1995

A method of preparing an α-cyanoacrylate ester of a desired alcohol includes the steps of preparing a compound which is an α-selenoaryl-α-cyanopropionate ester of the desired alcohol, oxidizing said α-selenoaryl-α-cyanopropionate ester to the corresponding selenoxide, eliminating arylselenic acid from the selenoxide to produce said α-cyanoacrylate ester, and separating said α-cyanoacrylate ester from the selenic acid. At temperatures of about 0 occurs concurrently with the oxidizing step using a peroxide or ozone oxidizing agent.

A process for preparing methyl .alpha.-cyanoacrylate in which methyl cyanoacetate is reacted with formaldehyde to form a polymer, which is subsequently depolymerized to the monomeric product, comprises using an ester of poly(ethylene glycol) as the solvent for the polymerization and depolymerization reactions.

There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate.

A process is described for preparing 2,2,6,6-tetramethylpiperidine-N-oxyl and its 4-position substituted derivatives by oxidation of 2,2,6,6-tetramethylpiperidine and its 4-position substituted derivatives in the presence of hydrogen peroxide and low concentrations of divalent metal salts.

A process for the preparation of 2-cyanoacryloyl chloride in pure form comprises reacting 2-cyanoacrylic acid with a chlorinating agent, said reaction being carried out under side-reaction and polymerisation inhibiting conditions. A preferred chlorinating agent is a volatile chlorinating agent which forms only volatile by-products during the course of the reaction. Suitable volatile chlorinating agents include oxalyl chloride, sulfur oxychloride, trifluoroacetyl chloride and phosgene.

A method for adhesively joining two members includes the steps of mixing non-compressible beads with an adhesive, applying the resulting mixture to one of the members and hemming one member over the other in overlapping relationship. Apparatus for performing this method includes a container for containing a mixture of an adhesive and a plurality of non-compressible beads, an applicator for applying the mixture to one of the members, and hemming means for hemming one member over the other in overlapping relationship.

A method of injection moulding or extruding an article is disclosed in which a ceramic and/or metallic powder is dispersed in a carrier to form a flowable composition. The carrier is preferably a monomeric cyanoacrylate which is reversibly polymerisable so as to yield a solid polymer, which in turn is capable of undergoing a thermally activated depolymerisation reaction so as to yield the monomeric species. The composition is injected into a mould or extruded through a die and the carrier polymerised in the mould or die.

A process is provided for the reversible coupling of weak nucleophiles to the carbon-carbon double bond of 2-cyanoacrylic acid or an ester thereof so as to reversibly protect the bond. Examples of weak nucleophiles include alcohols (including diols and polyols), phenols, sulfur nucleophiles such as thiols and thio acids, phosphorus nucleophiles such as dialkyl or diarylphosphites and phosphines, and carbon nucleophiles such as active methylene compounds.

This invention relates to an improved for preparing a dry powdered adduct of iodine and polymeric 1-vinyl-2-pyrrolidone (hereinafter called polyvinylpyrrolidone) whereby a stable composition is formed which is readily available and germicidally and bactericidally active form which is essentially non-toxic to warm-blooded animals.