Enhancing the functionality of biobased polyester coating resins through modification with citric acid

B.A.J. Noordover, R. Duchateau, R.A.T.M. Benthem, van, W. Ming, C.E. Koning

Research output: Contribution to journalArticleAcademicpeer-review

88 Citations (Scopus)

Abstract

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 (Tm = 153 °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 °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.
Original languageEnglish
Pages (from-to)3860-3870
JournalBiomacromolecules
Volume8
Issue number12
DOIs
Publication statusPublished - 2007

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