{"id":10834,"date":"2022-09-14T08:05:20","date_gmt":"2022-09-14T14:05:20","guid":{"rendered":"https:\/\/www.ulprospector.com\/knowledge\/?p=10834"},"modified":"2023-06-21T07:27:22","modified_gmt":"2023-06-21T13:27:22","slug":"pc-fundamentals-of-polyester-resins","status":"publish","type":"post","link":"https:\/\/ulprospector.ul.com\/10834\/pc-fundamentals-of-polyester-resins\/","title":{"rendered":"Functional Polyester Resins for Coatings"},"content":{"rendered":"<p><img loading=\"lazy\" decoding=\"async\" class=\"alignright size-full wp-image-10835\" src=\"https:\/\/ulprospector.ul.com\/media\/2020\/08\/beaker-with-amber-liquid-iStock-172652594-600x400-1.jpg\" alt=\"Beaker with amber liquid - Fundamentals of Polyester Resins\" width=\"600\" height=\"400\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/beaker-with-amber-liquid-iStock-172652594-600x400-1.jpg 600w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/beaker-with-amber-liquid-iStock-172652594-600x400-1-300x200.jpg 300w\" sizes=\"(max-width: 600px) 100vw, 600px\" \/><\/p>\n<p>Original article date: Aug. 13, 2020<br \/>\nUpdated September 14, 2022<\/p>\n<p>Most polyester resins used in coatings are functional resins and, as a class, normally lower molecular weight than thermoplastic polyesters used in the packaging and plastics industry, such as <a href=\"https:\/\/www.ulprospector.com\/plastics\/en\/generics\/27?utm_source=knowledgecenter&amp;utm_medium=article&amp;utm_campaign=2022pe&amp;utm_term=functional&amp;utm_content=Lewarchik\" target=\"_blank\" rel=\"noopener\">polyethylene<\/a> (PE), <a href=\"https:\/\/www.ulprospector.com\/plastics\/en\/generics\/37\/classifications\/54?utm_source=knowledgecenter&amp;utm_medium=article&amp;utm_campaign=2022pe&amp;utm_term=functional&amp;utm_content=Lewarchik\" target=\"_blank\" rel=\"noopener\">polyethylene terephthalate<\/a> (PET) or <a href=\"https:\/\/www.ulprospector.com\/plastics\/en\/generics\/37\/classifications\/53?utm_source=knowledgecenter&amp;utm_medium=article&amp;utm_campaign=2022pe&amp;utm_term=functional&amp;utm_content=Lewarchik\" target=\"_blank\" rel=\"noopener\">polybutylene terephthalate<\/a> (PBT). Polyesters used in coatings applications are relatively low molecular weight and are amorphous, linear or branched and must be crosslinked to form useful films. As a class,\u00a0<strong><em>thermosetting polyes<\/em>ters<\/strong>\u00a0generally provide better metal adhesion, flexibility and thus impact resistance than thermosetting acrylics. However, the presence of ester linkages in the backbone of polyesters make them more prone to hydrolysis, accordingly proper selection of backbone monomers that provide steric hindrance to the ester group linkage, for example,\u00a0<strong><em>NPG<\/em><\/strong>\u00a0provides improved resistance to hydrolysis and weather resistance.<\/p>\n<h3>Polyester Synthesis<\/h3>\n<p>Historically, polyester synthesis was referred to as <strong><em>condensation polymerization<\/em><\/strong>\u00a0as the reaction of an alcohol group and a carboxyl group produces water.<\/p>\n<p>Polyester synthesis routes include:<\/p>\n<ul>\n<li>Step-growth polymerization<\/li>\n<li>The reaction of an ester with an alcohol<\/li>\n<li>The reaction of an anhydride and an alcohol<\/li>\n<li>Ring-opening polymerization of a lactone<\/li>\n<\/ul>\n<h3>Functional polyesters<\/h3>\n<p>Functional polyesters are available with a number of functionalities that include hydroxyl, carboxyl, carbamate, reactive unsaturation and a combination of one or more of these functionalities. By and large, most functional polyesters are <strong><em>hydroxyl functional polymers<\/em>. <\/strong>Functional polyesters are very versatile as they can be engineered to provide excellent properties, including mechanical, impact and flexibility, hardness, UV and chemical resistance. Applications for functional polyesters include automotive, aerospace, military, industrial, coil coating, and construction and include conventional solids, high solids, waterborne and powder coating. Formation of polyesters is commonly accomplished by\u00a0<strong><em>step-growth polymerization<\/em><\/strong>\u00a0of an alcohol with at least two hydroxy groups and a carboxylic acid with at least two carboxyl groups.<\/p>\n<h3>Conventional solids polyesters<\/h3>\n<p>Most polyester resins for<strong><em> conventional solids coatings <\/em><\/strong>comprise a diol and triol coupled with an aromatic dicarboxylic and aliphatic dicarboxylic acid or anhydride. The mole equivalency of dibasic acid to hydroxy polyol must be under one in order to provide a polyester resin with terminal hydroxyl groups and avoid a gel. If an excess of dibasic acid is used, the polyester is carboxy terminated for reaction with epoxy, melamine or 2-hydroxyalkyl amides. The ratio of linear aliphatic to aromatic dibasic acid controls the T<sub>g<\/sub> along with the selection of polyols effects the crosslink density, reactivity and the tendency of the resin to crystallize.<\/p>\n<p>When a diol (DD) reacts with a dibasic acid (CC) in equal molar amounts, the\u00a0<strong><em>molecular weight<\/em><\/strong>\u00a0builds gradually and is more readily controlled. The reactant in excess will have terminal groups of that reactant. For example:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-13623\" src=\"https:\/\/ulprospector.ul.com\/media\/2020\/08\/molecular-weight.jpg\" alt=\"molecular weight\" width=\"624\" height=\"71\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/molecular-weight.jpg 624w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/molecular-weight-300x34.jpg 300w\" sizes=\"(max-width: 624px) 100vw, 624px\" \/><\/p>\n<p>The average molecule will have terminal hydroxyl groups. Branched polyesters are made from mixtures of monomers that contain one or more monomers which have a functionality F &gt; 2. As the proportion of a monomer with\u00a0<strong><em>F (functionality)<\/em><\/strong>\u00a0<em>&gt; 2<\/em>\u00a0increases, the number average molecular weight increases and the reaction must be controlled to avoid gelation. A wide range of polyesters are in commercial use; for conventional polyesters cured with\u00a0<strong><em>melamine<\/em><\/strong>\u00a0or\u00a0<strong><em>isocyanate<\/em><\/strong>\u00a0prepolymers, the number average molecular weight is in the 2,000 to 6,000 range.<\/p>\n<p>Resins for conventional solids polyester coatings have a low level of carboxyl functionality coupled with a higher level of hydroxyl functionality to formulate a coating that crosslinks with a melamine crosslinker or blocked isocyanate for single component thermosetting baked coating. Alternatively, an isocyanate functional prepolymer can be used for two-component ambient cure urethane formulations. Examples of the use of conventional solids hydroxyl-functional polyesters include <strong><em>industrial and aerospace paints<\/em><\/strong>.<\/p>\n<h3>Hydroxyl-terminated linear polyester<\/h3>\n<p>Most polyester polyols for <strong><em>coil coatings<\/em><\/strong> are <strong><em>hydroxyl-terminated<\/em><\/strong> <strong><em>linear polyesters<\/em><\/strong> and are preferred to maximize flexibility. Painted coils are fabricated after painting rather than painted before the metal is formed. Accordingly, the coil coating process is often called prepaint. Most coil polyester resins have little <em>or no <\/em>trifunctional hydroxyl building blocks (for example, TMP) and utilize diols such as neopentyl glycol, propylene glycol, butane diol or 1,6 hexane diol. The diacids used in these types of resins can be a combination of linear aliphatic diacids along with an aromatic diacid or their dianhydride. Depending on their application, coil coatings are rapidly cured at high temperatures and formulated with an aminoplast crosslinker such as melamine or a blocked isocyanate.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13624\" src=\"https:\/\/ulprospector.ul.com\/media\/2020\/08\/Hydroxy-terminated-linear-polyester.png\" alt=\"Hydroxy terminated linear polyester\" width=\"650\" height=\"156\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/Hydroxy-terminated-linear-polyester.png 717w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/Hydroxy-terminated-linear-polyester-300x72.png 300w\" sizes=\"(max-width: 650px) 100vw, 650px\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignright wp-image-2863 size-full\" src=\"https:\/\/ulprospector.ul.com\/media\/2015\/08\/coil1.png\" alt=\"\" width=\"180\" height=\"181\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2015\/08\/coil1.png 180w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2015\/08\/coil1-150x150.png 150w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2015\/08\/coil1-30x30.png 30w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2015\/08\/coil1-60x60.png 60w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2015\/08\/coil1-90x90.png 90w\" sizes=\"(max-width: 180px) 100vw, 180px\" \/>The selection of polyester building blocks affects the architecture of the polyester molecule and many of the performance attributes such as flexibility, hardness, corrosion resistance, hydrolytic stability, exterior weatherability, chemical resistance, stain resistance and cure speed.<\/p>\n<h3>Carboxy-functional polyester<\/h3>\n<p>Carboxylic acid terminated functional polyesters most commonly contain TMA (see Table II) and IPA. Such carboxylic acid functional polyesters can be crosslinked with melamine or, more commonly, epoxy functional crosslinkers. For powder coating applications, higher T<sub>g<\/sub> carboxyl functional polyesters are based on TPA and IPA. Many so-called <strong><em>superpolyesters <\/em><\/strong>utilize IPA, NPG and other building blocks and can provide excellent hydrophobicity and light stability. Triglycidyl isocyanurate (oxirane) functional crosslinkers coupled with light and hydrolytic stable carboxylic functional polyesters provide very weatherable powder coatings.<\/p>\n<figure id=\"attachment_11789\" class=\"thumbnail wp-caption alignright\" style=\"width: 600px\"><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-11789\" src=\"https:\/\/ulprospector.ul.com\/media\/2021\/04\/Photo-Electrostatic-spray-application-of-powder-paint-on-metal-objects-HEADER-600x400-1.jpg\" alt=\"Electrostatic spray application of powder paint on metal objects\" width=\"600\" height=\"400\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2021\/04\/Photo-Electrostatic-spray-application-of-powder-paint-on-metal-objects-HEADER-600x400-1.jpg 600w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2021\/04\/Photo-Electrostatic-spray-application-of-powder-paint-on-metal-objects-HEADER-600x400-1-300x200.jpg 300w\" sizes=\"(max-width: 600px) 100vw, 600px\" \/><figcaption class=\"caption wp-caption-text\">Stock photo 98586439 of www.123RF.com<br \/>Electrostatic spray application of powder paint on metal objects<\/figcaption><\/figure>\n<h3>Carbamate functional polyester<\/h3>\n<p>These polyesters can be crosslinked with melamine to provide coatings with good light stability, acid resistance and mar resistance.<\/p>\n<h3>Unsaturated functional polyester<\/h3>\n<p>These polyesters generally contain maleic anhydride or fumaric acid as the source of their unsaturation, along with suitable acid functional and hydroxy functional building blocks and styrene. Although these resins are most known for their application in gel coats, they are sometimes formulated with peroxide and cobalt initiators in a two-component formulation primarily for gel coat applications.<\/p>\n<p>Table I &#8211; Effect of polyols on Polymer Properties:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-13626\" src=\"https:\/\/ulprospector.ul.com\/media\/2020\/08\/Effects-of-polyols.jpg\" alt=\"Effect of polyols on Polymer Properties\" width=\"641\" height=\"377\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/Effects-of-polyols.jpg 641w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/Effects-of-polyols-300x176.jpg 300w\" sizes=\"(max-width: 641px) 100vw, 641px\" \/><\/p>\n<p>Table II \u2013 Effect of acid functional monomers on Polymer Proper\u00ad\u00adties:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-13625\" src=\"https:\/\/ulprospector.ul.com\/media\/2020\/08\/effects-of-acid-functional-monomers.jpg\" alt=\"Effect of acid functional monomers on Polymer Properties\" width=\"650\" height=\"362\" srcset=\"https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/effects-of-acid-functional-monomers.jpg 650w, https:\/\/ulprospector.ul.com\/wp-content\/uploads\/2020\/08\/effects-of-acid-functional-monomers-300x167.jpg 300w\" sizes=\"(max-width: 650px) 100vw, 650px\" \/><\/p>\n<p>As Tables I and II illustrate, proper selection of co-reactant monomers can provide a range of performance characteristics to provide an array of performance attributes such as<\/p>\n<ul>\n<li><strong>hydrolytic stability<\/strong>\u00a0(NPG, Sebacic, CHDA)<\/li>\n<li><strong>exterior weathering<\/strong>\u00a0(NPG, BEPD, TMP, TME, HHPA, IPA)<\/li>\n<li><strong>hardness\u00a0<\/strong>(NPG, TME, TME, CHDM, TA)<\/li>\n<li><strong>flexibility\u00a0<\/strong>(AA, AzA, Seb, CHDA, TA, CDO)<\/li>\n<\/ul>\n<p>Desired performance can be achieved through the proper selection of a blend of monomers coupled with the selection of the polymer architecture to meet film performance properties.<\/p>\n<p><strong>Resources<\/strong><\/p>\n<ul>\n<li>Organic Coatings, Science and Technology, Frank N. Jones et al., Wiley &amp; Sons, 2017<\/li>\n<li><a href=\"http:\/\/www.ulprospector.com\/?st=31\" target=\"_blank\" rel=\"noopener\">Prospector<\/a> Knowledge Center<\/li>\n<li>Prospector Raw Materials for coatings<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Original article date: Aug. 13, 2020 Updated September 14, 2022 Most polyester resins used in coatings are functional resins and, as a class, normally lower molecular weight than thermoplastic polyesters used in the packaging and plastics industry, such as polyethylene &hellip; <a href=\"https:\/\/ulprospector.ul.com\/10834\/pc-fundamentals-of-polyester-resins\/\">Continued<\/a><\/p>\n","protected":false},"author":12,"featured_media":10835,"comment_status":"closed","ping_status":"closed","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-10834","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>Functional Polyester Resins for Coatings - Prospector Knowledge Center<\/title>\n<meta name=\"description\" content=\"Polyester coatings are a large portion of the construction, automotive and aerospace markets. 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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. Contact Ron via email\u00a0or through his company\u2019s web site at www.chemicaldynamics.net to learn more about his consulting services\u2026\",\"sameAs\":[\"https:\\\/\\\/ulprospector.ul.com\"],\"url\":\"https:\\\/\\\/ulprospector.ul.com\\\/author\\\/ron-lewarchik\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Functional Polyester Resins for Coatings - Prospector Knowledge Center","description":"Polyester coatings are a large portion of the construction, automotive and aerospace markets. 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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. Contact Ron via email\u00a0or through his company\u2019s web site at www.chemicaldynamics.net to learn more about his consulting services\u2026","sameAs":["https:\/\/ulprospector.ul.com"],"url":"https:\/\/ulprospector.ul.com\/author\/ron-lewarchik\/"}]}},"authors":[{"term_id":1249,"user_id":12,"is_guest":0,"slug":"ron-lewarchik","display_name":"Ron Lewarchik","avatar_url":"https:\/\/ulprospector.ul.com\/media\/2014\/05\/Ron-Lewarchik_avatar_1399393591-96x96.png","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/posts\/10834","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/users\/12"}],"replies":[{"embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/comments?post=10834"}],"version-history":[{"count":0,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/posts\/10834\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/media\/10835"}],"wp:attachment":[{"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/media?parent=10834"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/categories?post=10834"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/tags?post=10834"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/ulprospector.ul.com\/wp-json\/wp\/v2\/ppma_author?post=10834"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}