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Epoxy resins are reactive intermediates used to produce a versatile class of thermosetting polymers. They are characterized by the presence of a three‐membered cyclic ether group commonly referred to as an epoxy group, 1,2‐epoxide, or oxirane. The most widely used epoxy resins are diglycidyl ethers of bisphenol A derived from bisphenol A and epichlorohydrin. The outstanding performance characteristics of the thermosets derived from bisphenol A epoxies are largely conveyed by the bisphenol A moiety (toughness, rigidity, and elevated temperature performance), the ether linkages (chemical resistance), and the hydroxyl and epoxy groups (adhesive agents). In addition to bisphenol A, other starting materials such as aliphatic glycols and both phenol and
o
‐cresol novolacs are used to produce specialty resins. Epoxy resins may also include epoxide‐bearing compounds based on aromatic amine, triazine, and cycloaliphatic backbones.
A variety of reagents have been described for converting the liquid and solid epoxy resins to the cured state, which is necessary for the development of the ultimate end‐use properties. The curing agents or hardeners are categorized as either catalytic or coreactive. Catalytic curing agents initiate resin homopolymerization, either cationic or anionic, as a consequence of using a Lewis acid or base in the curing process. Coreactive curing agents are polyfunctional compounds typically possessing active hydrogens that are employed up to stoichiometric quantities with epoxy resins. The important classes of coreactive curing agents include multifunctional amines and their amide derivatives, polyphenols, polymeric thiols, polycarboxylic acids, anhydrides, phenol–formaldehyde novolacs and resoles, and amino–formaldehyde resins.
The largest single use of epoxy resins is in the protective coatings market where high corrosion resistance and adhesion to substrates are important. Epoxies have gained wide acceptance in protective coatings and in electrical and structural applications because of their exceptional combination of properties such as toughness, adhesion, chemical and thermal resistance, and good electrical properties.
The article contains sections titled:
1.
Introduction
2.
History
3.
Industry Overview
4.
Classes of Epoxy Resins and Manufacturing Processes
5.
Liquid Epoxy Resins (DGEBA)
5.1.
Caustic Coupling Process
5.2.
Phase‐Transfer Catalyst Process
6.
Solid Epoxy Resins Based on DGEBA
6.1.
SER Continuous Advancement Process
6.2.
Phenoxy Resins
6.3.
Epoxy‐Based Thermoplastics
7.
Halogenated Epoxy Resins
7.1.
Brominated Bisphenol A Based Epoxy Resins
7.2.
Fluorinated Epoxy Resins
8.
Multifunctional Epoxy Resins
8.1.
Epoxy Novolac Resins
8.1.1.
Bisphenol F Epoxy Resin
8.1.2.
Cresol Epoxy Novolacs
8.1.3.
Glycidyl Ethers of Hydrocarbon Epoxy Novolacs
8.1.4.
Bisphenol A Epoxy Novolacs
8.2.
Other Polynuclear Phenol Glycidyl Ether Derived Resins
8.2.1.
Glycidyl Ether of Tetrakis(4‐hydroxyphenyl)ethane
8.2.2.
Trisphenol Epoxy Novolacs
8.3.
Aromatic Glycidyl Amine Resins
8.3.1.
Triglycidyl Ether of
p
‐Aminophenol
8.3.2.
Tetraglycidyl Methylenedianiline (MDA)
9.
Specialty Epoxy Resins
9.1.
Crystalline Epoxy Resins Development
9.2.
Weatherable Epoxy Resins
9.2.1.
Hydrogenated DGEBA
9.2.2.
Heterocyclic Glycidyl Imides and Amides
9.2.3.
Hydantoin‐Based Epoxy Resins
9.3.
Elastomer‐Modified Epoxies
10.
Monofunctional Glycidyl Ethers and Aliphatic Glycidyl Ethers
11.
Cycloaliphatic Epoxy Resins and Epoxidized Vegetable Oils
12.
Epoxy Esters and Derivatives
12.1.
Epoxy Esters
12.2.
Glycidyl Esters
12.3.
Epoxy Acrylates
12.4.
Epoxy Vinyl Esters
12.5.
Epoxy Phosphate Esters
13.
Characterization of Uncured Epoxies
14.
Curing of Epoxy Resins
15.
Coreactive Curing Agents
15.1.
Amine Functional Curing Agents
15.1.1.
Primary and Secondary Amines
15.1.1.1.
Aliphatic Amines
15.1.1.1.1.
Ketimines
15.1.1.1.2.
Mannich Base Adducts
15.1.1.1.3.
Polyetheramines
15.1.1.2.
Cycloaliphatic Amines
15.1.1.3.
Aromatic Amines
15.1.1.4.
Arylyl Amines
15.1.2.
Polyamides
15.1.3.
Amidoamines
15.1.4.
Dicyandiamide
15.2.
Carboxylic Functional Polyester and Anhydride Curing Agents
15.2.1.
Carboxylic Functional Polyesters
15.2.2.
Acid Anhydrides
15.3.
Phenolic‐Terminated Curing Agents
15.4.
Melamine‐, Urea‐, and Phenol‐Formaldehyde Resins
15.5.
Mercaptans (Polysulfides and Polymercaptans) Curing Agents
15.6.
Cyclic Amidines Curing Agents
15.7.
Isocyanate Curing Agents
15.8.
Cyanate Ester Curing Agents
16.
Catalytic Cure
16.1.
Lewis Bases
16.2.
Lewis Acids
16.3.
Photoinitiated Cationic Cure
17.
Formulation Development With Epoxy Resins
17.1.
Relationship Between Cured Epoxy Resin Structure and Properties
17.2.
Selection of Epoxy Resins
17.3.
Selection of Curing Agents
17.4.
Epoxy/Curing Agent Stoichiometric Ratios
17.5.
Catalysts
17.6.
Accelerators
18.
Epoxy Curing Process
18.1.
Characterization of Epoxy Curing and Cured Networks
19.
Formulation Modifiers
19.1.
Diluents
19.2.
Thixotropic Agents
19.3.
Fillers
19.4.
Epoxy Nanocomposites
19.5.
Toughening Agents and Flexiblizers
20.
Coatings Applications
20.1.
Coatings Application Technologies
20.1.1.
Low Solids Solventborne Coatings
20.1.2.
Epoxy resins are reactive intermediates used to produce a versatile class of thermosetting polymers. They are characterized by the presence of a three‐membered cyclic ether group commonly referred to as an epoxy group, 1,2‐epoxide, or oxirane. The most widely used epoxy resins are diglycidyl ethers of bisphenol A derived from bisphenol A and epichlorohydrin. The outstanding performance characteristics of the thermosets derived from bisphenol A epoxies are largely conveyed by the bisphenol A moiety (toughness, rigidity, and elevated temperature performance), the ether linkages (chemical resistance), and the hydroxyl and epoxy groups (adhesive agents). In addition to bisphenol A, other starting materials such as aliphatic glycols and both phenol and
o
‐cresol novolacs are used to produce specialty resins. Epoxy resins may also include epoxide‐bearing compounds based on aromatic amine, triazine, and cycloaliphatic backbones.
A variety of reagents have been described for converting the liquid and solid epoxy resins to the cured state, which is necessary for the development of the ultimate end‐use properties. The curing agents or hardeners are categorized as either catalytic or coreactive. Catalytic curing agents initiate resin homopolymerization, either cationic or anionic, as a consequence of using a Lewis acid or base in the curing process. Coreactive curing agents are polyfunctional compounds typically possessing active hydrogens that are employed up to stoichiometric quantities with epoxy resins. The important classes of coreactive curing agents include multifunctional amines and their amide derivatives, polyphenols, polymeric thiols, polycarboxylic acids, anhydrides, phenol–formaldehyde novolacs and resoles, and amino–formaldehyde resins.
The largest single use of epoxy resins is in the protective coatings market where high corrosion resistance and adhesion to substrates are important. Epoxies have gained wide acceptance in protective coatings and in electrical and structural applications because of their exceptional combination of properties such as toughness, adhesion, chemical and thermal resistance, and good electrical properties.
The article contains sections titled:
1.
Introduction
2.
History
3.
Industry Overview
4.
Classes of Epoxy Resins and Manufacturing Processes
5.
Liquid Epoxy Resins (DGEBA)
5.1.
Caustic Coupling Process
5.2.
Phase‐Transfer Catalyst Process
6.
Solid Epoxy Resins Based on DGEBA
6.1.
SER Continuous Advancement Process
6.2.
Phenoxy Resins
6.3.
Epoxy‐Based Thermoplastics
7.
Halogenated Epoxy Resins
7.1.
Brominated Bisphenol A Based Epoxy Resins
7.2.
Fluorinated Epoxy Resins
8.
Multifunctional Epoxy Resins
8.1.
Epoxy Novolac Resins
8.1.1.
Bisphenol F Epoxy Resin
8.1.2.
Cresol Epoxy Novolacs
8.1.3.
Glycidyl Ethers of Hydrocarbon Epoxy Novolacs
8.1.4.
Bisphenol A Epoxy Novolacs
8.2.
Other Polynuclear Phenol Glycidyl Ether Derived Resins
8.2.1.
Glycidyl Ether of Tetrakis(4‐hydroxyphenyl)ethane
8.2.2.
Trisphenol Epoxy Novolacs
8.3.
Aromatic Glycidyl Amine Resins
8.3.1.
Triglycidyl Ether of
p
‐Aminophenol
8.3.2.
Tetraglycidyl Methylenedianiline (MDA)
9.
Specialty Epoxy Resins
9.1.
Crystalline Epoxy Resins Development
9.2.
Weatherable Epoxy Resins
9.2.1.
Hydrogenated DGEBA
9.2.2.
Heterocyclic Glycidyl Imides and Amides
9.2.3.
Hydantoin‐Based Epoxy Resins
9.3.
Elastomer‐Modified Epoxies
10.
Monofunctional Glycidyl Ethers and Aliphatic Glycidyl Ethers
11.
Cycloaliphatic Epoxy Resins and Epoxidized Vegetable Oils
12.
Epoxy Esters and Derivatives
12.1.
Epoxy Esters
12.2.
Glycidyl Esters
12.3.
Epoxy Acrylates
12.4.
Epoxy Vinyl Esters
12.5.
Epoxy Phosphate Esters
13.
Characterization of Uncured Epoxies
14.
Curing of Epoxy Resins
15.
Coreactive Curing Agents
15.1.
Amine Functional Curing Agents
15.1.1.
Primary and Secondary Amines
15.1.1.1.
Aliphatic Amines
15.1.1.1.1.
Ketimines
15.1.1.1.2.
Mannich Base Adducts
15.1.1.1.3.
Polyetheramines
15.1.1.2.
Cycloaliphatic Amines
15.1.1.3.
Aromatic Amines
15.1.1.4.
Arylyl Amines
15.1.2.
Polyamides
15.1.3.
Amidoamines
15.1.4.
Dicyandiamide
15.2.
Carboxylic Functional Polyester and Anhydride Curing Agents
15.2.1.
Carboxylic Functional Polyesters
15.2.2.
Acid Anhydrides
15.3.
Phenolic‐Terminated Curing Agents
15.4.
Melamine‐, Urea‐, and Phenol‐Formaldehyde Resins
15.5.
Mercaptans (Polysulfides and Polymercaptans) Curing Agents
15.6.
Cyclic Amidines Curing Agents
15.7.
Isocyanate Curing Agents
15.8.
Cyanate Ester Curing Agents
16.
Catalytic Cure
16.1.
Lewis Bases
16.2.
Lewis Acids
16.3.
Photoinitiated Cationic Cure
17.
Formulation Development With Epoxy Resins
17.1.
Relationship Between Cured Epoxy Resin Structure and Properties
17.2.
Selection of Epoxy Resins
17.3.
Selection of Curing Agents
17.4.
Epoxy/Curing Agent Stoichiometric Ratios
17.5.
Catalysts
17.6.
Accelerators
18.
Epoxy Curing Process
18.1.
Characterization of Epoxy Curing and Cured Networks
19.
Formulation Modifiers
19.1.
Diluents
19.2.
Thixotropic Agents
19.3.
Fillers
19.4.
Epoxy Nanocomposites
19.5.
Toughening Agents and Flexiblizers
20.
Coatings Applications
20.1.
Coatings Application Technologies
20.1.1.
Low Solids Solventborne Coatings
20.1.2.
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