Quaternium-15

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Cis/trans-Quaternium-15
Undefined Quaternium-15.png
Identifiers
CAS number 4080-31-3 YesY, 51229-78-8 Cis-isomer
PubChem 6435993
ChemSpider 23621565 N
UNII E40U03LEM0 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H16Cl2N4
Molar mass 251.16 g mol−1
Hazards
MSDS Sigma Aldrich[1]
GHS pictograms GHS-pictogram-flamme.svgGHS-pictogram-pollu.svgGHS-pictogram-exclam.svgGHS-pictogram-silhouete.svg
GHS hazard statements H228, H302, H315, H317, H361, H411[1]
GHS precautionary statements P210, P273, P280[1]
EU classification Harmful XN; Highly flammable F+
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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[edit]

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[edit]

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 pH's it would be expeted 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]

See also[edit]

References[edit]

  1. ^ a b c 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. "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.

External links[edit]