This work was supported in part by grants G-11339 and G-21405 of the National Science Foundation.
Some reactions of p-vinylacetophenone–styrene copolymers†
Article first published online: 10 MAR 2003
Copyright © 1964 John Wiley & Sons, Inc.
Journal of Polymer Science Part A: General Papers
Volume 2, Issue 2, pages 823–834, February 1964
How to Cite
Beckerbauer, R. and Baumgarten, H. E. (1964), Some reactions of p-vinylacetophenone–styrene copolymers. J. Polym. Sci. A Gen. Pap., 2: 823–834. doi: 10.1002/pol.1964.100020219
- Issue published online: 10 MAR 2003
- Article first published online: 10 MAR 2003
- Manuscript Received: 12 DEC 1962
A new synthesis of p-vinylacetophenone was developed. Copolymers of p-vinylacetophenone and styrene were prepared by copolymerization and by partial Friedel-Crafts acetylation of polystyrene. The copolymers were converted into the oximes, but subsequent reduction was unsuccessful. Beckman rearrangement of the oximes led to insoluble resins. The acetyl copolymers were partially brominated to give an α-bromo-p-vinylacetophenone/p-vinylacetophenone/styrene terpolymers. Nucleophilic displacement of the bromine of these terpolymers with secondary amines yielded α-piperidino- and α-morpholino-p-vinylacetophenone terpolymers. The Delepine reaction of the brominated copolymer produced an α-amino-p-vinylacetophenone terpolymer. The piperidino and amino ketone terpolymers were reduced to the corresponding alcohol derivatives with lithium-aluminum hydride. The amino ketone and amino alcohol terpolymers had moderate solubility characteristics in acidic alcohols and water. The α-amino ketone terpolymer was very sensitive to base and afforded a facile crosslinking of the acetyl copolymer.