Mannich condensation products useful as sequestering agents

A Mannich condensation product prepared by the Mannich condensation of:

• (a) a polyisobutyl-substituted hydroxyaromatic compound having the formula
• wherein R1 is polyisobutyl derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000, R2 is hydrogen or lower alky having one carbon atom to about 10 carbon atoms, and R3 is hydrogen or —OH;
• (b) a formaldehyde or an aldehyde having the formula
• wherein R′ is branched or linear alkyl having one carbon atom to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms;
• (c) an amino acid or ester derivative thereof having the formula
• wherein W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4, A is hydrogen or alkyl having one carbon atom to about 6 carbon atoms;
• and
• (d) an alkali metal base.

A Mannich condensation product having the formula

• wherein each R is independently —CHR′—, wherein R′ is branched or linear alkyl having one to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms, R1 is a polyisobutyl group derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000;
• X is hydrogen, an alkali metal ion, or alkyl having one carbon atom to about 6 carbon atoms;
• W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4;
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be:
• wherein R, R1, Y′, X, and W are as defined above.

A method for preventing metal ion catalyzed oxidation and polymerization reactions in a hydrocarbon medium comprising sequestering the metal ion by the addition of an effective amount of a compound having the formula

• wherein each R is independently —CHR′—, wherein R′ is branched or linear alkyl having one to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms R1 is a polyisobutyl group derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000;
• X is hydrogen, an alkali metal ion, or alkyl having one carbon atom to about 6 carbon atoms;
• W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4;
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be
• wherein R, R1, Y′, X, and W are as defined above.

A process for preparing a Mannich condensation product comprising:

• mixing under reaction conditions,
• (a) a polyisobutyl-substituted hydroxyaromatic compound having the formula
• wherein R1 is polyisobutyl derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and a number average molecular weight in the range of about 400 to about 5,000, R2 is hydrogen or lower alky having one carbon atom to about 10 carbon atoms, and R3 is hydrogen or —OH;
• (b) a formaldehyde or an aldehyde having the formula
• or polymers thereof, wherein R′ is branched or linear alkyl having one carbon atom to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms;
• (c) an amino acid or ester derivative thereof having the formula
• wherein W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4, A is hydrogen or alkyl having one carbon atom to about 6 carbon atoms;
• (d) in the presence of an alkali metal base to obtain the Mannich condensation product.

A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor effective amount of one or more Mannich condensation products having the formula

• wherein each R is independently —CHR′—, wherein R′ is branched or linear alkyl having one to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms, R1 is a polyisobutyl group derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000;
• X is hydrogen, an alkali metal ion, or alkyl having one carbon atom to about 6 carbon atoms;
• W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4;
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be
• wherein R, R1, Y′, X, and W are as defined above.

A lubricating oil concentrate comprising from about 90 weight percent to about 10 weight percent of an oil of lubricating viscosity and from about 10 weight percent to about 90 weight percent of one or more lubricating Mannich condensation products having the formula

• wherein each R is independently —CHR′—, wherein R′ is branched or linear alkyl having one to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms, and R1 is a polyisobutyl group containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000;
• X is hydrogen, an alkali metal ion, or alkyl having one to about 6 carbon atoms;
• W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4;
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be
• wherein R, R1, Y′, X, and W are as defined above.

A fuel composition comprising a major amount of hydrocarbons boiling in the gasoline or diesel range and a minor effective amount of one or more Mannich condensation products having the formula

• wherein each R is independently —CHR′—, wherein R′ is branched or linear alkyl having one to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms, and R1 is a polyisobutyl group containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000;
• X is hydrogen, an alkali metal ion or alkyl having one to about 6 carbon atoms;
• W is —[CHR″]—m wherein each R″ is independently H, alkyl having one carbon atom to about 15 carbon atoms, or a substituted-alkyl having one carbon atom to about 10 carbon atoms and one or more substituents selected from the group consisting of amino, amido, benzyl, carboxyl, hydroxyl, hydroxyphenyl, imidazolyl, imino, phenyl, sulfide, or thiol;
• and m is an integer from one to 4;
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be
• wherein R, R1, Y′, X, and W are as defined above.

A fuel concentrate comprising an inert stable oleophilic organic solvent boiling in the range of from about 65° C. to about 204° C. and from about 10 weight percent to about 90 weight percent of one or more Mannich condensation products having the formula

• wherein R is either CH2 or CHR′ and wherein R′ is branched or linear alkyl having one carbon atom to about 10 carbon atoms, cycloalkyl having from about 3 carbon atoms to about 10 carbon atoms, aryl having from about 6 carbon atoms to about 10 carbon atoms, alkaryl having from about 7 carbon atoms to about 20 carbon atoms, or aralkyl having from about 7 carbon atoms to about 20 carbon atoms, and R1 is polyisobutyl derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 400 to about 5,000, X is hydrogen, an alkali metal ion or alkyl having one carbon atom to about 6 carbon atoms,
• Y is hydrogen, alkyl having one carbon atom to about 10 carbon atoms, —CHR′OH, wherein R′ is as defined above,
• or
• wherein Y′ is —CHR′OH, wherein R′ is as defined above;
• and R, X, and W are as defined above;
• Z is hydroxyl, a hydroxyphenyl group of the formula
• wherein R, R1, Y′, X, and W are as defined above,
• and n is an integer from 0 to 20, with the proviso that when n=0, Z must be
• wherein R, R1, Y′, X, and W are as defined above.