Synthesis, Characterization of a Rosin-based Epoxy Monomer and its Comparison with a Petroleum-based Counterpart

A bio-based epoxy derived from dehydroabietylamine was synthesized. In comparison, its petrochemical counterpart based on benzylamine was also prepared. Their chemical structures were confirmed in detail by Fourier Transform Infrared Spectra (FT-IR) and Nuclear Magnetic Resonance (1H-NMR and HSQC). The curing reactions of these synthesized epoxies with hexahydrophthalic anhydride were studied by Differential Scanning Calorimeter (DSC). The mechanical properties and thermal stability of the cured epoxies were investigated by Universal Mechanical Testing Machine, Dynamic Mechanical Analysis (DMA) and Thermogravimetric Analyzer (TGA), respectively. The results indicated that the bulky fused diterpene structure in dehydroabietylamine led to a weaker molecular motion ability and a lower cross-link density, so that the cured epoxy derived from dehydroabietylamine processed a higher glass transition temperature (167°C), but lower mechanical properties than those of the benzylamine-based one.

[1]  L. Cindrella,et al.  Synthesis and Characterization of NiS/MnS Core-Shell Embedded Conducting Polyaniline Composite for Photovoltaic Application , 2010 .

[2]  Xiaoqing Liu,et al.  Rosin-based acid anhydrides as alternatives to petrochemical curing agents , 2009 .

[3]  W. H. Schuller,et al.  Thermal Dimerization of Rosin , 1969 .

[4]  Rashmi,et al.  Polyhydroxyalkanoates: an overview. , 2003, Bioresource technology.

[5]  Guangyuan Zhou,et al.  Synthesis of rosin‐based imidoamine‐type curing agents and curing behavior with epoxy resin , 2011 .

[6]  V. Cádiz,et al.  Development of novel phosphorus‐containing epoxy resins from renewable resources , 2006 .

[7]  J. Galy,et al.  Preparation and properties of bio-based epoxy networks derived from isosorbide diglycidyl ether , 2011 .

[8]  Soo-Jin Park,et al.  Synthesis and Thermal Properties of Epoxidized Vegetable Oil , 2004 .

[9]  D. J. Hourston,et al.  Rigid interpenetrating polymer network foams prepared from a rosin-based polyurethane and an epoxy resin , 1998 .

[10]  R. Gross,et al.  Biodegradable polymers for the environment. , 2002, Science.

[11]  J. D. Sudha,et al.  Polymeric resins from renewable resources. II. Synthesis and characterization of flame‐retardant prepolymers from cardanol , 1990 .

[12]  H. E. Kissinger.  Variation of Peak Temperature With Heating Rate in Differential Thermal Analysis , 1956 .

[13]  A. P. Costa,et al.  Dynamic mechanical and thermal behavior of epoxy resins based on soybean oil , 2002 .

[14]  J. Filipović,et al.  Synthesis and characterization of poly(2-hydroxyethyl methacrylate/itaconic acid/poly(ethylene glycol) dimethacrylate) hydrogels , 2012 .

[15]  P. Gruber,et al.  Polylactic Acid Technology , 2000 .

[16]  A. Gaset,et al.  Biomass as a source of chemicals. VI. Synthesis of new polyfunctional ethers of isosorbide in solid-liquid heterogeneous mixtures , 1986 .

[17]  Zhi-rong Chen,et al.  Iron chloride supported on pyridine-modified mesoporous silica: an efficient and reusable catalyst for the allylic oxidation of olefins with molecular oxygen , 2008 .

[18]  A. Atta,et al.  Epoxy resins from rosin acids: synthesis and characterization , 2004 .

[19]  Henry Lee,et al.  Handbook of Epoxy Resins , 1967 .

[20]  Xiaoqing Liu,et al.  Rosin-derived imide-diacids as epoxy curing agents for enhanced performance. , 2010, Bioresource technology.

[21]  Ernst Worrell,et al.  Present and future development in plastics from biomass , 2010 .