Polymers from a levopimaric acid–acrylonitrile Diels–Alder adduct: Synthesis and characterization

Abstract

The Diels–Alder adduct of levopimaric acid with acrylonitrile was efficiently prepared from resin acids. Excellent addition reaction yields (ca. 95%) were obtained. The adduct was converted into polyamides by polycondensation with diamines. When the same adduct was subjected to a dehydrodecarboxylation reaction, a novel ketone dinitrile derivative was obtained. This trifunctional product was also converted into polyamides by polycondensation with diamines. When the ketone dinitrile was hydrolyzed in the presence of alkalies and the reaction product was chlorinated, a ketone diacid chloride was obtained. A polyester was synthesized by the polycondensation of the diacid chloride with a diol. The structures of the Diels–Alder adduct, ketone dinitrile derivative, ketone diacid chloride, and polymers were established by means of elemental analysis, IR and NMR spectroscopy, and molecular weight determinations. Both the polyamides and the polyester were low‐molecular‐weight polymers soluble in polar solvents. The thermal behavior of the monomers and polymers was evaluated by thermogravimetric analysis. The thermal studies showed that the polymers were fairly thermostable substances, except the polyester, which appeared to be a substance with good thermal stability. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 6308–6322, 2005

Recent Progress in Sustainable Polymers Obtained from Cyclic Terpenes: Synthesis, Properties, and Application Potential

“…[102] ChemSusChem 2015, 8,2455 -2471 www.chemsuschem.org this, for example, the monomers acrylopimaric acid (APA) and maleopimaric acid (MPA), which are derived from abietic acid, can be utilized (Figure 7). [107] Examples for such structuresa re polyketones, [108] photoactive polyamide-imides, [109] or polyamides, [110] which are all obtained by corresponding polycondensation reactions (Figure 7). Similar 17-and bileacid based polycondensation products have also been prepared;t hey have been reviewed elsewhere in detail.…”

Sustainable thermoplastic elastomers derived from renewable cellulose, rosin and fatty acids

“…Cellulose is an abundant renewable biopolymer. [39][40][41] DAEMA is a methacrylate-based monomer containing renewable resin acid from rosin, [42][43][44][45][46][47][48][49][50] and LMA is derived from a renewable fatty acid. In our related previous work, we reported the polymerization of DAEMA monomer by ATRP to produce homopolymers and block copolymers with controlled molecular weight and low polydispersity index.…”

Renewable rosin fatty acid polyesters: the effect of backbone structure on thermal properties

“…Acrylopimaric acid (APA) was synthesized according to the literature. 30 APA (2·5g, 6·67 × 10 -3 mol) was mixed with THF (50 ml) and introduced into a round bottom fl ask under nitrogen. Oxalyl chloride (2·3 ml, 2·70 × 10 -2 mol) was slowly added to the above mixture at 0°C for 1 h. The mixture was allowed to react for 24 h at room temperature.…”

“…24,26,27 In contrast, rosin that is obtained from pine resin is available with a more rigid fused-ring structure, and can also undergo a pyramid of reactions. 20,[28][29][30][31][32][33][34][35][36] Olefi n metathesis and thiolene reactions are just a few examples of highly effi cient reactions that take advantage of the unsaturated terminal olefi ns to produce valuable monomers. [37][38][39][40] With a range of renewable monomers, it is important to understand how monomers with different structural characteristics affect the properties of their corresponding renewable polymers.…”