Isophorone diamine (usually shortened to IPDA) is 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 ...
with the formula (CH
3)
3C
6H
7(NH
2)(CH
2NH
2). It is a colorless liquid. It is a precursor to polymers and coatings.
Production
It is usually produced as a mixture of the
''cis''- and ''trans''-isomers. It is produced by
hydrocyanation
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of pr ...
of
isophorone
Isophorone is an α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precursor to polymers, it is produced on a large ...
followed by reductive amination and hydrogenation of the nitrile.
[
]
Uses
IPDA is used as a precursor in the manufacture of isophorone diisocyanate
Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% ...
by phosgenation.
Like other diamines or amines in general, it is a curing agent for 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. 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)
In materials science, advanced composite materials (ACMs) are materials that are generally characterized by unusually high strength fibres with unusually high stiffness, or modulus of elasticity characteristics, compared to other materials, whi ...
its higher cost compared to other amines is less critical as performance is the key criteria. 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. 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 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 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 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.
See also
* 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 ...
* 1,3-BAC
* MXDA
* PACM
* DCH-99
References
External links
*{{Cite web, url=https://patentimages.storage.googleapis.com/ba/99/97/9fe0d282e62410/US20120142816A1.pdf, title=US Patent Cycloaliphatic Epoxy Curing Agent, last=, first=, date=, website=, archive-url=, archive-date=, access-date=
Safety Data Sheet
BASF Product Data
Technical Data Sheet
Three Bond Epoxy article
Diamines
Cycloalkylamines