6-Benzoyl-1,3-benzodioxolane as a photoinitiator for free radical polymerization

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 204, Issue 1, 2009, Pages 7-12

  Wang, Kemin ^a   Nie, Jun ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

Benzophenone; Free radical polymerization; Photochemistry; Type II photoinitiator

Indexed keywords

EID: 63749092525     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2009.02.005     Document Type: Article

References (38)

1. Fouassier J.P. Photoinitiation, Photopolymerization, and Photocuring: Fundamentals and Applications (1995), Hanser, New York pp. 1-16
2. Cokbaglan L., Arsu N., Yagci Y., Jockusch S., and Turro N.J. 2-Mercaptothioxanthone as a novel photoinitiator for free radical polymerization. Macromolecules 36 (2003) 2649-2653
3. Rodrigues M.R., and Neumann M.G. Mechanistic study of tetrahydrofuran polymerization photoinitiated by a sulfonium salt/thioxanthone system. Macromol. Chem. Phys. 202 (2001) 2776-2782
4. Clarka S.C., Hoyle C.E., Jo{combining double acute accent}nssonb S., Morel F., and Decker C. Photopolymerization of acrylates using N-aliphaticmaleimides as photoinitiators. Polymer 40 (1999) 5063-5072
5. Aydin M., Arsu N., and Yagci Y. One-component bimolecular photoinitiating systems, 2-thioxanthone acetic acid derivatives as photoinitiators for free radical polymerization. Macromol. Rapid Commun. 24 (2003) 718
6. Ledwith A., and Purbrich M.D. Initiation of free-radical polymerization by photoinduced electron-transfer processes. Polymer 14 (1973) 521-522
7. Davidson R.S. In: Bethel D., and Gold V. (Eds). Advances in Physical Chemistry (1983), Academic Press, London 1
8. Ledwith A., Bosley J.A., and Purbrich M.D. Exciplex interactions in photoinitiation of polymerisation by fluorenone-amine systems. J. Oil Col. Chem. Assoc. 61 (1978) 95-104
9. Kuhlmann R., and Schnabel W. Laser flash-photolysis investigations on primary processes of sensitized polymerization of vinyl monomers. 1. Experiments with benzophenone. Polymer 17 (1976) 419-422
10. Singer L.A., Brown R.E., and Davis G.A. Photokinetic studies on benzophenone-photocycloaddition to ketenimines and self quenching of benzophenone triplet. J. Am. Chem. Soc. 95 (1973) 8638-8643
11. Dietliker K. Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints vol. 3 (1991), SITA Technology Ltd., London 77 pp
12. Walling C. Free Radicals in Solution (1957), Wiley, New York
13. Elad D., and Youssefyeh R.D. The photochemical conversion of acetals to carboxylic esters. Tetrahedron Lett. 30 (1963) 2189
14. Ouchi T., Nakamura S., and Hamada M. Cyclic acetal-photosensitized polymerization. I. Photopolymerization of styrene in the presence of 1,3-dioxolanes. J. Polym. Sci. Polym. Chem. 13 (1975) 455-466
15. Ouchi T., and Hamada M. Cyclic acetal-photosensitized polymerization. II. Photopolymerization of styrene in the presence of various monocyclic acetals. J. Polym. Sci. Polym. Chem. 14 (1976) 2527-2533
16. Ouchi T., Takakinakamura, and Oiwa M. Cyclic acetal-photosensitized polymerization. VI. Photopolymerization of 2-vinyl-1,3-dioxolane. J. Macromol. Sci. Chem. 9 (1977) 1651-1662
17. Ouchi T., Takakinakamura, and Kuniharu. Cyclic acetal-photosensitized polymerization. VII. Photopolymerization of 2-vinyl-4-hydroxymethyl-1,3-dioxolane. J. Polym. Sci. Polym. Chem. 17 (1979) 147-154
18. Ouchi T., Sato C., and Yamamoto T. Cyclic acetal-photosensitized polymerization. XI. Photoirradiations onto polycyclic acetals. J. Macromol. Sci. Chem. 14 3 (1980) 265-275
19. Ouchi T., and Azuma T. Acetal-photosensitized polymerization. 15. Photoirradiations of Maleic anhydride in the presence of 2,4,8,10-tetraoxaspiro [5,5]undecane compounds. Eur. Polym. J. 18 (1982) 809-812
20. Mosca R., Fagnoni M., Mella M., and Albini A. Synthesis of monoprotected 1,4-diketones by photoinduced alkylation of enones with 2-substituted-1,3-dioxolanes. Tetrahedron 57 (2001) 10319-10328
21. Shi S., Gao H., Wu G., and Nie J. Cyclic acetal as coinitiator for bimolecular photoinitiating systems. Polymer 48 (2007) 2860-2865
22. Shi S., and Nie J. A natural component as coinitiator for unfilled dental resin composites. J. Biomed. Mater. Res. Appl. Biomater. 23 (2007) 44-50
23. Cohen S.G., Parola A., and Parsons G.H. Photo-reduction by amines. Chem. Rev. 73 (1973) 141-161
24. Scaiano J.C. Intermolecular photoreductions of ketones. J. Photochem. 2 (1973) 81
25. Raumer M.V., Suppan P., and Haselbach E. Photoreduction of triplet benzophenone by amines: role of their structure. Chem. Phys. Lett. 252 (1996) 263
26. Daukshas V.K., Gaidyalis P.G., Brukshtus A.B., Ramanauskas Y.Y., Labanauskas L.K., Gasperavichene G.A., Yautakene I.Y., Lapinskas V.V., and Lauzhikene N.A. Synthesis and pharmacological activity of 1,3-benzodioxolane and 1,3-benzodioxolane derivatives. Khimiko-farmatsevticheskii Zhurnal 23 8 (1989) 942-946
27. Tasdelen M.A., Kumbaraci V., Talinli N., and Yagci Y. Photochemically masked benzophenone: photoinitiated free radical polymerization by using benzodioxinone. Polymer 47 (2006) 7611-7614
28. Davidson R.S. In: Foster R. (Ed). Molecular Association vol. 1 (1975), Academic Press, New York 215-334
29. Bi Y., and Neckers D.C. A visible light initiating system for free radical promoted cationic polymerization. Macromolecules 27 (1994) 3683
30. Pouliquen L., Coqueret X., Morlet S.F., and Fouassier J.P. Functionalized polysiloxanes with thioxanthone side groups: a study of their reactivity as radical polymerization macroinitiators. Macromolecules 28 (1995) 8028
31. Paul S. Surface Coating: Science & Technology (1986), Wiley-Intersicence, New York
32. Berner G., Kirchmayr R., and Rist G. Recent developments in photoinitiators. J. Oil Col. Chem. Assoc. 61 (1978) 105
33. Scherzer T., Müller S., Mehnert R., Volland A., and Lucht H. In-line monitoring of the conversion in photopolymerized acrylate coatings on polymer foils using NIR spectroscopy. Polymer 46 (2005) 7072-7081
34. Stansbury J.W., and Dickens S.H. Determination of double bond conversion in dental resins by near infrared spectroscopy. Dent. Mater. 17 (2001) 71-79
35. Decker C., and Moussa K. Real-time kinetic study of laser-induced polymerization. Macromolecules 22 (1989) 4455-4465
36. Andrzejewska E., Linden L.A., and Rabek J.F. The role of oxygen in camphorquinone-initiated photopolymerizationa. Macromol. Chem. Phys. 199 (1998) 441-449
37. Nie J., Andrzejewska E., Rabek J.F., Linden L.A., Fouassier J.P., Paczkowski J., Scigalski F., and Wrzyszczynski A. Effect of peroxides and hydroperoxides on the camphorquinone-initiated photopolymerization. Macromol. Chem. Phys. 200 (1999) 1692-1701
38. Andrzejewska E., Hug G.L., Andrzejewski M., and Marciniak B. Trithianes as coinitiators in benzophenone-induced photopolymerizations. Macromolecules 32 (1999) 2173-2179