Related Experiment Video
Updated: Oct 26, 2025
09:06
Evaluation of the Curing of Adhesive Systems by Rheological and Thermal Testing
Published on: July 3, 2020
7.4K
Structural Variation and Chemical Performance-A Study of the Effects of Chemical Structure upon Epoxy Network
Stephen T Knox1, Anthony Wright2, Colin Cameron2
1Department of Mechanical Engineering, University of Sheffield, Sheffield S1 4BJ, U.K.
ACS Applied Polymer Materials
|July 26, 2021
Summary
Structural variations in epoxy and amine monomers significantly impact chemical resistance. Bisphenol F resins and aromatic amines offer superior performance in protective coatings compared to bisphenol A resins and aliphatic amines.
Area of Science:
- Polymer Chemistry
- Materials Science
- Chemical Engineering
Background:
- Epoxy resins are crucial for protective coatings in harsh chemical environments.
- Understanding monomer structure-property relationships is key to enhancing network performance.
- Previous research has focused on general epoxy formulations, with less emphasis on subtle monomer variations.
Purpose of the Study:
- To investigate how structural variations in epoxy and amine monomers affect the chemical resistance of cured networks.
- To identify specific monomer features that improve the performance of epoxy-based protective coatings.
Main Methods:
- Utilized four industrial epoxy resins: two bisphenol A-based (E828, DER 332) and two bisphenol F-based (DER 354, PY306), plus para-para-diglycidyl ether of bisphenol F (ppDGEBF).
- Employed four amine curing agents: meta-xylylenediamine (MXDA), para-xylylenediamine (PXDA), 1,3-bis(aminomethyl)cyclohexane (1,3-BAC), and 1,4-bis(aminomethyl)cyclohexane (1,4-BAC).
- Evaluated chemical performance of the resulting cured epoxy networks.
Main Results:
- Bisphenol F-based epoxy resins demonstrated superior chemical resistance compared to bisphenol A-based analogues.
- Increased chain length within the epoxy monomer structure negatively impacted chemical performance.
- Aromatic amine structures and 1,3-substitution patterns (e.g., MXDA) enhanced the chemical resistance of the cured networks.
Conclusions:
- Subtle structural modifications in epoxy and amine monomers significantly influence the chemical performance of protective coatings.
- Bisphenol F epoxy resins and aromatic amines with specific substitution patterns are recommended for applications requiring high chemical resistance.
- Further research can leverage these findings for the design of advanced epoxy-based materials.
More Related Videos
Related Concept Videos
02:24Acid-Catalyzed Ring-Opening of Epoxides
7.9K
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...
7.9K
02:38Structure and Nomenclature of Epoxides
7.1K
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...
7.1K
01:14Polymer Classification: Architecture
3.4K
Polymers are classified as linear or branched on the basis of their chain architecture. The polymer chains in linear polymers have a long chain-like structure with minimal to no branching at all. Even if a polymer features large substituent groups on the monomer, which appear as branches to the skeleton, it is not considered a branched polymer. A branched polymer contains secondary polymer chains that arise from the main polymer chain. The branching occurs when the polymer growth shifts from...
3.4K
02:26Base-Catalyzed Ring-Opening of Epoxides
9.1K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
9.1K
01:26Polymer Classification: Stereospecificity
2.9K
Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
2.9K
03:00Preparation of Epoxides
8.3K
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...
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...
8.3K