COMPARISON OF THREE DIFFERENT DEGRADATION METHODS TO PRODUCE LIQUID EPOXIDIZED NATURAL RUBBER

Abstract

ABSTRACT Epoxidized natural rubber (ENR) has a high molecular weight, which has limited its solubility and processibility. For many potential applications, such as adhesives and coatings, ENR needs to be degraded into shorter chain lengths to form liquid ENR (LENR). We compared three different methods of preparing LENR: mechanical milling, chemical degradation initiated by potassium peroxodisulfate, and photooxidation initiated by ultraviolet (UV) irradiation. All the methods break down the ENR via free radicals but at different rates and by different mechanisms. In the LENR produced by these methods, ketone, aldehyde, carboxylic acid, and ester and lactone groups were observed; however, a hydrofuranic structure was only formed with UV degradation. The oxirane group was not affected significantly during the degradation, indicating that the chain sessions occurred predominantly via the –C=C– bonds. Spectroscopic analyses revealed that the consumption of a double bond is related to the extent of degradation initiated by potassium peroxodisulfate and UV irradiation. Mastication with a two roll mill produced LENR with a greater degree of unsaturation and fewer polar groups; therefore, presumably, significant chain scissions occurred from the rupturing of –C–C– single bonds. Comparing the reaction time, more LENR was obtained by UV degradation. As expected, an increase in the oxygen concentration led to the generation of more radicals, which could result in some coupling reactions.