Chemistry of Dimer Acid Production from Fatty Acids and the Structure–Property Relationships of Polyamides Made from These Dimer Acids

Abstract

While there is abundant literature on using a wide range of biomaterials to make polymers for various adhesive applications, most researchers have generally overlooked developing new adhesives from commercially available bio-based dimerized fatty acids. Some of the literature on the chemistry taking place during the clay-catalyzed dimerization of unsaturated fatty acids is generally misleading in that the mechanisms are not consistent with the structures of these dimers and a by-product isostearic acid. A selective acid-catalyzed interlayer model is much more logical than the widely accepted model of clay-catalyzed Diels–Alder reactions. The resulting dimers have a variety of linkages limiting large crystal formation either as oligomeric amides or polyamides. These highly aliphatic fatty acid dimers are used to make a wide range of hot melt polyamide adhesives. The specific structures and amounts of the diacids and diamines and their relative ratios have a big effect on the bio-based polyamide mechanical properties, but analysis of the structure–property relationships has seldom been attempted, since the data are mainly in the patent literature. The diacids derived from plant oils are valuable for making polyamides because of their very high bio-based content and highly tunable properties.