Single-Phase Photo-Cross-Linkable Bioinspired Adhesive for Precise Control of Adhesion Strength

Harper, Tristan; Slegeris, Rimantas; Pramudya, Irawan; Chung, Hoyong

doi:10.1021/acsami.6b14599

Cited by 29 publications

(24 citation statements)

References 46 publications

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“…It is important to note that poly(MDOPA 15 ‐ co ‐SBMA 85 ‐ co ‐PEGDMA 3.5 ) was a stiff gel‐like substance, resulting in poor contact with the porcine skins. As briefly discussed in the introduction, an ideally crosslinked adhesive displays strong resistance to internal energy dissipation and crack propagation during the debonding process . In particular, lightly crosslinking in pressure‐sensitive adhesives reduces internal motion of polymer matrix resulting in prevention of the failure of the polymer matrix during the debonding process .…”

Section: Resultsmentioning

confidence: 99%

“…The average molecular weight of PEGDMA (purchased from Sigma‐Aldrich) used as crosslinker is 750 g mol −1 . MDOPA 1 was synthesized and characterized as previously reported in the literature . Porcine skin was purchased from a local grocery store.…”

Section: Methodsmentioning

confidence: 99%

“…MDOPA 1 was synthesized and characterized as previously reported in the literature. 26,27,52 Porcine skin was purchased from a local grocery store. Porcine intestine was donated from a local slaughter house.…”

Section: Methodsmentioning

confidence: 99%

“…Excessively crosslinked polymers, however, may lose their flexibility, leading to poor initial interfacial contact between the adhesive and the target surface. For these reasons, finding an ideal degree of crosslinking is a critical step in the design of effective polymer adhesives …”

Section: Introductionmentioning

confidence: 99%

“…For these reasons, finding an ideal degree of crosslinking is a critical step in the design of effective polymer adhesives. 19,21,26,27 Another important requirement of an effective polymeric adhesive is a suitable base polymer for desirable biomedical applications. In this study, we utilize a zwitterionic polymer, poly(sulfobetaine methacrylate) (polySBMA), as a base polymer, occupying that 85 mol % of the entire terpolymer adhesive structure.…”

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confidence: 99%

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Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing

Kim

Ondrusek

Lee³

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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In this report, we have developed a new bioinspired medical adhesive capable of providing a leak‐proof barrier for application to intestinal anastomoses. The newly synthesized adhesive is a terpolymer possessing three different repeating units: (1) A zwitterionic polymer, poly(sulfobetaine methacrylate) (polySBMA), for increased hydrophilicity and biocompatibility, (2) a 3,4‐dihydroxy‐L‐phenylalanine (DOPA) segment which contains the catechol group, and (3) poly(ethylene glycol) dimethacrylate (PEGDMA) for light crosslinking, which will be used to strengthen the polymer adhesion properties by providing debonding resistance. The chemical structure of the terpolymer, poly(N‐methacryloyl‐3,4‐dihydroxyl‐L‐phenylalanine‐co‐sulfobetaine methacrylate‐co‐poly(ethylene glycol) dimethacrylate) (poly(MDOPA‐co‐SBMA‐co‐PEGDMA)), synthesized following a convenient and reproducible radical polymerization was clearly confirmed by 1H NMR. The terpolymer adhesive displayed the optimal adhesion properties when containing 1.5–2.5 mol % of crosslinker, PEGDMA, according to the measured maximum adhesion strength and work of adhesion, characterized by lap shear strength tests utilizing porcine skin. The adhesive did not show cytotoxicity when tested with human embryonic kidney (HEK293A) cells. Ex vivo anastomosis experiments using porcine intestine demonstrated that the new poly(MDOPA‐co‐SBMA‐co‐PEGDMA) is a promising biomedical adhesive which successfully prevents leakage from the sutured intestinal tissue. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1564–1573

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing

Kim

Ondrusek

Lee³

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Debondable, Recyclable and/or Biodegradable Naturally‐Based Adhesives

Jarach

Dodiuk

2023

Biobased Adhesives

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The Cross‐Linking Mechanism and Applications of Catechol–Metal Polymer Materials

Yan

Peng

Shen

et al. 2021

Adv Materials Inter

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Since then, lots of researches have been carried out to reveal the role of catechol in mussel adhesion behavior and devoted to incorporating the catechol functionality into synthetic materials. [7,8] Especially, catechol-metal-based materials have garnered considerable attention due to the strong interactions, diverse properties, and tunable structures. [9,10] Despite the interaction between catechol and metal ions is still not fully understood, significant progress has been made and many possible mechanisms have been proposed. The cross-linking process relies on versatile catechol-based chemistry.The synthetic catechol-metal-based materials usually exhibit excellent performance such as good adhesion, flexibility, conductivity, and high mechanical strength. [10][11][12] A wide consensus in relevant fields is that the type of metal ions is the main factor determining the properties of these materials. [13,14] This discovery raises the interest in exploring the unknown scientific and technical to synthetic novel catechol-metal-based functional materials. For example, the introduction of transition metal ions triggers efficient interactions with the catechol-containing groups. In the systems, the metal ions can act as chemical stimuli, cross-linking points, and tunable chelation ability. [15] As a typical example, iron ions (i.e., Fe 2+ and Fe 3+ ) have an obvious effect on the coordination between metal ions and catechol groups. [16][17][18] In previous reports, many researchers have focused on the specific introduction of various metal ions into the catechol-metal system. [19,20] It provided a new opportunity for various applications, such as water purification, biomedical engineering, wearable device, and responsible sensor.Besides, various chemical structures of catechol, including natural plant-derived phenols (e.g., dopamine, gallic acid, tannic acid (TA), and lignin) [21][22][23] and synthetic phenolic molecules (e.g., polyphenol and poly-catechol), [24] is still a subject of debate. Over 8000 articles about catechol-containing chemistry have been published and lead to numerous breakthroughs in the fields of chemistry and materials. In catecholmetal systems, phenolic compounds display diverse properties, such as metal coordination, antioxidant activity through Catechol plays an important role in many systems by interacting with organic (e.g., amino acids) and inorganic (e.g., metal ions, metal oxides) compounds. Catechol cross-linked polymer networks exhibit significant mechanical strength, good adhesiveness, and life-like characteristics. Recently, catechol-metal coordination materials have aroused increasing interest in multifunctional applications. Numerous influential studies have demonstrated that the type of metal ions and the structure of phenolic (such as natural phenolic (e.g., tannic acid, gallic acid, and lignin) or synthetic catechol-containing polymers) play important roles in the formation of catechol-metal coordination complexes. Although catechol-metal-based materials have been successfully pr...

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Single-Phase Photo-Cross-Linkable Bioinspired Adhesive for Precise Control of Adhesion Strength

Cited by 29 publications

References 46 publications

Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing

Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing

Debondable, Recyclable and/or Biodegradable Naturally‐Based Adhesives

The Cross‐Linking Mechanism and Applications of Catechol–Metal Polymer Materials

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