| Enhancing the functionality of biobased polyester coating resins through modification with citric acid. | |
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MedLine Citation:
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PMID: 17994697 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Citric acid (CA) was evaluated as a functionality-enhancing monomer in biobased polyesters suitable for coating applications. Model reactions of CA with several primary and secondary alcohols and diols, including the 1,4:3,6-dianhydrohexitols, revealed that titanium(IV) n-butoxide catalyzed esterification reactions involving these compounds proceed at relatively low temperatures, often via anhydride intermediates. Interestingly, the facile anhydride formation from CA at temperatures around CA's melting temperature ( T m = 153 degrees C) proved to be crucial in modifying sterically hindered secondary hydroxyl end groups. OH-functional polyesters were reacted with CA in the melt between 150 and 165 degrees C, yielding slightly branched carboxylic acid functional materials with strongly enhanced functionality. The acid/epoxy curing reaction of the acid-functional polymers was simulated with a monofunctional glycidyl ether. Finally, the CA-modified polyesters were applied as coatings, using conventional cross-linking agents. The formulations showed rapid curing, resulting in chemically and mechanically stable coatings. These results demonstrate that citric acid can be applied in a new way, making use of its anhydride formation to functionalize OH-functional polyesters, which is an important new step toward fully biobased coating systems. |
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Authors:
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Bart A J Noordover; Robbert Duchateau; Rolf A T M van Benthem; Weihua Ming; Cor E Koning |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't Date: 2007-11-10 |
Journal Detail:
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Title: Biomacromolecules Volume: 8 ISSN: 1526-4602 ISO Abbreviation: Biomacromolecules Publication Date: 2007 Dec |
Date Detail:
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Created Date: 2007-12-11 Completed Date: 2008-02-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100892849 Medline TA: Biomacromolecules Country: United States |
Other Details:
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Languages: eng Pagination: 3860-70 Citation Subset: IM |
Affiliation:
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Laboratory of Polymer Chemistry, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Citric Acid
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chemical synthesis* Coated Materials, Biocompatible / chemical synthesis* Polyesters / chemical synthesis* Resins, Synthetic / chemical synthesis* |
| Chemical | |
Reg. No./Substance:
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0/Coated Materials, Biocompatible; 0/Polyesters; 0/Resins, Synthetic; 77-92-9/Citric Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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