scholarly journals Enzymatic Synthesis of Muconic Acid-Based Polymers: Trans, Trans-Dimethyl Muconate and Trans, β-Dimethyl Hydromuconate

Polymers ◽  
2021 ◽  
Vol 13 (15) ◽  
pp. 2498
Author(s):  
Dina Maniar ◽  
Csaba Fodor ◽  
Indra Karno Adi ◽  
Albert J. J. Woortman ◽  
Jur van Dijken ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Renewable Resources ◽  
Enzymatic Synthesis ◽  
Enzyme Catalysis ◽  
Unsaturated Polyester ◽  
Chain Extension ◽  
Side Reactions ◽  
Muconic Acid ◽  
Thermal Stabilities ◽  
Polyester Resins

The vast majority of commodity polymers are acquired from petrochemical feedstock, and these resources will plausibly be depleted within the next 100 years. Therefore, the utilization of carbon-neutral renewable resources for the production of polymers is crucial in modern green chemistry. Herein, we report an eco-friendly strategy that uses enzyme catalysis to design biobased unsaturated (co)polyesters from muconic acid derivatives. This method is an attractive pathway for the production of well-defined unsaturated polyesters with minimum side reactions. A suite of characterization techniques was performed to probe the reaction mechanism and properties of the obtained polyesters. It is rationalized that the alkene functionality of the muconate monomers plays an important role in the enzyme catalysis mechanism. The rendered polyesters possessed excellent thermal stabilities and unreacted alkene functionality that can consecutively undergo chain extension, copolymerization, or act as an anchor for other functional groups. These properties open new avenues in the fields of unsaturated polyester resins and photosensitive coatings.

scholarly journals Optimization of Reactive Diluent for Bio-Based Unsaturated Polyester Resin: A Rheological and Thermomechanical Study

Polymers ◽  
2021 ◽  
Vol 13 (16) ◽  
pp. 2667
Author(s):  
Pavle Spasojevic ◽  
Sanja Seslija ◽  
Maja Markovic ◽  
Olga Pantic ◽  
Katarina Antic ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Methyl Methacrylate ◽  
Rheological Properties ◽  
Renewable Resources ◽  
Polyester Resin ◽  
Unsaturated Polyester ◽  
High Viscosity ◽  
Reactive Diluent ◽  
Polyester Resins ◽  
Continuous Demand

Nowadays, unsaturated polyester resins (UPR) are mainly obtained from non-renewable resources. The ever-increasing regulations and the continuous demand for more sustainability have led to extensive research towards more environmentally suitable alternatives to petroleum-based materials. However, one of the main disadvantages of bio-based UPR is their relatively high viscosity compared to petrochemical ones. In order to overcome this drawback, in this work, we investigated the possibility to lower the resin viscosity utilizing a mixture of dimethyl itaconate (DMI) and methyl methacrylate (MMA) as a reactive diluent. The effect of the DMI and MMA ratio on resin rheological properties was investigated. The optimal curing parameters were determined and all UPRs had a high gel content, which was shown to be dependent on the DMI and MMA ratio in the formulation. Furthermore, thermomechanical and mechanical properties of the resulting network were also found to be affected by the used reactive diluent mixture. A small substitution of DMI by MMA proved to be advantageous since it offers lower resin viscosity and improved mechanical properties.

scholarly journals Straightforward Synthetic Protocol to Bio-Based Unsaturated Poly(ester amide)s from Itaconic Acid with Thixotropic Behavior

Polymers ◽  
2020 ◽  
Vol 12 (4) ◽  
pp. 980 ◽  
Author(s):  
Lazaros Papadopoulos ◽  
Marcel Kluge ◽  
Dimitrios N. Bikiaris ◽  
Tobias Robert
Keyword(s):  
Itaconic Acid ◽  
Renewable Resources ◽  
Uv Curing ◽  
Building Blocks ◽  
Side Reactions ◽  
Addition Reactions ◽  
Polyester Resins ◽  
Amide Bonds ◽  
Before And After ◽  
Thixotropic Behavior

In the field of polymer chemistry, tremendous efforts have been made over the last decade to replace petrochemical monomers with building blocks from renewable resources. In this respect, itaconic acid has been used as an alternative to acrylic acid or maleic acid in unsaturated polyesters for thermal or UV-curing applications. However, examples of poly(ester amide)s from itaconic acid are scarce. Under standard polycondensation reactions, the presence of free amines leads to aza-Michael addition reactions at the α,β-unsaturated double bond of the itaconic acid and isomerization reactions to mesaconic acid. Both reactions make the resulting materials useless as UV-curing polymer resins. To avoid these undesired side reactions, we herein report the use of preformed, well-defined diols containing internal amide bonds. The resulting unsaturated poly(ester amide) resins were analyzed before and after UV-induced crosslinking. Viscosity measurements revealed a strong thixotropic behavior induced by the amide groups, which is usually not detected in structurally similar polyester resins.

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