Synthesis and Characterization of New Functional Polyelectrolytes Based on Carboxyl Containing Methacrylates

Abstract

Three new methacrylic monomers, 6-methacryloyloxyhexanoic acid, 6-(N-methacryloyl)aminohexanoic acid, and ethyl 6-(N-methacryloyl)-aminohexanoate, containing carboxyl groups spaced from the polymerizable double bond by a polymethylene chain, have been synthesized. Multifunctional polymeric materials were obtained by radical polymerization of these monomers with different vinyl monomers. The type and content of the functional groups was modulated on the basis of feed composition and the nature of the functional comonomer selected among 2-hydroxyethyl methacrylate, diethyleneglycol methacrylate, methacrylic acid, vinyl acetate, N-vinyl-2-pyrrolidinone, N-isopropylacrylamide, and 2-(N,N-dimethylamino)ethyl methacrylate. The solubility, molecular weight, and acid-base properties exhibited polyelectrolyte behavior for all copolymers in solution.

Get full access to this article

View all access options for this article.

References

1. Langer, R. Science 1993, 260-260, 920-920.

2. 1997. Principle of Tissue Engineering, W. L. Chich , Ed., Landes Co., Austin, TX, USA.

3. 1998. Biorelated Polymers and Gels, T. Okano , Ed., Academic Press, S. Diego, CA, USA.

4. 1999. Frontiers in Biomedical Polymer Applications, R. M. Ottenbrite, Technomic, Lancaster, PA, USA, Vol. 2.

5. Saltzman, W. H. Nat. Biotechnol., 1999, 17-17, 534-534.

6. Hubbell, J. A. , Curr. Opin. Botechnol., 1999, 10-10, 123-123.

7. Chiellini, E. , Solaro, R. , Leonardi, G. , Giannasi, D. , Lisciani, R. , Mazzanti, G. J. Controlled Release, 1992, 22-22, 273-273.

8. Solaro, R. , D’Antone, S. , Bemporad, L. , Chiellini, E. J. Bioact. Compat. Polym., 1993, 8-8, 236-236.

9. Chiellini, E. , Bemporad, L. , Solaro, R. J. Bioact. Compat. Polym., 1994, 9-9, 152-152.

10.

10. Solaro, R. , Dossi, E. , Chiellini, E. , Mazzanti, G. J. Bioact. Compat. Polym., 1997, 12-12, 27-27.

11.

11. Bizzarri, R. , Solaro, R. , Chiellini, E. J. Bioact. Compat. Polym., 1999, 14-14, 504-504.

12.

12. Miertus, S. , Nair, A. C. , Frecher, V. , Chiellini, E. , Chiellini, F. , Solaro, R. , Tomasi, J. J. Incl. Phenom. Macroc. Chem., 1999, 34-34, 69-69.

13.

13. Chiellini, E. , Bizzarri, R. , Bonaguidi, P. , Talamelli, P. , Solaro, R. J. Macromol. Sci.-Pure Appl. Chem., 1999, A36-A36, 901-901.

14.

14. Hubbell, J. A. Biotechnology, 1995, 13-13, 565-565.

15.

15. Han, D. K. , Park, K. D. , Hubbel, J. A. , Kim, Y. H. J. Biomater. Sci. Polym. Ed., 1998, 9-9, 667-667.

16.

16. Schense, J. C. , Bloch, J. , Aebisher, P. , Hubbel, J. A. Nat. Biotechnol., 2000, 18-18, 415-415.

17.

17. Marvel, C. S. , Elliott, J. R. , Boettner, F. E. , Yuska, H. J. Am. Chem. Soc., 1946, 68-68, 1684-1684.

18.

18. Evans, S. B. , Mulvaney, J. E. , Hall, H. K., Jr. , J. Polym. Sci., Part A, 1990, 28-28, 1073-1073.

19.

19. Kamm, O. , Segur, J. B. Org. Synth. Coll. Vol., 1941, 1-1, 391-391.

20.

20. Marvel, C. S. , MacCorquodale, D. W. , Kendall, F. E. , Lazier, W. A. J. Am. Chem. Soc., 1924, 46-46, 2841-2841.

21.

21. Merchant, R. , Wickert, J. N. , Marvel, C. S. J. Am. Chem. Soc., 1927, 49-49, 1831-1831.

22.

22. 1989. Vogel’s Textbook of practical organic chemistry, B. S. Furniss , A. J. Hannaford , P. W. G. Smith , A. R. Tatchell , Eds., Longman, London, p. 693-693.

23.

23. Hauser, C. R. , Hudson, B. E. , Abramovitch, B. , Shivers, J. C. Org. Synth. Coll. Vol., 1955, 3-3, 142-142.

24.

24. Evans, S. B. , Mulvaney, J. E. , Hall, H. K., Jr. J. Polym. Sci., Part A, 1990, 28-28, 1073-1073.

25.

25. Guistina, R. A. , Hall, H. K., Jr. Polym. Bull., 1991., 25-25, 71-71.

26.

26. Ogliaruso, M. A. , Wolfe, J. F. 1991. In The synthesis of carboxylic acids and esters and their derivatives, S. Patai , Z. Rappoport , Eds., Wiley-Interscience, New York, Vol. 1, p. 5-5.

27.

27. Budd, P. M. 1989. In Comprehensive Polymer Science, C. Booth , C. Price , Eds., Pergamon Press, Oxford, vol. 1, p. 215-215.