Summary
The efficient free radical scavengers 1,1,3,3-tetramethylisoindolinyl 2-oxy and 2,2,6,6-tetramethylpiperidinyl-1-oxy (nitroxides) disappear in styrene at 100°C with near zero order kinetics but at rates which are some 20 times higher than the known rate of initiation of thermal polymerization in the absence of scavenger. A quantitative product analysis has shown that these inhibitors react by hydrogen abstraction from a thermally generated styrene dimer (1-phenyl-1,2,3,9-tetrahydronaphthalene) and to a minor extent by addition to the double bond of styrene monomer.
Similar content being viewed by others
References
ASMUS, K.D., NIGAN, S. and WILLSON, R.L.: Int. J. Radiat. Biol. 29, 211 (1976)
BARR, N.J., BENGOUGH, W.I., BEVERIDGE, G. and PARK, G.B.: Europ. Poly. J. 14, 245 (1978)
BRIERE, R., LEMAIRE, H. and RASSAT, A.: Bull. Soc. Chim. (France) 3273 (1965)
GRIFFITHS, P.G., RIZZARDO, E. and SOLOMON, D.H.: J. Macromol. Sci.-Chem. A17, 45 (1982)
KOPECKY, K.R. and EVANI, S.: Can. J. Chem. 47, 4041 (1969)
MOAD, G., RIZZARDO, E. and SOLOMON, D.H.: J. Macromol. Sci.-Chem. A17, 51 (1982)
PRYOR, W.A.: Organic Free Radicals, ACS Symposium Series 69 (1978)
PRYOR, W.A. and LASSWELL, L.D.: Advances in Free-Radical Chemistry 5, 27 (1975)
PRYOR, W.A., IINO, M. and NEWKOME, G.R.: J. Am. Chem. Soc. 99, 6003 (1977)
RIZZARDO, E. and SOLOMON, D.H.: Polym. Bull. 1, 529 (1979)
RUSSELL, K.E. and TOBOLSKY, A.V.: J. Am. Chem. Soc. 75, 5052 (1953)
SCHMID, P. and INGOLD, K.U.: J. Am. Chem. Soc. 100, 2493 (1978)
ZHULIN, V.M. and STASHINA, G.A.: Bull. Acad. Sci. USSR 26, 2396 (1977)
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Moad, G., Rizzardo, E. & Solomon, D.H. A product study of the nitroxide inhibited thermal polymerization of styrene. Polymer Bulletin 6, 589–593 (1982). https://doi.org/10.1007/BF00255160
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00255160