Quaternium-15 (systematic name: hexamethylenetetramine chloroallyl chloride) is a

quaternary ammonium salt In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations ...

that has been used as a

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

and

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...

. It acts as an

antimicrobial An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...

agent because it slowly releases

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

, 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 The Dow Chemical Company, officially Dow Inc., is an American multinational chemical corporation headquartered in Midland, Michigan, United States. The company is among the three largest chemical producers in the world. Dow manufactures plastic ...

: 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 Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s ...

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 is under consideration in the US.

Allergic reaction

Quaternium-15 is an

allergen An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical terms ...

, 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. 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.

References

External links