Imidazolidinyl urea
Encyclopedia
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
.
to imidazolidinyl urea causing dermatitis
. Such people are often also allergic to diazolidinyl urea
.
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 :
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
+ 3 H2C=O → 
Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers.
Antimicrobial
An anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...
preservative
Preservative
A preservative is a naturally occurring or synthetically produced substance that is added to products such as foods, pharmaceuticals, paints, biological samples, wood, etc. to prevent decomposition by microbial growth or by undesirable chemical changes....
used in cosmetics
Cosmetics
Cosmetics are substances used to enhance the appearance or odor of the human body. Cosmetics include skin-care creams, lotions, powders, perfumes, lipsticks, fingernail and toe nail polish, eye and facial makeup, towelettes, permanent waves, colored contact lenses, hair colors, hair sprays and...
. It is chemically related to diazolidinyl urea
Diazolidinyl urea
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....
which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser
Formaldehyde releaser
- Antimicrobials :Formaldehyde releasers are often used as an antimicrobial preservative in cosmetics. Examples include:* Quaternium-15* Imidazolidinyl urea * Diazolidinyl urea * DMDM hydantoin...
.
Safety
Some people have a contact allergyAllergy
An Allergy is a hypersensitivity disorder of the immune system. Allergic reactions occur when a person's immune system reacts to normally harmless substances in the environment. A substance that causes a reaction is called an allergen. These reactions are acquired, predictable, and rapid...
to imidazolidinyl urea causing dermatitis
Dermatitis
-Etymology:Dermatitis derives from Greek derma "skin" + -itis "inflammation" and genetic disorder.-Terminology:There are several different types of dermatitis. The different kinds usually have in common an allergic reaction to specific allergens. The term may describe eczema, which is also called...
. Such people are often also allergic to diazolidinyl urea
Diazolidinyl urea
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....
.
Chemistry
Imidazolidinyl urea was poorly characterized until recently and still has a wrong CASChemical Abstracts Service
Chemical Abstracts is a periodical index that provides summaries and indexes of disclosures in recently published scientific documents. Approximately 8,000 journals, technical reports, dissertations, conference proceedings, and new books, in any of 50 languages, are monitored yearly, as are patent...
structure assigned to it. New data show that the hydroxymethyl
Hydroxymethyl
Hydroxymethyl in the field of chemistry, particularly in organic chemistry, is the name for a substituent with the structural formula -CH2-OH. The hydroxymethyl group consists of a methylene group connected to a hydroxy group. This makes the hydroxymethyl group an alcohol...
functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
of the imidazolidine
Imidazolidine
Imidazolidine is a heterocyclic compound formally derived by the addition of four hydrogen atoms to imidazole. The intermediate, resulting from the addition of only two hydrogen atoms is called dihydroimidazole...
ring is attached to the carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
, not the nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
atom :
| |
 |
| Correct new structure | Erroneous old structure |
Synthesis
Imidazolidinyl urea is produced by the chemical reactionChemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
of allantoin
Allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid....
and formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
in the presence of sodium hydroxide solution and heat. The reaction mixture is then neutralized
Neutralization
In chemistry, neutralization, or neutralisation is a chemical reaction in which an acid and a base react to form a salt. Water is frequently, but not necessarily, produced as well. Neutralizations with Arrhenius acids and bases always produce water:Y and X represent a monovalent cation and anion...
with hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
and evaporated
Evaporation
Evaporation is a type of vaporization of a liquid that occurs only on the surface of a liquid. The other type of vaporization is boiling, which, instead, occurs on the entire mass of the liquid....
:
2