The Upjohn Co.

The Dow Chemical Company

Arco Chemical Technology, L.p.

Benjamin W Tucker

Reinhard H Richter

Henri Ulrich

Debkumar Bhattacharjee

Edward A Barsa

Richard W Oertel

James M O'Connor

Augustin T Chen

Curtis P Smith

Lawrence E Katz

Stephen L Goldstein

Peter J Whitman

William J Farrissey, Jr

Henry G Barnowski, Jr

Willard F Burt

Alexander McLaughlin

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

Disclosed are rigid cellular polyurethanes prepared by bringing together under foam forming conditions an aromatic polyisocyanate and a polyhydric combination comprising a major proportion of a crude polyester polyol and minor proportion of a cross-linking polyol. This selection of particular ingredients gives rise to foams having extremely low initial insulation K factor values.

Rigid polyurethane foams with low thermal conductivities

A novel aliphatic diisocyanate, namely 1,4-bis(2-isocyanatoethyl)cyclohexane, is disclosed. Polyurethanes derived from this diisocyanate exhibit advantageous properties. Illustratively, polyurethane elastomers prepared from the above diisocyanate, a polymeric diol and a low molecular weight diol extender, possess significantly improved resilience properties and are useful in the preparation of automobile bumpers, fenders and the like.

Diisocyanate

1,3-alkylene-diazetidinediones-2,4, wherein alkylene contains at least 8 carbon atoms, are described. These compounds, which can be regarded as intramolecular dimers of alkylene diisocyanates, give rise to the latter on heating. Accordingly, these compounds are useful in a variety of situations in which it is desirable to have a compound which is stable on storage in admixture with other compounds such as polyols, polyamines and the like (which latter would react with a compound containing free isocyanate groups) but which can, at any desired moment, be converted by heating to the free diisocyanate. The latter then reacts with the other component(s) of the mixture to form a polymer. The above compounds are derived by cyclization of the appropriate cyclic allophanoyl halide.

1,3-Alkylene-diazetidine-2,4-diones

The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by utilizing, in association with the polyisocyanate to be used as binder, minor amounts of one or more phosphates or thiophosphates of the formula: ##STR1## where R=alkyl (C.sub.3 and higher), alkenyl (C.sub.3 and higher), aryl, alkyl-substituted aryl, ##STR2## (where R.sub.2 is alkyl, aryl, or alkyl-substituted aryl, A and B are H, methyl, chloromethyl, 2,2,2-trichloromethyl, m=1-25) and lower-alkyl substituted by from 1 to 2 acyloxy groups where acyl is the residue of an aliphatic carboxylic acid having at least 2 carbon atoms; R.sub.1 is Cl, Br, lower-alkoxy, lower-alkylmercapto, arylamino, mono(lower-alkyl)amino, di(lower-alkyl)amino, hydroxy(lower-alkylene)oxy, aryloxy, hydrocarbylureido, and an enol residue; X=O or S and n=1 or 2. The polyisocyanates and the phosphates or thiophosphates are applied to the particles separately, or after preblending one with the other. Whether the components are applied separately or in combination one with the other, they can each be applied either neat or in the form of an emulsion or emulsions.

Process for preparing particle board and polyisocyanate-phosphorus

Novel bis cyclic ureas are disclosed having the formula ##STR1## wherein C.sub.n H.sub.a n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide. The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.

Polyurethane forming compositions

Novel bis cyclic ureas are disclosed having the formula ##STR1## wherein C.sub.n H.sub.2 n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide. The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.

Amide-containing diisocyanates and preparation thereof

A novel process is disclosed for the preparation of cyclic ureas having the formula ##STR1## wherein A is a straight chain alkylene radical of 2 to 4 carbon atoms, inclusive, wherein said alkylene radical can be substituted by at least one member selected from the group consisting of halogen, lower alkyl, lower alkoxy, aryl, aryloxy, aralkyl, and cycloaklyl. An alkylene diamine having the formula NH.sub.2 ANH.sub.2, wherein A is defined as above, is reacted in a solvent with carbonyl sulfide to form the corresponding N-(.omega.-aminoalkyl)thiocarbamic acid (NH.sub.2 ANHCOSH) or zwitterion thereof. The thiocarbamic acid is then heated to form the cyclic urea. The cyclic ureas are useful as cross-linkers and extenders in polyurethane formulations, and those ureas having 4 carbons in the alkylene chain find particular utility in the production of bis cyclic ureas which serve as masked isocyanate compounds in one-component polyurethane elastomer formulations.

Process for the preparation of cyclic ureas

Novel bis cyclic ureas are disclosed having the formula ##STR1## WHEREIN C.sub.n H.sub.2 n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide. The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.

Bis-cyclic ureas

Novel araliphatic diisocyanates having the formula

Araliphatic diisocyanates

A process is described for converting scrap flexible polyurethane foam, derived from a polyether polyol, to a homogeneous mixture of polyols which can be used, alone or as a blend with other polyols, in the preparation of polyurethane foams. The process comprises heating the scrap foam with not more than its own weight of an aliphatic diol which has at least one alkyl substituent in the alkylene chain, and which optionally contains an oxygen atom in the alkylene chain. The scrap flexible foam can contain up to about 75 percent of scrap rigid or semi-flexible foam, if desired.

Growing community of inventors

Bethany, CT, United States of America

Benjamin W Tucker