1,3-BAC

Last updated
1,3-BAC
1,3-bis(aminomethyl)cyclohexane.svg
Names
Preferred IUPAC name
1,1-(Cyclohexane-1,3-diyl)di(methanamine)
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.018.129 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-941-5
PubChem CID
UNII
  • InChI=1S/C8H18N2/c9-5-7-2-1-3-8(4-7)6-10/h7-8H,1-6,9-10H2/t7-,8+
    Key: QLBRROYTTDFLDX-OCAPTIKFSA-N
  • C1CC(CC(C1)CN)CN
Properties
C8H18N2
Molar mass 142.246 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H312, H314, H317, H332, H412
P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-BAC (1,3-bis(aminomethyl)cyclohexane) is an organic molecule belonging to the sub class cycloaliphatic amine. It has the CAS Registry Number of 2579-20-6. [1] Its key use is as an epoxy resin curing agent.

Contents

Manufacture

It has been produced commercially as part of a mixture with the 1,4 derivative. [2] The primary route of manufacture is by catalytic hydrogenation of m-xylylenediamine usually called MXDA.

Uses

Like most amines it maybe used as an epoxy curing agent. However, the presence of the amino group also means it can be used in polyurethane chemistry by reacting with isocyanates. In this case a polyurea would be produced. It may also be reacted with phosgene (phosgenation) to produce an isocyanate.

Safety

It is corrosive with a Packing Group I designation.

See also

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Polyurethane</span> Polymer composed of a chain of organic units joined by carbamate (urethane) links

Polyurethane refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from a wide range of starting materials. This chemical variety produces polyurethanes with different chemical structures leading to many different applications. These include rigid and flexible foams, and coatings, adhesives, electrical potting compounds, and fibers such as spandex and polyurethane laminate (PUL). Foams are the largest application accounting for 67% of all polyurethane produced in 2016.

<span class="mw-page-title-main">Methyl isocyanate</span> Chemical compound

Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane and methyl carbylamine. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As an extremely toxic and irritating compound, it is very hazardous to human health. It was the principal toxicant involved in the infamous Bhopal gas disaster, which officially killed around 20,000 people in total. It is also a very potent lachrymatory agent

<span class="mw-page-title-main">Epoxy</span> Type of material

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 collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening ("curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure, or mixing with a catalyst. Heat is not necessarily applied externally, but is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

<span class="mw-page-title-main">Polyurea</span> Class of elastomers

Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate component and an amine component. The isocyanate can be aromatic or aliphatic in nature. It can be monomer, polymer, or any variant reaction of isocyanates, quasi-prepolymer or a prepolymer. The prepolymer, or quasi-prepolymer, can be made of an amine-terminated polymer resin, or a hydroxyl-terminated polymer resin.

<span class="mw-page-title-main">Powder coating</span> Type of coating applied as a free-flowing, dry powder

Powder coating is a type of coating that is applied as a free-flowing, dry powder. Unlike conventional liquid paint which is delivered via an evaporating solvent, powder coating is typically applied electrostatically and then cured under heat or with ultraviolet light. The powder may be a thermoplastic or a thermoset polymer. It is usually used to create a hard finish that is tougher than conventional paint. Powder coating is mainly used for coating of metals, such as household appliances, aluminium extrusions, drum hardware, automobiles, and bicycle frames. Advancements in powder coating technology like UV curable powder coatings allow for other materials such as plastics, composites, carbon fiber, and MDF to be powder coated due to the minimum heat and oven dwell time required to process these components.

<span class="mw-page-title-main">Aminoethylpiperazine</span> Chemical compound

Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.

Polyaspartic ester chemistry was first introduced in the early 1990s making it a relatively new technology. The patents were issued to Bayer in Germany and Miles Corporation in the United States. It utilizes the aza-Michael addition reaction. These products are then used in coatings, adhesives, sealants and elastomers. Pure polyurea reacts extremely quickly making them almost unusable without plural component spray equipment. Polyaspartic technology utilizes a partially blocked amine to react more slowly with the isocyanates and thus produce a modified polyurea. The amine/diamine or even triamine functional coreactant for aliphatic polyisocyanate is typically reacted with a maleate. Polyaspartic esters (PAE) initially found use in conventional solvent-borne two-component polyurethane coatings.

<span class="mw-page-title-main">3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate</span> Chemical compound

3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate (ECC) is a cycloaliphatic epoxy resin which is used in many industrial applications. It reacts by cationic polymerization using thermolatent photoinitiators to form crosslinked insoluble thermosets. Formulations based on cycloaliphatic epoxy resins such as ECC are known to form by curing thermosets with high heat and chemical resistance and good adhesion.

<i>m</i>-Xylylenediamine Chemical compound

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.

<span class="mw-page-title-main">Ethyleneamine</span> Class of chemical compounds

Ethyleneamines are a class of amine compounds containing ethylene (-CH2CH2-) linkages between amine groups. These compounds are generally colorless, low-viscosity liquids with a fishy amine odor. They are primarily used as building block chemicals and in epoxy resin curing agent chemistry.

In materials science, a polymer matrix composite (PMC) is a composite material composed of a variety of short or continuous fibers bound together by a matrix of organic polymers. PMCs are designed to transfer loads between fibers of a matrix. Some of the advantages with PMCs include their light weight, high resistance to abrasion and corrosion, and high stiffness and strength along the direction of their reinforcements.

4,4'-Diaminodicyclohexylmethane is the name for organic compounds with the formula CH2(C6H10NH2)2. It is classified as a diamine. In the epoxy industry it is often referred to as PACM, short for para-diamino­dicyclohexyl­methane. It is used as a curing agent for epoxy resins It finds particular use in epoxy flooring. Another use is to produce diisocyanates, which are precursors to polyurethane. 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 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.

<span class="mw-page-title-main">Isophorone diamine</span> Chemical compound

Isophorone diamine (usually shortened to IPDA) is a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). It is a colorless liquid. It is a precursor to polymers and coatings.

<span class="mw-page-title-main">Tetramethylxylylene diisocyanate</span> Chemical compound

Tetramethylxylylene diisocyanate (TMXDI) is an organic compound is an organic compound with the formula C6H4(CMe2NCO)2 (Me = CH3). The molecule features two isocyanate groups. It was introduced in the 1980s by American Cyanamid. TMXDI is generally classified as an aliphatic isocyanate. Aliphatic isocyanates generally exhibit enhanced UV stability compared to their aromatic counterparts.

Tetraethylenepentamine (TEPA) is an organic compound and is in the class of chemicals known as ethyleneamines. It is a slightly viscous liquid and is not colorless but, like many amines, has a yellow color. It is soluble in most polar solvents. Diethylenetriamine (DETA), triethylenetetramine (TETA), piperazine, and aminoethylpiperazine are also usually present in commercial available TEPA.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used, it usually describes all resins which have water as the main carrying solvent. The resin could be water soluble, water reducible or water dispersed.

<span class="mw-page-title-main">1,2-Diaminocyclohexane</span> Chemical compound

1,2-Diaminocyclohexane (DACH) is an organic compound with the formula (CH2)4(CHNH2)2. It is a mixture of three stereoisomers: cis-1,2-diaminocyclohexane and both enantiomers of trans-1,2-diaminocyclohexane. The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.

Blocked isocyanates are organic compounds that have their isocyanate functionality chemically blocked to control reactivity. They are the product of an isocyanate moiety and a suitable blocking agent. It may also be a polyurethane prepolymer that is NCO terminated but this functionality has also been chemically reacted with a blocking agent. They are usually used in polyurethane applications but not always. They are extensively used in industrial applications such as coatings, sealants and adhesives.

References

  1. "1,3 BAC Product Data" (PDF).
  2. "A new cycloaliphatic amine as an epoxy curative" (PDF). Archived from the original (PDF) on 2020-08-20.