Quaternium-15

Cis/trans-Quaternium-15
Names
IUPAC name
1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride
Other names
  • Dowicil 75
  • Dowicil 100
  • Dowco 184
  • Dowicide Q
  • N-(3-chloroallyl) hexaminium chloride
  • hexamethylenetetramine chloroallyl chloride
  • 3,5,7-triaza-1-azoniaadamantane; 1-(3-chloroallyl)-chloride
Identifiers
4080-31-3 YesY
51229-78-8 Cis-isomer N
3D model (Jmol) Interactive image
ChemSpider 23621565 N
ECHA InfoCard 100.021.641
PubChem 6435993
UNII E40U03LEM0 YesY
Properties
C9H16Cl2N4
Molar mass 251.16 g·mol−1
Hazards
Safety data sheet Sigma Aldrich[1]
GHS pictograms
H228, H302, H315, H317, H361, H411[1]
P210, P273, P280[1]
Harmful XN; Highly flammable F+
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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 is an anti-microbial agent by virtue of being a formaldehyde releaser,[2][3] however this 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).

Synthesis

Quaternium-15 can be prepared by reacting hexamethylenetetramine with 1,3-dichloropropene to produce the product as a mixture of cis and trans isomers.

Applications

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.

Safety concerns

Allergic reaction

Quaternium-15 is an allergen, and can cause contact dermatitis in susceptible individuals.[4] 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.[5] It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).[6] In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).[7]

Cancer

Some consumer cosmetics contain quaternium-15 for its antimicrobial properties.[2] 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.[8] Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.[9][10]

See also

References

  1. 1 2 3 Sigma-Aldrich Co., 1-(cis-3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride. Retrieved on 2014-10-07.
  2. 1 2 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.
  3. 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.
  4. 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
  5. New Zealand Dermatological Society. "Quaternium-15 contact allergy". DermNet NZ. Retrieved 2007-05-31.
  6. 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
  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.
  8. "Formaldehyde". American Cancer Society. Retrieved 3 March 2016.
  9. "Johnson & Johnson to phase out potentially harmful chemicals by 2015". CBS News. Retrieved 3 March 2016.
  10. Thomas, Katie. "The 'No More Tears' Shampoo, Now With No Formaldehyde". The New York Times. Retrieved 3 March 2016.
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