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Functional polymers. II. Preparation and polymerization of methyl 5-vinylsalicylate, methyl 5-vinylacetylsalicylate, 5-vinylsalicylic acid, and 5-vinylacetylsalicylic acid

Bailey, D. and Tirrell, D. and Vogl, O. (1976) Functional polymers. II. Preparation and polymerization of methyl 5-vinylsalicylate, methyl 5-vinylacetylsalicylate, 5-vinylsalicylic acid, and 5-vinylacetylsalicylic acid. Journal of Polymer Science: Polymer Chemistry Edition, 14 (11). pp. 2725-2747. ISSN 0360-6376. https://resolver.caltech.edu/CaltechAUTHORS:BAIjpspce1976

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Abstract

Four new derivatives of 5-vinylsalicylic acid were prepared and their homopolymerization and copolymerization with acrylic acid and methacrylic acid investigated. Methyl 5-vinylsalicylate was prepared in a six-step synthesis from methyl salicylate in an overall yield of 35%. Acetylation in the last step yielded methyl 5-vinylacetylsalicylate. Hydrolysis of methyl 5-vinylsalicylate gave 5-vinylsalicylic acid which was acetylated to 5-vinylacetylsalicylic acid (5-vinyl aspirin). The 5-vinyl-substituted salicylic acid derivatives could be readily homopolymerized and copolymerized with acrylic acid and methacrylic acid to give various compositions of copolymers. It is worth noting that even the monomers with free phenol groups could be readily polymerized with azobisisobutyronitrile as radical initiator to high molecular weight polymers without interference of the phenolic OH group.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/pol.1976.170141113DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/pol.1976.170141113/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, D.0000-0003-3175-4596
Additional Information: © 1976 John Wiley & Sons. Received January 23 ,1976. This work was supported by a grant of the ARO, Life Science Division, and in part by the National Science Foundation. The authors are particularly indebted to Dr. Eugene Sporn for his inspiration and encouragement during the early part of this work. This paper is dedicated to Professor George Manecke on the occasion of his 60th birthday, with best personal wishes. Part of this work was presented at the 6th NERM Burlington, 1974, No. 165, and at the IUPAC Symposium on Modified Polymers, Their Preparation and Properties, Bratislava, 1975. For Part 1 of this series, see Bailey et al.
Funders:
Funding AgencyGrant Number
Army Research Office (ARO)UNSPECIFIED
NSFUNSPECIFIED
Issue or Number:11
Record Number:CaltechAUTHORS:BAIjpspce1976
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:BAIjpspce1976
Official Citation:Bailey, D., Tirrell, D. and Vogl, O. (1976), Functional polymers. II. Preparation and polymerization of methyl 5-vinylsalicylate, methyl 5-vinylacetylsalicylate, 5-vinylsalicylic acid, and 5-vinylacetylsalicylic acid. J. Polym. Sci. Polym. Chem. Ed., 14: 2725–2747. doi: 10.1002/pol.1976.170141113
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55064
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:20 Feb 2015 21:29
Last Modified:03 Oct 2019 08:02

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