Synthesis and characterization of biocompatible copolymers containing plant-based cardanol and zwitterionic groups for antifouling and bactericidal coating applications

Kim, Na Kyung; Kim, Jinseok; Shon, Da-Jung; Lee, Ju‐Ro; Choi, Yong‐Seok; Yook, Jinsol; Kim, Byung Soo; Lee, Jong-Chan

doi:10.1016/j.eurpolymj.2018.10.034

Cited by 19 publications

(10 citation statements)

References 41 publications

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“…This sequence afforded a poorly (46%) biobased surfactant as a mixture with predominantly an unsaturated aliphatic chain of one to three alkenes. In 2019, a series of copolymers containing sulfobetaine and cardanol was synthesized via free radical polymerization of methacrylate derivatives (Scheme 31) [113]. After ringopening reaction of glycidyl methacrylate by cardanol, the aromatic compound having methacrylate moiety was added to a solution of (dimethylamino)ethylmethacrylate and AIBN in different ratios.…”

Section: Zwitterionic Surfactants Based On Cnslmentioning

confidence: 99%

“…The synthesis of zwitterionic copolymers Z-4 with cardanol and a significant proportion of sulfobetaine core not only revealed excellent bactericidal properties, but also an interesting adhesion resistance to proteins, bacteria and cells, with sufficient biocompatibility [113]. When the copolymers contain more than 58 mol% of cardanol, the bactericidal propriety increases against Escherichia coli.…”

Section: Biological Activity Cytotoxicity and Biodegradabilitymentioning

confidence: 99%

“…The antibacterial activities are attributed to positive charges introduced by ammonium and pyridinium groups. In the specific case of zwitterionic copolymers Z-4 containing cardanol and zwitterionic groups, Kim et al [113] indicated that promising coating materials can be made from these polymers in biomedical devices and water purification. As for nonionic CNSL surfactants, Prasad et al [135] showed that cardanol-based glycolipids NI-13 and NI-13 were able to disrupt biofilms formed by pathogens, such as E. coli and Salmonella enterica Typhimurium.…”

Section: Applications Of Cnsl-based Surfactantsmentioning

confidence: 99%

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CNSL, a Promising Building Blocks for Sustainable Molecular Design of Surfactants: A Critical Review

Roy¹,

Fajardie

Lepoittevin

et al. 2022

Molecules

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Surfactants are crystallizing a certain focus for consumer interest, and their market is still expected to grow by 4 to 5% each year. Most of the time these surfactants are of petroleum origin and are not often biodegradable. Cashew Nut Shell Liquid (CNSL) is a promising non-edible renewable resource, directly extracted from the shell of the cashew nut. The interesting structure of CNSL and its components (cardanol, anacardic acid and cardol) lead to the synthesis of biobased surfactants. Indeed, non-ionic, anionic, cationic and zwitterionic surfactants based on CNSL have been reported in the literature. Even now, CNSL is absent or barely mentioned in specialized review or chapters talking about synthetic biobased surfactants. Thus, this review focuses on CNSL as a building block for the synthesis of surfactants. In the first part, it describes and criticizes the synthesis of molecules and in the second part, it compares the efficiency and the properties (CMC, surface tension, kraft temperature, biodegradability) of the obtained products with each other and with commercial ones.

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Section: Zwitterionic Surfactants Based On Cnslmentioning

confidence: 99%

Section: Biological Activity Cytotoxicity and Biodegradabilitymentioning

confidence: 99%

Section: Applications Of Cnsl-based Surfactantsmentioning

confidence: 99%

See 1 more Smart Citation

CNSL, a Promising Building Blocks for Sustainable Molecular Design of Surfactants: A Critical Review

Roy¹,

Fajardie

Lepoittevin

et al. 2022

Molecules

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“…One strategy to prepare antibacterial polymers is to incorporate low-molecular-weight materials with strong bactericidal activities in the polymer. , Cationic compounds, including quaternary ammonium salts, , plant-based antibacterial molecules, − and antibiotics, including ciprofloxacin, , have been commonly used as such materials. The bactericidal properties of these materials significantly depend on their structures, particularly the nature and position of the functional groups affecting their interaction with bacteria. − Low-molecular-weight bactericidal material can be incorporated by chemical reaction with the monomer followed by polymerization or by modification reaction with the polymer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Citronellol-Derived Antibacterial Polymers and Effect of Thioether, Sulfoxide, Sulfone, and Ether Functional Groups on Their Bactericidal Activity

2023

Self Cite

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Citronellol-derived methacrylate polymers with four side chain interconnecting groups of different polarities (PCHM-Xs) are synthesized to prepare bio-based bactericidal polymers. The PCHM-X bactericidal activities are significantly affected by the different functional groups determining the interaction between the polymer chain and bacterial membrane that disrupts the membrane integrity causing cytoplasmic leakage, the main contributor to the polymer antibacterial properties. PCHM-SO, with a large dipole moment and strong hydrogen bonding ability, shows the best bactericidal activity among PCHM-Xs due to the strongest interactions with the bacterial membrane components. A sulfoxide-group-containing polymer with excellent bactericidal activity (99.99%) and the systematic study of the effect of different functional groups on the bactericidal activity are first reported herein.

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“…30 Cardanol-based acrylates were classically prepared by the chemical modification of the unsaturation of the side chain 31,32 but recently, different teams suggested the acrylation of the phenol via acryloyl chloride 33 directly on cardanol or on the product of cardanol-epichlorohydrin. 28,34 Our team proposed the hydroxyethylation of the phenolic hydroxyl group followed by methacrylation using methacrylic anhydride. A biobased reactive diluent, cardanyl acrylate, was synthesized from cardanol and used to modify a castor oil-based polyfunctional polyurethane acrylate (PUA) resin.…”

Section: Introductionmentioning

confidence: 99%

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

Cuminet

Ladmiral

et al. 2021

Progress in Organic Coatings

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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.

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Synthesis and characterization of biocompatible copolymers containing plant-based cardanol and zwitterionic groups for antifouling and bactericidal coating applications

Cited by 19 publications

References 41 publications

CNSL, a Promising Building Blocks for Sustainable Molecular Design of Surfactants: A Critical Review

CNSL, a Promising Building Blocks for Sustainable Molecular Design of Surfactants: A Critical Review

Synthesis of Citronellol-Derived Antibacterial Polymers and Effect of Thioether, Sulfoxide, Sulfone, and Ether Functional Groups on Their Bactericidal Activity

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

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