Bone and Joint Institute

Title

Carboxylic acid-functionalized butyl rubber: Synthesis, characterization, and physical properties

Document Type

Article

Publication Date

5-6-2015

Journal

Industrial and Engineering Chemistry Research

Volume

54

Issue

17

First Page

4763

Last Page

4772

URL with Digital Object Identifier

10.1021/acs.iecr.5b00421

Abstract

© 2015 American Chemical Society. Polyisobutylene (PIB) and other PIB-based materials are of significant interest for a vast array of applications, but chemical modification is often required to obtain the desired properties. Described here are two new approaches for the preparation of carboxylic acid-functionalized PIB. The ring opening of cyclic anhydrides from an allylic alcohol derivative of butyl rubber and the atom transfer radical polymerization of tert-butyl methacrylate from a rubber derivative both ultimately afford carboxylated materials. These materials displayed significantly enhanced adhesion to stainless steel, as well as increased ultimate tensile strength and Young's modulus in comparison to unmodified rubbers. Rheological studies suggested that they exhibit a greater degree of cross-linking-type behavior than the parent butyl rubber. Combined, these studies suggest that the properties of PIB can be readily tuned through synthetic modifications of the backbone, even at low mole percent, and that carboxylic acid moieties can impart desirable properties for various applications.

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