Synergistic Effects of Cardanol- and High Oleic Soybean Oil Vinyl Monomers in Miniemulsion Polymers

Abstract

Along with characterization of vinyl monomers from high oleic soybean oil (HOSBM) and cardanol (CBM) in free radical (co)polymerization, a series of stable latexes based on various ratios of these monomer mixtures have been synthesized using miniemulsion process. By combination of aliphatic fatty acid fragments of HOSBM with aromatic CBM structure, durable latexes from fully renewable feeds were expected, as well as the ability to balance thermomechanical properties of resulting crosslinked latex films. Biobased latexes were synthesized from 10-75 wt.% of CBM and 25-90 wt.% of HOSBM in the feed, characterized, and tested in films and coatings performance. Synergistic effects of both constituents in the films and coatings were observed. Incorporation of cardanol-based fragments enhances Young's modulus of the films, whereas the plant oil-based units contribute to softer and more flexible films. Even small (10 wt.%) fractions of CBM can provide noticeable strength to the soft latex polymer material based entirely on HOSBM. All crosslinked latex films in this study exhibit decent properties and performance in terms of pendulum and pencil hardness, water and solvent resistance as well as adhesion to the steel substrate. To the best of our knowledge, latexes from fully renewable plant-based monomer mixtures have not been reported before in literature.

Biobased Latexes from Soy and Vanillin Derived Vinyl Monomers

“…To this end, vinyl monomer derived from aromatic cardanol (CBM) and monomer from high oleic soybean oil (HOSBM) were successfully copolymerized in miniemulsion to yield biobased latexes in our recent study. 3 As a result, both biobased fragments contributed to the mechanical properties of the synthesized latexes. The incorporation of aromatic fragments of cardanol enhances Young's modulus of the films, whereas the fatty POBM constituents made the material more flexible.…”

“…% of CBM fragments provided noticeable strength to the soft latex polymeric material from entirely HOSBM. 3 Furthermore, we elaborated on hypothesis of combining aromatic and aliphatic biobased ingredients in emulsion/miniemulsion copolymerization process. For this purpose, new vanillin-derived compound, 3-allyl-5vinylveratrole (AVV) 4 was chosen as a comonomer for copolymerization with HOSBM.…”

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

“…The double bonds from the soybean oil-based comonomer underwent auto-oxidation and formed crosslinked structures with drastically enhanced mechanical properties, viz., good candidates for coating applications [ 74 ]. A more sustainable approach copolymerized soybean methacrylate with cardanol methacrylate, being the first latex produced with fully plant-based comonomers to be reported in the literature [ 75 ]. Another recent contribution performed a physical crosslinking between copolymers of soybean methacrylate and 2-carboxy methyl acrylate by metal-ligand coordination [ 76 ].…”

Non-Conventional Features of Plant Oil-Based Acrylic Monomers in Emulsion Polymerization

“…Caillol et al [ 22 , 23 ] proposed methods for the synthesis of a new monomer from cardanol ( Figure 2 ), which is isolated from cashew nuts. Reactivity of the cardanol-based monomer in the copolymerization reactions with the POBMs was studied [ 24 ].…”

“…Copolymerization of monomers synthesized from various plant oils, which have different unsaturation, enables formation of copolymers with side branches of the macrochain with different unsaturation degrees. A large variety of the POBMs allows to synthesize polymers having moieties with different unsaturation and to make coatings with adjustable cross-linking degree thereof, including latex copolymers from fully biobased monomer mixtures [ 24 ]. Remarkably, copolymerization of the POBMs with commercial vinyl monomers enables synthesis of polymers with enhanced hydrophobicity along with the mechanism of internal plasticization.…”