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Hydrogenated lithiated copolymers grafted with organic nitrogen compounds as viscosity index improvers having dispersant properties

Assignee: Phillips Petroleum Co
•
Filing: 1977-08-22
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Granted: 1979-03-20
•
Expires: 1997-08-22
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Abstract

Abstract Nitrogen-containing copolymers are prepared by the reaction of lithiated hydrogenated conjugated diene-monovinylarene copolymers with nitrogen-containing organic compounds. The nitrogen-containing copolymers are oil additives which combine the aspects of viscosity index improvers with dispersant properties.

Inventors

  • 👤 William J. Trepka

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 09:04
CPC Classifications
C; C10; C10M; C10M143/00; C10M143/12; C08; C08C; C08C19/00; C08C19/26; C08C19/30; C08C19/42; C08F; C08F8/00; C08F8/30; C08F8/32; C10M2205/00; C10M2205/22; C10M2207/00; C10M2207/28; C10M2207/287; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/044; C10M2215/06; C10M2215/066; C10M2215/14; C10M2215/16; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/046; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/02; C10N2040/08

Claims Analysis

Total Claims: 54
Claim 1
Independent Claim 263 words
Shear-stable, mineral oil-based compositions comprising a major amount of a mineral base oil, and a minor effective viscosity improving amount of an oil-soluble organonitrogen compound grafted hydrogenated conjugated diene/monovinylarene copolymer dissolved therein, said copolymer having a polymerized monovinylarene content of about 20 to 70 weight percent with the proviso that when said copolymer contains a random block, the block polymonovinylarene content is in the range of about 15 to 35 weight percent, a number average molecular weight suitable for oil solubility, the extent of hydrogenation of said copolymer such that about at least 95 weight percent of olefinic double bonds having been saturated and less than about 5 weight percent of aromatic double bonds having been saturated, said copolymer characterized as having been prepared by the process which comprises metalating a hydrogenated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, and reacting the resulting metalated hydrogenated copolymer with effective amounts of at least one nitrogen-containing organic compound represented by the general formulae X--Q--(NR 2 3 ) n or Y Q--(NR 2 3 ) n ! m wherein each R 3 is the same or different alkyl, cycloalkyl, aryl, or combination radical, Q is a hydrocarbon radical having a valence of n+1 and is a saturated aliphatic, saturated cycloaliphatic, aromatic or combination radical, X is a functional group capable of reaction on a one-to-one basis with one equivalent of polymer metal, Y is or contains a functional group capable of reacting on a one-to-one basis with one equivalent of polymer metal, n is at least one, and m is 2 or 3, thereby preparing said grafted copolymer.
Claim 2
Dependent Claim 263 words
Shear-stable, mineral oil-based compositions comprising a major amount of a mineral base oil, and a minor effective viscosity improving amount of an oil-soluble organonitrogen compound grafted hydrogenated conjugated diene/monovinylarene copolymer dissolved therein, said copolymer having a polymerized monovinylarene content of about 20 to 70 weight percent with the proviso that when said copolymer contains a random block, the block polymonovinylarene content is in the range of about 15 to 35 weight percent, a number average molecular weight suitable for oil solubility, the extent of hydrogenation of said copolymer such that about at least 95 weight percent of olefinic double bonds having been saturated and less than about 5 weight percent of aromatic double bonds having been saturated, said copolymer characterized as having been prepared by the process which comprises metalating a hydrogenated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, and reacting the resulting metalated hydrogenated copolymer with effective amounts of at least one nitrogen-containing organic compound represented by the general formulae X--Q--(NR 2 3 ) n or Y Q--(NR 2 3 ) n ! m wherein each R 3 is the same or different alkyl, cycloalkyl, aryl, or combination radical, Q is a hydrocarbon radical having a valence of n+1 and is a saturated aliphatic, saturated cycloaliphatic, aromatic or combination radical, X is a functional group capable of reaction on a one-to-one basis with one equivalent of polymer metal, Y is or contains a functional group capable of reacting on a one-to-one basis with one equivalent of polymer metal, n is at least one, and m is 2 or 3, thereby preparing said grafted copolymer.
Claim 3
Dependent Claim 43 words
The composition of claim 1 wherein X is selected from ##STR4## N.tbd.C--; R 3 N═HC--; and ##STR5## wherein each R 4 is the same or different and is hydrogen, alkyl, cycloalkyl, aryl, or combination radical, and Y is or contains an X group.
Claim 4
Dependent Claim 49 words
A composition according to claim 1 wherein the nitrogen-containing grafted copolymer has a number average molecular weight in the range of about 20,000 to 300,000, a vinyl content prior to hydrogenation of about 20 to 95 weight percent, and a nitrogen content of about 0.01 to 5 weight percent.
Claim 5
Dependent Claim 38 words
A composition according to claim 3 wherein said grafted copolymer has a number average molecular weight in the range of about 25,000 to 100,000, and a vinyl content prior to hydrogenation of about 20 to 70 weight percent.
Claim 6
Dependent Claim 51 words
A composition according to claim 4 wherein the mineral oil is a lubricating oil and has a viscosity at 210° F. in the range of about 30 to 250 SUS, and said organonitrogen compound grafted hydrogenated copolymer exhibits a nitrogen content in the range of about 0.05 to 0.5 weight percent.
Claim 7
Dependent Claim 33 words
A composition according to claim 5 wherein said grafted copolymer is employed in an amount in the range of about 0.5 to 10 volume percent relative to the total oil excluding other additives.
Claim 8
Dependent Claim 18 words
A composition according to claim 6 wherein said nitrogen-containing compound is selected from the group consisting of ##STR6##
Claim 9
Dependent Claim 26 words
A composition according to claim 7 wherein said copolymer is a copolymer of butadiene and styrene, isoprene and styrene, butadiene and α-methylstyrene, or isoprene and α-methylstyrene.
Claim 10
Dependent Claim 35 words
The composition according to claim 8 wherein said hydrogenated copolymer is a 41/59 weight percent hydrogenated butadiene/styrene block copolymer having a block styrene content of about 20 weight percent, and said nitrogen-containing compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 11
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 12
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is p-dimethylaminobenzaldehyde.
Claim 13
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is 3-dimethylaminoproprionitrile.
Claim 14
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is 4-diethylamino-2-butanone.
Claim 15
Dependent Claim 27 words
The composition according to claim 8 wherein said nitrogen-containing compound is N.tbd.C--CH 2 CH 2 --CH (CH 2 ) 2 --N(CH 3 ) 2 ! 2 .
Claim 16
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR7##
Claim 17
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR8##
Claim 18
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR9##
Claim 19
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR10##
Claim 20
Dependent Claim 28 words
The composition according to claim 8 wherein said nitrogen-containing compound is CH 3 N═CH--CH 2 --C(CH 3 ) 2 --CH 2 --N(C 4 H 9 ) 2 .
Claim 21
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR11##
Claim 22
Dependent Claim 12 words
The composition according to claim 8 wherein said nitrogen-containing compound is ##STR12##
Claim 23
Dependent Claim 48 words
The composition of claim 1 wherein said copolymer is selected from copolymers represented by B/A, B/A--A, A-B, and mixtures, wherein B/A represents a randomized block of conjugated diene/monovinylarene, which can be tapered, A represents homopolymeric block of polymerized monovinylarene, and B represents a block of homopolymerized polyconjugated diene.
Claim 24
Dependent Claim 30 words
The composition of claim 1 wherein said copolymer contains a random block B/A, and wherein the block polystyrene content is in the range of about 15 to 25 weight percent.
Claim 25
Dependent Claim 41 words
The composition of claim 1 wherein said base oil is a lubricating oil having a minimum VI of about 130, wherein said grafted copolymer is employed in an amount of about 0.5 to 5 volume percent relative to the base oil.
Claim 26
Dependent Claim 30 words
The composition of claim 1 wherein said base oil is an automotive transmission fluid wherein said grafted copolymer is employed in an amount of about 3 to 5 volume percent.
Claim 27
Dependent Claim 29 words
The composition of claim 1 wherein said base oil is an aviation oil wherein said grafted copolymer is employed in an amount of about 8 to 9 volume percent.
Claim 28
Dependent Claim 250 words
Nitrogen-containing grafted hydrogenated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymers having polymerized monovinylarene content of about 20 to 70 weight percent with the proviso that when said copolymer contains a random conjugated diene/monovinylarene block, the block polymonovinylarene content is in the range of about 15 to 35 weight percent, a number average molecular weight of at least about 20,000, the extent of hydrogenation of said copolymer such that about at least 95 weight percent of olefinic double bonds having been saturated, and less than about 5 weight percent of aromatic double bonds having been saturated, said copolymer characterized as having been prepared by the process which comprises metalating a hydrogenated conjugated diene/monovinylarene copolymer, and reacting the resulting metalated hydrogenated copolymer with an effective amount of a nitrogen-containing organic compound represented by the general formulae X--Q--(NR 2 3 ) n or Y Q--(NR 2 3 ) n ! m wherein each R 3 is the same or different alkyl, cycloalkyl, aryl, or combination radical thereof; Q is a hydrocarbon radical having a valence of n+1 and is a saturated aliphatic, saturated cycloaliphatic, aromatic, or combination radical; X is a functional group capable of reaction on a one-to-one basis with one equivalent of polymer lithium; and Y is or contains a functional group capable of reacting on a one-to-one basis with one equivalent of polymer lithium; n is at least one, and m is 2 or 3, such that the resulting grafted copolymer exhibits a nitrogen content of at least about 0.01 weight percent.
Claim 29
Dependent Claim 250 words
Nitrogen-containing grafted hydrogenated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymers having polymerized monovinylarene content of about 20 to 70 weight percent with the proviso that when said copolymer contains a random conjugated diene/monovinylarene block, the block polymonovinylarene content is in the range of about 15 to 35 weight percent, a number average molecular weight of at least about 20,000, the extent of hydrogenation of said copolymer such that about at least 95 weight percent of olefinic double bonds having been saturated, and less than about 5 weight percent of aromatic double bonds having been saturated, said copolymer characterized as having been prepared by the process which comprises metalating a hydrogenated conjugated diene/monovinylarene copolymer, and reacting the resulting metalated hydrogenated copolymer with an effective amount of a nitrogen-containing organic compound represented by the general formulae X--Q--(NR 2 3 ) n or Y Q--(NR 2 3 ) n ! m wherein each R 3 is the same or different alkyl, cycloalkyl, aryl, or combination radical thereof; Q is a hydrocarbon radical having a valence of n+1 and is a saturated aliphatic, saturated cycloaliphatic, aromatic, or combination radical; X is a functional group capable of reaction on a one-to-one basis with one equivalent of polymer lithium; and Y is or contains a functional group capable of reacting on a one-to-one basis with one equivalent of polymer lithium; n is at least one, and m is 2 or 3, such that the resulting grafted copolymer exhibits a nitrogen content of at least about 0.01 weight percent.
Claim 30
Dependent Claim 44 words
The nitrogen-containing grafted copolymers of claim 27 wherein X is ##STR13## N.tbd.C--; R 3 N═HC--; ##STR14## wherein each R 4 is the same or different and is hydrogen, alkyl, cycloalkyl, aryl, or combination radical; and Y is X or contains an X functional group.
Claim 31
Dependent Claim 22 words
The nitrogen-containing grafted copolymers of claim 27 wherein the nitrogen content is in the range of about 0.01 to 5 weight percent.
Claim 32
Dependent Claim 49 words
A copolymer according to claim 27 wherein the nitrogen-containing grafted copolymer has a number average molecular weight in the range of about 20,000 to 300,000, a vinyl content prior to hydrogenation of about 20 to 95 weight percent, and a nitrogen content of about 0.01 to 5 weight percent.
Claim 33
Dependent Claim 38 words
A copolymer according to claim 30 wherein said grafted copolymer has a number average molecular weight in the range of about 25,000 to 100,000, and a vinyl content prior to hydrogenation of about 20 to 70 weight percent.
Claim 34
Dependent Claim 18 words
A copolymer according to claim 27 wherein said nitrogen-containing compound is selected from the group consisting of ##STR15##
Claim 35
Dependent Claim 26 words
A copolymer according to claim 32 wherein said copolymer is a copolymer of butadiene and styrene, isoprene and styrene, butadiene and α-methylstyrene, or isoprene and α-methylstyrene.
Claim 36
Dependent Claim 37 words
The copolymer according to claim 33 wherein said hydrogenated butadiene-styrene block copolymer is a 41/59 weight percent hydrogenated butadiene/styrene block copolymer having a block styrene content of about 20 weight percent, and said nitrogen-containing compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 37
Dependent Claim 12 words
The copolymer according to claim 34 wherein said nitrogen-containing compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 38
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is p-dimethylaminobenzaldehyde.
Claim 39
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is 3-dimethylaminoproprionitrile.
Claim 40
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is 4-diethylamino-2-butanone.
Claim 41
Dependent Claim 27 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is N.tbd.C--CH 2 CH 2 --CH (CH 2 ) 2 --N(CH 3 ) 2 ! 2 .
Claim 42
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR16##
Claim 43
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR17##
Claim 44
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR18##
Claim 45
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR19##
Claim 46
Dependent Claim 28 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is CH 3 N═CH--CH 2 --C(CH 3 ) 2 --CH 2 --N(C 4 H 9 ) 2 .
Claim 47
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR20##
Claim 48
Dependent Claim 12 words
The copolymer according to claim 33 wherein said nitrogen-containing compound is ##STR21##
Claim 49
Dependent Claim 48 words
The copolymer of claim 27 wherein said copolymer is selected from copolymers represented by B/A, B/A--A, A-B, and mixtures, wherein B/A represents a randomized block of conjugated diene/monovinylarene, which can be tapered, A represents homopolymeric block of polymerized monovinylarene, and B represents a block of homopolymerized polyconjugated diene.
Claim 50
Dependent Claim 30 words
The copolymer of claim 47 wherein said copolymer contains a random block B/A, and wherein the block polystyrene content is in the range of about 15 to 25 weight percent.
Claim 51
Dependent Claim 30 words
The compositions according to claim 1 wherein said X-Q-(NR 2 3 ) n or Y Q-(NR 2 3 ) n ! m is said X-Q-(NR 2 3 ) n .
Claim 52
Dependent Claim 16 words
The compositions according to claim 1 wherein said grafted copolymer is subjected to a recovery step.
Claim 53
Dependent Claim 30 words
The copolymers according to claim 27 wherein said X-Q-(NR 2 3 ) n or Y Q-(NR 2 3 ) n ! m is said X-Q-(NR 2 3 ) n .
Claim 54
Dependent Claim 12 words
The copolymers according to claim 27 further employing a copolymer recovery step.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-03-19 1982-09-18 1983-03-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-03-19 1986-09-18 1987-03-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-03-19 1990-09-18 1991-03-20 $7700.00 Window Closed / Lapsed

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