The Upjohn Co.

Arco Chemical Technology, L.p.

The Dow Chemical Company

Olin Corporation

Edward A Barsa

Stephen L Goldstein

Fred A Stuber

Benjamin W Tucker

Chung-Yuan Lin

James M O'Connor

Kemal B Onder

Augustin T Chen

Lawrence E Katz

Peter J Whitman

Henry G Barnowski, Jr

Willard F Burt

Philip W Sherwood

Paul V Grosso

Disclosed are new coatings compositions based on an HDI isocyanurate or biuret polyisocyanate and a bis(imine) reaction product of a diaminoalkane containing between two and five carbon atoms with an alkyl aldehyde containing between four and seven carbon atoms (advantageously a bis(imine) product of the reaction of 1,4-diaminobutane and isobutyraldehyde). The latter bis(imine) is completely miscible in HDI isocyanurate and biuret polyisocyanates, and, as a reactive diluent, allows the preparation of high performance coatings formulations that require only small amounts of solvents to achieve a conveniently sprayable viscosity.

Bis(isobutyraldimine) of 1,4-diaminobutane in HDI trimer and

A process for preparing isocyanate adducts having a high proportion of monoisocyanurate using a quaternary ammonium carboxylate trimerization catalyst. Also claimed are specific carboxylate catalysts, together with a process for producing the catalysts. The catalysts are particularly useful for trimerizing hexamethylene diisocyanate and isophorone diisocyanate.

Catalyst and process for producing isocyanate trimers

This invention relates to a multi-step process for isolating a cyclotrimerized isocyanate from mixture containing said cyclotrimerized isocyanate plus an isocyanate oligomer which comprises the steps of: (a) contacting said mixture with a liquid solvent to provide a solvent-containing mixture, (b) extracting said solvent-containing mixture by liquid-liquid extraction to cause said solvent-containing mixture to elute into an extractate and a residue, wherein said extractate is a cyclotrimerized isocyanate that is essentially oligomer-free and is further characterized by having reduced viscosity relative to said solvent-containing mixture, and (c) separating uncyclotrimerized monomer from said extractate to provide a reduced viscosity trimer product that is essentially free of monomer. Also disclosed is the reduced-viscosity product produced by this process.

Process for producing low viscosity isocyanate trimers

Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids of half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids. Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20.degree. C.) which makes the present method particularly suitable to systems for molding polyisocyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.

Thermally activable trimerization catalyst

Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids or half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids. Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20.degree. C.) which makes the present method particularly suitable to systems for molding polyiso-cyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.

Product and process trimerization of organic isocyanates

Described are compounds characterized by the following formula: ##STR1## wherein C.sub.n H.sub.2n is alkylene from 2 to 12 carbon atoms and C.sub.m H.sub.2m is alkylene from 2 to 20 carbon atoms. Each of the alkylene groups can, optionally, be substituted by inert substituents. The compounds contain a free isocyanato group and a masked isocyanate group, namely, the cyclic urea moiety, which, when the compounds are heated, preferably in the presence of a catalyst, opens to give the group OCN--C.sub.n H.sub.2n --. Thus, the compounds can be reacted via the free isocyanate group with active hydrogen-containing monomers or polymers to form storage stable compositions which, upon heating, are curable via reaction with the cyclic urea group.

Compounds, compositions and process

Novel amorphous copolyamides are provided which are the product of reaction of (A) a lactam, (B) a bisimidazoline, and (C) a dicarboxylic acid, wherein the proportions of reactants based on 100 mole percent are from about 43 to about 82 mole percent of lactam (A) and the remaining 18 to 57 mole percent divided between said (B) and said (C) in substantially equimolar proportions. The copolyamides are characterized by better resistance to elevated temperatures than 100 percent polycaprolactam polyamides but at the same time are easily molded because of their amorphous character.

Amorphous copolyamide from lactam, dicarboxylic acid and bisimidazoline

Bis(cyclic ureas) are disclosed which have the formula ##STR1## wherein R is ##STR2## and C.sub.n H.sub.2n is ethylene or 1,3-propylene each of which can be substituted by one or more inert substituents. These compounds are useful as masked diisocyanates which, on heating in the presence of a polyol and, optionally, a polyurethane catalyst, give rise to polyurethane resins. Accordingly, they are useful as a component of storage stable compositions which are convertible to polyurethanes upon heating. Such compositions are particularly useful as solvent-less coating compositions. The properties of the above compounds are distinguished in a number of respects from the known bis(cyclic ureas) in which C.sub.n H.sub.2n has 4 or more carbon atoms in the chain between the valencies. Illustratively, the above compounds are more stable on exposure to heat in the absence of catalysts but, in the presence of polyurethane catalysts, react with polyols at a significantly faster rate than the prior art compounds.

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Cheshire, CT, United States of America

Edward A Barsa