Nonoxynols

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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.

Contents

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 use in industrial and institutional cleaning, domestic cleaning, cosmetics and other applications including spermicides and in use as co-formulants in pesticides (except for pesticides where prior authorization was granted before July 17, 2003 in which effects of the restriction will not occur until date of their expiration) amounts equal to or exceeding 0.1% by weight, and limiting NPE residues on textile articles to 0.01% by weight, effective February 3, 2021. [5] [6] 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. [7] 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. [8] [9]

Related Research Articles

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<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined c. 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.

<span class="mw-page-title-main">Polyethylene glycol</span> Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.

<span class="mw-page-title-main">Nonylphenol</span> Chemical compound

Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).

<span class="mw-page-title-main">Polypropylene glycol</span> Chemical compound

Polypropylene glycol or polypropylene oxide is the polymer of propylene glycol. Chemically it is a polyether, and, more generally speaking, it's a polyalkylene glycol (PAG) H S Code 3907.2000. The term polypropylene glycol or PPG is reserved for polymer of low- to medium-range molar mass when the nature of the end-group, which is usually a hydroxyl group, still matters. The term "oxide" is used for high-molar-mass polymer when end-groups no longer affect polymer properties. Between 60 and 70% of propylene oxide is converted to polyether polyols by the process called alkoxylation.

<span class="mw-page-title-main">Triton X-100</span> Chemical compound

Triton X-100 is a nonionic surfactant that has a hydrophilic polyethylene oxide chain and an aromatic hydrocarbon lipophilic or hydrophobic group. The hydrocarbon group is a 4-(1,1,3,3-tetramethylbutyl)-phenyl group. Triton X-100 is closely related to IGEPAL CA-630, which might differ from it mainly in having slightly shorter ethylene oxide chains. As a result, Triton X-100 is slightly more hydrophilic than Igepal CA-630 thus these two detergents may not be considered functionally interchangeable for most applications.

Polysorbate 20 is a polysorbate-type nonionic surfactant formed by the ethoxylation of sorbitan monolaurate. Its stability and relative nontoxicity allows it to be used as a detergent and emulsifier in a number of domestic, scientific, and pharmacological applications. As the name implies, the ethoxylation process leaves the molecule with 20 repeat units of polyethylene glycol; in practice these are distributed across 4 different chains, leading to a commercial product containing a range of chemical species.

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<span class="mw-page-title-main">NP-40</span> Chemical compound

NP-40 is a commercially available detergent with CAS Registry Number 9016-45-9. NP-40 is an ethoxylated nonylphenol for non-ionic surfactants and can act as emulsifier and demulsifier agent.

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<span class="mw-page-title-main">Alkylphenol</span> Family of organic compounds

Alkylphenols are a family of organic compounds obtained by the alkylation of phenols. The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols" (LCAPs). Methylphenols and ethylphenols are also alkylphenols, but they are more commonly referred to by their specific names, cresols and xylenols.

<span class="mw-page-title-main">Defoamer</span> Chemical additive that reduces and hinders the formation of foam in liquids

A defoamer or an anti-foaming agent is a chemical additive that reduces and hinders the formation of foam in industrial process liquids. The terms anti-foam agent and defoamer are often used interchangeably. Strictly speaking, defoamers eliminate existing foam and anti-foamers prevent the formation of further foam. Commonly used agents are insoluble oils, polydimethylsiloxanes and other silicones, certain alcohols, stearates and glycols. The additive is used to prevent formation of foam or is added to break a foam already formed.

<span class="mw-page-title-main">Cetomacrogol 1000</span> Chemical compound

Cetomacrogol 1000 is the tradename for polyethylene glycol hexadecyl ether, which is nonionic surfactant produced by the ethoxylation of cetyl alcohol to give a material with the general formula HO(C2H4O)nC16H33. Several grades of this material are available depending on the level of ethoxylation performed, with repeat units (n) of polyethylene glycol varying between 2 and 20. Commercially it can be known as Brij 58 (when n=20) or Brij 56 (when n=10). Brij is a trademark of Croda International.

<span class="mw-page-title-main">Björn Borg (brand)</span>

Björn Borg AB is a Swedish apparel fashion brand named after the former professional tennis player of the same name. The company was formerly named World Brand Management (WBM), and has stores in seven European countries, with Sweden and the Netherlands being the most important ones. New markets are Germany and the United Kingdom.

Nonidet P-40 is a nonionic, non-denaturing detergent. Its official IUPAC name is octylphenoxypolyethoxyethanol.

Paint has four major components: pigments, binders, solvents, and additives. Pigments serve to give paint its color, texture, toughness, as well as determining if a paint is opaque or not. Common white pigments include titanium dioxide and zinc oxide. Binders are the film forming component of a paint as it dries and affects the durability, gloss, and flexibility of the coating. Polyurethanes, polyesters, and acrylics are all examples of common binders. The solvent is the medium in which all other components of the paint are dissolved and evaporates away as the paint dries and cures. The solvent also modifies the curing rate and viscosity of the paint in its liquid state. There are two types of paint: solvent-borne and water-borne paints. Solvent-borne paints use organic solvents as the primary vehicle carrying the solid components in a paint formulation, whereas water-borne paints use water as the continuous medium. The additives that are incorporated into paints are a wide range of things which impart important effects on the properties of the paint and the final coating. Common paint additives are catalysts, thickeners, stabilizers, emulsifiers, texturizers, biocides to fight bacterial growth, etc.

<span class="mw-page-title-main">DEG monobutyl ether</span> Chemical compound

Diethylene glycol butyl ether is an organic compound, one of several glycol ether solvents. It is a colorless liquid with a low odour and high boiling point. It is mainly used as a solvent for paints and varnishes in the chemical industry, household detergents, brewing chemicals and textile processing.

2-Hexoxyethanol, or 2-(hexyloxy)ethanol, is a glycol ether that has a chemical formula of C8H18O2.

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 Annex XVII - Conditions of restriction Entry 46". European Chemicals Agency (ECHA). 13 January 2016. Retrieved 11 April 2024.
  6. ↑ "EU REACH Annex XVII - Conditions of restriction Entry 46a". European Chemicals Agency (ECHA). 13 January 2016. Retrieved 11 April 2024.
  7. ↑ 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.
  8. ↑ Heimbuch, Jaymi (2011-08-23). "Big-Brand Clothing Found Laced with Toxic Chemicals". TreeHugger. Retrieved 2013-02-09.
  9. ↑ "Dirty Laundry 2: Hung Out to Dry | Greenpeace Africa". Greenpeace.org. 2011-08-23. Retrieved 2013-02-09.
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