The role of local chemical hardness and van der Waals interactions in the anionic polymerization of alkyl cyanoacrylates

Ablat, Hayrensa; Povey, Ian M.; O'Kane, Ruairí; Cahill, Sabine; Elliott, Simon D.

doi:10.1039/c6py00201c

Cited by 7 publications

(2 citation statements)

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“…According to the above, the anionic mechanism of polymerization can be triggered even with very weak nucleophiles such as moisture water [4]. The polymerization reaction is not affected by other molecular phenomena generally, but mainly by the fact that the negative charge of the developing anion is 97% located on the last monomer molecule of the chain [5].…”

Section: Introductionmentioning

confidence: 91%

Thermal Treatment of a Commercial Polycyanoacrylate Adhesive Addressed for Instant Glass Restoration, for Investigating Its Ageing Tolerance

Vouvoudi,

Tamias,

Chatzicharistou

et al. 2023

Macromol

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In the present study, the results of an experimental work on the thermal endurance and decomposition products of the commercial restorative adhesive Loctite® Super Attak Glass, being applied on glass surfaces, are presented. The clarity of the cyanoacrylate polymer and its rapid anionic polymerization reaction are outcomes of the chemistry of the monomer and its activity. First, evaluation of the reversibility of this glue was examined through the solubility tests. It was verified that the adhesive is reversible since it is diluted in several solvents. Later, by applying pyrolysis conjugated with gas chromatography and mass spectrometry (Py–GC/MS), the thermal profile of the polymer is recorded in its neat form and in its aged state (weathered under the influence of UV-irradiation or thermal treatment at 50 and 75 °C). The decomposition products are detected and identified and, finally, possible reactions are investigated. Emphasis is placed on those that could be considered harmful to cultural heritage materials and objects. The fragments by the pyrolytic reactions identified mainly concern esters, less aldehydes and alcohols, small nitrogen compounds, and in some cases unsaturated hydrocarbons with higher molecular weight. Additives such as radical polymerization inhibitors and stabilizers, as well as some plasticizers, were also detected.

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Section: Introductionmentioning

confidence: 91%

Thermal Treatment of a Commercial Polycyanoacrylate Adhesive Addressed for Instant Glass Restoration, for Investigating Its Ageing Tolerance

Vouvoudi,

Tamias,

Chatzicharistou

et al. 2023

Macromol

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“…By comparison, hard materials (e.g., glass, wood, ceramic, and metal) can be bonded by adhesives such as epoxy, cyanoacrylate, and poly(vinyl acetate), each of which has been refined over a long history of development . Such an adhesive comes as a liquid and, after applied between two adherends, forms a hard polymer . The hard polymer withstands high stress, but needs little deformation.…”

Section: Introductionmentioning

confidence: 99%

Molecular Staples for Tough and Stretchable Adhesion in Integrated Soft Materials

Chen

Yang

Bai

et al. 2019

Adv Healthcare Materials

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needs little deformation. These adhesives, however, are in general unsuited to adhere soft materials, because the hard polymers constrain the deformation of the soft materials.Last few years have seen transformative advances in achieving tough and stretchable adhesion between soft materials. Reported methods include surface modification, [27] surface initiation, [28] bulk modification, [29] bulk initiation, [30] bridging polymers, [9] and topological adhesion. [31][32][33] As a prerequisite for tough and stretchable adhesion, each adherend is a tough and stretchable material, typically having at least one covalent polymer network. These methods adhere two soft materials by forming strong, but sparse, connection. Some of these methods form sparse covalent bonds in situ, interlinking the covalent polymer networks of the two soft materials. Other methods form noncovalent complexes in situ, in topological entanglement with the covalent polymer networks of the adherends. Whereas both sparse covalent interlinks and topological adhesion have long achieved tough and stretchable adhesion between dry elastomers, [34,35] the development of these methods for wet soft materials (i.e., synthetic hydrogels and biological tissues) is recent. The recent advances expand the scopes of these methods, enabling tough and stretchable adhesion between various pairs: tissue-tissue, tissue-hydrogel, tissue-elastomer, hydrogel-elastomer, hydrogel-hydrogel, in addition to elastomer-elastomer.Because of the enormous variety of soft materials, applications, and operations (attach, cast, print, coat, brush, and spray), the field remains wide open for inventing methods of tough and stretchable adhesion. [2] The covalent interlinks require complementary functional groups from the adherends, and the formation of some of these covalent interlinks requires toxic agents and special processing conditions. The noncovalent topological adhesion is tough and stretchable, but detaches easily in response to environmental stimuli, an attribute which can be either useful or limiting. [32,33] A recent work shows that cyanoacrylates (commonly known as superglues), once diluted in an organic solvent and spread between two soft materials, can form tough and stretchable adhesion between the two soft materials. [36] Even though the mechanism of this tough and stretchable adhesion is unclear, its implication is important. In addition to adhering hard polymers, cyanoacrylates have long been usedThe integration of soft materials-biological tissues, gels, and elastomersis a rapidly developing technology of this time. Whereas hard materials are adhered using adhesives of hard polymers since antiquity, these hard polymers are generally unsuited to adhere soft materials, because hard polymers constrain the deformation of soft materials. This paper describes a design principle to use hard polymers to adhere soft materials, such that adhesion remains tough after the adhered soft materials are subject to many cycles of large stretches in the plane of their interface. The tw...

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Cyanoacrylates

Fink¹

2018

Reactive Polymers: Fundamentals and Applications

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The role of local chemical hardness and van der Waals interactions in the anionic polymerization of alkyl cyanoacrylates

Abstract: The polymers are stabilized appreciably by intra-chain dispersion forces. Localization of negative charge imparts sufficient local hardness for polymerization to continue independently of chain length.

Cited by 7 publications

References 40 publications

Thermal Treatment of a Commercial Polycyanoacrylate Adhesive Addressed for Instant Glass Restoration, for Investigating Its Ageing Tolerance

Thermal Treatment of a Commercial Polycyanoacrylate Adhesive Addressed for Instant Glass Restoration, for Investigating Its Ageing Tolerance

Molecular Staples for Tough and Stretchable Adhesion in Integrated Soft Materials

Cyanoacrylates

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