Synthesis of Bifunctional One-component Photoinitiator and Its Initiatiating Activity

doi:10.7517/j.issn.1674-0475.2016.06.505

Abstract

Abstract:

MBPPA, a one-component photoinitiator with two benzophenone groups, was synthesized. The properties of UV absorption and photodegradation were studied by UV absorption spectra. The initiation activity of photoinitiator and the effects of monomer on the polymerization kinetics were investigated by real-time infrared spectroscopy. The results show that the intensity of the absorption peak at 257.2 nm of MBPPA decreased 18.76% after irradiating for 10 min, which is better than MBP. The conversion rate of 2-(2-ethoxyethoxy)ethylacrylate initiated by 0.2%(mole fraction) MBPPA alone can reach 90% at 50 mW·cm^-2. The more functionality of monomer has, the higher of polymerization rate and the lower of the double bond conversion are.

Key words: photopolymerization, photoinitiator, benzophenone, one-component photoinitiator

JIAN Kai, LI Dongbing, ZHOU Jindi, YANG Jinliang, NIE Jun. Synthesis of Bifunctional One-component Photoinitiator and Its Initiatiating Activity[J]. Imaging Science and Photochemistry, 2016, 34(6): 505-512.

References

[1] Ibrahim A, Stefano L D, Tarzi O, Tar H, Ley C, Allonas X. High-performance photoinitiating systems for free radical photopolymerization. Application to holographic recording[J]. Photochemistry and photobiology, 2013,89:1283-1290.
[2] Xu F, Yang J L, Gong Y S, Ma G P, Nie J. A fluorinated photoinitiator for surface oxygen inhibition resistance[J]. Macromolecules, 2012,45:1158-1164.
[3] Balta D K, Cetiner N, Temel G, Turgut Z, Arsu N. An annelated thioxanthone as a new type II initiator[J]. Journal of Photochemistry and Photobiology A:Chemistry, 2008,199:316-321.
[4] Jiang X S, Xu H J, Yin J. Copolymeric dendritic macrophotoinitiators[J]. Polymer, 2005,46:11079-11084.
[5] Cokbaglan L, Arsu N, Yagci Y, Jockusch S, Turro N J. 2-Mercaptothioxanthone as a novel photoinitiator for free radical polymerization[J]. Macromolecules, 2003,36(8):2649-2653.
[6] Balta D K,Arsu N,Yagci Y,Jockusch S, Turro N J.Thioxanthone-anthracene:a new photoinitiator for free radicalpolymerization in the presence of oxygen[J]. Macromolecules, 2007,40(12):4138-4141.
[7] Tunc D, Yagci Y. Thioxanthone-ethylcarbazole as a soluble visible light photoinitiator for free radical and free radical promoted cationic polymerizations[J]. Polymer Chemistry, 2011,2:2557-2563.
[8] Kork S, Yilmaz G, Yagci Y. Poly(vinyl alcohol)-thioxanthone as one-component type II photoinitiator for free radical polymerization in organic and aqueous media[J]. Macromolecular Rapid Communication, 2015,36:923-928.
[9] Yagci Y, Jockusch S, Turro N J. Photoinitiated polymerization:advances, challenges, and opportunities[J]. Macromolecules, 2010,43(15):6245-6260.
[10] Aydin M, Arsu N, Yagci Y, Jockusch S, Turro N J. Mechanistic study of photoinitiated free radical polymerization using thioxanthone thioacetic acid as one-component type II photoinitiator[J]. Macromolecules, 2005,38(10):4133-4138.
[11] Cokbaglan L, Arsu N, Yagci Y, Jockusch S, Turro N J.2-Mercaptothioxanthoneas a novel photoinitiator for free radical polymerization[J]. Macromolecules, 2003,36(8):2649-2653.
[12] Corrales T, Catalina F, Peinado C, Allenb N S, Rufsc A M, Buenoc C, Encinas M V. Photochemical study and photoinitiation activity of macroinitiators based on thioxanthone[J]. Polymer, 2002,43:4591-4597.
[13] Jiang X S, Luo X W, Yin J. Polymeric photoinitiators containing in-chain benzophenone and coinitiators amine:effect of the structure of coinitiator amine on photopolymerization[J]. Journal of Photochemistry and Photobio-logy A:Chemistry, 2005,174:165-170.
[14] Jiang X S, Xu H J, Yin J. Polymeric amine bearing side-chain thioxanthone as a novel photoinitiator for photopolymerization[J]. Polymer, 2004,45:133-140.
[15] Wang K M, Lu Y H, Chen P H, Shi J S, Wang H N, Yu Q. Novel one-component polymeric benzophenone photoinitiator containing poly (ethylene glycol) as hydrogen donor[J]. Materials Chemistry and Physics, 2014,143:1391-1395.
[16] 聂俊. 光聚合技术与应用[M]. 北京:化学工业出版社, 2008. 55. Nie J. Technology and Application of Photopolymerization[M]. Beijing:Chemical Industry Press, 2008. 55.
[17] Cheng L L, Zhang Y, Shi W F.Photoinitiating behavior of benzophenone derivatives covalently bonded tertiary amine group for UV-curing acrylate systems[J]. Polymers for Advanced Technologies, 2012,23:669-676.
[18] Wu G Q, Shi S Q, Xiao P, Nie J. Synthesis and characte-rization of aliphatic amine co-initiator with different chain length for photopolymerization of dimethacrylate[J]. Journal of Photochemistry and Photobiology A:Chemistry, 2007,188:260-266.
[19] Han Y, Spangler L H. Use of isosbestic points for determination of quantum efficiency in transient absorption spectroscopy[J]. Journal of Physical Chemistry A, 2002,106:1701-1707.
[20] Scherzer T, Decker U. Real-time FTIR-ATR spectroscopy to study the kinetics of ultrafast photopolymerization reactions induced by monochromatic UV light[J]. Vibrational Spectroscopy, 1999,19:385-398.
[21] Li S J, He Y,Nie J. Photopolymerization of hybrid monomer 3-(1-propenyl)oxypropyl acrylate[J]. Journal of Photochemistry and Photobiology A:Chemistry, 2007,191(1):25-31.
[22] Temel G, Enginol B, Aydin M, Balta D K, Arsu N. Photopolymerization and photophysical properties of amine linked benzophenone photoinitiator for free radical polyme-rization[J]. Journal of Photochemistry and Photobiology A:Chemistry, 2011,219(1):26-31.
[23] 徐菲. 含氟光引发剂的合成及性能研究[D]. 北京:北京化工大学, 2012. Xu F. Synthesis and properties research of fluorine-containing photoinitiators[D]. Beijing:Beijing University of Chemical Technology, 2012.
[24] Yang J L, Shi S Q, Xu F, Nie J. Synthesis and photopolymerization kinetics of benzophenonesesamol one-component photoinitiator[J]. Photochemical & Photobiological Sciences, 2013,12:323-329.