Polymer Engineering Faculty Research

Title

New Intramolecular Effect Observed for Polyesters: An Anomeric Effect

Document Type

Article

Publication Date

Fall 2004

Abstract

A series of polyesters was prepared to evaluate hydrolytic stability as a function of cyclohexyl dibasic acid content. The three cyclohexyl dibasic acids: 1,2; 1,3; and 1,4 were formulated into polyesters with two glycols. The proportion of cis and trans isomers was evaluated via 1H NMR. The hydrolytic stability of short chain polyesters was evaluated in an acetone/water mixture which solubilized the polyesters to mimic oligoester behavior within a thermosetting polyester coating environment. The rate of hydrolysis was monitored by acid titration and corroborated by GPC. Surprisingly, 1,2-cylohexyl diacid-based polyesters were robust, and 1,3-cyclohexyl diacid-based polyesters were the most susceptible to hydrolysis. Evidently, a 1,2-anchimeric effect for cyclohexyl dibasic acid polyesters was not an important consideration, while the 1,3-cyclohexyl ester interaction was. Consequently, an anomeric effect was proposed.

Volume

1

First Page

2

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