4916. Imidurea

Nomenclature

CAS number: 39236-46-9
N,N″-Methylenebis[N′-[3-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]urea]; methanebis[N,N′-(5-ureido-2,4-diketotetrahydroimidazole)-N,N-dimethylol]; imidazolidinyl urea; Abiol (3V Inc.); Biopure 100 (Biophil); Germall 115 (Sutton); Sepicide CI (Seppic); Tri-Stat IU (Tri-K); Unicide U-13 (Induchem).
C11H16N8O8; mol wt 388.29.
C 34.03%, H 4.15%, N 28.86%, O 32.96%.

Description and references

Condensation product of formaldehyde and allantoin, q.q.v. Member of a family of heterocyclic substituted urea compounds with formaldehyde releasing activity. Prepn: P. A. Berke, US 3248285 (1966 to Sutton). Description, toxicity and antimicrobial activity: P. A. Berke, W. E. Rosen, Am. Perfum. Cosmet. 85, 55 (1970). Kinetics of formaldehyde release: M. Johansen, H. Bundgaard, Arch. Pharm. Chemi Sci. Ed. 9, 117 (1981). Determn in cosmetic products: G. M. Michalakis, E. F. Barry, J. Soc. Cosmet. Chem. 45, 193 (1994). Review of use and safety assessment: J. Environ. Pathol. Toxicol. 4, 133-146 (1980); of properties and preservative activity: W. E. Rosen, P. A. Berke, Cosmet. Sci. Technol. Ser. 1, 191-205 (1984).

Chemical structure

Properties

Exists as a monohydrate. White, free-flowing fine powder, dec at temps >160°. Odorless, tasteless. Non-uv absorbing. Polar, hydrophilic. Soly (g/100 g solvent): water 200; ethylene glycol 150; propylene glycol 120; glycerin 100; methanol 0.05; ethanol <0.05; sesame oil <0.05.

Use

Antimicrobial preservative in cosmetics and topical pharmaceutical preparations.