Isophorone diisocyanate

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Structural formula
Structural formula of isophorone diisocyanate
Structural formula without stereochemistry
General
Surname Isophorone diisocyanate
other names
  • 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate
  • 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane
  • IPDI
Molecular formula C 12 H 18 N 2 O 2
Brief description

colorless to yellowish liquid with a pungent odor

External identifiers / databases
CAS number
  • 4098-71-9
  • 53880-05-0 (homopolymer)
PubChem 169132
Wikidata Q415415
properties
Molar mass 222.29 g mol −1
Physical state

liquid

density

1.06 g cm −3

Melting point

−60 ° C

boiling point
  • 303.7 ° C
  • 158–159 ° C at 13 mbar
Vapor pressure

0.0004 mbar (20 ° C)

solubility

practically insoluble in water

Refractive index

1.482 (25 ° C, 589 nm)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 330-315-317-319-334-335-411
P: 260-280-284-304 + 340 + 310-342 + 311-403 + 233
MAK

0.005 ml m −3 or 0.046 mg m −3

Toxicological data

4825 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Isophorone diisocyanate is a chemical compound from the group of aliphatic isocyanates or polyisocyanates .

Extraction and presentation

Isophorone diisocyanate is obtained in a five-stage process. By condensation of acetone with a catalyst obtained isophorone , which then reacted with hydrogen cyanide to isophorone this and with ammonia and hydrogen on to isophorone diamine is reacted (isomers). A mixture of the isophorone diisocyanate isomers is formed by reaction with phosgene , which can then be separated by distillation. The commercially available product is a cis / trans mixture in a 3: 1 ratio.

Isophorone diisocyanate

properties

Isophorone diisocyanate is a colorless to yellowish liquid with a pungent odor that occurs in two isomeric forms. It decomposes slowly in water and above 260 ° C, producing nitrous gases and hydrogen cyanide . It reacts violently with amines . It has a viscosity of 13–15 mPas at 23 ° C and a pour point of −30 ° C.

use

Isophorone diisocyanate is used as a hardener in two-component paints and is contained in paints and powder coatings . It is also used to make other polyisocyanates and polyurethanes . As a non-aromatic diisocyanate , it is suitable for the production of light and UV-resistant paints.

Web links

Individual evidence

  1. a b Entry on isophorone diisocyanate. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
  2. a b c d e f g h i Entry on isophorone diisocyanate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  3. a b c data sheet IPDI ( Memento of the original from March 4, 2016 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. at iso-elektra (PDF; 300 kB). @1@ 2Template: Webachiv / IABot / www.iso-elektra.de
  4. Isophorone diisocyanate data sheet (PDF) from Merck , accessed on January 21, 2011.
  5. Entry on 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. David Randall, Steve Lee: The Polyurethanes Book . Wiley, New York 2002, ISBN 0-470-85041-8 . .
  7. Data sheet IPDI  ( page no longer available , search in web archivesInfo: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. at Bayercoatings.@1@ 2Template: Toter Link / tecci.bayer.de  
  8. Horst Stepanski: Polyurethane adhesives. Springer-Verlag, 2016, ISBN 978-3-658-12270-6 , p. 18 ( limited preview in Google book search).