Diazolidinyl urea

Diazolidinyl urea
IUPAC name 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	78491-02-8 Y
PubChem	62277
ChemSpider	56078 Y
UNII	H5RIZ3MPW4 Y
EC number	278-928-2
Jmol-3D images	Image 1
SMILES O=C1N(C(=O)C(N(C(=O)NCO)CO)N1CO)CO
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) Y Key: SOROIESOUPGGFO-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C8H14N4O7
Molar mass	278.22 g/mol
Hazards[1]
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H317
GHS precautionary statements	P261, P272, P280, P302+352, P333+313, P321, P363, P501
EU Index	not listed
Related compounds
Related compounds	Imidazolidinyl urea
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[2]

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:

+ 4 H₂C=O →

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:^[2]

Hoeck structure	previous structure

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis.^[3] Such people are often also allergic to diazolidinyl urea.

References

1. ^ HSNO Chemical Classification Information Database (New Zealand Environmental Risk Management Authority), http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=4706, retrieved 2009-09-06 .
2. ^ ^{a b} 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

• "Diazolidinyl urea". MEKOS Laboratories AS. http://www.orion-health.co.nz/Info%20Cards/Diazolidinyl%20Urea.htm. Retrieved 2007-03-11.