Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Cationic curing of polymer coatings: Evaluation ofo-nitrobenzyl tosylate as a thermally labile acid precursor

  • 77 Accesses

  • 6 Citations

Summary

The propensity ofo-nitrobenzyl tosylate to act as a thermal source ofp-toluenesulfonic acid useful in the cationic curing of polymers was established both in solution and the solid state using a combination of variable temperature1H NMR and quantitative infrared spectroscopy. Monitoring of the thermal generation ofp-toluenesulfonic acid within inert coatings of poly(styrene) or poly(methyl methacrylate) confirmed that the process was most efficient at temperatures between 100 and 110°C, though slow liberation of acid was observed at temperatures as low as 90°C.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    Morrison, H. A. in “The Chemistry of Nitro and Nitroso Groups”, Editor, H. Feuer; The Chemistry of Functional Groups Series, Editor, Patai, S.; Part 1, Chapt. 4, p 165, Interscience, 1969: Pillai, V.N.R.;Synthesis, 1980, 1: Zehavi, U.;Adv. Carbohydr. Chem. Biochem., 1988,46, 179: Pillai, V.N.R. inOrg. Photochem., Editor, Padwa, A.; Vol. 9, Chapt. 3, p. 225: Amit, B.; Zehavi, U.; Patchornik, A.;Isr. J. Chem., 1974,12, 103.

  2. 2.

    Reichmanis, E.; Wilkins, C. W. Jr.; Chandross, E. A.;J. Vac. Sci. Technol., 1981,19, 1338: Wilkins, C.W. Jr.; Reichmanis E.; Chandross, E. A.;J. Electrochem. Soc., 1982,129, 2552.

  3. 3.

    Houlihan, F.M.; Shugard, A.; Gooden, R.; Reichmanis, E.;Macromolecules, 1988,21, 2001.

  4. 4.

    Neenan, T.X.; Houlihan, F.M.; Reichmanis, E.; Kometani, J.M.; Bachman, B.J.; Thompson, L.F.;Macromolecules, 1990,23, 145.

  5. 5.

    Cameron, J.F.; Fréchet, J.M.J.;J. Am. Chem. Soc., 1991,113, in press. Cameron, J.F.; Fréchet, J.M.J.;J. Org. Chem. 1990,55, 5119. Cameron, J.F.; Fréchet, J.M.J.;Proc. Polym. Mat. Sci., 1991,64, xxx.

  6. 6.

    Beecher, J.E.; Cameron, J.F.; Fréchet, J.M.J.;Proc. Polym. Mat. Sci., 1991,64, xxx.

  7. 7.

    Gatechair, L.R.,Proc. Polym. Mat. Sci., 198859, 289; Gatechair, L.R.,Proc. Water Borne and Higher Solids Coat. Symp., 1988,15, 33.

  8. 8.

    Winkle, W.R.; Graziano, K.A.,J. Photopolym. Sci. Technol., 1990,3, 419.

  9. 9.

    Dickinson, W.B.,J. Am. Chem. Soc., 1964,86, 3580.

  10. 10.

    Ledwith A.,Polymer, 1978,19, 1217. Crivello, J. V.;Polymer J., 1985,17, 73.

  11. 11.

    Crivello, J.V.; Lockhart, T.P.; Lee, J.L.;J. Polym.Sci. Sci. Polym. Chem. Ed., 1983,21, 97. Pappas, S.P.; Feng. H.B. in “Cationic polymerization and related Processes” (Goethals, E.J., Editor) Academic Press New York 1984, 325. Endo, T.; Uno, H.;J. Polym. Sci. Polym. Chem. Ed., 1985,23, 359.

  12. 12.

    Sundell, P.E.; Jönsson, S.; Hult, A.;Polym. Mat. Sci. Eng., 1989,61, 82. Sundell, P.E.; Jönsson, S.; Hult, A. in “Radiation Curing of Polymeric Materials” (Hoyle, C.E., Kinstle, J.F. Editors) Chapter 32, ACS Symposium Series 417, 1990, Washington D.C. Sundell, P.E.; Ph.D. Thesis, Department of Polymer Technology, Royal Institute of Technology, (Prof. A. Hult) Stockholm 1990.

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Cameron, J.F., Fréchet, J.M.J. Cationic curing of polymer coatings: Evaluation ofo-nitrobenzyl tosylate as a thermally labile acid precursor. Polymer Bulletin 26, 297–303 (1991). https://doi.org/10.1007/BF00587973

Download citation

Keywords

  • PMMA
  • Tosylate
  • Cationic Polymerization
  • Diglyme
  • Reference Band