Abstract
The present article describes the effect of steric and electronic factors on the efficiency of initiators based on novel xanthenyl phosphonium salts for cationic polymerization of epoxide monomers. 2-substituted (IH, ICl, IMe, and IOMe) xanthenyl phosphonium hexafluoroantimonate were synthesized and characterized by NMR (1H, 13C and 31P) and IR spectroscopy. The order of initiator activity in polymerization of glycidyl phenyl ether (GPE), was found as IH> ICl>IMe>IOMe. To understand the effect of steric factor, the polymerization of cyclohexene oxide (CHO) was performed and the order of activity was found as ICl>IH>IMe >IOMe. All the initiators were found to be latent at ambient temperature and initiates polymerization on thermal initiation. The order of initiator activity was influenced by electronic and steric factors in the system. The thermal stability of these salts was measured by Thermo gravimetric analysis (TGA). The solubility of the initiators in various organic solvents and epoxy monomers is also discussed.
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References
Lee H, Neville K (1967) Handbook of Epoxy Resins. McGraw-Hill, New York
Mark HF, Gaylord NG, Bikajes NM (1968) Encyclopedia of Polymer Science and Technology. Eds. Interscience, New York, vol 8, p 303
Crivello JV (1999) J Polym Sci Part A Polym Chem 37:4241
Yagci Y, Endo T (1997) Adv Polym Sci 127:59
Yagci Y, Reetz I (1998) Prog Polym Sci 23:1485
Gupta MK, Singh RP (2006) Macmol Symp 240:186
Murai S, Nakano Y, Hayase S (2000) J Appl Polym Sci 80:181
Park SJ, Heo GY (2005) Macromol Chem Phys 206:1134
Hamazu F, Akashi S, Koizumi T, Takata T, Endo T (1991) J Polym Sci Polym Chem 29:1675
Shimomura O, Sato T, Tomita I, Endo T (1998) Macromolecules 31:2013
Shimomura O, Tomita I, Endo T (1998) Macromol. Rapid Commun 19:493
Lee SB, Takata T, Endo T (1990) Macromolecules 23:431
Lee SB, Takata T, Endo T (1991) Macromolecules 24:2689
Nakano S, Endo T (1996) J Polym Sci Part A Polym Chem 34:475
Nakano S, Endo T (1995) J Polym Sci Polym Chem 33:505
Kim MS, Lee SB, Lee KB, Endo T (2005) J Appl Polym Sci 95:1439
Takuma K, Takata T, Endo T (1993) Macromolecules 26:862
Kim M, Sanda F, Endo T (2001) J Appl Polym Sci 81:2347
Morikawa H, Sudo A, Nishida H, Endo T (2005) J Appl Polym Sci 96:72
Kosolapoff GM, Maier L (1972) Organic Phosphorus Compounds. Wiley-Interscience, New York
Toneri T, Sanda F, Endo T (1998) J Polym Sci Part A Polym Chem 36:1957
Toneri T, Watanabe K, Sanda F, Endo T (1999) Macromolecules 32:1293
Toneri T, Sanda F, Endo T (2001) Macromolecules 34:1518
Gupta MK, Singh RP (2007) J Appl Polym Sci Communicated
Pellon RF, Carrasco R, Milian V, Rodes L (1995) Synth Commun 25:1077
Pickert M, Frahm AW (1998) Arch Pharma Pharm Med Chem 331:177
Hamanzu F, Akashi S, Koizumi T, Takata T, Endo T (1992) Macromol Chem Rapid Commun 13:203
Ottar B (1947) Acta Chem Scand 1:283
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Gupta, M.K., Singh, R.P. Cationic Polymerization of Epoxides using Novel Xanthenyl Phosphonium Salts as Thermo-latent Initiator . Polym. Bull. 60, 755–763 (2008). https://doi.org/10.1007/s00289-008-0910-1
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DOI: https://doi.org/10.1007/s00289-008-0910-1