Tosylamide/formaldehyde resin
| Names | |
|---|---|
| Systematic IUPAC name
poly[4-methylbenzenesulfonamide-alt-methanal] | |
Other names
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| Identifiers | |
| ECHA InfoCard | 100.132.132 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| (C7H9NO2S·CH2O)n (n ≤ 10) | |
| Molar mass | Variable (400–1900 g·mol−1) |
| Melting point | 82 °C (180 °F; 355 K)[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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Tosylamide/formaldehyde resin (TSFR) is a polymeric resin used as a plasticizer and secondary film-forming agent in nail polishes. While it is still in use as of 2023,[update] it has progressively been phased out in favor of hypoallergenic alternatives, due to the prevalence of reactions causing allergic contact dermatitis of the eyelids, face, and neck.
Production
[edit]TSFR is produced by condensing p-tosylamide (often mixed with o-tosylamide) with formaldehyde. It consists of a mixture of short oligomers with repeating unit −N(Ts)CH2−, terminated by −NHTs or N(CH2OH)Ts groups.[2]
Allergenicity
[edit]Nail polishes containing TSFR were first introduced in 1939, becoming a major cause of allergic contact dermatitis of the eyelids, face, and neck.[3][4] Allergic responses are caused by the water-soluble contaminants 5-tosyl-1,3,5-dioxazinane (TsN(−)(CH2OCH2OCH2−)) and 3,5-ditosyl-1,3,5-oxadiazinane (TsN(−)(CH2N(Ts)CH2OCH2−)), rather than formaldehyde, which is only present in trace quantities (<0.5%).[3][4][5]
Since the early 2010s, the prevalence of allergic reactions to TSFR has decreased, due to the widespread use of hypoallergenic alternatives such as tosylamide/epoxy resin (first introduced in the late 1980s[6]), cellulose acetate butyrate, and polyester resins (e.g. 2,2,4-Trimethyl-1,3-pentanediol–isophthalic acid–trimellitic anhydride).[7]
References
[edit]- ^ "Formaldehyde-p-toluenesulfonamide copolymer". CAS Common Chemistry. American Chemical Society.
- ^ Chiva, V.; Lecacheur, M.; Faure, R.; Gallo, R.; Wimmer, E. (15 July 1993). "Structure of Toluene Sulfonamide Formol Resins: Molecular Models from Mechanistic Schemes and Analytical Results". Journal of Applied Polymer Science. 49 (3): 461–467. doi:10.1002/app.1993.070490310.
- ^ a b Hausen, B. M.; Milbrodt, M.; Koenig, W. A. (September 1995). "The allergens of nail polish: (I). Allergenic constituents of common nail polish and toluenesulfonamide‐formaldehyde resin (TS‐F‐R)". Contact Dermatitis. 33 (3): 157–164. doi:10.1111/j.1600-0536.1995.tb00537.x.
- ^ a b Park, Michelle E.; Zippin, Jonathan H. (January 2014). "Allergic Contact Dermatitis to Cosmetics". Dermatologic Clinics. 32 (1): 6. doi:10.1016/j.det.2013.09.006.
- ^ "Tosylamide/Formaldehyde Resin". Cosmetics Info. Personal Care Products Council. 2023-10-20. Archived from the original on 2024-01-10.
- ^ Sandewicz, Robert W. (2017). "Formulation of Nail Care Products". In Dayan, Nava (ed.). Handbook of Formulating Dermal Applications. Hoboken, New Jersey : Beverly, Massachusetts : Scrivener Publishing: John Wiley & Sons, Inc. pp. 539–590. ISBN 9781119364238.
- ^ Lee, Senhong; Maor, Danit; Palmer, Amanda; Nixon, Rosemary L. (September 2018). "Declining prevalence of allergic contact dermatitis caused by tosylamide/formaldehyde in nail polish". Contact Dermatitis. 79 (3): 184–185. doi:10.1111/cod.13020. Archived from the original on 26 May 2022.