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Functional polymers. VI. Preparation and polymerization of methyl 3-vinylsalicylate, methyl 3-vinylacetylsalicylate, 3-vinylsalicylic acid, and 3-vinylacetylsalicylic acid

Iwasaki, M. and Tirrell, D. and Vogl, O. (1980) Functional polymers. VI. Preparation and polymerization of methyl 3-vinylsalicylate, methyl 3-vinylacetylsalicylate, 3-vinylsalicylic acid, and 3-vinylacetylsalicylic acid. Journal of Polymer Science: Polymer Chemistry Edition, 18 (9). pp. 2755-2771. ISSN 0360-6376. doi:10.1002/pol.1980.170180901. https://resolver.caltech.edu/CaltechAUTHORS:IWAjpspc1980

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Abstract

The title compounds were synthesized and their homopolymerizations and copolymerizations with styrene and a number of acrylic monomers were investigated. Methyl 3-vinylacetylsalicylate was prepared in a five-step synthesis from 2-ethylphenol in an overall yield of 40%. Methanolysis of this compound gave methyl 5-vinylsalicylate in 63% yield. Hydrolysis of methyl 3-vinylsalicylate gave a nearly quantitative yield of 3-vinylsalicylic acid which could be acetylated to 3-vinylacetylsalicyclic acid (3-vinyl aspirin). 3-Vinylsalicylic acid derivatives were readily homopolymerized and copolymerized with styrene, methyl methacrylate, and methacrylic acid, and 3-vinylsalicyclic acid was copolymerized with a number of vinyl and acrylic monomers. Copolymer compositions were determined by examination of ^1H-NMR spectra.


Item Type:Article
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http://dx.doi.org/10.1002/pol.1980.170180901DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/pol.1980.170180901/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, D.0000-0003-3175-4596
Additional Information:© 1980 John Wiley & Sons. Received September 17,1979; Accepted January 24,1980. This work was supported in part by a grant from the National Science Foundation to the Materials Research Laboratory at the University of Massachusetts. One of the authors (M.I.) would like to express his appreciation to the Fuji Photo Film Company, Ltd., Minami-Ashigara, Japan, for granting him a leave of absence and support to work at the Polymer Science and Engineering Department of the University of Massachusetts. This article was written after D.T. had become Assistant Professor of Chemistry, Carnegie-Mellon University. The authors would like to thank S. Blanks for his assistance in the preparation of 3-ethylsalicylic acid, R. Jenkins for the GPC measurements, and S. Yoshida for many enlightening discussions. W. Harris assisted in the preparation of the manuscript. This article is dedicated to Professor C. G. Overberger on the occasion of his sixtieth birthday, with warmest personal wishes. Part of this work was presented at the 20th Canadian High Polymer Forum at Quebec, Canada, 1979. For Part V of this series see ref. 1.
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NSFUNSPECIFIED
Fuji Photo Film Company, Ltd.UNSPECIFIED
Issue or Number:9
DOI:10.1002/pol.1980.170180901
Record Number:CaltechAUTHORS:IWAjpspc1980
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:IWAjpspc1980
Official Citation:Iwasaki, M., Tirrell, D. and Vogl, O. (1980), Functional polymers. VI. Preparation and polymerization of methyl 3-vinylsalicylate, methyl 3-vinylacetylsalicylate, 3-vinylsalicylic acid, and 3-vinylacetylsalicylic acid. J. Polym. Sci. Polym. Chem. Ed., 18: 2755–2771. doi: 10.1002/pol.1980.170180901
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55056
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:20 Feb 2015 21:09
Last Modified:10 Nov 2021 20:41

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