Sulphur containing lubricating oil additives

Claim 2

compound having the formula: ##STR8## wherein in Formula (I) R is a sulfur-bridged hydrocarbon ring derived from 1,3,5-cycloheptatriene or 1,5,9-cyclododecatriene, said sulfur-bridge being a single sulfur bridge between two non-adjacent carbon atoms of said ring forming a bicyclo compound and wherein in Formula (II) R 2 is a polymer comprising the residue of a plurality of n hydrocarbon rings which are derived from 1,3,5-cycloheptatriene, cyclooctatetrene, 1,3-cyclooctadiene, 1,5-cyclooctadiene, 3-alkoxy derivatives thereof and 1,5,9-cyclododecatriene, said n hydrocarbon rings being connected through a sulfur bridge, n being the degree of polymerization such that said compound is oil-soluble, R 1 is the same or different and is an alkyl, alkenyl or aralkyl group and A is a nucleophyllic group selected from ##STR9## wherein R 1 is as above, X is oxygen or sulfur and R 3 is alkyl, aryl, alkaryl or aralkyl.

Claim 3

The compound of claim 1 wherein each R 1 is selected from the group consisting of alkyl and alkenyl groups containing from 1 to 20 carbon atoms.

Claim 4

The compound of claim 1 wherein the group A has the formula: ##STR10## wherein R 1 is as defined in claim 1 and wherein the two groups R 1 may be the same or different.

Claim 5

The compound of claim 1 wherein the group A is selected from the group consisting of groups of the formula --CN and --NCS.

Claim 6

A compound of claim 1 having Formula (I) wherein R is derived from 1,5,9-cyclododecatriene.

Claim 7

A compound of claim 5 wherein R 1 is alkyl.

Claim 8

A compound of claim 6, namely 2,9-bis(butoxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene.

Claim 9

A compound of claim 6, namely 2,9-bis(isopropoxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene.

Claim 10

A compound of claim 6, namely 2,9-bis-(2-ethylhexanoxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene.

Claim 11

A compound of claim 6, namely 2,9-bis-(1-methylbutoxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene

Claim 12

A compound of claim 5, namely 2,9-bis(benzyloxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene.

Claim 13

A compound of claim 1 having Formula I.

Claim 14

A lubricating composition comprising a major amount of a lubricating oil and a minor amount sufficient to improve the antioxidant properties of said oil of an oil-soluble compound of the formula ##STR11## wherein in Formula (I) R is a sulfur-bridged hydrocarbon ring containing from 6-12 carbon atoms wherein said sulfur bridge is a single sulfur bridge between non-adjacent carbon atoms of said ring forming a bicyclo compound and wherein in Formula (II) R 2 is a polymer comprising the residue of a plurality of n hydrocarbon rings containing from 6-12 carbon atoms, said n hydrocarbon rings being connected through a sulfur bridge, n being the degree of polymerization such that said compound is oil-soluble, each R 1 is the same or different and is an alkyl, alkenyl or aralkyl group and A is a nucleophyllic group selected from ##STR12## wherein R 1 is as above, X is oxygen or sulfur and R 3 is alkyl, aryl, alkaryl or aralkyl.

Claim 15

A lubricating composition comprising a major amount of a lubricating oil and a minor amount sufficient to improve the antioxidant properties of said oil of an oil-soluble compound of the formula ##STR11## wherein in Formula (I) R is a sulfur-bridged hydrocarbon ring containing from 6-12 carbon atoms wherein said sulfur bridge is a single sulfur bridge between non-adjacent carbon atoms of said ring forming a bicyclo compound and wherein in Formula (II) R 2 is a polymer comprising the residue of a plurality of n hydrocarbon rings containing from 6-12 carbon atoms, said n hydrocarbon rings being connected through a sulfur bridge, n being the degree of polymerization such that said compound is oil-soluble, each R 1 is the same or different and is an alkyl, alkenyl or aralkyl group and A is a nucleophyllic group selected from ##STR12## wherein R 1 is as above, X is oxygen or sulfur and R 3 is alkyl, aryl, alkaryl or aralkyl.

Claim 16

The lubricating composition of claim 13 containing from 0.01 to 10% by weight of the compound of Formula (I) or (II).

Claim 17

The lubricating composition of claim 13 containing from 0.5 to 3% by weight of the compound of Formula (I) or (II).

Claim 18

A lubricating composition of claim 13 wherein R and R 2 are derived from an unsaturated ring compound selected from the group consisting of 1,3,5-cycloheptatriene, cyclooctatetrene,1,3-cyclooctadiene, 1,5-cyclooctadiene, and 1,5,9-cyclododecatriene.

Claim 19

A lubricating composition of claim 13 wherein said compound has the formula ##STR13## wherein R 1 and A are as defined in claim 13.

Claim 20

A lubricating composition of claim 13 wherein said compound has the formula ##STR14## wherein R 1 is as defined in claim 13.

Claim 21

A lubricating composition of claim 18 wherein said compound is 2,6-bis(butoxythiocarbonylthio)-9-thiabicyclo-(3,3,1)nonane.

Claim 22

A lubricating composition of claim 18 wherein said compound is 2,6-bis(ethoxythiocarbonylthio)-9-thiabicyclo-(3,3,1)nonane.

Claim 23

A lubricating composition of claim 18 wherein said compound is 2,6-bis(isopropoxythiocarbonylthio)-9-thiabicyclo(3,3,1)nonane.

Claim 24

A lubricating composition of claim 18 wherein said compound is 2,6-bis(benzyloxythiocarbonylthio)-9-thiabicyclo(3,3,1)nonane.

Claim 25

A lubricating composition of claim 18 wherein said compound is 2,6-bis(2-ethylhexanoxythiocarbonylthio)-9-thiabicyclo(3,3,1)nonane.

Claim 26

A lubricating composition of claim 13 wherein said compound has the formula ##STR15## wherein R 1 and A are as defined in claim 13.

Claim 27

A lubricating composition of claim 24 wherein said compound has the formula ##STR16##

Claim 28

A lubricating composition of claim 25 wherein said compound is 2,9-bis(butoxythiocarbonylthio)-13-thiabicyclo(8,2,1)tridec-5-ene.

Claim 29

A lubricating composition of claim 13 wherein said compound has Formula I.