Abstract: Production of alkyl substituted aromatic diamines by reacting triethlyaluminum with an aromatic diamine and a chloride ion source in the presence of an olefin is disclosed. The alkyl substituted aromatic diamines are useful as chain extenders in polyurethane processes.

Abstract: Production of alkyl substituted aromatic diamines by reacting triethylaluminum with an aromatic diamine and a chloride ion source in the presence of an olefin is disclosed. The alkyl substituted aromatic diamines are useful as chain extenders in polyurethane processes.

Abstract: Mono-ar-tert-butyl toluenediamine is selectively made by heating a mixture of toluenediamine and an aluminum halide of the formula R.sub.n AlX.sub.3-n or R.sub.3 Al.sub.2 X.sub.3 wherein n is 0, 1 or 2 and R is an alkyl containing 1-10 carbon atoms to 150.degree.-225.degree. C. and reacting the mixture with isobutylene at 500-300 psig until the yield of mono-ar-tert-butyl toluene is at or near maximum. Minor amounts of di-tert-butyl toluenediamines which form and are difficult to separate can then be lowered by venting the reaction and continuing to heat at about 130.degree.-200.degree. C. until the di-tert-butyl components are decreased to the desired level forming additional mono-ar-tert-butyl toluenediamine.

Abstract: A process for monoalkylating 1-alkyl-2,4-diaminobenzene or 1-alkyl-2,6-diaminobenzene. Propylene is reacted with 2,4-diaminotoluene in the presence of aluminum anilide catalyst. Aniline is an optional ingredient.

Abstract: A process for monoalkylating 1-alkyl-2,4-diaminobenzene or 1-alkyl-2,6-diaminobenzene. Propylene is reacted with 2,4-diaminotoluene in the presence of aluminum anilide catalyst. Aniline is an optional ingredient.

Abstract: A polyamine mixture formed from formaldehyde, an ortho-alkylaniline, and an ortho,ortho-dialkylaniline. The polyamine mixture is prepared by heating one of the anilines with formaldehyde, mixing the other aniline with an acid catalyst, and slowly adding the former to the latter. The mixtures are useful as chain extenders in polyurethane processes including reaction injection molding. The novel mixtures give unexpected mold gel and set times as compared to corresponding unmixed compounds formed from a single aniline or formed by previous typical condensation reactions. Also, the proportion of polyamines made by the novel mixtures may be varied to give excellent physical characteristics.

Abstract: A process for monoalkylating 1-alkyl-2,4-diaminobenzene or 1-alkyl-2,6-diaminobenzene. Propylene is reacted with 2,4-diaminotoluene in the presence of aluminum anilide catalyst. Aniline is an optional ingredient.

Abstract: Methyl groups on N-methyl aromatic amines are redistributed to ring positions by heating in contact with an aluminum anilide catalyst and a nickel, cobalt, molybdenum or titanium-containing cocatalyst. For example, N-methyl-o-toluidine forms a mixture containing substantial quantities of 2,6-dimethylaniline, 2,4-dimethylaniline, and 2,4,6-trimethylaniline.

Abstract: Methyl groups on o-methyl aromatic amine are redistributed to ortho positions by heating in contact with an aluminum anilide catalyst and a nickel, cobalt, molybdenum or titanium-containing cocatalyst. For example, o-toluidine forms a mixture containing an aniline, o-toluidine, 2,6-dimethylaniline, and 2,4-dimethylaniline.

Abstract: Polyurethanes can be produced using dihydroxyaromatic compounds as chain extenders. Preferred polyurethanes of this type are RIM (reaction injection molding) molded products or cast elastomers. The dihydroxyaromatic compounds are preferably selected from:I. dihydroxybenzenes and alkyl-substituted dihydroxybenzenes wherein the alkyl groups have up to about 6 carbon atoms and the total number of carbon atoms in the alkyl groups in said alkyl-substituted dihydroxybenzene is up to about 12 carbon atoms, andII. alkylene bridged, alkyl-substituted bisphenols wherein the alkylene bridge contains up to about 6 carbon atoms and the total number of carbon atoms in the alkyl groups attached to each benzenoid nucleus is at least one but does not exceed about 12;said dihydroxyaromatic compounds being further characterized by having no more than one tert-alkyl group on a position adjacent to any hydroxy group.

Abstract: An improvement in the process for alkylating the nucleus of an aromatic amine which contains small amounts of a nickel compound by reaction with an olefin in the presence of an aluminum anilide-type catalyst whereby hydrogen sulfide or a sulfide generating compound (e.g. thioacetamide) is added to the aromatic amine to reduce the rate inhibiting effect of the nickel compound.

Abstract: Ortho-cyclopentyl-hydroxybenzyl sulfides (e.g. di-(3,5-dicyclopentyl-4-hydroxybenzyl)sulfide) are effective antioxidants.

Abstract: Methylenebis(dicyclopentyl phenols) in which at least one cyclopentyl group is ortho to the phenolic hydroxy group are effective antioxidants in a broad range of organic materials including mineral and synthetic lubricating oil and polyolefins.