Biocompatible Catechol‐Functionalized Cellulose‐Based Adhesives with Strong Water Resistance

Abstract

Numerous traditional adhesives have good adhesion in dry environments. However, non-environmental-friendliness and poor water resistance largely limit their practical applications. To prepare biocompatible adhesives with strong water resistance and adhesion strength, in this paper, catechol-functionalized cellulose-based adhesive polymers are synthesized by grafting N-(3,4-dihydroxyphenethyl)methacrylamide and methyl methacrylate onto cellulose chain through atom transfer radical polymerization (ATRP). The successful synthesis of the catechol-functionalized cellulose-based adhesive polymers is confirmed by FTIR and 1 H NMR. The different characteristics of the adhesive polymers, such as thermal stability, swelling ratio, biocompatibility, and adhesion strength are investigated. Strong water resistance on various substrates is realized in underwater environment for the catechol-functionalized cellulose-based adhesive with addition of Fe 3+ . The adhesion strength and thermal stability are enhanced when the catechol content is increased. The adhesive with catechol content of 25.4% shows the adhesion strength of 0.45 MPa for iron substrate in underwater environment. In addition, the adhesive with addition of Fe 3+ exhibits excellent adhesion in dry environment, with maximum adhesion strength of 3.50 MPa for iron substrate. The cell culture test shows that the adhesive polymers have excellent biocompatibility. The biocompatible adhesives with strong water resistance have potential application in electronic, wood, and building fields.

A Green Catechol-Containing Cellulose Nanofibrils-Cross-Linked Adhesive

“…51 The copolymer adhesive with 9.0% catechol, 11.2% anhydroglucose units, and 79.8% methyl methacrylate showed lap shear strengths of 2.5 ± 0.5 MPa on steel, 2.1 ± 0.4 MPa on aluminum, 1.3 ± 0.2 MPa on wood, and 0.5 ± 0.2 MPa on glass, respectively. 39 The lap shear strength of acrylated epoxidized soybean oil and 3,4dihydroxybenzoic acid copolymer with Fe 3+ was about 0.5 MPa on wood, 1.9 MPa on aluminum, 1.8 MPa on glass, respectively. 11 For the adhesion of polydopamine/carboxymethyl cellulose/poly(acrylic acid) hydrogels on steel, aluminum, and glass, the lap shear strength was 0.8 ± 0.1, 0.4 ± 0.1, and 0.2 ± 0.1 MPa, respectively.…”

“…The maximum lap shear strength of poly­( l -lysine HBr) x -(L-DOPA) y on steel was about 5.3 MPa . The copolymer adhesive with 9.0% catechol, 11.2% anhydroglucose units, and 79.8% methyl methacrylate showed lap shear strengths of 2.5 ± 0.5 MPa on steel, 2.1 ± 0.4 MPa on aluminum, 1.3 ± 0.2 MPa on wood, and 0.5 ± 0.2 MPa on glass, respectively . The lap shear strength of acrylated epoxidized soybean oil and 3,4-dihydroxybenzoic acid copolymer with Fe 3+ was about 0.5 MPa on wood, 1.9 MPa on aluminum, 1.8 MPa on glass, respectively .…”

“…The synthesis of protected dopamine methacrylamide (DMA) was described in our previous work. 39 Briefly, 9.0 g of DOPA•HCl suspended in 180 mL of CH 2 Cl 2 containing 16 mL of triethylchlorosilane and 20.6 mL of TEA was stirred for 4 h at room temperature. Next, 7.5 mL of TEA and 4.7 mL of methacryloyl chloride were added and stirred overnight at room temperature.…”

Rational design of adhesives for effective underwater bonding

“…A representative group was catechol, the special functional group that worked excellently in marine mussel’s adhesion ( Lee et al, 2011 ; Hofman et al, 2018 ; Li S. D. et al, 2020 ). Due to its multiple interactions with various substance such as H bonds, covalent bonds, coordination interaction and π-π stacking ( Moulay, 2014 ; Saiz-Poseu et al, 2019 ), catechol group has been introduced into the design of man-made adhesives through polymerization ( Matos-Perez et al, 2012 ; Meredith et al, 2014 ; North et al, 2017 ; Tang et al, 2021 ), coupling reaction ( Ryu et al, 2015 ; Shin et al, 2015 ; Li S. D. et al, 2020 ), Michael addition ( Zhang et al, 2014 ; Cui et al, 2019 ), in vivo residue-specific incorporation strategy ( Yang et al, 2014 ), etc. Even catechol group endowed the adhesives with considerable adhesive performance, only a few catechol-based adhesives that exhibited excellent underwater adhesion properties were reported ( North et al, 2017 ; Zhan et al, 2017 ).…”

Bifunctional Cellulose Interlayer Enabled Efficient Perovskite Solar Cells with Simultaneously Enhanced Efficiency and Stability

“…[30,31] The hydroxyl groups on anhydroglucose units are suited for various chemical modifications, which have shown wide applications in the fields of adhesives, hydrogels, electronic devices, photovoltaic devices, etc. [32][33][34][35][36][37][38][39][40][41] Due to the electron lone pairs of the O atoms and the rich hydrogenbonding interactions, the cellulose derivatives such as ethyl cellulose, [39] cellulose acetate, [40] hydroxyalkyl cellulose [35] and cellulose acetate butyrate [34] have been introduced into the PSCs to passivate the defects at the perovskite grain boundaries and to suppress the non-radiative recombination, thereby improving device stability. Nevertheless, the intrinsic electrically insulating properties of cellulose derivatives still limit the device performance in PSCs.…”