Uniroyal Inc.

Uniroyal Chemical Company, Inc.

Elmar H Jancis

Edward L Wheeler

Franklin H Barrows

Winchester L Hubbard

Rupert A Covey

Robert E Grahame, Jr

Richard A Gencarelli

Paul E Stott

Gerald J Abruscato

Janet D Capolupo

A vinyl aromatic composition stabilized against polymerization comprising (a) a vinyl aromatic compound and (b) an effective amount of a stabilizer system in which the active ingredient consists essentially of an oxygenated species formed by the reaction of oxygen and an N-aryl-N'-alkyl-p-phenylenediamine. Also disclosed is a process for inhibiting the polymerization of vinyl aromatic compounds employing such an oxygenated species.

Stabilized vinyl aromatic composition

Compositions, comprised of a dinitrophenol in an aromatic hydrocarbon solvent, which compositions further comprise a sufficient amount of a phenylenediamine such that a greater amount of dinitrophenol is in solution than would be present in solution if such phenylenediamine were not present, exhibit unexpectedly desirable low temperature stability, and may be diluted with additional solvent to be employed as polymerization inhibitors for vinyl aromatic compounds.

Phenylenediamine solubilizer for dinitrophenol in aromatic solvent

Stabilizing composition comprising (I) a phosphite P(OR).sub.3 and (II) an organic metal salt M(OOCR.sup.1).sub.n, the P/M molar ratio being from 78/1 to 900/1.

Hydrolytically stable antioxidant composition

Novel phenolically substituted esterbisamides as antioxidants useful for the protection of organic materials such as synthetic and natural rubbers, plastics and petroleum products against oxidative degradation.

Phenolic esteramide antioxidants

Novel phenolic oxamide antioxidants for protecting organic materials such as synthetic and natural rubbers, petroleum products, and plastics from oxidative degradation.

Polyfunctional phenolic oxamide antioxidants

An improved method for making 3-(3,5-dialkyl-4-hydroxyphenyl)propionates of hydroxyalkyloxamides involved heating the hydroxyalkyloxamide with a lower alkyl ester of 3-(3,5-dialkyl-4-hydroxyphenyl)propionic acid in the presence of an alkanestannoic acid at a temperature of 150.degree. to 230.degree. C., the lower boiling alcohol being removed by distillation.

Process for making 3-(3,5-dialkyl-4-hydroxyphenyl)propionate esters of

A compound of the formula ##STR1## is useful in protecting organic materials normally subject to oxidative degradation. Among the products benefiting from the incorporation of this phenolic antioxidant are synthetic and natural rubbers, petroleum products and plastics.

9-Thiabicyclo [3,3,1]

A stabilizer suitable for use to protect organic materials into which it is soluble or miscible against oxidative degradation having the general formula ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl or a radical of the structure ##STR2## wherein 'x' represents a tertiary butyl radical.

Hindered phenolic nitro compounds as antioxidants

Catalytic hydrogenation of o-nitrophenylazohydroxyaryls in an alkaline medium yields hydroxyarylbenzotriazoles; under mild conditions an N-oxide is formed. E.g., 6-tert-butyl-2-(5'-chloro-2'-nitrophenylazo)-p-cresol is hydrogenated to 5-chloro-2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)benzotriazole, using platinum sulfide catalyst in the presence of sodium hydroxide: ##STR1## IN THIS CASE A in the starting chemical is 5-chloro, n is 1, Ar is a phenyl nucleus, m is 2, one B is 6-tertbutyl and the other B is 4-methyl; in the product x is zero. Chemicals useful for various purposes, including the stabilization of polymeric materials (e.g., polypropylene, polyvinyl chloride) against light, may be made by the process.

5-Chloro-2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole and

Compounds having either of the structures ##STR1## have strong acaricidal activity, in which R is a phenyl or naphthyl group, or phenyl with certain designated substitution. Thus, mites may be controlled on such crops as cotton by applying such compounds as 2-(1-naphthyl)benzothiazoline or 2-(5-t-butyl-2-hydroxyphenyl)benzothiazole.

Control of acarids using certain benzothiazoles or benzothiazolines

The disclosure relates to a new class of compounds useful in stabilizing organic materials against the effects of heat and light, such materials especially including polymers such as polyolefins. The new compounds are hydrazine complexes of nickel thio-bis-phenolates, where the thio-bis-phenol is of the formula, ##STR1## where R is selected from the group consisting of hydrogen, normal alkyl or normal alkenyl, and R.sub.1 is selected from the group consisting of a normal, secondary, tertiary or cyclic alkyl group. The hydrazines used in making the complexes are of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.4 are independently chosen from the group hydrogen and primary, secondary and tertiary alkyl groups consisting of 1 to 8 carbon atoms and R.sub.3 and R.sub.4 may be joined together to form a heterocyclic structure. The resulting nickel complexes have been found to function as superior stabilizers for organic polymers and for polyolefins in particular, and also to perform synergistically in combination with other stabilizers of the prior art.

Hydrazino nickel thio-bis-phenolates and polyolefins stabilized thereby

Catalytic hydrogenation of o-nitrophenylazohydroxyaryls in an alkaline medium yields hydroxyarylbenzotriazoles; under mild conditions an N-oxide is formed. E.g., 6-tert-butyl-2-(5'-chloro-2'-nitrohenylazo)-p-cresol is hydrogenated to 5-chloro-2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)benzotriazole, using platinum sulfide catalyst in the presence of sodium hydroxide: ##SPC1## In this case A in the starting chemical is 5-chloro, n is 1, Ar is phenyl nucleus, m is 2, one B is 6-tert-butyl and the other B is 4-methyl; in the product x is zero. Chemicals useful for various purposes, including the stabilization of polymeric materials (e.g., polypropylene, polyvinyl chloride) against light, may be made by the process.

Method of making hydroxyarylbenzotriazoles and their N-oxides

Compounds having either of the structures ##SPC1## Have strong acaricidal activity, in which R is a phenyl or naphthyl group, or phenyl with certain designated substitution. Thus, mites may be controlled on such crops as cotton by applying such compounds as 2-(1-naphthyl)benzothiazoline or 2-(5-t-butyl-2-hydroxyphenyl)benzothiazole.

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Naugatuck, CT, United States of America

Elmar H Jancis