Research Progress of Cationic Reactive Diluents for Photopolymerization

doi:10.7517/j.issn.1674-0475.2016.06.491

Abstract

Abstract:

With the development of photopolymerization technology, the wide use of free radical photopolymerization had exhibited some drawbacks gradually. Compared with free radical photopolymerization,cationic photopolymerization exhibits several inherent advantages, such as, low shrinkage, strong adhesion, no oxygen inhibition, and so on. Reactive diluentas are one of important formulations of cationic photopolymerization, which has a notable effect on curing of formulations and the mechanical properties of the final product. So, exploiting reactive diluent with rapid curing has a vital significance. This paper introduces the mechanisms and properties of cationic reactive diluents. And the prospect and research directions of it are also presented.

Key words: cationic photopolymerization, reactive diluent, rapid curing

ZHANG Na, CHEN Yuan, NIE Jun, YANG Jinliang. Research Progress of Cationic Reactive Diluents for Photopolymerization[J]. Imaging Science and Photochemistry, 2016, 34(6): 491-504.

References

[1] Sang S L, Luciani A, Månson J A E. A rheological characterisation technique for fast UV-curable systems[J]. Progress in Organic Coatings, 2000,38(3-4):193-197.
[2] Wuertz C, Bismarck A, Springer J, K niger, R. Electrokinetic and mechanical characterization of UV induced crosslinked acrylic copolymers[J]. Progress in Organic Coatings, 1999,37(3):117-129.
[3] Fertier L, Koleilat H, Stemmelen M, Giani O. The use of renewable feedstock in UV-curable materials-A new age for polymers and green chemistry[J]. Progress in Polymer Science, 2013,38(6):932-962.
[4] Zhang W, Dong H N, Zhang T, Guo J B, Wei J.The effect of monomer structures on photopolymerization kinetics and volume shrinkage behavior for plasma display panel barrier rib[J]. Journal of Applied Polymer Science, 2012,125(1):77-87.
[5] 聂俊. 光聚合技术与应用[M]. 北京:化学工业出版社, 2009. 1-6. Nie J. Photopolymerization Technology and Application[M]. Beijing:Chemical Industry Press, 2009. 1-6.
[6] 陈用烈, 曾兆华, 杨建文. 辐射固化材料及其应用[M].北京:化学工业出版社, 2003. 22-25. Chen Y L, Zeng Z H, Yang J W. Application of UV-curingMaterial[M]. Beijing:Chemical Industry Press, 2003. 22-29.
[7] Balta D K, Arsu N, Yagci Y, Jockusch S, Turro N J. Thioxanthone-anthracene:a new photoinitiator for free radical polymerization in the presence of oxygen[J]. Macromolecules, 2007,40(12):4138-4141.
[8] Kloosterboer J G. Network Formation by Chain Crosslinking Photopolymerization and Its Applications in Electronics[M]. Springer Berlin Heidelberg, 1988. 27-35.
[9] Urabe H, Wakasa K, Yamaki M. Application of multifunctional base monomer to dental composite resins[J]. Journal of Materials Science Materials in Medicine, 1990,1(3):163-170.
[10] Anseth K S, Newman S M, Bowman C N. Polymeric dental composites:properties and reaction behavior of multimethacrylate dental restorations[J]. Biopolymers, 2006,122(1):177-217.
[11] Kristi S, Anseth, Deborah J. Polymerizations of multifunctional anhydride monomers to form highly crosslinked degradable networks[J]. Macromolecular Rapid Communications, 2001,22(8):564-572.
[12] 徐钦昌. 3-乙基-3-羟甲基氧杂环丁烷作为活性单体的紫外光固化材料研究[D]. 南昌:南昌大学, 2014. Xu Q C. Study on 3-ethyl-3-hydroxymethyl oxetane as the reactive monomer for UV-curing materials[D]. Nanchang:Nanchang University, 2014.
[13] 肖思煜. 紫外光固化涂料的发展状况[J]. 广州化工, 2005, 33(5):31-33. Xiao S Y. Progress of ultraviolet curing coatings[J]. Guangzhou Chemical Industry, 2005,33(5):31-33.
[14] 刘岚, 陈用烈. 一种新型的光固化活性稀释剂——乙烯基醚[J]. 高分子通报, 1997,(4):242-245. Liu L, Chen Y L. Viny ether-a new type of reactive diluents for photocuring[J]. Polymer Bulletin, 1997,(4):242-245.
[15] Ortyl J, Popielarz R. New photoinitiators for cationic polymerization[J]. Polimery, 2012,57(7-8):510-517.
[16] Sangermano M, Malucelli G, Priola A, Manea M. Synthesis and characterization of acrylate-oxetane interpenetrating polymer networks through a thermal-UV dual cure process[J]. Progress in Organic Coatings, 2006,55(3):225-230.
[17] Sangermano M, Malucelli G, Bongiovanni R, Priola A. Photopolymerization of oxetane based systems[J]. European Polymer Journal, 2004,40(2):353-358.
[18] 杨娟, 成佳辉, 任冬燕. UV固化涂料研究进展[J]. 广州化工, 2011,39(24):7-8. Yang J, Cheng J H, Ren D Y. The research development of UV curing coating[J]. Guangzhou Chemical Industry, 2011,39(24):7-8.
[19] Fang Y, Zou Y. Synthesis and photo-curing behaviors of silicon-containing (vinyl ether)-(allyl ether) hybrid monomers[J]. Polymer International, 2013,62(11):1624-1633.
[20] Sangermano M, Malucelli G, Morel F, Decker C, Priola A. Cationic photopolymerization of vinyl ether systems:influence of the presence of hydrogen donor additives[J]. European Polymer Journal, 1999,35(4):639-645.
[21] Sangermano M, Spera S, Bongiovanni R, Priola A, Busetto C. NMR investigation of UV-cured vinyl ether networks[J]. Macromolecular Chemistry & Physics, 2000,201(17):2441-2446.
[22] Sugihara S, Kawamoto Y, Maeda Y. Direct radical polymerization of vinyl ethers:reversible addition-fragmentation chain transfer polymerization of hydroxy-functional vinyl ethers[J]. Macromolecules, 2016,49:1563-1574.
[23] Crivello J V, L hden G. The preparation of novel 1-propenyl ethers and their cationic photopolymerization[J]. Journal of Polymer Science Part A Polymer Chemistry, 1996,34(10):2051-2062.
[24] 李伟, 庞玉莲, 邹应全. 乙烯基醚阳离子光固化单体[C].中国辐射固化会议, 2012. 186-196. Li W, Pang Y L, Zou Y Q. Cationic photocuring vinyl ether monomers[C]. RadTech China, 2012. 186-196.
[25] Crivello J V, Jo K D. Propenyl ethers. Ⅱ. Study of the photoinitiated cationic polymerization of propenyl ether monomers[J]. Journal of Polymer Science Part A Polymer Chemistry, 1993,31(31):1483-1491.
[26] Sasaki H, Rudizinskt J M, Kakuchi T. Photoinitiated cationic polymerization of oxetane formulated with oxirane[J]. Journal of Polymer Science Part A Polymer Chemistry, 1995,33(11):1807-1816.
[27] Askadskii A A, Afanas'Ev E S, Petunova M D,Barabanova A I, Goleneva L M, Kondrashchenko V I, Philippova O E. Structures and properties of nanocomposites based on a cured cycloaliphatic epoxy resin[J]. Polymer Science, 2014,56(3):318-329.
[28] Crivello J V, Lam J H W. Diaryliodonium salts, a new class of photoinitiators for cationic polymerization[J]. Macromolecules, 1977,10(6):1307-1315.
[29] Crivello J V, Lam J H W. Photoinitiated cationic polymerization with triarylsulfonium salts[J]. Journal of Polymer Science Polymer Chemistry Edition, 1996,34(16):3231-3253.
[30] Sasaki H, Crivello J V. The Synthesis, characterization, and photoinitiated cationic polymerizaton of difunctional oxetanes[J]. Journal of Macromolecular Science Part A, 1992,29(10):915-930.
[31] Verstegen E J K, Kloosterboer J G, Lub J. Synthesis and photopolymerization of oxetanes derived from bisphenol A[J]. Journal of Applied Polymer Science, 2005,98(4):1697-1707.
[32] 熊磊, 邓熙烺, 黄笔武. 对叔丁基酚缩水甘油醚作为稀释剂紫外光固化材料的制备及性能[J]. 南昌大学学报:工科版, 2015,(3):209-214. Xiong L, Deng X L, Huang B W. Preparation and properties of the UV-curing material with tert-butyl phenol glycidyl ether as diluent[J]. Journal of Nanchang University (Engineer & Technology Edition), 2015,(3):209-214.
[33] 黄笔武, 姜安坤, 翁子骧, 杨志宏. 正丁基缩水甘油醚的合成及作为阳离子型UV固化稀释剂的研究[J]. 精细石油化工, 2010,27(4):23-26. Huang B W, Jiang A K, Weng Z X, Yang Z H. Synthesis and properties of n-butyl glycidyl ether as cationic type UV-curing diluent[J]. Speciality Petrochemicals, 2010,27(4):23-26.
[34] Falk B, Vallinas S M, Crivello J V. Monitoring photopolymerization reactions with optical pyrometry[J]. Journal of Polymer Science Part A Polymer Chemistry, 2003,41(4):579-596.
[35] Crivello J V. Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization[J]. Journal of Polymer Science Part A Polymer Chemistry, 2006,44(21):6435-6448.
[36] Crivello J V, Falk B, Zonca M R. Photoinduced cationic ring-opening frontal polymerizations of oxetanes and oxiranes[J]. Journal of Polymer Science Part A Polymer Chemistry, 2004,42(7):1630-1646.
[37] Crivello J V. Synergistic effects in hybrid free radical/cationic photopolymerizations[J]. Journal of Polymer Science Part A Polymer Chemistry, 2007,45(45):3759-3769.
[38] Ryu C Y, Spencer M J, Crivello J V. Involvement of supramolecular complexes in the capture and release of protonic acids during the cationic ring-opening polymerization of epoxides[J]. Macromolecules, 2012,45(45):2233-2241.
[39] Crivello J V, Bulut U. Dual photoand thermally initiated cationic polymerization of epoxy monomers[J]. Journal of Polymer Science Part A Polymer Chemistry, 2006,44(44):6750-6764.
[40] Crivello J V. Cationic photopolymerization of alkyl glycidyl ethers[J]. Journal of Polymer Science Part A Polymer Chemistry, 2006,44(44):3036-3052.
[41] And U B, Crivello J V. Investigation of the reactivity of epoxide monomers in photoinitiated cationic polymerization[J]. Macromolecules, 2005,38(9):3584-3595.
[42] Crivello J V. Hybrid free radical/cationic frontal photopolymerizations[J]. Journal of Polymer Science Part A Polymer Chemistry, 2007,45(18):4331-4340.
[43] Crivello J V, Ortiz R A. Design and synthesis of highly reactive photopolymerizable epoxy monomers[J]. Journal of Polymer Science Part A Polymer Chemistry, 2001,39(14):2385-2395.
[44] Rajaraman S K, And W A M, Crivello J V. Novel hybrid monomers bearing cycloaliphatic epoxy and 1-propenyl ether groups[J]. Macromolecules, 1999,32(1):36-47.
[45] Crivello J V, Ortiz R A. Synthesis of epoxy monomers that undergo synergistic photopolymerization by a radical-induced cationic mechanism[J]. Journal of Polymer Science Part A Polymer Chemistry, 2001,39(20):3578-3592.
[46] Ortiz R A, García G A. Synthesis of novel highly reactive silicone-epoxy monomers for cationic photopolymerizations[J]. Polymer, 2005,46(24):10663-10671.
[47] And J V C, Song S. Synthesis and cationic photopolymerization of novel monomers based on dicyclopentadiene[J]. Chemistry of Materials, 2000,12(12):3674-3680.
[48] Crivello J V, Song S. The synthesis and cationic photopolymerization of monomers based on dicyclopentadiene[J]. Journal of Polymer Science Part A Polymer Chemistry, 1999,37(16):3427-3440.
[49] Rajaraman S K, And W A M, Crivello J V. Novel hybrid monomers bearing cycloaliphatic epoxy and 1-propenyl ether groups[J]. Macromolecules, 1999,32(1):36-47.
[50] 谢王付. 3-乙基-3-烯丙基甲氧基氧杂环丁烷的合成及其应用研究[D]. 南昌:南昌大学, 2015. Xie W F. Study on the synthesis and application of 3-ethyl-3-allyloxymethyl oxetane[D].Nanchang:Nanchang University, 2015.
[51] 邓冲, 谢王付, 黄笔武, 万时策, 谌伟庆, 徐钦昌, 胡开创. 氧杂环丁烷/丙烯酸酯混杂体系的光固化性能研究[D]. 南昌:南昌大学, 2014. Deng C, Xie W F, Huang B W, Wan S C, Chen W Q, Xu Q C, Hu K C. Study on the properties of oxetane/acrylate UV-cured hybrid system[D]. Nanchang:Nanchang University, 2014.
[52] 万时策, 黄笔武, 杜志鹏, 雍涛, 韩文娟. 新型阳离子光固化活性单体3,3'-[1,4-丁基双(氧基亚甲基)]-双-(3-乙基)氧杂环丁烷的合成[J]. 影像科学与光化学, 2016,34(2):181-189. Wan S C, Huang B W, Du Z P, Yong T, Han W J. Study on the synthesis of 3,3、-[1,4-butanediylbis(oxymethylene)] bis[(3-ethyl)oxetane] for the novel cationic curing monomer[J]. Imaging Science and Photochemistry, 2016,34(2):181-189.
[53] Vong J, Crivello J V, Bulut U. Photoactivated cationic ring-opening frontal polymerizations of oxetanes[J]. Designed Monomers & Polymers, 2005,8(6):517-531.
[54] Crivello J V. Investigations of the reactivity of "kick-started" oxetanes in photoinitiated cationic polymerization[J]. Journal of Polymer Science Part A Polymer Chemistry, 2015,53(4):586-593.
[55] 刘安昌, 夏强, 张良, 李高峰. 阳离子光固化活性单体氧杂环丁烷的合成[J]. 武汉工程大学学报, 2010,32(9):14-16. Liu A C, Xia Q, Zhang L, Li G F. Synthesis of oxetanes for the cationic curing monomer[J]. Journal of Wuhan Institute of Technology, 2010,32(9):14-16.
[56] James V, Crivello J V. "Kick-Starting'" oxetane photopolymerizations[J]. Journal of Polymer Science Part A Polymer Chemistry, 2014,52(20):2934-2946.
[57] Crivello J V. Investigation of the photoactivated frontal polymerization of oxetanes using optical pyrometry[J]. Polymer, 2005,46(26):12109-12117.
[58] Bulut U, Crivello J V. Reactivity of oxetane monomers in photoinitiated cationic polymerization[J]. Journal of Polymer Science Part A Polymer Chemistry, 2005,43(43):3205-3220.
[59] Crivello J V, Falk B, Zonca M R. Photoinduced cationic ring-opening frontal polymerizations of oxetanes and oxiranes[J]. Journal of Polymer Science Part A Polymer Chemistry, 2004,42(7):1630-1646.
[60] Crivello J V. Vinyl epoxide accelerators for the photoin-itiated cationic polymerization of oxetane monomers[J]. Polymer, 2015,64:227-233.
[61] Crivello J V. Aryl epoxides as accelerators for the photopolymerization of oxetane monomers[J]. Journal of Macromolecular Science Part A, 2015,52(5):336-344.
[62] 蹇钰. 光聚合收缩的研究[D].北京:北京化工大学, 2013. Jian Y. Shrinkage of photopolymerization[D]. Beijing:Beijing University of Chemical Technology, 2013.
[63] Nuyken O, B hner R, Erdmann C. Oxetane photopolymerization-a system with low volume shrinkage[J]. Macromolecular Symposia, 1996,107(1):125-138.
[64] Kloosterboer J G. Network Formation by Chain Crosslinking Photopolymerization and Its Applications in Electronics[M]. Springer Berlin Heidelberg, 1988.45-61.
[65] Verstegen E J K, Kloosterboer J G, Lub J. Synthesis and photopolymerization of oxetanes derived from bisphenol A[J]. Journal of Applied Polymer Science, 2005,98(4):1697-1707.
[66] Crivello J V, Jang M. Synthesis of novel silicon-containing monomers for photoinitiated cationic polymerization[C]. ACS Symposium Series, 2009:27-36.
[67] Crivello J V, Sasaki H. Synthesis and photopolymerization of silicon-containing multifunctional oxetane monomers[J]. Journal of Macromolecular Science Part A, 1993,(2-3):173-187.
[68] Sangermano M, Bongiovanni R, Malucelli G, Priola A, Thomas R R, Medsker R E, Kim Y, Kausch C M. Synthesis and cationic photopolymerization of a new fluorinated oxetane monomer[J]. Polymer, 2004,45(7):2133-2139.