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Photoreactivity study of photoinitiated free radical polymerization using Type II photoinitiator containing thioxanthone initiator as a hydrogen acceptor and various amine-type co-initiators as hydrogen donors

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Abstract

In this work, free radical photopolymerization of trimethylolpropane trimethacrylate (TMPTMA) is initiated. We investigated the corresponding photoreactivity by using Type II photoinitiator (PI) systems based on thioxanthone (TX) as a hydrogen acceptor and five amine-type molecules, such as N-phenylglycine (NPG), triethylamine (TEA), triethanolamine (TEOA), 2,2′-(4-methylphenylimino)diethanol (p-TDEA), and N-phenyldiethanolamine (n-PDEA), as hydrogen donors. Their photochemical and photophysical properties are studied. The TX hydrogen acceptor displayed rather red-shifted compared to all the hydrogen donor compounds. The hydrogen donor compounds exhibited the absorption band at lower than 300 nm, which followed the trend of p-TDEA > n-PDEA > NPG > TEOA > TEA. All the packages exhibit good electron-transfer ability by the calculation of the free energy changes (ΔGET) through cyclic voltammetry (CV) measurement. However, the hydrogen donors with different steric hindrance, secondary, and tertiary amines have a decisive influence on the photoreactivity; that is, the TX/TEOA package shows the best double-bond conversion (DC) efficiency than other formulations under similar weight ratios (hydrogen acceptor: hydrogen donor = 1:2 wt%). We then conduct the photoreactivity based on TX/TEOA formulation with different weight ratios. The DC values are in the order of 1:2 wt% > 1.5:1.5 wt% > 2:1 wt%. Under suitable amount of hydrogen donor, the TX/TEOA-based formulation also exhibits stable DC value at air atmosphere.

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References

  1. Fuchs, Y, Soppera, O, Haupt, K, “Photopolymerization and Photostructuring of Molecularly Imprinted Polymers for Sensor Applications—A Review.” Analyt. Chim. Acta, 717 7–20 (2012)

    Article  CAS  Google Scholar 

  2. Kaur, M, Srivastava, AK, “Photopolymerization: A Review.” J. Macromol. Sci. Polym. Rev. C, 42 (4) 481–512 (2002)

    Article  Google Scholar 

  3. Karasu, F, Croutxe-Barghorn, C, Allonas, X, Van Der Ven, LGJ, “Free Radical Photopolymerization Initiated by UV and LED: Towards UV Stabilized, Tack Free Coatings.” J. Polym. Sci. Part A Polym. Chem., 52 3597–3607 (2014)

  4. Ikemura, K, Endo, T, “A Review of the Development of Radical Photopolymerization Initiators Used for Designing Light-Curing Dental Adhesives and Resin Composites.” Dental Mater. J., 29 481–501 (2010)

    Article  CAS  Google Scholar 

  5. O’Brien, J, Hughes, PJ, Brunet, M, O’Neill, B, Alderman, J, Lane, B, O’Riordan, A, O’Driscoll, C, “Advanced Photoresist Technologies for Microsystems.” J. Micromech. Microengine., 11 353–358 (2001)

    Article  Google Scholar 

  6. Altinkok, C, Uyar, T, Tasdelen, MA, Yagci Y, “In Situ Synthesis of Polymer/Clay Nanocomposites by Type II Photoinitiated Free Radical Polymerization.” J. Polym. Sci. Part A Polym. Chem., 49 3658–3663 (2011).

  7. Yagci, Y, Jockusch, S, Turro, NJ, “Photoinitiated Polymerization: Advances, Challenges, and Opportunities.” Macromolecules, 43 6245–6260 (2010)

    Article  CAS  Google Scholar 

  8. Garra, P, Dietlin, C, Morlet-Savary, F, Dumur, F, Gigmes, D, Fouassier, JP, Lalevee, J, “Photopolymerization Processes of Thick Films and in Shadow Areas: A Review for the Access to Composites.” Polym. Chem., 8 7088–7101 (2017)

    Article  CAS  Google Scholar 

  9. Khudyakov, IV, “Fast Photopolymerization of Acrylate Coatings: Achievements and Problems.” Prog. Org. Coat., 121 151–159 (2018)

    Article  CAS  Google Scholar 

  10. Urano, T, “Photopolymerization Mechanisms and Methods of Investigation.” J. Photopolym. Sci. Technol., 16 129–156 (2003)

    Article  CAS  Google Scholar 

  11. Fouassier, JP, Allonas, X, Burget, D, “Photopolymerization Reactions Under Visible Lights: Principle, Mechanisms and Examples of Applications.” Prog. Org. Coat., 47 16–36 (2003)

    Article  CAS  Google Scholar 

  12. Bowman, CN, Kloxin, CJ, “Toward an Enhanced Understanding and Implementation of Photopolymerization Reactions.” AIChE J., 54 2775–2795 (2008)

    Article  CAS  Google Scholar 

  13. Shao, JZ, Huang, Y, Fan, QU, “Visible Light Initiating Systems for Photopolymerization: Status, Development and Challenges.” Polym. Chem., 5 4195–4210 (2014)

    Article  CAS  Google Scholar 

  14. Xiao, P, Zhang, J, Dumur, F, Tehfe, MA, Morlet-Savary, F, Graff, B, Gigmes, D, Fouassier, JP, Lalevee, J, “Visible Light Sensitive Photoinitiating Systems: Recent Progress in Cationic and Radical Photopolymerization Reactions Under Soft Conditions.” Prog. Polym. Sci., 41 32–66 (2015)

    Article  CAS  Google Scholar 

  15. Decker, C, “Photoinitiated Crosslinking Polymerisation.” Prog. Polym. Sci., 21 593–650 (1996)

    Article  CAS  Google Scholar 

  16. Chen, YC, Kuo, YT, Ho, TH, “Photo-polymerization Properties of Type-II Photoinitiator Systems Based on 2-Chlorohexaaryl Biimidazole (o-Cl-HABI) and Various N-phenylglycine (NPG) Derivatives.” Photochem. Photobio. Sci., 18 190–197 (2019)

    Article  CAS  Google Scholar 

  17. Li, YH, Chen, YC, “Triphenylamine-Hexaarylbiimidazole Derivatives as Hydrogen-Acceptor Photoinitiators for Free Radical Photopolymerization Under UV and LED Light.” Polym. Chem., 11 1504–1513 (2020)

    Article  CAS  Google Scholar 

  18. Dogruyol, SK, Dogruyol, Z, Arsu, N, “A Thioxanthone-based Visible Photoinitiator.” J. Polym. Sci. Part A Polym. Chem., 49 4037–4043 (2011).

  19. Dadashi-Silab, S, Aydogan, C, Yagci, Y, “Shining a Light on an Adaptable Photoinitiator: Advances in Photopolymerizations Initiated by Thioxanthones.” Polym. Chem., 6 6595–6615 (2015)

    Article  CAS  Google Scholar 

  20. Allushi, A, Kutahya, C, Aydogan, C, Kreutzer, J, Yilmaz, G, Yagci, Y, “Conventional Type II Photoinitiators as Activators for Photoinduced Metal-Free Atom Transfer Radical Polymerization.” Polym. Chem., 8 1972–1977 (2017)

    Article  CAS  Google Scholar 

  21. Zhang, J, Xiao, P, Shi, SQ, Nie, J, “Synthesis and Photopolymerization Kinetics of Multifunctional Aromatic Urethane Acrylates Containing Tertiary Amine Group.” Polym. Adv. Technol., 20 (1) 16–20 (2009)

    Article  CAS  Google Scholar 

  22. Wu, GQ, Shi, SQ, Xiao, P, Nie, J, “Synthesis and Characterization of Aliphatic Amine Co-initiator with Different Chain Length for Photopolymerization of Dimethacrylate.” J. Photochem. Photobio. A Chem., 188 (2–3) 260–266 (2007)

    Article  CAS  Google Scholar 

  23. Oguri, M, Yoshida, Y, Yoshihara, K, Miyauchi, T, Nakamura, Y, Shimoda, S, Hanabusa, M, Momoi, Y, Van Meerbeek, B, “Effects of Functional Monomers and Photo-Initiators on the Degree of Conversion of A Dental Adhesive.” Acta Biomater., 8 (5) 1928–1934 (2012)

    Article  CAS  Google Scholar 

  24. Kucybala, Z, Pietrzak, M, Paczkowski, J, Linden, LA, Rabek, JF, “Kinetic Studies of A New Photoinitiator Hybrid System Based on Camphorquinone-N-phenylglycine Derivatives for Laser Polymerization of Dental Restorative and Stereolithographic (3D) Formulations.” Polymer, 37 (20) 4585–4591 (1996)

    Article  CAS  Google Scholar 

  25. Mikulchyk, T, Martin, S, Naydenova, I, “Investigation of the Sensitivity to Humidity of an Acrylamide-based Photopolymer Containing N-phenylglycine as a Photoinitiator.” Opt. Mater., 37 810–815 (2014)

    Article  CAS  Google Scholar 

  26. Chen, YC, Kuo, YT, “Photocuring Kinetic Studies of TMPTMA Monomer by Type II Photoinitiators of Different Weight Ratios of 2-Chlorohexaaryl Biimidazole (o-Cl-HABI) and N-Phenylglycine (NPG).” J. Photopolym. Sci. Technol., 31 487–492 (2018)

    Article  CAS  Google Scholar 

  27. Park, YJ, Lim, DH, Kim, HJ, Park, DS, Sung, IK, “UV- and Thermal-Curing Behaviors of Dual-Curable Adhesives Based on Epoxy Acrylate Oligomers.” Int. J. Adhes. Adhes., 29 710–717 (2009)

    Article  CAS  Google Scholar 

  28. Kissinger, PT, Holt, PT, Reilley, CN, “Electrochemical Studies of Thioxanthene, Thioxanthone, and Related Species in Nonaqueous Media.” J. Electroanalyt. Chem. Interfacial Electrochem., 33 1–12 (1971)

    Article  CAS  Google Scholar 

  29. Rehm, D, Weller, A, “Kinetics of Fluorescence Quenching by Electron and H-Atom Transfer.” Israel J. Chem., 8 259–271 (1970)

    Article  CAS  Google Scholar 

  30. Husar, B, Ligon, SC, Wutzel, H, Hoffmann, H, Liska, R, “The Formulator’s Guide to Anti-oxygen Inhibition Additives.” Prog. Org. Coat., 77 1789–1798 (2014)

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support from the Ministry of Science and Technology (MOST 108-2221-E-992-033), Taiwan ROC, and National Kaohsiung University of Science and Technology are gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemical and Materials Engineering, National Kaohsiung University of Science and Technology, Kaohsiung City, 80778, Taiwan, ROC

    Yung-Chung Chen, Ting-Yu Liu & Yan-Heng Li

  2. Photo-SMART (Photo-sensitive Material Advanced Research and Technology Center), National Kaohsiung University of Science and Technology, Kaohsiung City, 80778, Taiwan, ROC

    Yung-Chung Chen

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  1. Yung-Chung Chen
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Chen, YC., Liu, TY. & Li, YH. Photoreactivity study of photoinitiated free radical polymerization using Type II photoinitiator containing thioxanthone initiator as a hydrogen acceptor and various amine-type co-initiators as hydrogen donors. J Coat Technol Res 18, 99–106 (2021). https://doi.org/10.1007/s11998-020-00401-9

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