US 7,253,231 B2 · Grafted multi-functional olefin copolymer VI modifiers and uses thereof

A method of lubricating an internal combustion engine wherein said method comprises adding to a crankcase of said engine

a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising reacting an acylating agent with an olefin copolymer having a number average molecular weight greater than about 1,000 in the presence of a free radical initiator and said method being essentially free of hydrocarbon solvent in an extruder to provide a copolymer intermediate comprising an acylated olefin copolymer having a degree of grafting (DOG) of the acylating agent on the olefin copolymer of at least 0.5 wt. %, and wherein the copolymer intermediate is reduced in molecular weight;
vacuum stripping unreacted components;
pelletizing the copolymer intermediate to form a pelletized copolymer intermediate;
dissolving the pelletized copolymer intermediate in a neutral oil to form a dissolved copolymer intermediate;
and reacting the dissolved copolymer intermediate with an amine to provide a grafted olefin copolymer additive reaction product, wherein the lubricating oil composition achieves a weighted demerits-1P (WDP) value of less than 250, a top land carbon (TLC) value of less than 20, and a top groove carbon (TGC) value of less than 20, in the Caterpillar 1P Test Method.

2 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n—)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the lubricating oil composition achieves a weighted demerits-1P (WDP) value of less than 250, a top land carbon (TLC) value of less than 20, and a top groove carbon (TGC) value of less than 20, in the Caterpillar 1P Test Method.

11 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n-)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the lubricating oil composition forms a boundary film having a percent film resistance value of about 80 to about 95 measured in a High Frequency Reciprocating Rig (HFRR) test conducted at a 3% soot level, wherein the percent resistance is determined from an oil resistivity value measured according to ASTM D 1169.

11 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n-)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the lubricating oil composition forms a boundary film having a percent film resistance value of about 50 to about 70 as measured in a High Frequency Reciprocating Rig (HFRR) test conducted at a 6% soot level, wherein the percent resistance is determined from an oil resistivity value measured according to ASTM D 1169.

11 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n-)m—NH2, —(CH2)n—NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the lubricating oil composition has a kinematic viscosity at 100° C. (KV100) in the range of 9.3 to 21.8 cSt.

11 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n-)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the lubricating oil composition achieves a viscosity increase of less than 10 cSt at 100° C. at a soot level of up to 6.0% in the Mack T-11 test.

11 more elements

A method of lubricating a transmission of an automotive vehicle having a transmission wherein said method comprises lubricating said transmission of said vehicle with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of an additive reaction product prepared by a method comprising

(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n—)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms, wherein the internal combustion engine comprises a cooled exhaust gas recirculation (EGR) equipped heavy duty diesel engine.

11 more elements

A lubricated engine comprising a cooled exhaust gas recirculation system, whereby exhaust gases comprising soot generated in the combustion in the engine of fuel contact a lubricating oil used to lubricate said engine, wherein said lubricating oil comprises:

a base oil, and at least one dispersant viscosity index improver prepared by a method comprising
(A) reacting an olefin copolymer prepared from ethylene and at least one C3 to C10 alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes comprising from about 15 to 80 mole percent of ethylene, from about 20 to 85 mole percent of said C3 to C10 alpha-monoolefin, and from about 0 to 15 mole percent of said polyene, said copolymer having a number average molecular weight ranging from 1,000 to 500,000, with an olefinic carboxylic acid acylating agent, said process comprising heating said copolymer to a molten condition at a temperature in the range of 60° C. to 240° C., grafting in an extruder or a mixing device, said olefinic carboxylic acylating agent onto said copolymer, optionally subsequently reducing the molecular weight of said copolymer, thereby producing a grafted, acylated olefin copolymer and having at least 1.0 molecules of said carboxylic acid acylating agent grafted onto each molecule of said olefin copolymer, and
(B) reacting said grafted, acylated olefin copolymer in (A) with an amine compound selected from the group consisting of:
(a) an N-arylphenylenediamine represented by the formula:
in which Ar is aromatic and R1 is —H, —NH2, —(—NH-Aryl)n—H, —(—NH-Alkyl)n—H, —NH-arylalkyl, a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl, R2 is (—NH2, —(NH(CH2)n-)m—NH2, —(CH2)n—NH2, -aryl-NH2, in which n and m each has a value from 1 to 10, and R3 is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, alkaryl having from 4 to 24 carbon atoms,
(b) an aminocarbazole represented by the formula:
in which R and R1 represent hydrogen or an alkyl, alkenyl, or alkoxyl radical having from 1 to 14 carbon atoms,
(c) an aminoindole represented by the formula:
in which R represents hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(d) an amino-indazolinone represented by the formula:
in which R is hydrogen or an alkyl radical having from 1 to 14 carbon atoms,
(e) an aminomercaptotriazole represented by the formula:
in which R can be absent or can be C1-C10 linear or branched hydrocarbon selected from the group consisting of alkyl, aryl, alkaryl, or arylalkyl,
(f) an aminopyrimidine represented by the formula:
in which R represents hydrogen or an alkyl or alkoxyl radical having from 1 to 14 carbon atoms in an amount sufficient to reduce the amount of oil thickening of the lubricating oil as compared to use of the lubricating oil without the additive reaction product.

12 more elements

Grafted multi-functional olefin copolymer VI modifiers and uses thereof

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Grafted multi-functional olefin copolymer VI modifiers and uses thereof

Life of this patent

Abstract

Claims16