Imidazolidinyl urea

Chembox new
ImageFile=Imidazolidinyl urea correct formula.png ImageFile1=Imidazolidinyl urea erroneous formula.png ImageSize=
IUPACName=Correct new structure (upper pic.):
1,1'-methylenebis{3- [1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl] urea}
Erroneous old structure (lower pic.):
1,1'-methylenebis{3- [3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl] urea}

OtherNames=Imidurea, Germall 115;"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

Section1= Chembox Identifiers
CASNo=39236-46-9
PubChem=38258
EINECS=254-372-6
SMILES= Correct: O=C1NC(N( [H] )C1(NC(NCNC(NC(N( [H] )C(N2)=O)(CO [H] )C2=O)=O)=O)CO [H] )=O
Old: C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO
Section2= Chembox Properties
Formula=C₁₁H₁₆N₈O₈
MolarMass=388.29 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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 [http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/ImidazolidinylUrea.pdf Review of toxicological data] (NTP NIEHS)] . Such people are often also allergic to diazolidinyl urea.

Chemistry

Imidazolidinyl 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 cite journal
author = Lehmann SV, Hoeck U, Breinholdt J, Olsen CE, Kreilgaard B.
year = 2006
title = Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea
journal = Contact Dermatitis
volume = 54
issue = 1
pages = 50–58
location =
pmid =16426294
doi = 10.1111/j.0105-1873.2006.00735.x
url = http://www.blackwell-synergy.com/doi/abs/10.1111/j.0105-1873.2006.00735.x] :

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

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

References