Diazolidinyl urea

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Diazolidinyl urea
IUPAC name Correct new structure: 1,3-bis(hydroxymethyl)-1-(1,3,4-tris(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)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
CAS number [78491-02-8]
PubChem 62277
EINECS number 278-928-2
SMILES Correct: O=C1N(CO)C(N(CO)C1(N(CO)C(NCO)=O)CO[H])=O
Old: O=C(N(CO)C1N(CO)C(N(CO)C1=O)=O)NCO
Properties
Molecular formula C8H14N4O7
Molar mass 278.22
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

Contents

[edit] Uses

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.

[edit] Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis[1]. Such people are often also allergic to diazolidinyl urea.

Diazolidinyl urea, as a formaldehyde releaser, is sometimes used in cosmetic products as a preservative, was recently re-classified by the International Agency for Research on Cancer to its highest toxic class, IARC 1 (known human carcinogen). Formaldehyde is classified as a probable human carcinogen by the U.S. Environmental Protection Agency, which provides sufficient evidence that formaldehyde causes nasopharyngeal cancer in humans by the International Agency for Research on Cancer.[2]

It has been banned in Europe[citation needed], after studies concluded that effects can result in: carcinogen, causes allergic reactions and contact dermatitis; headaches; irritates mucous membranes; damaging to eyes; linked to joint and chest pain; depression; headaches; fatigue; dizziness and immune dysfunction.

Yet, other reports claim that diazolidinyl urea being banned from Europe is false it does not form formaldehyde in a gaseous state, which is the only known carcinogenic form of formaldehyde.[3]

[edit] Chemistry

[edit] 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 [4]:

Diazolidinyl urea (correct new structure) Diazolidinyl urea (erroneous old structure)
Correct new structure Erroneous old structure

[edit] 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

Commercial diazolidinyl urea is a mixture of different formaldehyde addition products including polymers[4].

[edit] References

  1. ^ Review of toxicological data (NTP NIEHS)
  2. ^ http://monographs.iarc.fr/ENG/Monographs/vol88/volume88.pdf "Formaldehyde".
  3. ^ Ecomall report on skin care
  4. ^ a b Lehmann SV, Hoeck U, Breinholdt J, Olsen CE, Kreilgaard B. (2006). "Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea". Contact Dermatitis 54 (1): 50–58. doi:10.1111/j.0105-1873.2006.00735.x. PMID 16426294. 

[edit] References