Nonoxynols

Nonoxynols also known as nonaethylene glycol or polyethylene glycol nonyl phenyl ether are mixtures of nonionic surfactants used as detergents, emulsifiers, wetting agents or defoaming agents. The most commonly discussed compound nonoxynol-9 is a spermicide, formulated primarily as a component of vaginal foams and creams. Nonoxynol was found to metabolize into free nonylphenol when administered to lab animals.[1] Arkopal-N60, with on average 6 ethylene glycol units is a related used surfactant.

Production

Nonoxynols are produced by ethoxylation of alkylphenols and vary in the number of repeating ethoxy (oxy-1,2-ethanediyl) groups resulting in Nonoxynol-4, Nonoxynol-7, Nonoxynol-9, Nonoxynol-14, Nonoxynol-15, Nonoxynol-18, Nonoxynol-40, Nonoxynol-30 and Nonoxynol-50. Other synonyms are polyethylene glycol (PEG)-7 Nonyl phenyl ether, PEG-14 Nonyl phenyl ether, PEG-18 Nonyl phenyl ether and PEG-50 Nonyl phenyl ether. The precursor nonylphenol is derived from phenol and a mixture of nonenes.

Use

Nonoxynols have been used as detergents, emulsifiers and wetting agents in cosmetics, including hair products, and defoaming agents. Only nonoxynol-9 with 9 repeating ethoxy groups, has been used as a spermaticide, for vaginal foams and creams, and on condoms.[2]

Toxicity concerns

Concerns about the environmental impact of these compounds has increased since the 1990s. These surfactants have a mild to medium estrogenic function.[3] Consequently, this class of detergents has been effectively restricted for commercial "down-the-drain" applications in Europe, and these compounds are no longer used by U.S. laundry manufacturers.[4] On January 14, 2016, the European Commission amended existing restriction on nonylphenol ethoxylates (NPE) under the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) legislation, limiting NPE residues on textile articles to 0.01% by weight, effective February 3, 2021.[5] Previously, the use of NPE was forbidden within the EU, but there was no limit on the level of NPE residue on imported articles.

On 13 August 2008, the Swedish newspaper Göteborg Posten (sv) reported finding high levels of the NPE in Björn Borg underwear.[6] A 2011 investigation found residual levels of NPE in samples of clothing from 14 brands sold in the U.S., including Adidas, Uniqlo, Calvin Klein, H&M, Abercrombie & Fitch, Lacoste, Converse and Ralph Lauren.[7][8]

References
  1. Sonnenschein, Carlos, and Ana M. Soto. "An Updated Review of Environmental Estrogen and Androgen Mimics and Antagonists." The Journal of Steroid Biochemistry and Molecular Biology 65.1-6 (1998): 143-50.
  2. Substance Name: Nonoxynols Toxnet, U.S. National Library of Medicine, accessdate 14 March 2015
  3. Comparison of protein expression in plasma from nonylphenol and bisphenol A-exposed Atlantic cod (Gadus morhua) and turbot (Scophthalmus maximus) by use of SELDI-TOF. Larsen Bodil K; Bjornstad Anne; Sundt Rolf C; Taban Ingrid C; Pampanin Daniela M; Andersen Odd Ketil International Research Institute of Stavanger (IRIS) AS, Mekjarvik 12, N-4070 Randaberg, Norway Aquatic toxicology (Amsterdam, Netherlands) (2006), 78 Suppl 1 S25-33.
  4. "Going green", cover story in Chemical and Engineering Letters, vol. 85, No. 5, January 2007
  5. "EU REACH: New Restriction of NPE in Textile Articles 04/02/16". Bureau Veritas Solutions and Services. 4 February 2016. Retrieved 25 June 2017.
  6. Ekstrand, Lena (13 August 2008). "Skyhöga halter av miljögift. Det blev resultatet när GP Konsument lät analysera Björn Borg-kalsonger. Giftet är förbjudet inom EU, men tillåtet i importerade textilier". Göteborg Posten. Retrieved 25 June 2017.
  7. Heimbuch, Jaymi (2011-08-23). "Big-Brand Clothing Found Laced with Toxic Chemicals". TreeHugger. Retrieved 2013-02-09.
  8. "Dirty Laundry 2: Hung Out to Dry | Greenpeace Africa". Greenpeace.org. 2011-08-23. Retrieved 2013-02-09.
  • J.K.G. Dondt, G. Gomppner, D. Richter (Eds) Soft matter: complex materials on mesoscopic scales - Schriften des Forschungszentrum Jülich, Vol. 10, 2002.
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