 | |
 | |
| Names | |
|---|---|
| IUPAC name 5-isocyanato-1- | |
| Other names IPDI | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.021.692 |
| UNII | |
| |
| |
| Properties | |
| C12H18N2O2 | |
| Molar mass | 222.3 g/mol |
| Appearance | Colourless to slightly yellow liquid[1] |
| Odor | pungent[1] |
| Density | 1.062 g/cm3 @ 20 °C, liquid |
| Melting point | −60 °C (−76 °F; 213 K) |
| Boiling point | 158 °C (316 °F; 431 K) at 1.33 kPa |
| Vapor pressure | 0.0003 mmHg (20°C)[1] |
| Hazards | |
| Flash point | 155 °C (311 °F; 428 K) (PMCC) |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | none[1] |
REL (Recommended) | TWA 0.005 ppm (0.045 mg/m3) ST 0.02 ppm (0.180 mg/m3) [skin][1] |
IDLH (Immediate danger) | N.D.[1] |
| Related compounds | |
Relatedisocyanates | Hexamethylene diisocyanate |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Isophorone diisocyanate (IPDI) is an organic compound in the class known asisocyanates. More specifically, it is analiphatic diisocyanate. It is produced in relatively small quantities, accounting for (withhexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000.[2] Aliphatic diisocyanates are used, not in the production ofpolyurethane foam, but in special applications, such as enamelcoatings which are resistant toabrasion and degradation fromultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied toaircraft.[3]
Isophorone diisocyanate (IPDI) stands out as a cycloaliphatic diisocyanate distinguished by its two reactive isocyanate groups, exhibiting differences in reactivity between primary and secondary NCO groups. This unique property ensures high selectivity in reacting with hydroxyl-bearing compounds.
This distinctive attribute proves advantageous in processinglow-viscosityprepolymers, resulting in a notably reduced residual content ofmonomeric diisocyanate. Furthermore, the low viscosity of IPDI-based prepolymers facilitates a decrease insolvent usage. The presence of methyl groups linked to the cyclohexane ring broadens IPDI's compatibility withresins and solvents.
The inherent cycloaliphatic ring confers heightened rigidity and a notably elevatedglass transition temperature to IPDI-based products. IPDI itself is a transparent, slightly yellowish, low-viscosity liquid with asolidification point at -60 °C andboiling point at 158 °C. Semi-finished products like NCO-terminated prepolymers exhibit a low tendency tocrystallize, remaining in a liquid state and facilitating easy processing.[3][4][5]
Isophorone diisocyanate is produced byphosgenation ofisophorone diamine in five-step reaction:[2]
IPDI exists in two stereoisomers, cis and trans. Their reactivities are similar. Each stereoisomer is an unsymmetrical molecule, and thus has isocyanate groups with different reactivities. The primary isocyanate group is more reactive than the secondary isocyanate group.[2]
Isophorone diisocyanate is used in special applications:[6][3][7]
Isophorone diisocyanate is a highlytoxic substance if inhaled. It can cause eye irritation and irreversible eye damage, lung and respiratory damage. It is a skin irritant and causes allergic reactions and may cause skin corrosion on prolonged contact. It is highly hazardous to aquatic environment.
H-statements: H315, H317, H319, H331, H334, H335, H411
P-statements: P260, P273, P280, P305+P351+P338, P308+P313[8][5]
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