Scotchgard

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Scotchgard is a 3M brand of products, a stain and durable water repellent applied to fabric, furniture, and carpets to protect them from stains. Scotchgard products typically rely on organofluorine chemicals as the main active ingredient along with petroleum distillate solvents. [1]

Contents

Development of the formula

The original formula for Scotchgard was discovered accidentally in 1952 by 3M chemists Patsy Sherman and Samuel Smith, although Patsy Sherman holds 13 patents regarding Scotchgard and is generally recognized as the scientist who discovered Scotchgard's possibilities.

Sales began in 1956, and in 1973 the two chemists received a patent for the formula. [1] [2]

C8 fluorinated urethane constituent that has later been replaced by a C4 alternative Scotchgard C8.svg
C8 fluorinated urethane constituent that has later been replaced by a C4 alternative

3M reformulated Scotchgard and since June 2003 has replaced PFOS with perfluorobutanesulfonic acid (PFBS). [4] PFBS has a much shorter half-life in people than PFOS (a little over one month vs. 5.4 years). [5] 3M now states that Scotchgard utilizes a proprietary fluorinated urethane. [6]

Environmental concerns

During 1999, the United States Environmental Protection Agency (EPA) began an investigation into the class of chemicals used in Scotchgard, after receiving information on the global distribution and toxicity of perfluorooctane sulfonate (PFOS), [7] the "key ingredient" [5] of Scotchgard. The compound perfluorooctanesulfonamide (PFOSA), a PFOS precursor, was an ingredient [8] and also has been described as the "key ingredient" [9] of Scotchgard. Under US EPA pressure, [10] in May 2000, 3M announced the phaseout of the production of PFOA, PFOS, and PFOS-related products. [11] [12] In May 2009, PFOS was determined to be a persistent organic pollutant (POP) by the Stockholm Convention. [13] Following the EPA's investigation into 3M Contamination of Minnesota Groundwater, in 2018, 3M agreed to pay the state of Minnesota $850 million to settle a $5 billion lawsuit over drinking water contaminated by PFOA and other fluorosurfactants. [14] [15] [16]

See also

Related Research Articles

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References

  1. 1 2 U.S. patent 3,574,791
  2. "Scotchgard vs Scotchguarding". Stain Protection Services. December 17, 2021. Retrieved June 1, 2023.
  3. Fredriksson, Felicia; Kärrman, Anna; Eriksson, Ulrika; Yeung, Leo WY. (2022). "Analysis and characterization of novel fluorinated compounds used in surface treatments products". Chemosphere. 302: 134720. doi: 10.1016/j.chemosphere.2022.134720 .
  4. Renner R (January 2006). "The long and the short of perfluorinated replacements". Environ. Sci. Technol. 40 (1): 12–3. doi: 10.1021/es062612a . PMID   16433328.
  5. 1 2 Betts, Kellyn S. (2007). "Perfluoroalkyl Acids: What is the Evidence Telling Us?". Environmental Health Perspectives. 115 (5): A250–A256. doi:10.1289/ehp.115-a250. PMC   1867999 . PMID   17520044.
  6. "ScotchgardTM Fabric Protector Safety Data Sheet". 3M. March 2, 2018. Retrieved February 22, 2021.
  7. Ullah, Aziz (October 2006). "The Fluorochemical Dilemma: What the PFOS/PFOA fuss is all about" (PDF). Cleaning & Restoration. ascr.org. Retrieved October 25, 2008.
  8. Boulanger B; Vargo JD; Schnoor JL; Hornbuckle KC (August 2005). "Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product". Environ. Sci. Technol. 39 (15): 5524–30. doi:10.1021/es050213u. PMID   16124283. Supporting Information (PDF).
  9. Stephen K. Ritter (January 2006). "Crystal Ball On The Environment: Detective work and expertise are used to evaluate environmental contaminants of emerging concern". Chemical & Engineering News. 84 (5): 37–40. doi:10.1021/cen-v084n049.p037.
  10. Lee, Jennifer 8. (April 15, 2003). "E.P.A. Orders Companies to Examine Effects of Chemicals". The New York Times. Retrieved May 15, 2009.
  11. "PFOS-PFOA Information: What is 3M Doing?". 3M. Archived from the original on September 22, 2008. Retrieved October 25, 2008.
  12. "3M Says It Will Stop Making Scotchgard". The New York Times. May 17, 2000. Retrieved July 30, 2022.
  13. "Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty" (Press release). Geneva: Stockholm Convention Secretariat. May 8, 2008.
  14. Reisch, Marc S. (February 26, 2018). "3M to pay $850 million to settle fluorosurfactants lawsuit". Chemical & Engineering News. Retrieved August 29, 2018.
  15. "3M must learn from its $850 million mistake". Star Tribune. Retrieved August 29, 2018.
  16. Kary, Tiffany; Cannon, Christopher (November 2, 2018). "Cancer-linked Chemicals Manufactured by 3M Are Turning Up in Drinking Water". Bloomberg News. Retrieved January 31, 2019.