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Abstract
Recently, itaconic acid has drawn considerable attention as a novel radical-curing building block for polyester resins. These bio-based materials have been used in thermal, as well as ultra violet (UV) curing applications, such as printing inks or coatings. Poly(ester amide)s from itaconic acid could be very interesting, as the amide group could alter the properties of the resins as well as cured materials. However, standard polycondensation reactions with diamines are not possible with itaconic acid as the amines preferably react via an aza-Michael addition at the α,β-unsaturated double bond. Therefore, alternative and more elaborate synthetic strategies have to be developed. Herein, we present two different synthetic strategies to poly(ester amide)s from itaconic acid that circumvent the addition reaction of the amines. This is in both cases done by a pre-reaction to form stable amide building blocks that are then reacted with itaconic acid or polyesters derived thereof. The structural composition and the properties of the resin are characterized, and the UV-curing reactivity is examined. All properties are compared to corresponding polyesters from itaconic acid.
Highlights
Over the last decade, immense research efforts have been undertaken to implement bio-based monomers as suitable alternative building blocks in polymeric materials [1,2,3,4]
As discussed in the introduction, the biggest challenge in the synthesis of unsaturated poly(ester amides) derived from itaconic acid is the undesired aza-Michael addition of the diamine at the α,β-unsaturated double bond of the itaconic acid. To solve this synthetic problem, two different strategies have been investigated in the course of this study: (1) A first one, based on a transesterification approach and (2) another one based on an in-situ formation of a bis(ester amide)
The first successful synthesis of poly(ester amide)s from itaconic acid is described by two different synthetic approaches
Summary
Immense research efforts have been undertaken to implement bio-based monomers as suitable alternative building blocks in polymeric materials [1,2,3,4]. This is mostly driven by the imminent scarcity of fossil resources, as well as the enormous potential to exploit local resources and reduce the dependency on imported fossil fuels. Itaconic acid (IA), known as methylene succinic acid, has drawn considerable attention in this context over the last few years [5] This unsaturated dicarboxylic acid is commercially available in larger quantities (>80.000 t/a) at a competitive price (
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