Bio-Based Coating Materials Derived from Acetoacetylated Soybean Oil and Aromatic Dicarboxaldehydes

Abstract

Bio-based coating materials were prepared from epoxidized soybean oil as a renewable source. Acetoacetylated soybean oil was synthesized by the ring-opened and transesterification reaction of epoxidized soybean oil, and its chemical structure was characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), gel permeation chromatography (GPC), and rheometric viscosity analyses. On the basis of acetoacetylated soybean oil, several bio-based coating materials were prepared using different aromatic dicarboxaldehydes (1,2-benzenedialdehyde, 1,3-benzenedialdehyde, 1,4-phthalaldehyde, 4,4′-biphenyldicarboxaldehyde) and characterized. The resulting films possess good performance, including the highest glass transition temperature of 54 °C, a Young’s modulus of 24.91 MPa, tensile strength of 5.65 MPa, and an elongation at break of 286%. Thus, this work demonstrates the Knoevenagel condensation reaction, which is based on soybean oil as a potential newer eco-friendly raw material.

Organic–inorganic hybrid coating materials derived from renewable soybean oil and amino silanes

“…[1][2][3][4] Vegetable oils, as renewable resources, have unique chemical structures containing hydroxyls, esters, unsaturated sites, and other functional groups, and these can be modied to make low molecular weight polymeric materials for a range of versatile applications. [5][6][7][8][9] Acetoacetyl chemistry is interesting to use to prepare thermoset resins because acetoacetate functional groups can react with various groups, [10][11][12][13] including aldehydes, 14 isocyanates, 15 acrylates, 16 and amines. 17 Although many thermoset resins have been prepared using acetoacetate chemistry and amines, only a few studies have been reported on the synthesis of biobased coating materials.…”

The Synthesis of Bio-Based Michael Donors from Tall Oil Fatty Acids for Polymer Development

“…There are many publications on the double bond epoxidation of fatty acids by different methods for further synthesizing polyols by ring-opening reactions with alcohols [ 8 , 9 , 10 , 11 ]. In a couple of studies, these polyols are used as a part of component A to produce polyurethanes [ 3 , 7 , 12 , 13 , 14 , 15 ]. Isocyanates are used as component B in conventional polyurethane production.…”

“…Hydroxyl groups of polyols can be converted to β-ketoesters to obtain polymers with acrylates by the Michael reaction. Although the method is known, the research has mainly been conducted for coating materials [ 12 , 22 , 23 , 24 , 25 ].…”

“…A limited number of studies on acetoacetylation of bio-based polyols have been published. Acetoacetylation has been successfully demonstrated in the synthesis of soybean-oil-based polyols [ 12 ], castor oil and castor-oil-based polyols [ 22 , 23 , 24 , 25 , 26 , 27 ]. Hydroxyl groups of fatty acids polyols are relatively easy to acetoacetylate with tert -butyl acetoacetate by a transesterification reaction, thereby obtaining β-ketoesters.…”

“…Hydroxyl groups of fatty acids polyols are relatively easy to acetoacetylate with tert -butyl acetoacetate by a transesterification reaction, thereby obtaining β-ketoesters. The reaction is mostly carried out at a temperature of 110–130 °C [ 12 , 22 , 23 , 24 , 28 , 29 ].…”