4,4'-Diaminodicyclohexylmethane is the name for

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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

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

. 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 coll ...

s It finds particular use in

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 ...

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) refers to 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, polyurethan ...

. 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 Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...

of methylenedianiline. 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, 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) 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 t ...

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

dodecanoic acid Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids. It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and es ...

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

Uses

Safety

See also

References