Journal Article

2 alkyl cyanoacrylates are acrylic monomers of high use as industrial and domestic adhesives (crazy glue), or as surgical adhesives. In the literature it has been described the interaction among these monomers and peptidic compounds, but it has not been identified the chemical structure at the interface. Another group of authors detected kinetic incompatibilities with the anionic polymerization mechanism. In the present work, it was possible to identify a product as a result of the acid hydrolysis of the monomer.

The effect of allyl derivatives of muconic, malonic, and isocyanuric acids, as well as some other unsaturated compounds on the properties of adhesives based on ethyl- and allyl-α-cyanoacrylates, is studied.

The results of studies of the effect of synthesized modifiers based on cyanosorbic acid on the ther- mal properties of cyanoacrylate adhesives have been presented.

Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels−Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis.

Superhydrophobic surfaces hold great promise in a variety of appli- cations where the extreme water repellency can lead to novel properties and functionalities. Most of the existing techniques, however, require multi-step and laborious procedures as well as are only applicable to certain substrates. We present a facile one-step (“paint-like”) method for creating superhydrophobic porous polymer coatings. The approach is based on the anionic polymerization of octyl cyanoacrylate in the presence of aqueous ethanol. This leads to the formation of a highly porous superhydrophobic polymer film.

A simple and more environmentally friendly procedure than that traditionally used was developed for preparation of esters consisting in acrylic acid addition to bicyclo[2.2.1]hept-2-ene and its 5-alkyl derivatives. The acrylates obtained were subjected to hydrogenetion followed by hydrolysis of propionic acid esters. A number of new compounds was obtained; some among them possess a pleasant odor.

A new material for the microencapsulation of biological systems was discovered and characterized with regards to the effects of reaction conditions on product yield. By using poly(cyanoacrylate ester), membrane microcapsules were produced with sufficient strength and porosity to be effective in a process environment for the immobilization and protection of encapsulated material. After synthesizing numerous monomeric cyanoacrylate esters, the n-butyl derivative was discovered to give the best results with regards to microcapsule formation.

A study was conducted to investigate the differences in reactivity between ethyl cyanoacrylate (ECA) with phosphines and amines, which contain different alkyl substituents. It was found that when an equimolar amount of dimethylphenylphosphine and ECA react, a stable zwitterion is formed. This is the first time the proposed initiating species for alkyl cyanoacrylate polymerization has been sufficiently stable to be isolated and fully characterized spectroscopically.

Alkyl propiolate couples with itself in the presence of catalytic DABCO under very mild conditions to provide a quantitative yield of E-hex-2-en-4-yne dioates. Hydrogenation of these enyne dioates using Lindlar catalyst provides the corresponding E,Z-diene dioate, a common structural motif found in an array of natural products.

Unsaturated carboxylic acids such as meth- acrylic acid, crotonic acid, vinylacetic acid, and sorbic acid and aromatic carboxylic acids reacted with terminal ace- tylenes in the presence of a catalytic amount of bis(05- cyclooctadieny1)ruthenium-P-n-Bui3n benzene a t 80 "C to give enol esters having a terminal methylene group in excellent yields with high regioselectivity.