The Research and Present Situation of Cyclic Acetals in Photopolymerization

doi:10.7517/j.issn.1674-0475.2013.02.003

Abstract

Abstract: Cyclic acetals, a kind of photo-sensitive compounds, were widely investigated during the 1960s.However, the drawbacks of cyclic acetals, such as the narrow range of absorption wavelength and the low initiation efficiency, had limited the development in the late 20^th century. Nevertheless, in the recent five years, cyclic acetals such as 1,3-benzodioxole have drawn renewed attention in photopolymerization, especially in the field of photopolymerized biomaterials, since cyclic acetals could be used as coinitiator so as to increase the initiation efficiency or decrease the toxicity of photoinitiating system. In this paper, the photopolymerization behavior of cyclic acetals has been systematically described, and the research progress of cyclic acetals as photoinitiator or co-initiator has also been discussed in detail.

Key words: cyclic acetals, 1,3-benzodioxole, photopolymerization, photoinitiator

CLC Number:

YANG Jin-liang, WANG Ke-min, NIE Jun. The Research and Present Situation of Cyclic Acetals in Photopolymerization[J]. Imaging Science and Photochemistry, 2013, 31(2): 103-116.

References

[1] Fouassier J P. Photoinitiation, Photopolymerization and Photocuring[M]. Munich:Hanser Verlag, 1995.
[2] Rabek J F. Mechanisms of Photophysical Processes and Photochemical Reactions in Polymers, Theory and Applications[M].New York:Wiley,1987.
[3] Davidson R S. Exploring the Science, Technology and Applications of UVand EB Curing[M].London: SITA Technology Ltd., 1999.
[4] Dietliker K. Chemistry and Technology of UV and EB Formulations for Coatings, Inks and Paints[M]. London:SITA Technology Ltd, 1991.
[5] Pappas S P. UV Curing Science and Technology[M]. Norwalk: Technology Marketing Corp., 1978.
[6] Arsu N, Davidson R S, Holman R. Factors affecting the photoyellowing which occurs during the photoinitiated polymerization of acrylates[J]. J. Photochem. Photobiol. A: Chem., 1995, 87: 169-175.
[7] Weisburger E K, Russfield A B, Hamburger F, et al. Testing of twenty-one environmental aromatic amine or derivatives for long-term toxicity or carcinogenicity[J]. Environ. Pathol. Toxicol., 1978, 2: 325-356.
[8] Albrecht W N, Stephenson R L. Health hazards of tertiary amine catalysts[J]. Scand J. Work Environ. Health, 1988, 14: 209-219.
[9] Nagao M, Wakabayashi K, Ushijima T, et al. Human exposure to carcinogenic heterocyclic amines and their mutational fingerprints in experimental animals[J]. Environ. Health Persp. (Suppl), 1996, 104: 497-501.
[10] Bowen R L, Argentar H. Amine accelerators for methacrylate resin systems[J]. J. Dent. Res., 1971, 50: 923.
[11] Bowen R L, Argentar H. Tertiary aromatic amine accelerators with molecular weights above 400[J]. J. Dent. Res., 1972, 51:473.
[12] Nie J, Bowman C N. Synthesis and photopolymerization of N,N'-dimethyl,-N,N'-di(methacryloxy ethyl)-1,6-hexanediamine as a polymerizable amine coinitiator for dental restorations[J]. Biomaterials, 2002, 23(4): 1221-1226.
[13] Ahn K D, Han D K, Lee S H, et al. New aromatic tert-amines for application as photoinitiator components in photocurable dental materials[J]. Macromol. Chem. Phys., 2003, 204: 1628-1635.
[14] 吴刚强, 肖浦,史素青,等. 樟脑醌/乙二醇-3-吗啡啉基丙酸酯甲基丙烯酸酯引发牙科复合树脂的光聚合动力学研究[J]. 感光科学与光化学, 2007, 25(2): 130-135. Wu G Q, Xiao P, Shi S Q,et al. Kinetics Study of dental composite initiated by camphorquinone/ethylene glycol 3-morpholine-propionate methacrylate[J]. Photographic Science and Photochemistry, 2007, 25(2): 130-135.
[15] 孙梦洲,何勇,吴刚强,等. 二芳酮-可聚合胺紫外光引发1,6-己二醇二丙烯酸酯聚合的动力学研究[J]. 感光科学与光化学, 2007, 25(1): 41-49. Sun M Z, He Y,Wu G Q, et al. Photopolymerization of 1,6-Hexanediol Diacrylate Initiated by Diarylketone/Polymerizable Amine[J]. Photographic Science and Photochemistry, 2007, 25(1): 41-49.
[16] Elad D, Youssefyeh D R. The photochemical conversion of acetals to carboxylic esters [J]. Tetrahedron Lett., 1963, 30: 2189.
[17] Walling C. Free Radicals in Solution[M], Wiley: New York, 1957.
[18] Ikeda K C, Braun A B, Sorenson E B. Autoxidation of 2-alkenyldioxolanes and 2-alkenyl-1,3-dioxanes [J]. J. Org. Chem.,1964, 29: 286.
[19] Ouchi T, Nakamura S, Hamada M. Cyclic acetal -photosensitized polymerization. I. photopolymerization of styrene in the presence of 1, 3-dioxolanes [J]. J. Polym. Sci. Polym. Chem.,1975, 13: 455-466.
[20] Ouchi T, Hamada M. cyclic acetal-photosensitized polymerization. II. photopolymerization of styrene in the presence of various monocyclic acetals[J]. J. Polym. Sci. Polym. Chem., 1976, 14: 2527-2533.
[21] Ouchi T, Nagaya K, Oiwa M. Cyclic acetal-photosensitized polymerization. III. photopolymerization of styrene in the presence of 2,4,8,10-tetraoxaspiro undecane compounds [J]. J. Polym. Sci.: Polym. Chem. Ed. ,1976, 14: 2836.
[22] Ouchi T, Komatsu Y.Cyclic acetal-photosensitized polymerization. V. photopolymerization of styrene sensitized by the system of 1, 3-dioxolane and α-azo bisisobutyronitrile [J]. J. Macromolecular Sci. Chem., 1977, A11(3): 483-9.
[23] Ouchi T, Sato C, Yamamoto T. Cyclic acetal-photosensitized polymerization. XI. photoirradiations onto polycyclic acetals [J]. J. Macromol. Sci. Chem.,1980, 14(3): 265-275.
[24] Ouchi T, Azuma T. Acetal-photosensitized polymerization. 15 photoirradiations of maleic anhydride in the presence of 2,4,8,10-tetraoxaspiro undecane compounds[J]. Eur. Polym. J., 1982, 18: 809- 812.
[25] Ouchi T, Nakamura T, Oiwa M. Cyclic acetal-photosensitized polymerization. VI. photopolymerization of 2 -vinyl-1,3-dioxolane [J]. J. Macromol. Sci. Chem.,1977, 9: 1651-1662.
[26] Ouchi T, Nakamura T, Komatsu Y. Cyclic acetal-photosensitized polymerization. VII. photopolymerization of 2-vinyl-4- hydroxymethyl- 1,3-dioxolane [J]. J. Polym. Sci. Polym. Chem.,1979, 17: 147-154.
[27] Ouchi T, Nanki S, Komatsu Y.Cyclic acetal-photosensitized polymerization. XII. photopolymerizations of styrene methyl methacrylate in the presence of polycyclic acetals [J]. J. Macromolecular Sc. Chem.,1980, A14(3): 277-85.
[28] Mosca R, Fagnoni M, Mella M, Albini A. Synthesis of monoprotected 1,4-diketones by photoinduced alkylation of enones with 2-substituted-1,3-dioxolanes [J]. Tetrahedron, 2001, 57: 10319-10328.
[29] Malatesta V, Ingold K U. Stereoelectronic effects in hydrogen atom abstraction from ethers [J]. J. Am. Chem. Soc., 1981, 103: 609-614.
[30] Shi S Q, Gao H, Wu G Q, et al. Cyclic acetal as coinitiator for bimolecular photoinitiating systems [J]. Polymer, 2007, 48(10): 2860-2865.
[31] Shi S Q, Gao H, Xiao P, et al. Influence of chemical structure of benzophenones and cyclic acetals on the kinetics of diacrylates [J]. Polymer Preprints, 2006, 47(2): 333.
[32] Shi S Q, Gao H, Nie J. 1,3-Benzodioxole as initiator for photopolymerization of 1,6-hexanedioldiacrylate[J]. Chinese Chemical Letters, 2007, 18(6):750-753.
[33] 史素青, 张琴, 高娜, 等. 单体性质对樟脑醌/胡椒环光引发活性的影响[J]. 高分子学报,2012,43(8):812-817. Shi S Q, Zhang Q, Gao N, et al. Effect of monomer characteristics on photoinitiating activity of camphorquinone/1,3-benzodioxole system[J]. Acta Polymerica Sinica, 2012, 43(8):812-817.
[34] Shi S Q, Nie J. Investigation of 3,4-methylenedioxybenzene methoxyl methacrylate as coinitiator and comonomer for dental application[J]. Journal of Biomedical Materials Research Part B:Applied Biomaterials, 2007,82B:487-493.
[35] Tagashira M, Ohtake Y. A new antioxidative 1,3-benzodioxole from melissa officinalis[J]. Planta Med., 1998, 64:555-558.
[36] Lu Q, Xu J, Chen S, Yang F. Antioxidant activity of extracts of black sesame seed (sesamum indicum L.) by supercritical carbon dioxide extraction[J]. J. Agric. Food Chem., 2004, 52: 943-947.
[37] Jurd L, Narayana V L, Pauli K D. In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models[J]. J. Med. Chem., 1987, 30: 1752-1756.
[38] Joshi R, Kumar M S, Satyamoorthy K, et al. Free radical reactions and antioxidant activities of sesamol: pulse radiolytic and biochemical studies[J]. J Agri. Food Chem., 2005, 53: 2696-2703.
[39] Hodgson E, Philpot R M. Interaction of methylenedioxyphenyl (1,3-benzodioxle) compounds with enzymes and their effect on mammals[J]. Drug. Metab. Rev., 1974, 3:231-301.
[40] Wang K M,Han J, Shi S Q, et al. Effect of cyclic acetals structure on efficiency of photoinitiation[J]. Polymers for Advanced Technologies, 2010, 21(6): 430-434.
[41] Yang J L, Xu F, Shi S Q, et al. Influence of structure of benzodioxole derivatives on photoinitiation efficiency of benzophenone[J]. Photochemical and Photobiological Sciences, 2012, 11(8): 1377-1382.
[42] Wang K M, Yang D Z, Xiao M, et al. Sesamin as a co-initiator for unfilled dental restorations[J]. Acta Biomaterialia, 2009, 5(7): 2508-2517.
[43] Wang K M, Ma G P, Xiao M, et al. Cyclic acetals as coinitiators in CQ-induced photopolymerizations[J]. Polymer Journal, 2010, 42(6):450-455.
[44] Janina Kabatc. Cyclic acetals as the second co-initiators in three-component photoinitiating systems[J]. Polym. Bull., 2012, 6(68):667 679.
[45] Xiao P, Laleve'e J, Allonas X, et al. Photoinitiation mechanism of free radical photopolymerization in the presence of cyclic acetals and related compounds[J]. Journal of Polymer Science, Part A: Polymer Chemistry, 2010, 48(24): 5758-5766.
[46] Wang K M, Nie J. 6-Benzoyl-1,3-benzodioxolane as a photoinitiator for free radical polymerization[J]. Journal of Photochemistry and Photobiology A: Chemistry, 2009, 204(1): 7-12.
[47] Yang J L, Xu F, Shi S Q, et al. Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator[J]. Photochem. Photobiol. Sci., 2012. DOI:10.1039/c2pp25241d.
[48] Wang K M, Ma G P, Yin R X, et al. Benzophenone-1,3-dioxane as a free radial initiator for photopolymerization[J]. Materials Chemistry and Physics, 2010, 124(1): 453-457.