Amine Responsive Poly(lactic acid) (PLA) and Succinic Anhydride (SAh) Graft-Polymer: Synthesis and Characterization

Abstract

Amines are known to react with succinic anhydride (SAh), which in reactions near room temperature, undergoes a ring opening amidation reaction to form succinamic acid (succinic acid-amine). In this work, we propose to form an amine-responsive polymer by grafting SAh to a poly(lactic acid) (PLA) backbone, such that the PLA can provide chemical and mechanical stability for the functional SAh during the amidation reaction. Grafting is performed in a toluene solution at mass content from 10 wt% to 75 wt% maleic anhydride (MAh) (with respect to PLA and initiator), and films are then cast. The molecular weight and thermal properties of the various grafted polymers are measured by gel permeation chromatography and differential scanning calorimetry, and the chemical modification of these materials is examined using infrared spectroscopy. The efficiency of the grafting reaction is estimated with thermogravimetric analysis. The degree of grafting is determined to range from 5% to 42%; this high degree of grafting is desirable to engineer an amine-responsive material. The response of the graft-polymers to amines is characterized using X-ray photoelectron spectroscopy, infrared spectroscopy, and differential scanning calorimetry. Changes in the chemical and thermal properties of the graft-polymers are observed after exposure to the vapors from a 400 ppm methylamine solution. In contrast to these changes, control samples of neat PLA do not undergo comparable changes in properties upon exposure to methylamine vapor. In addition, the PLA-g-SAh do not undergo changes in structure when exposed to vapors from deionized water without amines. This work presents potential opportunities for the development of real-time amine sensors.