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Related Concept Videos

Phosphodiester Linkages01:01

Phosphodiester Linkages

Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Peptide Bonds02:43

Peptide Bonds

A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...

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Wet Chemistry and Peptide Immobilization on Polytetrafluoroethylene for Improved Cell-adhesion
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Trans-Phosphonamidate Exchange Enables Epoxy Covalent Adaptable Networks with Intrinsic Fire Safety.

Cédric Hervieu1, Ton Markaj1, Arvindh Sekar1

  • 1Advanced Fibers Laboratory, Swiss Federal Laboratories for Materials Science and Technology (Empa), Lerchenfeldstrasse 5, St. Gallen 9014, Switzerland.

ACS Applied Materials & Interfaces
|July 9, 2026
PubMed
Summary

This study introduces phosphonamidate-based covalent adaptable networks (CANs) for sustainable thermosets. These recyclable materials offer excellent fire safety and maintain performance after multiple reprocessing cycles.

Keywords:
epoxy-based CANsflame retardantsphosphonamidaterecyclabilitytrans-phosphonamidate exchange

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Sustainable Chemistry

Background:

  • Thermoset materials face a trade-off between sustainability (recyclability) and fire safety.
  • Existing flame retardants can compromise material performance or recyclability.

Purpose of the Study:

  • To develop novel covalent adaptable networks (CANs) using phosphonamidate chemistry.
  • To integrate recyclability, intrinsic flame retardancy, and high performance in thermoset materials.

Main Methods:

  • Synthesis of phosphonamidate-based curing agents.
  • Formation of epoxy-based CANs utilizing trans-phosphonamidate exchange.
  • Evaluation of recyclability, flame retardancy (UL-94 V-0), thermal stability, and mechanical properties.
  • Fabrication of carbon-fiber-reinforced composites.

Main Results:

  • Phosphonamidate CANs demonstrate efficient reprocessing with no performance loss over five cycles.
  • Achieved UL-94 V-0 flame retardancy at low phosphorus content (2 wt%) with reduced heat release.
  • Flame retardancy was maintained after recycling.
  • Tunable thermal properties and robust mechanical performance were observed.
  • Successful fabrication of high-performance composites.

Conclusions:

  • Phosphonamidate hardeners offer a versatile platform for creating recyclable and fire-safe thermosets.
  • This approach overcomes the sustainability-fire safety compromise in advanced materials.
  • The developed CANs show significant potential for structural applications.