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

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

that has been used as a

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

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 ...

. It acts as an

antimicrobial An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth (bacteriostatic agent). Antimicrobial medicines can be grouped according to the microorganisms they are used to treat. For example, antibiotics are used aga ...

agent because it slowly releases

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

, 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 is an American multinational corporation headquartered in Midland, Michigan, United States. The company was among the three largest chemical producers in the world in 2021. It is the operating subsidiary of Dow Inc., ...

: 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 (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and p ...

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 was introduced in the US in 2017 to require the FDA to investigate its safety.

Allergic reaction

Quaternium-15 is an

allergen An allergen is an otherwise harmless substance that triggers an allergic reaction in sensitive individuals by stimulating an immune response. In technical terms, an allergen is an antigen that is capable of stimulating a type-I hypersensitivi ...

, and can cause

dermatitis Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened ...

.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 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 A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin. Patch testing helps identify which substances may be causing a delayed-type allergic reaction in a patient and ...

. It is the single most often found cause of allergic

contact dermatitis Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes ...

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