The isolation of a zwitterionic initiating species for ethyl cyanoacrylate (ECA) polymerization and the identification of the reaction products between 1°, 2°, and 3° amines with ECA

Klemarczyk, Philip

doi:10.1016/s0032-3861(00)00618-2

Cited by 43 publications

(24 citation statements)

References 9 publications

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“…2c ). The polymerization reaction was terminated through the formation of the fibers, probably as a consequence of the complete evaporation of DMSO and of proton and hydroxide transfer from water molecules of the environment 22 25 27 28 .…”

Section: Resultsmentioning

confidence: 99%

Zwitterionic Nanofibers of Super-Glue for Transparent and Biocompatible Multi-Purpose Coatings

Mele

Heredia‐Guerrero

Bayer

et al. 2015

Sci Rep

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Here we show that macrozwitterions of poly(ethyl 2-cyanoacrylate), commonly called Super Glue, can easily assemble into long and well defined fibers by electrospinning. The resulting fibrous networks are thermally treated on glass in order to create transparent coatings whose superficial morphology recalls the organization of the initial electrospun mats. These textured coatings are characterized by low liquid adhesion and anti-staining performance. Furthermore, the low friction coefficient and excellent scratch resistance make them attractive as solid lubricants. The inherent texture of the coatings positively affects their biocompatibility. In fact, they are able to promote the proliferation and differentiation of myoblast stem cells. Optically-transparent and biocompatible coatings that simultaneously possess characteristics of low water contact angle hysteresis, low friction and mechanical robustness can find application in a wide range of technological sectors, from the construction and automotive industries to electronic and biomedical devices.

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Section: Resultsmentioning

confidence: 99%

Zwitterionic Nanofibers of Super-Glue for Transparent and Biocompatible Multi-Purpose Coatings

Mele

Heredia‐Guerrero

Bayer

et al. 2015

Sci Rep

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“…A zwitterionic reaction product from the reaction between ethylcyanoacrylate and a phosphine, such as dimethyl phenylphosphine, was isolated and characterized spectroscopically (18). The isolated zwitterion was used to initiate polymerization of ethyl cyanoacrylate (ECA) when added to an excess of ECA monomer.…”

Section: Polymerization Of Cyanoacrylatesmentioning

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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“…if a neutral, nucleophilic molecule is involved, the reaction is referred to as a zwitterionic polymerization (Pepper, 1978) (Scheme 5.4). A zwitterion from the reaction between an equimolar amount of ethyl cyanoacrylate and dimethyl phenylphosphine has actually been isolated and characterized spectroscopically (Klemarczyk, 2001). this zwitterion will initiate ethyl cyanoacrylate polymerization, if it is added to an excess of the cyanoacrylate monomer.…”

Section: Chemistrymentioning

confidence: 99%