Novel polymer substituted amino phenol mannich base amido-amine dispersant additives (PT-742)

Claim 2

A lubricating oil dispersant additive useful in oleaginous compositions which comprises a condensation product obtained by the reaction of: (a) at least one polymer substituted mono- or dicarboxylic acid material comprising polymer substituted with at least monounsaturated dicarboxylic acid moieties selected from the group consisting of C 4 to C 10 monounsaturated dicarboxylic acid producing moieties, and C 3 to C 10 monounsaturated monocarboxylic acid producing moieties, wherein said polymer has a number average molecular weight of from about 300 to 10,000; (b) at least one N-hydroxyaryl amine compound; (c) at least one aldehyde reactants; and (d) at least one amido-amine or a thioamido-amine comprising a reaction product of at least one polyamine and an alpha, beta-unsaturated compound of the formula; ##STR36## wherein X is sulfur or oxygen Y is --OR 8 , --SR 8 or NR 8 (R 9 --) wherein R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl.

Claim 3

The dispersant additive according to claim 1, wherein said polyamine comprises amines containing from 2 to 60 carbon atoms and from 2 to 12 nitrogen atoms per molecule.

Claim 4

The dispersant additive according to claim 2, wherein said polyamine comprises a polyalkylenepolyamine wherein each said alkylene group contain 2 to 6 carbons and said polyalkylenepolyamine contains from 5 to about 9 nitrogen atoms per molecule.

Claim 5

The dispersant additive according to claim 1, wherein said hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material comprises polyisobutylene of about 900 to 4000 number average molecular weight substituted with succinic anhydride moieties, said polyamine comprises polyalkylenepolyamine wherein each said alkylene group contain 2 to 6 carbons and said polyalkylenepolyamine contains 5 to 9 nitrogen atoms per molecule, and said alpha, beta-unsaturated compound comprises at least one member selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.

Claim 6

The dispersant additive according to claims 1 or 4, wherein said polyamine comprises polyethylenepolyamine or polypropyleneamine.

Claim 7

The dispersant additive according to claims 1 or 4, wherein said dispersant is borated to provide from about 0.05 to 2.0 weight percent boron in the borated dispersant.

Claim 8

The dispersant additive according to claims 1 or 4, wherein said olefin polymer comprises polyisobutylene.

Claim 9

The dispersant additive of any one of claims 1 to 4, wherein the ratio of acid producing moieties per molecule of olefin polymer in said dispersant is from about 1.05 to 1.8.

Claim 10

The dispersant additive of claim 8, wherein said number average molecular weight of said olefin polymer is from about 1300 to 3000.

Claim 11

The dispersant additive of claim 1, wherein said monounsaturated acid material comprises maleic anhydride.

Claim 12

The dispersant additive according to claims 1 or 4 wherein about 1 to 5 moles of said acid producing material per primary nitrogen equivalent of said amido-amine are present in said reaction mixture.

Claim 13

The dispersant additive according to claims 1 or 4 wherein said polyamine contains an average of at least 2 primary nitrogen atoms per molecule, said X group is oxygen and said polyamine and said alpha, beta-unsaturated compound are contacted in an amount of from about 3 to 5 equivalents of said polyamine (based on said primary amine content) per mole of said alpha, beta unsaturated compound.

Claim 14

The dispersant additive according to claim 12 wherein said amido-amine contains an average of from 1 to 3 amido groups per molecule of said amido-amine.

Claim 15

The dispersant additive according to claims 1 or 4 wherein said polyamine contains an average of at least 2 primary nitrogen atoms per molecule, said X group is sulfur and said polyamine and said alpha, beta-unsaturated compound are contacted in an amount of from about 3 to 5 equivalents of said polyamine (based on said primary amine content) per mole of said alpha, beta unsaturated compound.

Claim 16

The dispersant additive according to claim 14 wherein said amido-amine contains an average of from 1 to 3 amido groups per molecule of said amido-amine.

Claim 17

The dispersant additive according to claim 1 wherein said N-hydroxyaryl amine compound comprises at least one member selected from the group consisting of compounds of the formula: H.sub.2 N--Ar--OH wherein Ar represents ##STR37## and wherein r" is 1 or 2, and derivatives thereof wherein from 1 to 3 ring carbon atoms are each substituted by an alkyl group or halogen atom.

Claim 18

The dispersant additive according to claim 4 wherein said N-hydroxyaryl amine compound comprises at least one member selected from the group consisting of compounds of the formula: ##STR38## in which T', is hydrogen, alkyl having from 1 to 3 carbon atoms or halogen.

Claim 19

The dispersant additive according to claim 12 wherein the Ar group is phenyl.

Claim 20

A concentrate containing from about 3 to 45 weight percent of the dispersant additive of claim 1.

Claim 21

A concentrate containing from about 10 to 35 weight percent of the dispersant additive of claim 2.

Claim 22

A lubricating oil composition containing from about 0.1 to 20 weight percent of the dispersant additive of claims 1 or 2.

Claim 23

A lubricating oil composition containing from about 0.1 to 20 weight percent of the dispersant additive of claim 13.

Claim 24

A process for producing a lubricating oil dispersant additive useful in oleaginous compositions which comprises: (i) providing a carbonyl-amino material obtained by reacting (a) at least one polymer substituted mono- or dicarboxylic acid material comprising polymer substituted with C 4 to C 10 monounsaturated dicarboxylic acid producing moieties, or C 3 to C 10 monounsaturated monocarboxylic acid moieties, wherein said polymer has a number average molecular weight of from about 300 to 10,000; with (b) at least one N-hydroxyaryl amine compound, to form said carbonxyl-amino material; (ii) providing an amido-amine or thioamido-amine compound comprising a reacting product of at least one polyamine and an alpha, beta-unsaturated compound of the formula: ##STR39## wherein X is sulfur or oxygen, Y is --OR 8 , SR 8 or --NR 8 --(R 9 --), wherein R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (iii) contacting said carbonyl-amino material with (c) at least one aldehyde reactant; and (d) said amino-amine or thioamide-amine reactant for a time and under conditions sufficient to form said dispersant additive.

Claim 25

A process for producing a lubricating oil dispersant additive useful in oleaginous compositions which comprises: (i) providing a carbonyl-amino material obtained by reacting (a) at least one polymer substituted mono- or dicarboxylic acid material comprising polymer substituted with C 4 to C 10 monounsaturated dicarboxylic acid producing moieties, or C 3 to C 10 monounsaturated monocarboxylic acid moieties, wherein said polymer has a number average molecular weight of from about 300 to 10,000; with (b) at least one N-hydroxyaryl amine compound, to form said carbonxyl-amino material; (ii) providing an amido-amine or thioamido-amine compound comprising a reacting product of at least one polyamine and an alpha, beta-unsaturated compound of the formula: ##STR39## wherein X is sulfur or oxygen, Y is --OR 8 , SR 8 or --NR 8 --(R 9 --), wherein R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (iii) contacting said carbonyl-amino material with (c) at least one aldehyde reactant; and (d) said amino-amine or thioamide-amine reactant for a time and under conditions sufficient to form said dispersant additive.

Claim 26

The process of claim 23 wherein said polymer comprises polybutylene.

Claim 27

The process of claim 24 wherein said polymer has a number average molecular weight of from about 700 to about 5,000.

Claim 28

The process of claim 25 wherein said number average molecular weight is between about 1,300 and 3,000.

Claim 29

The process according to claim 23 wherein said polyamine contains from 2 to 60 carbon atoms and from 2 to 12 nitrogen atoms per molecule.

Claim 30

The process according to claim 27 wherein said polyamine comprises a polyalkylenepolyamine wherein each said alkylene group contains 2 to 6 carbons and said polyalklylenepolyamine contains from 2 to about 9 nitrogen atoms per molecule.

Claim 31

The process according to claim 28 wherein said polyamine comprises polyethylenepolyamine.

Claim 32

The process according to claim 23 wherein said hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material comprises polyisobutylene of about 900 to 5000 number average molecular weight substituted with succinic anhydride moieties, said polyamine comprises polyalkylenepolyamine wherein each said alkylene group contain 2 to 6 carbons and said polyalkylenepolyamine contains 5 to 9 nitrogen atoms per molecule, and said alpha, beta-unsaturated compound comprises at least one member selected from the group consisting of methyl acrylate, methyl methacrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.

Claim 33

The process according to claim 23 wherein said N-hydroxyaryl amine compound comprises at least one member selected from the group consisting of compounds of the formula: H.sub.2 N--Ar--OH wherein Ar represents ##STR40## and wherein r" is 1 or 2, and derivatives thereof wherein from 1 to 3 ring carbon atoms are each substituted by an alkyl group or halogen atom.

Claim 34

The process according to claim 30 wherein said N-hydroxyaryl amine compound comprises at least one member selected from the group consisting at compounds of the formula: ##STR41## in which T' is hydrogen, alkyl having from 1 to 3 carbon atoms or halogen.

Claim 35

The process according to claim 32 wherein the Ar group is phenyl.

Claim 36

The process according to claim 33 wherein said N-hydroxyaryl amine compound comprises 4-aminophenol.

Claim 37

A lubricating oil dispersant additive useful in oleaginous compositions which comprises a Mannich Base condensation product obtained by the steps of: (i) providing a N-hydroxyaryl amine-containing Mannich base intermediate obtained by reacting at least one N-hydroxyaryl amine compound, at least one aldehyde reactant and at least one amino-amine or thioamido-amine reactant, said N-hydroxyaryl amine-containing Mannich, base intermediate comprising at least one compound selected from the group consisting of: (a) adducts of the structure, H--(A--A')x.sub.1 --Ar'A'--A--(A'Ar"a"a)x.sub.2 --(A'Ar')x.sub.3 --H wherein x 1 is 0 or 1, x 2 is an integer of 0 to 8, x 3 is 0 or 1, A is a bivalent bis(N-terminated) amino group derived from said amine reactant and contains from 2 to 60 carbon atoms and from 2 to 11 nitrogen atoms, A' comprises the group --CH(T") wherein T" is H or alkyl of from 1 to 9 carbon atoms and is derived from the said aldehyde reactant, and Ar' comprises the moiety; ##STR42## wherein Ar represents ##STR43## and wherein r" is 1 or 2, and derivatives thereof wherein from 1 to 3 ring carbon atoms are each substituted by an alkyl group or halogen atom, wherein T' is H, alkyl of 1 to 3 carbons or halogen, and (b) adducts of the structure: ##STR44## wherein T', A', Ar and A are as defined above, and "a" is an integer of 1 to 2; and said amido-amine and thioamido-amine reactant comprising a reaction product of at least one polyamine and an alpha, beta-unsaturated compound of the formula: ##STR45## wherein X is sulfur or oxygen, Y is --OR 8 , --SR 8 or --NR 8 (R 9 ), wherein R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (ii) contacting said N-hydroxyalkyl amine-containing Mannich base intermediate with (a) at least one polymer substituted mono- or dicarboxylic acid material comprising polymer substituted with C 4 to C 10 monounsaturated dicarboxylic acid producing moieties or C 3 to C 10 monounsaturated monocarboxylic acid moieties, wherein said polymer has a number average molecular weight of from about 300 to 10,000, for a time and under conditions sufficient to form said Mannich Base condensation dispersant product.

Claim 38

A lubricating oil dispersant additive useful in oleaginous compositions which comprises a Mannich Base condensation product obtained by the steps of: (i) providing a N-hydroxyaryl amine-containing Mannich base intermediate obtained by reacting at least one N-hydroxyaryl amine compound, at least one aldehyde reactant and at least one amino-amine or thioamido-amine reactant, said N-hydroxyaryl amine-containing Mannich, base intermediate comprising at least one compound selected from the group consisting of: (a) adducts of the structure, H--(A--A')x.sub.1 --Ar'A'--A--(A'Ar"a"a)x.sub.2 --(A'Ar')x.sub.3 --H wherein x 1 is 0 or 1, x 2 is an integer of 0 to 8, x 3 is 0 or 1, A is a bivalent bis(N-terminated) amino group derived from said amine reactant and contains from 2 to 60 carbon atoms and from 2 to 11 nitrogen atoms, A' comprises the group --CH(T") wherein T" is H or alkyl of from 1 to 9 carbon atoms and is derived from the said aldehyde reactant, and Ar' comprises the moiety; ##STR42## wherein Ar represents ##STR43## and wherein r" is 1 or 2, and derivatives thereof wherein from 1 to 3 ring carbon atoms are each substituted by an alkyl group or halogen atom, wherein T' is H, alkyl of 1 to 3 carbons or halogen, and (b) adducts of the structure: ##STR44## wherein T', A', Ar and A are as defined above, and "a" is an integer of 1 to 2; and said amido-amine and thioamido-amine reactant comprising a reaction product of at least one polyamine and an alpha, beta-unsaturated compound of the formula: ##STR45## wherein X is sulfur or oxygen, Y is --OR 8 , --SR 8 or --NR 8 (R 9 ), wherein R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (ii) contacting said N-hydroxyalkyl amine-containing Mannich base intermediate with (a) at least one polymer substituted mono- or dicarboxylic acid material comprising polymer substituted with C 4 to C 10 monounsaturated dicarboxylic acid producing moieties or C 3 to C 10 monounsaturated monocarboxylic acid moieties, wherein said polymer has a number average molecular weight of from about 300 to 10,000, for a time and under conditions sufficient to form said Mannich Base condensation dispersant product.

Claim 39

The dispersant adduct of claim 35 wherein said polymer comprises polybutylene.

Claim 40

The dispersant adduct of claim 35 wherein said polymer has a number average molecular weight of from about 700 to about 5,000.

Claim 41

The dispersant adduct of claim 37 wherein said polymer comprises polyisobutylene and said number average molecular weight is between about 1,300 and 3,000.

Claim 42

The dispersant adduct of claim 36 wherein said hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material comprises polyisobutylene of about 900 to 4000 number average molecular weight substituted with succinic anhydride moieties, said polyamine comprises polyalkylenepolyamine wherein each said alkylene group contain 2 to 6 carbons and said polyalkylenepolyamine contains 5 to 9 nitrogen atoms per molecule, and said alpha, beta-unsaturated compound comprises at least one member selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.

Claim 43

The dispersant adduct according to claim 39 wherein said amine comprises an amido-amine.

Claim 44

The dispersant adduct according to claim 40 wherein the Ar group is phenyl and T' is H or alkyl of 1 to 3 carbon atoms.

Claim 45

The dispersant adduct according to claim 41 wherein said N-hydroxyaryl amine compound comprises 4-aminophenol.