4,4'-Diaminodicyclohexylmethane is the name for

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s with the formula CH₂(C₆H₁₀NH₂)₂. It is classified as a

diamine A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of ...

. In the epoxy industry it is often referred to as PACM, short for ''para''-diaminodicyclohexylmethane. It is used as a curing agent for

epoxy resin 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 co ...

s It finds particular use in

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 ...

flooring. Another use is to produce di

isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...

s, which are precursors to

polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...

s. The mixture is a colorless solid, but typical samples are yellowish and oily. The compound is produced as a mixture of three isomers by the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

methylenedianiline 4,4′-Methylenedianiline (MDA) is an organic compound with the formula . It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes. Synthesi ...

. These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.

Uses

This diamine is mainly used to make epoxy resin curing agents for CASE (

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 ...

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 (E) and high failure strain compared with other materials. The term, a portmanteau of ''ela ...

s) applications especially flooring. Another application arises from its reaction with phosgene to produce a cycloaliphatic diisocyanate

Hydrogenated MDI Hydrogenated MDI (H12MDI or 4,4′-diisocyanato dicyclohexylmethane) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is a water white liquid at room temperature and is manufactured in ...

, which is used to produce light stable

s. The substance may also be used as a chemical intermediate to make other molecules. 4,4'-Diaminodicyclohexylmethane was used in producing a polyamide called

Qiana Qiana ( ) is a silky nylon fiber developed in 1962 at the DuPont Experimental Station by Stanley Brooke Speck. The fiber was named Qiana when introduced by DuPont in 1968. Initially intended for high-end fashions, it became a popular material in th ...

, since discontinued. For this application, the condensation partner was dodecanoic acid.

Safety

It is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the is low. It does not exhibit mutagenic properties.

References

{{DEFAULTSORT:Diaminodicyclohexylmethane, 4,4- Diamines Cyclohexylamines

Uses

Safety

See also

References