- Microphase Behavior and Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a Mussel Foot Protein
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Numerous attempts have been made to translate mussel adhesion to diverse synthetic platforms. However, the translation remains largely limited to the Dopa (3,4-dihydroxyphenylalanine) or catechol functionality, which continues to raise concerns about Dopa
- Seo, Sungbaek,Das, Saurabh,Zalicki, Piotr J.,Mirshafian, Razieh,Eisenbach, Claus D.,Israelachvili, Jacob N.,Waite, J. Herbert,Ahn, B. Kollbe
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- Improved performance of protected catecholic polysiloxanes for bioinspired wet adhesion to surface oxides
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A facile synthetic strategy for introducing catecholic moieties into polymeric materials based on a readily available precursor (eugenol) and efficient chemistries [tris(pentafluorophenyl)borane-catalyzed silation and thiol-ene coupling] is reported. Silyl protection is shown to be critical for the oxidative stability of catecholic moieties during synthesis and processing, which allows functionalized polysiloxane derivatives to be fabricated into 3D microstructures as well as 2D patterned surfaces. Deprotection gives stable catechol surfaces whose adhesion to a variety of oxide surfaces can be precisely tuned by the level of catechol incorporation. The advantage of silyl protection for catechol-functionalized polysiloxanes is demonstrated and represents a promising and versatile new platform for underwater surface treatments.
- Heo, Jinhwa,Kang, Taegon,Jang, Se Gyu,Hwang, Dong Soo,Spruell, Jason M.,Killops, Kato L.,Waite, J. Herbert,Hawker, Craig J.
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- Synthesis of 3,4-dihydroxyphenyl-containing polymeric materials from 1,2-polybutadiene and eugenol via thiol—ene addition
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In a search for routes to new promising adhesive materials, 3,4-dihydroxyphenyl groups were introduced for the first time into syndiotactic polybutadiene (1,2-unit content >90%). Two ways of introduction were studied: cross metathesis and thiol—ene addition. Eugenol, an available product of plant origin, was used as a source of 3,4-dihydroxyphenyl groups following the protection of its oxygen-containing groups with Et3SiH in the presence of B(C6F5)3) as a catalyst. A cross metathesis reaction of polybutadiene with modified eugenol in the presence of the Grubbs catalysts of different generations resulted in considerable degradation of the polymer into the corresponding low-molecular-weight products. A new approach involving thiol—ene addition afforded 3,4-dihydroxyphenyl-containing polybutadienes with desired catechol contents and desired molecular weights.
- Chapala,Bermeshev,Korchagina,Ashirov,Bermesheva
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- Catechol-Functionalized Polyolefins
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The incorporation of comonomers during ethylene polymerization can efficiently modulate important material properties of the polyolefins. Utilizing bioresourced comonomers for the generation of high-performance polyolefin materials is attractive from a sustainability point of view. In this contribution, bioresourced eugenol and related comonomers were incorporated into polyolefins through palladium-catalyzed copolymerization and terpolymerization reactions. Importantly, high-molecular-weight catechol-functionalized polyolefins can be generated. The introduction of different metal ions induces efficient interactions with the incorporated catechol groups, leading to enhanced mechanical properties and self-healing properties. Moreover, the catechol functionality can greatly improve other properties such as surface properties, adhesion properties, and compatibilizing properties. The catechol-functionalized polyolefin was demonstrated as a versatile platform polymer for accessing various materials with dramatically different properties.
- Chen, Changle,Na, Yinna
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supporting information
p. 7953 - 7959
(2020/04/10)
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- Compound containing catechol and thiol group, and preparation method and use thereof
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The present invention relates to a compound which contains both a catechol group and a thiol group and is represented by chemical formula 1. The present invention further relates to a production method thereof, and a use of the same as a bioadhesive and an antifoulant. In the chemical formula 1, R^1 is either hydrogen or a substituted group represented by chemical formula 2 respectively, and at least one among R^1 has the substituted group represented by chemical formula 2.
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Paragraph 0028; 0074; 0075; 0076
(2017/01/26)
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- ORGANIC SILICON COMPOUND, ADHESIVE COMPOSITION, AND ARTICLE
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PROBLEM TO BE SOLVED: To provide an organic silicon compound used for an adhesive composition and having a catechol structure. SOLUTION: An organic silicon compound comprises a hydrolyzable silyl group and a catechol structure protected with a silyl group
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Paragraph 0041
(2018/10/04)
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