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Functional Polymers V. Preparation and Polymerization of Methyl 4-Vinylsalicylate, 4-Vinylsalicylic Acid and 4-Vinylacetylsalicylic Acid

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/macp.1980.021811008DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/macp.1980.021811008/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, David0000-0003-3175-4596
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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