Quaternium-15
{{short description|Salt used as a surfactant}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Name = Cis/trans-Quaternium-15
| verifiedrevid = 464378185
| ImageFile = Undefined_Quaternium-15.png
| ImageSize = 169
| IUPACName = 1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride
| OtherNames = {{unbulleted list|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}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 23621565
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E40U03LEM0
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = LIT014L4RH
| UNII1_Comment = Cis-isomer
| SMILES = C1N2CN3CN1C[N+](C2)(C3)CC=CCl.[Cl-]
| 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
| InChIKey = UKHVLWKBNNSRRR-REWHXWOFAS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UKHVLWKBNNSRRR-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 4080-31-3
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 51229-78-8
| CASNo1_Comment = Cis-isomer
| PubChem = 6435993
}}
|Section2={{Chembox Properties
| C=9 | H=16 | Cl=2 | N=4
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| ExternalSDS = Sigma Aldrich{{Sigma-Aldrich|id=C3892|name=1-(cis-3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride |accessdate=2014-10-07}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS02}}{{GHS09}}{{GHS07}}{{GHS08}}
| HPhrases = {{H-phrases|228|302|315|317|361|411}}
| PPhrases = {{P-phrases|210|273|280}}
}}
}}
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.{{cite journal|last1=de Groot|first1=Anton C.|last2=White|first2=Ian R.|last3=Flyvholm|first3=Mari-Ann|last4=Lensen|first4=Gerda|last5=Coenraads|first5=Pieter-Jan|title=Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy|journal=Contact Dermatitis|volume=62|issue=1|pages=2–17|doi=10.1111/j.1600-0536.2009.01615.x|year=2010|pmid=20136875 |s2cid=39758546}}{{cite journal|last1=De Groot|first1=Anton|last2=Geier|first2=Johannes|last3=Flyvholm|first3=Mari-Ann|last4=Lensen|first4=Gerda|last5=Coenraads|first5=Pieter-Jan|title=Formaldehyde-releasers: Relationship to formaldehyde contact allergy, Part 2: Metalworking fluids and remainder|journal=Contact Dermatitis|date=22 June 2010|volume=63|issue=3|pages=129–139|doi=10.1111/j.1600-0536.2010.01715.x|pmid=20573163|s2cid=28278068}}
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.{{cn|date=September 2022}}
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.{{cite web |url=https://chemicalwatch.com/57303/european-commission-notifies-bans-restrictions-on-cmrs-in-cosmetics#overlay-strip |access-date=2 December 2019|title=European Commission notifies bans, restrictions on CMRS in cosmetics}}{{cite news |url=https://www.cnbc.com/2018/08/01/fda-begins-first-inquiry-of-lightly-regulated-cosmetics-industry.html |title=The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring|access-date=2 December 2019}}
= Allergic reaction =
Quaternium-15 is an allergen, and can cause dermatitis.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}} 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.{{cite web|url=http://dermnetnz.org/dermatitis/quaternium-allergy.html|title=Quaternium-15 contact allergy|work=DermNet NZ|author=New Zealand Dermatological Society|accessdate=2007-05-31}}
It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).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 In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).{{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 }}
Although quaternium-15 releases low amounts of formaldehyde.{{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}} Even so, Johnson & Johnson announced plans to phase out its use of quaternium-15 in cosmetic products by 2015 in response to consumer pressure.{{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}}{{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}}
See also
References
{{reflist}}
External links
- {{DermNet|dermatitis/quaternium-allergy}}
- {{CPID|id=138}}
- [http://hazmap.nlm.nih.gov/category-details?id=843&table=copytblagents Occupational Hazards - Quaternium-15] {{Webarchive|url=https://web.archive.org/web/20190624203329/http://hazmap.nlm.nih.gov/category-details?id=843&table=copytblagents |date=2019-06-24 }}