Diazolidinyl urea is an
antimicrobial
An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
preservative
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...
used in
cosmetics
Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect ...
. It is chemically related to
imidazolidinyl 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 aller ...
which is used in the same way. Diazolidinyl urea acts as a
formaldehyde releaser
A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these ...
.
It is used in many
cosmetics
Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect ...
,
skin care
Skin care is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appea ...
products,
shampoo
Shampoo () is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the ...
s 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.
Chemistry
Synthesis
Diazolidinyl urea is produced by the
chemical reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...
of
allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacter ...
and
formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
in the presence of
sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly caustic base and alkali ...
solution and heat. The reaction mixture is then
neutralized with
hydrochloric acid
Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid
Acid strength is the tendency of an acid, symbol ...
and
evaporated
Evaporation is a type of vaporization that occurs on the surface of a liquid as it changes into the gas phase. High concentration of the evaporating substance in the surrounding gas significantly slows down evaporation, such as when humidi ...
:
![Allantoin](https://upload.wikimedia.org/wikipedia/commons/1/1c/Allantoin.svg)
+ 4 H
2C=O →
Structure
Diazolidinyl urea was poorly characterized until recently and the single
Chemical Abstracts Service
CAS (formerly Chemical Abstracts Service) is a division of the American Chemical Society. It is a source of chemical information. CAS is located in Columbus, Ohio, United States.
Print periodicals
''Chemical Abstracts'' is a periodical index tha ...
structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that one of the
hydroxymethyl
The hydroxymethyl group is the name for a substituent with the structural formula −CH2−OH. It consists of a methylene bridge (−CH2− unit) bonded to a hydroxyl group (−OH). This makes the hydroxymethyl group an alcohol. It has the identic ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s of the
imidazolidine
Imidazolidine is a heterocyclic compound (CH2)2(NH)2CH2. The parent imidazolidine is lightly studied, but related compounds substituted on one or both nitrogen centers are more common. Generally, they are colorless, polar, basic compounds. Imida ...
ring is attached to the
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
, rather than on the urea
nitrogen
Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
atom:
Safety
Some people have a contact
allergy
Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic derma ...
to
imidazolidinyl 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 aller ...
causing
dermatitis
Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can v ...
.
[Review of toxicological data](_blank)
(NTP NIEHS) Such people are often also allergic to diazolidinyl urea.
In addition to being an allergen, it is a formaldehyde releaser, meaning it releases the carcinogen formaldehyde slowly as it degrades
In 2005–06, it was the 14th-most-prevalent
allergen
An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies.
In technical terms ...
in
patch tests (3.7%).
[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.]
References
{{DEFAULTSORT:Diazolidinyl Urea
Preservatives
Disinfectants
Ureas
Hydantoins