Quaternium-15

Salt used as a surfactant From Wikipedia, the free encyclopedia

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,[2] which is a preservative with biocidal properties.

Quick facts Names, Identifiers ...
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
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
GHS labelling:
GHS02: FlammableGHS09: Environmental hazardGHS07: Exclamation markGHS08: Health hazard
H228, H302, H315, H317, H361, H411[1]
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).
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Both quaternium-15 and formaldehyde release agents have been the subjects of controversy. They are banned in much of the 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]

Even though quaternium-15 releases low amounts of formaldehyde,[10] 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

External links

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