journal article·2013-04-24Open access

Photopolymerization Reactions: On the Way to a Green and Sustainable Chemistry

Mohamad Tehfe, Fanny Louradour, Jacques Lalevée, Jean-Pierre Fouassier

Applied Sciences· Volume 3· Issue 2

Abstract

The present paper reviews some aspects concerned with the development of green technologies in the photopolymerization area: use of visible light sources (Xe and Hg-Xe lamps, diode lasers), soft irradiation conditions (household lamps: halogen lamp, fluorescence bulbs, LED bulbs), sunlight exposure, development of very efficient photoinitiating systems and use of renewable monomers. The drawbacks/breakthroughs encountered when going on the way of a greener approach are discussed. Examples of recent achievements are presented.
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Research context

OpenAlex topics: Photopolymerization techniques and applications · Advanced Photocatalysis Techniques

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Institut de Science des Matériaux de Mulhouse IS2M–UMR 7361–UHA; 15, rue Jean Starcky, 68057 Mulhouse Cedex, France

References (100+)

Show source-provided references
1. Hoyle, C.E., and Kinstle, J.F. (1990). Radiation Curing of Polymeric Materials, American Chemical Society.10.1021/bk-1990-0417 ↗
2. Fouassier, J.P., and Rabek, J.F. (1990). Lasers in Polymer Science and Technology: Applications, CRC Press.
3. Pappas, S.P. (1992). UV-Curing: Science and Technology, Plenum Press.
4. Fouassier, J.P., and Rabek, J.F. (1993). Radiation Curing in Polymer Science and Technology, Chapman & Hall.10.1007/978-94-011-1876-7 ↗
5. Krongauz, V., and Trifunac, A. (1994). Photoresponsive Polymers, Chapman and Hall.
6. Reiser, A. (1989). Photoreactive Polymers: The Science and Technology of Resists, Wiley.
7. Fouassier, J.P. (1995). Photoinitiation, Photopolymerization, Photocuring: Fundamentals and Applications, Carl Hanser GmbH.
8. Davidson, S. (1999). Exploring the Science, Technology and Application of UV and EB Curing, SITA Technology Ltd.
9. Neckers, D.C. (1999). UV and EB at the Millenium, SITA Technology Ltd.
10. Bradley, G. (1999). Photoinitiators for Free Radical, Cationic and Anionic Photopolymerization, Surface Coatings Technology Series; Wiley.
11. Dietliker, K. (2002). A Compilation of Photoinitiators Commercially Available for UV Today, SITA Technology Ltd.
12. Belfied, K.D., and Crivello, J.V. (2003). Photoinitiated Polymerization, American Chemical Society.10.1021/bk-2003-0847 ↗
13. Fouassier, J.P. (2006). Photochemistry and UV Curing, Research Signpost.
14. Allen, N.S. (2010). 14. Photochemistry and Photophysics of Polymer Materials, Wiley.10.1002/9780470594179 ↗
15. Fouassier, J.P., and Allonas, X. (2010). Basics of Photopolymerization Reactions, Research Signpost.
16. Green, W.A. (2010). Industrial Photoinitiators, CRC Press.10.1201/9781439827468 ↗
17. Scranton, A.B., and Bowman, A. (1997). Photopolymerization: Fundamentals and Applications, Americal Chemical Society.10.1021/bk-1997-0673 ↗
18. Mishra, M.K., and Yagci, Y. (2009). Handbook of Vinyl Polymers, CRC Press.
19. Fouassier, J.P., and Lalevée, J. (2012). Photoinitiators for Polymer Synthesis: Scope, Reactivity and Efficiency, Wiley VCH.10.1002/9783527648245 ↗
20. Kinetics characterization of a novel photopolymerizable siloxane-modified acrylic resin10.1016/j.tca.2010.06.001 ↗
21. Photopolymerization kinetics of an epoxy-based resin for stereolithography10.1002/app.20347 ↗
22. Time–temperature and time-irradiation intensity superposition for photopolymerization of an epoxy based resin10.1016/j.polymer.2005.06.111 ↗
23. Temperature evolution during stereolithography building with a commercial epoxy resin10.1002/pen.20488 ↗
24. Influence of stone particles on the rheological behavior of a novel photopolymerizable siloxane-modified acrylic resin10.1002/app.34201 ↗
25. Rheological and kinetic characterization of UV photopolymerizable formulations as a function of the boehmite nanoparticle content10.2174/1874088X01206010068 ↗
26. Factors influencing photo curing kinetics of novel UV-cured siloxane-modified acrylic coatings: Oxygen inhibition and composition10.1016/j.tca.2012.01.023 ↗
27. Mesoporous graphitic carbon nitride as a heterogeneous visible light photoinitiator for radical polymerization10.1021/mz3004743 ↗
28. Thioxanthone–diphenyl anthracene: Visible light photoinitiator10.1021/ma202168m ↗
29. Counteranion sensitization spproach to photoinitiated free radical polymerization10.1021/ma3000169 ↗
30. Naphthodioxinone-1,3-benzodioxole as photochemically masked one-component Type II photoinitiator for free radical polymerization10.1002/pola.26034 ↗
31. Photopolymerization and photophysical properties of amine linked benzophenone photoinitiator for free radical polymerization10.1016/j.jphotochem.2011.01.012 ↗
32. A thioxanthone-based visible photoinitiator10.1002/pola.24846 ↗
33. The investigation of photoinitiated polymerization of multifunctional acrylates with TX-BT by Photo-DSC and RT-FTIR10.1016/j.porgcoat.2010.10.010 ↗
34. Type II photoinitiator substituted zinc phthalocyanine: Synthesis, photophysical and photopolymerization studies10.1016/j.jlumin.2012.12.025 ↗
35. The 2-benzoyl xanthone/triethylamine system as a type II photoinitiator: A laser flash photolysis and computational study10.1016/j.jphotochem.2011.02.028 ↗
36. Polymerization of HEMA photoinitiated by the Safranine/diphenylborinate system10.1016/j.jphotochem.2012.12.007 ↗
37. Unexpected visible-light-induced free radical photopolymerization at low light intensity and high viscosity using a titanocene photoinitiator10.1002/app.38259 ↗
38. Synthesis of novel photochromic spiropyran dyes containing quaternary ammonium salt or cinnamoyl moiety and their properties as photoinitiators10.1002/app.36419 ↗
39. Allen, N.S. (2010). Handbook on Photochemistry and Photophysics of Polymer Materials, Wiley.10.1002/9780470594179 ↗
40. Allen, N.S. (2010). Handbook on Photochemistry and Photophysics of Polymer Materials, Wiley.10.1002/9780470594179 ↗
41. Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator10.1039/c2pp25241d ↗
42. Toward the photoinduced reactivity of 1,5-diphenylpenta-1,4-diyn-3-one (DPD): Real-time investigations by magnetic resonance10.1021/ma901570h ↗
43. Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide—A tailor-made photoinitiator for dental adhesives10.3762/bjoc.6.26 ↗
44. Photoinitiating monomers based on di- and triacryloylated hydroxylamine derivatives10.1002/pola.23156 ↗
45. Synthesis and structure-activity relationship of several aromatic ketone-based two-photon initiators10.1002/pola.24806 ↗
46. Photoinitiated polymerization: advances, challenges, and opportunities10.1021/ma1007545 ↗
47. Free radical formation in three-component photoinitiating systems10.1016/j.polymer.2012.03.027 ↗
48. Photoreactive s-triazine as crosslinking agents for UV-crosslinkable acrylic pressure-sensitive adhesives10.1002/app.33536 ↗
49. Studies on an argon laser-induced photopolymerization employing both mono- and bischromophoric hemicyanine dye-borate complex as a photoinitiator. Part III10.1002/app.32348 ↗
50. Novel N-ethyl-2-styrylquinolinum iodides as sensitizers in photoinitiated free radical polymerization of trimethylolopropane triacrylate (TMPTA)10.1002/app.30125 ↗
51. Ackrine, W.J. (2010). Polymer Initiators, Nova Science Publishers, Inc.. chapter 8.
52. Pauloskas, I.O., and Urbonas, L.A. (2011). Radical Polymerization: New Developments, Nova Science Publishers, Inc.. chapter 7.
53. Three-component photoinitiating systems: Towards innovative tailor made high performance combinations
54. Studer, A., and Chatgilialoglou, C. (2012). In Encyclopedia of Radicals in Chemistry, Biology and Materials, Wiley. chapter 2.10.1002/9781119953678 ↗
55. Wyman, E., and Skief, M.C. (2009). Organosilanes: Properties, Performance and Applications, Nova Science Publishers. chapter 6.
56. Fouassier, J.P., and Lalevée, J. New Developments in Chromophore Research, Nova Science Publishers. in press.
57. Lalevée, J., Tehfe, M.A., Dumur, F., Gigmes, D., Morlet-Savary, F., Graff, B., and Fouassier, J.P. (2013). Green light induced cationic ring opening polymerization reactions: Perylene bis-dicarboximides as efficient photosensitizers. Macromol Chem. Phys.
58. A new cleavable photoinitiator architecture with huge molar extinction coefficients for polymerization in the 340–420 nm range10.1021/ma3024359 ↗
59. Long wavelength cationic photopolymerization in aerated media: A remarkable titanocene/tris(trimethylsilyl)silane/onium salt photoinitiating system10.1021/ma9016696 ↗
60. New thioxanthone and xanthone derivative based on silyl radical chemistry10.1039/C0PY00392A ↗
61. Pyrromethene derivatives in three-component photoinitiating systems for free radical photopolymerization10.1002/pola.24039 ↗
62. New insights in radical and cationic polymerization upon visible light exposure: Role of novel photoinitiator systems based on the pyrene chromophore10.1039/C2PY20950K ↗
63. Telitel, S., Blanchard, N., Schweitzer, S., Morlet-Savary, F., Graff, B., Fouassier, J.P., and Lalevée, J. (2013). Bodipy derivatives and boranil as new photoinitiating systems of cationic polymerization exhibiting a tunable absorption in the 400–600 nm spectral range. Polymer.10.1016/j.polymer.2013.02.013 ↗
64. Trifunctional photoinitiators based on a triazine skeleton for visible light sources and UV LED induced polymerizations10.1021/ma301931p ↗
65. Photopolymerization of cationic monomers and acrylate/divinylether blends under visible lights using pyrromethene dyes10.1021/ma301293m ↗
66. Pyridinium salts: New systems for photopolymerization reactions upon visible light exposure10.1016/j.eurpolymj.2012.10.010 ↗
67. Dye photosensitized cationic ring-opening polymerization: search for new dye skeletons10.1016/j.polymer.2012.08.067 ↗
68. A breakthrough for long wavelength absorbing photoinitiating systems under soft irradiation conditions based on violanthrone derivatives10.1021/ma2017265 ↗
69. Cationic photosensitive formulations based on the silyl radical chemistry for green and red diode laser exposure10.1039/C1PY00460C ↗
70. Household LED irradiation under air: Cationic polymerization using iridium or ruthenium complex photocatalysts10.1007/s00289-011-0541-9 ↗
71. Lalevée, J., Dumur, F., Mayer, C.R., Gigmes, D., Nasr, G., Tehfe, M.A., Morlet-Savary, F., Telitel, S., Graff, B., and Fouassier, J.P. (2012). Photopolymerization of N-vinylcarbazole using visible-light harvesting iridium complexes as photoinitiators. Macromolecules.10.1021/ma3005229 ↗
72. Iridium complexes incorporating coumarin moiety as photocatalysts for ring opening photopolymerizations10.1016/j.polymer.2012.05.009 ↗
73. Design of new Type I & Type II photoinitiators possessing highly coupled pyrene-ketone moieties10.1039/c3py21079k ↗
74. Light harvesting organic photoinitiators of polymerization10.1002/marc.201200578 ↗
75. Organic photocatalyst for polymerization reactions: 9,10-bis[(triisopropylsilyl)ethynyl] anthracene10.1021/mz200140y ↗
76. Polyaromatic structures as organophotocatalysts for efficient dual radical/cationic photopolymerizations under visible lights and interpenetrated polymer networks synthesis10.1021/ma300760c ↗
77. Recent advances in sunlight induced polymerization: Role of new photoinitiating systems based on the silyl chemistry10.1039/C1PY00073J ↗
78. Kinetics of photocrosslinking reactions of a DCPA/EA matrix in the presence of thiols and acrylates10.1002/(SICI)1099-0518(19970915)35:12<2333::AID-POLA2>3.0.CO;2-W ↗
79. Use of α-diketones as visible photoinitiators for the photocrosslinking of waterborne latex paints10.1002/pola.10407 ↗
80. Interpenetrating polymer networks. II. Sunlight-induced polymerization of multifunctional acrylates10.1002/(SICI)1097-4628(19981212)70:11<2269::AID-APP21>3.0.CO;2-D ↗
81. Syntheses and cured films properties of UV-autocurable BTDA-based multiacrylate resins10.1002/app.1994.070511106 ↗
82. Synthesis and properties of ultraviolet-curable resins via a thio–ene (thiol and allyl) addition reaction10.1002/app.11117 ↗
83. Zero VOC sunlight curable coatings
84. Performance analysis of acylphosphine oxides in photoinitiated polymerization10.1016/S0032-3861(01)00221-X ↗
85. Photochemical preparation of polymer-clay composites10.1016/j.clay.2003.11.005 ↗
86. Possibilities for promoting cationic polymerization by common sources of free radicals10.1016/0032-3861(78)90073-3 ↗
87. Lichtinitiierte polymer- und polymerisationsreaktionen. photoinduzierte zersetzung von diaryliodonium- und triarylsulfoniumsalzen durch benzoinderivate und benzilketale10.1002/zfch.19840240104 ↗
88. Acylphosphine oxides as free radical promoters in cationic polymerizations10.1002/marc.1987.030080408 ↗
89. Long wavelength photoinitiated cationic polymerization using diphenyliodonium salt and catena-poly (phenyl-4-phenylphenylsilicon)10.1016/0032-3861(93)90101-F ↗
90. Mechanistic and kinetic studies on the photoinitiated polymerization of tetrahydrofuran10.1002/pola.1988.080260717 ↗
91. Visible and long-wavelength photoinitiated cationic polymerization10.1002/1099-0518(20010201)39:3<343::AID-POLA1001>3.0.CO;2-J ↗
92. Free radical promoted cationic polymerization by using bisacylphosphine oxide photoinitiators: Substituent effect on the reactivity of phosphinoyl radicals10.1016/j.polymer.2003.09.020 ↗
93. Radical-promoted visible light photoinitiated cationic polymerization of epoxides10.1080/10601320902797707 ↗
94. Photoinitiated cationic polymerization using O-phthaldehyde and pyridinium salt10.1002/pola.1995.080330907 ↗
95. Externally stimulated initiator systems for cationic polymerization10.1016/S0079-6700(98)00010-0 ↗
96. A quinoxaline derivative as a long wavelength photosensitizer for diaryliodonium salts10.1002/pola.23779 ↗
97. A new visible light sensitive photoinitiator system for the cationic polymerization of epoxides10.1002/pola.23203 ↗
98. Curcumin: A naturally occurring long-wavelength photosensitizer for diaryliodonium salts10.1002/pola.21017 ↗
99. Green bulb lamp induced cationic photopolymerization reactions under air
100. Oxygen mediated and wavelength tunable cationic photopolymerization reactions under air and low Intensity: A new concept10.1016/j.porgcoat.2010.09.014 ↗