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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