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US 5,205,947 AGranted
Dispersant additives comprising amine adducts of dicarboxylic acid monoepoxy thiol reaction products
AssigneeExxon Chemical Patents Inc.
InventorsJacob Emert, Robert D. Lundberg
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Abstract
The present invention is directed to an oil-soluble lubricating oil additive comprising at least one adduct of (A) a polyolefin of 700 to 5,000 number average molecular weight substituted with carboxylic acid producing moieties (preferably acid or anhydride moieties), and (B) a monoepoxy thiol.
Claims36
An oil soluble dispersant adduct useful as a lubricating oil dispersant prepared by a process which comprises:
- (a) contacting (i) a long chain hydrocarbyl polymer-substituted C.sub.4 to C.sub.10 dicarboxylic acid producing material formed by reacting an olefin polymer of C.sub.2 to C.sub.10 monoolefin having a number average molecular weight of about 700 to 5,000 and a C.sub.4 to C.sub.10 monounsaturated dicarboxylic acid material, said acid producing material having an average of at least about 0.7 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material;
- and (ii) a monoepoxy thiol, for a time and under conditions sufficient to form a first adduct monoepoxy hemi-thioester of said dicarboxylic acid producing material, and
- (b) contacting said first adduct with at least one amine nucleophilic reagent for a time and under conditions sufficient to form said dispersant adduct.
A process for producing a dispersant useful as a lubricating oil additive which comprises:
- (a) providing along chain hydrocarbyl polymer-substituted C.sub.4 to C.sub.10 dicarboxylic acid producing material formed by reacting an olefin polymer of C.sub.2 to C.sub.10 monoolefin having a number average molecular weight of about 700 to 5,000 and a C.sub.4 to C.sub.10 monounsaturated dicarboxylic acid material, said acid producing material having an average of at least about 0.7 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material;
- (b) providing at least one monoepoxy thiol of the formula:
- ##STR50## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are H, hydrocarbyl or thiol-substituted hydrocarbyl, with the proviso that at least one of the R.sup.1, R.sup.2, R.sup.3 and R.sup.4 groups comprises thiol-substituted hydrocarbyl;
- (c) contacting said acid producing material with said monoepoxy thiol in a monoepoxy thiol:acid producing material molar ratio of not greater than about 10:1 under conditions sufficient to effect reaction of at least a portion of the thiol groups on said monoepoxy thiol compound with at least a portion of the acid-producing groups in said acid producing material, to form a monoepoxy hemi-thioester of said acid producing material;
- and
- (d) contacting said monoepoxy hemi-thioester with at least one amine nucleophilic reagent for a time and under conditions sufficient to form said dispersant adduct.
3 more elements
A process for producing a dispersant useful as a lubricating oil additive which comprises:
- (a) providing a long chain hydrocarbyl polymer-substituted C.sub.4 to C.sub.10 dicarboxylic acid producing material formed by reacting an olefin polymer of C.sub.2 to C.sub.10 monoolefin having a number average molecular weight of about 700 to 5,000 and a C.sub.4 to C.sub.10 monounsaturated dicarboxylic acid material, said acid producing material having an average of at least about 0.7 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material;
- (b) providing at least one monoepoxy thiol of the formula:
- ##STR51## wherein n is an integer of from 1 to 4, R.sup.1, R.sup.4, M.sup.1 M.sup.2, M.sup.3, M.sup.4, M.sup.5 and M.sup.6 are the same or different and are H, hydrocarbyl or thiol-substituted hydrocarbyl, and wherein one or more of M.sup.1, M.sup.3 and M.sup.6 can further comprise --SH, with the proviso that at least one of R.sup.1, R.sup.4, M.sup.1, M.sup.2, M.sup.3, M.sup.4, M.sup.5 and M.sup.6 comprises thiol-substituted hydrocarbyl;
- (c) contacting said acid producing material with said monoepoxy thiol in a monoepoxy thiol:acid producing material molar ratio of not greater than about 10:1 under conditions sufficient to effect reaction of at least a portion of the thiol groups on said monoepoxy thiol compound with at least a portion of the acid-producing groups in said acid producing material, to form a monoepoxy hemi-thioester of said acid producing material;
- and
- (d) contacting said monoepoxy hemi-thioester with at least one amine nucleophilic reagent for a time and under conditions sufficient to form said dispersant adduct.
3 more elements
Dependencies are inferred from the claim text.