Formaldehyde releaser

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

3D structure of Formaldehyde

Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. There are at least 42 main formaldehyde-releasers.[1] They are found in cosmetics, toiletries, cleaning agents, adhesives, paints, lacquers and metalworking fluids.[1]

Formaldehyde‐releasers can be further defined as:

  • Substances that release formaldehyde as a result of decomposition
  • Chemicals synthesized from formaldehyde that may still contain residues of free formaldehyde such as melamine/formaldehyde and urea‐formaldehyde resins.

The main ones are,

Quaternium-15

DMDM hydantoin

Ureas (imidazolidinyl, or diazolidinyl)

Benzylhemiformal[1][2]

Uses

Cosmetics

Formaldehyde releasers are often used as an antimicrobial preservative in cosmetics. Examples include:

Resins and plastics

Other uses
  • Production of fertilizers;
  • Lysing agent for cells for in vitro diagnostic reagents
  • Photo-chemicals and press room chemicals[7]

Safety

Formaldehyde is dangerous to human health.[8][9] In 2011, the US National Toxicology Program described formaldehyde as "known to be a human carcinogen".[10][11][12]

The danger of formaldehyde is a major reason for the development of formaldehyde releasers which release formaldehyde slowly at lower levels.[13]

Allergic reaction

Levels of 200–300 p.p.m. formaldehyde in cosmetic products can cause contact dermatitis in short-term use on normal skin.[13] Quaternium-15 is an allergen, and can cause dermatitis in susceptible individuals.[14] Many of those with an allergy to quaternium-15 are also allergic to formaldehyde. At low pHs it would be expected to release significant amounts of formaldehyde due to acid hydrolysis via the Delepine reaction.

Allergic sensitivity to quaternium-15 can be detected using a patch test.[15] It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).[16] In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).[17]

A patch test study found that DMDM hydantoin in cosmetic products could increase the risk of cosmetic dermatitis.[13]

Some people have a contact allergy to imidazolidinyl urea causing dermatitis.[18] Such people are often also allergic to diazolidinyl urea. In 2005–06, it was the 14th-most-prevalent allergen in patch tests (3.7%).[19]

Cancer

Some consumer cosmetics contain quaternium-15 for its antimicrobial properties.[20] 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.[21] Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.[22]

Importance

Formaldehyde in the EU is restricted to a maximum allowed concentration in finished products no greater than 0.2%.[1] 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.[1]

Sensitization to formaldehyde has been decreasing since 1980 due in part to the replacement of formaldehyde by these formaldehyde releasers.[1] As of 2009, frequency of sensitization to formaldehyde is stable at 2–3% in Europe.[1] It might be as high as 9% in the USA.[1][13]

Alternatives

There are three groups of broad spectrum preservatives with the most safety and efficacy.[23]

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.[23]

Analysis

There are many ways to test and quantify formaldehyde.[13] 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.[24]

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.[13]

gollark: Anyway, since I could use Urn Street earlier, that implies HydroNitrogen got crazed to ban me too...
gollark: My game keeps freezing a bit then crashing with exitcode 6.
gollark: The road network is also partly hydronitrogen-owned, which doesn't help.
gollark: It's one of those things which while *strictly speaking* not required *is* very important.
gollark: Well, at least I don't have a shop in wolfmall...

References
  1. De Groot, Anton C.; Flyvholm, Mari-Ann; Lensen, Gerda; Menné, Torkil; Coenraads, Pieter-Jan (2009). "Formaldehyde-releasers: Relationship to formaldehyde contact allergy. Contact allergy to formaldehyde and inventory of formaldehyde-releasers" (PDF). Contact Dermatitis. 61 (2): 63–85. doi:10.1111/j.1600-0536.2009.01582.x. PMID 19706047.
  2. "Benzylhemiformal | Allergic Contact Dermatitis Database". Retrieved 2 December 2019.
  3. "European Commission notifies bans, restrictions on CMRS in cosmetics". Retrieved 2 December 2019.
  4. "The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring". Retrieved 2 December 2019.
  5. "DMH | C5H8N2O2 | ChemSpider".
  6. https://core.ac.uk/download/pdf/12939269.pdf
  7. "FORMALDEHYDE AND FORMALDEHYDE RELEASERS Investigation Report". Retrieved 2 December 2019.
  8. "Formaldehyde", Formaldehyde, 2-Butoxyethanol and 1-tert-Butoxypropan-2-ol (PDF), IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 88, Lyon, France: International Agency for Research on Cancer, 2006, pp. 39–325, ISBN 978-92-832-1288-1
  9. "Formaldehyde (gas)", Report on Carcinogens, Eleventh Edition (PDF), U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, 2005
  10. Harris, Gardiner (2011-06-10). "Government Says 2 Common Materials Pose Risk of Cancer". New York Times. Archived from the original on 2019-03-28. Retrieved 2011-06-11.
  11. National Toxicology Program (2011-06-10). "12th Report on Carcinogens". National Toxicology Program. Archived from the original on 2011-06-08. Retrieved 2011-06-11.
  12. National Toxicology Program (2011-06-10). "Report On Carcinogens - Twelfth Edition - 2011" (PDF). National Toxicology Program. Archived from the original on 2011-06-12. Retrieved 2011-06-11.
  13. de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW (1988). "Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy". Contact Dermatitis. 18 (4): 197–201. doi:10.1111/j.1600-0536.1988.tb02802.x. PMID 3378426.
  14. Cahill J, Nixon R. Allergic contact dermatitis to quaternium 15 in a moisturizing lotion. Australasia J Dermatol. 2005 Nov;46(4):284–5. PMID 16197434
  15. New Zealand Dermatological Society. "Quaternium-15 contact allergy". DermNet NZ. Retrieved 2007-05-31.
  16. E. Warshaw, et al. "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology, Volume 57, Issue 2, pp. 301–314
  17. 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.
  18. Review of toxicological data (NTP NIEHS)
  19. 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.
  20. de Groot, Anton C.; White, Ian R.; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan (2010). "Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy". Contact Dermatitis. 62 (1): 2–17. doi:10.1111/j.1600-0536.2009.01615.x. PMID 20136875. S2CID 39758546.
  21. "Formaldehyde". American Cancer Society.
  22. "Johnson & Johnson to phase out potentially harmful chemicals by 2015". Retrieved 2 December 2019.
  23. "Alternative Cosmetic Preservatives - What are your options? - Chemists Corner". Retrieved 2 December 2019.
  24. Brandão, Pedro Francisco; Ramos, Rui Miguel; Rodrigues, José António (2018). "GDME-based methodology for the determination of free formaldehyde in cosmetics and hygiene products containing formaldehyde releasers". Analytical and Bioanalytical Chemistry. 410 (26): 6873–6880. doi:10.1007/s00216-018-1287-0. PMID 30062513.
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