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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:204px;max-width:204px"><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:HALSgeneric.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/HALSgeneric.png/200px-HALSgeneric.png" decoding="async" width="200" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/HALSgeneric.png/300px-HALSgeneric.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/HALSgeneric.png/400px-HALSgeneric.png 2x" data-file-width="1410" data-file-height="1324" /></a></span></div><div class="thumbcaption">Partial structure of a typical hindered amine light stabilizer</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:LMW-HA(L)S-1_100.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/LMW-HA%28L%29S-1_100.svg/200px-LMW-HA%28L%29S-1_100.svg.png" decoding="async" width="200" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/LMW-HA%28L%29S-1_100.svg/300px-LMW-HA%28L%29S-1_100.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/57/LMW-HA%28L%29S-1_100.svg/400px-LMW-HA%28L%29S-1_100.svg.png 2x" data-file-width="243" data-file-height="78" /></a></span></div><div class="thumbcaption">Example structure of a commercial HAL</div></div></div></div></div> <p><b>Hindered amine light stabilizers</b> (<b>HALS</b>) are chemical compounds containing an <a href="/wiki/Amine" title="Amine">amine</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a> that are used as <a href="/wiki/Polymer_stabilizers" class="mw-redirect" title="Polymer stabilizers">stabilizers</a> in plastics and polymers.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> These compounds are typically derivatives of <a href="/wiki/Tetramethylpiperidine" class="mw-redirect" title="Tetramethylpiperidine">tetramethylpiperidine</a> and are primarily used to protect the polymers from the effects of <a href="/wiki/Photo-oxidation_of_polymers" title="Photo-oxidation of polymers">photo-oxidation</a>; as opposed to other forms of <a href="/wiki/Polymer_degradation" title="Polymer degradation">polymer degradation</a> such as <a href="/wiki/Ozonolysis" title="Ozonolysis">ozonolysis</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> They are also increasingly being used as thermal stabilizers,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> particularly for low and moderate level of heat, however during the high temperature processing of polymers (e.g. <a href="/wiki/Injection_moulding" title="Injection moulding">injection moulding</a>) they remain less effective than traditional phenolic antioxidants.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hindered_amine_light_stabilizers&action=edit&section=1" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>HALS do not absorb UV radiation, but act to inhibit degradation of the polymer by continuously and cyclically removing <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> that are produced by photo-oxidation of the polymer. The overall process is sometimes referred to as the <b>Denisov cycle</b>, after Evguenii T. Denisov<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and is exceedingly complex.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Broadly, HALS react with the initial polymer peroxy radical (ROO•) and alkyl polymer radicals (R•) formed by the reaction of the polymer and oxygen, preventing further radical oxidation. By these reactions HALS are oxidised to their corresponding <a href="/wiki/Aminoxyl_radical" class="mw-redirect" title="Aminoxyl radical">aminoxyl radicals</a> (R<sub>2</sub>NO• c.f. <a href="/wiki/TEMPO" title="TEMPO">TEMPO</a>), however they are able to return to their initial amine form via a series of additional radical reactions. HALS's high efficiency and longevity are due to this cyclic process wherein the HALS are regenerated rather than consumed during the stabilization process. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:UV-Stabilisator-Nitroxyradikal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/UV-Stabilisator-Nitroxyradikal.png/500px-UV-Stabilisator-Nitroxyradikal.png" decoding="async" width="500" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/UV-Stabilisator-Nitroxyradikal.png/750px-UV-Stabilisator-Nitroxyradikal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/3/36/UV-Stabilisator-Nitroxyradikal.png 2x" data-file-width="832" data-file-height="248" /></a><figcaption>Initial reaction of a HAL with a polymer peroxy radical: this step stabilizes the polymer and converts the HAL to its aminoxyl form</figcaption></figure> <p>The structure of the HALS makes them resistant to side reactions. The use of a hindered amine possessing no alpha-hydrogens prevents the HALS being converted into a <a href="/wiki/Nitrone" title="Nitrone">nitrone</a> species and piperidines are resistant to intramolecular <a href="/wiki/Cope_reaction" title="Cope reaction">Cope reactions</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In commercial HALS the reactive piperidine group is usually bonded to bulky chemical scaffold, in order to reduce its volatility during the melt processing of plastic. </p> <div class="mw-heading mw-heading2"><h2 id="Application">Application</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hindered_amine_light_stabilizers&action=edit&section=2" title="Edit section: Application"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Even though HALS are extremely effective in <a href="/wiki/Polyolefin" title="Polyolefin">polyolefins</a>, <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> and <a href="/wiki/Polyurethane" title="Polyurethane">polyurethane</a>, they are ineffective in <a href="/wiki/Polyvinyl_chloride" title="Polyvinyl chloride">polyvinyl chloride</a> (PVC). It is thought that their ability to form nitroxyl radicals is disrupted due them being readily protonated by <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">HCl</a> released by <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> of PVC.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="Your explanation here (May 2018)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hindered_amine_light_stabilizers&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/BTMPS" title="BTMPS">BTMPS</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hindered_amine_light_stabilizers&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFZweifelMaierSchiller2009" class="citation book cs1">Zweifel, Hans; Maier, Ralph D.; Schiller, Michael (2009). <i>Plastics additives handbook</i> (6th ed.). Munich: Hanser. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-446-40801-2" title="Special:BookSources/978-3-446-40801-2"><bdi>978-3-446-40801-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Plastics+additives+handbook&rft.place=Munich&rft.edition=6th&rft.pub=Hanser&rft.date=2009&rft.isbn=978-3-446-40801-2&rft.aulast=Zweifel&rft.aufirst=Hans&rft.au=Maier%2C+Ralph+D.&rft.au=Schiller%2C+Michael&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHindered+amine+light+stabilizers" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPieter_Gijsman2010" class="citation book cs1">Pieter Gijsman (2010). "Photostabilisation of Polymer Materials". In Norman S. Allen (ed.). <i>Photochemistry and Photophysics of Polymer Materials Photochemistry</i>. 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"A review on the mechanism of action and applicability of Hindered Amine Stabilizers". <i>Polymer Degradation and Stability</i>. <b>145</b>: 2–10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.polymdegradstab.2017.05.012">10.1016/j.polymdegradstab.2017.05.012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Polymer+Degradation+and+Stability&rft.atitle=A+review+on+the+mechanism+of+action+and+applicability+of+Hindered+Amine+Stabilizers&rft.volume=145&rft.pages=2-10&rft.date=2017-11&rft_id=info%3Adoi%2F10.1016%2Fj.polymdegradstab.2017.05.012&rft.aulast=Gijsman&rft.aufirst=Pieter&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHindered+amine+light+stabilizers" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGenslerPlummerKauschKramer2000" class="citation journal cs1">Gensler, R; Plummer, C.J.G; Kausch, H.-H; Kramer, E; Pauquet, J.-R; Zweifel, H (February 2000). "Thermo-oxidative degradation of isotactic polypropylene at high temperatures: phenolic antioxidants versus HAS". <i>Polymer Degradation and Stability</i>. <b>67</b> (2): 195–208. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0141-3910%2899%2900113-5">10.1016/S0141-3910(99)00113-5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Polymer+Degradation+and+Stability&rft.atitle=Thermo-oxidative+degradation+of+isotactic+polypropylene+at+high+temperatures%3A+phenolic+antioxidants+versus+HAS&rft.volume=67&rft.issue=2&rft.pages=195-208&rft.date=2000-02&rft_id=info%3Adoi%2F10.1016%2FS0141-3910%2899%2900113-5&rft.aulast=Gensler&rft.aufirst=R&rft.au=Plummer%2C+C.J.G&rft.au=Kausch%2C+H.-H&rft.au=Kramer%2C+E&rft.au=Pauquet%2C+J.-R&rft.au=Zweifel%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHindered+amine+light+stabilizers" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDenisov1991" class="citation journal cs1">Denisov, E.T. 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"Clarifying the Mechanism of the Denisov Cycle: How do Hindered Amine Light Stabilizers Protect Polymer Coatings from Photo-oxidative Degradation?". <i>Macromolecules</i>. <b>43</b> (10): 4573–4583. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010MaMol..43.4573H">2010MaMol..43.4573H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fma100453d">10.1021/ma100453d</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/1885%2F59767">1885/59767</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Macromolecules&rft.atitle=Clarifying+the+Mechanism+of+the+Denisov+Cycle%3A+How+do+Hindered+Amine+Light+Stabilizers+Protect+Polymer+Coatings+from+Photo-oxidative+Degradation%3F&rft.volume=43&rft.issue=10&rft.pages=4573-4583&rft.date=2010-05-25&rft_id=info%3Ahdl%2F1885%2F59767&rft_id=info%3Adoi%2F10.1021%2Fma100453d&rft_id=info%3Abibcode%2F2010MaMol..43.4573H&rft.aulast=Hodgson&rft.aufirst=Jennifer+L.&rft.au=Coote%2C+Michelle+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHindered+amine+light+stabilizers" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarchSmith2007" class="citation book cs1">March, Jerry; Smith, Michael B. 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Wiley-Interscience. p. 1525. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=March%27s+advanced+organic+chemistry%3A+reactions%2C+mechanisms%2C+and+structure.&rft.pages=1525&rft.edition=6th.&rft.pub=Wiley-Interscience&rft.date=2007-01-16&rft.isbn=978-0-471-72091-1&rft.aulast=March&rft.aufirst=Jerry&rft.au=Smith%2C+Michael+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHindered+amine+light+stabilizers" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Hindered_amine_light_stabilizers&oldid=1246940647">https://en.wikipedia.org/w/index.php?title=Hindered_amine_light_stabilizers&oldid=1246940647</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Amines" title="Category:Amines">Amines</a></li><li><a href="/wiki/Category:Plastics_additives" title="Category:Plastics additives">Plastics additives</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_May_2018" title="Category:Articles with unsourced statements from May 2018">Articles with unsourced statements from May 2018</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 21 September 2024, at 23:24<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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