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Poly[(3-hydroxypropyl) oxirane] and poly[(4-hydroxybutyl)oxirane]: New hydrophilic polyether elastomers

Shih, Jenn S. and Tirrell, David A. (1984) Poly[(3-hydroxypropyl) oxirane] and poly[(4-hydroxybutyl)oxirane]: New hydrophilic polyether elastomers. Journal of Polymer Science: Polymer Chemistry Edition, 22 (3). pp. 781-791. ISSN 0360-6376. doi:10.1002/pol.1984.170220325.

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Preparations of poly[(3-hydroxypropyl)oxirane] and poly[(4-hydroxybutyl)oxirane] are described. Three routes to poly[(3-hydroxypropyl)oxirane] are discussed, each of which involves the methanolysis of a polymeric ester. (3-Acetoxypropyl)oxirane, [3-(m-chlorobenzoyloxy)propyl]oxirane, and (3-chloropropyl)oxirane were polymerized using the AIEt_3/H_2O/AcAc initiator system. Poly[(3-acetoxypropyl)oxirane] and poly{[3-(m-chlorobenzoyloxy)propyl]oxirane} were converted directly to poly[(3-hydroxypropyl)oxirane] by methanolysis, the former under either acidic or basic conditions only. Poly[(3-chloropropyl)oxirane] was first converted to poly[(3-benzoyloxypropyl)oxirane] by treatment with tetrabutylammonium benzoate; subsequent basic methanolysis then afforded poly[(3-hydroxypropyl)oxirane]. Poly[(3-hydroxypropyl)oxirane] is a colorless elastomer which can be cast into tough, clear films from water or methanol. Poly[(4-hydroxybutyl)oxirane] was prepared from poly[(4-chlorobutyl)oxirane] by benzoyloxylation and subsequent methanolysis. Poly[(4-hydroxybutyl)oxirane] is insoluble in water, but is hydrophilic and can be cast into tough films from methanol or dimethylsulfoxide.

Item Type:Article
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Tirrell, David A.0000-0003-3175-4596
Additional Information:© 1984 John Wiley & Sons, Inc. Received June 20, 1983; Accepted July 26, 1983. This work was supported by an Alfred P. Sloan Research Fellowship to D. A. Tirrell, and by a grant from the Polymers Program of the National Science Foundation (DMR 82-01180). High-field NMR spectra were recorded on a Bruker WM-300 spectrometer purchased with the aid of a grant from the National Institutes of Health (NIGMS-GM27390-01). The authors thank E. J. Vandenberg for helpful discussions and for a copy of ref. 16.
Funding AgencyGrant Number
Alfred P. Sloan FoundationUNSPECIFIED
NSFDMR 82-01180
Issue or Number:3
Record Number:CaltechAUTHORS:SHIjps1984
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:54610
Deposited By: Anne Hormann
Deposited On:10 Feb 2015 20:33
Last Modified:10 Nov 2021 20:35

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