Abstract
The aim of present study is to examine the photo-initiation efficiency of N,N-dimethylacrylamide-based allylic ammonium salt as one component addition-fragmentation agent (cationic photoinitiator cum radical source) in free radical accelerated cationic polymerization. Novel addition-fragmentation agent (AFA), 2-(N,N-dimethylcarboxy-3-propenyl)(phenylcarbonyl-4-phenylene) dimethyl ammonium hexafluoroantimonate (DMPDA) was synthesized as cationic photoinitiator and its initiation efficiency was examined in polymerization of cyclohexene oxide (CHO), isobutyl vinyl ether (IBVE), and n-butyl vinyl ether (n-BVE) in CH2Cl2 solvent at wavelength λ > 290 nm. The rate of polymerization increases with the increase in initiator concentration and reaction time. The results demonstrate that DMPDA acts as an efficient photoinitiator (AFA) without use of radical source in free radical accelerated cationic polymerization.
Similar content being viewed by others
References
Lee H, Neville K (1967) Handbook of epoxy resins. McGraw-Hill, New York
Mark HF, Gaylord NG, Bikajes NM (eds) (1968) Encyclopedia of polymer science and technology, vol 8. Interscience, New York, 303 pp
Crivello JV (1984) Cationic polymerization—iodonium and sulfonium salt photoinitiators. Adv Polym Sci 62:1–42
Crivello JV (1999) The discovery and development of onium salt cationic photoinitiators. J Polym Sci Polym Chem Ed 37:4241–4254
Gupta MK, Singh RP (2008) Cationic polymerization of epoxides using novel xanthenyl phosphonium salts as thermo-latent initiator. Polym Bull 60:755–763
Gupta MK, Singh RP (2009) Thermally induced cationic polymerization of glycidyl phenyl ether using novel xanthenyl phosphonium salts. Macromol Res 17:221–226
Gupta MK, Singh RP (2009) Novel dibenzocycloheptenyl phosphonium salts as thermolatent initiator in cationic polymerization. J Appl Polym Sci 112:3707–3713
Crivello JV (1978) In: Pappas SP (ed) UV curing: science and technology. Technology Marketing Corp., Norwalk, pp 22–77
Yagci Y, Reetz I (1998) Externally stimulated initiator systems for cationic polymerization. Prog Polym Sci 23:1485–1538
Yagci Y (2004) Wavelength flexibility in photoinitiated cationic polymerization. Macromol Symp 215:267–280
Yagci Y, Schnabel W (1994) Direct and sensitized photoinitiated cationic polymerization using pyridinium salts. Macromol Chem Macromol Symp 85:115–127
Gupta MK, Singh RP (2006) Diphenyldiselenide as novel non-salt photoinitiator for photosensitized cationic polymerization of N-vinyl carbazole. Macromol Symp 240:186–193
Yagci Y, Onen A, Reetz I (2001) Structure and reactivity of addition fragmentation agents in photochemically and thermally induced cationic polymerization. Macromol Symp 174:255–267
Onen A, Yagci Y (2001) Initiation of cationic polymerization by using allyl anilinium salts in the presence of free radical initiators. Macromolecules 34:7608–7612
Gupta MK, Singh RP (2009) Novel allylic phosphonium salts in free radical accelerated cationic polymerization. Polym Bull 62:271–280
Onen A, Yagci Y (2001) Synthesis of novel addition fragmentation agent based on michler’s ketone and its use as photo-initiator in cationic polymerization. Polymer 42:6681–6685
Yagci Y, Yildirim S, Onen A (2001) A novel bifunctional addition-fragmentation agent for photoinitiated cationic polymerization. Macromol Chem Phys 202:527–531
Yurteri S, Onen A, Yagci Y (2002) Benzophenone based addition fragmentation agent for photoinitiated cationic polymerization. Eur Polym J 38:1845–1850
Armareqo WLF, Perrin DD (1993) Purification of organic chemicals, 4th edn. Butter Worth-Heinemann, Oxford
Davoust M, Briere J-F, Metzner P (2006) A diastereoselective and concise synthesis of functionalized vinyl epoxides with a Morita-Baylis-Hillman backbone. Org Biomol Chem 4:3048–3051
Crivello JV, Dietliker K (1998) Free radical polymerization. In: Bradley (ed) Photoinitiators for free radical, cationic & anionic polymerization, vol III, 2nd edn. Wiley, New York, pp 63–331
Yagci Y, Schnabel W (1993) Flash-photolysis experiments with pyridinium salts regarding the initiation of cationic polymerizations. Macromol Rep A 30:175–182
Acknowledgments
Authors are grateful to Dr. S. Sivaram, Director, NCL, Pune for providing necessary facilities and fruitful discussions. MKG thankful to Council of Scientific and Industrial Research, New Delhi, for the award of research fellowship.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Gupta, M.K., Mehare, R. & Singh, R.P. Novel addition-fragmentation agent in cationic photopolymerization. Polym. Bull. 65, 25–34 (2010). https://doi.org/10.1007/s00289-009-0182-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-009-0182-4