Quaternium-15

Synthesis

Quaternium-15 can be prepared by treating hexamethylenetetramine 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, and can cause dermatitis. 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. 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

References

1. {{Sigma-Aldrich
2. (2010). "Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy". Contact Dermatitis.
3. (22 June 2010). "Formaldehyde-releasers: Relationship to formaldehyde contact allergy, Part 2: Metalworking fluids and remainder". Contact Dermatitis.
4. "European Commission notifies bans, restrictions on CMRS in cosmetics".
5. "The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring".
6. (Nov 2005). "Allergic contact dermatitis to quaternium 15 in a moisturizing lotion". Australasia J Dermatol.
7. New Zealand Dermatological Society. "Quaternium-15 contact allergy". DermNet NZ.
8. "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology.
9. (2009). "Patch-test results of the North American Contact Dermatitis Group 2005–2006". Dermatitis.
10. "Formaldehyde".
11. "Johnson & Johnson to phase out potentially harmful chemicals by 2015".
12. (17 January 2014). "The 'No More Tears' Shampoo, Now With No Formaldehyde".