Ketone derivatives of diels‐alder adducts of levopimaric acid with acrylic acid and maleic anhydride: Synthesis, characterization, and polymerization

Abstract

Two new ketone-type derivatives were synthesized by the dehydrodecarboxylation of levopimaric acid acrylic acid adduct and of levopimaric acid maleic anhydride adduct in the presence of sulfonic catalysts. The two compounds were also synthesized by coupling of acrylic acid or maleic anhydride with dipimaryl ketone. These ketones, or rather ketone-diacids, were condensed with polyalkylenepolyamines to give poly(amide)s or poly(imide)s with good thermal properties. New crosslinked polymers were obtained when these poly(amide)s or poly(imide)s were substituted with epichlorohydrin. The structures of the resulted ketone-diacids and polymers were investigated by the usual physical and chemical methods. EXPERIMENTAL MaterialsAbietic acid, in its isomer form of levopimaric acid (PA), (acid number (AN) ϭ 184 mg of KOH/g, 99%), APA (AN ϭ 295 mg of KOH/g, 98.5%), and MPA (AN ϭ 416 mg of KOH/g, 99%) were prepared and purified as described in ref. 21. DPK (AN ϭ 1.0 mg of Correspondence to: I.

Remembrance of Ray Rappaport, pioneer in the study of cytokinesis

“…The dehydrodecarboxylation reaction is characteristic of abietic acid and its derivatives. It has been studied at other times, too 8, 28, 29. In this reaction are involved the COOH groups that, by releasing carbon dioxide and water, make a new ketone‐type linkage.…”

“…The reactions attributed to the conjugated double bonds of RAs are more easily developed. A typical reaction is coupling by the Diels–Alder mechanism with some philodienes, such as acrylic acid1–7 and its derivatives,1–3, 8, 9 maleic acid,10 fumaric acid,10–12 maleic anhydride11, 13–23 and its derivatives,24 benzoquinones,25 and naphtoquinones 26…”

Dimerization of abietic acid for the design of renewable polymers by ADMET

“…10.021 0014-3057/Ó 2014 Elsevier Ltd. All rights reserved. acid), to yield difunctional monomers and the main chain rosin derived polymers thereof [21][22][23][24][25]. Recently, Tang et al [26] reported the copolymerization of resin acid derivatives with fatty ester derivatives by ADMET polymerization leading to polymers with a molar mass of 9200 g/mol and a Tg of À5°C.…”

Rosin based epoxy coating: Synthesis, identification and characterization

“…Recently, rosin-based compounds were used as a novel one component i-line molecular glass photoresists [7]. Moreover, a great interest was observed in preparing rosin based polymers for enhanced thermal stability [8,9] as well as polyesters [10,11], epoxy resins [12][13][14][15] and epoxy curatives [16][17][18][19][20].…”