Diazolidinyl urea is an

antimicrobial An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth (bacteriostatic agent). Antimicrobial medicines can be grouped according to the microorganisms they are used to treat. For example, antibiotics are used aga ...

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 ...

used in

cosmetics Cosmetics are substances that are intended for application to the body for cleansing, beautifying, promoting attractiveness, or altering appearance. They are mixtures of chemical compounds derived from either Natural product, natural source ...

. 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 alle ...

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

skin care Skin care or skincare is the practice of maintaining and improving the health and appearance of the skin. It includes washing, moisturizing, protecting from the sun, and treating skin problems like acne and dryness. Skin care can help prevent i ...

products,

shampoo Shampoo () is a hair care product, typically in the form of a viscous liquid, that is formulated to be used for cleaning (scalp) hair. Less commonly, it is available in solid bar format. (" Dry shampoo" is a separate product.) Shampoo is use ...

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 chemistry, chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an Gibbs free energy, ...

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 an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

in the presence of

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

solution and heat. The reaction mixture is then neutralized with

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

and evaporated: : Allantoin

+ 4 H₂C=O →

Structure

Diazolidinyl urea was poorly characterized until recently and the single

Chemical Abstracts Service Chemical Abstracts Service (CAS) is a division of the American Chemical Society. It is a source of chemical information and is located in Columbus, Ohio, United States. Print periodicals ''Chemical Abstracts'' is a periodical index that provid ...

structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that one of the hydroxymethyl

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

s of the imidazolidine ring is attached to the

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

, rather than on the urea

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atom: :

Safety

Some people have a contact

allergy Allergies, also known as allergic diseases, are various conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include Allergic rhinitis, hay fever, Food allergy, food al ...

causing

dermatitis Dermatitis is a term used for different types of skin inflammation, 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 ...

.Review of toxicological data
(NTP NIEHS) Such people are often also allergic to diazolidinyl urea. In addition to being an allergen, it is a

releaser, since it generates formaldehyde slowly as it degrades. Although the formaldehyde acts as a bactericidal preservative, it is a known carcinogen. In 2005–06, it was the 14th-most-prevalent

allergen An allergen is an otherwise harmless substance that triggers an allergic reaction in sensitive individuals by stimulating an immune response. In technical terms, an allergen is an antigen that is capable of stimulating a type-I hypersensitivi ...

patch test A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin. Patch testing helps identify which substances may be causing a delayed-type allergic reaction in a patient and ...

s (3.7%).

References

{{DEFAULTSORT:Diazolidinyl Urea Preservatives Disinfectants Ureas Hydantoins