Diazolidinyl urea
Skeletal formula of diazolidinyl urea | |
Ball-and-stick model of the diazolidinyl urea molecule | |
Names | |
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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 |
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Other names
Diazolidinylurea
Germall II |
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Identifiers | |
78491-02-8 | |
ChemSpider | 56078 |
EC Number | 278-928-2 |
Jmol 3D model | Interactive image |
PubChem | 62277 |
UNII | H5RIZ3MPW4 |
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Properties | |
C8H14N4O7 | |
Molar mass | 278.22 g/mol |
Vapor pressure | {{{value}}} |
Related compounds | |
Related compounds
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Imidazolidinyl urea |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
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.[1]
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 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:[1]
Originally reported structure | Hoeck's revised structure |
Originally reported structure | Hoeck's revised structure |
Safety
Some people have a contact allergy to imidazolidinyl urea causing dermatitis.[2] Such people are often also allergic to diazolidinyl urea.
In 2005–06, it was the 14th-most-prevalent allergen in patch tests (3.7%).[3]
References
- ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Review of toxicological data (NTP NIEHS)
- ↑ 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.