Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C₁₁H₂₀O₄ and the CAS registry number of 17557-23-2. It has two oxirane groups per molecule. Its principle use is in modifying

epoxy Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also coll ...

resins. It is REACH registered. The IUPAC name is 2- 2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxyethyl]oxirane.

Synthesis

Neopentyl glycol Neopentyl glycol (IUPAC name: 2,2-dimethylpropane-1,3-diol) is an organic chemical compound. It is used in the synthesis of polyesters, paints, lubricants, and plasticizers. When used in the manufacture of polyesters, it enhances the stability of ...

and

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 miscible with most polar organi ...

are reacted in the presence of 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 sp ...

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

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 NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

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 hali ...

step. This forms Neopentyl glycol diglycidyl ether. 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 is the family of basic components or Curing (chemistry), cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional ...

by determination of the epoxy equivalent weight.

Uses

A key use is modifying the viscosity and properties of epoxy resins. As an

Epoxy Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also coll ...

modifier it is classed as an epoxy

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 plasticize ...

. which may then be formulated into CASE applications:

Coating A coating is a covering that is applied to the surface of an object, usually referred to as the Substrate (materials science), substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquid ...

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 advant ...

Sealant Sealant is a substance used to block the passage of fluids through openings in materials, a type of mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulking'' and also serve the purposes of blocking dust, s ...

s and

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

s and

composite material A composite material (also called a composition material or shortened to composite, which is the common name) is a material which is produced from two or more constituent materials. These constituent materials have notably dissimilar chemical or ...

s. These uses include cationic polymerization reactions. The use of the diluent does effect mechanical properties and microstructure of epoxy resins. It is also used to synthesize other molecules.

Toxicity

NPGDGE toxicity is fairly well understood. It is classed as a skin irritant and skin sensitizer.

References

External links

Hexion difunctional epoxy diluents

Denacol epoxy diluent range

Aalchem NPGDGE

Cargill Reactive diluents
{{Glycidyl ethers Glycidyl ethers Reactive diluents

Synthesis

Uses

Toxicity

See also

References

Further reading

External links