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.

scholarly journals First Example of Unsaturated Poly(Ester Amide)s Derived From Itaconic Acid and Their Application as Bio-Based UV-Curing Polymers

2020 ◽  
Vol 10 (6) ◽  
pp. 2163 ◽  
Author(s):  
Rim Ouhichi ◽  
Sacha Pérocheau Arnaud ◽  
Abdelkader Bougarech ◽  
Souhir Abid ◽  
Majdi Abid ◽  
...  
Keyword(s):  
Double Bond ◽  
Itaconic Acid ◽  
Michael Addition ◽  
Addition Reaction ◽  
Ultra Violet ◽  
Uv Curing ◽  
Building Blocks ◽  
Amide Group ◽  
Polyester Resins ◽  
Printing Inks

Recently, itaconic acid has drawn considerable attention as a novel radical-curing building block for polyester resins. These bio-based materials have been used in thermal, as well as ultra violet (UV) curing applications, such as printing inks or coatings. Poly(ester amide)s from itaconic acid could be very interesting, as the amide group could alter the properties of the resins as well as cured materials. However, standard polycondensation reactions with diamines are not possible with itaconic acid as the amines preferably react via an aza-Michael addition at the α,β-unsaturated double bond. Therefore, alternative and more elaborate synthetic strategies have to be developed. Herein, we present two different synthetic strategies to poly(ester amide)s from itaconic acid that circumvent the addition reaction of the amines. This is in both cases done by a pre-reaction to form stable amide building blocks that are then reacted with itaconic acid or polyesters derived thereof. The structural composition and the properties of the resin are characterized, and the UV-curing reactivity is examined. All properties are compared to corresponding polyesters from itaconic acid.

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 Synthesis, Characterization and Testing of Antimicrobial Activity of Composites of Unsaturated Polyester Resins with Wood Flour and Silver Nanoparticles

Materials ◽  
2021 ◽  
Vol 14 (5) ◽  
pp. 1122
Author(s):  
Przemysław Pączkowski ◽  
Andrzej Puszka ◽  
Malgorzata Miazga-Karska ◽  
Grażyna Ginalska ◽  
Barbara Gawdzik
Keyword(s):  
Silver Nanoparticles ◽  
Staphylococcus Epidermidis ◽  
Polyester Resin ◽  
Wood Flour ◽  
Unsaturated Polyester ◽  
Thermomechanical Properties ◽  
Resin Composites ◽  
Polyester Resins ◽  
Before And After

This paper presents the properties of the wood-resin composites. For improving their antibacterial character, silver nanoparticles were incorporated into their structures. The properties of the obtained materials were analyzed in vitro for their anti-biofilm potency in contact with aerobic Gram-positive Staphylococcus aureus and Staphylococcus epidermidis; and aerobic Gram-negative Escherichia coli and Pseudomonas aeruginosa. These pathogens are responsible for various infections, including those associated with healthcare. The effect of silver nanoparticles incorporation on mechanical and thermomechanical properties as well as gloss were investigated for the samples of composites before and after accelerating aging tests. The results show that bacteria can colonize in various wrinkles and cracks on the composites with wood flour but also the surface of the cross-linked unsaturated polyester resin. The addition of nanosilver causes the death of bacteria. It also positively influences mechanical and thermomechanical properties as well as gloss of the resin.

scholarly journals Thioesters Provide a Robust Path to Prebiotic Peptides

2021 ◽  
Author(s):  
Moran Frenkel-Pinter ◽  
Marcos Bouza ◽  
Facundo M. Fernández ◽  
Luke J. Leman ◽  
Loren Dean Williams ◽  
...  
Keyword(s):  
Building Blocks ◽  
Peptide Bond ◽  
Side Reactions ◽  
Peptide Bond Formation ◽  
One Pot ◽  
Complex Molecules ◽  
Peptide Formation ◽  
Wide Range ◽  
Amide Exchange ◽  
Prebiotic Earth

The condensation of building blocks into oligomers and polymers was an early and important stage in the origins of life. High activation energies, unfavorable thermodynamics and side reactions are bottlenecks for abiotic formation of peptides. Thioesters are hypothesized to have played key roles in prebiotic chemistry on early Earth, serving as energy storing molecules, as synthetic intermediates, and as catalysts in the formation of more complex molecules, including polypeptides. However, all abiotic reactions reported thus far for peptide formation via thioester intermediates have relied on activated building blocks or condensing agents, which are of questionable prebiotic relevance. We report robust, plausible prebiotic reactions of mercaptoacids with amino acids that result in the formation of peptides and thiodepsipeptides, which contain both peptide and thioester bonds. Peptide bond formation proceeds by the condensation of mercaptoacids to form thioesters followed by thioester-amide exchange. Mercaptoacids catalyze thiodepsipeptides and peptide formation under a wide range of pH conditions and at mild temperatures. Our results offer the most robust one-pot pathway for peptide formation ever reported. These results support the hypothesis that thiodepsipeptides formed robustly on prebiotic Earth and were possible contributors to early chemical evolution.

scholarly journals High expression of VRT2 during wheat spikelet initiation increases the number of rudimentary basal spikelets

2021 ◽  
Author(s):  
Anna E Backhaus ◽  
Ashleigh Lister ◽  
Melissa Tomkins ◽  
Nikolai M. Adamski ◽  
James Simmonds ◽  
...  
Keyword(s):  
Gene Expression ◽  
Expression Profiles ◽  
Computational Modelling ◽  
Gene Expression Profiles ◽  
Building Blocks ◽  
Field Trials ◽  
Developmental Genetics ◽  
Spatially Resolved ◽  
Before And After ◽  
Single Spike

Spikelets are the fundamental building blocks of Poaceae inflorescences and their development and branching patterns determine the various inflorescence architectures and grain yield of grasses. In wheat, the central spikelets produce the most and largest grains, while spikelet size gradually decreases acro- and basipetally, giving rise to the characteristic lanceolate shape of wheat spikes. The acropetal gradient correlates with the developmental age of spikelets, however the basal spikelets are developed first and the cause of their small size and rudimentary development is unclear. Here, we adapted G&T-seq, a low-input transcriptomics approach, to characterise gene expression profiles within spatial sections of individual spikes before and after the establishment of the lanceolate shape. We observed larger differences in gene expression profiles between the apical, central and basal sections of a single spike than between any section belonging to consecutive developmental timepoints. We found that SVP MADS-box transcription factors, including VRT-A2, are expressed highest in the basal section of the wheat spike and display the opposite expression gradient to flowering E-class SEP1 genes. Based on multi-year field trials and transgenic lines we show that higher expression of VRT-A2 in the basal sections of the spike is associated with increased numbers of rudimentary basal spikelets. Our results, supported by computational modelling, suggest that the delayed transition of basal spikelets from vegetative to floral developmental programmes results in the lanceolate shape of wheat spikes. This study highlights the value of spatially resolved transcriptomics to gain new insights into developmental genetics pathways of grass inflorescences.

scholarly journals Biocatalysis for terpene-based polymers

2019 ◽  
Vol 74 (3-4) ◽  
pp. 91-100 ◽  
Author(s):  
Wissam Farhat ◽  
Arne Stamm ◽  
Maxime Robert-Monpate ◽  
Antonino Biundo ◽  
Per-Olof Syrén
Keyword(s):  
Renewable Resources ◽  
Building Blocks ◽  
Synthetic Polymers ◽  
Model System ◽  
Advanced Materials ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

Abstract Accelerated generation of bio-based materials is vital to replace current synthetic polymers obtained from petroleum with more sustainable options. However, many building blocks available from renewable resources mainly contain unreactive carbon-carbon bonds, which obstructs their efficient polymerization. Herein, we highlight the potential of applying biocatalysis to afford tailored functionalization of the inert carbocyclic core of multicyclic terpenes toward advanced materials. As a showcase, we unlock the inherent monomer reactivity of norcamphor, a bicyclic ketone used as a monoterpene model system in this study, to afford polyesters with unprecedented backbones. The efficiencies of the chemical and enzymatic Baeyer–Villiger transformation in generating key lactone intermediates are compared. The concepts discussed herein are widely applicable for the valorization of terpenes and other cyclic building blocks using chemoenzymatic strategies.

Selective enzymatic transformations of itaconic acid derivatives: An access to potentially useful building blocks

Tetrahedron ◽  
1994 ◽  
Vol 50 (10) ◽  
pp. 3251-3258 ◽  
Author(s):  
Patrizia Ferraboschi ◽  
Silvana Casati ◽  
Paride Grisenti ◽  
Enzo Santaniello
Keyword(s):  
Itaconic Acid ◽  
Building Blocks

scholarly journals Value-Added Bio-Chemicals Commodities from Catalytic Conversion of Biomass Derived Furan-Compounds

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 895
Author(s):  
Aitziber Iriondo ◽  
Ion Agirre ◽  
Nerea Viar ◽  
Jesús Requies
Keyword(s):  
Renewable Resources ◽  
Petrochemical Industry ◽  
Raw Materials ◽  
Value Added ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Potential Market ◽  
Forestry Residues ◽  
Industry Needs ◽  
Near Future

The depletion of fossil resources in the near future and the need to decrease greenhouse gas emissions lead to the investigation of using alternative renewable resources as raw materials. One of the most promising options is the conversion of lignocellulosic biomass (like forestry residues) into bioenergy, biofuels and biochemicals. Among these products, the production of intermediate biochemicals has become an important goal since the petrochemical industry needs to find sustainable alternatives. In this way, the chemical industry competitiveness could be improved as bioproducts have a great potential market. Thus, the main objective of this review is to describe the production processes under study (reaction conditions, type of catalysts, solvents, etc.) of some promising intermediate biochemicals, such as; alcohols (1,2,6-hexanetriol, 1,6-hexanetriol and pentanediols (1,2 and 1,5-pentanediol)), maleic anhydride and 5-alkoxymethylfuran. These compounds can be produced using 5-hydroxymethylfurfural and/or furfural, which they both are considered one of the main biomass derived building blocks.

Synthesis of Macrocycles with Anthracene Units and Amide Bonds; Potential Building Blocks for 1D and 2D Constructions

Synlett ◽  
2012 ◽  
Vol 23 (10) ◽  
pp. 1467-1472 ◽  
Author(s):  
Junji Sakamoto ◽  
A. Schlüter ◽  
Animesh Saha ◽  
Jeroen van Heijst
Keyword(s):  
Building Blocks ◽  
Amide Bonds

scholarly journals Protein nanofibrils and their use as building blocks of sustainable materials

RSC Advances ◽  
2021 ◽  
Vol 11 (62) ◽  
pp. 39188-39215
Author(s):  
Christofer Lendel ◽  
Niclas Solin
Keyword(s):  
Sustainable Development ◽  
Renewable Resources ◽  
Building Blocks ◽  
Novel Materials ◽  
Sustainable Materials

Protein nanofibrils produced from renewable resources provide opportunities to create novel materials for sustainable development.

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