Synthesis and properties of some alkenyl‐ and alkinyl‐2‐cyanoacrylates

Kotzev, Dimiter L.; Novakov, P.; Kabaivanov, V.

doi:10.1002/apmc.1980.050920104

Cited by 12 publications

(4 citation statements)

References 1 publication

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“…For example, Denchev et al report difficulties in depolymerizing oilgo‐allyloxyethyl cyanoacrylate even when it is heated to temperatures in excess of 300 °C 1. Similarly, Kotzev et al were unable to isolate the following cyanoacrylate monomers: 2‐methyl‐2‐propenyl, 2‐butenyl and 1‐propyl‐2‐propenyl83 and Vijayalakshmi et al report difficulties in obtaining tert ‐butyl and undecyl cyanoacrylate 38. Using a molar excess of the cyanoacetate in the condensation step, Denchev et al were able to obtain a more easily depolymerizable product, but the yields were still comparatively low 1…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of four alkyl 2‐cyanoacrylate monomers and their precursors for use in latent fingerprint detection

Tahtouh

Kalman

Reedy

2010

J. Polym. Sci. A Polym. Chem.

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Four novel cyanoacrylates, 2-cyanoethyl 2-cyanoacrylate, 1-cyanoethyl 2-cyanoacrylate, trideuteromethyl 2-cyanoacrylate and pentadeuteroethyl 2-cyanoacrylate have been synthesized using a Diels-Alder protection/deprotection route involving anthracene. The common route for the synthesis of alkyl 2-cyanoacrylates was found to be unsatisfactory for the production of small quantities of the targeted cyanoacrylates, which have potential as reagents for the mid-infrared spectral imaging of fingerprints on difficult surfaces.• the use of acid catalysts for the condensation reaction between alkyl cyanoacetates and formaldehyde [35][36][37][38] • Diels-Alder protection and deprotection [39][40][41][42][43][44][45][46][47][48][49] • esterification of 2-cyanoacryloyl chloride with an alcohol or diol (for bis cyanoacrylates) 50

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of four alkyl 2‐cyanoacrylate monomers and their precursors for use in latent fingerprint detection

Tahtouh

Kalman

Reedy

2010

J. Polym. Sci. A Polym. Chem.

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“…Monomers incorporating cyanoacrylate groups or with an ally! and a cyanoacryl ate group in the molecule have been synthesized [35,36]. These compounds polymerize anionically and crosslink when heated or when exposed to certain polymerization initiators.…”

Section: Development Of Adhesive Bonding Techniquesmentioning

confidence: 99%

“…shown that interfaces cemented with ally 1 cyanoacrylate have improved heat stability compared to less cross-linked cyanoacrylate joints [36]. Formulations incorporating allyl cyanoacrylates and higher alkyl 2-cyanoacryl ates difunctional aromatic diol dimethacrylate esters as well as tri(allyloxy)-s-triazine and peroxide free radical initiators have been suggested…”

Section: Recent Studies Havementioning

confidence: 99%

Properties and interactions of oral structures and restorative materials

Cassel¹,

Tesk²,

Brauer³

et al. 1982

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New polymeric formulations designed to reduce curing shrinkage, residual unsaturation and hydrophi 1 icity in dental composite restorations have been developed and evaluated. To reduce polymerization shrinkage emphasis has been placed on high molecular weight bulky monomers such as blends of BIS-GMA and diurea dimethacrylate types. While typically moderate to fast-acting accelerators such as bis(N ,N-2-hydroxypropyl )ptoluidine or p -tert-butyl -N ,N-dimethylani 1 ine could not be used with such formulations, substitution of slower acting accelerators such as ethyl -4-dimethyl ami nobenzoate or ascorbyl palmitate yielded formulations that set in clinically acceptable times.Powder/liquid, paste/paste or single paste/visible light cured formulations produced composites with

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“…Therefore, the exploration of water-usage chemistry is an important issue to achieve sustainable technologies . Water is already being used as a chemical trigger to induce transformations in materials such as cements − and cyanoacrylates, − which harden after mixing or with contact with water to form robust structures. However, other fundamental chemistry methods for such water-usage technologies are still quite limited, − and there exist considerable areas for development.…”

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confidence: 99%

Lewis Adduct-Dissociating Hydrolysis of Boratrane for Water-Triggered Dehydration of Copolymers with a Hydrophobic Moiety

2022

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As a new example of intrinsically water-triggered phenomena, we report underwater dehydration of the statistical copolymers synthesized from triethanolamine borate (TEAB) methacrylate and styrene (St) induced by the hydrolysis of the pendant TEAB group. TEAB possesses high polarity owing to its internal Lewis adduct structure, which is lost by hydrolysis to triethanolamine (TEA) with a lower dipole moment. Therefore, the hydration of the copolymers became unfavorable through the hydrolysis of the pendant TEAB to TEA, despite polyol formation, and through a hydrophobic interaction based on St moieties becoming alternatively dominant. The dehydration behavior of the copolymers, along with the hydrolysis of the pendant TEAB group, was systematically investigated. The water solubility of the copolymers was found to be dependent on the gradient of the hydrolysis equilibrium of TEAB on the side chains and was the lowest for the TEA state. These findings offer a novel concept toward designing water-responsive materials.

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Synthesis and properties of some alkenyl‐ and alkinyl‐2‐cyanoacrylates

Cited by 12 publications

References 1 publication

Synthesis and characterization of four alkyl 2‐cyanoacrylate monomers and their precursors for use in latent fingerprint detection

Synthesis and characterization of four alkyl 2‐cyanoacrylate monomers and their precursors for use in latent fingerprint detection

Properties and interactions of oral structures and restorative materials

Lewis Adduct-Dissociating Hydrolysis of Boratrane for Water-Triggered Dehydration of Copolymers with a Hydrophobic Moiety

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