US2007149414A1PendingUtilityA1
Dispersant viscosity index improvers having high ethylene content and lubricating oil compositions containing the same
Est. expiryDec 28, 2025(expired)· nominal 20-yr term from priority
C10M 2205/024C10N 2030/02C10M 159/005C10M 2205/028C10M 2205/026C10M 2205/022C10N 2030/041C10M 149/00C10N 2040/25C10M 2217/06C10M 2221/04C10N 2060/09C10N 2030/04
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Claims
Abstract
A polymeric composition is disclosed which contains an ethylene-alpha olefin copolymer backbone having at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpla-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms, and an amide group having the formula (I) and/or an imide group having the formula (II): wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more amine compounds described herein.
Claims
exact text as granted — not AI-modified1 . A polymeric composition comprising an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms, and an amide group having the formula (I) and/or an imide group having the formula (II):
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the following amines:
(a) an aromatic amine comprising two aromatic groups, linked by a group, L represented by the following formula:
wherein L is selected from —O—, —N═N—, —NH—, —CH 2 NH—, —C(O)NR 4 —, —C(O)O—, —SO 2 —, —SO 2 NR 5 — or —SO 2 NH—; wherein R 4 and R 5 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about f8 carbon atoms;
wherein each Y 1 , Y 2 , Y 3 , and Y 4 are independently N or CH provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms, or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl an alkenyl or an alkoxyl group having about 1 to about 8 carbon atoms, —OH, —SO 3 H or —SO 3 Na; and
R 10 represents —NH 2 , —NHR 11 , wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —CH 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole;
(c) an aminocarbazole represented by the formula:
wherein R 12 and R 13 independently represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula:
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms,
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(g) an aminomercaptotriazole represented by the formula:
(h) an aminopyrimidine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N-dialkylphenylenediamine and
(m) a benzylamine.
2 . The polymeric composition according to claim 1 , further comprising a polyene selected from non-conjugated dienes and trienes.
3 . The polymeric composition according to claim 1 , wherein the ethylene-alpha copolymer comprises at least 84 mole % ethylene and at most 16 mole % of an about C 3 to about C 28 alpha-monoolefin.
4 . The polymeric composition according to claim 3 , wherein the alpha-monoolefin is an about C 3 to about C 20 alpha-monolefin.
5 . The polymeric composition according to claim 4 , wherein the alpha-monoolefin is an about C 6 to about C 12 alpha-monoolefin.
6 . The polymeric composition according to claim 5 , wherein the alpha-monoolefin is octene.
7 . The polymeric composition according to claim 1 , wherein the amine compound is an aromatic amine selected from the group consisting of
(a) an N-arylphenylenediamine represented by the formula:
wherein R 19 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 20 represents —NH 2 —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 21 represents a hydrogen, an alkyl, an alkenyl, an alkoxyl, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms; and
(b) a phenoxyaniline represented by the formula:
wherein P 22 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl), —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 23 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 24 represents a hydrogen, an alkyl, an alkenyl, an alkoxyl, an aralkyl or an alkaryl group having about: 4 to about 24 carbon atoms.
8 . The polymeric composition according to claim 7 , wherein the N-arylphenylenediamine is N-phenylphenylenediamine.
9 . The polymeric composition according to claim 8 wherein the N-phenylphenylenediamine is N-phenyl-1,4-phenylenediamine.
10 . The polymeric composition according to claim 7 , wherein the phenoxyanilines is 4-phenoxyaniline.
11 . The polymeric compositions according to claim 1 , further comprising an aliphatic amine having a single reactive amino group.
12 . The polymeric composition according to claim 11 , wherein the aliphatic amine having a single reactive amino group has from about 1 to about 8 carbon atoms.
13 . The polymeric composition according to claim 12 , wherein the aliphatic amine having a single reactive amino group is
N,N-dimethylaminopropylamine or aminopropylmorpholine.
14 . An oil-soluble product prepared by the process comprising grafting an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms with an ethylenically unsaturated acylating agent and subsequently reacting the resulting grafted copolymer with one or more of the following amines;
(a) an aromatic amine comprising two aromatic groups, linked by a group, L represented by the following formula:
wherein L is selected from —O—, —N═N—, —NH—, —CH 2 NH—, —C(O)NR 4 —,
—C(O)O—, —SO 2 —, —SO 2 NR 5 — or —SO 2 NH—; wherein R 4 and R 5 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
wherein each Y 1 , Y 2 , Y 3 and Y 4 are independently N or CH, provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms, —OH, —SO 3 H or —SO 3 Na; and
R 10 represents —NH 2 , —NHR 11 , wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —CH 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole;
(c) an aminocarbazole represented by the formula:
wherein R 12 and R 13 independently represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula;
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(g) an aminomercaptotriazole represented by the formula:
(h) an aminopyrimidine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N-dialkylphenylenediamine and
(m) a benzylamine
to yield an oil-soluble product having an amide group with the formula (I) and/or an imide group having the formula (II)
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the amines in (a)-(m) above.
15 . The oil-soluble product prepared by the process according to claim 14 , further comprising a polyene selected from non-conjugated dienes and trienes.
16 . The oil-soluble product prepared by the process according to claim 14 , wherein the ethylene-alpha copolymer comprises at least 84 mole % ethylene and at most 16 mole % of an about C 3 to about C 28 alpha-monoolefin.
17 . The oil-soluble product prepared by the process according to claim 16 , wherein the alpha-monoolefin is an about C 3 to about C 20 alpha-monolefin.
18 . The oil-soluble product prepared by the process according to claim 17 , wherein the alpha-monoolefin is an about C 6 to about C 12 alpha-monoolefin.
19 . The oil-soluble product prepared by the process according to claim 18 , wherein the alpha-monoolefin is octene.
20 . The oil-soluble product prepared by the process according to claim 14 , wherein the ethylenically unsaturated acylating agent is maleic anhydride.
21 . The oil-soluble product prepared by the process according to claim 14 , wherein the amine is an aromatic amine selected from the group consisting of
(a) N-arylphenylenediamine represented by the formula:
wherein R 19 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 20 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10;
and R 21 represents a hydrogen, an alkyl an alkenyl, an alkoxyl, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms; and
(b) a phenoxyaniline represented by the formula:
wherein R 22 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 23 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 24 represents a hydrogen, an alkyl an alkenyl, an alkoxyl, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms.
22 . The oil-soluble product prepared by the process according to claim 21 , wherein the N-arylphenylenediamine is N-phenylphenylenediamine.
23 . The oil-soluble product prepared by the process according to claim 22 , wherein the N-phenylphenylenediamine is N-phenyl-1,4-phenylenediamine.
24 . The oil-soluble product prepared by the process according to claim 21 wherein the phenoxyaniline is 4-phenoxylaniline
25 . The oil-soluble product prepared by the process according to claim 14 , further comprising an aliphatic amine having a single reactive amino group.
26 . The oil-soluble product prepared by the process according to claim 25 , wherein the aliphatic amine having a single reactive amino group has from about 1 to about 8 carbon atoms.
27 . The oil-soluble product prepared by the process according to claim 26 , wherein the aliphatic amine having a single reactive amino group is N,N-dimethylaminopropylamine or aminopropylmorpholine.
28 . A lubricating oil composition comprising a major amount of base oil of lubricating viscosity and a minor amount of a polymeric composition comprising an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms, and an amide group having the formula (I) and/or an imide group having the formula (II):
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the following amines;
(a) an aromatic amine comprising two aromatic groups linked by a group, L represented by the following formula;
wherein L is selected from —O—, —N═N—, —NH—, —OH 2 NH 2 —, —C(O)NR 4 —, —C(O)O—, —SO 2 —, —SO 2 NR 5 — or —SO 2 NH—; wherein R 4 and R 5 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
wherein each Y 1 , Y 2 , Y 3 and, Y 4 are independently N or CH provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms, —OH, —SO 3 or, —SO 3 Na; and
R 10 represents —NH 2 , —NHR , wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —CH 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadazole and aminoalkylthiazole,
(c) an aminocarbazole represented by the formula:
wherein R 12 and R 13 independently represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula:
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms:
(g) an aminomercaptotriazole: represented by the formula:
(h) an aminopyrimidine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N.-dialkylphenylenediamine and
(m) a benzylamine.
29 . The lubricating oil composition according to claim 28 , further comprising a polyene selected from non-conjugated dienes and trienes.
30 . The lubricating oil composition according to claim 28 , wherein the ethylene-alpha copolymer comprises at least 84 mole % ethylene and at least 16 mole % of an about C 3 to about C 28 alpha-monoolefin.
31 . The lubricating oil composition according to claim 30 , wherein the alpha-monoolefin is a about C 6 to about C 20 alpha-monoolefin.
32 . The lubricating oil composition according to claim 31 , wherein the alpha-monoolefin is a about C 6 to: about C 12 alpha-monoolefin.
33 . The lubricating oil composition according to claim 32 , wherein the z:o alpha-monoolefin is octene.
34 . The lubricating oil composition according to claim 28 , wherein the amine is an aromatic amine selected from the group consisting of
(a) an N-arylphenylenediamine represented by the formula:
wherein R 19 represents a hydrogen, —NH-aryl, —NH-alkyl;, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 20 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 21 represents a hydrogen, an alkyl an alkenyl, an alkoxy, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms; and
(b) a phenoxyaniline represented by the formula:
wherein R 22 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 23 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 24 represents a hydrogen, an alkyl, an alkenyl, an alkoxyl, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms.
35 . The lubricating oil composition according to claim 34 , wherein the N-aryl phenylenediamine is N-phenylphenylenediamine
36 . The lubricating oil composition according to claim 35 , wherein the N-phenylphenylenediamine is N-phenyl-1,4-phenylenediamine.
37 . The lubricating oil composition according to claim 34 , wherein the phenoxyaniline is 4-phenoxylaniline.
38 . The lubricating oil composition according to claim 28 , further comprising an amine having a single reactive amine group.
39 . The lubricating oil composition according to claim 38 , wherein the aliphatic amine having a single reactive amino group has from about 1 to about 8 carbon atoms.
40 . The lubricating oil compositions according to claim 39 , wherein the aliphatic amine having a single reactive amino group is N,N-dimethylaminopropylamine or aminopropylmorpholine.
41 . The lubricating oil composition according to claim 28 , wherein the polymetric composition is from about 2 wt % to about 30 wt %, based on the total weight of the lubricating oil composition.
42 . The lubricating oil composition according to claim 41 , wherein the polymeric composition is from about 4 wt % to about 20 wt %, based on the total weight of the lubricating oil composition.
43 . The lubricating oil composition according to claim 42 , wherein the polymeric composition is from about 6 wt % to about 12 wt %, based on the total weight of the lubricating oil composition.
44 . A lubricating oil composition comprising a major amount of base oil of lubricating viscosity and a minor amount of an oil-soluble product prepared by the process comprising grafting an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2: per 1000 carbon atoms with an ethylenically unsaturated acylating agent and subsequently reacting the resulting grafted copolymer with one or more of the following amines:
(a) an aromatic amine comprising two aromatic groups linked by a group, L, represented by the following formula;
wherein L is selected from —O—, —N═N—, —NH—, —CH 2 NH—, —C(O)NR 4 —, —C(O)O—, —SO 2 —, —SO 2 NR 5 — or —SO 2 NH—; wherein R 4 and R 5 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
wherein each Y 1 , Y 2 Y 3 and Y 4 are independently N or CH provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms, —OH, —SO 3 H or —SO 3 Na; and
R 10 represents —NH 2 , —NHR 11 , wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —C 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole;
(c) an aminocarbazole represented by the formula:
wherein R 12 and R 13 independently represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula:
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(g) an aminomercaptotriazole represented by the formula:
(h) an aminopyrimidine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N-dialkylphenylenediamine and
(m) a benzylamine
to yield an oil-soluble product having an amide group with the formula (l) and/or an imide group having the formula (II):
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the amines in (a)-(m) above.
45 . The lubricating oil composition according to claim 44 , further comprising a polyene selected from non-conjugated dienes and trienes.
46 . The lubricating oil composition according to claim 44 , wherein the ethylene-alpha copolymer comprises at least 83 mole % ethylene and at least 17 mole % of an about C 3 to about C 28 alpha-monoolefin.
47 . The lubricating oil composition according to claim 46 , wherein the ethylene-alpha copolymer comprises at least 84 mole % ethylene and at least 16 mole % of an about C 3 to about C 28 alpha-monoolefin.
48 . The lubricating oil composition according to claim 47 , wherein the alpha-monoolefin is an about C 3 to about C 20 alpha-monoolefin.
49 . The lubricating oil composition according to claim 48 , wherein the alpha-monoolefin is an about C 6 to about C 12 alpha-monoolefin.
50 . The lubricating oil composition according to claim 49 , wherein the alpha-monoolefin is octene.
51 . The lubricating oil composition according to claim 44 , wherein the ethylenically unsaturated acylating agent is maleic anhydride.
52 . The lubricating oil composition according to claim 44 , wherein the amine is an aromatic amine selected from the group consisting of:
(a) N-arylphenylenediamine represented by the formula:
wherein R 19 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 20 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 21 represents a hydrogen, an alkyl, an alkenyl, an alkoxyl, an aralky or an alkaryl group having about 4 to about 24 carbon atoms; and
(b) a phenoxyaniline represented by the formula:
wherein R 22 represents a hydrogen, —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 23 represents —NH 2 , —CH 2 —(CH 2 ) n —NH 2 , —CH 2 -aryl-NH 2 and n is from about 1 to about 10; and
R 24 represents a hydrogen, an alkyl, an alkenyl an alkoxyl, an aralkyl or an alkaryl group having about 4 to about 24 carbon atoms.
53 . The lubricating oil composition according to claim 52 , wherein the N-arylphenylenediamine is N-phenylphenylenediamine.
54 . The lubricating oil composition according to claim 53 , wherein the N-phenylphenylenediamine is N-phenyl-1,4-phenylenediamine.
55 . The lubricating oil composition according to claim 52 , wherein the phenoxyaniline is 4-phenoxylaniline,
56 . The lubricating oil composition according to claim 44 , further comprising an aliphatic amine having a single reactive amino group.
57 . The lubricating oil composition according to claim 56 , wherein the aliphatic amine having a single reactive amino group has from about 1 to about 8 carbon atoms.
58 . The lubricating oil composition according to claim 57 , wherein the aliphatic amine having a single reactive amino group is N,N-dimethylaminiopropylamine or aminopropylmorpholine.
59 . The lubricating oil composition according to claim 44 , wherein the oil-soluble product prepared by the process is from about 2 wt % to about 30 wt %, based on the total weight of the lubricating oil composition.
60 . The lubricating oil composition according to claim 59 wherein the oil-soluble product prepared by the process is from about 4 wt % to about 20 wt %, based on the total weight of the lubricating oil composition.
61 . The lubricating oil composition according to claim 60 , wherein the oil-soluble product prepared by the process is from about 6 wt % to about 12 wt %, based on the total weight of the lubricating oil composition.
62 . A method of improving the soot and/or sludge dispersancy in an internal combustion engine, said method comprising operating said internal combustion engine with a lubricating oil composition comprising a major amount of base oil of lubricating viscosity and a minor amount of a polymeric composition comprising an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene and at most 18 mole % of an about C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms, and an amide group having the formula (I) and/or an imide group having the formula (II):
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine, provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the following amines:
(a) an aromatic amine comprising two aromatic groups, linked by a group L represented by the following formula,
wherein L is selected from the group consisting of —O—, —N═N—, —NH—, —CH 2 NH—, —C(O)NR 4 —, —C(O)O—, —SO 2 —, —SO 2 NR 3 — or —SO 2 NH—; wherein R 4 and R 5 independently re-present a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
wherein each Y 1 Y 2 Y 3 and Y 4 are independently N or CH provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms, —OH, —SO 3 H or —SO 3 Na; and
R 10 represents —NH 2 , —NHR 11 wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —CH 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole;
(c) an aminocarbazole represented by the formula:
wherein R 12 and R 13 represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula:
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(g) an aminomercaptotriazole represented by the formula:
(h) an aminopyridine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N-dialkylphenylenediamine and
(m) a benzylamine
63 . A method of improving the soot and/or sludge dispersancy in an internal combustion engine, said method comprising operating said internal combustion engine with a lubricating oil composition comprising a major amount of base oil of lubricating viscosity and a minor amount of an oil-soluble product produced by the process comprising grafting an ethylene-alpha olefin copolymer backbone comprising at least 82 mole % ethylene annd at most 138 mole % of an about: C 3 to about C 28 alpha-monoolefin, wherein the alpha-monoolefin has a monomer distribution resulting from a R a R b product measured by 13 C-NMR below 0.8 and a level of regio-inversions less than 2 per 1000 carbon atoms with an ethylenically unsaturated acylating agent and subsequently reacting the resulting grafted copolymer with one or more of the following amines:
(a) an aromatic amine comprising two aromatic groups, linked by a group L represented by the following formulas:
wherein L is selected from the group consisting of —O—, —N═N—, —NH—, —CH 2 NH—, —C(O)NR 4 , —C(O)O—, —SO 2 —, —SO 2 NR 5 — or —SO 2 NH—; wherein R 4 and R 5 independently represent a hydrogen, an alkyl an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms;
wherein each Y 1 Y 2 Y 3 and Y 4 are independently N or CH provided that Y 1 and Y 2 may not both be N;
R 6 and R 7 independently represent a hydrogen, —OH, —NO 2 , —SO 3 H, —SO 3 Na, —CO 2 H or salt thereof —NH-aryl, —NH-alkyl, —NH-alkaryl, —NH-aralkyl having up to about 24 carbon atoms or a branched or straight chain group having from about 4 to about 24 carbon atoms that can be alkyl, alkenyl, alkoxyl, aralkyl, alkaryl, hydroxyalkyl or aminoalkyl;
R 8 and R 9 independently represent a hydrogen, an alkyl, an alkenyl or an alkoxyl group having from about 1 to about 8 carbon atoms, —OH, —SO 3 H or —SO 3 Na; and
R 10 represents —NH 2 , —NHR 11 , wherein R 11 is an alkyl or an alkenyl group having from about 1 to about 8 carbon atoms, —CH 2 —(CH 2 ) n —NH 2 or —CH 2 -aryl-NH 2 and n is from 0 to about 10;
(b) an aminothiazole selected from the group consisting of aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole;
(c) an aminocarbazole represented by the formula,
wherein R 12 and R 13 represent a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(d) an aminoindole represented by the formula:
wherein R 14 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(e) an aminopyrrole represented by the formula:
wherein R 15 represents a divalent alkylene group having about 2 to about 6 carbon atoms and R 16 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(f) an amino-indazolinone represented by the formula:
wherein R 17 represents a hydrogen, an alkyl or an alkenyl group having from about 1 to about 14 carbon atoms;
(g) an aminomercaptotriazole represented by the formula:
(h) an aminopyrimidine represented by the formula:
wherein R 18 represents a hydrogen, an alkyl, an alkenyl, or an alkoxyl group having from about 1 to about 8 carbon atoms;
(i) a ring substituted or unsubstituted aniline;
(j) an aminoquinoline;
(k) an aminobenzimidazole;
(l) a N,N-dialkylphenylenediamine and
(m) a benzylamine
to yield an oil-soluble product having an amide group with the formula (I) and/or an imide group having the formula (II);
wherein P is the ethylene-alpha olefin copolymer backbone, R 1 is hydrogen or —CO—X′, R 2 and R 3 are independently hydrogen or —CH 3 , X and X′ are independently —OH, alkoxyl of 1 to about 24 carbon atoms, or a secondary or tertiary amine provided that at least one of X and X′ is a secondary or tertiary amine, and Z is a tertiary amine, wherein Z and X and X′, when X and X′ are secondary or tertiary amines, are each independently derived from one or more of the amines in (a)-(m) above.Join the waitlist — get patent alerts
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