Synthesis and Characterization of Catechol-Containing Polyacrylamides with Adhesive Properties

Hennig, Kathleen; Meyer, Wolfdietrich

doi:10.3390/molecules27134027

Cited by 6 publications

(4 citation statements)

References 35 publications

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“…We focus on free radical polymerization, which is often preferred for larger scale synthesis and applications. Various studies showed the feasibility of free and controlled radical polymerization routes toward uncharged [ 43 , 44 , 45 , 46 , 47 ] and charged [ 24 , 30 , 34 , 35 ] catechol-containing copolymers. Importantly, however, the effect of additional primary amide units was not yet studied in such copolymer systems.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Catechol-Containing Polyacrylamide Copolymers: Synergistic Effects of Amine, Amide and Catechol Residues in Mussel-Inspired Adhesives

Bonda,

Müller,

Fischer

et al. 2023

Polymers

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The straightforward synthesis of polyamide-derived statistical copolymers with catechol, amine, amide and hydroxy residues via free radical polymerization is presented. In particular, catechol, amine and amide residues are present in natural mussel foot proteins, enabling strong underwater adhesion due to synergistic effects where cationic residues displace hydration and ion layers, followed by strong short-rang hydrogen bonding between the catechol or primary amides and SiO2 surfaces. The present study is aimed at investigating whether such synergistic effects also exist for statistical copolymer systems that lack the sequence-defined positioning of functional groups in mussel foot proteins. A series of copolymers is established and the adsorption in saline solutions on SiO2 is determined by quartz crystal microbalance measurements and ellipsometry. These studies confirm a synergy between cationic amine groups with catechol units and primary amide groups via an increased adsorptivity and increased polymer layer thicknesses. Therefore, the free radical polymerization of catechol, amine and amide monomers as shown here may lead to simplified mussel-inspired adhesives that can be prepared with the readily scalable methods required for large-scale applications.

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Catechol-Containing Polyacrylamide Copolymers: Synergistic Effects of Amine, Amide and Catechol Residues in Mussel-Inspired Adhesives

Bonda,

Müller,

Fischer

et al. 2023

Polymers

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“…Surface modification of materials using molecules from the catechol family is emerging as a new area of technological and scientific interest [ 1 , 2 ]. Catecholate molecules can achieve extremely strong adhesion to inorganic surfaces by utilizing a similar adsorption mechanism to that of mussel proteins when bonded to different surfaces [ 2 , 3 , 4 ]. Very fast and very strong adsorption to various inorganic substrates is a necessity for mussels to avoid damage by sea waves.…”

Section: Introductionmentioning

confidence: 99%

“…Very fast and very strong adsorption to various inorganic substrates is a necessity for mussels to avoid damage by sea waves. This adhesion mechanism is attributed to bonding of the catechol ligands of the mussel proteins to metal atoms on material surfaces [ 4 , 5 , 6 , 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Supercapacitor Performance of Magnetite Nanoparticles Enhanced by a Catecholate Dispersant: Experiment and Theory

2023

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The full potential of Fe3O4 for supercapacitor applications can be achieved by addressing challenges in colloidal fabrication of high active mass electrodes. Exceptional adsorption properties of catecholate-type 3,4-dihydroxybenzoic acid (DHBA) molecules are explored for surface modification of Fe3O4 nanoparticles to enhance their colloidal dispersion as verified by sedimentation test results and Fourier-transform infrared spectroscopy measurements. Electrodes prepared in the presence of DHBA show nearly double capacitance at slow charging rates as compared to the control samples without the dispersant or with benzoic acid as a non-catecholate dispersant. Such electrodes with active mass of 40 mg cm−2 show a capacitance of 4.59 F cm−2 from cyclic voltammetry data at a scan rate of 2 mV s−1 and 4.72 F cm−2 from galvanostatic charge–discharge data at a current density of 3 mA cm−2. Experimental results are corroborated by density functional theory (DFT) analysis of adsorption behaviour of DHBA and benzoic acid at the (001) surface of Fe3O4. The strongest adsorption energy (ca. −1.8 eV per molecule) is due to the catechol group of DHBA. DFT analysis provides understanding of the basic mechanism of DHBA adsorption on the surface of nanoparticles and opens the way for fabrication of electrodes with high capacitance.

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Sustainable Snail‐Inspired Bio‐Based Adhesives with Ultra‐High Adhesion

Zhu,

Li,

Yan

et al. 2024

Adv Funct Materials

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Adhesives play a crucial role in modern everyday applications, prompting a growing environmental consciousness regarding their source, composition, utilization, and disposal. Sustainability concerns are frequently generated due to the complex or energy‐intensive manufacturing processes in the production of conventional water‐based adhesives. Here, a coacervate‐based snail‐inspired solvent‐free adhesive (SFA) is engineered by strategically modulating electrostatic interactions and molecular entanglement of two polypeptides under environmentally friendly conditions. The SFA has a record‐breaking adhesion strength of 28 MPa on ceramics, setting a new standard for bio‐based adhesives. The SFA demonstrates robust adhesion performance across a wide temperature ranging from −150 to 300 °C and allows for reusability without compromising adhesion properties. Moreover, it can be easily removed using a non‐toxic alkaline solution. The study presents a promising opportunity for developing high‐performance, reusable adhesives made from renewable materials suitable for industrial applications, relics repair, and even spacecraft processing.

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Synthesis and Characterization of Catechol-Containing Polyacrylamides with Adhesive Properties

Cited by 6 publications

References 35 publications

Facile Synthesis of Catechol-Containing Polyacrylamide Copolymers: Synergistic Effects of Amine, Amide and Catechol Residues in Mussel-Inspired Adhesives

Facile Synthesis of Catechol-Containing Polyacrylamide Copolymers: Synergistic Effects of Amine, Amide and Catechol Residues in Mussel-Inspired Adhesives

Supercapacitor Performance of Magnetite Nanoparticles Enhanced by a Catecholate Dispersant: Experiment and Theory

Sustainable Snail‐Inspired Bio‐Based Adhesives with Ultra‐High Adhesion

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