Names | |
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IUPAC name 3-(Aminomethyl)-3,5,5-trimethylcyclohexan-1-amine | |
Other names Isophorondiamine; IPDA | |
Identifiers | |
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3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.018.788 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 2289 |
CompTox Dashboard (EPA) | |
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Properties | |
C10H22N2 | |
Molar mass | 170.300 g·mol−1 |
Appearance | Colourless liquid |
Density | 0.922 |
Melting point | 10 °C (50 °F; 283 K) |
Boiling point | 247 °C (477 °F; 520 K) |
Very good | |
Refractive index (nD) | 1.4880 |
Hazards | |
GHS labelling: | |
Danger | |
H302, H312, H314, H317, H412 | |
P260, P261, P264, P270, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P405, P501 | |
Flash point | 117°C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isophorone diamine (usually shortened to IPDA) is a chemical compound and specifically a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). It is a colorless liquid. It is a precursor to polymers and coatings. [1]
It is usually produced as a mixture of the cis- and trans-isomers. It is produced by hydrocyanation of isophorone followed by reductive amination and hydrogenation of the nitrile. [1]
IPDA is used as a precursor in the manufacture of isophorone diisocyanate by phosgenation. [2]
Like other diamines or amines in general, it is a curing agent for epoxy resins. When used in coatings applications the higher cost compared to other amines is justified by the enhanced UV stability and thus lower yellowing tendency. In the production of advanced composite materials (engineering) its higher cost compared to other amines is less critical as performance is the key criteria. [3] [4] Cycloaliphatic amines such as IPDA also are known to have lower yellowing tendency than other amines and are thus used in coatings applications where this feature is important for aesthetics. Although it is not the only cycloaliphatic amine used in epoxy flooring, it has the largest use by volume. [5] Other cycloaliphatic amines used in flooring include 1,3-BAC, MXDA, PACM and DCH-99.
In laboratory tests, Tokyo Metropolitan University found that IPDA was able to remove more than 99 percent of CO2 from air with a concentration of 400 parts per million (ppm) – about the level currently in the atmosphere. This process also happened much faster than other carbon capture techniques, removing 201 millimoles of CO2 per hour, per mole of the compound. That is at least twice as fast as other Direct Air Capture lab systems, and far faster than the leading artificial leaf device.
The pollutant separated out into flakes of a solid carbamic acid material, which could be removed from the liquid relatively easily. If need be, it can be converted back into gaseous CO2 by heating it to 60 °C (140 °F), which also releases the original liquid IPDA ready for reuse. Whether the carbon is kept as a solid or a gas, it can then be stored or reused in industrial or chemical processes. The research was published in the journal ACS Environmental Au. [6]
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.
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.
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, and 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.
In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO−.
Fusion bonded epoxy coating, also known as fusion-bond epoxy powder coating and commonly referred to as FBE coating, is an epoxy-based powder coating that is widely used to protect steel pipe used in pipeline construction from corrosion. It is also commonly used to protect reinforcing bars and on a wide variety of piping connections, valves etc. FBE coatings are thermoset polymer coatings. They come under the category of protective coatings in paints and coating nomenclature. The name fusion-bond epoxy is due to resigning cross-link and the application method, which is different from a conventional paint. In 2020 the market size was quoted at 12 billion dollars.
Hexamethylene diisocyanate (HDI) is the organic compound with the formula (CH2)6(NCO)2. It is classified as an diisocyanate. It is a colorless liquid. It has sometimes been called HMDI but this not usually done to avoid confusion with Hydrogenated MDI.
Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.
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.
A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.
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.
m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.
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 polyurethanes. 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.
Tetramethylxylylene diisocyanate (TMXDI) is an organic compound with the formula C6H4(CMe2NCO)2 (Me = CH3). Introduced in the 1980s by American Cyanamid, the molecule features two isocyanate groups. TMXDI is generally classified as an aliphatic isocyanate, which are generally more UV stable than their aromatic counterparts.
1,3-BAC is an organic molecule belonging to the sub class cycloaliphatic amine. It has the CAS Registry Number of 2579-20-6. Its key use is as an epoxy resin curing agent.
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.
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.
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 relatively small quantities. It is also known as 4,4'-methylenedi(cyclohexyl isocyanate) or methylene bis(4-cyclohexylisocyanate) and has the formula CH2[(C6H10)NCO]2.
2-Methylpentamethylenediamine is an organic compound part of the amine family with the formula H2NCH2CH2CH2CH(CH3)CCH2NCH2. A colorless liquid, this diamine is obtained by the hydrogenation of 2-methylglutaronitrile.
In organic chemistry, amine value is a measure of the nitrogen content of an organic molecule. Specifically, it is usually used to measure the amine content of amine functional compounds. It may be defined as the number of milligrams of potassium hydroxide (KOH) equivalent to one gram of epoxy hardener resin. The units are thus mg KOH/g.
Diethyl toluene diamine (DETDA) is a liquid aromatic organic molecule with formula C11H18N2. It is chemically an aromatic diamine and has the CAS Registry number of 68479-98-1. It has more than one isomer and the mixture of the two main isomers is given a different CAS number of 75389-89-8. It is often marketed as a less toxic version of 4,4'-methylenedianiline (MDA). It is also used to replace the more toxic 4,4'-methylenebis(2-chloroaniline) (MOCA). The toxicology is reasonably well understood.