Quaternium-15

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.

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	4080-31-3 Y 51229-78-8 Cis-isomer Y
3D model (JSmol)	Interactive image
ChemSpider	23621565 N
ECHA InfoCard	100.102.448
PubChem CID	6435993
UNII	E40U03LEM0 Y LIT014L4RH Cis-isomer Y
CompTox Dashboard (EPA)	DTXSID0035748
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-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
SMILES C1N2CN3CN1C[N+](C2)(C3)CC=CCl.[Cl-]
Properties
Chemical formula	C9H16Cl2N4
Molar mass	251.16 g·mol−1
Hazards
GHS labelling:
Pictograms
Hazard statements	H228, H302, H315, H317, H361, H411[1]
Precautionary statements	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 YN ?) Infobox references

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.^{[citation needed]}

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 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.^[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

• Polyquaternium