scholarly journals Production of a PET//LDPE Laminate Using a Reversibly Crosslinking Packaging Adhesive and Recycling in a Small-Scale Technical Plant

Recycling ◽  
2021 ◽  
Vol 6 (3) ◽  
pp. 47
Author(s):  
Katharina M. A. Kaiser ◽  
Tanja Ginzinger
Keyword(s):  
Molecular Weight ◽  
Pilot Plant ◽  
Alder Reaction ◽  
Diels Alder ◽  
Infrared Spectrometry ◽  
Small Scale ◽  
Scanning Calorimetry ◽  
Melt Index ◽  
Diels Alder Reaction ◽  
Pilot Plant Scale

Multilayer packaging is an important part of the packaging market, but it is not recyclable with conventional methods since it is made of different thermodynamically immiscible materials. In this work, it was shown that it is possible to produce a PET//LDPE laminate in a pilot plant for lamination by using an adhesive consisting of maleimide- and furan-functionalized polyurethane prepolymers that cure through the Diels–Alder reaction. The material could then be delaminated in a small-scale recycling plant using a solvent-based recycling process by partially opening the Diels–Alder adducts through the influence of temperature. The PET and LDPE could be recovered without any adhesive residues before each material was regranulated, and in the case of the PE, a film was produced via cast film extrusion. The obtained PET granulate exhibited a slight, approximately 10%, decrease in molecular weight. However, since small amounts of LDPE could not be separated, compatibilization would still be required here for further use of the material. The obtained LDPE film was characterized by means of infrared spectrometry, differential scanning calorimetry, tensile testing, determination of the melt index, and molecular weight. The film showed lower crosslinking than usual for LDPE recycling and exhibited good mechanical properties. In this work, it was thus shown that upscaling of the laminate production with the modified adhesive and also its recycling at the pilot plant scale is possible and thus could be an actual option for recycling multilayer packaging.

scholarly journals Influence of the Glass Transition Temperature and the Density of Crosslinking Groups on the Reversibility of Diels-Alder Polymer Networks

Polymers ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1189
Author(s):  
Merlina Thiessen ◽  
Volker Abetz
Keyword(s):  
Glass Transition ◽  
Transition Temperature ◽  
Glass Transition Temperature ◽  
Radical Polymerization ◽  
Polymer Networks ◽  
Alder Reaction ◽  
Diels Alder ◽  
Self Healing ◽  
Scanning Calorimetry ◽  
Diels Alder Reaction

The interest in self-healing, recyclable, and adaptable polymers is growing. This work addresses the reversibility of crosslink formation based on Diels-Alder reaction in copolymer networks containing furfuryl and maleimide groups, which represent the “diene” and the “dienophile,” respectively. The copolymers are synthesized by atom transfer radical polymerization (ATRP) and free radical polymerization. The diene bearing copolymers are crosslinked either with a small molecule containing two dienophiles or with a dienophile bearing copolymer. The influence of the crosslinking temperature on the Diels-Alder reaction is analyzed. Furthermore, the influence of the glass transition temperature and the influence of the density of crosslinking groups on the thermo-reversibility of crosslinking are investigated by temperature dependent infrared spectroscopy and differential scanning calorimetry. It is shown that the reversibility of crosslinking is strongly influenced by the glass transition temperature of the system.

scholarly journals Thermally Self-Healing Graphene-Nanoplate/Polyurethane Nanocomposites via Diels–Alder Reaction through a One-Shot Process

Nanomaterials ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 434 ◽  
Author(s):  
Cho-Rong Oh ◽  
Sang-Hyub Lee ◽  
Jun-Hong Park ◽  
Dai-Soo Lee
Keyword(s):  
Molecular Design ◽  
Alder Reaction ◽  
Chain Extender ◽  
Diels Alder ◽  
Self Healing ◽  
Scanning Calorimetry ◽  
Diels Alder Reaction ◽  
A Chain ◽  
The Fourier Transform

Thermally self-healing graphene-nanoplate/polyurethane (GNP/PU) nanocomposites were prepared via a bulk in-situ Diels–Alder (DA) reaction. Graphene-nanoplate (GNP) was used as a reinforcement and crosslinking platform by a DA reaction with a furfuryl-based chain extender of polyurethane (PU). Results showed that a DA reaction occurred in GNP during the PU forming cure process. This procedure is simple and solvent free because of the absence of any independent surface modification process. Through the calculation of the interfacial tensions, the conditions of the bulk in-situ DA reaction were determined to ensure that GNP and the furfuryl group can react with each other at the interface during the curing process without a solvent. The prepared composites were characterized in terms of thermal, mechanical, and thermally self-healing properties via the DA reaction. In the PU capable of a DA reaction (DPU), characteristic peaks of DA and retro DA reactions were observed in the Fourier transform infrared (FT-IR) spectroscopy and endothermic peaks of retro DA reactions appeared in differential scanning calorimetry (DSC) thermograms. The DPU showed significantly enhanced physical properties and chemical resistance. The thermally self-healing capability was confirmed at 110 °C via the retro DA reactions. It is inferred that thermally self-healable crosslinked GNP/PU nanocomposites via DA reactions could be prepared in a simple bulk process through the molecular design of a chain extender for the in-situ reaction at the interface.

scholarly journals Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction

Polymers ◽  
2021 ◽  
Vol 13 (12) ◽  
pp. 1935
Author(s):  
Elena Platonova ◽  
Islam Chechenov ◽  
Alexander Pavlov ◽  
Vitaliy Solodilov ◽  
Egor Afanasyev ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Differential Scanning Calorimetry ◽  
Nmr Spectroscopy ◽  
Young Modulus ◽  
Alder Reaction ◽  
Significant Loss ◽  
Diels Alder ◽  
Scanning Calorimetry ◽  
Diels Alder Reaction

We prepared a series of thermally remendable and recyclable polyurethanes crosslinked via reversible furan-maleimide Diels–Alder reaction based on TDI end-caped branched Voranol 3138 terminated with difurfurylamine and 4,4′-bis(maleimido)diphenylmethane (BMI). We showed that Young modulus strongly depends on BMI content (from 8 to 250 MPa) that allows us to obtain materials of different elasticity as simple as varying BMI content. The ability of DA and retro-DA reactions between furan and maleimide to reversibly bind material components was investigated by NMR spectroscopy, differential scanning calorimetry, and recycle testing. All polymers obtained demonstrated high strengths and could be recovering without significant loss in mechanical properties for at least five reprocessing cycles.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Asymmetric Syntheses ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

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