Cyano Acrylate Polymers in Medical Applications

Pawar, Rajendra P.; Sarda, Swapnil R.; Borade, Ravikumar M.; Jadhav, Ashok E.; Dake, Satish A.; Domb, Abraham J.

doi:10.2174/1874464810801030186

Cited by 13 publications

(9 citation statements)

References 23 publications

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“…Cyanoacrylates are capable of effectively sealing a wound with an efficient distribution of stress across the entire wound leading to reduced tissue scarring, unlike sutures which tend to leave small gaps in the wound which cause scarring and can act as a route for bacterial infection. A number of review papers on medical applications of cyanoacrylate adhesives have been published (118)(119)(120). More recently, a review of cyanoacrylate adhesives in surgical applications has been published and which gives an overview of the chemistry and clinical applications of medical-grade cyanoacrylate adhesives over the past 50 years (121).…”

Section: Cyanoacrylates In Medical Applicationsmentioning

confidence: 99%

Polycyanoacrylates

Burns

2016

Encyclopedia of Polymer Science and Technology

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Alkyl 2‐cyanoacrylate monomers are commonly used as instant adhesives or “superglue,” mainly because of their unique ability to undergo rapid polymerization under ambient conditions on a wide range of surfaces. This article overviews the chemistry and physical properties of these materials, the most common methods of preparation, their mode(s) of polymerization, and typical performance properties. The main performance limitations of alkyl 2‐cyanoacrylate adhesives, such as poor hot strength and resistance to extreme environments (high heat and humidity) are explained in terms of the susceptibility of the polymer to degradation, and how the chemical structure of the polymer directly affects this degradation process. An overview is given of how the performance properties of cyanoacrylate adhesives are modified through the inclusion of various thickeners for viscosity modification, accelerators for cure acceleration, and recent advances in two component cyanoacrylate adhesives. The uses of polycyanoacrylates in medical adhesive applications and for the preparation of nanoparticles for drug delivery are briefly reviewed.

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Section: Cyanoacrylates In Medical Applicationsmentioning

confidence: 99%

Polycyanoacrylates

Burns

2016

Encyclopedia of Polymer Science and Technology

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“…Once applied to a surface, moisture initiates the liquid alkyl CA monomer to cure within seconds due to rapid anionic polymerization . Smaller CAs such as ethyl 2‐cyanoacrylate (ECA) provide powerful instantaneous bonding between a wide variety of surfaces, including ceramics, plastics, and metals, whereas CAs with longer R‐groups such as n ‐butyl 2‐cyanoacrylate ( n BCA) have greater biocompatibility, and have found use in wound closure, dentistry, and medicine . 2‐Phenylethyl cyanoacrylate (PECA) differs from the previously named two CAs in that it is a solid and is utilized in industrial adhesive tapes and films .…”

Section: Introductionmentioning

confidence: 99%

Reversible addition-fragmentation chain transfer polymerization of alkyl-2-cyanoacrylates: An assessment of livingness

Duffy

Phelan

Zetterlund

et al. 2017

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

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Alkyl 2‐cyanoacrylates (CAs) are primarily used as instant adhesives, including those sold under the Loctite brand. The adhesive action can be inhibited with acid stabilizers allowing radical polymerization to be employed. The following article details the first attempted controlled/living radical polymerization of alkyl CAs: Reversible addition fragmentation chain transfer (RAFT) polymerization mediated by a poly(methyl methacrylate) dithiobenzoate macroRAFT agent for three different CA monomers (ethyl 2‐cyanoacrylate, n‐butyl 2‐cyanoacrylate, and 2‐phenylethyl cyanoacrylate) allowed the preparation of the first block copolymers of this challenging but commercially important monomer class. Nevertheless, GPC with UV detection indicated significant loss of the RAFT end‐group for all three CAs limiting control/living character. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1397–1408

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“…It is clear that the concentration of the biodegradative products is related directly with the biodegradation rate and the reactivity of the repeating units of the cyanoacrylate ester polymers, in such a way that the lower the biodegradation rate the less concentration of toxic byproducts is found in the local point of application . In addition, the biomechanical and physical properties of poly(cyanoacrylate esters) depend on the chemical structure of the repeating monomeric units and specifically of the length of the alkyl ester residue . In order to decrease the toxicity of the cyanoacrylate esters adhesives, several molecules have been extensively studied and some of them have been applied in the surgical practice.…”

Section: Introductionmentioning

confidence: 99%

“…However, the curing reaction and therefore the consequent adhesive properties depend noticeably on the physiological conditions of the zone in which the cyanoacrylate monomer is applied. One important detail is the adhesion of the monomer to the tissues involved in the adhesive processes and in this sense very good works have been published considering the behavior and the clinical interest of the commercial formulations based on these three cyanoacrylate esters (n‐butyl, hexyl, octyl cyanoacrylate) . Octyl cyanoacrylate has been applied widely as a tissue adhesive alternative to other mechanical fixation (sutures) for expanded polytetrafluorethylene membranes and n ‐butyl cyanoacrylate commercialized more than 20 years ago has been applied for the fixation of polypropylene meshes in laparoscopic hernia repair .…”

Section: Introductionmentioning

confidence: 99%

Structural Analysis and Application of n‐Alkyl Cyanoacrylate Surgical Adhesives to the Fixation of Meshes for Hernia Repair

Fernández-Gutiérrez

Rodriguez-Mancheño

Pérez-Köhler

et al. 2016

Macromolecular Bioscience

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The article deals with a comparative analysis of the parameters of the polymerization in physiological conditions of three commercially available alkyl cyanoacrylates, n-butyl cyanoacrylate (GLUBRAN 2), n-hexyl cyanoacrylate (IFABOND), and n-octyl cyanoacrylate (EVOBOND), the cell behavior of the corresponding polymers and the application of these adhesives in the fixation of surgical polypropylene meshes for hernia repair in an animal model of rabbits. The results obtained demonstrate that the curing process depends on the nature of the alkyl residue of the ester group of cyanoacrylate molecules, being the heat of polymerization lower for the octyl derivative in comparison with the hexyl and butyl, and reaching a maximum temperature of 35 °C after a time of mixing with physiological fluids of 60-70 s. The cell behavior demonstrates that the three systems do not present toxicity for fibroblasts and low adhesion of cells, which is a positive result for application as tissue adhesives, especially for the fixation of abdominal polypropylene meshes for hernia repair. The animal experimentation indicates the excellent tolerance of the meshes fixed with the cyanoacrylic adhesives, during at least a period of 90 d, and guarantees a good adhesion for the application of hernia repair meshes.

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Cyano Acrylate Polymers in Medical Applications

Cited by 13 publications

References 23 publications

Polycyanoacrylates

Polycyanoacrylates

Reversible addition-fragmentation chain transfer polymerization of alkyl-2-cyanoacrylates: An assessment of livingness

Structural Analysis and Application of n‐Alkyl Cyanoacrylate Surgical Adhesives to the Fixation of Meshes for Hernia Repair

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