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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.

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.

Preparation

2-Imidazolidinone can be obtained by the direct condensation of ethylenediamine with urea or dimethyl carbonate:

C<sub>2</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub> + CO(NH<sub>2</sub>)<sub>2</sub> → C<sub>3</sub>H<sub>6</sub>N<sub>2</sub>O + 2 NH<sub>3</sub>
H<sub>2</sub>N–CH<sub>2</sub>–CH<sub>2</sub>–NH<sub>2</sub> + (MeO)<sub>2</sub>CO → C<sub>3</sub>H<sub>6</sub>N<sub>2</sub>O + 2 MeOH

It can also be obtained by the direct condensation of ethylene glycol and urea:

CO(NH<sub>2</sub>)<sub>2</sub> + HO–CH<sub>2</sub>–CH<sub>2</sub>–OH → C<sub>3</sub>H<sub>6</sub>N<sub>2</sub>O + 2 H<sub>2</sub>O

References