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It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).<ref>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</ref> In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).<ref name="Zug KA 2006">{{cite journal | last1 = Zug | first1 = KA | last2 = Warshaw | first2 = EM | last3 = Fowler | first3 = JF Jr | last4 = Maibach | first4 = HI | last5 = Belsito | first5 = DL | last6 = Pratt | first6 = MD | last7 = Sasseville | first7 = D | last8 = Storrs | first8 = FJ | last9 = Taylor | first9 = JS | last10 = Mathias | first10 = CG | last11 = Deleo | first11 = VA | last12 = Rietschel | first12 = RL | last13 = Marks | first13 = J | year = 2009 | title = Patch-test results of the North American Contact Dermatitis Group 2005–2006 | journal = Dermatitis | volume = 20 | issue = 3| pages = 149–60 | doi = 10.2310/6620.2009.08097 | pmid = 19470301 | s2cid = 24088485 }}</ref> It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).<ref>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</ref> In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).<ref name="Zug KA 2006">{{cite journal | last1 = Zug | first1 = KA | last2 = Warshaw | first2 = EM | last3 = Fowler | first3 = JF Jr | last4 = Maibach | first4 = HI | last5 = Belsito | first5 = DL | last6 = Pratt | first6 = MD | last7 = Sasseville | first7 = D | last8 = Storrs | first8 = FJ | last9 = Taylor | first9 = JS | last10 = Mathias | first10 = CG | last11 = Deleo | first11 = VA | last12 = Rietschel | first12 = RL | last13 = Marks | first13 = J | year = 2009 | title = Patch-test results of the North American Contact Dermatitis Group 2005–2006 | journal = Dermatitis | volume = 20 | issue = 3| pages = 149–60 | doi = 10.2310/6620.2009.08097 | pmid = 19470301 | s2cid = 24088485 }}</ref>


Although quaternium-15 releases low amounts of formaldehyde.<ref>{{cite web|title=Formaldehyde|url=http://www.cancer.org/cancer/cancercauses/othercarcinogens/intheworkplace/formaldehyde|website=American Cancer Society|access-date=3 March 2016}}</ref> Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.<ref>{{cite web|title=Johnson & Johnson to phase out potentially harmful chemicals by 2015|url=http://www.cbsnews.com/news/johnson-johnson-to-phase-out-potentially-harmful-chemicals-by-2015/|website=CBS News|access-date=3 March 2016}}</ref><ref>{{cite news|last1=Thomas|first1=Katie|title=The 'No More Tears' Shampoo, Now With No Formaldehyde|url=https://www.nytimes.com/2014/01/18/business/johnson-johnson-takes-first-step-in-removal-of-questionable-chemicals-from-products.html|website=The New York Times|date=17 January 2014|access-date=3 March 2016}}</ref> Although quaternium-15 releases low amounts of formaldehyde.<ref>{{cite web|title=Formaldehyde|url=http://www.cancer.org/cancer/cancercauses/othercarcinogens/intheworkplace/formaldehyde|website=American Cancer Society|access-date=3 March 2016|archive-date=30 November 2016|archive-url=https://web.archive.org/web/20161130121821/http://www.cancer.org/cancer/cancercauses/othercarcinogens/intheworkplace/formaldehyde|url-status=dead}}</ref> Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.<ref>{{cite web|title=Johnson & Johnson to phase out potentially harmful chemicals by 2015|url=http://www.cbsnews.com/news/johnson-johnson-to-phase-out-potentially-harmful-chemicals-by-2015/|website=CBS News|access-date=3 March 2016}}</ref><ref>{{cite news|last1=Thomas|first1=Katie|title=The 'No More Tears' Shampoo, Now With No Formaldehyde|url=https://www.nytimes.com/2014/01/18/business/johnson-johnson-takes-first-step-in-removal-of-questionable-chemicals-from-products.html|website=The New York Times|date=17 January 2014|access-date=3 March 2016}}</ref>


== See also == == See also ==
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* {{DermNet|dermatitis/quaternium-allergy}} * {{DermNet|dermatitis/quaternium-allergy}}
* {{CPID|id=138}} * {{CPID|id=138}}
* * {{Webarchive|url=https://web.archive.org/web/20190624203329/http://hazmap.nlm.nih.gov/category-details?id=843&table=copytblagents |date=2019-06-24 }}


] ]

Latest revision as of 17:02, 15 September 2024

Salt used as a surfactant
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.102.448 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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-1Key: UKHVLWKBNNSRRR-UHFFFAOYSA-M
  • 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-1Key: UKHVLWKBNNSRRR-REWHXWOFAS
SMILES
  • C1N2CN3CN1C(C2)(C3)CC=CCl.
Properties
Chemical formula C9H16Cl2N4
Molar mass 251.16 g·mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS09: Environmental hazardGHS07: Exclamation markGHS08: Health hazard
Hazard statements H228, H302, H315, H317, H361, H411
Precautionary statements P210, P273, P280
Safety data sheet (SDS) Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

Allergic reaction

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

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

See also

References

  1. ^ 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.

External links

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