Diazolidinyl urea

Diazolidinyl urea
Skeletal formula of diazolidinyl urea
Ball-and-stick model of the diazolidinyl urea molecule
Names
IUPAC names
Correct new structure: 1-[3,4-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1,3-bis(hydroxymethyl)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
78491-02-8 Yes
ChemSpider 56078 Yes
EC number 278-928-2
Jmol-3D images Image
PubChem 62277
UNII H5RIZ3MPW4 Yes
Properties
C8H14N4O7
Molar mass 278.22 g/mol
Hazards[1]
GHS pictograms
GHS signal word WARNING
H317
P261, P272, P280, P302+352, P333+313, P321, P363, P501
EU Index not listed
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Related compounds
Related compounds
 Imidazolidinyl urea
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
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.

Patch test

In 2005–06, it was the 14th-most-prevalent allergen in patch tests (3.7%).[4]

References

  1. ↑ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-09-06
  2. ↑ 2.0 2.1 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)
  4. ↑ Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009 May–Jun;20(3):149-60.