejewska, L. A. Linden, J. F. Rabek, Polymer, 2003, 44, 5219.
M. Dossot, X. Allonas, P. Jacques, Phys. Chem. Chem. Phys., 2002, 4, 2989.
C. R. Lambert, I. E. Kochevar, Photochem. Photobiol., 1997, 66, 15.
X. Allonas, P. Jacques, Chem. Phys., 1997, 215, 371.
A. Harriman, G. Porter, A. Wilowska, J. Chem. Soc., Faraday Trans. 2, 1983, 79, 807.
G. Jones II, S. Kumar, O. Klueva, D. Pacheco, J. Phys. Chem. A, 2003, 107, 8429.
S. Suzuki, X. Allonas, J. P. Fouassier, T. Urano, S. Takahara, T. Yamaoka, J. Photochem. Photobiol., A, 2006, 181, 60.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ley, C., Ibrahim, A. & Allonas, X. Isomerization controlled photopolymerization: effect of dye photophysics on photoinitiation efficiency. Photochem Photobiol Sci 15, 1054–1060 (2016). https://doi.org/10.1039/c6pp00028b
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c6pp00028b