Chitosan Based Water-Resistant Adhesive. Analogy to Mussel Glue

Abstract

Using analogies from nature, we investigated the possibility that tyrosinase-catalyzed reactions of 3,4-dihydroxyphenethylamine (dopamine) could confer water-resistant adhesive properties to semidilute solutions of the polysaccharide chitosan. Rheological measurements showed that the tyrosinase-catalyzed, and subsequent uncatalyzed, reactions lead to substantial increases in the viscosity of the chitosan solutions. Samples from these high-viscosity modified-chitosans were spread onto dry glass slides, the slides were lapped and clipped together either in air or after being submerged in water, and the bound slides were held under water for several hours. Adhesive shear strengths of over 400 kPa were observed for these modified chitosan samples, while control chitosan solutions conferred no adhesive strength (i.e., the glass slides separated in the absence of measurable forces). High viscosities and water-resistant adhesive strengths were also observed when semidilute chitosan solutions were treated with the known cross-linking agent, glutaraldehyde. Further studies indicate a relationship between the increased viscosities and water-resistant adhesion. These results demonstrate that the renewable biopolymer chitosan can be converted into a water-resistant adhesive.

Removal ofp-Alkylphenols from Aqueous Solutions by Combined Use of Mushroom Tyrosinase and Chitosan Beads

“…This indicates that quinone derivatives enzymatically generated were adsorbed on the chitosan beads. [31][32][33][34] Figure 2 shows the changes in the % conversion, % adsorption, and % removal values with the reaction time for 4NPenP. The quinone derivatives enzymatically generated from 4NPenP were effectively adsorbed on the chitosan beads through nonenzymatic chemical reaction of the quinone derivatives with the chitosan's amino groups.…”

“…The chitosan films turned light brown due to quinone tanning. [31][32][33][34] Figure 6 shows the UV-visible spectra of the chitosan films incubated in the 4NOP and 4NNP solutions containing tyrosinase of 50 U/cm 3 . A broad peak emerged at 350 nm for 4NOP.…”

Biomechanics of byssal threads outside the Mytilidae: Atrina rigida and Ctenoides mitis

“…A wider survey of bivalve byssal thread properties, both within and beyond the orders examined to date, would provide a wealth of information about connections between thread properties and evolutionary patterns within the Bivalvia. Moreover, with further work on byssal thread composition outside the Mytilidae, connections between microscopic molecular structures and macroscopic material properties might suggest new avenues for ongoing biomimetic research (Yu and Deming, 1998;Yamada et al, 2000;Tonegawa et al, 2004;Waite et al, 2005;Lee et al, 2006;Lee et al, 2007;Waite, 2008). Thus the comparative biomechanics of bivalve byssal threads has much to offer to both evolutionary biology and materials engineering.…”

Synthesis and Gelation of DOPA-Modified Poly(ethylene glycol) Hydrogels

“…8 In an effort to duplicate the adhesive characteristics of MAPs in synthetic polymers, several groups have investigated the synthesis of adhesive polymers by incorporation of DOPA into synthetic polymer backbones, side chains, or endgroups. 4,[9][10][11][12][13][14][15][16][17] Yamamoto and co-workers have employed solution synthesis to prepare DOPA-containing polyamino acids, including poly(DOPA) and polypeptide polymers consisting of numerous repeats of DOPA-containing motifs from Mytilus edulis, Aulacomya ater, and the liver fluke Fasciola hepatica. [9][10][11][12] The polymers were found to be water soluble and capable of being cross-linked in the presence of tyrosinase enzyme.…”