formaldehyde releasers
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A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases
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 ...
. 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.


Examples

Many compounds have been formulated a formaldehyde-releasers. *
Quaternium-15 Quaternium-15 (systematic name: hexamethylenetetramine chloroallyl chloride) 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 ...
(Dowicil 200; Dowicil 75; Dowicil 100; Dowco 184; Dowicide Q). It was used in low concentrations in cosmetics but has been banned in the EU since 2017 and a bill is under consideration in the US. * DMDM hydantoin * (ethylenedioxy)dimethanol (EDDM) *(Benzyloxy)methanol (BHF, benzylhemiformal) * 2,2',2''-(Hexahydro-1,3-5-triazine-1,3,5-triyl-)triethanol (HHT) * Tetramethylolacetylenediurea (TMAD) * 1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione (DMDMH) * 3,3'-Methylenebis -methyloxazolidine(MBO) * Imidazolidinyl urea (Germall 115) for cosmetics *
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. It is used in many cosmetics, skin care prod ...
(Germall II) for cosmetics * Tris(hydroxymethyl) nitromethane (Tris Nitro) for cosmetics * tris(N-hydroxyethyl) hexahydrotriazine (Grotan® BK) * Sodium hydroxymethylglycinate for cosmetics


Unintentional formaldehyde releasers

Some materials release formaldehyde unintentionally. These materials have also elicited considerable controversy, especially when these materials have household applications such as flooring. Examples: * Delrin or Acetal *
Phenol formaldehyde resin Phenol formaldehyde resins (PF) or phenolic resins (also infrequently called phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commerc ...
*
Urea formaldehyde resin 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 adhesive ...
*
Melamine resin Melamine resin or melamine formaldehyde (also shortened to melamine) is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. ...


Uses

They are found in fuels, cosmetics, toiletries, cleaning agents, adhesives, paints, lacquers, fertilizers, and metalworking fluids. They are found in lysing agent for cells for in vitro diagnostic reagents. Photo-chemicals and press room chemicals also contain these releasers.


Safety

Formaldehyde is dangerous to human health. In 2011, the US National Toxicology Program described formaldehyde as " known to be a human carcinogen". The danger of formaldehyde is a major reason for the development of formaldehyde releasers which release formaldehyde slowly at lower levels.


Allergic reaction

Levels of 200–300 p.p.m. formaldehyde in cosmetic products can cause
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 ...
in short-term use on normal skin. A patch test study found that DMDM hydantoin in cosmetic products could increase the risk of cosmetic dermatitis. Some people have a contact allergy to imidazolidinyl urea causing dermatitis.Review of toxicological data
(NTP NIEHS)
Such people are often also allergic to diazolidinyl urea. In 2005–06, it was the 14th-most-prevalent allergen 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.


Cancer

Some consumer cosmetics contain quaternium-15 for its antimicrobial properties. The American Cancer Society states that although quaternium-15 releases formaldehyde, a known carcinogen in laboratory test animals at relatively high doses, because the amount of formaldehyde released from these products is low, it is unclear that avoiding quaternium-15 in cosmetics provides any health benefits. Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.


Importance

Formaldehyde in the EU is restricted to a maximum allowed concentration in finished products no greater than 0.2%. However, there are hidden sources of formaldehyde such as these formaldehyde releasers. As well, patch tests are prone to false positives at even low concentrations and not a reliable test. Sensitization to formaldehyde has been decreasing since 1980 due in part to the replacement of formaldehyde by these formaldehyde releasers. As of 2009, frequency of sensitization to formaldehyde is stable at 2–3% in Europe. It might be as high as 9% in the USA.


Alternatives

There are three groups of broad-spectrum preservatives with the most safety and efficacy. *
Paraben Parabens are a class of widely used preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid (also known as 4-hydroxybenzoic acid). Parabens are effective p ...
s *Formaldehyde releasers *
Halogenate In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polyme ...
d compounds The FDA requires that cosmetics have an effective preservative, and microbial challenge testing is conducted. The EU's Cosmetic Directive 76/768/EEC requires the use of a preservative on an approved list.


Analysis

There are many ways to test and quantify formaldehyde. However these methods are not suitable for the determination of free formaldehyde in cosmetics with formaldehyde releasers since these methods often accelerate release of formaldehyde.{{cite journal , doi=10.1007/s00216-018-1287-0 , pmid=30062513 , title=GDME-based methodology for the determination of free formaldehyde in cosmetics and hygiene products containing formaldehyde releasers , journal=Analytical and Bioanalytical Chemistry , volume=410 , issue=26 , pages=6873–6880 , year=2018 , last1=Brandão , first1=Pedro Francisco , last2=Ramos , first2=Rui Miguel , last3=Rodrigues , first3=José António , s2cid=51880356 The physical method by 13C NMR spectroscopy does not affect the equilibrium between free and donor sources of formaldehyde and might be the best way to test for formaldehyde releasers.


References

Antimicrobials