Abstract: 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.

Abstract: 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.

Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethyl-phosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorus-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.

Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorus-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.

Abstract: 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.

Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorous-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorus-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.

Abstract: A process is described for the preparation of polymethylene polyphenyl polyamines containing from 40 to 60 percent by weight of diamine and also containing markedly less high molecular weight polyamines than products hitherto available. Phosgenation of the polyamines gives the corresponding mixture of polymethylene polyphenyl polyisocyanates of markedly lower viscosity and lighter color than products hitherto available, and yielding polymer foams which are substantially white in color.The process comprises condensing aniline and formaldehyde (molar ratio 4-10:1) in the absence of catalyst, separating water from the resulting aminal mixture, contacting the aminals at 20.degree. C to 60.degree. C with a solid catalyst (diatomaceous earths, clays, zeolites) until formation of benzylamines is substantially complete, distilling aniline from the resulting benzylamines under reduced pressure and below 150.degree.

Abstract: Novel araliphatic diisocyanates having the formulaOCN(CH.sub.2).sub.3 OArX(CH.sub.2).sub.3 NCOare disclosed wherein X is oxygen or a single bond and Ar is an arylene radical. The araliphatic diisocyanates are prepared from well known and readily obtainable starting materials. When X represents a single bond, the starting material is a monohydric phenol wherein a C-alkylation reaction followed by an O-alkylation reaction with acrylonitrile provides an intermediate dipropionitrile which is converted to the diisocyanate via phosgenation of the corresponding diamine. When X represents oxygen, the starting material is a dihydric phenol wherein O-alkylation with acrylonitrile provides the dipropionitrile which in turn is converted to the diisocyanate via the phosgenation of the corresponding diamine. The diisocyanates find particular utility in the preparation of color and light stable polyurethane products.

Abstract: Aniline and formaldehyde are condensed (2-10 moles aniline per mole of formaldehyde) at ambient temperature in the absence of acid catalysts to give a mixture of aminals (anilinoacetals) and aniline from which the water is removed. The anhydrous aminals are contacted with a solid catalyst (clays, zeolites, diatomaceous earth) using either batch or continuous operation initially at 20.degree. C to 55.degree. C until benzylamine formation is substantially complete, then at 50.degree. C to 65.degree. C until benzylamine conversion to methylene polyphenyl polyamines is 75 - 90% complete and finally at 80.degree. C to 100.degree. C. A polyamine mixture is obtained in which diaminodiphenylmethane is the major (order of 90 percent by weight or higher) component, the bulk of the higher oligomeric polyamines being triamine. The diaminodiphenylmethane component contains of the order of 85 percent of 4,4'-isomer, the rest being 2,4'-isomer except for very small amounts (order of 2 percent or less) of 2,2'-isomer.

Abstract: A process is described for the preparation of polymethylene polyphenyl polyamines containing from 40 to 60 percent by weight of diamine and also containing markedly less high molecular weight polyamines than products hitherto available. Phosgenation of the polyamines gives the corresponding mixture of polymethylene polyphenyl polyisocyanates of markedly lower viscosity and lighter color than products hitherto available, and yielding polymer foams which are substantially white in color.The process comprises condensing aniline and formaldehyde (molar ratio 4-10:1) in the absence of catalyst, separating water from the resulting aminal mixture, contacting the aminals at 20.degree. C to 60.degree. C with a solid catalyst (diatomaceous earths, clays, zeolites) until formation of benzylamines is substantially complete, distilling aniline from the resulting benzylamines under reduced pressure and below 150.degree.

Abstract: A process is described for the selective removal of 2,2'- and 2,4'-diaminodiphenylmethanes from mixtures containing 2,2'-, 2,4'- and 4,4'-diaminodiphenylmethanes and polyamines by heating these mixtures in the presence of aqueous hydrochloric acid (55 to 95 percent by equivalents based on the total amine in the starting material) and formaldehyde. The process is particularly useful to facilitate the isolation of substantially pure 4,4'-isomer from aniline-formaldehyde condensation products. The pure 4,4'-isomer is a valuable intermediate for polyamides as well as for the corresponding diisocyanate. The by-products of the reaction are oligomeric polymethylene polyphenyl polyamines which are also useful as curing agents and intermediates for polymethylene polyphenyl polyisocyanates and the like.

Abstract: A process is described for the selective removal of 2,2'- and 2,4'-diaminodiphenylmethane from mixtures thereof with the corresponding 4,4'-isomer by heating the mixture of isomers in the presence of a 1,3,5-tri-arylhexahydro-1,3,5-triazine and a catalyst (aqueous mineral acid). The process is particularly useful in facilitating the isolation of substantially pure 4,4'-isomer from the aniline-formaldehyde condensation. The pure 4,4'-isomer is a valuable intermediate for polyamides as well as for the corresponding diisocyanate. The by-products of the reaction are oligomeric polymethylene polyphenyl polyamines which are also useful as curing agents and intermediates for polymethylene polyphenyl polyisocyanates and the like.

Abstract: A process is described for the preparation of phospholene-1-oxides and 1-sulfides having an aliphatic substituent in the 1-position, a double bond at the 2- or 3-positions and, optionally, having additional substituents at one or more of positions 2, 3, 4 or 5. The process comprises the reaction of a 1-(2-chloroalkoxy)-phospholene with the appropriate aliphatic alcohol or thiol optionally in the presence of an alkylation catalyst. Use of an aliphatic alcohol gives rise to a phospholene oxide while use of the corresponding thiol gives rise to a phospholene sulfide. The phospholene-1-oxides and 1-sulfides so obtained are useful as catalysts for the conversion of isocyanates to carbodiimides.

Abstract: 2,2'- AND 2,4'-DIAMINODIPHENYLMETHANE ARE SELECTIVELY REMOVED FROM ADMIXTURES THEREOF WITH THE 4,4'-ISOMER BY HEATING THE ISOMER MIXTURE AT 30.degree. TO 100.degree. C in the presence of styrene, .alpha.-alkylstyrenes, or the mono- or diamino nuclear substituted derivatives thereof and a catalyst (mineral acid, clays, diatomaceous earth, zeolites). The styrene or .alpha.-alkylstyrene can be employed as such or generated in situ from a precursor therefor. The process is particularly useful in facilitating the isolation of substantially pure 4,4'-diaminodiphenylmethane from the polyamine mixture obtained by condensation of aniline and formaldehyde.

Abstract: 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.

Abstract: The compounds 4-azidocarbonylphthalic anhydride, 4-isocyanatophthalic anhydride, and the lower-alkyl carbamates obtained by reacting the latter isocyanate with a lower-aliphatic alcohol, are described. A process for the preparation of a polyimide by heating these compounds alone or in admixture with other polyisocyanates is also described. The 4-azidocarbonylphthalic anhydride is an intermediate for the 4-isocyanatophthalic anhydride.