Tosylamide/formaldehyde resin

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Tosylamide/formaldehyde resin
Names
Systematic IUPAC name
poly[4-methylbenzenesulfonamide-alt-methanal]
Other names
  • Toluenesulfonamide/formaldehyde resin
  • Formaldehyde-p-toluenesulfonamide copolymer
  • Santolite MHP
  • Santolite MS
Identifiers
ECHA InfoCard 100.132.132 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 607-493-7
PubChem CID
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).

Tosylamide/formaldehyde resin (TSFR) is a polymeric resin used as a plasticizer and secondary film-forming agent in nail polishes. While it was still in use as of 2023, its use has been diminishing in favor of hypoallergenic alternatives, due to the prevalence of reactions causing allergic contact dermatitis of the eyelids, face, and neck.

Contents

Production

TSFR is produced by condensing p-tosylamide  [ de ] (often impure, containing o-tosylamide  [ de ]) with formaldehyde. It consists of a mixture of short oligomers with repeating unit −N(Ts)CH2, terminated by −NHTs or −N(Ts)CH2OH groups. [2]

Allergenicity

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  [ de ]isophthalic acidtrimellitic anhydride). [7]

Related Research Articles

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References

  1. "Formaldehyde-p-toluenesulfonamide copolymer". CAS Common Chemistry . American Chemical Society.
  2. 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.
  3. 1 2 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.
  4. 1 2 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.
  5. "Tosylamide/Formaldehyde Resin". Cosmetics Info. Personal Care Products Council. 2023-10-20. Archived from the original on 2024-01-10.
  6. 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.
  7. 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.