Phosphonated and methacrylated biobased cardanol monomer: Synthesis, characterization and application

Abstract

To create adhesive coatings, biobased phosphorylated monomer from cardanol was synthesized and polymerized by UV curing or miniemulsion radical polymerization.Phosphonic ethoxy cardanol methacrylate (CMP) was synthesized from cardanol via hydroxyethylation, followed by phosphorylation radical addition of dimethyl phosphite onto the unsaturations of the C15 aliphatic chain of cardanol prior methacrylation of the hydroxyl ethoxy group. Lastly the cleavage of the phosphonate ester groups was made to generate the targeted phosphonic acid moieties as adhesion promoters. Moreover, the development of a phosphonic latex was successfully achieved by miniemulsion radical copolymerization in water with an additional redox termination to ensure quantitative monomer conversions.Phosphonic cardanol and cardanol (as reference) latexes were characterized by dynamic light scattering. The effects of cardanol derivatives on the performance of protective coatings on steel plates were evaluated in UV-cured coatings as well as in latex coatings in terms of contact angle and adhesion effectiveness. In coatings, increased hydrophobic properties were observed in fomulations containing free cardanol or cardanol methacrylate.On the other side, the incorporation of phosphonic acid groups onto cardanol significantly improved the adhesion effectiveness of the coating, whatever the film-making technique.

Phosphorus Modified Cardanol: A Greener Route to Reduce VolaTile Organic Compounds and Impart Flame Retardant Properties to Alkyd Resin Coatings

“…Nevertheless, the GC slightly decreased with the amount of phosphorylated cardanol. This may be attributed to the percentage of saturated chains of cardanol which accounted for 5–8% of the alkyl chains [ 22 ]. Indeed, depending on the amount of phosphorylated cardanol introduced, the percentage of saturated chains oscillated between 1 and 5 wt% of the total mass of the alkyd resins.…”

“…Nowadays, the use of industrial wastes or by-products is one of the environmental challenges faced by many industries and universities over the past few years [ 6 ]. Cashew nut shell liquid (CNSL), is a non-edible by-product of the cashew nut industry, directly extracted from the cashew nut shell [ 22 ]. With an annual production approaching one million tons, CNSL is a major and economical renewable resource [ 23 , 24 ].…”

Biobased Composites by Photoinduced Polymerization of Cardanol Methacrylate with Microfibrillated Cellulose

“…The use of cardanol-based acrylates and epoxidized cardanol-based acrylates as a reactive diluent in photocurable castor oil polyurethane acrylate and acrylated epoxidized soybean oil resins was also reported [ 19 , 20 , 21 ]. Cardanol methacrylate was used as additive for UV-curable tripropylene glycol diacrylate/1,6-hexanediol diacrylate formulations, to increase their hydrophobicity [ 22 ]. Acrylated cardanol diphenyl phosphate was added to urethane acrylate UV-curable coatings, enhance flame-retardant properties, and reduce volume shrinkage [ 23 , 24 ].…”

Cardanol-modified alkyd resins: novel route to make greener alkyd coatings

“…4 Nowadays, the world production of cardanol almost reaches one million ton per years. 5 Cardanol is composed of a phenol group with an unsaturated 15-carbon side chain which can exhibit until three Thereby, the structure of the alkyl chain of cardanol could provide interesting coating properties such as flexibility, hydrophobicity, chemical resistance, flame retardant and anti-corrosion properties. 5,[10][11][12][13][14][15][16][17] Numerous of those studies focused on the introduction of acrylate-cardanol-based monomers in order to obtain ultra-violet (UV)-curable coatings.…”

“…5 Cardanol is composed of a phenol group with an unsaturated 15-carbon side chain which can exhibit until three Thereby, the structure of the alkyl chain of cardanol could provide interesting coating properties such as flexibility, hydrophobicity, chemical resistance, flame retardant and anti-corrosion properties. 5,[10][11][12][13][14][15][16][17] Numerous of those studies focused on the introduction of acrylate-cardanol-based monomers in order to obtain ultra-violet (UV)-curable coatings. Li et al studied the formation of latex-based coatings with higher adhesion performance thanks to the incorporation of phosphonated acrylated cardanol monomers.…”