4,4'-Diaminodicyclohexylmethane Explained

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 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.[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]

Notes and References

  1. Web site: Products & Applications: VESTAMIN® IPD, VESTAMIN® TMD, VESTAMIN® PACM . Evonik . January 15, 2019 .
  2. Web site: A New Epoxy Curing Agent with Long Pot Life and Fast Cure. 2021-05-18. www.pcimag.com. en.
  3. Encyclopedia: Karsten Eller. Erhard Henkes. Roland Rossbacher. Hartmut Höke. Amines, Aliphatic. Ullmann’s Encyclopedia of Industrial Chemistry. 2005. Wiley-VCH. Weinheim. 10.1002/14356007.a02_001. 3527306730 .
  4. Huang . Yizhou . Tian . Yazhou . Li . Yuanyuan . Tan . Xiaocun . Li . Qing . Cheng . Jue . Zhang . Junying . 2017-10-16 . High mechanical properties of epoxy networks with dangling chains and tunable microphase separation structure . RSC Advances . en . 7 . 77 . 49074–49082 . 10.1039/C7RA08886H . 2046-2069. free .
  5. Gawdzik . Barbara . Kovtun . Oksana . 2005-12-15 . Synthesis of glycidyl amine adducts and their copolymerization with glycidyl methacrylate . Journal of Applied Polymer Science . en . 98 . 6 . 2461–2466 . 10.1002/app.22444 . 0021-8995.
  6. Book: 10.1002/14356007.a10_567.pub2. Fibers, 4. Polyamide Fibers . Ullmann's Encyclopedia of Industrial Chemistry . 2011 . Estes . Leland L. . Schweizer . Michael . 978-3527306732 .
  7. Web site: PubChem . 4,4'-Methylenedicyclohexanamine . 2022-12-05 . pubchem.ncbi.nlm.nih.gov . en.
  8. Alicyclic diamines: the geometric isomers of bis(4-aminocyclohexyl)methane. Barkdoll, A. E.. Gray, H. W.. Kirk, W., Jr.|journal=Journal of the American Chemical Society|year=1951|volume=73|issue=2 |pages=741–6|doi=10.1021/ja01146a071}}

    Uses

    This diamine is mainly used to make epoxy resin curing agents for CASE (Coatings, Adhesives, Sealants, and Elastomers) applications especially flooring.[4] Another application arises from its reaction with phosgene to produce a cycloaliphatic diisocyanate Hydrogenated MDI, which is used to produce light stable polyurethanes. The substance may also be used as a chemical intermediate to make other molecules.[5]

    4,4'-Diaminodicyclohexylmethane was used in producing a polyamide called Qiana, since discontinued. For this application, the condensation partner was dodecanoic acid.[6]

    Safety

    It is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the is low. It does not exhibit mutagenic properties.[7]

    See also

    References

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