1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. Its formula is C₁₄H₂₄O₄ and the

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

name is 2-4-(oxiran-2-ylmethoxymethyl)cyclohexylmethoxymethyloxirane. It has the CAS number of 14228-73-0 and is REACH registered in Europe. An industrial chemical, a key use is in the reduction of the

viscosity Viscosity is a measure of a fluid's rate-dependent drag (physics), resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for e ...

epoxy Epoxy is the family of basic components or Curing (chemistry), cured end products of epoxy Resin, resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide fun ...

resin systems functioning as a

reactive diluent Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer ...

Synonyms

The material is known under various names which include: * 2,2'- ,4-Cyclohexanediylbis(methyleneoxymethylene)is xirane* 1,4-Bis(glycidoxymethyl)cyclohexane * 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether * 1,4-Bis 2,3-epoxypropoxy)methylyclohexane * 1,4-Bis glycidyloxy)methylyclohexane * 1,4-Cyclohexanedimethanol diglycidyl Ether

Manufacture

The manufacturing process involves reacting cyclohexanedimethanol with

epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...

, using a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

, to form a

halohydrin In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol ...

. This is followed by washing with

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

in a

dehydrochlorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halide ...

step to form the

epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

rings. The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the

Epoxy value Epoxy value derives from the Epoxy equivalent weight (EEW) or Weight Per Epoxide (WPE) and is a measure of the epoxy content of an epoxy resin or epoxy reactive diluent, or glycidyl ether. This is an important parameter as it allows determination ...

by determination of the epoxy equivalent weight.

Uses

As the molecule has oxirane functionality, a key use is reducing the viscosity of epoxy resins. These

modified epoxy resins may then be further formulated into which may then be formulated into CASE applications:

Coating A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints ...

Adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

Sealant Sealant is a substance used to block the passage of fluids through openings in materials, a type of Seal (mechanical), mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulk'' (especially if acrylic latex or ...

Elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a portmanteau of ''ela ...

s, and electronic encapsulant. The use of the diluent does affect mechanical properties and microstructure of epoxy resins. It is also used as a monomer in UV curing systems. In addition it is used to synthesize other molecules such as the acrylated version.

Toxicology

The material is classed as a skin irritant.

References

External links

Hexion difunctional epoxy diluents

Denacol epoxy diluent range

Cargill Reactive diluents

AALChem DE 204 CHDMDGE
{{DEFAULTSORT:Cyclohexanedimethanol diglycidyl ether, 1,4- Glycidyl ethers Reactive diluents Cyclohexanes