In this paper we report the synthesis, the characterization and the practical utilization of two cyclophosphazenes (CPs) substituted with two (C-2-OXA) and six (C-6-OXA) 2-(4-hydroxyphenyl)-2-oxazoline groups, respectively. The first chemical observation on these substrates is that the reactivity of the oxazoline groups is preserved even when these products are attached to the phosphorus atoms of a cyclophosphazene ring. By reaction of C-2-OXA with organic molecules, e.g. adipic acid, and macromolecules, e.g. poly(ethylene terephthalate) (PET), the oxazoline substituents open their heterocycles to form cyclolinear polymers or to act as chain extenders. Similarly, the ring-opening polymerization reaction of C-6-OXA in the presence of cationic initiators allows the production of a new class of cyclomatrix polymers. The characterization of the new materials is reported.
Similar content being viewed by others
References
De Jaeger R., Gleria M., Prog. Polym. Sci. 1998, 23, 179
Gleria M., De Jaeger R. Top. Curr. Chem. 2005, 250, 165
Miyata K., Watanabe Y., Itaya T., Tanigaki T., Inoue K. Macromolecules 1996, 29, 3694
Allcock H. R., McIntosh M. B., Hartle T. J. Inorg. Chem. 1999, 38, 5535
Hartle T. J., McInstosh M. B., Allcock H. R. ACS Polym. Prep. 1999, 40(2), 908
Hartle T. J., Sunderland N. J., McIntosh M. B., Allcock H. R. Macromolecules 2000, 33, 4307
McIntosh M. B., Hartle T. J., Allcock H. R. J. Am. Chem. Soc. 1999, 121, 884
Bertani R., Boscolo-Boscoletto A., Dintcheva N., Ghedini E., Gleria M., La Mantia F., Pace G., Pannocchia P., Sassi A., Scaffaro R., Venzo A. Designed Monomers and Polymers 2003, 6, 245
Gleria M., Bertani R., Pó R., Giannotta G., Fiocca L., Fambri L., La Mantia F.P., Scaffaro R., Resnati G. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 827
Scaffaro R., Botta L., La Mantia F. P., Magagnini P., Acierno D., Gleria M., Bertani R. Polym. Degrad. Stab. 2005, 90, 234
Modesti M., Zanella L., Lorenzetti A., Bertani R., Gleria M. Polym. Degrad. Stab. 2005, 87, 287
Gleria M., Minto F., Bertani R., Tiso B., Pó R., Fiocca L., Lucchelli E., Giannotta G., Cardi N. Phosphorus Res. Bull. 1999, 10, 730
Gleria M., Minto F., Galeazzi A., Pó R., Cardi N., Fiocca L., Spera S. Phosphorus, Sulfur Silicon Relat Elem 1999, 144–146, 201
Pó R., Fiocca L., Giannotta G., Lucchelli E., Cardi N., Minto F., Fambri L., Gleria M. ibidem 2001, 168, 269
Giannotta G., Pò R., Fiocca L., Cardi N., Lucchelli E., Braglia R., Fambri L., Pegoretti A., Minto F., Gleria M. ibidem 2001, 169, 263
Gleria M., Minto F., Tiso B., Bertani R., Tondello E., Po R., Fiocca L., Lucchelli E., Giannotta G., Cardi N. Designed Monomers and Polymers 2001, 4, 219
Gleria M., Pó R., Giannotta G., Fiocca L., Bertani R., Fambri L., La Mantia F. P., Scaffaro R. Macromol. Symp. 2003, 196, 249
Allcock H. R. Phosphorus-Nitrogen Compounds. Cyclic, Linear, and High Polymeric Systems; Academic Press: New York, USA, 1972
Kobayashi S., Mizutani T., Saegusa T. Makromol. Chem. 1984, 185, 441
I. Dez, J. Levalois-Mitjaville, H. Grützmacher, V. Gramlich, R. De Van Jaeger, Eur. J. Inorg. Chem. 10, 1673 (1999)
Van Krevelen D. W. Properties of Polymers; Elsevier: Amsterdam., Netherlands., T., 1990, p 121
Kolarik J., Krulis Z., Slouf M., Fambri L. Polym. Eng. Sci 2005, 45, 817
M. Salame, in Plastic Film Technology, K. M. Finlayson ed. (Technomic: Lancaster, UK, 1989) p. 143
Fry E. M. J. Org. Chem. 1949, 14, 887
Fry E. M. J. Org. Chem. 1950, 15, 802
Nielsen L. E., Landel R. F. Mechanical Properties of Polymers and Composites; M. Dekker: New York, USA, 1994
McCrum N. G., Read B. E., Williams G. Anelastic and Dielectric Effects in Polymeric Solids. Wiley.: New York, USA, 1967
Crawford R. J. Plastics Engineering, Butterworth-Heinemann: Oxford, UK, 1998, p 31
Clarke R. L., Braden M. Biomaterials. 1989, 10, 349
Cardi N., Pò R., Giannotta G., Occhiello E., Garbassi F., Messina G. J. Appl. Polym. Sci. 1993, 50, 1501
L. Fambri, A. Pegoretti, M. Gleria, in Synthesis and Characterizations of Poly(organophosphazenes); M. Gleria and R. De Jaeger, eds. (Nova Science Publishers: Hauppauge, 2004), Chap. 12, p. 257
Chang J. Y., Ji H. J., Han M. J., Rhee S. B., Cheong S., Yoon M. Macromolecules 1994, 27, 1376
Chang J. Y., Park P. J., Han M. J., Chang T. Phosphorus Sulfur Silicon Relat Elem 1999, 144–146, 197
Aoi K., Okada M. Prog. Polym. Sci. 1996, 21, 151
Gant T. G., Meyers A. I. Tetrahedron 1994, 50, 2297
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Prof. C.W.Allen
Rights and permissions
About this article
Cite this article
Bertani, R., Fambri, L., Fiocca, L. et al. Oxazoline-Containing Phosphazene Derivatives Part II Polymer Preparation and Modification Through the Reactivity of Oxazoline Moieties on Cyclophosphazenes. J Inorg Organomet Polym 17, 387–398 (2007). https://doi.org/10.1007/s10904-007-9129-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-007-9129-0