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Diazolidinyl urea

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Diazolidinyl urea
Names
IUPAC names Correct new structure: 1,3-bis(hydroxymethyl)-1-(1,3,4-tris(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)urea
Erroneous old structure: 1-(1,3-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-1,3-bis(hydroxymethyl)urea
Other names Diazolidinylurea
Germall II
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.732 Edit this at Wikidata
EC Number
  • 278-928-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18)Key: SOROIESOUPGGFO-UHFFFAOYSA-N
  • InChI=1/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18)Key: SOROIESOUPGGFO-UHFFFAOYAO
SMILES
  • O=C1N(C(=O)C(N(C(=O)NCO)CO)N1CO)CO
Properties
Chemical formula C8H14N4O7
Molar mass 278.22 g/mol
Hazards
GHS labelling:
Pictograms Skin Sens. 1
Signal word Warning
Hazard statements H317
Precautionary statements P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Diazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to imidazolidinyl urea which is used in the same way. Diazolidinyl urea acts as a formaldehyde releaser.

It is used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben.

Commercial diazolidinyl urea is a mixture of different formaldehyde addition products including polymers.

Chemistry

Synthesis

Diazolidinyl urea is produced by the chemical reaction of allantoin and formaldehyde in the presence of sodium hydroxide solution and heat. The reaction mixture is then neutralized with hydrochloric acid and evaporated:

Allantoin + 4 H2C=O → Diazolidinyl urea

Structure

Diazolidinyl urea was poorly characterized until recently and still has a wrong CAS structure assigned to it. New data show that the hydroxymethyl functional group of the imidazolidine ring is attached to the carbon, not the nitrogen atom:

Diazolidinyl urea (correct new structure) Diazolidinyl urea (erroneous old structure)
Hoeck structure previous structure

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis. Such people are often also allergic to diazolidinyl urea.

References

  1. HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority.
  2. ^ Lehmann, Søren Vig; Hoeck, Ulla; Breinholdt, Jens; Olsen, Carl Erik; Kreilgaard, Bo (2006). "Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea". Cont. Dermat. 54 (1): 50–58. doi:10.1111/j.0105-1873.2006.00735.x. PMID 16426294..
  3. Review of toxicological data (NTP NIEHS)

External links

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