Tirrell, David and Vogl, Otto (1980) Functional Polymers V. Preparation and Polymerization of Methyl 4-Vinylsalicylate, 4-Vinylsalicylic Acid and 4-Vinylacetylsalicylic Acid. Makromolekulare Chemie, 181 (10). pp. 2097-2109. ISSN 0025-116X. doi:10.1002/macp.1980.021811008. https://resolver.caltech.edu/CaltechAUTHORS:20150220-124913035
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Abstract
Methyl 4-vinylsalicylate, 4-vinylsalicylic acid, and 4-vinylacetylsalicylic acid were prepared in overall yields of 28%, 21 % and 16%, respectively, starting with 3-ethylphenol. Radical polymerization of all three monomers was investigated. Methyl 4-vinylsalicylate and 4-vinylsalicylic acid polymerized normally via radical initiation, giving soluble polymers of high molecular weight. 4-Vinylacetylsalicylic acid gave gelled polymerization mixtures in tert-butanol and in dimethyl sulfoxide, using the same experimental procedure; this was shown to be a result of intermolecular transesterification during polymerization. A water-insoluble copper complex of poly(4-vinylsalicylic acid) was prepared. Methyl 4-vinylacetylsalicylate was also synthesized, in 35% yield, but no polymerization experiments were performed with this monomer. These new polymeric salicylic acid derivatives are of interest as ultraviolet stabilizers, as protective agents for the skin, as metal-complexing agents, and as potential medicinal agents.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1980 Alber. Now owned by Wiley. Manuscript received: July 24, 1979. Article first published online: 12 MAR 2003. This paper was written after D.T. had become Assistant Professor of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania. | |||||||||
| Issue or Number: | 10 | |||||||||
| DOI: | 10.1002/macp.1980.021811008 | |||||||||
| Record Number: | CaltechAUTHORS:20150220-124913035 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20150220-124913035 | |||||||||
| Official Citation: | Tirrell, D. and Vogl, O. (1980), Functional polymers, 5. Preparation and polymerization of methyl 4-vinylsalicylate, 4-vinylsalicylic acid and 4-vinylacetylsalicylic acid. Makromol. Chem., 181: 2097–2109. doi: 10.1002/macp.1980.021811008 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 55054 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Anne Hormann | |||||||||
| Deposited On: | 24 Feb 2015 00:40 | |||||||||
| Last Modified: | 10 Nov 2021 20:41 |
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