Chemistry:4,4-Diaminodicyclohexylmethane
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| Names | |
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| Preferred IUPAC name
4,4'-Methylenedi(cyclohexan-1-amine) | |
| Other names
4,4'-Methylenebis(cyclohexan-1-amine)
Methylene bis(4,4'-cyclohexylamine) Bis(4-aminocyclohexyl)methane | |
| Identifiers | |
3D model (JSmol)
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| Properties | |
| C13H26N2 | |
| Molar mass | 210.365 g·mol−1 |
| Appearance | colorless solid |
| Melting point | 60–65 °C (140–149 °F; 333–338 K) |
| Boiling point | 330–331 °C (626–628 °F; 603–604 K) |
| Hazards | |
| GHS pictograms |     
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| GHS Signal word | Danger |
| H302, H314, H317 | |
| P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P314, P320, P321, P330, P333+313, P363, P391, P403+233 | |
| Flash point | 153.5 °C (308.3 °F; 426.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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[1] It finds particular use in epoxy flooring.[2] 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.[3] These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.[4]
Uses
The main use of the product is to make epoxy resin curing agents for CASE (Coatings, Adhesives, Sealants, and Elastomers) applications especially flooring. Another key use is to react with phosgene to produce a cycloaliphatic diisocyanate Hydrogenated MDI which is used to produce light stable polyurethanes.
Safety
It is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the -1">50 is low. It does not exhibit mutagenic properties.
See also
References
- ↑ "Products & Applications: VESTAMIN® IPD, VESTAMIN® TMD, VESTAMIN® PACM". Evonik. https://coatings.evonik.com/product/coatings/downloads/vestamin-en.pdf.
- ↑ "A New Epoxy Curing Agent with Long Pot Life and Fast Cure" (in en). https://www.pcimag.com/articles/96269-a-new-epoxy-curing-agent-with-long-pot-life-and-fast-cure?v=preview.
- ↑ Karsten Eller; Erhard Henkes; Roland Rossbacher; Hartmut Höke (2005). "Amines, Aliphatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
- ↑ Barkdoll, A. E.; Gray, H. W.; Kirk, W., Jr. (1951). "Alicyclic diamines: the geometric isomers of bis(4-aminocyclohexyl)methane". Journal of the American Chemical Society 73 (2): 741–6. doi:10.1021/ja01146a071.
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