Names | |
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IUPAC names Correct new structure (upper pic.): 1,1′-methylenebis{3-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} Erroneous old structure (lower pic.): 1,1′-methylenebis{3-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} | |
Other names 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]ureaContents | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.049.411 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C11H16N8O8 | |
Molar mass | 388.29 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
This article needs additional citations for verification .(February 2010) |
Imidazolidinyl urea is an antimicrobial preservative used in cosmetics [ citation needed ]. It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.
Some people have a contact allergy to imidazolidinyl urea causing dermatitis. [1] Such people are often also allergic to diazolidinyl urea.
Imidazolidinyl urea was poorly characterized until recently and the single Chemical Abstracts Service structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that the hydroxymethyl functional group of each imidazolidine ring is attached to the carbon, rather than on the nitrogen atom: [2]
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:
Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers. [2]
Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.
Formaldehyde is a naturally occurring organic compound with the formula CH2O and structure H−CHO. The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde, hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes and one of the simplest of the carbohydrates. The common name of this substance comes from its similarity and relation to formic acid.
Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. Containing two alcohol groups, it is classed as a diol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.
Urushiol is an oily mixture of organic compounds with allergenic properties found in plants of the family Anacardiaceae, especially Toxicodendronspp., Comocladia spp. (maidenplums), Metopium spp. (poisonwood), and also in parts of the mango tree as well as the fruit of the cashew tree. In most individuals, urushiol causes an allergic skin rash on contact, known as urushiol-induced contact dermatitis.
Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are not contagious or life-threatening, but can be very uncomfortable.
Quaternium-15 is a quaternary ammonium salt that has been used as a surfactant and preservative. It acts as an antimicrobial agent because it slowly releases formaldehyde, which is a preservative with biocidal properties.
Urea-formaldehyde (UF), also known as urea-methanal, so named for its common synthesis pathway and overall structure, is a nontransparent thermosetting resin or polymer. It is produced from urea and formaldehyde. These resins are used in adhesives, plywood, particle board, medium-density fibreboard (MDF), and molded objects. In agriculture, urea-formaldehyde compounds are one of the most commonly used types of slow-release fertilizer.
Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.
Bronopol is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.
A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
Allergic contact dermatitis (ACD) is a form of contact dermatitis that is the manifestation of an allergic response caused by contact with a substance; the other type being irritant contact dermatitis (ICD).
Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.
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.
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 compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.
Eyelid dermatitis is commonly related to atopic dermatitis or allergic contact dermatitis. Volatile substances, tosylamide, epoxy hardeners, insect sprays, and lemon peel oil may be implicated, with many cases of eyelid contact dermatitis being caused by substances transferred by the hands to the eyelids.
Poison ivy is a type of allergenic plant in the genus Toxicodendron native to Asia and North America. Formerly considered a single species, Toxicodendron radicans, poison ivies are now generally treated as a complex of three separate species: Toxicodendron radicans, Toxicodendron rydbergii, and Toxicodendron orientale. They are well known for causing urushiol-induced contact dermatitis, an itchy, irritating, and sometimes painful rash, in most people who touch it. The rash is caused by urushiol, a clear liquid compound in the plant's sap. They are variable in appearance and habit, and despite its common name, it is not a "true" ivy (Hedera), but rather a member of the cashew and pistachio family (Anacardiaceae). T. radicans is commonly eaten by many animals, and the seeds are consumed by birds, but poison ivy is most often thought of as an unwelcome weed.
Dimethylol ethyleneurea is an organic compound derived from formaldehyde and urea. It is a colourless solid that is used for treating cellulose-based heavy fabrics to inhibit wrinkle formation. Dimethylol ethylene urea (DMEU) bonds with the hydroxyl groups present in long cellulose chains and prevents the formation hydrogen bonding between the chains, the primary cause of wrinkling. This treatment produces permanently wrinkle-resistant fabrics and is different from the effects achieved from using fabric softeners. An additional names for DMEU includes 1,3-bis(hydroxymethyl)-tetrahydro-2-imidazolone.
Para tertiary butylphenol formaldehyde resin also known as p-tert-butylphenol-formaldehyde resin (PTBP-FR) or 4-(1,1-dimethylethyl) phenol is a phenol-formaldehyde resin found in commercial adhesives, and in particular in adhesives used to bond leather and rubber. It has broad usage in a large variety of industries and can be found in many household items and textile products, and in particular it is used in the manufacture of shoes.
Cidoxepin (former developmental code name P-4599), also known as cis-doxepin or (Z)-doxepin, is a tricyclic antidepressant which was developed in the 1960s but was never marketed. It is the cis or (Z) stereoisomer of doxepin, a mixture of (E) and (Z) isomers that is used commercially in a ratio of approximately 85:15 with cidoxepin as a relatively minor constituent. However, the drug has similar activity to that of doxepin, acting as a serotonin–norepinephrine reuptake inhibitor, H1 receptor antagonist, and anticholinergic, and notably is thought to have more antidepressant activity than trans-doxepin. The central anticholinergic activity of cidoxepin has been reported to be 3-fold greater than that of the trans isomer in mice.