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href="#Comparison_to_waxes_and_resins"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Comparison to waxes and resins</span> </div> </a> <ul id="toc-Comparison_to_waxes_and_resins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a 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href="https://be.wikipedia.org/wiki/%D0%9F%D0%B0%D0%BA%D0%BE%D1%81%D1%82" title="Пакост – Belarusian" lang="be" hreflang="be" data-title="Пакост" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Oxidativt_h%C3%A6rdende_olie" title="Oxidativt hærdende olie – Danish" lang="da" hreflang="da" data-title="Oxidativt hærdende olie" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q70894304 mw-list-item" title=""><a href="https://de.wikipedia.org/wiki/Trocknendes_%C3%96l" title="Trocknendes Öl – German" lang="de" hreflang="de" data-title="Trocknendes Öl" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Aceite_secante" title="Aceite secante – Spanish" lang="es" hreflang="es" data-title="Aceite secante" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B1%D9%88%D8%BA%D9%86_%D8%AE%D8%B4%DA%A9%E2%80%8C%D8%B4%D9%88%D9%86%D8%AF%D9%87" title="روغن خشک‌شونده – Persian" lang="fa" hreflang="fa" data-title="روغن خشک‌شونده" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Siccativation" title="Siccativation – French" lang="fr" hreflang="fr" data-title="Siccativation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B1%B4%EC%84%B1%EC%9C%A0" title="건성유 – Korean" lang="ko" hreflang="ko" data-title="건성유" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%95%D5%AC%D5%AB%D6%86%D5%B6%D5%A5%D6%80" title="Օլիֆներ – Armenian" lang="hy" hreflang="hy" data-title="Օլիֆներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Olio_siccativo" title="Olio siccativo – Italian" lang="it" hreflang="it" data-title="Olio siccativo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9E%D0%BB%D0%B8%D1%84%D0%B0" title="Олифа – Kazakh" lang="kk" hreflang="kk" data-title="Олифа" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9E%D0%BB%D0%B8%D1%84%D0%B0" title="Олифа – Kyrgyz" lang="ky" hreflang="ky" data-title="Олифа" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E4%B9%BE%E6%80%A7%E6%B2%B9" title="乾性油 – Japanese" lang="ja" hreflang="ja" data-title="乾性油" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Alifmoy" title="Alifmoy – Uzbek" lang="uz" hreflang="uz" data-title="Alifmoy" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Oleje_schn%C4%85ce" title="Oleje schnące – Polish" lang="pl" hreflang="pl" data-title="Oleje schnące" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%93leo_secante" title="Óleo secante – Portuguese" lang="pt" hreflang="pt" data-title="Óleo secante" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9E%D0%BB%D0%B8%D1%84%D0%B0" title="Олифа – Russian" lang="ru" hreflang="ru" data-title="Олифа" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sd mw-list-item"><a href="https://sd.wikipedia.org/wiki/%D8%AE%D8%B4%DA%AA%D8%A7%D9%81%D8%B2%D9%87_%D8%AA%D9%8A%D9%84" title="خشڪافزه تيل – Sindhi" lang="sd" hreflang="sd" data-title="خشڪافزه تيل" data-language-autonym="سنڌي" data-language-local-name="Sindhi" class="interlanguage-link-target"><span>سنڌي</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kuivuva_%C3%B6ljy" title="Kuivuva öljy – Finnish" lang="fi" hreflang="fi" data-title="Kuivuva öljy" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv badge-Q70894304 mw-list-item" title=""><a href="https://sv.wikipedia.org/wiki/Torkande_olja" title="Torkande olja – Swedish" lang="sv" hreflang="sv" data-title="Torkande olja" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9E%D0%BB%D1%96%D1%84%D0%B0" title="Оліфа – Ukrainian" lang="uk" hreflang="uk" data-title="Оліфа" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%AE%D8%B4%DA%A9%D8%A7%D9%81%D8%B2%DB%81_%D8%AA%DB%8C%D9%84" title="خشکافزہ تیل – Urdu" lang="ur" hreflang="ur" data-title="خشکافزہ تیل" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%B9%BE%E6%80%A7%E6%B2%B9" title="乾性油 – Cantonese" lang="yue" hreflang="yue" data-title="乾性油" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B9%BE%E6%80%A7%E6%B2%B9" title="乾性油 – Chinese" lang="zh" hreflang="zh" data-title="乾性油" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q2549301#sitelinks-wikipedia" title="Edit interlanguage links" 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.sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media print{body.ns-0 .mw-parser-output .sidebar{display:none!important}}</style><table class="sidebar nomobile nowraplinks hlist"><tbody><tr><th class="sidebar-title"><a href="/wiki/Types_of_plant_oils" title="Types of plant oils">Plant oils</a></th></tr><tr><td class="sidebar-image"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Components_of_pure_linseed_oil_color..JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Components_of_pure_linseed_oil_color..JPG/145px-Components_of_pure_linseed_oil_color..JPG" decoding="async" width="145" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Components_of_pure_linseed_oil_color..JPG/218px-Components_of_pure_linseed_oil_color..JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Components_of_pure_linseed_oil_color..JPG/290px-Components_of_pure_linseed_oil_color..JPG 2x" data-file-width="3171" data-file-height="2763" /></a><figcaption></figcaption></figure><div class="sidebar-caption"><span style="font-size:85%;">Using linseed oil (a drying oil) and pigment for painting</span></div></td></tr><tr><th class="sidebar-heading"> Types</th></tr><tr><td class="sidebar-content"> <ul><li><a href="/wiki/Vegetable_oil" title="Vegetable oil">Vegetable oil</a> (<a href="/wiki/List_of_vegetable_oils" title="List of vegetable oils">list</a>)</li> <li><a href="/wiki/Maceration_(cooking)" title="Maceration (cooking)">Macerated oil</a> (<a href="/wiki/List_of_macerated_oils" class="mw-redirect" title="List of macerated oils">list</a>)</li> <li><a href="/wiki/Essential_oil" title="Essential oil">Essential oil</a> (<a href="/wiki/List_of_essential_oils" title="List of essential oils">list</a>)</li></ul></td> </tr><tr><th class="sidebar-heading"> Uses</th></tr><tr><td class="sidebar-content"> <ul><li><a class="mw-selflink selflink">Drying oil</a></li> <li><a href="/wiki/Oil_paint" title="Oil paint">Oil paint</a></li> <li><a href="/wiki/Cooking_oil" title="Cooking oil">Cooking oil</a></li> <li><a href="/wiki/Vegetable_oil_fuel" title="Vegetable oil fuel">Fuel</a></li> <li><a href="/wiki/Biodiesel" title="Biodiesel">Biodiesel</a></li></ul></td> </tr><tr><th class="sidebar-heading"> <a href="/wiki/Fatty_acid" title="Fatty acid">Components</a></th></tr><tr><td class="sidebar-content"> <ul><li><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated fat</a></li> <li><a href="/wiki/Monounsaturated_fat" title="Monounsaturated fat">Monounsaturated fat</a></li> <li><a href="/wiki/Polyunsaturated_fat" title="Polyunsaturated fat">Polyunsaturated fat</a></li> <li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li></ul></td> </tr><tr><td class="sidebar-navbar"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Vegetable_oils" title="Template:Vegetable oils"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vegetable_oils" title="Template talk:Vegetable oils"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vegetable_oils" title="Special:EditPage/Template:Vegetable oils"><abbr title="Edit this template">e</abbr></a></li></ul></div></td></tr></tbody></table> <p>A <b>drying oil</b> is an <a href="/wiki/Oil" title="Oil">oil</a> that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components <a href="/wiki/Cross-link" title="Cross-link">crosslink</a> (and hence, <a href="/wiki/Polymerize" class="mw-redirect" title="Polymerize">polymerize</a>) by the action of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> (not through the <a href="/wiki/Evaporation" title="Evaporation">evaporation</a> of water or other <a href="/wiki/Solvent" title="Solvent">solvents</a>). Drying oils are a key component of <a href="/wiki/Oil_paint" title="Oil paint">oil paint</a> and some <a href="/wiki/Varnish" title="Varnish">varnishes</a>. Some commonly used drying oils include <a href="/wiki/Linseed_oil" title="Linseed oil">linseed oil</a>, <a href="/wiki/Tung_oil" title="Tung oil">tung oil</a>, <a href="/wiki/Poppyseed_oil" title="Poppyseed oil">poppy seed oil</a>, <a href="/wiki/Perilla_oil" title="Perilla oil">perilla oil</a>, <a href="/wiki/Castor_oil" title="Castor oil">castor oil</a> and <a href="/wiki/Walnut_oil" title="Walnut oil">walnut oil</a>. The use of natural drying oils has declined over the past several decades, as they have been replaced by <a href="/wiki/Alkyd" title="Alkyd">alkyd</a> resins and other binders. </p><p>Since oxidation is the key to curing in these oils, those that are susceptible to chemical drying are often unsuitable for cooking, and are also highly susceptible to becoming <a href="/wiki/Rancidification" title="Rancidification">rancid</a> through autoxidation, the process by which fatty foods develop off-flavors.<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> Rags, cloth, and paper saturated with drying oils may <a href="/wiki/Spontaneous_combustion" title="Spontaneous combustion">spontaneously combust</a> (ignite) after a few hours as heat is released during the oxidation process. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemistry_of_the_drying_process">Chemistry of the drying process</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=1" title="Edit section: Chemistry of the drying process"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The "drying", hardening, or, more properly, <a href="/wiki/Curing_(chemistry)" title="Curing (chemistry)">curing</a> of oils is the result of <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a>, the addition of oxygen to an organic compound and the subsequent crosslinking. This process begins with an oxygen molecule (O<sub>2</sub>) in the air inserting into carbon-hydrogen (C-H) <a href="/wiki/Chemical_bond" title="Chemical bond">bonds</a> adjacent to one of the double bonds within the unsaturated fatty acid. The resulting <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxides</a> are susceptible to crosslinking reactions. Bonds form between neighboring fatty acid chains, resulting in a <a href="/wiki/Polymer" title="Polymer">polymer</a> network, often visible by formation of a skin-like film on samples. This polymerization results in stable films that, while somewhat elastic, do not flow or deform readily. Diene-containing fatty acid derivatives, such as those derived from linoleic acid, are especially prone to this reaction because they generate <a href="/wiki/Pentadienyl" class="mw-redirect" title="Pentadienyl">pentadienyl</a> radicals. Monounsaturated fatty acids, such as oleic acid, are slower to undergo drying because the <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> radical intermediates are less stable (i.e., slower to form).<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> </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:DryOilSteps.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/DryOilSteps.svg/260px-DryOilSteps.svg.png" decoding="async" width="260" height="379" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/DryOilSteps.svg/390px-DryOilSteps.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/DryOilSteps.svg/520px-DryOilSteps.svg.png 2x" data-file-width="2194" data-file-height="3201" /></a><figcaption>Simplified chemical reactions associated with cobalt-catalyzed drying process. In the first step, the <a href="/wiki/Diene" title="Diene">diene</a> undergoes autoxidation to give a <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxide</a>. In the second step, the hydroperoxide combines with another unsaturated side chain to generate a crosslink.</figcaption></figure></dd></dl> <p>The early stages of the drying process can be monitored by weight changes in an oil film. The film becomes heavier as it absorbs oxygen. <a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a>, for instance, increases in weight by 17 percent.<sup id="cite_ref-Apps_3-0" class="reference"><a href="#cite_note-Apps-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> As oxygen uptake ceases, the weight of the film declines as volatile compounds evaporate. As the oil ages, further transitions occur. A large number of the original ester bonds in the oil molecules undergo <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a>, releasing individual fatty acids. In the case of paints, some portion of these free fatty acids (FFAs) react with metals in the pigment, producing metal carboxylates. Together, the various non-cross-linking substances associated with the polymer network constitute the mobile phases. Unlike the molecules that are part of the network itself, they are capable of moving and diffusing within the film, and can be removed using heat or a solvent. The <a href="/wiki/Mobile_phase" class="mw-redirect" title="Mobile phase">mobile phase</a> may play a role in plasticizing paint films, preventing them from becoming too brittle. Carboxyl groups in the polymers of the stationary phase ionize, becoming negatively charged and form complexes with metal <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a> present in the pigment. The original network, with its nonpolar, covalent bonds, is replaced by an ionomeric structure, held together by ionic interactions. The structure of these ionomeric networks is not well understood. </p><p>Most drying oils rapidly increase in <a href="/wiki/Viscosity" title="Viscosity">viscosity</a> after heating in the absence of air. If the oil is subjected to raised temperatures for a long time, it will become a rubbery oil-insoluble substance.<sup id="cite_ref-Apps_3-1" class="reference"><a href="#cite_note-Apps-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Role_of_metal_catalysts">Role of metal catalysts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=2" title="Edit section: Role of metal catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The drying process is accelerated by certain metal salts, especially derivatives of <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>, <a href="/wiki/Manganese" title="Manganese">manganese</a>, or <a href="/wiki/Iron" title="Iron">iron</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2022)">citation needed</span></a></i>]</sup> In technical terms, these <a href="/wiki/Oil_drying_agent" title="Oil drying agent">oil drying agents</a> are <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> that function as <a href="/wiki/Homogeneous_catalyst" class="mw-redirect" title="Homogeneous catalyst">homogeneous catalysts</a>. These salts are derived from the carboxylates of <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>, such as <a href="/wiki/Naphthenic_acid" title="Naphthenic acid">naphthenic acids</a> to make the complexes oil-soluble. These catalysts speed up the reduction of the <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxide</a> intermediates. A series of addition reactions ensues. Each step produces additional free radicals, which then engage in further crosslinking. The process finally terminates when pairs of free radicals combine. The polymerization occurs over a period of days to years and renders the film dry to the touch. Premature action of the drying agents causes skinning of the paint, this undesirable process is suppressed by the addition of antiskinning agents such as <a href="/wiki/Methylethyl_ketone_oxime" title="Methylethyl ketone oxime">methylethyl ketone oxime</a>, which evaporate when the paint/oil is applied to a surface.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Constituents">Constituents</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=3" title="Edit section: Constituents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:ModelDryingOil.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/ModelDryingOil.png/300px-ModelDryingOil.png" decoding="async" width="300" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/ModelDryingOil.png/450px-ModelDryingOil.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/ModelDryingOil.png/600px-ModelDryingOil.png 2x" data-file-width="1715" data-file-height="682" /></a><figcaption>Representative triglyceride found in a drying oil. The triester is derived from three different unsaturated fatty acids, <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic</a> (top), <a href="/wiki/Alpha-Linolenic_acid" class="mw-redirect" title="Alpha-Linolenic acid">alpha-linolenic</a> (middle), and <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acids</a> (bottom). The order of drying rate is alpha-linolenic > linoleic > oleic acid, reflecting their degree of unsaturation.</figcaption></figure></dd></dl> <p>Drying oils consist of <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> tri<a href="/wiki/Ester" title="Ester">esters</a> of fatty acids. These esters are characterized by high levels of <a href="/wiki/Polyunsaturated_fat" title="Polyunsaturated fat">polyunsaturated</a> <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, especially <a href="/wiki/Alpha-linolenic_acid" class="mw-redirect" title="Alpha-linolenic acid">alpha-linolenic acid</a>. One common measure of the "siccative" (drying) property of oils is <a href="/wiki/Iodine_number" class="mw-redirect" title="Iodine number">iodine number</a>, which is an indicator of the number of <a href="/wiki/Double_bond" title="Double bond">double bonds</a> in the oil. Oils with an iodine number greater than 130 are considered drying, those with an iodine number of 115–130 are <a href="/wiki/Semi-drying_oil" title="Semi-drying oil">semi-drying</a>, and those with an iodine number of less than 115 are <a href="/wiki/Non-drying_oil" title="Non-drying oil">non-drying</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Comparison_to_waxes_and_resins">Comparison to waxes and resins</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=4" title="Edit section: Comparison to waxes and resins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Non-"drying" <a href="/wiki/Wax" title="Wax">waxes</a>, such as hard-film <a href="/wiki/Carnauba_wax" title="Carnauba wax">carnauba</a> or paste wax, and <a href="/wiki/Resin" title="Resin">resins</a>, such as <a href="/wiki/Dammar_gum" title="Dammar gum">dammar</a>, <a href="/wiki/Copal" title="Copal">copal</a>, and <a href="/wiki/Shellac" title="Shellac">shellac</a>, consist of long, spaghetti-like strands of hydrocarbon molecules, which interlace and compact but do not interconnect (<a href="/wiki/Crosslink" class="mw-redirect" title="Crosslink">crosslink</a>) in the manner of drying oils. Thus, waxes and resins remain <a href="/wiki/Solvent" title="Solvent">soluble</a> in their original solvent whereas a cured oil paint or varnish does not. A dissolved wax or resin is recovered unchanged after the <a href="/wiki/Evaporation" title="Evaporation">evaporation</a> of its solvent, but liquids that can dissolve cured drying oils, such as some <a href="/wiki/Paint_remover" class="mw-redirect" title="Paint remover">paint removers</a> do so by chemically changing them.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=5" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The ability of drying oils to form strong but flexible films is very useful in <a href="/wiki/Oil_paint" title="Oil paint">oil paints</a> and <a href="/wiki/Varnish" title="Varnish">varnishes</a>. In former times, <a href="/wiki/Walnut_oil" title="Walnut oil">walnut oil</a>, rich in <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a>, was used by painters. Nowadays, <a href="/wiki/Linseed_oil" title="Linseed oil">linseed oil</a> is used instead. </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=6" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Rags, cloth, and paper saturated with drying oils may <a href="/wiki/Spontaneous_combustion" title="Spontaneous combustion">combust spontaneously</a> (ignite) due to heat released during the curing process. This hazard is greater when oil-soaked materials are folded, bunched, or piled together, which allows heat to accumulate and accelerate the reaction. Precautions include: wetting rags with water and spreading them away from direct sunlight; keeping them in air-tight fireproof metal containers; immersing them in water inside air-tight metal containers designed for such applications; or storing them immersed in solvents in suitable closed containers.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2023)">citation needed</span></a></i>]</sup> </p><p>Leaving linseed-oil-soaked rags in a pile after refinishing woodwork was the cause of a 1991 fire in Philadelphia's <a href="/wiki/One_Meridian_Plaza" title="One Meridian Plaza">One Meridian Plaza</a>, a 38-story office building, which resulted in severe structural damage, and eventually the demolition of the building. </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=Drying_oil&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Blown_oil" title="Blown oil">Blown oil</a></li> <li><a href="/wiki/Danish_oil" title="Danish oil">Danish oil</a></li> <li><a href="/wiki/Fat_over_lean" title="Fat over lean">Fat over lean</a></li> <li><a href="/wiki/Linoleum" title="Linoleum">Linoleum</a></li> <li><a href="/wiki/Wood_finishing" title="Wood finishing">Wood finishing</a></li> <li><a href="/wiki/Varnish" title="Varnish">Varnish</a></li> <li><a href="/wiki/Non-drying_oil" title="Non-drying oil">Non-drying oil</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=Drying_oil&action=edit&section=8" 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="CITEREFUlrich_Poth2002" class="citation encyclopaedia cs1">Ulrich Poth (2002). "Drying Oils and Related Products". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a09_055">10.1002/14356007.a09_055</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Drying+Oils+and+Related+Products&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2002&rft_id=info%3Adoi%2F10.1002%2F14356007.a09_055&rft.isbn=978-3527306732&rft.au=Ulrich+Poth&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADrying+oil" 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">Ned A. Porter, Sarah E. Caldwell, Karen A. Mills "Mechanisms of free radical oxidation of unsaturated lipids" Lipids 1995, volume 30, Pages 277-290. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF02536034">10.1007/BF02536034</a></span> </li> <li id="cite_note-Apps-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Apps_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Apps_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFApps1958" class="citation book cs1">Apps, E. A. (1958). <i>Printing Ink Technology</i>. London: Leonard Hill [Books] Limited. p. 14.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Printing+Ink+Technology&rft.place=London&rft.pages=14&rft.pub=Leonard+Hill+%5BBooks%5D+Limited&rft.date=1958&rft.aulast=Apps&rft.aufirst=E.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADrying+oil" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=9" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>"Autoxidation". McGraw Hill Encyclopedia. 8th ed. 1997.</li> <li>Friedman, Ann, et al. "Painting". www.worldbookonline.com. 2006. 46 Stetson St. #5 Brookline, MA. 10 May 2006</li> <li>"History of Oil Paint". www.cyberlipid.org. 5 May 2006 <a rel="nofollow" class="external text" href="https://web.archive.org/web/20090916174446/http://www.cyberlipid.org/perox/oxid0011.htm">(archived 16 September 2009)</a>.</li> <li>van den Berg, Jorit D.J. "Mobile and Stationary Phases in Traditional Aged Oil Paint". www.amolf.nl 2002. MOLART. 8 May 2006</li> <li>Andés, Louis Edgar, <a rel="nofollow" class="external text" href="https://archive.org/details/dryingoilsboiled00anduoft"><i>Drying oils, boiled oil, and solid and liquid driers</i></a>. London: Scott, Greenwood & Co., 1901.</li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Drying_oil&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150515142422/http://www.sydneywoodturners.com.au/site/articles/finishing/oils.html">Tung and Linseed Oils</a> by Steven D. Russel</li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2549301#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Drying oils"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85039822">United States</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://www.bncatalogo.cl/F?func=direct&local_base=red10&doc_number=000000066">Chile</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007565359205171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; 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