Isophorone diamine

Isophorone diamine
Names
	IUPAC name 3-(Aminomethyl)-3,5,5-trimethylcyclohexan-1-amine
	Other names Isophorondiamin; IPDA
Identifiers
CAS Number	2855-13-2 (isomeric mixture) ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1876029;
ChemSpider	16867;
ECHA InfoCard	100.018.788
EC Number	220-666-8;
PubChem CID	17857;
UNII	X5WYA841BU ;
UN number	2289
CompTox Dashboard (EPA)	DTXSID6027503 ;
	InChI InChI=1S/C10H22N2/c1-9(2)4-8(12)5-10(3,6-9)7-11/h8H,4-7,11-12H2,1-3H3 Key: RNLHGQLZWXBQNY-UHFFFAOYSA-N;
	SMILES CC1(CC(CC(C1)(C)CN)N)C;
Properties
Chemical formula	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)
Solubility in water	Very good
Refractive index (nD)	1.4880
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H312, H314, H317, H318, H412
GHS precautionary statements	P260, P261, P264, P270, P272, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, 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).
	Infobox references

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.[1]

Production

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]

Uses

IPDA is used as a precursor in the manufacture of isophorone diisocyanate by phosgenation.[2]

Like other diamines, 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.

References

Hardo Siegel, Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.CS1 maint: uses authors parameter (link)
The polyurethanes book. Randall, David, Lee, Steve, 1941-. [Everberg, Belgium]: [Huntsman Polyurethanes]. 2002. ISBN 0470850418. OCLC 50479333.CS1 maint: others (link)
Pilato, Louis A.; Michno, Michael J. (1994-11-04). Advanced Composite Materials. Springer Science & Business Media. ISBN 9783540575634.
"Cycloaliphatic Amines - Hexion.com". www.hexion.com. Retrieved 2018-08-17.

External links

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[Ullmann-1] Hardo Siegel, Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.CS1 maint: uses authors parameter (link)

[2] The polyurethanes book. Randall, David, Lee, Steve, 1941-. [Everberg, Belgium]: [Huntsman Polyurethanes]. 2002. ISBN 0470850418. OCLC 50479333.CS1 maint: others (link)

[3] Pilato, Louis A.; Michno, Michael J. (1994-11-04). Advanced Composite Materials. Springer Science & Business Media. ISBN 9783540575634.

[4] "Cycloaliphatic Amines - Hexion.com". www.hexion.com. Retrieved 2018-08-17.