Abstract: The present invention relates generally to substantially liquid, chlorine-free, sulfur-bridged phenols useful as antioxidants and more specifically to the preparation of a substantially liquid, chlorine-free, sulfur-bridged, hindered phenol compositions which are effective antioxidant(s) in lubricating oils without causing excessive copper corrosion. The invention also includes lubricating oils containing an antioxidant additive of the present invention, as well as a method of reducing oxidation in the lubricating oil used in a machine such as an internal combustion engine.

Abstract: A sulfurized, phenolic antioxidant having a low chlorine content and good copper corrosion properties is prepared by reacting a partially sulfurized mixture of reactive, hindered phenols with formaldehyde or formaldehyde and an amine.

Abstract: Fuel compositions contain a liquid, partially-sulfurized, hindered phenol antioxidant composition prepared by reacting a liquid mixture of phenols which contains at least 50 weight percent of one or more reactive hindered phenols with sulfur monochloride in proportions to provide from about 0.3 to 0.7 gram atoms of sulfur monochloride per mole of reactive, hindered phenol.

Abstract: A reduced metal content lubricant contains the reaction product of a phosphosulfurized polyalkene and an amine, a polyalkene substituted phenol, and, optionally, a polyalkene sulfonate.

Abstract: A partially sulfurized, phenolic antioxidant having good copper corrosion properties is prepared by reacting a liquid mixture of phenols, which mixtures includes at least one reactive, hindered phenol, with sulfur chloride in proportions to provide from about 0.3 to 0.7 gram atoms of sulfur per mole of reactive phenol.

Abstract: Fuel compositions contain a liquid, sulfur-bridged, hindered phenol antioxidant composition prepared by reacting a mixture of hindered phenols with a sulfur chloride in the presence of a polar modifier.

Abstract: Compounds having the formula: ##STR1## wherein: a. R is an organic radical selected from an alkyl group, an alkenyl group, an aryl group or an aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms;b. R.sup.1 is hydrogen or an organic radical selected from an alkyl group or alkenyl group, an aryl or aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms; and,R.sup.2 and R.sup.3 are the same or different alkyl groups containing from 1 to 32, more preferably 4 to 8, carbon atoms eachare effective antiwear and antioxidant additives in lubricating oil.

Abstract: A liquid, sulfur-bridged, hindered phenol antioxidant composition is prepared by reacting a mixture of hindered phenols with a sulfur chloride in the presence of a polar modifier. The composition is an effective antioxidant in lubricating oils without causing excessive copper corrosion.

Abstract: Compounds having the formula: ##STR1## wherein: a. each of R, R.sup.2 and R.sup.4 when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms, an aryl group containing from 6 to about 15 carbon atoms or a cycloalkyl group containing from 4 to about 10 carbon atoms;b. each of R.sup.1 and R.sup.3 when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms; an aryl group containing from 6 to about 15 carbon atoms; a cycloalkyl group containing from 4 to about 10 carbon atoms or an alkenyl group containing from 2 to about 10 carbon atoms or R.sup.1 and R.sup.3 taken together form the group --CHYCY.dbd.CY-- in which Y is a hydrogen atom or a methyl group or R.sup.1 together with R.sup.2 form an alkylidene group containing from 1 to about 6 carbon atoms;c. R.sup.5 is a hydrogen atom or an alkyl group containing from 1 to about 15 carbon atoms;d. R.sup.

Abstract: Compounds having the formula: ##STR1## wherein: a. R is an organic radical selected from an alkyl group, an alkenyl group, an aryl group or an aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms;b. R.sup.1 is hydrogen or an organic radical selected from an alkyl group or alkenyl group, an aryl or aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms;c. R.sup.2 and R.sup.3 are the same or different alkyl groups containing from 1 to 32, more preferably 4 to 8, carbon atoms eachare effective antiwear and antioxidant additives in lubricating oil.

Abstract: Compounds having the formula: ##STR1## wherein: a. each of R, R.sup.2 and R.sup.4 when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms, an aryl group containing from 6 to about 15 carbon atoms or a cycloalkyl group containing from 4 to about 10 carbon atoms;b. each of R.sup.1 and R.sup.3 when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms; an aryl group containing from 6 to about 15 carbon atoms; a cycloalkyl group containing from 4 to about 10 carbon atoms or an alkenyl group containing from 2 to about 10 carbon atoms or R.sup.1 and R.sup.3 taken together form the group --CHYCY.dbd.CY-- in which Y is a hydrogen atom or a methyl group of R.sup.1 together with R.sup.2 form an alkylidene group containing from 1 to about 6 carbon atoms;c. R.sup.5 is a hydrogen atom or an alkyl group containing from 1 to about 15 carbon atoms;d. R.sup.

Abstract: Compounds or mixtures of compounds having the formulae: ##STR1## wherein R is an alkyl group containing from 1 to 20 carbon atoms, n represents a number selected from the class consisting of zero and the integers from 1 through 6, R' represents a member selected from the group consisting of the hydrogen atom and those groups represented by R and R" is an aliphatic hydrocarbon group are effective antiwear and antioxidant additives in lubricating oils.

Abstract: Lubricating oils having improved antioxidant and anti-wear properties are obtained by adding a minor amount of a reaction product made by reacting at least one aliphatic olefinically unsaturated hydrocarbon containing from about 8 to 36 carbon atoms (preferably an .alpha.-olefin) concurrently with sulfur and at least one fatty acid ester (preferably an oil such as cottonseed oil) to obtain a reaction intermediate and reacting this intermediate with additional sulfur and a dimer of cyclopentadiene or lower C.sub.1-4 alkyl substituted cyclopentadiene dimers, such as methylcyclopentadiene dimer.

Abstract: A sulfurized olefin of improved solubility in lubricating oil is made by reacting sulfur monochloride with a monoolefin (e.g. isobutylene) to form an adduct which is reacted with sodium sulfide, sodium hydrosulfide, sulfur and alkyl mercaptan (e.g. tert-butyl mercaptan) in an aqueous alcohol reaction medium.

Abstract: A metal deactivator especially useful in lubricating oil is made by reacting 2,5-dimercapto-1,3,4-thiadiazole, an olefin and sulfur dichloride in the mole ratio of about 1:0.9-2.5 0.9-2.5.