Solvent‐induced self‐assembly in cardanol‐based urethane methacrylate comb polymers

Abstract

We report side chain urethane-methacrylate comb polymers based on the renewable resource cardanol and its saturated analogue 3-pentadecyl phenol and their self-assembly into pores, spheres, vesicles, tubes, and so forth. The monomers were synthesized in one pot by coupling 1 equiv. of isophorone diisocyanate with 1 equiv. of cardanol/pentadecyl phenol followed by coupling with 1 equiv. of hydroxyethyl methacrylate. They were polymerized free radically using benzoyl peroxide as the initiator and were characterized by NMR and FTIR, and their molecular weights were determined by gel permeation chromatography. The unique polymer design had sites for self-organization via hydrogen bonding of the side chain urethane units, p-p stacking interactions of the aromatic units as well as interdigitation of the long C 15 alkyl side chains in the polymer. The morphologies of solvent cast polymer films were studied using microscopic techniques such as scanning electron microscopy, transmission electron microscopy, and atomic force microscopy. The polymers exhibited three-dimensional honeycomb morphology in CHCl 3 , whereas in tetrahydrofuran, they formed spheres. The direct cardanol-derived polymer PCIH showed a tendency for multiple morphologies such as spheres and tubes in tetrahydrofuran.

Functionalization of cardanol: towards biobased polymers and additives

“…3-pentadecylphenol were incorporated as pendant units to the side chain urethanemethacrylate through hydrogen bondable urethane linkage (Scheme 17) and the authors observed various morphologies such as tubes, spheres, and honeycomb patterns in drop cast lms. 199…”

Synthesis and curing kinetics of cardanol-based curing agents for epoxy resin by in situ depolymerization of paraformaldehyde

“…The unique structure and renewable nature of cardanol make it an ideal raw material to realize the green chemical strategy for chemical industry. Recently, synthesis of cardanol‐based polymers have gained considerable research interest, especially for use in the production of phenolic resins, vinyl resins, biomass‐based materials, polyurethane, and soft nanomaterials . However, despite the projected potentialities of CNSL, only a few have been realized commercially.…”

Synthesis and Characterization of 4-Aryl-4H-chromenes from H-Cardanol

“…A solution of C4-SMe 4H-chromene (6) (0.2 g, 0.4 mmol) and H-cardanol (1) (0.39 g, 1.2 mmol) in EtOH (6 mL) was refluxed for 12 h to provide 2s (0. 23 Hz, 3H), 2.59 (t, J = 7.4 Hz, 2H), 2.43 (t, J = 7.4 Hz, 2H), 1.63-1.52 (m, 4H), 1.27 (br, 48H), 0.9 (t, J = 6.1 Hz, 6H). 13…”

“…The 4-aryl-4H-chromene 2s has a polar core with two long chain pentadecyl, non-polar and hydrophobic wings. Such molecules, when properly aggregated, could exhibit liquid crystallinity and the ensuing display characteristics [23].…”