Formaldehyde releaser

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3D structure of Formaldehyde

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. 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[edit]

Cosmetics[edit]

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

Resins and plastics[edit]

Other uses[edit]

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

Safety[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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]

References[edit]

  1. ^ a b c d e f g h 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. ^ a b c d e f 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.
  21. ^ "Formaldehyde". American Cancer Society.
  22. ^ "Johnson & Johnson to phase out potentially harmful chemicals by 2015". Retrieved 2 December 2019.
  23. ^ a b "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.