3D model (JSmol)
|Molar mass||251.16 g·mol−1|
|Safety data sheet||Sigma Aldrich|
|H228, H302, H315, H317, H361, H411|
|P210, P273, P280|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Quaternium-15 (systematic name: hexamethylenetetramine chloroallyl chloride) is a quaternary ammonium salt used as a surfactant and preservative in many cosmetics and industrial substances. It acts as an antimicrobial agent because it acts as a formaldehyde releaser, though doing so can also cause contact dermatitis, a symptom of an allergic reaction, especially in those with sensitive skin.
It can be found under a variety of names, most commonly those of the Dow Chemical Company: Dowicil 200 (cis isomer only), Dowicil 75 and Dowicil 100 (both a mix of cis and trans isomers).
The isolated cis-compound is used primarily in cosmetic applications, with a maximum permitted concentration in the EU of 0.2%. The mixed product (cis- and trans-) is used in a wider range of formulations such as: emulsifiable metal-cutting fluids; latex and emulsion paints; liquid floor polishes and floor waxes; glues and adhesives.
Quaternium-15 is an allergen, and can cause contact dermatitis in susceptible individuals. 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. It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases). In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).
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.
- Sigma-Aldrich Co., 1-(cis-3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride. Retrieved on 2014-10-07.
- de Groot, Anton C.; White, Ian R.; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan. "Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy". Contact Dermatitis. 62 (1): 2–17. doi:10.1111/j.1600-0536.2009.01615.x.
- De Groot, Anton; Geier, Johannes; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan (22 June 2010). "Formaldehyde-releasers: Relationship to formaldehyde contact allergy, Part 2: Metalworking fluids and remainder". Contact Dermatitis: no–no. doi:10.1111/j.1600-0536.2010.01715.x.
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- 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
- 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.
- "Formaldehyde". American Cancer Society. Retrieved 3 March 2016.
- "Johnson & Johnson to phase out potentially harmful chemicals by 2015". CBS News. Retrieved 3 March 2016.
- Thomas, Katie. "The 'No More Tears' Shampoo, Now With No Formaldehyde". The New York Times. Retrieved 3 March 2016.