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 pH values, 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 }}