Quaternium-15
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Names | |
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IUPAC name
1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride
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Other names
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Identifiers | |
4080-31-3 51229-78-8 Cis-isomer |
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ChemSpider | 23621565 |
Jmol 3D model | Interactive image |
PubChem | 6435993 |
UNII | E40U03LEM0 |
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Properties | |
C9H16Cl2N4 | |
Molar mass | 251.16 g·mol−1 |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Quaternium-15 (systematic name: hexamethylenetetramine chloroallyl chloride) is a quaternary ammonium salt used as a surfactant and preservative in many cosmetics and industrial substances. It is an anti-microbial agent by virtue of being a formaldehyde releaser,[1][2] however this can also cause contact dermatitis, a symptom of an allergic reaction, especially in those with sensitive skin.
It can be found under a variety of names, most commonly those of the 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 reacting hexamethylenetetramine with 1,3-dichloropropene to produce the product as a mixture of cis and trans isomers.
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; glues and adhesives.
Safety concerns
Quaternium-15 is an allergen, and can cause contact dermatitis in susceptible individuals.[3] 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.[4] It is the single most often found cause of allergic contact dermatitis of the hands (16.5% in 959 cases).[5] In 2005–06, it was the fourth-most-prevalent allergen in patch tests (10.3%).[6]
See also
References
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- ↑ Cahill J, Nixon R. Allergic contact dermatitis to quaternium 15 in a moisturizing lotion. Australasia J Dermatol. 2005 Nov;46(4):284–5. PMID 16197434
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ E. Warshaw, et al. "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology, Volume 57, Issue 2, pp. 301–314
- ↑ Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009 May–Jun;20(3):149-60.
External links
- Record in the Household Products Database of NLM
- Occupational Hazards - Quaternium-15
- Pages with broken file links
- Chemical articles with multiple CAS Registry Numbers
- Articles without EBI source
- Articles without KEGG source
- Articles with changed InChI identifier
- Pages using collapsible list with both background and text-align in titlestyle
- Cosmetics chemicals
- Preservatives
- Quaternary ammonium compounds