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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.102.448
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 ☒N
    Key: UKHVLWKBNNSRRR-UHFFFAOYSA-M ☒N
  • 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:
GHS02: FlammableGHS09: Environmental hazardGHS07: Exclamation markGHS08: Health hazard
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

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.

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

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. 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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