Acrylated Biopolymers Derived via Epoxidation and Subsequent Acrylation of Vegetable Oils

Abstract

Chemically modified vegetable oils have become commercially attractive nowadays because they can be utilized as specialized components for the production of bioplasticizers and biopolymers due to their characteristics as being inexpensive, nontoxic, biodegradable, and renewable products. Due to the presence of unsaturation sites in the vegetable oils, they can be chemically modified and transformed into polymeric monomers such as acrylated epoxidized vegetable oils through well-known processes like epoxidation and acrylation processes. Acrylated epoxidized vegetable oil is a biopolymer that has a multitude of applications and is used mainly as a coating material for plastic, paper, and wood. There is an enormous demand for this biopolymer, and the market growth prospects are huge in some regions of the world. However, there are some challenges in the synthesis of acrylated epoxidized vegetable oils in achieving the performance of similar acrylated polymer derived from petroleum sources. In this paper, the chemical structure, properties, and chemical modifications of different types of vegetable oils were reviewed where the emphasis was given on epoxidation and its subsequent acrylation processes. This paper also highlights four types of epoxidation and their subsequent acrylation processes involving five different vegetable oils.

One-Step Method for Direct Acrylation of Vegetable Oils: A Biobased Material for 3D Printing

“…The efficiency of different nucleophilic catalysts was evaluated using the same operational conditions in order to select the most appropriate catalysts for use in the process. TEA and TPP were selected as two of the most common catalysts used in acrylation reactions [ 18 ], together with three salts of chromium (III).…”

“…On the other hand, acrylation of vegetable oils has been generally carried out as a two-step process consisting in an initial epoxidation reaction (as explained above), followed by acrylation using acrylic acid. This is the common way of obtaining acrylated epoxidized vegetable oils, such as the ones made of soybean, palm, castor, linseed, or Jatropha seed [ 17 , 18 , 19 ]. However, in terms of green chemistry (atom economy) and cost-effectiveness, it would be desirable to synthesize acrylated vegetable oils via the direct addition of acrylic acids to the carbon–carbon double bond of the triglyceride as it is prone to capturing electrophiles [ 20 ].…”

Synthesis and application of sustainable vegetable oil-based polymers in 3D printing

“…The main variables affecting the acrylation process are the molar concentration of EVO to acrylic acid, the rate of reaction, the nature and quantity of EVO, and the catalyst and inhibitor used. 110 The primary purpose of an inhibitor is to prevent homo-polymerization during the reaction process. Various inhibitors, such as 4-methoxyphenol, 111 hydroquinone, 112 and 4- tert -butylcatechol, 113 are employed in acrylation reactions.…”

Interaction of porous substrate and vegetable oil-based hydrophobic thermoset coatings during UV-polymerization

“…Specific acrylate group peaks were observed at 1636, 1406 and 810 cm À1 , indicating a successful ring-opening acrylation reaction. 28 After UV polymerization of the AELO coatings, these peak the intensities decreased, indicating that the double bonds in the acrylate groups cleaved and converted to single -C-H bonds known also as crosslinking, resulting in an increase in the -C-H stretch intensity at about 3000 cm À1 . The same spectral changes were observed in the FT-IR spectrum of acrylated epoxidized soybean oil in a self-healing reaction with pentaerythritol tetrakis(3-mercaptopropionate).…”