scholarly journals Preparation and Characterization of Self-Healing Polyurethane Powder Coating Using Diels–Alder Reaction

Polymers ◽  
2021 ◽  
Vol 13 (21) ◽  
pp. 3803
Author(s):  
Negin Farshchi ◽  
Michaela Gedan-Smolka ◽  
Markus Stommel
Keyword(s):  
Single Molecule ◽  
Cycloaddition Reaction ◽  
Film Surface ◽  
Powder Coating ◽  
Healing Time ◽  
Diels Alder ◽  
Curing Temperature ◽  
Self Healing ◽  
Melt Mixing ◽  
Cross Linker

Although powder coating systems offer many environmental, ecological and energy related benefits over liquid based coatings, in the case of uretdione based polyurethane systems, high curing temperature is still an issue. On the other hand, powder coating systems make it possible to reduce the costs and enhance the process of forming complex 3D structures using the deep drawing method by pre-coated metal substrates. During this processing method, there is a probability of micro crack formation in the coated film due to strain impact on the coating layer. A powder coating with self-healing ability is an ultimate solution to face not only this kind of fraction but also any other possible ones (such as defects caused by any impact on film surface during processing, transporting or even service). Here, a single molecule that is prepared via Diels–Alder cycloaddition reaction and retro Diels–Alder cleavage reaction was utilized as a self-healing additive to achieve self-healing ability in the powder coating system that is based on a commercially available uretdione cross-linker and OH-polyester resin. Coatings were prepared through melt mixing of components in a lab mixer, milling, sieving, and then application on the metal substrate through the electrostatic spraying method. To illustrate the role of self-healing additive, various concentrations (4 and 9% wt.) in combination with different curing temperatures (80 °C to 200 °C) were investigated. Both samples containing HA showed self-healing ability at elevated temperature around 120 °C for about 30 min with acceptable roughness and surface properties. Hardness measurement of cured film as well as thermal investigation indicate the chemical reaction of HA in a cross-linked network of cross-linker and resin. In addition, using HA leads to a 40 K drop in curing temperature of the system without using any catalyst. A 2.58% improvement in hardness values at a lower curing temperature and healing time of around 12.5 min at 120 °C to recover 100% of initial scratch (more than 10 cycles) in the sample containing 9% wt. HA was observed.

Facile fabrication of fast recyclable and multiple self-healing epoxy materials through diels-alder adduct cross-linker

2015 ◽  
Vol 53 (18) ◽  
pp. 2094-2103 ◽  
Author(s):  
Xiao Kuang ◽  
Guoming Liu ◽  
Xia Dong ◽  
Xianggui Liu ◽  
Jianjun Xu ◽  
...  
Keyword(s):  
Diels Alder ◽  
Self Healing ◽  
Facile Fabrication ◽  
Cross Linker ◽  
Alder Adduct

Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

2019 ◽  
Vol 16 (6) ◽  
pp. 527-543 ◽  
Author(s):  
Pedro M.E. Mancini ◽  
Carla M. Ormachea ◽  
María N. Kneeteman
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Ionic Conduction ◽  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
The Other ◽  
Conventional Heating ◽  
Protic Ionic Liquids ◽  
Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

Synthese neuer Pyridin-C-nukleoside der 2 ,3 -Didesoxyribose durch „inverse“ [4+2]-Cycloaddition Synthesis of Novel Pyridine-C-nucleosides of 2,3-Dideoxyribose by „Inverse“ [4+2]-Cycloaddition

1997 ◽  
Vol 52 (7) ◽  
pp. 851-858 ◽  
Author(s):  
Gunther Seitz ◽  
Johanna Siegl
Keyword(s):  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
The Novel ◽  
Protecting Group ◽  
Enol Ethers ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Cyclic Ketene Acetals

The anomeric imido esters 5 and 6, appropriate precursors for C-nucleoside synthesis, were prepared and utilized as heterodienophiles in a Diels-Alder reaction with inverse electron demand to yield the novel, protected 1.2.4-triazine C-nucleosides 8 and 9. They could be deprotected by treatment with 70% trifluoroacetic acid to furnish the free C-nucleosides 10 and 11. The triazine „aglycon“ of 8 contains an electron deficient diazadiene system, highly activated to react with various electron rich dienophiles such as enamines, enol ethers and several cyclic ketene acetals in an „inverse“ [4+2]-cycloaddition reaction. The Diels-Alder adducts spontaneously eliminate N2 and after follow-up reactions the O-TBDPS protected pyridine-C-nucleosides 13, 15, 17,19, 21 and 23 are formed. Removal of the protecting group by treatment with CF3CO2H /H2O leads to the corresponding 2’,3’-dideoxy-β-D-ribofuranosyl- pyridines.

Self-Healing Hydrophobic POSS-functionalized Fluorinated Copolymer via RAFT Polymerization and dynamic Diels-Alder Reaction

2021 ◽  
Author(s):  
Siva Ponnupandian ◽  
Prantik Mondal ◽  
Thomas Becker ◽  
Richard Hoogenboom ◽  
Andrew B Lowe ◽  
...  
Keyword(s):  
Chain Transfer ◽  
Raft Polymerization ◽  
Alder Reaction ◽  
Diels Alder ◽  
Self Healing ◽  
Diels Alder Reaction ◽  
Reversible Addition

This investigation reports the preparation of a tailor-made copolymer of furfuryl methacrylate (FMA) and trifluoroethyl methacrylate (TFEMA) via reversible addition-fragmentation chain transfer (RAFT) polymerization. The furfuryl groups of the copolymer...

scholarly journals Furoic Acid and Derivatives as Atypical Dienes in Diels-Alder Reactions

2021 ◽  
Author(s):  
Razvan Cioc ◽  
Tom Smak ◽  
Marc Crockatt ◽  
Jan Kees Van der Waal ◽  
Pieter C A Bruijnincx
Keyword(s):  
Green Chemistry ◽  
Cycloaddition Reaction ◽  
Building Blocks ◽  
Diels Alder ◽  
Furoic Acid

The furan Diels-Alder (DA) cycloaddition reaction has become an important tool in green chemistry, being central to the sustainable synthesis of many chemical building blocks. The restriction to electron-rich furans...

scholarly journals Recyclable Self-Healing Polyurethane Cross-Linked by Alkyl Diselenide with Enhanced Mechanical Properties

Polymers ◽  
2019 ◽  
Vol 11 (5) ◽  
pp. 773 ◽  
Author(s):  
Yuqing Qian ◽  
Xiaowei An ◽  
Xiaofei Huang ◽  
Xiangqiang Pan ◽  
Jian Zhu ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Room Temperature ◽  
Amide Bond ◽  
Self Healing ◽  
Healing Efficiency ◽  
Polyurethane Networks ◽  
Combined Action ◽  
Cross Linker ◽  
Dynamic Structures ◽  
External Interventions

Dynamic structures containing polymers can behave as thermosets at room temperature while maintaining good mechanical properties, showing good reprocessability, repairability, and recyclability. In this work, alkyl diselenide is effectively used as a dynamic cross-linker for the design of self-healing poly(urea–urethane) elastomers, which show quantitative healing efficiency at room temperature, without the need for any catalysts or external interventions. Due to the combined action of the urea bond and amide bond, the material has better mechanical properties. We also compared the self-healing effect of alkyl diselenide-based polyurethanes and alkyl disulfide-based polyurethanes. The alkyl diselenide has been incorporated into polyurethane networks using a para-substituted amine diphenyl alkyl diselenide. The resulting materials not only exhibit faster self-healing properties than the corresponding disulfide-based materials, but also show the ability to be processed at temperatures as low as 60 °C.

scholarly journals Mechanochemically Gated Photoswitching: Expanding the Scope of Polymer Mechanochromism

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1725-1732 ◽  
Author(s):  
Ross W. Barber ◽  
Molly E. McFadden ◽  
Xiaoran Hu ◽  
Maxwell J. Robb
Keyword(s):  
Mechanical Activation ◽  
Uv Light ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Diels Alder ◽  
Information Storage ◽  
Chemical Transformations ◽  
History Of ◽  
Polymer Mechanochemistry ◽  
Stress Sensing

Mechanophores are molecules that undergo productive, covalent chemical transformations in response to mechanical force. Over the last decade, a variety of mechanochromic mechanophores have been developed that enable the direct visualization of stress in polymers and polymeric materials through changes in color and chemiluminescence. The recent introduction of mechanochemically gated photoswitching extends the repertoire of polymer mechanochromism by decoupling the mechanical activation from the visible response, enabling the mechanical history of polymers to be recorded and read on-demand using light. Here, we discuss advances in mechanochromic mechanophores and present our design of a cyclopentadiene–maleimide Diels–Alder adduct that undergoes a force-induced retro-[4+2] cycloaddition reaction to reveal a latent diarylethene photoswitch. Following mechanical activation, UV light converts the colorless diarylethene molecule into the colored isomer via a 6π-electrocyclic ring-closing reaction. Mechanically gated photoswitching expands on the fruitful developments in mechanochromic polymers and provides a promising platform for further innovation in materials applications including stress sensing, patterning, and information storage.1 Introduction to Polymer Mechanochemistry2 Mechanochromic Reactions for Stress Sensing3 Regiochemical Effects on Mechanophore Activation4 Mechanochemically Gated Photoswitching5 Conclusions

Self-healing poly(siloxane-urethane) elastomers with remoldability, shape memory and biocompatibility

2016 ◽  
Vol 7 (47) ◽  
pp. 7278-7286 ◽  
Author(s):  
Jian Zhao ◽  
Rui Xu ◽  
Gaoxing Luo ◽  
Jun Wu ◽  
Hesheng Xia
Keyword(s):  
Mechanical Property ◽  
Shape Memory ◽  
Microphase Separation ◽  
Diels Alder ◽  
Good Mechanical Property ◽  
Self Healing ◽  
Healing Efficiency ◽  
Good Biocompatibility

The poly(siloxane-urethane) elastomers with microphase separation structure and Diels–Alder bonds show high healing efficiency, good mechanical property and good biocompatibility.

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