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Imidazolidinyl urea

1,1′-methylenebis{3-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} Erroneous old structure (lower pic.): 1,1′-methylenebis{3-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} N′,N″-methylenebis[3-[1-(hydroxymethyl)- 2,5-dioxoimidazolidin-4-yl]urea];

1-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]- 3-[[[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl] carbamoylamino]methyl]urea Imidazolidinyl urea is an antimicrobial preservative used in cosmetics . It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.

Safety

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

Chemistry

Imidazolidinyl 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 the hydroxymethyl functional group of each imidazolidine ring is attached to the carbon, rather than on the nitrogen atom:{{cite journal

:{| |- align="center" valign="middle" | [[Image:Imidazolidinyl urea erroneous formula.png|200px|Originally reported structure]] | [[Image:Imidazolidinyl urea correct formula.png|200px|Hoeck's revised structure]] |- align="center" | Originally reported structure | Hoeck's revised structure |}

Synthesis

Imidazolidinyl 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:

:2 [[File:Allantoin.svg|150px|Allantoin]] + 3 H2C=O → [[File:Imidazolidinyl urea correct formula.png|200px|Imidazolidinyl urea]]

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

References

[https://web.archive.org/web/20131107214747/http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPDF/ImidazolidinylUrea_508.pdf Review of toxicological data] (NTP NIEHS)

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

preservatives disinfectants ureas hydantoins formaldehyde-releasers

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