Diazolidinyl urea

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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 YesY
ChemSpider 56078 YesY
EC Number 278-928-2
Jmol 3D model Interactive image
PubChem 62277
UNII H5RIZ3MPW4 YesY
Properties
C8H14N4O7
Molar mass 278.22 g/mol
HazardsSkin Sens. 1[1]
GHS signal word WARNING
H317
P261, P272, P280, P302+352, P333+313, P321, P363, P501
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
Related compounds
Related compounds
Imidazolidinyl urea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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[edit]

Synthesis[edit]

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[edit]

Diazolidinyl urea was poorly characterized until recently and the single Chemical Abstracts Service structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that one of the hydroxymethyl functional groups of the imidazolidine ring is attached to the carbon, rather than on the urea nitrogen atom:[2]

Originally reported structure Hoeck's revised structure
Originally reported structure Hoeck's revised structure

Safety[edit]

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

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

References[edit]

  1. ^ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, 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)
  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.