Nucleophilic catalysis of halide displacement from brominated poly(isobutylene-co-isoprene)

European Polymer Journal

Volumn 46, Issue 4, 2010, Pages 702-708

  Parent, J Scott ^a   Malmberg, Sean ^a   McLean, J Keith ^a   Whitney, Ralph A ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Butyl rubber; Esterification; Nucleophilic catalysis; Polymer modification

Indexed keywords

BUTYL RUBBER; ELECTROPHILES; NUCLEOPHILIC CATALYSIS; POLYMER MODIFICATIONS; REACTION MECHANISM;

BUTENES; CARBOXYLATION; CATALYSIS; ESTERS; HYDROCARBONS; ISOMERS; POLYMERS; REACTION INTERMEDIATES; RUBBER;

ESTERIFICATION;

EID: 77749233725     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2009.12.029     Document Type: Article

References (19)

1. Dubey V., Pandey S.K., and Rao N.B.S.N. Review research trends in the degradation of butyl rubber. J Anal Appl Pyrol 34 (1995) 111-125
2. Boyd R.H., and Pant P.V.K. Molecular packing and diffusion in polyisobutylene. Macromolecules 24 (1991) 6325-6331
3. Puskas J.E. New elastomers: biomacromolecular engineering via carbocationic polymerization. In: Bhowmick A.K. (Ed). Current topics in elastomers research (2008), CRC press 193-219
4. Parent J.S., White G.D.F., Thom D.J., Whitney R.A., and Hopkins W. Sulfuration and reversion reactions of brominated poly(isobutylene-co-isoprene). J Polym Sci A: Polym Chem 41 (2003) 1915-1926
5. 2 initiated crosslinking. J Appl Polym Sci 78 (2000) 2302-2310
6. Parent J.S., White G.D.F., Thom D.J., Whitney R.A., and Hopkins W. Amine substitution reactions of brominated poly(isobutylene-co-isoprene). Macromolecules 35 (2002) 3374-3379
7. Tsou A.H., Duvdevani I., and Pawan K. Quaternary ammonium elastomeric ionomers by melt-state conversion. Polymer 45 (2004) 3163-3173
8. Parent J.S., Penciu A., Guillen-Castellanos S.A., Liskova A., and Whitney R.A. Synthesis and characterization of isobutylene-based ammonium and phosphonium bromide ionomers. Macromolecules 37 (2004) 7477-7483
9. Yamashita S., Kodama K., Ikeda Y., and Kohjiya S. Chemical modification of butyl rubber. I. Synthesis and properties of poly(ethylene oxide)-grafted butyl rubber. J Polym Sci A: Polym Chem 31 (1993) 2437-2444
10. Guillen-Castellanos S.A., Parent J.S., and Whitney R.A. Synthesis of ester derivatives of brominated poly(isobutylene-co-isoprene): solvent-free phase transfer catalysis. Macromolecules 39 (2006) 2514-2520
11. Chu C.Y., and Vukov R. Determination of the structure of butyl rubber by NMR spectroscopy. Macromolecules 18 (1985) 1423-1430
12. Ho K.W., and Guthmann J.E. The ozonolysis of butyl and halobutyl elastomers. J Polym Sci A: Polym Chem 27 (1989) 2435-2455
13. Tipnis S. M.Sc. Thesis, Queen's University; 2003.
14. Frechet J.M.J. Chemical modification of halogenated polymers under phase transfer catalysis. In: Mathias L.J., and Carraher C.E. (Eds). Crown ethers and phase transfer catalysis in polymer science (1984), Plenum press
15. Dehmlow E.V., and Dehmlow S.S. Monographs in modern chemistry No. 11: phase transfer catalysis. 2nd ed. (1983), Verlag Chimie, Germany
16. Fréchet J.M.J., de Smet M.D., and Farrall M.J. Application of phase-transfer catalysis to the chemical modification of cross-linked polystyrene resins. J Org Chem 44 (1979) 1774-1779
17. Fréchet J.M.J. Chemical modification of polymers under phase transfer conditions. Macromol Sci-Chem A15 (1981) 877-890
18. McLean J.K., Guillen-Castellanos S.A., Parent J.S., Whitney R.A., and Resendes R. Synthesis of graft copolymer derivatives of brominated poly(isobutylene-co-isoprene). Euro Polym J 43 (2007) 4619-4627
19. Hayami J.I., Hihara N., and Kaji A. An estimation of the nucleophilicities and the nucleofugicities of anionic nucleophiles studied in the reversible Finkelstein reactions of benzyl derivatives in acetonitrile. Chem Lett (1979) 413-414