Chemistry:2-Imidazolidinone
2-Imidazolidinone (imidazolidin-2-one) is a cyclic urea derivative. It is used as an intermediate in organic synthesis and as a building block for substituted imidazolidinones.[1]
Uses
2-Imidazolidinone is principally used as a formaldehyde scavenger in amino-resin systems and textile finishes. It reacts with free formaldehyde and with pendant N-methylol groups to form stable adducts, lowering free formaldehyde content and emissions. Applications include incorporation as an internal additive in urea-formaldehyde adhesives or as a post-treatment in textile finishing baths and on wood-based panels. Reported usage levels vary by application, commonly around 5–10% by weight relative to resin solids for internal scavenging, and 10–40% in commercial aqueous scavenger concentrates for surface or post-treatment applications. Careful optimization of resin formulation and curing is necessary to avoid adverse effects on bonding strength and cure behavior.[2][3][4]
Preparation
2-Imidazolidinone can be obtained by the direct condensation of ethylenediamine with urea or dimethyl carbonate:[5]
- C2H4(NH2)2 + CO(NH2)2 → C3H6N2O + 2 NH3
- H2N–CH2–CH2–NH2 + (MeO)2CO → C3H6N2O + 2 MeOH
It can also be obtained by the direct condensation of ethylene glycol and urea:[6][7][8]
- CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O
References
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedPubChem - ↑ CN1739821A - Ethylene urea amino derivative formaldehyde scavenger. https://patents.google.com/patent/CN1739821A/en
- ↑ WO2012029787 - Formaldehyde scavenger; WIPO. https://patentscope.wipo.int
- ↑ Wang X., 'The Removal of Formaldehyde from Urea Adhesives', Polymers 2024.
- ↑ Patent / process literature for DMC route.
- ↑ US2526757A - Preparation of ethyleneurea. https://patents.google.com/patent/US2526757A/en
- ↑ US2416046A - Process for the preparation of ethyleneurea. https://patents.google.com/patent/US2416046A/en
- ↑ Schweitzer, C.E., J. Org. Chem. 1950.
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