1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloridechloroallyl chloride

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 Edit this at Wikidata
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
Safety data sheet Sigma Aldrich[1]
GHS pictograms GHS02: FlammableGHS09: Environmental hazardGHS07: HarmfulGHS08: Health hazard
H228, H302, H315, H317, H361, H411[1]
P210, P273, P280[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 used as a surfactant and preservative in many cosmetics and industrial substances. It acts as an antimicrobial agent because it acts as a formaldehyde releaser,[2][3] though doing so 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[]

Quaternium-15 along with formaldehyde has been banned in the EU since 2017 and a bill is under consideration in the US.[4][5]

Allergic reaction[]

Quaternium-15 is an allergen, and can cause contact dermatitis in susceptible individuals.[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]

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.[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. ^ a b c Sigma-Aldrich Co., 1-(cis-3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride. Retrieved on 2014-10-07.
  2. ^ a b 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.
  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. ^ "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 (Nov 2005). "Allergic contact dermatitis to quaternium 15 in a moisturizing lotion". Australasia J Dermatol. 46 (4): 284–5. doi:10.1111/j.1440-0960.2005.00210.x. PMID 16197434.
  7. ^ New Zealand Dermatological Society. "Quaternium-15 contact allergy". DermNet NZ. Retrieved 2007-05-31.
  8. ^ Warshaw, E.; et al. (2007). "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology. 57 (2): 301–314. doi:10.1016/j.jaad.2007.04.016. PMID 17553593.
  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.
  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. "The 'No More Tears' Shampoo, Now With No Formaldehyde". The New York Times. Retrieved 3 March 2016.

External links[]