Preparation and Characterization of Novel Naturally Renewable Resin Acid Based Monomer

Abstract

Rosin, an abundant renewable natural resin obtained from exudation of pine trees, has attracted a great deal of attention because of its utilization as a feedstock for the preparation of polymers in the age of the depletion of fossil fuels. Dehydroabietic acid (DA) is one of important resin acid that could be produced with large scale and high purity. In this paper, we reported a new synthetic strategy to prepare a novel resin acid based monomer with acrylic group (DAHA) by sequential reaction of DA with 1,6-hexanediol and acryloyl chloride. The structure and properties of DAHA and DA monoester of 1,6-hexanediol (DAH), an intermediate compound, were characterized by FT-IR,1H NMR,13C NMR, MS, DSC and GPC. The results showed that DAHA has high purity and could undergo free radical polymerization. DAHA is a soft monomer with the glass transition temperature of-23.52 °C and can impart flexibility to the polymer integrated. This study illustrates a new synthetic strategy to prepare a new class of resin acid based monomer.

Integration of renewable cellulose and rosin towards sustainable copolymers by “grafting from” ATRP

“…S1 †). 54,59,62,63 2.2. Characterization FT-IR analysis was performed using a Nicolet iS10 FT-IR spectrometer by an attenuated total reflectance method.…”

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

“…It can be prepared using: (i) oxalyl chloride according to Scheme 1 prior to evaporation of unnecessary substances [142], (ii) phosphorus trichloride in chloroform (yield 92.5%) [140] or (iii) thionyl chloride in presence of 4-dimethylaminopyridine [143]. It can be used as a substrate for the synthesis of macroinitiators for atom transfer radical polymerization (ATRP) reactions [142], rosin phosphate esters [140], N -hydroxyethylacrylamide ester of dehydroabietic acid [144], dehydroabietic ethyl methacrylate [145,146], dehydroabietic propargyl ester [147] dehydroabietic hexyl acrylate [148], as well as other intermediates in synthesis of various surfactants [143,149] and medicines [141,150,151].…”

“…Dehydroabietic hexyl acrylate is a solid. It can be synthesized from dehydroabietyl chloride, hexanediol and acryloyl chloride according to Scheme 12, and using separation methods such as filtration, precipitation, washing and vacuum drying [148]. Its application is a soft acrylic monomer (glass transition temperature of −23 °C), which can impart a flexibility to the integrated polymer [148].…”