{"id":9568,"date":"2019-06-13T08:00:15","date_gmt":"2019-06-13T14:00:15","guid":{"rendered":"https:\/\/www.ulprospector.com\/knowledge\/?p=9568"},"modified":"2019-08-09T07:54:25","modified_gmt":"2019-08-09T13:54:25","slug":"pc-get-a-reaction-with-urethane-coatings","status":"publish","type":"post","link":"https:\/\/ulprospector.ul.com\/9568\/pc-get-a-reaction-with-urethane-coatings\/","title":{"rendered":"Get a Reaction with Urethane Coatings"},"content":{"rendered":"<p><strong><em><img loading=\"lazy\" decoding=\"async\" class=\"alignright wp-image-9574 size-full\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/green-paint-and-brush-iStock-818972616-600x400.jpg\" alt=\"photo of a person painting - learn more about polyurethane coatings\" width=\"600\" height=\"400\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/green-paint-and-brush-iStock-818972616-600x400.jpg 600w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/green-paint-and-brush-iStock-818972616-600x400-300x200.jpg 300w\" sizes=\"(max-width: 600px) 100vw, 600px\" \/> Polyurethanes coatings <\/em><\/strong>have come a long way since their invention by Otto Bayer and coworkers in 1937. Depending on the choice of oligomeric and polymeric materials, these paints are used in a variety of demanding high performance applications due to their versatility. They can be hard or soft, flexible or rigid, resistant to chemicals and provide excellent adhesion.<\/p>\n<h3>Polyurethane properties and applications<\/h3>\n<ul>\n<li>Outstanding moisture and corrosion resistance<\/li>\n<li>Flexible primers and topcoats<\/li>\n<li>Weather resistance (aliphatic polyisocyanate with suitable durable polyol)<\/li>\n<li>Resistance to acid rain and other chemicals<\/li>\n<li>One component<\/li>\n<li>Two component<\/li>\n<li>Waterborne one component bake finishes<\/li>\n<li>100% solids<\/li>\n<li>Powder coatings<\/li>\n<li>Waterborne ambient cure two component finishes<\/li>\n<\/ul>\n<p>Polymeric and isocyanate prepolymer components include one or more isocyanate prepolymers and one or more polymeric or oligomeric components containing hydroxy functionality or other active hydrogen group. Isocyanates are <strong><em>reactive with functionalities<\/em><\/strong> which include:<\/p>\n<ul>\n<li>Hydroxy<\/li>\n<li>Amino<\/li>\n<li>Imino<\/li>\n<li>Ketimene<\/li>\n<li>Carboxyl (forms CO<sub>2<\/sub>)<\/li>\n<li>Urethanes<\/li>\n<li>Ureas<\/li>\n<li>Acetoacetylated resins<\/li>\n<\/ul>\n<p>The active hydrogen for exterior weatherable coatings is normally an aliphatic hydroxyl group in a polyester or acrylic polymer. Alcohols and phenols react with an isocyanate to form <strong><em>urethanes<\/em><\/strong>.<\/p>\n<hr \/>\n<h3>Need help finding polyurethane coatings?<\/h3>\n<p>Prospector can help speed along your research with technical datasheets and access to global equipment suppliers.<\/p>\n<h3><a href=\"https:\/\/www.ulprospector.com\/en\/na\/Coatings\/search?k=polyurethane&amp;st=31\" target=\"_blank\" rel=\"noopener noreferrer\">Search polyurethane coatings here<\/a><\/h3>\n<hr \/>\n<h3>Urethane reactions<\/h3>\n<p>In the following reaction, R<sup>1<\/sup> and R<sup>2<\/sup> can be aliphatic or aromatic.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9567\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/R1-R2-aliphatic-or-aromatic.jpg\" alt=\"R1-R2-aliphatic-or-aromatic formula - Learn more about polyurethane coatings\" width=\"800\" height=\"73\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/R1-R2-aliphatic-or-aromatic.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/R1-R2-aliphatic-or-aromatic-300x27.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/R1-R2-aliphatic-or-aromatic-768x70.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<p>The urethane reaction is reversible at higher temperatures. For baking systems such as those using blocked isocyanates, excessive bake temperature can result in embrittlement, color change and a decrease in moisture and corrosion resistance.<\/p>\n<p>As a general rule, reaction rates for urethane formation is in the following order:<\/p>\n<p><strong><em>primary hydroxyl &gt; secondary hydroxyl &gt; tertiary hydroxyl. <\/em><\/strong><em>The reverse reaction rate is the inverse of the forward reaction.<\/em> For example urethanes from tertiary hydroxyls are relatively unstable.<\/p>\n<p>Once formed, urethanes can react further with isocyanates to form <strong><em>allophanates<\/em><\/strong>:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9569\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/Allophonates.jpg\" alt=\"Allophonates formula - Learn more about polyurethane coatings\" width=\"800\" height=\"221\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/Allophonates.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/Allophonates-300x83.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/Allophonates-768x212.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<p>Other ambient cure reactions of an isocyanate and polyol follow:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9562\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/isocyanate-polyol.jpg\" alt=\"isocyanate-polyol - Learn more about polyurethane coatings\" width=\"800\" height=\"381\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/isocyanate-polyol.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/isocyanate-polyol-300x143.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/isocyanate-polyol-768x366.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<p>As illustrated above, the desired crosslinking reaction between a polyol and an isocyanate to form a polyurethane involves multiple <strong><em>competing reactions<\/em><\/strong>. For this reason, two-component formulations with polyol in one component and isocyanate in a second component are normally formulated with a <strong><em>10% or more stoichiometric excess<\/em><\/strong> of isocyanate to overcome competing reactions with moisture and other possible reactants.<\/p>\n<h3>Polyurethane catalysts<\/h3>\n<p><strong><em>Catalysts<\/em><\/strong> for polyurethanes include tin based carboxylates such as dibutyl tin dilaurate, dibutyl tin octoate or tertiary amines such a DABCO [N<sub>2<\/sub>(C<sub>2<\/sub>H<sub>4<\/sub>)<sub>3<\/sub>]. For toxicity concerns, there are also tin-free catalysts based on bismuth neodecanoate, bismuth 2-ethylhexanoate or other metal carboxylates.<\/p>\n<h3>Isocyanates and polyisocyanates<\/h3>\n<p>There are multiple <strong><em>aliphatic and aromatic polyisocyanates<\/em><\/strong> available for use in ambient cure two-component solvent born, 100% solid liquid or powder, as well as waterborne paints. <strong><em>Blocked isocyanates<\/em><\/strong> are used in single component baked coatings as they unblock at an elevated temperature to activate the isocyanate group. The reaction sequence is first unblocking and then addition. Polyurethanes formed from aromatic isocyanates are used primarily in primers and interior coatings due to poor light stability, but excellent moisture and corrosion resistance.<\/p>\n<p>Common aliphatic and aromatic polyisocyanate building blocks include:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-9563\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/polyisocyanate-building-blocks.jpg\" alt=\"polyisocyanate building blocks formulas - - Learn more about polyurethane coatings\" width=\"763\" height=\"355\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyisocyanate-building-blocks.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyisocyanate-building-blocks-300x140.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyisocyanate-building-blocks-768x357.jpg 768w\" sizes=\"(max-width: 763px) 100vw, 763px\" \/><\/p>\n<p>HDI and IPDI are used to synthesize higher molecular weight isocyanate prepolymers which may include isocyanurates, allophanates and uretdiones to improve hygiene, handling and weathering properties.<\/p>\n<p>Isocyanates can be blocked to form a stable material for use as a crosslinker in single component polyurethane coatings. <strong><em>Blocked isocyanates<\/em><\/strong> are used extensively in powder, waterborne and high solids baking finishes for coil primers, automotive coatings and electrodeposition coatings. Common blocking agents include 2-ethylhexanol, e-caprolactone, methyl ethyl ketoxime and 2-butoxy ethanol. When mixed with a polyol, blocked isocyanates are stable until they reach the unblocking temperature and then eliminate the blocking agent and react with the polyol to form a polyurethane.<\/p>\n<p><strong><em>Waterborne two component urethane<\/em><\/strong> coatings can be made using water dispersible isocyanates. Water dispersible IPDI or HDI based isocyanates are commercially available and are made by reacting a portion of the isocyanate groups with polyethylene glycol monoether. The polyisocyanate is then added into a separate dispersion containing the polyol to form separate dispersed particles that crosslink and form a film.<\/p>\n<h3>Iso-free technology<\/h3>\n<p>Isocyanate-based technology has come under increased scrutiny as exposure to isocyanates can cause asthma and other respiratory issues. Occupational asthma has overtaken asbestosis as the leading cause of new work-related lung disease. <strong><em>Isophorone free technology<\/em><\/strong> provides polyurethane formation without exposure to free isocyanate. In the last few years <strong><em>isofree<\/em><\/strong> technologies have emerged that do not utilize isocyanate crosslinkers to form\u00a0 a polyurethane and thus eliminate isocyanate exposure. Isofree 2K technology utilizing <strong><em>polycarbonate and polyaldehyde<\/em><\/strong> for example includes improved sprayable pot life and rapid cure and early hardness. Technologies that form polyurethanes without the use of an isocyanate crosslinker follow:<\/p>\n<ol>\n<li><strong>Hexamethoxy methyl melamine + Polycarbonate \u2192 Polyurethane<\/strong><\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9564\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/polyurethane.jpg\" alt=\"polyurethane formula - Learn more about polyurethane coatings\" width=\"800\" height=\"164\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane-300x62.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane-768x157.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<ol start=\"2\">\n<li><strong>Polycarbonate + Polyamine\u00a0\u2192 Polyurethane<\/strong><\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9565\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/polyurethane2.jpg\" alt=\"polyurethane formula - Learn more about polyurethane coatings\" width=\"800\" height=\"170\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane2.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane2-300x64.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane2-768x163.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<ol start=\"3\">\n<li><strong>Polycarbamate + Polyaldehyde \u2192 Polyurethane<\/strong><\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-9566\" src=\"https:\/\/ulprospector.ul.com\/media\/2019\/06\/polyurethane3.jpg\" alt=\"polyurethane formula - Learn more about polyurethane coatings\" width=\"800\" height=\"399\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane3.jpg 800w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane3-300x150.jpg 300w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2019\/06\/polyurethane3-768x383.jpg 768w\" sizes=\"(max-width: 800px) 100vw, 800px\" \/><\/p>\n<p>The formation of polyurethanes in reactions #1 and #2 are sluggish at room temperature, whereas the reaction rate of #3 that utilizes the <strong><em>crosslinking reaction of a polycarbonate and a polyaldehyde <\/em><\/strong>is more facile. Polyurethane formation by this reaction route provides a longer sprayable pot life and at the same time a faster reaction rate after application than that provided by the use of an isocyanate crosslinker.<\/p>\n<h3>Sources:<\/h3>\n<p>Prospector <a href=\"https:\/\/ulprospector.ul.com\/\" target=\"_blank\" rel=\"noopener noreferrer\">Knowledge Center<\/a> and <a href=\"https:\/\/www.ulprospector.com\/en\/na\/Coatings\/search?k=sealant&amp;st=31\" target=\"_blank\" rel=\"noopener noreferrer\">Search Engine<\/a><\/p>\n<p><a href=\"http:\/\/www.essentialchemicalindustry.org\/polymers\/polyurethane.html\" target=\"_blank\" rel=\"noopener noreferrer\">Polyurethanes.<\/a> (2017). The Essential Chemistry Industry &#8211; online.<\/p>\n<p>Mahendra, Vidhura. (2016). <a href=\"https:\/\/www.researchgate.net\/publication\/290436795_Foam_making_via_pine_resins\/figures?\" target=\"_blank\" rel=\"noopener noreferrer\">Foam making via pine resins<\/a>. 10.13140\/RG.2.1.2065.0004.<\/p>\n<p>Wikepedia. <a href=\"https:\/\/en.wikipedia.org\/wiki\/Polyurethane\" target=\"_blank\" rel=\"noopener noreferrer\">Polyurethane<\/a>.<\/p>\n<p>John Argyropoulos, Nahrain Kamber, David Pierce, Paul Popa, Yanxiang Li and Paul Foley. Dow <a href=\"http:\/\/msdssearch.dow.com\/PublishedLiteratureDOWCOM\/dh_0933\/0901b80380933b25.pdf?f\" target=\"_blank\" rel=\"noopener noreferrer\">Isocyanate Free Polyurethane Coatings \u2013 Fundamental Chemistry and Performance Attributes<\/a>, European Coatings Conference, April 21, 2015.<\/p>\n<p>Zeno W. Wicks Jr.,\u00a0Frank N. Jones,\u00a0Socrates Peter Pappas,\u00a0Douglas A. Wicks. (2007). Organic Coatings: Science and Technology, Third Edition.<\/p>\n<p>Wiley, Jones e.al. (2017) Organic Coatings, Science and Technology, Third Edition.<\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Polyurethanes coatings have come a long way since their invention by Otto Bayer and coworkers in 1937. Depending on the choice of oligomeric and polymeric materials, these paints are used in a variety of demanding high performance applications due to &hellip; <a href=\"https:\/\/ulprospector.ul.com\/9568\/pc-get-a-reaction-with-urethane-coatings\/\">Continued<\/a><\/p>\n","protected":false},"author":12,"featured_media":9574,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"episode_type":"","audio_file":"","podmotor_file_id":"","podmotor_episode_id":"","cover_image":"","cover_image_id":"","duration":"","filesize":"","filesize_raw":"","date_recorded":"","explicit":"","block":"","itunes_episode_number":"","itunes_title":"","itunes_season_number":"","itunes_episode_type":"","footnotes":""},"categories":[16],"tags":[],"ppma_author":[1249],"class_list":{"0":"post-9568","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-paint-coatings","8":"entry"},"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.4 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Get a Reaction with Urethane Coatings - Paint &amp; Coatings<\/title>\n<meta name=\"description\" content=\"Polyurethanes coatings are used in a variety of demanding high performance applications because of their desirable characteristics.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/ulprospector.ul.com\/9568\/pc-get-a-reaction-with-urethane-coatings\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Get a Reaction with Urethane Coatings - Paint &amp; Coatings\" \/>\n<meta property=\"og:description\" content=\"Polyurethanes coatings are in high demand because of their desirable characteristics. 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Lewarchik, President and CEO of Chemical Dynamics, LLC, brings 40 years of paint and coatings industry expertise to his role as a contributing author with the Prospector Knowledge Center. As a contributing writer, Ron pens articles on topics relevant to formulators in the coatings industry. He also serves as a consultant for the Prospector materials search engine, advising on issues related to optimization and organization materials within the database. Ron's company, Chemical Dynamics, LLC (www.chemicaldynamics.net), is a full-service paint and coatings firm specializing in consulting and product development based in Plymouth, Michigan. Since 2004, he has provided consulting, product development, contract research, feasibility studies, failure mode analysis and more for a wide range of clients, as well as their suppliers, customers and coaters. He has also served as an Adjunct Research Professor at the Coatings Research Institute of Eastern Michigan University. As such, Ron was awarded a sub-grant from the Department of Energy to develop energy-saving coating technology for architectural applications, as well as grants from private industry to develop low energy cure, low VOC compliant coatings. He taught courses on color and application of automotive top coats, cathodic electro-coat and surface treatment. His experience includes coatings for automotive, coil, architectural, industrial and product finishing. Previously, Ron was the Vice President of Industrial Research and Technology, as well as the Global Director of Coil Coating Technology for BASF (Morton International). During his fourteen-year tenure with the company, he developed innovative coil coating commercial products primarily for roofing, residential, commercial and industrial building, as well as industrial and automotive applications. He was awarded fifteen patents for new resin and coating formulas. From 1974 to 1990, Ron held positions with Desoto, Inc. and PPG Industries. He was the winner of two R&amp;D awards for coatings utilizing PVDF resins, developed the first commercial high solids automotive topcoat and was awarded 39 U.S. patents for a variety of novel technologies he developed. He holds a Masters in Physical Organic Chemistry from the University of Pittsburgh and subsequently studied Polymer Science at Carnegie Mellon University. Ron lives in Brighton, Michigan with his family. 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Lewarchik, President and CEO of Chemical Dynamics, LLC, brings 40 years of paint and coatings industry expertise to his role as a contributing author with the Prospector Knowledge Center. As a contributing writer, Ron pens articles on topics relevant to formulators in the coatings industry. He also serves as a consultant for the Prospector materials search engine, advising on issues related to optimization and organization materials within the database. Ron's company, Chemical Dynamics, LLC (www.chemicaldynamics.net), is a full-service paint and coatings firm specializing in consulting and product development based in Plymouth, Michigan. Since 2004, he has provided consulting, product development, contract research, feasibility studies, failure mode analysis and more for a wide range of clients, as well as their suppliers, customers and coaters. He has also served as an Adjunct Research Professor at the Coatings Research Institute of Eastern Michigan University. As such, Ron was awarded a sub-grant from the Department of Energy to develop energy-saving coating technology for architectural applications, as well as grants from private industry to develop low energy cure, low VOC compliant coatings. He taught courses on color and application of automotive top coats, cathodic electro-coat and surface treatment. His experience includes coatings for automotive, coil, architectural, industrial and product finishing. Previously, Ron was the Vice President of Industrial Research and Technology, as well as the Global Director of Coil Coating Technology for BASF (Morton International). During his fourteen-year tenure with the company, he developed innovative coil coating commercial products primarily for roofing, residential, commercial and industrial building, as well as industrial and automotive applications. He was awarded fifteen patents for new resin and coating formulas. From 1974 to 1990, Ron held positions with Desoto, Inc. and PPG Industries. He was the winner of two R&amp;D awards for coatings utilizing PVDF resins, developed the first commercial high solids automotive topcoat and was awarded 39 U.S. patents for a variety of novel technologies he developed. He holds a Masters in Physical Organic Chemistry from the University of Pittsburgh and subsequently studied Polymer Science at Carnegie Mellon University. Ron lives in Brighton, Michigan with his family. 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