Nonoxynols also known as nonaethylene glycol or polyethylene glycol nonyl phenyl ether are mixtures of

nonionic An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

s used as

detergent A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more ...

emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Altho ...

wetting agent Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

s or defoaming agents. The most commonly discussed compound

nonoxynol-9 Nonoxynol-9, sometimes abbreviated as N-9, is an organic compound that is used as a surfactant. It is a member of the nonoxynol family of nonionic surfactants. N-9 and related compounds are ingredients in various cleaning and cosmetic products ...

is a

spermicide Spermicide is a contraceptive substance that destroys sperm, inserted vaginally prior to intercourse to prevent pregnancy. As a contraceptive, spermicide may be used alone. However, the pregnancy rate experienced by couples using only spermicid ...

, formulated primarily as a component of

vaginal In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...

foams and creams. Nonoxynol was found to metabolize into free

nonylphenol 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, lub ...

when administered to lab animals. Arkopal-N60, with on average 6

ethylene glycol Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...

units is a related used

Production

Nonoxynols are produced by

ethoxylation 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. In the usual application, alcohols and phenols are converted i ...

alkylphenol 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 ...

s and vary in the number of repeating ethoxy (oxy-1,2-ethanediyl) groups resulting in Nonoxynol-4, Nonoxynol-7,

Nonoxynol-9 Nonoxynol-9, sometimes abbreviated as N-9, is an organic compound that is used as a surfactant. It is a member of the nonoxynol family of nonionic surfactants. N-9 and related compounds are ingredients in various cleaning and cosmetic products ...

, Nonoxynol-14, Nonoxynol-15, Nonoxynol-18,

Nonoxynol-40 NP-40 (also known as Tergitol-type NP-40 and nonyl phenoxypolyethoxylethanol) 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 ...

, 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

nonene Nonene is an alkene with the molecular formula C9H18. Many structural isomers are possible, depending on the location of the C=C double bond and the branching of the other parts of the molecule. Industrially, the most important nonenes are trimers ...

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.

Toxicity concerns

Concerns about the environmental impact of these compounds has increased since the 1990s. These surfactants have a mild to medium

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...

ic function. 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. On January 14, 2016, the

European Commission The European Commission (EC) is the executive of the European Union (EU). It operates as a cabinet government, with 27 members of the Commission (informally known as "Commissioners") headed by a President. It includes an administrative body o ...

amended existing restriction on nonylphenol ethoxylates (NPE) under the

Registration, Evaluation, Authorisation and Restriction of Chemicals Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) is a European Union regulation dating from 18 December 2006. REACH addresses the production and use of chemical substances, and their potential impacts on both human he ...

(REACH) legislation, limiting NPE residues on textile articles to 0.01% by weight, effective February 3, 2021. 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 Gothenburg (; abbreviated Gbg; sv, Göteborg ) is the second-largest city in Sweden, fifth-largest in the Nordic countries, and capital of the Västra Götaland County. It is situated by the Kattegat, on the west coast of Sweden, and has a p ...

( sv)'' reported finding high levels of the NPE in Björn Borg underwear. 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.

References

{{Reflist

External links

* J.K.G. Dondt, G. Gomppner, D. Richter (Eds) Soft matter: complex materials on mesoscopic scales - Schriften des Forschungszentrum Jülich, Vol. 10, 2002. Non-ionic surfactants Polyethers Phenol ethers Primary alcohols