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Quaternary ammonium cation
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===Fabric softeners and hair conditioners=== In the 1950s, [[distearyldimethylammonium chloride]] (DHTDMAC), was introduced as a [[fabric softener]]. This compound was discontinued because the cation biodegrades too slowly. Contemporary fabric softeners are based on salts of quaternary ammonium cations where the fatty acid is linked to the quaternary center via ester linkages; these are commonly referred to as [[betaine]]-esters or ester-quats and are susceptible to degradation, e.g., by [[hydrolysis]].<ref>{{cite journal| vauthors = Hellberg PE, Bergström K, Holmberg K |title=Cleavable surfactants|journal= Journal of Surfactants and Detergents|date=January 2000|volume=3|issue=1|pages=81–91|doi=10.1007/s11743-000-0118-z|s2cid=195343430}}</ref> Characteristically, the cations contain one or two long [[alkyl]] chains derived from fatty acids linked to an [[ethoxylate]]d ammonium salt.<ref>{{cite web |url=http://www.henkelconsumerinfo.com |title=Henkel Consumer Info |publisher=Henkelconsumerinfo.com |access-date=2009-06-04 |archive-url=https://web.archive.org/web/20191018103004/http://www.henkelconsumerinfo.com/products/ |archive-date=2019-10-18 |url-status=dead }}</ref> Other cationic compounds can be derived from [[imidazolium]], [[Guanidinium cation|guanidinium]], substituted amine salts, or quaternary [[alkoxy]] ammonium salts.<ref name=Ullmann>{{Ullmann| vauthors = Smulders E, Sung E |title=Laundry Detergents, 2. Ingredients and Products|doi=10.1002/14356007.o15_013}}</ref> <gallery caption="Cationic surfactants used as fabric softeners" widths="220px" heights="100px"> File:C18x2Me2Cl.png|[[Distearyldimethylammonium chloride]], an early generation [[fabric softener]] with low [[biodegradability]] that was phased out. File:Redrawn diesterquat salt (methanesulfonate anion) related to fabric softeners.png|Another diesterquat, a contemporary fabric softener. File:AltDiesterquatCl.png|Diethyl ester dimethyl ammonium chloride used as a fabric softener. File:DiesterCl.png|Another diesterquat used as a fabric softener. </gallery> The antistatic qualities that make quaternary ammonium salts useful as fabric softeners also make them useful in [[hair conditioner]]s and [[shampoo]]s.<ref>{{CPID|id=1000|name=Distearyldimonium chloride}}</ref> The idea was pioneered by [[Henkel]] with a 1984 patent.<ref>{{cite web |title=Quaternary ammonium compound hair conditioners US4744977 |url=https://patents.google.com/patent/US4744977 |website=Google Patents |language=en |date=14 November 1985}}</ref> Examples include [[cetrimonium chloride]] and [[behentrimonium chloride]].<ref>{{cite web | url = http://www.naturallycurly.com/curlreading/curly-q-a/curlchemist-what-is-cetrimonium-chloride | title = What is cetrimonium chloride? | archive-url = https://web.archive.org/web/20120304041725/http://www.naturallycurly.com/curlreading/curly-q-a/curlchemist-what-is-cetrimonium-chloride | archive-date=2012-03-04 | work = naturallycurly.com | date = November 2007 }}</ref>
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