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US4238202A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydrocarbon fuels with carburetor detergent properties

Assignee: Phillips Petroleum Co
•
Filing: 1979-08-31
•
Granted: 1980-12-09
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Expires: 1999-08-31
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Abstract

Abstract Carburetor detergency properties of hydrocarbon fuels are provided by nitrogen-containing organic compound-grafted, hydrogenated conjugated diene-monovinylarene copolymers.

Inventors

  • 👤 William J. Trepka
  • 👤 Richard J. Sonnenfeld

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 18:11
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/234

Claims Analysis

Total Claims: 48
Claim 1
Independent Claim 274 words
Hydrocarbon fuel compositions exhibiting carburetor detergency properties comprising a major amount of a liquid hydrocarbon fuel and a minor effective amount of gasoline-soluble nitrogen-containing organic 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 less than about 35 weight percent, a number average molecular weight suitable for gasoline solubility and in the range of about 1,000 to 10,000, the extent of hydrogenation of said copolymer such that about at least about 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 reacting a metalated, conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, optionally hydrogenated, 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, and wherein if said metalated copolymer has not previously been hydrogenated, subsequently hydrogenating said grafted copolymer.
Claim 2
Dependent Claim 274 words
Hydrocarbon fuel compositions exhibiting carburetor detergency properties comprising a major amount of a liquid hydrocarbon fuel and a minor effective amount of gasoline-soluble nitrogen-containing organic 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 less than about 35 weight percent, a number average molecular weight suitable for gasoline solubility and in the range of about 1,000 to 10,000, the extent of hydrogenation of said copolymer such that about at least about 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 reacting a metalated, conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, optionally hydrogenated, 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, and wherein if said metalated copolymer has not previously been hydrogenated, subsequently hydrogenating said grafted copolymer.
Claim 3
Dependent Claim 31 words
The composition of claim 1 wherein X is selected from ##STR4## wherein each R 4 is the same or different and is hydrogen, or an alkyl, cycloalkyl, aryl, or combination radical.
Claim 4
Dependent Claim 50 words
The composition according to claim 1 wherein the hydrogenated, nitrogen-containing grafted copolymer has a number average molecular weight in the range of about 1,000 to 10,000, a vinyl unsaturation content prior to hydrogenation of about 20 to 95 percent, and a nitrogen content of about 0.01 to 5 weight percent.
Claim 5
Dependent Claim 40 words
The composition according to claim 3 wherein said hydrogenated, nitrogen-containing, grafted copolymer has a number average molecular weight in the range of about 5,500 to 8,500, and a vinyl unsaturation content prior to hydrogenation of about 20 to 70 percent.
Claim 6
Dependent Claim 49 words
The composition according to claim 4 wherein the hydrocarbon fuel is an unleaded motor fuel having a boiling point in the range of about 70° F. to 450° F., and said nitrogen-containing grafted, hydrogenated copolymer exhibits a nitrogen content in the range of about 0.05 to 0.5 weight percent.
Claim 7
Dependent Claim 29 words
The composition according to claim 5 employing said hydrogenated, nitrogen-containing grafted copolymer in the range of about 1 to 30 pounds per 1,000 barrels of fuel excluding other additives.
Claim 8
Dependent Claim 19 words
The composition according to claim 6 wherein said nitrogen-containing organic compound is selected from the group consisting of ##STR5##
Claim 9
Dependent Claim 26 words
The 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 36 words
The composition according to claim 8 wherein said hydrogenated copolymer is a 41/59 weight percent butadiene/styrene hydrogenated block copolymer having a block styrene content of about 1.1 weight percent, and said nitrogen-containing organic compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 11
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 12
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is p-dimethylaminobenzaldehyde.
Claim 13
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is 3-dimethylaminoproprionitrile.
Claim 14
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is 4-diethylamino-2-butanone.
Claim 15
Dependent Claim 27 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is N.tbd.C-CH 2 CH 2 --CH[(CH 2 ) 2 --N(CH 3 ) 2 ] 2 .
Claim 16
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is ##STR6##
Claim 17
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is ##STR7##
Claim 18
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is ##STR8##
Claim 19
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is ##STR9##
Claim 20
Dependent Claim 29 words
The composition according to claim 8 wherein said nitrogen-containing organic 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 ##STR10##
Claim 22
Dependent Claim 13 words
The composition according to claim 8 wherein said nitrogen-containing organic compound is ##STR11##
Claim 23
Dependent Claim 51 words
The composition of claim 1 wherein said conjugated diene/monovinyl arene 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 conjugated diene homopolymer.
Claim 24
Dependent Claim 33 words
The composition of claim 1 wherein said conjugated diene/monovinyl arene copolymer contains a random block B/A, and wherein the block polystyrene content is in the range of less than about 35 weight percent.
Claim 25
Dependent Claim 30 words
The composition of claim 1 employing in said hydrocarbon fuel said nitrogen-containing grafted hydrogenated copolymer in an amount of about 1 to 30 lbs. per 1000 bbls of the fuel.
Claim 26
Dependent Claim 53 words
The composition of claim 1 wherein said hydrocarbon fuel is an unleaded motor fuel having a boiling point in the range of about 70° F. to 450° F., and said hydrogenated grafted copolymer is employed in an amount of about 2 to about 20 pounds per 1,000 barrels of fuel excluding other additives.
Claim 27
Dependent Claim 35 words
The composition of claim 1 wherein said hydrocarbon fuel is an aviation fuel wherein said hydrogenated grafted copolymer is employed in an amount of about 1 to about 30 pounds per 1,000 barrels of fuel.
Claim 28
Dependent Claim 31 words
The compositions according to claim 1 wherein said X[Q--(NR 2 3 ) n ] m or Y[Q--(NR 2 3 ) n ] m is said X--Q--(NR 2 3 ) n .
Claim 29
Dependent Claim 269 words
An additive concentrate comprising about 10 to 70 weight percent of a detergent additive in a solvent, wherein said detergent additive is a nitrogen-containing organic compound-grafted hydrogenated conjugated diene/monovinylarene copolymer, 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 less than about 35 weight percent, a number average molecular weight suitable for gasoline solubility and in the range of about 1,000 to 10,000, 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 reacting a metalated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, optionally hydrogenated, 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.sup. 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, m is 2 or 3, and wherein if said copolymer has not previously been hydrogenated, subsequently hydrogenating said grafted copolymer.
Claim 30
Dependent Claim 269 words
An additive concentrate comprising about 10 to 70 weight percent of a detergent additive in a solvent, wherein said detergent additive is a nitrogen-containing organic compound-grafted hydrogenated conjugated diene/monovinylarene copolymer, 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 less than about 35 weight percent, a number average molecular weight suitable for gasoline solubility and in the range of about 1,000 to 10,000, 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 reacting a metalated conjugated diene hydrocarbon/monovinylarene hydrocarbon copolymer, optionally hydrogenated, 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.sup. 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, m is 2 or 3, and wherein if said copolymer has not previously been hydrogenated, subsequently hydrogenating said grafted copolymer.
Claim 31
Dependent Claim 20 words
The additive concentrate according to claim 28 wherein said nitrogen-containing organic compound is selected from the group consisting of ##STR12##
Claim 32
Dependent Claim 27 words
The additive concentrate according to claim 29 wherein said copolymer is a copolymer of butadiene and styrene, isoprene and styrene, butadiene and α-methylstyrene, or isoprene and α-methylstyrene.
Claim 33
Dependent Claim 37 words
The additive concentrate according to claim 30 wherein said hydrogenated copolymer is a 41/59 weight percent butadiene/styrene hydrogenated block copolymer having a block styrene content of about 1.1 weight percent, and said nitrogen-containing organic compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 34
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is 4-dimethylamino-3-methyl-2-butanone.
Claim 35
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is p-dimethylaminobenzaldehyde.
Claim 36
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is 3-dimethylaminopropionitrile.
Claim 37
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is 4-diethylamino-2-butanone.
Claim 38
Dependent Claim 28 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is N.tbd.C--CH 2 CH 2 --CH[(CH 2 ) 2 --N(CH 3 ) 2 ] 2 .
Claim 39
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR13##
Claim 40
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR14##
Claim 41
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR15##
Claim 42
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR16##
Claim 43
Dependent Claim 30 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is CH 3 N═CH--CH 2 --C(CH 3 ) 2 --CH 2 --N(C 4 H 9 ) 2 .
Claim 44
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR17##
Claim 45
Dependent Claim 14 words
The additive concentrate according to claim 30 wherein said nitrogen-containing organic compound is ##STR18##
Claim 46
Dependent Claim 52 words
The additive concentrate of claim 28 wherein said conjugated diene/monovinyl arene 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 conjugated diene homopolymer.
Claim 47
Dependent Claim 34 words
The additive concentrate of claim 28 wherein said conjugated diene/monovinyl arene copolymer contains a random block B/A, and wherein the block polystyrene content is in the range of less than about 35 weight percent.
Claim 48
Dependent Claim 32 words
The additive concentrate according to claim 28 wherein said X[Q--(NR 2 3 ) n ] m or Y[Q--(NR 2 3 ) n ] m is said X--Q--(NR 2 3 ) n .

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-12-09 1984-06-09 1984-12-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-12-09 1988-06-09 1988-12-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-12-09 1992-06-09 1992-12-09 $7700.00 Window Closed / Lapsed

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