As the annual global production of plastics has dramatically increased, a considerable amount of non-degradable plastic waste has entered the ocean either by accident or through illegal dumping. For example, synthetic fibers are now known to be continuously released from textiles in washing machines, which is a primary source of marine contamination by fibril pollutants. A recent study revealed that most globally sourced tap water samples contain anthropogenic particles, the majority of which were fibers. Therefore, the incorporation of materials containing readily hydrolyzable linkages introducing degradability has emerged as an attractive strategy to potentially address environmental concerns associated the unintentional release of fibril pollutants into the environment. Previous work on linear polyesters comprising carbohydrate-derived glucarodilactone subunits showed superior degradability compared to isosorbide, its structural analog. Hence, incorporating glucarodilactone into polyester fibers as monomers to impart facile degradability could be an attractive strategy towards addressing the above issues. In this work, degradable thermoset fibers were produced by simultaneous fiber spinning and thiol-ene photopolymerization of monomers. Glucarodilactone was functionalized with 10-undecenoic acid to be used as a difunctional carbohydrate-derived diene monomer. This renewable monomer was blended with multifunctional thiols, diluent, and photoinitiator, which were solidified by UV irradiation under ambient conditions to produce crosslinked films and fibers. Thermoset fibers were completely decomposed in basic aqueous media, and NMR analysis of the degradation products suggested that they were converted into small molecule substituents. To the best of our knowledge, this is the first time to demonstrate the fabrication of thermoset fibers that are fully degradable in basic conditions, and this property is attributed to the incorporation of hydrolyzable glucarodilactone in the crosslinked network. This demonstration of degradable thermoset fibers could provide new insight of how carbohydrate-derived monomers can be incorporated into various plastic product forms, and it provides one strategy for beginning to address the current microplastic pollution problem with high performance thermoset fibers.

Degradable thermoset fibers containing renewable carbohydrate-derived diol subunits

2019 Fall National Meeting

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