2-Methylpentamethylenediamine

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.[1]

2-Methylpentamethylenediamine

2-Methylpentamethylenediamine line structure
Names
Preferred IUPAC name
2-Methylpentane-1,5-diamine
Other names
1,5-Diamino-2-methylpentane, 2-Methylpentanediamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.035.945
EC Number
  • 239-556-6
UNII
  • InChI=1S/C6H16N2/c1-6(5-8)3-2-4-7/h6H,2-5,7-8H2,1H3
    Key: JZUHIOJYCPIVLQ-UHFFFAOYSA-N
  • CC(CCCN)CN
Properties
C6H16N2
Molar mass 116.208 g·mol−1
Appearance colorless liquid
Boiling point 192 °C (378 °F; 465 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant, Corrosive, Acute Toxic
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H302, H312, H314, H331, H332, H335
P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P363, P403+P233, P405, P501
Flash point 83
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

2-Methylpentamethylenediamine can serve as a curing agent for epoxy resin systems. It gives good adhesion to metals and resistance against corrosion and other chemicals. It provides toughness, low blush, uniform finish, high gloss, and improves UV stability. It reduces gel time and is compatible with epoxy resins. It is suitable for marine, industrial, and decorative coatings. It is better known by the trade name "Dytek A".[2]

2-Methylpentamethylenediamine can also be used as a chain extender for polyurethane applications, and in particular with PUDs.[3][4] Its derivatives like aspartic esters, secondary amines, aldimines and ketoimines serve as curatives in polyurea systems. In polyamides, 2-Methylpentamethylenediamine acts as a crystallinity disruptor. This makes polymers amorphous in structure and slows down crystallization. It lowers melting point, improves surface appearance, increases abrasion resistance, and dye uptake. It also reduces water absorption, gelling, melt and quench temperatures.[5]

In summary, its uses are:[6]

  • Corrosion inhibitor
  • Polyamide adhesive and ink resins.
  • Polyamide films, plastics, and fibers
  • Epoxy curing agents
  • Metalworking Fluids
  • Chain extenders
  • Water treatment chemicals
  • Isocyanates

Hazards

2-Methylpentamethylenediamine has many uses, but is a hazardous chemical.[7] It can cause burns, is corrosive to skin, harmful when swallowed, and it can cause pulmonary edema and acute pneumonitis when inhaled in high concentrations.[8]

See also

References
  1. Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (15 June 2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_001. ISBN 3527306730.
  2. "Dytek® A (2-Methylpentamethylenediamine) - INVISTA - datasheet". coatings.specialchem.com. Retrieved 2021-04-07.
  3. Howarth, GA (2003-06-01). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 111–118. doi:10.1007/BF02699621. ISSN 1476-4865. S2CID 93574741.
  4. Madbouly, Samy A.; Otaigbe, Joshua U.; Nanda, Ajaya K.; Wicks, Douglas A. (2005-05-01). "Rheological Behavior of Aqueous Polyurethane Dispersions: Effects of Solid Content, Degree of Neutralization, Chain Extension, and Temperature". Macromolecules. 38 (9): 4014–4023. doi:10.1021/ma050453u. ISSN 0024-9297.
  5. "Dytek A (2-Methylpentamethylenediamine) - Invista Specialty Chemicals". polymer-additives.specialchem.com. Retrieved 2021-04-07.
  6. "Dytek® A | 2-Methylpentamethylenediamine (MPMD)". Dytek. Retrieved 2021-04-07.
  7. PubChem. "1,5-Pentanediamine, 2-methyl-". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-05.
  8. "2-Methylpentamethylenediamine - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 2021-04-07.
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