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Stimuli-responsive polyglyoxylates as biodegradable polymers

Market for Biodegradable Polymers

Most synthetic polymers are produced from petrochemicals and are not biodegradable. Conventional polymers such as polypropylene and polyethylene persist in the environment for many years, even after their disposal. The potential of biodegradable polymers to overcome such limitations has long been recognized. Under proper conditions, biodegradable plastics can degrade to the point where microorganisms can completely metabolise them to carbon dioxide and water. The global market for biodegradable plastics is expected to reach $3.5 Billion by 2019.

Background

Despite the large global market, the potential for biodegradable polymers has not yet been fully realized due to their high production costs and underperforming properties. Unfortunately, in many cases, the properties of these polymers do not fit the needs of specific applications. More importantly, while they degrade significantly faster than their conventional counterparts, the degradation products of these biodegradable polymers have received much negative attention due to environment concerns such as:

• The accumulation of toxic contaminants and metals, which can inhibit plant growth and harm the environment.

• The great deal of time required to degrade

• The production of tiny plastic fragments that cannot be degraded further.

Traditional biodegradable polymers are also limited by the fact that their degradation cannot be controlled and can therefore not be "turned on or off" as required in their use.

Traditional biodegradable polymers rely on the occurrence of numerous random cleavage events throughout the backbone to break the polymer down into the degradation products (Fig. 1a).

To address this limitation, self-immolative polymers (SIPs) were developed which undergo depolymerisation to monomers upon cleavage of a stimuli-responsive end-cap (Fig. 1b). A single polymer backbone can be engineered to respond to different stimuli simply by changing the end-cap. However, the commercialization of these materials has been hindered by two major limitations: 1) the requirement for expensive, multistep monomer syntheses; 2) depolymerisation to toxic species such as quinone methides or o-phthalaldehyde.

Description of the Invention

Our solution focuses on the next generation of SIPs. Our technology focuses on a new class of polymers (polyglyoxylates) that depolymerize in a controlled manner in response to the cleavage of a stimulus-responsive end-cap from the polymer terminus (Fig. 1c). Unlike other polymers in this class, these materials can be prepared from commercially available or easily prepared monomers. Furthermore, they break down into environmentally benign and non-toxic products including glyoxylic acid, a metabolic intermediate in the glyoxylic acid cycle. This cycle, a variation of the tricarboxylic acid cycle, is the anabolic pathway occurring in plants, bacteria, and protists, and can convert glyoxylic acid to CO2.

Figure 1: degradation diagram

Fig. 1. Degradation diagram a) a conventional biodegradable polymer and b) a self-immolative polymer; c) Polyglyoxylate structure, depolymerisation mechanism, and products.

Competitive Advantages

• Degradation of the polymer can be triggered through external stimuli (i.e., light, redox, pH, enzymes)

• The material properties (including degradation time) can be tuned for specific applications

• The degradation by-products are and non-toxic products including glyoxylic acid, which is readily processed by plants or bacteria through the glyoxylate cycle.

Patent Status

• International PCT patent application filed in May 2015. It protects multiple polymer compositions as well as the end-caps responsible for triggering events.

Patent Information:

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