Synthesis and Biodegradation Test of a New Polyether Polyurethane Foam Produced from PEG 400, L-Lysine Ethyl Ester Diisocyanate (L-LDI) and Bis-hydroxymethyl Furan (BHMF)

Abstract

In this paper we produced a bio-based polyether-polyurethane foam PU1 through the prepolymer method. The prepolymer was obtained by the reaction of PEG 400 with L-Lysine ethyl ester diisocyanate (L-LDI). The freshly prepared prepolymer was extended with 2,5-bis(hydroxymethyl)furan (BHMF) to produce the final polyurethane. The renewable chemical BHMF was produced through the chemical reduction of HMF by sodium borohydride. HMF was produced by a previously reported procedure from fructose using choline chloride and ytterbium triflate. To evaluate the degradation rate of the foam PU1, we tested the chemical stability by soaking it in a 10% sodium hydroxide solution. The weight loss was only 12% after 30 days. After that, we proved that enzymatic hydrolysis after 30 days using cholesterol esterase was more favoured than hydrolysis with NaOH, with a weight loss of 24%, probably due to the hydrophobic character of the PU1 and a better adhesion of the enzyme on the surface with respect to water. BHMF was proved to be of crucial importance for the enzymatic degradation assay at 37 °C in phosphate buffer solution, because it represents the breaking point inside the polyurethane chain. Soil burial degradation test was monitored for three months to evaluate whether the joint activity of sunlight, climate changes and microorganisms, including bacteria and fungi, could further increase the biodegradation. The unexpected weight loss after soil burial degradation test was 45% after three months. This paper highlights the potential of using sustainable resources to produce new biodegradable materials.

The state-of-art polyurethane nanoparticles for drug delivery applications

“… (A) Synthesis of biocompatible poly (urethane) from PEG 400 and l-Lysine ( Olivito et al, 2023 ). Reused under Creative Commons Attribution License (B) Synthesis of a poly (urethane) network general representation ( Szczepańczyk et al, 2021 ).…”

Mechanical Properties and Degradation Rate of Poly(Sorbitol Adipate-Co-Dioladipate) Copolymers Obtained with a Catalyst-Free Melt Polycondensation Method

“…Utilizing degradable plastics, ideally made from renewable resources, is the obvious the first step in addressing this problem. The class of polyesters with (bio)degradable qualities now dominates various application domains [ 7 , 8 , 9 ]. Different types of enzymes, such as esterase, cutinase, and lipase, are known as being highly active for the degradation of polyester-based polymers [ 7 ].…”

Synthesis, Characterization, and Toxicity Assessment of Zinc Oxide-Doped Manganese Oxide Nanoparticles in a Macrophage Model

“…is their biopersistence [ 28 ]. More studies are now focused on synthesizing biodegradable materials, as well as understanding the underlying mechanisms of biodegradability, including Mn-based ENMs [ 28 , 29 , 30 , 31 ].…”