The Upjohn Co.

The Dow Chemical Company

Olin Corporation

Arco Chemical Technology, L.p.

Fred A Stuber

Kiran B Chandalia

Chung-Yuan Lin

Adam Gregg Malofsky

James M O'Connor

Henri Ulrich

Visweswara R Durvasula

Edward A Barsa

Michael M Martinez

George H Temme

Peter J Whitman

Floro F Frulla

Michael J Morgan

Sheng-Hong A Dai

Gerret M Peters, Jr

Durvasula V Rao

The present invention relates to a process for coating a substrate which comprises (a) contacting said substrate with a low volatility organic (so-called 'low VOC') coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one polyisocyanate, a solvent in an amount of between 0% and 45% by weight based upon the amount of said polyisocyanate in said composition, and an trimerization catalyst, said composition being essentially free of any volatile mono- and di-isocyanates, to form a coating on said substrate, and (b) heating said coating to a curing temperature of between 120.degree. F. and 350.degree. F. for a curing time of between about ten minutes and about six hours in order to cure said coating by trimerizing at least some of the isocyanate groups of the polyisocyanate to provide a heat-cured coating on said substrate. Also claimed is the coating composition itself.

Low VOC, heat-curable, one-component and two-component coating

This invention relates to one-component and two-component heat-curable or moisture-curable coating compositions, and processes for their use in providing a slippery coating on a substrate utilizing a polyisocyanate-based low VOC coating composition, employing a fluoro-containing active hydrogen-containing compound, and which is suitably rapidly hardened under the influence of heat or moisture.

Low VOC, fluorocompound-containing one-component and two-component

This invention relates to a process for coating a substrate other than polyvinyl chloride which comprises contacting said substrate with a fast drying, moisture curable, low volatility organic coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one polyisocyanate, a solvent in an amount of between 0% and 45% by weight based upon the amount of said polyisocyanate in said composition, and a tertiary amine catalyst, said composition being essentially free of any volatile mono- and di-isocyanates, and said composition being moisture curable upon exposure to atmospheric moisture. Also claimed is the coating composition itself.

Low VOC, fast drying, moisture curable, one-component isocyanate-based

Disclosed is a class of poly(aminoaromatic) compounds (I) obtained by capping polymeric polyols or polythiols iwth aromatic amine groups wherein the latter groups are linked by --O-- or --S-- to the polyol (polythiol) residues. Also disclosed are the precursor poly(nitroaromatic) compounds (II) from which the compounds (I) are derived. The polyamines are characterized by amine reactivities in respect of isocyanate polyaddition reactions which allows for polymer reaction rates that are intermediate of prior art related polyamine compounds. Accordingly, the compounds (I) find their prime utility in the formation of synthetic resins containing polyurea linkages.

Polyurea resins from poly(aminoaromatic) compounds

Disclosed is a class of poly(aminoaromatic) compounds (I) obtained by capping polymeric polyols or polythiols with aromatic amine groups wherein the latter groups are linked by --O--or --S--to the polyol (polythiol) residues. Also disclosed are the precursor poly(nitroaromatic) compounds (II) from which the compounds (I) are derived. The polyamines are characterized by amine reactivities in respect of isocyanate polyaddition reactions which allows for polymer reaction rates that are intermediate of prior art related polyamine compounds. Accordingly, the compounds (I) find their prime utility in the formation of synthetic resins containing polyurea linkages.

Capping of polyols with aromatic amines

An improved process for the production of organic polyisocyanate-based molded polymers prepared from at least one organic polyisocyanate and at least one polyol wherein there is employed an internal mold release agent comprising an amino-polysiloxane having at least one group of the formula

Process for the production of organic polyisocyanate-based molded

Disclosed is an improved process for the production of organic polyisocyanate-based molded polymers prepared from at least one organic polyisocyanate and at least one polyol wherein there is employed an internal mold release agent comprising an amino-polysiloxane having at least one group of the formula

Product

Disclosed is an improved process for the preparation of carbamates by heating an organic carbonate and an aromatic urea or polyurea in the presence of aluminum as catalyst and a promoter comprising a combination of iodine and a mercury salt. High reaction temperatures are avoided by the process and conversions to carbamate products are high. Additionally, the process is economically attractive because even the common aluminum foil can be used as the catalyst. The products prepared by the process can be used in the production of insecticides, and, particularly, as intermediates in the preparation of organic mono- and polyisocyanates.

Preparation of carbamates from organic carbonates and aromatic ureas

Disclosed is an improved process for the preparation of carbamates by heating an organic carbonate and an aromatic amine in the presence of aluminum as catalyst and a promoter comprising a combination of iodine and a mercury salt. High reaction temperatures are avoided by the process and conversions to carbamate products are high. Additionally, the process is economically attractive because even the common aluminum foil can be used as the catalyst. The products prepared by the process can be used in the production of insecticides, and, particularly, as intermediates in the preparation of organic mono- and polyisocyanates.

Preparation of carbamates

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.

Preparation of polyurethane from bis(cyclic urea) and polymeric polyol

Bis(cyclic ureas) monomer compositions useful in making polyurethane

Cyclohexylbenzene and dicyclohexylbenzenes are converted to the corresponding hydroperoxides in the presence of t-butyl, cumene, or p-diisopropylbenzene hydroperoxides and a free radical initiator. The use of the combination of hydroperoxide and free radical initiator enables the reaction to be carried out at lower temperatures (80.degree.-105.degree. C.) than can be employed with hydroperoxides or free radical initiators alone and gives high (90%) selectivity and good conversion (20% or higher).

Process for the autoxidation of cyclohexylbenzene to form

An improved process for the nitration of aromatic hydrocarbons is described. The aromatic hydrocarbon (benzene, toluene of particular interest) is reacted with gaseous nitrogen dioxide in the presence of a catalytic amount of sulfuric acid and in the absence of oxygen. The process is highly selective and avoids the formation of undesired by-products. The acid employed as catalyst can be recovered and recycled after removal of water of condensation liberated in the reaction.

Process for nitrating aromatic hydrocarbons

Cycloalkanones (C.sub.5-12) are converted to the corresponding 1,2-cycloalkanediones by autoxidation in the presence of a base catalyst (potassium t-butoxide preferred) and a polar organic solvent.

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North Haven, CT, United States of America

Fred A Stuber