Quaternium-15

Last updated
Cis/trans-Quaternium-15
Undefined Quaternium-15.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.102.448 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H16ClN4.ClH/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14;/h1-2H,3-9H2;1H/q+1;/p-1 X mark.svgN
    Key: UKHVLWKBNNSRRR-UHFFFAOYSA-M X mark.svgN
  • InChI=1/C9H16ClN4.ClH/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14;/h1-2H,3-9H2;1H/q+1;/p-1
    Key: UKHVLWKBNNSRRR-REWHXWOFAS
  • C1N2CN3CN1C[N+](C2)(C3)CC=CCl.[Cl-]
Properties
C9H16Cl2N4
Molar mass 251.16 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-pollu.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
H228, H302, H315, H317, H361, H411 [1]
P210, P273, P280 [1]
Safety data sheet (SDS)Sigma Aldrich [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Quaternium-15 (systematic name: hexamethylenetetramine chloroallyl chloride) is a quaternary ammonium salt that has been used as a surfactant and preservative. It acts as an antimicrobial agent because it slowly releases formaldehyde, which is a preservative with biocidal properties.

Contents

Both quaternium-15 and formaldehyde release agents have been the subjects of controversy. They are often banned in US and Europe. [2] [3]

It can be found under a variety of names, including 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 treating hexamethylenetetramine with 1,3-dichloropropene. A mixture of cis and trans isomers are produced.[ citation needed ]

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, and glues and adhesives.

Safety concerns

Quaternium-15 has been banned in the EU since 2017 and a bill was introduced in the US in 2017 to require the FDA to investigate its safety. [4] [5]

Allergic reaction

Quaternium-15 is an allergen, and can cause dermatitis. [6] 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. [7] It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases). [8] In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%). [9]

Although quaternium-15 releases low amounts of formaldehyde. [10] Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure. [11] [12]

See also

Related Research Articles

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<span class="mw-page-title-main">Lip licker's dermatitis</span> Medical condition

Lip licker's dermatitis is a type of skin inflammation around the lips due to damage by saliva from repetitive lip licking and is classified as a subtype of irritant contact cheilitis. The resulting scaling, redness, chapping, and crusting makes a well-defined ring around the lips. The rash may extend as far as the tongue can reach and usually does not occur at the corners of the mouth. It commonly occurs during winter months but some people can have it year-round if lip licking is a chronic habit.

<span class="mw-page-title-main">Metal allergy</span> Medical condition

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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. ↑ 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.
  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. 63 (3): 129–139. doi:10.1111/j.1600-0536.2010.01715.x. PMID   20573163. S2CID   28278068.
  4. ↑ "European Commission notifies bans, restrictions on CMRS in cosmetics" . Retrieved 2 December 2019.
  5. ↑ "The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring" . Retrieved 2 December 2019.
  6. ↑ 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
  7. ↑ New Zealand Dermatological Society. "Quaternium-15 contact allergy". DermNet NZ. Retrieved 2007-05-31.
  8. ↑ 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
  9. ↑ 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 (2009). "Patch-test results of the North American Contact Dermatitis Group 2005–2006". Dermatitis. 20 (3): 149–60. doi:10.2310/6620.2009.08097. PMID   19470301. S2CID   24088485.
  10. ↑ "Formaldehyde". American Cancer Society. Archived from the original on 30 November 2016. Retrieved 3 March 2016.
  11. ↑ "Johnson & Johnson to phase out potentially harmful chemicals by 2015". CBS News. Retrieved 3 March 2016.
  12. ↑ Thomas, Katie (17 January 2014). "The 'No More Tears' Shampoo, Now With No Formaldehyde". The New York Times. Retrieved 3 March 2016.
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