4831. 1-(Hydroxymethyl)-5,5-dimethylhydantoin

Nomenclature

CAS number: 116-25-6
1-(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione; monomethyloldimethylhydantoin; MDMH; methylol dimethylhydantoin.
C6H10N2O3; mol wt 158.16.
C 45.56%, H 6.37%, N 17.71%, O 30.35%.

Description and references

Prepd by treating 5,5-dimethylhydantoin with formaldehyde: Mackey, US 2762708 (1956 to GAF).

Chemical structure

Properties

Crystals, mp 100°. Freely sol in water, methanol, ethanol, acetone; slightly sol in ethyl acetate. Practically insol in ether, trichloroethylene, carbon tetrachloride.

Use

As preservative in cosmetic prepns. The compound liberates formaldehyde steadily at a very slow rate in the presence of water at pH 6. The available formaldehyde is about 19% (w/w), and 0.1-10% is usuallly mixed with the cosmetic product. When heated in the dry state MDMH forms a water-soluble dimethylhydantoin formaldehyde resin, compatible with gelatin, polyvinyl acetate, ethyl cellulose. The resin is used in hair lacquers.