The Goodyear & Tire Rubber Company

Budd H Sturm

Joseph A Kuczkowski

Paul Harry Sandstrom

George Frank Balogh

Roger J Hopper

Joseph Frank Geiser

Dane Kenton Parker

Joel Muse

Thomas J Slam

The present invention relates to a process for the preparation of unsubstituted and alkyl-substituted diaryl-phenylenediamines.

Process for the preparation of unsubstituted and substituted diaryl

The present invention relates to a composition which exhibits antiozonant activity in diene containing rubbers comprising the reaction product of a multi-step process comprising:

High molecular weight amine containing antiozonants

The present invention relates to polymerizable esters containing derivatives from p-hydroxydiphenylamine which are useful in the stabilization of oxidizable organic materials such as rubber, oils and the like.

Ester derivatives from p-hydroxydiphenylamine

The present invention relates to thioesters having the structural formula: ##STR1## wherein R.sup.x is selected from the group of formulae consisting of: ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group of radicals consisting of hydrogen or methyl; R.sup.4 and R.sup.5 are independently selected from the group of radicals consisting of hydrogen, alkyls having 1 to 18 carbon atoms, aryls having 6 to 10 carbon atoms, aralkyls having 7 to 9 carbon atoms, and radicals of the formula: ##STR3## and R.sup.6 is selected from the group of radials consisting of alkyls having 1 to 24 carbon atoms, aryls having 6 to 12 carbon atoms and aralkyls having 7 to 12 carbon atoms. These thioesters are particularly useful as a synergist for conventional phenolic and amine antioxidants.

Thioesters and antioxidant compositions containing the same

This invention is concerned with compounds of the structural formula: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different radical selected from the group consisting of hydrogen and methyl radicals; when R.sup.1 is a hydrogen radical, R is an alkyl radical of 5 to 11 carbon atoms; when R.sup.1 is a methyl radical, R is a radical of 4 to 10 carbon atoms; when R.sup.2 is a hydrogen radical, R.sup.3 is an alkyl radical of 5 to 11 carbon atoms; when R.sup.2 is a methyl radical, R.sup.3 is an alkyl radical of 4 to 10 carbon atoms. These compounds have utility as synergists for phenolic type and amine type antioxidants in the stabilization of natural and synthetic rubbers.

Methylene bis(alkylsulfides) as antioxidant synergists in rubber

This invention is concerned with the stabilization of oxidizable organic materials such as rubbers, oils, plastics and the like through the addition of an autosynergistic phenolic antioxidant reaction product to the oxidizable organic material. More specifically, this invention is directed to a definitive process for the preparation of an alkylated phenol/formaldehyde/mercaptan reaction product comprising the simultaneous acid catalyzed reaction of specific reactants at specific molar ratios under azeotroping conditions and the use of the reaction product in oxidizable organic materials.

Autosynergistic phenolic antioxidant reaction product

There is disclosed a process for the synthesis of para-nitrodiphenylamines via the Formanilide Process wherein the improvement is characterized in that a specific catalyst is utilized. More specifically, a zinc (II) compound (zinc in the plus two oxidation or valence state), is used as a catalyst in the preparation of para-nitrodiphenylamines via the formanilide process.

Para-nitrodiphenylamine synthesis

There is disclosed a process for the synthesis of para-nitrodiphenylamines wherein the improvement is characterized in that a specific co-catalyst system is utilized. More specifically, a zinc (II) compound (zinc in the plus two oxidation or valence state), is used in conjunction with copper or a copper compound as a co-catalyst system in the preparation of para-nitrodiphenylamines.

There is disclosed a novel class of vulcanization accelerators, specifically compounds such as 2-(isopropylsulfinyl)-benzothiazole.

Preparation of 2-(isopropylsulfinyl)benzothiazole

Vulcanization of rubber with 2-(alkylsulfinyl)-benzothiazoles

Processes for synthesizing para-nitrodiphenylamines whereby a para-halonitrobenzene is reacted with an aromatic amine selected from the group consisting of formanilides and anilines (substituted and unsubstituted) in the presence of a basic material (to remove acid) are improved by the incorporation of certain select solubilizing agents into the reaction medium. These solubilizing agents are linear, branched, or cyclic polyethers. Some of the resulting advantages are: higher reaction yield, less by-products, and a faster reaction.

Para-nitrodiphenylamines synthesis using Polyethers and macrocyclic

There is disclosed the method of preparing photographic grade hydroquinone from technical grade hydroquinone which consists of treating a solution of the technical grade hydroquinone in the presence of a palladium catalyst with hydrogen while the hydroquinone solution is at a pH between about 3 and about 6.

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Hartville, OH, United States of America

Budd H Sturm