Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive

Kaur, Sukhmanjot; Narayanan, Amal; Dalvi, Siddhesh; Liu, Qianhui; Joy, Abraham; Dhinojwala, Ali

doi:10.1021/acscentsci.8b00526

Cited by 77 publications

(95 citation statements)

References 81 publications

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“…The CFPs are also capable of the adhesion at wet or underwater situations, although the bonding strength is much lower because of the formation of hydrated cation layers. [ 17 ] White and Wilker [ 18 ] and Joy and co‐workers [ 19,20 ] incorporated monomers with electrostatic charges or aliphatic pendants into CFPs, achieving underwater bonding strength of 0.4 MPa on aluminum and 0.65 MPa on glass, respectively. By adjusting the polarity [ 21 ] or the hydrophilicity [ 22 ] of CFP backbones, Wan et al reported improved bonding strength of 1.13 and 1.33 MPa on glass substrates.…”

Section: Methodsmentioning

confidence: 99%

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Sha

Zhang

et al. 2020

Macromol. Rapid Commun.

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crosslinking [2,3] and metal ion chelation processes. [4,5] Thus, up to now, great efforts have been made to incorporate DOPA or catechol groups in a broad range of designed polymers to get mussel-inspired adhesives, which showed good bonding performances both at dry and underwater conditions. These polymers were generally named as "catecholfunctionalized polymers" (CFPs).Up to now, notable accomplishments have been achieved by using CFPs for high performance adhesion at atmospheric environment. Yu and Deming and co-workers reported the synthesis of DOPA-containing copolypeptides, exhibiting a bonding strength of 4.0 MPa on aluminum. [6] Wilker et al. synthesized poly[(3,4-dihydroxystyrene)-co-styrene] via anionic polymerization method, which achieved a bonding strength of 11 MPa on aluminum by using CaCO 3 particles as reinforcing materials. [7] Subsequently, they also incorporated the CFPs with poly(lactic acid) [8][9][10] or pendant oligo(ethylene glycol) moieties [4] to produce biodegradable/biocompatible adhesives with good dry-state bonding strength. Wan et al. synthesized catechol-functionalized poly(vinyl alcohol) via esterification reactions [11] and acetal formation reactions, [12] exhibiting bonding strengths of 4.0 MPa on glass and 14.9 MPa on stainless steel, respectively. Kaneko et al. synthesized a hyperbranched CFP via thermal polycondensation reaction between 3,4-dihydroxycinnamic acid and 4-hydroxycinnamic acid, which showed a bonding strength of ≈10 MPa on steel. [13] Then, they also prepared a similar hyperbranched polymer system with the bonding strength on steel up to 15 MPa. [14] However, despite great progress, the bonding strength of most reported CFPs on metal substrates is smaller than 15 MPa. Recently, Messersmith and co-workers [15] and Detrembleur and co-workers [16] separately reported the synthesis of catechol-functionalized polybenzoxazines and polyhydroxyurethanes, which were used to prepare thermoset adhesive materials with excellent bonding strength of 20.5 MPa on aluminum and 22.1 MPa on stainless steel, respectively. To our knowledge, these two polymers represent the best adhesive materials among CFPs for dry-state adhesion on metal Marine mussels have the ability to cling to various surfaces at wet or underwater conditions, which inspires the research of catechol-functionalized polymers (CFPs) to develop high-performance adhesive materials. However, these polymeric adhesives generally face the problems of complex synthetic route, and it is still high challenging to prepare CFPs with excellent adhesive performance both at dry and underwater conditions. Herein, a mussel-inspired alternating copolymer, poly(dopamine-alt-2,2-bis(4-glycidyloxyphenyl) propane) (P (DA-a-BGOP)), is synthesized in one step by using commercially available monomers through epoxy-amino click chemistry. The incorporation of polar groups and rigid bisphenol A structures into the polymer backbone enhances the cohesion energy of polymer matrix. The alternating polymer structure endows the polymers with high...

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Section: Methodsmentioning

confidence: 99%

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Sha

Zhang

et al. 2020

Macromol. Rapid Commun.

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“…[9] The commercially available epoxy resins [10] and polyurethanes [11] are reported to demonstrate strong underwater adhesion, but long time of curing is usually required. [15][16][17] The finding of universality of catechol chemistry for wet adhesion has provided a valuable biomimetic source to develop diverse adhesives for use in aqueous environments. [5,12] In addition, electrostatic and hydrophobic interactions were also proved to contribute to enhanced underwater adhesion, but the adhesion strength was relatively poor.…”

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confidence: 99%

“…[13,14] In nature, many organisms, such as mussels, barnacles, and castle worms, have evolved an unparalleled mechanism to perfectly tackle the underwater adhesion problem. [15][16][17] The finding of universality of catechol chemistry for wet adhesion has provided a valuable biomimetic source to develop diverse adhesives for use in aqueous environments. However, several problems, such as the complexity of administration, release of harmful organic solvents, [18,19] long-term curing, [2] need for oxidant addition, [20,21] and low adhesion strength, [18,22] may hamper the actual applications of these bioinspired adhesives.…”

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confidence: 99%

Water‐Triggered Hyperbranched Polymer Universal Adhesives: From Strong Underwater Adhesion to Rapid Sealing Hemostasis

et al. 2019

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is greatly decreased or even eliminated. For instance, the widely used cyanoacrylate adhesives exhibit strong adhesion in air, but when applied in water environment, they are hardened quickly to form a layer of stiff plastics, eventually resulting in the loss of adhesion. [9] The commercially available epoxy resins [10] and polyurethanes [11] are reported to demonstrate strong underwater adhesion, but long time of curing is usually required. Recently, host-guest chemistry strategy was reportedly employed to prepare underwater adhesives; however, the substrate surface needs to be modified in advance. [5,12] In addition, electrostatic and hydrophobic interactions were also proved to contribute to enhanced underwater adhesion, but the adhesion strength was relatively poor. [13,14] In nature, many organisms, such as mussels, barnacles, and castle worms, have evolved an unparalleled mechanism to perfectly tackle the underwater adhesion problem. [15][16][17] The finding of universality of catechol chemistry for wet adhesion has provided a valuable biomimetic source to develop diverse adhesives for use in aqueous environments. However, several problems, such as the complexity of administration, release of harmful organic solvents, [18,19] long-term curing, [2] need for oxidant addition, [20,21] and low adhesion strength, [18,22] may hamper the actual applications of these bioinspired adhesives. Although numerous dopamine-based adhesives have been reported and shown to bond various material surfaces, strong adhesion in water and particularly blood environment, remains nonexistent so far.Increasing studies on bioadhesives secreted by molluscs and insects have suggested that liquid coacervation plays a critical role in achieving underwater adhesion. [13] In this process, phase separation and concurrently increased hydrophobicity induced by coacervation can dispel the hydrated water on the interface, leading to much enhanced interaction of adhesive groups with the adherent and thus stable underwater adhesion. Up to date, several complex coacervate adhesives with linear structure have been reported, but the occurrence of those coacervations in water needs external triggers, such as temperature, [13] pH, [20,23] and iron strength. [24] Compared to linear counterparts, hyperbranched polymer (HBP) has a unique highly branched Despite recent advance in bioinspired adhesives, achieving strong adhesion and sealing hemostasis in aqueous and blood environments is challenging. A hyperbranched polymer (HBP) with a hydrophobic backbone and hydrophilic adhesive catechol side branches is designed and synthesized based on Michael addition reaction of multi-vinyl monomers with dopamine.It is demonstrated that upon contacting water, the hydrophobic chains selfaggregate to form coacervates quickly, displacing water molecules on the adherent surface to trigger increased exposure of catechol groups and thus rapidly strong adhesion to diverse materials from low surface energy to high energy in various environments, such as deionized water, sea ...

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“…After several washouts, the SEM images shown in Figure 4d confirmed that MSNs‐TA@PDA‐Zn nanocomposites have excellent adhesion performance, which was due to an abundance of catechol groups in PDA, and they interacted with substrate through hydrogen bonding. [ 40 ] This could effectively prevent the pesticide particles from rolling off. This behavior was similar to those reported in previous studies.…”

Section: Resultsmentioning

confidence: 99%

Adhesive Nanocomposite for Prolonging Foliar Retention and Synergistic Weeding and Nourishing

Huang

Yan

et al. 2020

Advanced Sustainable Systems

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efficiency of fertilizer and pesticide is growing to solve these problems. [8][9][10] Controlled release pesticide-fertilizer combination (CRPFC), playing a synergistic effect of pesticide and fertilizer, is an effective approach to achieve sustainable circulative agriculture and has garnered considerable attention all over the world. [11,12] Compared with traditional controlledrelease pesticide or fertilizer, CRPFC unifies the two most important agrochemicals used in agriculture, and combine the plant protection of pesticide and the nutrients supply of fertilizer into one field operation. It cannot only save labor but also reduce time and energy consumption. Various materials have been developed recently to be used as carriers of pesticide and fertilizer, such as organic polymers, [13] bio-sourced matrices, [14] and inorganic materials. [15,16] However, most of them only provide individual function and are accompanied by complex preparation processes. Furthermore, they are very susceptible to being washed away by rain, which limit their real applications. [17] Therefore, develop an adhesive carrier for extensive use of CRPFC in agriculture is still a challenge.Nanotechnology represents a new direction for the carrier development. [18][19][20][21] Over the past years, the applications and benefits of nanotechnology, especially nanoparticles as pesticide or fertilizer carrier platforms, have generated immense developments. [22][23][24] Recently, mesoporous silica nanoparticles (MSNs) show superior performance as support for fertilizer or pesticide controlled release due to their easy functionalization modification, controllable morphology, adjustable pore volume, and thermal stability. [25][26][27][28][29] However, the adsorption capacity of MSNs was a great limitation because there are no functional sites on MSNs surface. [30] It was reported that by grafting highdensity carboxyl groups onto the pore surface of MSNs and complexing with platinum atoms, the drug loading efficiency of MSNs can be greatly improved. [31] In this work, MSNs functionalized by positive charges were developed to achieve a high loading capacity of pesticide and fertilizer (Scheme 1). Then the nanoparticles were coated by polydopamine (PDA) via self-polymerization. [32][33][34] As a kind of catecholamines, PDA is expected to be active for metals ions, [35] The volatilization and leaching for most fertilizers and pesticides raise questions about the sustainability of ecosystems. To enhance the utilization of fertilizers and pesticides, pesticide-fertilizer combined nanocomposites are developed to prolong foliar retention and play a synergistic effect of weeding and nourishing for plant growth. The pesticide-fertilizer combined nano composites are prepared based on positive-charge functionalized mesoporous silica and polydopamine, by chelating micronutrients (Zn 2+ ) and loading pesticide 2,4-D. A high loading capacity of Zn 2+ (233.4 mg g −1 ) and 2,4-D (17.8%) is achieved. Zn 2+ and the pesticide show excellent pH-responsive release behavio...

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Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive

Cited by 77 publications

References 81 publications

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Water‐Triggered Hyperbranched Polymer Universal Adhesives: From Strong Underwater Adhesion to Rapid Sealing Hemostasis

Adhesive Nanocomposite for Prolonging Foliar Retention and Synergistic Weeding and Nourishing

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