Novel Heat-Resistant Isocyanate- Based Polymers

Abstract

This paper describes the preparation and properties of novel heat- resistant, isocyanate-based polymers. Poly(urethane-oxazolidones) (1/1 molar ratio) were prepared by reaction of NCO-terminated urethane prepolymers with polyepoxides. Poly(urethane-oxazolidone-isocyanurates) (3/3/1 molar ratio) were made by reaction of NCO-terminated urethane prepolymers with triglyci dyl isocyanurate. Poly(urethane-oxazolidone-isocyanurates) (3/3/2 molar ratio) were prepared by trimerization of equimolar mixtures of NCO-terminated urethane prepolymers and an NCO-terminated oxazolidone adduct. The poly(urethane-oxazolidone-isocyanurate) films exhibited very good stress-strain properties at room temperature (22°C), as well as at elevated temperature (150°C). The good thermal stability was also confirmed by TGA. These materials appear to be good candidates for heat-resistant elastomers, coatings, and adhesives. Poly(urethane-isocyanurates) (3/1 molar ratio) were also pre pared, and were compared with oxazolidone containing poly(urethane-iso cyanurates).

Get full access to this article

View all access options for this article.

References

Kresta, J.E. and K.H. Hsieh. 1978. Macromol. Chem., 179:2997.

Reymore, H.E. Jr. , P.S. Carleton , R.A. Kolakowski and A.A.R. Sayigh. 1975. J. Cell. Plastics, 11:328.

Farrissey, W.J. , J.S. Rose and P.S. Carleton. 1970. J. Appl. Polymer Sci., 14:1093.

Kordomenos, P.I. , K.C. Frisch and J.E. Kresta. 1983. J. Coat. Technol. , 55(700):59.

Kordomenos, P.I. , J.E. Kresta and K.C. Frisch. 1987. Macromolecules, 20(9):2077.

Ashida, K and T. Yagi. 1969. British patent 1,155,768 (to Nisshin Spinning Co.).

Sayigh, A.A.R. 1974. Advances in Urethane Science and Technology, Vol. 3, K. C. Frisch and S. L. Reegen , eds., Lancaster, PA: Technomic Publishing Co., Inc., p. 141.

Ashida, K. and K.C. Frisch. 1972. J Cell. Plastics, 8:160.

Ashida, K. and K.C. Frisch. 1972. J. Cell. Plastics, 8:194.

10.

Nawata, T. , J.E. Kresta and K.C. Frisch. 1975. J. Cell. Plastics, 11:267.

11.

Kresta, J.E. and K.C. Frisch. 1975. J. Cell. Plastics , 11:68.

12.

12. Hayash, E. F., H. E. Reymore and A. A. R. Sayigh. 1972. U. S. Patent 3,673,128 (to the Upjohn Co.).

13.

Frisch, K.C. and S.W. Wong. 1990 . Cellular Polymers, 9:433.

14.

Sandler, S.R. 1967. J. Appl. Polymer Sci., 11:811.

15.

Ahmetovic, M. , I. Javni and M. Vranes. 1986. Polimeri (Zagreb) , 7(6):175.

16.

Carleton, P.S. and G.C. Proctor. 1988. 31st SPI Proceedings, Urethane Division, Philadelphia, PA, October 18-21, 1988, p. 68.

17.

Carleton, P.S. , D.P. Waszeciak and L.M. Alberino. 1985. 29th SPI Proceedings, Urethane Division, Reno, NV, October, 1985, p. 154.

18.

Nelson, D. 1987. SPI-FSK Proceedings, Aachen , W Germany, September 29-October 2, 1987, p. 384.

19.

Speranza, P. and W.J. Peppel. 1958. J. Org. Chem. , 23:1922.

20.

Pankratov, V.A. , Ts. M. Frenkel and A.M. Fainleib. 1983. Russian Chemical Reviews, 52(6):576.

21.

Sendijarevic, A. , V. Sendijarevic and K.C. Frisch. 1986. Polimeri (Zagreb), 7(6):159.

22.

Sendijarevic, A. , V. Sendijarevic and K.C. Frisch. 1987. J. Polym. Sci., Polym. Chem Ed., 25:151.

23.

Kitayama, M. , Y. Iseda , F. Odako , S. Anzai and K. Irako. 1980. Rubber Chem. Technol. , 53:1.

24.

Kinjo, N. , S. Numata , T. Koyama and T. Narahara. 1983. J. Appl. Polymer Sci., 28:1729.

25.

Sehovic, H. , A. Sendijarevic , V. Sendijarevic and K.C. Frisch. 1987. J. Coat. Technol., 59(747):29.

26.

Dijkstra, R. and E.A.M.F. Dahmen. 1964. Annal. Chim Acta, 31:38.

27.

Zilic, M. , A. Sendijarevic , V. Sendijarevic and K.C. Frisch. 1989. J. Polym. Sci., Polym. Chem. Ed., 27:1843.

28.

Sehovic, H. , A. Sendijarevic , V. Sendijarevic and K.C. Frisch. 1987. J. Polym. Sci., Polym. Chem. Ed., 25:2729.

29.

Vlajic, M. , E. Torlic , A. Sendijarevic and V. Sendijarevic . 1989. Polimeri (Zagreb), 10(3):62.