双官能度单组分光引发剂的制备及其光引发活性研究

doi:10.7517/j.issn.1674-0475.2016.06.505

影像科学与光化学 ›› 2016, Vol. 34 ›› Issue (6): 505-512.DOI: 10.7517/j.issn.1674-0475.2016.06.505

双官能度单组分光引发剂的制备及其光引发活性研究

简凯¹, 李东兵², 周金娣⁴, 杨金梁², 聂俊³

1. 北京化工大学材料科学与工程学院, 北京 100029;
2. 北京化工大学常州先进材料研究院, 江苏常州 213000;
3. 北京化工大学理学院, 北京 100029;
4. 海门自来水公司分析实验室, 江苏南通 226100

收稿日期:2016-05-29 出版日期:2016-11-15 发布日期:2016-11-15
通讯作者: 杨金梁, 聂俊

Synthesis of Bifunctional One-component Photoinitiator and Its Initiatiating Activity

JIAN Kai¹, LI Dongbing², ZHOU Jindi⁴, YANG Jinliang², NIE Jun³

1. School of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China;
2. Changzhou Institute of Advanced Materials Research, Beijing University of Chemical Technology, Changzhou 213000, Jiangsu, P. R. China;
3. School of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China;
4. Analytical Laboratory of Haimen City Water Company, Nantong 226100, Jiangsu, P. R. China

Received:2016-05-29 Online:2016-11-15 Published:2016-11-15

摘要/Abstract

摘要：

本文利用4-甲基二苯甲酮、哌嗪等原料合成了一种双官能度的单组分光引发剂（MBPPA），其分子结构中具有两个二苯甲酮基团。通过紫外光谱研究了光引发剂的紫外吸收和光降解性能，并利用实时红外测试了光引发剂的光引发活性以及不同单体对光聚合动力学的影响。结果表明，在光照10 min后，MBPPA在257.2 nm处的吸光度降低了18.76%，光降解速度明显高于MBP。当光强为50 mW·cm^-2时，0.2%（摩尔分数）MBPPA单独引发乙氧基乙氧基丙烯酸乙酯（EOEOEA）聚合的转化率可达90%。在同等条件下，多官能度丙烯酸酯单体的聚合速率要明显高于单官能度丙烯酸酯单体，但其转化率有所降低。

关键词: 光聚合, 光引发剂, 二苯甲酮, 单组分光引发剂

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

简凯, 李东兵, 周金娣, 杨金梁, 聂俊. 双官能度单组分光引发剂的制备及其光引发活性研究[J]. 影像科学与光化学, 2016, 34(6): 505-512.

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.

参考文献

[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.

双官能度单组分光引发剂的制备及其光引发活性研究

Synthesis of Bifunctional One-component Photoinitiator and Its Initiatiating Activity

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